data_L
_audit_creation_date              2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled Mar 28 2017 19:26:29 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number      '2016/4'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C22 H30 N4 O2'
_chemical_formula_sum             'C22 H30 N4 O2'
_chemical_formula_weight          382.50
_chemical_melting_point           ?
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'
 'N' 'N' 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    6.8980(4)
_cell_length_b                    8.2874(5)
_cell_length_c                    9.6802(6)
_cell_angle_alpha                 79.149(3)
_cell_angle_beta                  69.618(3)
_cell_angle_gamma                 83.152(3)
_cell_volume                      508.60(5)
_cell_formula_units_Z             1
_cell_measurement_reflns_used     1955
_cell_measurement_temperature     150(2)
_cell_measurement_theta_max       27.128
_cell_measurement_theta_min       2.273
_shelx_estimated_absorpt_T_max    0.994
_shelx_estimated_absorpt_T_min    0.976
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_exptl_crystal_colour              yellow
_exptl_crystal_density_diffrn     1.249
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description         block
_exptl_crystal_F_000              206
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.08
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0303
_diffrn_reflns_av_unetI/netI      0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_number             9094
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          27.128
_diffrn_reflns_theta_min          2.273
_diffrn_ambient_temperature       150.0
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type CCD _diffrn_measurement_method         'omega and phi scans'
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    ?
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1956
_reflns_number_total              2235
_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.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        ?
_computing_data_collection        ?
_computing_data_reduction         ?
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max          0.257
_refine_diff_density_min          -0.203
_refine_diff_density_rms          0.036
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      133
_refine_ls_number_reflns          2235
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0418
_refine_ls_R_factor_gt            0.0364
_refine_ls_restrained_S_all       1.070
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0596P)²+0.0811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1023
_refine_ls_wR_factor_ref          0.1062
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
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 0.60383(11) 0.26005(9) 0.11861(8) 0.0283(2) Uani 1 1 d . . . . .
 H1 H 0.687(2) 0.174(2) 0.0795(18) 0.058(4) Uiso 1 1 d . . . . .
 N1 N 0.93844(12) 0.06677(9) 0.02968(8) 0.0223(2) Uani 1 1 d . . . . .
 N2 N 0.63693(12) 0.71381(10) 0.34685(9) 0.0229(2) Uani 1 1 d . . . . .
 C1 C 0.72050(14) 0.34865(11) 0.16181(10) 0.0203(2) Uani 1 1 d . . . . .
 C2 C 0.62356(14) 0.48340(11) 0.22980(10) 0.0214(2) Uani 1 1 d . . . . .
 H2 H 0.480486 0.509620 0.245068 0.026 Uiso 1 1 calc R . . . .
 C3 C 0.73421(14) 0.58222(11) 0.27669(9) 0.0191(2) Uani 1 1 d . . . . .
 C4 C 0.94865(14) 0.54101(11) 0.24937(10) 0.0211(2) Uani 1 1 d . . . . .
 H4 H 1.027658 0.606174 0.278478 0.025 Uiso 1 1 calc R . . . .
 C5 C 1.04286(14) 0.40715(11) 0.18093(10) 0.0213(2) Uani 1 1 d . . . . .
 H5 H 1.186833 0.382709 0.162947 0.026 Uiso 1 1 calc R . . . .
 C6 C 0.93333(14) 0.30538(11) 0.13673(10) 0.0197(2) Uani 1 1 d . . . . .
 C7 C 1.03676(14) 0.16461(11) 0.06862(10) 0.0215(2) Uani 1 1 d . . . . .
 H7 H 1.180856 0.142668 0.051690 0.026 Uiso 1 1 calc R . . . .
 C8 C 0.75466(14) 0.83574(11) 0.36996(10) 0.0222(2) Uani 1 1 d . . . . .
 H8A H 0.678329 0.944482 0.364825 0.027 Uiso 1 1 calc R . . . .
 H8B H 0.889664 0.844121 0.288161 0.027 Uiso 1 1 calc R . . . .
 C9 C 0.79312(16) 0.79481(13) 0.51855(11) 0.0298(2) Uani 1 1 d . . . . .
 H9A H 0.660167 0.789372 0.600310 0.045 Uiso 1 1 calc GR . . . .
 H9B H 0.872800 0.880406 0.527294 0.045 Uiso 1 1 calc GR . . . .
 H9C H 0.871174 0.688300 0.523746 0.045 Uiso 1 1 calc GR . . . .
 C10 C 0.41462(14) 0.75247(12) 0.38229(10) 0.0238(2) Uani 1 1 d . . . . .
 H10A H 0.363863 0.812436 0.468693 0.029 Uiso 1 1 calc R . . . .
 H10B H 0.342591 0.648634 0.411319 0.029 Uiso 1 1 calc R . . . .
 C11 C 0.36086(15) 0.85667(13) 0.25150(12) 0.0299(2) Uani 1 1 d . . . . .
 H11A H 0.434572 0.958420 0.220608 0.045 Uiso 1 1 calc GR . . . .
 H11B H 0.211223 0.883735 0.281996 0.045 Uiso 1 1 calc GR . . . .
 H11C H 0.402241 0.794818 0.167846 0.045 Uiso 1 1 calc GR . . . .


_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 H1 0.911(17) . ?
 O1 C1 1.3611(11) . ?
 N1 N1 1.3971(14) 2_755 ?
 N1 C7 1.2976(13) . ?
 N2 C3 1.3739(11) . ?
 N2 C8 1.4622(11) . ?
 N2 C10 1.4594(12) . ?
 C1 C2 1.3855(12) . ?
 C1 C6 1.4149(13) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.4105(12) . ?
 C3 C4 1.4198(13) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.3772(13) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.4065(12) . ?
 C6 C7 1.4382(12) . ?
 C7 H7 0.9500 . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.5215(13) . ?
 C9 H9A 0.9800 . ?
 C9 H9B 0.9800 . ?
 C9 H9C 0.9800 . ?
 C10 H10A 0.9900 . ?
 C10 H10B 0.9900 . ?
 C10 C11 1.5248(14) . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 H11C 0.9800 . ?

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
 C1 O1 H1 107.2(10) . . ?
 C7 N1 N1 113.94(10) . 2_755 ?
 C3 N2 C8 121.47(7) . . ?
 C3 N2 C10 121.74(8) . . ?
 C10 N2 C8 116.20(7) . . ?
 O1 C1 C2 117.53(8) . . ?
 O1 C1 C6 121.11(8) . . ?
 C2 C1 C6 121.36(8) . . ?
 C1 C2 H2 119.5 . . ?
 C1 C2 C3 120.97(8) . . ?
 C3 C2 H2 119.5 . . ?
 N2 C3 C2 120.90(8) . . ?
 N2 C3 C4 121.23(8) . . ?
 C2 C3 C4 117.87(8) . . ?
 C3 C4 H4 119.8 . . ?
 C5 C4 C3 120.42(8) . . ?
 C5 C4 H4 119.8 . . ?
 C4 C5 H5 118.9 . . ?
 C4 C5 C6 122.29(8) . . ?
 C6 C5 H5 118.9 . . ?
 C1 C6 C7 122.44(9) . . ?
 C5 C6 C1 117.08(8) . . ?
 C5 C6 C7 120.49(8) . . ?
 N1 C7 C6 121.73(9) . . ?
 N1 C7 H7 119.1 . . ?
 C6 C7 H7 119.1 . . ?
 N2 C8 H8A 108.9 . . ?
 N2 C8 H8B 108.9 . . ?
 N2 C8 C9 113.31(8) . . ?
 H8A C8 H8B 107.7 . . ?
 C9 C8 H8A 108.9 . . ?
 C9 C8 H8B 108.9 . . ?
 C8 C9 H9A 109.5 . . ?
 C8 C9 H9B 109.5 . . ?
 C8 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?
 N2 C10 H10A 109.1 . . ?
 N2 C10 H10B 109.1 . . ?
 N2 C10 C11 112.46(8) . . ?
 H10A C10 H10B 107.8 . . ?
 C11 C10 H10A 109.1 . . ?
 C11 C10 H10B 109.1 . . ?
 C10 C11 H11A 109.5 . . ?
 C10 C11 H11B 109.5 . . ?
 C10 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
