 
data_NZB_Stanford
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H29 Cl3 O4'
_chemical_formula_weight          451.79
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 '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'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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, -z'
 
_cell_length_a                    7.22880(10)
_cell_length_b                    10.3110(2)
_cell_length_c                    15.9253(3)
_cell_angle_alpha                 75.3280(10)
_cell_angle_beta                  87.2510(10)
_cell_angle_gamma                 72.8190(10)
_cell_volume                      1096.60(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9950
_cell_measurement_theta_min       2.21
_cell_measurement_theta_max       25.36
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.368
_exptl_crystal_F_000              476
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.100
_exptl_crystal_size_mid           0.100
_exptl_crystal_size_min           0.080
_exptl_absorpt_coefficient_mu     0.442
_shelx_estimated_absorpt_T_min    0.957
_shelx_estimated_absorpt_T_max    0.965
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.698
_exptl_absorpt_correction_T_max   0.745
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  8.366
_diffrn_reflns_number             29024
_diffrn_reflns_av_unetI/netI      0.0197
_diffrn_reflns_av_R_equivalents   0.0297
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          1.322
_diffrn_reflns_theta_max          25.367
_diffrn_reflns_theta_full         25.000
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4023
_reflns_number_gt                 3568
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Mercury'
_computing_publication_material   'WinGX'
_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)+(0.0449P)²+0.5984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4023
_refine_ls_number_parameters      262
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0366
_refine_ls_R_factor_gt            0.0320
_refine_ls_wR_factor_ref          0.0867
_refine_ls_wR_factor_gt           0.0835
_refine_ls_goodness_of_fit_ref    1.067
_refine_ls_restrained_S_all       1.067
_refine_ls_shift/su_max           0.001
_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
C1 C 0.7726(3) 0.5450(2) 0.59682(12) 0.0281(4) Uani 1 1 d . . . . .
H1A H 0.8328 0.5461 0.5403 0.042 Uiso 1 1 calc R U . . .
H1B H 0.7269 0.4619 0.6158 0.042 Uiso 1 1 calc R U . . .
H1C H 0.8678 0.5424 0.6395 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6001(3) 0.67780(19) 0.58880(11) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.6763(3) 0.8053(2) 0.56916(12) 0.0265(4) Uani 1 1 d . . . . .
H3A H 0.7673 0.8002 0.5216 0.040 Uiso 1 1 calc R U . . .
H3B H 0.7428 0.8064 0.6211 0.040 Uiso 1 1 calc R U . . .
H3C H 0.5678 0.8911 0.5522 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4574(3) 0.6858(2) 0.51736(11) 0.0261(4) Uani 1 1 d . . . . .
H4 H 0.4285 0.5938 0.5308 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2655(3) 0.7991(2) 0.51089(11) 0.0270(4) Uani 1 1 d . . . . .
H5A H 0.1829 0.7955 0.4642 0.032 Uiso 1 1 calc R U . . .
H5B H 0.2879 0.8923 0.4960 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1622(3) 0.77820(19) 0.59728(11) 0.0234(4) Uani 1 1 d . . . . .
H6A H 0.0407 0.8558 0.5931 0.028 Uiso 1 1 calc R U . . .
H6B H 0.1276 0.6894 0.6086 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2874(2) 0.77371(18) 0.67259(10) 0.0191(4) Uani 1 1 d . . . . .
C8 C 0.2890(3) 0.92309(18) 0.67094(11) 0.0233(4) Uani 1 1 d . . . . .
H8A H 0.1666 0.9728 0.6928 0.035 Uiso 1 1 calc R U . . .
H8B H 0.3047 0.9733 0.6112 0.035 Uiso 1 1 calc R U . . .
H8C H 0.3968 0.9184 0.7077 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4848(2) 0.66205(17) 0.67428(10) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.4531 0.5717 0.6820 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6007(2) 0.64374(17) 0.75637(10) 0.0166(3) Uani 1 1 d . . . . .
H10A H 0.6260 0.7331 0.7561 0.020 Uiso 1 1 calc R U . . .
H10B H 0.7269 0.5715 0.7577 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4881(2) 0.59957(17) 0.83704(10) 0.0151(3) Uani 1 1 d . . . . .
C12 C 0.2841(2) 0.70302(17) 0.82967(10) 0.0160(3) Uani 1 1 d . . . . .
H12 H 0.2925 0.7957 0.8351 0.019 Uiso 1 1 calc R U . . .
C13 C 0.1595(2) 0.64753(17) 0.90101(10) 0.0161(3) Uani 1 1 d . . . . .
H13 H 0.2261 0.6302 0.9581 0.019 Uiso 1 1 calc R U . . .
C14 C 0.1380(2) 0.50938(16) 0.89242(10) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.3163(2) 0.40953(17) 0.87517(10) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.4744(2) 0.45138(16) 0.84861(10) 0.0150(3) Uani 1 1 d . . . . .
C17 C 0.6726(2) 0.21326(16) 0.85254(11) 0.0168(3) Uani 1 1 d . . . . .
C18 C 0.8302(3) 0.15958(18) 0.79272(12) 0.0232(4) Uani 1 1 d . . . . .
H18A H 0.7814 0.1962 0.7324 0.035 Uiso 1 1 calc R U . . .
H18B H 0.8683 0.0569 0.8076 0.035 Uiso 1 1 calc R U . . .
H18C H 0.9428 0.1910 0.7996 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7369(3) 0.15931(18) 0.94752(11) 0.0217(4) Uani 1 1 d . . . . .
H19A H 0.8586 0.1791 0.9554 0.033 Uiso 1 1 calc R U . . .
H19B H 0.7565 0.0579 0.9658 0.033 Uiso 1 1 calc R U . . .
H19C H 0.6371 0.2061 0.9827 0.033 Uiso 1 1 calc R U . . .
C20 C 0.4793(2) 0.19164(16) 0.83275(10) 0.0168(3) Uani 1 1 d . . . . .
H20 H 0.4465 0.2340 0.7695 0.020 Uiso 1 1 calc R U . . .
C21 C 0.3150(2) 0.26117(17) 0.88381(11) 0.0178(3) Uani 1 1 d . . . . .
H21A H 0.1899 0.2608 0.8613 0.021 Uiso 1 1 calc R U . . .
H21B H 0.3308 0.2090 0.9457 0.021 Uiso 1 1 calc R U . . .
O1 O 0.18899(16) 0.72121(12) 0.74945(7) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.57682(18) 0.60551(12) 0.91345(7) 0.0178(3) Uani 1 1 d . . . . .
O3 O -0.01560(16) 0.48046(12) 0.90286(7) 0.0187(3) Uani 1 1 d . . . . .
O4 O 0.64219(16) 0.36578(11) 0.82845(7) 0.0175(3) Uani 1 1 d . . . . .
Cl1 Cl 0.56713(8) 0.70831(6) 0.41144(3) 0.03872(15) Uani 1 1 d . . . . .
Cl2 Cl -0.07058(6) 0.77310(4) 0.89980(3) 0.02037(12) Uani 1 1 d . . . . .
Cl3 Cl 0.50119(6) 0.00768(4) 0.85525(3) 0.02278(12) Uani 1 1 d . . . . .
H2 H 0.690(4) 0.581(2) 0.9070(15) 0.041(7) 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
C1 C2 1.537(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.527(3) . ?
C2 C4 1.543(2) . ?
C2 C9 1.560(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.515(3) . ?
C4 Cl1 1.8196(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.531(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O1 1.4511(19) . ?
C7 C8 1.537(2) . ?
C7 C9 1.543(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.527(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.531(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O2 1.4255(19) . ?
C11 C16 1.524(2) . ?
C11 C12 1.533(2) . ?
C12 O1 1.4238(19) . ?
C12 C13 1.519(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.518(2) . ?
C13 Cl2 1.7779(16) . ?
C13 H13 1.0000 . ?
C14 O3 1.2259(19) . ?
C14 C15 1.457(2) . ?
C15 C16 1.350(2) . ?
C15 C21 1.504(2) . ?
C16 O4 1.3518(19) . ?
C17 O4 1.4720(19) . ?
C17 C19 1.517(2) . ?
C17 C18 1.517(2) . ?
C17 C20 1.538(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.512(2) . ?
C20 Cl3 1.7986(16) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
O2 H2 0.79(3) . ?
 
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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 108.80(15) . . ?
C3 C2 C4 112.23(14) . . ?
C1 C2 C4 109.04(15) . . ?
C3 C2 C9 113.08(14) . . ?
C1 C2 C9 108.64(14) . . ?
C4 C2 C9 104.90(13) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 115.26(15) . . ?
C5 C4 Cl1 108.48(12) . . ?
C2 C4 Cl1 110.99(12) . . ?
C5 C4 H4 107.3 . . ?
C2 C4 H4 107.3 . . ?
Cl1 C4 H4 107.3 . . ?
C4 C5 C6 110.11(15) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 112.03(14) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 C6 104.37(13) . . ?
O1 C7 C8 108.75(13) . . ?
C6 C7 C8 109.68(14) . . ?
O1 C7 C9 106.16(12) . . ?
C6 C7 C9 109.50(14) . . ?
C8 C7 C9 117.52(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 109.62(13) . . ?
C10 C9 C2 114.86(13) . . ?
C7 C9 C2 116.05(13) . . ?
C10 C9 H9 105.0 . . ?
C7 C9 H9 105.0 . . ?
C2 C9 H9 105.0 . . ?
C9 C10 C11 110.13(13) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 C16 108.59(12) . . ?
O2 C11 C10 111.05(12) . . ?
C16 C11 C10 111.68(13) . . ?
O2 C11 C12 106.23(12) . . ?
C16 C11 C12 109.73(13) . . ?
C10 C11 C12 109.41(13) . . ?
O1 C12 C13 106.55(12) . . ?
O1 C12 C11 111.76(13) . . ?
C13 C12 C11 110.06(13) . . ?
O1 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C11 C12 H12 109.5 . . ?
C14 C13 C12 110.62(13) . . ?
C14 C13 Cl2 111.08(11) . . ?
C12 C13 Cl2 110.78(11) . . ?
C14 C13 H13 108.1 . . ?
C12 C13 H13 108.1 . . ?
Cl2 C13 H13 108.1 . . ?
O3 C14 C15 121.89(14) . . ?
O3 C14 C13 122.94(14) . . ?
C15 C14 C13 115.10(13) . . ?
C16 C15 C14 120.57(14) . . ?
C16 C15 C21 121.48(15) . . ?
C14 C15 C21 117.89(14) . . ?
C15 C16 O4 123.78(14) . . ?
C15 C16 C11 125.08(14) . . ?
O4 C16 C11 111.14(13) . . ?
O4 C17 C19 107.55(13) . . ?
O4 C17 C18 103.64(13) . . ?
C19 C17 C18 112.57(14) . . ?
O4 C17 C20 106.20(12) . . ?
C19 C17 C20 114.10(14) . . ?
C18 C17 C20 111.91(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 112.41(13) . . ?
C21 C20 Cl3 109.27(11) . . ?
C17 C20 Cl3 110.44(11) . . ?
C21 C20 H20 108.2 . . ?
C17 C20 H20 108.2 . . ?
Cl3 C20 H20 108.2 . . ?
C15 C21 C20 108.91(13) . . ?
C15 C21 H21A 109.9 . . ?
C20 C21 H21A 109.9 . . ?
C15 C21 H21B 109.9 . . ?
C20 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C12 O1 C7 114.87(12) . . ?
C11 O2 H2 106.2(17) . . ?
C16 O4 C17 119.24(12) . . ?
 
_refine_diff_density_max    0.350
_refine_diff_density_min   -0.201
_refine_diff_density_rms    0.052
 
 
 
