 
data_shelx
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C16 H17 N O3'
_chemical_formula_sum
 'C16 H17 N O3' 
_chemical_formula_weight          271.30

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    8.3815(2)
_cell_length_b                    22.4250(2)
_cell_length_c                    8.6781(2)
_cell_angle_alpha                 90
_cell_angle_beta                  117.675(2)
_cell_angle_gamma                 90
_cell_volume                      1444.49(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     28349
_cell_measurement_theta_min       3.90
_cell_measurement_theta_max       75.8
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.248          
_exptl_crystal_F_000              576
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.31
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.11
_exptl_absorpt_coefficient_mu     0.702
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'gaussian and multi-scan'
_exptl_absorpt_correction_T_min   0.713
_exptl_absorpt_correction_T_max   1.00
_exptl_absorpt_process_details    
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'sealed microfocus tube'
_diffrn_measurement_device_type   'Agilent SuperNova with an Atlas S2 CCD'
_diffrn_measurement_method        ω-scans
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             33708
_diffrn_reflns_av_unetI/netI      0.0192
_diffrn_reflns_av_R_equivalents   0.0393
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -28
_diffrn_reflns_limit_k_max        28
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.943
_diffrn_reflns_theta_max          76.170
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.988
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              5984
_reflns_number_gt                 5932
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.938
_reflns_Friedel_fraction_max      0.983
_reflns_Friedel_fraction_full     1.000
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_publ_section_references
;
CrysAlisPro. Rigaku Oxford Diffraction (2019).  CrysAlicPro Software 
System, 1.171.40.37a.

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. and Puschmann, H. 
(2009).  OLEX2: A Complete Structure Solution, Refinement and Analysis Program.  J. 
Appl. Cryst. 42, 339-341.


Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. SHELXT.  An Integrated Space Group 
and Crystal Structure Determination Program.  

Farrugia, L. J. (1999). J. Appl. Cryst., 32, 837-838.  An Integrated System 
of Windows Programs for the Solution, Refinement and Analysis of 
Single Crystal X-ray Diffraction Data.


Sheldrick, G. M.  (2015).  SHELXL-2016/6.  Acta Cryst., C71, 9-18.

Spek, A. L. (2009) PLATON, A Multipurpose Crystallographic Tool, Utrecht 
University, Utrecht, The Netherlands.  Acta Cryst. D65, 148-155. 
;



_computing_data_collection      'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
_computing_cell_refinement      'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
_computing_data_reduction       'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'

_computing_structure_solution     
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_computing_structure_refinement   'Shelxl-2016/6, Sheldrick, G. M.'
_computing_molecular_graphics     'XP SHELXTL/PC, Siemens Analytical' 
_computing_publication_material   'Shelxl-2016/6, Sheldrick, G. M.' 


 

 


_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0661P)²+0.4232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 2830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.09(6)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          5984
_refine_ls_number_parameters      389
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0378
_refine_ls_R_factor_gt            0.0372
_refine_ls_wR_factor_ref          0.1026
_refine_ls_wR_factor_gt           0.1006
_refine_ls_goodness_of_fit_ref    1.020
_refine_ls_restrained_S_all       1.020
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.6279(2) 0.43360(8) 1.2240(2) 0.0273(4) Uani 1 1 d . . . . .
O2 O 0.4322(2) 0.28481(8) 0.8164(2) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.1209(2) 0.44927(8) 0.6440(2) 0.0257(4) Uani 1 1 d . . . . .
H3 H 0.131(4) 0.4822(18) 0.659(4) 0.027(8) Uiso 1 1 d . . . . .
N1 N 0.4860(3) 0.36540(8) 1.0008(3) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.6285(3) 0.38680(10) 1.1533(3) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.7734(3) 0.34121(10) 1.2066(3) 0.0208(4) Uani 1 1 d . . . . .
C3 C 0.9397(3) 0.33931(11) 1.3534(3) 0.0256(5) Uani 1 1 d . . . . .
H3A H 0.979362 0.370361 1.437514 0.031 Uiso 1 1 calc R U . . .
C4 C 1.0464(3) 0.28897(12) 1.3711(3) 0.0278(5) Uani 1 1 d . . . . .
H4 H 1.160495 0.285336 1.470967 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9887(3) 0.24447(11) 1.2461(3) 0.0272(5) Uani 1 1 d . . . . .
H5 H 1.065192 0.211330 1.261156 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8207(3) 0.24721(11) 1.0985(3) 0.0250(5) Uani 1 1 d . . . . .
H6A H 0.781067 0.216716 1.012690 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7146(3) 0.29649(10) 1.0830(3) 0.0203(4) Uani 1 1 d . . . . .
C8 C 0.5288(3) 0.31174(10) 0.9469(3) 0.0219(4) Uani 1 1 d . . . . .
C9 C 0.3136(3) 0.39788(10) 0.9091(3) 0.0229(5) Uani 1 1 d . . . . .
H9 H 0.320349 0.433670 0.980635 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2917(3) 0.42027(10) 0.7325(3) 0.0218(5) Uani 1 1 d . . . . .
H10 H 0.290972 0.384864 0.662071 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4440(3) 0.45992(10) 0.7543(3) 0.0224(5) Uani 1 1 d . . . . .
H11 H 0.456029 0.496164 0.815456 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5650(3) 0.45025(11) 0.6977(3) 0.0246(5) Uani 1 1 d . . . . .
C13 C 0.5720(4) 0.39564(13) 0.6008(4) 0.0345(6) Uani 1 1 d . . . . .
H13A H 0.686942 0.375050 0.668176 0.052 Uiso 1 1 calc R U . . .
H13B H 0.560929 0.407361 0.487478 0.052 Uiso 1 1 calc R U . . .
H13C H 0.472568 0.368888 0.583527 0.052 Uiso 1 1 calc R U . . .
C14 C 0.7078(4) 0.49566(13) 0.7261(4) 0.0356(6) Uani 1 1 d . . . . .
H14A H 0.696342 0.508420 0.613346 0.053 Uiso 1 1 calc R U . . .
H14B H 0.827044 0.477987 0.795771 0.053 Uiso 1 1 calc R U . . .
H14C H 0.693166 0.530213 0.787501 0.053 Uiso 1 1 calc R U . . .
C15 C 0.1603(3) 0.35979(12) 0.8961(4) 0.0311(6) Uani 1 1 d . . . . .
H15 H 0.129855 0.325250 0.824691 0.037 Uiso 1 1 calc R U . . .
C16 C 0.0660(4) 0.37167(16) 0.9783(5) 0.0423(7) Uani 1 1 d . . . . .
H16A H -0.034(6) 0.3474(18) 0.965(5) 0.049(11) Uiso 1 1 d . . . . .
H16B H 0.101(6) 0.411(2) 1.062(7) 0.072(14) Uiso 1 1 d . . . . .
O4 O 0.0277(2) 0.72826(8) 0.2742(2) 0.0276(4) Uani 1 1 d . . . . .
O5 O 0.1575(2) 0.57576(7) 0.6648(2) 0.0241(3) Uani 1 1 d . . . . .
O6 O -0.3161(2) 0.55199(8) 0.1288(2) 0.0280(4) Uani 1 1 d . . . . .
H6 H -0.339(4) 0.5219(15) 0.162(4) 0.023(7) Uiso 1 1 d . . . . .
N2 N 0.0464(2) 0.64710(8) 0.4472(2) 0.0185(4) Uani 1 1 d . . . . .
C17 C 0.1103(3) 0.69899(10) 0.4049(3) 0.0205(4) Uani 1 1 d . . . . .
C18 C 0.2941(3) 0.70880(9) 0.5505(3) 0.0192(4) Uani 1 1 d . . . . .
C19 C 0.4132(3) 0.75522(11) 0.5798(3) 0.0249(5) Uani 1 1 d . . . . .
H19 H 0.385462 0.786938 0.498761 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5754(3) 0.75364(11) 0.7329(3) 0.0263(5) Uani 1 1 d . . . . .
H20 H 0.659924 0.785004 0.757313 0.032 Uiso 1 1 calc R U . . .
C21 C 0.6160(3) 0.70682(11) 0.8510(3) 0.0251(5) Uani 1 1 d . . . . .
H21 H 0.727760 0.706884 0.954514 0.030 Uiso 1 1 calc R U . . .
C22 C 0.4955(3) 0.65990(11) 0.8200(3) 0.0225(4) Uani 1 1 d . . . . .
H22 H 0.522930 0.627785 0.899751 0.027 Uiso 1 1 calc R U . . .
C23 C 0.3344(3) 0.66229(10) 0.6679(3) 0.0186(4) Uani 1 1 d . . . . .
C24 C 0.1756(3) 0.62176(10) 0.6009(3) 0.0181(4) Uani 1 1 d . . . . .
C25 C -0.1367(3) 0.62414(11) 0.3403(3) 0.0226(4) Uani 1 1 d . . . . .
H25 H -0.203539 0.655106 0.250218 0.027 Uiso 1 1 calc R U . . .
C26 C -0.1322(3) 0.56744(11) 0.2427(3) 0.0255(5) Uani 1 1 d . . . . .
H26 H -0.072899 0.534417 0.327873 0.031 Uiso 1 1 calc R U . . .
C27 C -0.0347(3) 0.57750(11) 0.1385(3) 0.0256(5) Uani 1 1 d . . . . .
H27 H -0.094959 0.601612 0.037699 0.031 Uiso 1 1 calc R U . . .
C28 C 0.1267(3) 0.55685(12) 0.1693(3) 0.0278(5) Uani 1 1 d . . . . .
C29 C 0.2464(4) 0.51902(15) 0.3186(4) 0.0400(7) Uani 1 1 d . . . . .
H29A H 0.343571 0.543497 0.405087 0.060 Uiso 1 1 calc R U . . .
H29B H 0.298060 0.487297 0.277895 0.060 Uiso 1 1 calc R U . . .
H29C H 0.176646 0.501250 0.371494 0.060 Uiso 1 1 calc R U . . .
C30 C 0.2035(4) 0.57351(15) 0.0473(4) 0.0399(6) Uani 1 1 d . . . . .
H30A H 0.117996 0.599233 -0.045706 0.060 Uiso 1 1 calc R U . . .
H30B H 0.224557 0.537235 -0.003676 0.060 Uiso 1 1 calc R U . . .
H30C H 0.317665 0.594804 0.112488 0.060 Uiso 1 1 calc R U . . .
C31 C -0.2339(3) 0.61663(12) 0.4462(3) 0.0287(5) Uani 1 1 d . . . . .
H31 H -0.192434 0.586858 0.534153 0.034 Uiso 1 1 calc R U . . .
C32 C -0.3742(4) 0.64908(14) 0.4243(4) 0.0331(6) Uani 1 1 d . . . . .
H32A H -0.433(6) 0.645(2) 0.490(6) 0.052(11) Uiso 1 1 d . . . . .
H32B H -0.418(5) 0.6841(18) 0.329(5) 0.046(10) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C1 1.217(3) . ?
O2 C8 1.204(3) . ?
O3 C10 1.429(3) . ?
O3 H3 0.75(4) . ?
N1 C1 1.393(3) . ?
N1 C8 1.397(3) . ?
N1 C9 1.478(3) . ?
C1 C2 1.487(3) . ?
C2 C7 1.381(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.403(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.493(3) . ?
C9 C15 1.503(3) . ?
C9 C10 1.541(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.493(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.334(4) . ?
C11 H11 0.9500 . ?
C12 C14 1.502(4) . ?
C12 C13 1.502(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.314(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.96(4) . ?
C16 H16B 1.08(5) . ?
O4 C17 1.211(3) . ?
O5 C24 1.214(3) . ?
O6 C26 1.435(3) . ?
O6 H6 0.79(3) . ?
N2 C24 1.390(3) . ?
N2 C17 1.400(3) . ?
N2 C25 1.469(3) . ?
C17 C18 1.487(3) . ?
C18 C19 1.382(3) . ?
C18 C23 1.386(3) . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.488(3) . ?
C25 C31 1.494(3) . ?
C25 C26 1.538(3) . ?
C25 H25 1.0000 . ?
C26 C27 1.491(3) . ?
C26 H26 1.0000 . ?
C27 C28 1.334(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.483(4) . ?
C28 C30 1.520(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.319(4) . ?
C31 H31 0.9500 . ?
C32 H32A 0.91(4) . ?
C32 H32B 1.07(4) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C10 O3 H3 110(3) . . ?
C1 N1 C8 112.02(19) . . ?
C1 N1 C9 122.3(2) . . ?
C8 N1 C9 125.67(19) . . ?
O1 C1 N1 125.0(2) . . ?
O1 C1 C2 129.0(2) . . ?
N1 C1 C2 105.94(19) . . ?
C7 C2 C3 122.4(2) . . ?
C7 C2 C1 108.18(19) . . ?
C3 C2 C1 129.4(2) . . ?
C2 C3 C4 116.3(2) . . ?
C2 C3 H3A 121.8 . . ?
C4 C3 H3A 121.8 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 116.9(2) . . ?
C7 C6 H6A 121.6 . . ?
C5 C6 H6A 121.6 . . ?
C2 C7 C6 121.5(2) . . ?
C2 C7 C8 108.3(2) . . ?
C6 C7 C8 130.2(2) . . ?
O2 C8 N1 125.6(2) . . ?
O2 C8 C7 128.9(2) . . ?
N1 C8 C7 105.52(18) . . ?
N1 C9 C15 110.40(19) . . ?
N1 C9 C10 109.33(19) . . ?
C15 C9 C10 114.1(2) . . ?
N1 C9 H9 107.6 . . ?
C15 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
O3 C10 C11 112.42(19) . . ?
O3 C10 C9 108.01(19) . . ?
C11 C10 C9 111.58(18) . . ?
O3 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C12 C11 C10 127.4(2) . . ?
C12 C11 H11 116.3 . . ?
C10 C11 H11 116.3 . . ?
C11 C12 C14 120.9(2) . . ?
C11 C12 C13 124.9(2) . . ?
C14 C12 C13 114.1(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C9 123.6(3) . . ?
C16 C15 H15 118.2 . . ?
C9 C15 H15 118.2 . . ?
C15 C16 H16A 122(3) . . ?
C15 C16 H16B 119(3) . . ?
H16A C16 H16B 119(4) . . ?
C26 O6 H6 109(2) . . ?
C24 N2 C17 111.65(19) . . ?
C24 N2 C25 125.64(19) . . ?
C17 N2 C25 122.71(19) . . ?
O4 C17 N2 125.0(2) . . ?
O4 C17 C18 129.2(2) . . ?
N2 C17 C18 105.77(18) . . ?
C19 C18 C23 121.6(2) . . ?
C19 C18 C17 130.0(2) . . ?
C23 C18 C17 108.42(19) . . ?
C18 C19 C20 117.3(2) . . ?
C18 C19 H19 121.4 . . ?
C20 C19 H19 121.4 . . ?
C19 C20 C21 121.2(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 116.9(2) . . ?
C23 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
C22 C23 C18 121.8(2) . . ?
C22 C23 C24 130.4(2) . . ?
C18 C23 C24 107.70(19) . . ?
O5 C24 N2 125.3(2) . . ?
O5 C24 C23 128.3(2) . . ?
N2 C24 C23 106.38(18) . . ?
N2 C25 C31 111.04(19) . . ?
N2 C25 C26 110.58(18) . . ?
C31 C25 C26 113.9(2) . . ?
N2 C25 H25 107.0 . . ?
C31 C25 H25 107.0 . . ?
C26 C25 H25 107.0 . . ?
O6 C26 C27 109.57(19) . . ?
O6 C26 C25 106.58(19) . . ?
C27 C26 C25 111.69(19) . . ?
O6 C26 H26 109.7 . . ?
C27 C26 H26 109.7 . . ?
C25 C26 H26 109.7 . . ?
C28 C27 C26 128.1(2) . . ?
C28 C27 H27 116.0 . . ?
C26 C27 H27 116.0 . . ?
C27 C28 C29 125.8(2) . . ?
C27 C28 C30 119.6(2) . . ?
C29 C28 C30 114.6(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C25 123.6(3) . . ?
C32 C31 H31 118.2 . . ?
C25 C31 H31 118.2 . . ?
C31 C32 H32A 123(3) . . ?
C31 C32 H32B 119(2) . . ?
H32A C32 H32B 118(3) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C8 N1 C1 O1 177.5(2) . . . . ?
C9 N1 C1 O1 -1.3(3) . . . . ?
C8 N1 C1 C2 -2.8(2) . . . . ?
C9 N1 C1 C2 178.50(19) . . . . ?
O1 C1 C2 C7 -178.3(2) . . . . ?
N1 C1 C2 C7 2.0(2) . . . . ?
O1 C1 C2 C3 3.3(4) . . . . ?
N1 C1 C2 C3 -176.5(2) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 177.9(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C1 C2 C7 C6 -179.4(2) . . . . ?
C3 C2 C7 C8 178.1(2) . . . . ?
C1 C2 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C1 N1 C8 O2 -177.4(2) . . . . ?
C9 N1 C8 O2 1.3(4) . . . . ?
C1 N1 C8 C7 2.5(2) . . . . ?
C9 N1 C8 C7 -178.9(2) . . . . ?
C2 C7 C8 O2 178.7(2) . . . . ?
C6 C7 C8 O2 -2.6(4) . . . . ?
C2 C7 C8 N1 -1.1(2) . . . . ?
C6 C7 C8 N1 177.6(2) . . . . ?
C1 N1 C9 C15 -120.9(2) . . . . ?
C8 N1 C9 C15 60.6(3) . . . . ?
C1 N1 C9 C10 112.8(2) . . . . ?
C8 N1 C9 C10 -65.7(3) . . . . ?
N1 C9 C10 O3 177.65(18) . . . . ?
C15 C9 C10 O3 53.5(3) . . . . ?
N1 C9 C10 C11 -58.3(2) . . . . ?
C15 C9 C10 C11 177.5(2) . . . . ?
O3 C10 C11 C12 -121.9(3) . . . . ?
C9 C10 C11 C12 116.5(3) . . . . ?
C10 C11 C12 C14 178.2(2) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
N1 C9 C15 C16 112.5(3) . . . . ?
C10 C9 C15 C16 -123.9(3) . . . . ?
C24 N2 C17 O4 176.7(2) . . . . ?
C25 N2 C17 O4 -4.1(3) . . . . ?
C24 N2 C17 C18 -3.0(2) . . . . ?
C25 N2 C17 C18 176.18(18) . . . . ?
O4 C17 C18 C19 4.4(4) . . . . ?
N2 C17 C18 C19 -175.9(2) . . . . ?
O4 C17 C18 C23 -177.6(2) . . . . ?
N2 C17 C18 C23 2.2(2) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
C17 C18 C19 C20 177.5(2) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C21 C22 C23 C24 -176.7(2) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C17 C18 C23 C22 -178.34(19) . . . . ?
C19 C18 C23 C24 177.6(2) . . . . ?
C17 C18 C23 C24 -0.6(2) . . . . ?
C17 N2 C24 O5 -177.9(2) . . . . ?
C25 N2 C24 O5 3.0(3) . . . . ?
C17 N2 C24 C23 2.7(2) . . . . ?
C25 N2 C24 C23 -176.50(19) . . . . ?
C22 C23 C24 O5 -3.2(4) . . . . ?
C18 C23 C24 O5 179.4(2) . . . . ?
C22 C23 C24 N2 176.3(2) . . . . ?
C18 C23 C24 N2 -1.2(2) . . . . ?
C24 N2 C25 C31 54.5(3) . . . . ?
C17 N2 C25 C31 -124.6(2) . . . . ?
C24 N2 C25 C26 -73.0(3) . . . . ?
C17 N2 C25 C26 107.9(2) . . . . ?
N2 C25 C26 O6 -174.08(19) . . . . ?
C31 C25 C26 O6 60.0(3) . . . . ?
N2 C25 C26 C27 -54.4(3) . . . . ?
C31 C25 C26 C27 179.7(2) . . . . ?
O6 C26 C27 C28 -133.7(3) . . . . ?
C25 C26 C27 C28 108.4(3) . . . . ?
C26 C27 C28 C29 -0.6(4) . . . . ?
C26 C27 C28 C30 -178.9(2) . . . . ?
N2 C25 C31 C32 112.6(3) . . . . ?
C26 C25 C31 C32 -121.8(3) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O3 H3 O5  0.75(4) 2.11(4) 2.850(2) 171(3) .
C10 H10 O2  1.00 2.60 3.217(3) 119.9 .
C15 H15 O4  0.95 2.48 3.347(3) 151.5 2_546
O6 H6 O1  0.79(3) 2.10(3) 2.883(3) 168(3) 1_454
 
_refine_diff_density_max    0.385
_refine_diff_density_min   -0.211
_refine_diff_density_rms    0.043



