# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cxy1215_0m
_database_code_depnum_ccdc_archive 'CCDC 2101130'
loop_
_audit_author_name
_audit_author_address
'Xiaoyong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2020-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4073(6)
_cell_length_b                   8.7265(5)
_cell_length_c                   14.6032(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.709(2)
_cell_angle_gamma                90
_cell_volume                     1321.78(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0790 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.9514. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18279
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             3054
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.054
_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)+(0.0467P)²+0.4845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0960
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.45759(8) 0.24263(10) 0.08785(5) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.15326(8) 0.38109(10) 0.49077(6) 0.0238(2) Uani 1 1 d . . . . .
H2 H 0.091217 0.354826 0.520617 0.036 Uiso 1 1 calc GR . . . .
N1 N 0.38315(9) 0.41600(10) 0.19034(6) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.77659(11) 0.23814(14) 0.31508(8) 0.0220(3) Uani 1 1 d . . . . .
H1 H 0.854079 0.180111 0.319681 0.026 Uiso 1 1 calc R . . . .
C2 C 0.69291(11) 0.22765(13) 0.23587(8) 0.0202(2) Uani 1 1 d . . . . .
H2A H 0.712652 0.165096 0.185668 0.024 Uiso 1 1 calc R . . . .
C3 C 0.57942(10) 0.31215(12) 0.23302(7) 0.0163(2) Uani 1 1 d . . . . .
C4 C 0.47155(10) 0.31547(12) 0.15995(7) 0.0158(2) Uani 1 1 d . . . . .
C5 C 0.24753(10) 0.40874(11) 0.17580(7) 0.0149(2) Uani 1 1 d . . . . .
C6 C 0.19412(11) 0.43733(12) 0.25893(7) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.06130(11) 0.44493(12) 0.26034(8) 0.0185(2) Uani 1 1 d . . . . .
H7 H 0.023134 0.466483 0.315826 0.022 Uiso 1 1 calc R . . . .
C8 C -0.01561(11) 0.42021(13) 0.17836(8) 0.0206(2) Uani 1 1 d . . . . .
H8 H -0.106748 0.426849 0.178129 0.025 Uiso 1 1 calc R . . . .
C9 C 0.17315(11) 0.38063(12) 0.09437(7) 0.0179(2) Uani 1 1 d . . . . .
H9 H 0.211380 0.358604 0.038973 0.021 Uiso 1 1 calc R . . . .
C10 C 0.03972(11) 0.38614(13) 0.09750(8) 0.0203(2) Uani 1 1 d . . . . .
H10 H -0.014400 0.366198 0.043219 0.024 Uiso 1 1 calc R . . . .
C11 C 0.29983(10) 0.44863(12) 0.33723(7) 0.0142(2) Uani 1 1 d . . . . .
H11 H 0.283566 0.537503 0.377934 0.017 Uiso 1 1 calc R . . . .
C12 C 0.31350(11) 0.29961(12) 0.39370(7) 0.0163(2) Uani 1 1 d . . . . .
H12A H 0.336685 0.215234 0.352833 0.020 Uiso 1 1 calc R . . . .
H12B H 0.385223 0.311860 0.442024 0.020 Uiso 1 1 calc R . . . .
C13 C 0.19255(11) 0.25477(12) 0.43883(8) 0.0183(2) Uani 1 1 d . . . . .
H13A H 0.123215 0.226695 0.391315 0.022 Uiso 1 1 calc R . . . .
H13B H 0.210431 0.165165 0.479472 0.022 Uiso 1 1 calc R . . . .
C14 C 0.41991(10) 0.47992(12) 0.28274(7) 0.0149(2) Uani 1 1 d . . . . .
H14 H 0.432916 0.593035 0.277615 0.018 Uiso 1 1 calc R . . . .
C15 C 0.54815(10) 0.40376(12) 0.30637(7) 0.0159(2) Uani 1 1 d . . . . .
C16 C 0.63400(11) 0.41705(13) 0.38397(7) 0.0193(2) Uani 1 1 d . . . . .
H16 H 0.615393 0.482099 0.433344 0.023 Uiso 1 1 calc R . . . .
C17 C 0.74819(11) 0.33266(14) 0.38775(8) 0.0213(3) Uani 1 1 d . . . . .
H17 H 0.807499 0.339701 0.440612 0.026 Uiso 1 1 calc R . . . .


_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 C4 1.2282(13) . ?
O2 H2 0.8400 . ?
O2 C13 1.4172(13) . ?
N1 C4 1.3711(14) . ?
N1 C5 1.4115(14) . ?
N1 C14 1.4810(13) . ?
C1 H1 0.9500 . ?
C1 C2 1.3925(16) . ?
C1 C17 1.3947(17) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3901(16) . ?
C3 C4 1.4843(15) . ?
C3 C15 1.3962(15) . ?
C5 C6 1.3984(15) . ?
C5 C9 1.3864(14) . ?
C6 C7 1.3857(15) . ?
C6 C11 1.5235(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.4011(15) . ?
C8 H8 0.9500 . ?
C8 C10 1.3878(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3941(16) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.5402(14) . ?
C11 C14 1.5597(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5193(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 1.0000 . ?
C14 C15 1.5054(15) . ?
C15 C16 1.3892(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3953(17) . ?
C17 H17 0.9500 . ?

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
C13 O2 H2 109.5 . . ?
C4 N1 C5 127.72(9) . . ?
C4 N1 C14 113.95(9) . . ?
C5 N1 C14 109.53(8) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C17 120.91(11) . . ?
C17 C1 H1 119.5 . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 C1 117.51(10) . . ?
C3 C2 H2A 121.2 . . ?
C2 C3 C4 128.50(10) . . ?
C2 C3 C15 122.12(10) . . ?
C15 C3 C4 109.27(9) . . ?
O1 C4 N1 124.98(10) . . ?
O1 C4 C3 129.45(10) . . ?
N1 C4 C3 105.53(9) . . ?
C6 C5 N1 108.98(9) . . ?
C9 C5 N1 128.17(10) . . ?
C9 C5 C6 122.85(10) . . ?
C5 C6 C11 110.43(9) . . ?
C7 C6 C5 119.31(10) . . ?
C7 C6 C11 130.20(10) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.72(10) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C8 C7 120.81(10) . . ?
C10 C8 H8 119.6 . . ?
C5 C9 H9 121.5 . . ?
C5 C9 C10 116.96(10) . . ?
C10 C9 H9 121.5 . . ?
C8 C10 C9 121.28(10) . . ?
C8 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C6 C11 H11 110.4 . . ?
C6 C11 C12 112.12(8) . . ?
C6 C11 C14 100.83(8) . . ?
C12 C11 H11 110.4 . . ?
C12 C11 C14 112.23(9) . . ?
C14 C11 H11 110.4 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.97(9) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O2 C13 C12 108.52(9) . . ?
O2 C13 H13A 110.0 . . ?
O2 C13 H13B 110.0 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N1 C14 C11 103.95(8) . . ?
N1 C14 H14 109.3 . . ?
N1 C14 C15 101.56(8) . . ?
C11 C14 H14 109.3 . . ?
C15 C14 C11 122.56(9) . . ?
C15 C14 H14 109.3 . . ?
C3 C15 C14 109.57(9) . . ?
C16 C15 C3 119.92(10) . . ?
C16 C15 C14 130.46(10) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.48(10) . . ?
C17 C16 H16 120.8 . . ?
C1 C17 C16 121.00(10) . . ?
C1 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?

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
N1 C5 C6 C7 176.29(9) . . . . ?
N1 C5 C6 C11 -6.19(11) . . . . ?
N1 C5 C9 C10 -177.27(10) . . . . ?
N1 C14 C15 C3 1.79(11) . . . . ?
N1 C14 C15 C16 179.14(11) . . . . ?
C1 C2 C3 C4 -176.48(10) . . . . ?
C1 C2 C3 C15 -0.54(16) . . . . ?
C2 C1 C17 C16 1.30(17) . . . . ?
C2 C3 C4 O1 1.85(19) . . . . ?
C2 C3 C4 N1 179.72(11) . . . . ?
C2 C3 C15 C14 -179.86(10) . . . . ?
C2 C3 C15 C16 2.47(16) . . . . ?
C3 C15 C16 C17 -2.46(16) . . . . ?
C4 N1 C5 C6 134.17(10) . . . . ?
C4 N1 C5 C9 -46.66(16) . . . . ?
C4 N1 C14 C11 -127.69(9) . . . . ?
C4 N1 C14 C15 0.39(11) . . . . ?
C4 C3 C15 C14 -3.23(12) . . . . ?
C4 C3 C15 C16 179.10(9) . . . . ?
C5 N1 C4 O1 32.03(17) . . . . ?
C5 N1 C4 C3 -145.96(10) . . . . ?
C5 N1 C14 C11 22.53(10) . . . . ?
C5 N1 C14 C15 150.61(8) . . . . ?
C5 C6 C7 C8 1.41(15) . . . . ?
C5 C6 C11 C12 -100.41(10) . . . . ?
C5 C6 C11 C14 19.16(11) . . . . ?
C5 C9 C10 C8 0.80(16) . . . . ?
C6 C5 C9 C10 1.80(16) . . . . ?
C6 C7 C8 C10 1.09(16) . . . . ?
C6 C11 C12 C13 -60.49(12) . . . . ?
C6 C11 C14 N1 -24.11(10) . . . . ?
C6 C11 C14 C15 -137.91(10) . . . . ?
C7 C6 C11 C12 76.75(14) . . . . ?
C7 C6 C11 C14 -163.68(11) . . . . ?
C7 C8 C10 C9 -2.25(17) . . . . ?
C9 C5 C6 C7 -2.93(16) . . . . ?
C9 C5 C6 C11 174.58(9) . . . . ?
C11 C6 C7 C8 -175.55(10) . . . . ?
C11 C12 C13 O2 -53.34(12) . . . . ?
C11 C14 C15 C3 116.78(10) . . . . ?
C11 C14 C15 C16 -65.87(15) . . . . ?
C12 C11 C14 N1 95.38(9) . . . . ?
C12 C11 C14 C15 -18.42(13) . . . . ?
C14 N1 C4 O1 175.74(10) . . . . ?
C14 N1 C4 C3 -2.25(11) . . . . ?
C14 N1 C5 C6 -10.80(11) . . . . ?
C14 N1 C5 C9 168.37(10) . . . . ?
C14 C11 C12 C13 -173.14(9) . . . . ?
C14 C15 C16 C17 -179.57(11) . . . . ?
C15 C3 C4 O1 -174.50(11) . . . . ?
C15 C3 C4 N1 3.37(12) . . . . ?
C15 C16 C17 C1 0.63(16) . . . . ?
C17 C1 C2 C3 -1.33(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cxy1304_0m
_database_code_depnum_ccdc_archive 'CCDC 2101131'
loop_
_audit_author_name
_audit_author_address
'Xiaoyong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2020-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O3'
_chemical_formula_sum            'C22 H22 N2 O3'
_chemical_formula_weight         362.41
_chemical_absolute_configuration .
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6179(7)
_cell_length_b                   15.5833(12)
_cell_length_c                   12.4610(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.679(3)
_cell_angle_gamma                90
_cell_volume                     1863.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0985 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.9556. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44261
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.492
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7791
_reflns_number_total             8583
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 3421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.0158(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         8583
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.3330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0830
_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 Ternary CH refined with riding coordinates:
 C5(H5), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C32(H32A,H32B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21),
 C29(H29), C30(H30), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C),
 C31(H31A,H31B,H31C), C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.17285(14) 0.40984(9) -0.03265(11) 0.0193(3) Uani 1 1 d . . . . .
O2 O -0.00965(15) 0.36210(9) -0.14279(11) 0.0200(3) Uani 1 1 d . . . . .
O3 O 0.29227(17) 0.42668(11) 0.28118(13) 0.0294(4) Uani 1 1 d . . . . .
O4 O 0.64617(14) 0.59707(10) 0.70136(11) 0.0220(3) Uani 1 1 d . . . . .
O5 O 0.56909(17) 0.59246(11) 0.38071(13) 0.0304(4) Uani 1 1 d . . . . .
O6 O 0.81508(15) 0.63406(10) 0.82985(11) 0.0209(3) Uani 1 1 d . . . . .
N1 N -0.04252(17) 0.44588(11) 0.00173(13) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.08452(17) 0.42806(11) 0.17733(13) 0.0167(3) Uani 1 1 d . . . . .
N3 N 0.86351(17) 0.55673(11) 0.68306(13) 0.0173(4) Uani 1 1 d . . . . .
N4 N 0.76228(17) 0.58085(11) 0.49967(13) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.3003(2) 0.37288(16) -0.19019(17) 0.0251(5) Uani 1 1 d . . . . .
H1A H 0.218024 0.353919 -0.234381 0.038 Uiso 1 1 calc GR . . . .
H1B H 0.382779 0.342488 -0.212620 0.038 Uiso 1 1 calc GR . . . .
H1C H 0.312963 0.434784 -0.199357 0.038 Uiso 1 1 calc GR . . . .
C2 C 0.2803(2) 0.35347(14) -0.07314(16) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.0379(2) 0.40143(12) -0.06447(15) 0.0153(4) Uani 1 1 d . . . . .
C4 C 0.0079(2) 0.48713(13) 0.10293(15) 0.0150(4) Uani 1 1 d . . . . .
C5 C -0.1303(2) 0.50582(13) 0.15710(16) 0.0167(4) Uani 1 1 d . . . . .
H5 H -0.124035 0.560552 0.199026 0.020 Uiso 1 1 calc R . . . .
C6 C -0.1390(2) 0.42875(13) 0.23089(16) 0.0181(4) Uani 1 1 d . . . . .
C7 C -0.2483(2) 0.39978(14) 0.28799(16) 0.0216(4) Uani 1 1 d . . . . .
H7 H -0.337209 0.426388 0.279645 0.026 Uiso 1 1 calc R . . . .
C8 C -0.2254(2) 0.33061(15) 0.35819(17) 0.0250(5) Uani 1 1 d . . . . .
H8 H -0.299505 0.310186 0.398160 0.030 Uiso 1 1 calc R . . . .
C9 C 0.4087(2) 0.37948(15) -0.00314(18) 0.0221(4) Uani 1 1 d . . . . .
H9A H 0.425453 0.441090 -0.011421 0.033 Uiso 1 1 calc GR . . . .
H9B H 0.489675 0.347292 -0.025189 0.033 Uiso 1 1 calc GR . . . .
H9C H 0.393869 0.366814 0.072301 0.033 Uiso 1 1 calc GR . . . .
C10 C -0.1951(2) 0.44518(14) -0.01632(16) 0.0180(4) Uani 1 1 d . . . . .
H10A H -0.233888 0.387913 -0.001140 0.022 Uiso 1 1 calc R . . . .
H10B H -0.224304 0.461767 -0.091090 0.022 Uiso 1 1 calc R . . . .
C11 C -0.2407(2) 0.51175(13) 0.06359(17) 0.0186(4) Uani 1 1 d . . . . .
H11A H -0.334298 0.498141 0.087618 0.022 Uiso 1 1 calc R . . . .
H11B H -0.242548 0.569866 0.031452 0.022 Uiso 1 1 calc R . . . .
C12 C -0.0105(2) 0.38772(13) 0.24356(16) 0.0181(4) Uani 1 1 d . . . . .
C13 C -0.0964(3) 0.29147(14) 0.37027(18) 0.0257(5) Uani 1 1 d . . . . .
H13 H -0.082955 0.245060 0.419272 0.031 Uiso 1 1 calc R . . . .
C14 C 0.0143(2) 0.31867(14) 0.31210(17) 0.0230(5) Uani 1 1 d . . . . .
H14 H 0.102606 0.291202 0.319077 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2140(2) 0.45993(14) 0.21278(16) 0.0210(4) Uani 1 1 d . . . . .
C16 C 0.2316(2) 0.54068(14) 0.15346(17) 0.0192(4) Uani 1 1 d . . . . .
C17 C 0.1113(2) 0.55797(13) 0.08991(16) 0.0170(4) Uani 1 1 d . . . . .
C18 C 0.0998(2) 0.63046(14) 0.02584(17) 0.0214(4) Uani 1 1 d . . . . .
H18 H 0.018862 0.641229 -0.019935 0.026 Uiso 1 1 calc R . . . .
C19 C 0.2119(3) 0.68675(15) 0.0315(2) 0.0285(5) Uani 1 1 d . . . . .
H19 H 0.206992 0.737557 -0.010690 0.034 Uiso 1 1 calc R . . . .
C20 C 0.3314(2) 0.67069(16) 0.0974(2) 0.0299(5) Uani 1 1 d . . . . .
H20 H 0.405646 0.711008 0.100053 0.036 Uiso 1 1 calc R . . . .
C21 C 0.3439(2) 0.59712(16) 0.15916(18) 0.0256(5) Uani 1 1 d . . . . .
H21 H 0.425768 0.585558 0.203597 0.031 Uiso 1 1 calc R . . . .
C22 C 0.2424(2) 0.26002(14) -0.05561(19) 0.0242(5) Uani 1 1 d . . . . .
H22A H 0.224273 0.251097 0.020087 0.036 Uiso 1 1 calc GR . . . .
H22B H 0.319673 0.223203 -0.074571 0.036 Uiso 1 1 calc GR . . . .
H22C H 0.158709 0.245534 -0.101036 0.036 Uiso 1 1 calc GR . . . .
C23 C 0.5641(3) 0.73903(16) 0.7448(2) 0.0390(7) Uani 1 1 d . . . . .
H23A H 0.649204 0.750345 0.790137 0.059 Uiso 1 1 calc GR . . . .
H23B H 0.486345 0.771006 0.772571 0.059 Uiso 1 1 calc GR . . . .
H23C H 0.577541 0.757280 0.670952 0.059 Uiso 1 1 calc GR . . . .
C24 C 0.5322(2) 0.64435(14) 0.74611(17) 0.0194(4) Uani 1 1 d . . . . .
C25 C 0.7766(2) 0.59961(14) 0.74585(16) 0.0171(4) Uani 1 1 d . . . . .
C26 C 0.8224(2) 0.51807(13) 0.57843(15) 0.0160(4) Uani 1 1 d . . . . .
C27 C 0.9654(2) 0.49379(14) 0.53541(16) 0.0180(4) Uani 1 1 d . . . . .
H27 H 0.959068 0.439414 0.492757 0.022 Uiso 1 1 calc R . . . .
C28 C 0.9932(2) 0.57021(13) 0.46482(16) 0.0180(4) Uani 1 1 d . . . . .
C29 C 1.1140(2) 0.59484(14) 0.41895(17) 0.0218(4) Uani 1 1 d . . . . .
H29 H 1.198024 0.563569 0.432766 0.026 Uiso 1 1 calc R . . . .
C30 C 1.1099(2) 0.66644(15) 0.35206(18) 0.0248(5) Uani 1 1 d . . . . .
H30 H 1.192565 0.684530 0.320816 0.030 Uiso 1 1 calc R . . . .
C31 C 0.4096(2) 0.62309(15) 0.66723(18) 0.0249(5) Uani 1 1 d . . . . .
H31A H 0.429835 0.642568 0.595100 0.037 Uiso 1 1 calc GR . . . .
H31B H 0.325751 0.652095 0.689566 0.037 Uiso 1 1 calc GR . . . .
H31C H 0.394182 0.560919 0.666228 0.037 Uiso 1 1 calc GR . . . .
C32 C 1.0137(2) 0.55316(14) 0.71175(17) 0.0189(4) Uani 1 1 d . . . . .
H32A H 1.032788 0.536711 0.788010 0.023 Uiso 1 1 calc R . . . .
H32B H 1.058906 0.608945 0.698720 0.023 Uiso 1 1 calc R . . . .
C33 C 1.0630(2) 0.48385(14) 0.63617(17) 0.0197(4) Uani 1 1 d . . . . .
H33A H 1.161108 0.493390 0.619738 0.024 Uiso 1 1 calc R . . . .
H33B H 1.054260 0.426042 0.668006 0.024 Uiso 1 1 calc R . . . .
C34 C 0.8713(2) 0.61748(13) 0.44383(16) 0.0185(4) Uani 1 1 d . . . . .
C35 C 0.7090(2) 0.45155(14) 0.58118(16) 0.0170(4) Uani 1 1 d . . . . .
C36 C 0.5990(2) 0.47460(14) 0.50940(16) 0.0195(4) Uani 1 1 d . . . . .
C37 C 0.4816(2) 0.42348(15) 0.49393(18) 0.0237(5) Uani 1 1 d . . . . .
H37 H 0.406451 0.439435 0.444794 0.028 Uiso 1 1 calc R . . . .
C38 C 0.4780(2) 0.34807(16) 0.55293(18) 0.0257(5) Uani 1 1 d . . . . .
H38 H 0.399742 0.311035 0.543033 0.031 Uiso 1 1 calc R . . . .
C39 C 0.5873(2) 0.32585(15) 0.62645(17) 0.0241(5) Uani 1 1 d . . . . .
H39 H 0.581857 0.274176 0.666417 0.029 Uiso 1 1 calc R . . . .
C40 C 0.7044(2) 0.37806(14) 0.64241(17) 0.0208(4) Uani 1 1 d . . . . .
H40 H 0.778273 0.363569 0.693494 0.025 Uiso 1 1 calc R . . . .
C41 C 0.6335(2) 0.55537(14) 0.45364(16) 0.0205(4) Uani 1 1 d . . . . .
C42 C 0.8652(2) 0.68802(14) 0.37636(17) 0.0223(5) Uani 1 1 d . . . . .
H42 H 0.781048 0.719048 0.362011 0.027 Uiso 1 1 calc R . . . .
C43 C 0.9878(3) 0.71167(14) 0.33030(17) 0.0252(5) Uani 1 1 d . . . . .
H43 H 0.987422 0.759626 0.283213 0.030 Uiso 1 1 calc R . . . .
C44 C 0.5078(3) 0.6107(2) 0.85712(19) 0.0402(7) Uani 1 1 d . . . . .
H44A H 0.504624 0.547845 0.855425 0.060 Uiso 1 1 calc GR . . . .
H44B H 0.419080 0.632919 0.880056 0.060 Uiso 1 1 calc GR . . . .
H44C H 0.583760 0.629492 0.907851 0.060 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 C2 1.470(2) . ?
O1 C3 1.339(2) . ?
O2 C3 1.217(2) . ?
O3 C15 1.216(3) . ?
O4 C24 1.461(2) . ?
O4 C25 1.339(2) . ?
O5 C41 1.213(3) . ?
O6 C25 1.213(2) . ?
N1 C3 1.357(3) . ?
N1 C4 1.470(2) . ?
N1 C10 1.471(2) . ?
N2 C4 1.470(3) . ?
N2 C12 1.417(3) . ?
N2 C15 1.386(3) . ?
N3 C25 1.357(3) . ?
N3 C26 1.467(3) . ?
N3 C32 1.467(2) . ?
N4 C26 1.477(2) . ?
N4 C34 1.415(3) . ?
N4 C41 1.389(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.514(3) . ?
C2 C9 1.521(3) . ?
C2 C22 1.520(3) . ?
C4 C5 1.556(3) . ?
C4 C17 1.502(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.518(3) . ?
C5 C11 1.528(3) . ?
C6 C7 1.383(3) . ?
C6 C12 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(3) . ?
C8 H8 0.9500 . ?
C8 C13 1.382(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.522(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.475(3) . ?
C16 C17 1.386(3) . ?
C16 C21 1.391(3) . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C24 1.507(3) . ?
C24 C31 1.522(3) . ?
C24 C44 1.512(3) . ?
C26 C27 1.555(3) . ?
C26 C35 1.507(3) . ?
C27 H27 1.0000 . ?
C27 C28 1.515(3) . ?
C27 C33 1.526(3) . ?
C28 C29 1.381(3) . ?
C28 C34 1.395(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.392(3) . ?
C30 H30 0.9500 . ?
C30 C43 1.381(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.528(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C42 1.383(3) . ?
C35 C36 1.388(3) . ?
C35 C40 1.378(3) . ?
C36 C37 1.385(3) . ?
C36 C41 1.486(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.388(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.393(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.394(3) . ?
C40 H40 0.9500 . ?
C42 H42 0.9500 . ?
C42 C43 1.394(3) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 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
C3 O1 C2 121.96(16) . . ?
C25 O4 C24 122.22(16) . . ?
C3 N1 C4 125.13(16) . . ?
C3 N1 C10 120.38(17) . . ?
C4 N1 C10 113.92(15) . . ?
C12 N2 C4 109.21(16) . . ?
C15 N2 C4 112.34(17) . . ?
C15 N2 C12 124.95(17) . . ?
C25 N3 C26 125.01(16) . . ?
C25 N3 C32 120.76(17) . . ?
C32 N3 C26 113.96(16) . . ?
C34 N4 C26 108.86(16) . . ?
C41 N4 C26 112.68(17) . . ?
C41 N4 C34 125.54(17) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 110.29(17) . . ?
O1 C2 C9 101.94(16) . . ?
O1 C2 C22 110.03(16) . . ?
C1 C2 C9 110.53(17) . . ?
C1 C2 C22 112.10(19) . . ?
C22 C2 C9 111.49(18) . . ?
O1 C3 N1 110.47(16) . . ?
O2 C3 O1 126.46(19) . . ?
O2 C3 N1 123.05(18) . . ?
N1 C4 N2 113.05(16) . . ?
N1 C4 C5 102.14(15) . . ?
N1 C4 C17 114.41(16) . . ?
N2 C4 C5 104.54(15) . . ?
N2 C4 C17 102.68(15) . . ?
C17 C4 C5 119.95(17) . . ?
C4 C5 H5 111.2 . . ?
C6 C5 C4 101.33(16) . . ?
C6 C5 H5 111.2 . . ?
C6 C5 C11 116.56(17) . . ?
C11 C5 C4 104.56(16) . . ?
C11 C5 H5 111.2 . . ?
C7 C6 C5 130.03(19) . . ?
C7 C6 C12 119.4(2) . . ?
C12 C6 C5 110.45(17) . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.7(2) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 119.6 . . ?
C13 C8 C7 120.9(2) . . ?
C13 C8 H8 119.6 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 111.2 . . ?
N1 C10 H10B 111.2 . . ?
N1 C10 C11 102.78(16) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C5 C11 H11A 110.9 . . ?
C5 C11 H11B 110.9 . . ?
C10 C11 C5 104.04(16) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?
C6 C12 N2 109.34(18) . . ?
C14 C12 N2 127.7(2) . . ?
C14 C12 C6 122.9(2) . . ?
C8 C13 H13 119.3 . . ?
C8 C13 C14 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C14 C13 116.8(2) . . ?
C12 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
O3 C15 N2 125.0(2) . . ?
O3 C15 C16 129.0(2) . . ?
N2 C15 C16 106.01(17) . . ?
C17 C16 C15 109.50(18) . . ?
C17 C16 C21 121.5(2) . . ?
C21 C16 C15 128.9(2) . . ?
C16 C17 C4 109.26(18) . . ?
C18 C17 C4 129.29(18) . . ?
C18 C17 C16 121.44(19) . . ?
C17 C18 H18 121.5 . . ?
C17 C18 C19 116.9(2) . . ?
C19 C18 H18 121.5 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.7(2) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.4 . . ?
C16 C21 H21 121.4 . . ?
C20 C21 C16 117.2(2) . . ?
C20 C21 H21 121.4 . . ?
C2 C22 H22A 109.5 . . ?
C2 C22 H22B 109.5 . . ?
C2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
O4 C24 C23 109.33(19) . . ?
O4 C24 C31 102.30(16) . . ?
O4 C24 C44 109.80(18) . . ?
C23 C24 C31 110.86(19) . . ?
C23 C24 C44 113.1(2) . . ?
C44 C24 C31 110.86(19) . . ?
O4 C25 N3 109.99(17) . . ?
O6 C25 O4 126.59(18) . . ?
O6 C25 N3 123.42(18) . . ?
N3 C26 N4 112.97(16) . . ?
N3 C26 C27 102.25(15) . . ?
N3 C26 C35 114.61(16) . . ?
N4 C26 C27 104.44(16) . . ?
N4 C26 C35 102.58(15) . . ?
C35 C26 C27 119.88(17) . . ?
C26 C27 H27 111.4 . . ?
C28 C27 C26 101.66(16) . . ?
C28 C27 H27 111.4 . . ?
C28 C27 C33 115.81(17) . . ?
C33 C27 C26 104.59(16) . . ?
C33 C27 H27 111.4 . . ?
C29 C28 C27 130.05(19) . . ?
C29 C28 C34 119.64(19) . . ?
C34 C28 C27 110.26(17) . . ?
C28 C29 H29 120.7 . . ?
C28 C29 C30 118.6(2) . . ?
C30 C29 H29 120.7 . . ?
C29 C30 H30 119.4 . . ?
C43 C30 C29 121.2(2) . . ?
C43 C30 H30 119.4 . . ?
C24 C31 H31A 109.5 . . ?
C24 C31 H31B 109.5 . . ?
C24 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N3 C32 H32A 111.3 . . ?
N3 C32 H32B 111.3 . . ?
N3 C32 C33 102.47(16) . . ?
H32A C32 H32B 109.2 . . ?
C33 C32 H32A 111.3 . . ?
C33 C32 H32B 111.3 . . ?
C27 C33 C32 103.69(16) . . ?
C27 C33 H33A 111.0 . . ?
C27 C33 H33B 111.0 . . ?
C32 C33 H33A 111.0 . . ?
C32 C33 H33B 111.0 . . ?
H33A C33 H33B 109.0 . . ?
C28 C34 N4 109.58(17) . . ?
C42 C34 N4 128.02(19) . . ?
C42 C34 C28 122.39(19) . . ?
C36 C35 C26 109.27(18) . . ?
C40 C35 C26 129.26(19) . . ?
C40 C35 C36 121.5(2) . . ?
C35 C36 C41 109.69(18) . . ?
C37 C36 C35 121.4(2) . . ?
C37 C36 C41 128.8(2) . . ?
C36 C37 H37 121.3 . . ?
C36 C37 C38 117.5(2) . . ?
C38 C37 H37 121.3 . . ?
C37 C38 H38 119.5 . . ?
C37 C38 C39 121.0(2) . . ?
C39 C38 H38 119.5 . . ?
C38 C39 H39 119.4 . . ?
C38 C39 C40 121.2(2) . . ?
C40 C39 H39 119.4 . . ?
C35 C40 C39 117.4(2) . . ?
C35 C40 H40 121.3 . . ?
C39 C40 H40 121.3 . . ?
O5 C41 N4 124.9(2) . . ?
O5 C41 C36 129.4(2) . . ?
N4 C41 C36 105.61(17) . . ?
C34 C42 H42 121.4 . . ?
C34 C42 C43 117.2(2) . . ?
C43 C42 H42 121.4 . . ?
C30 C43 C42 121.0(2) . . ?
C30 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C24 C44 H44A 109.5 . . ?
C24 C44 H44B 109.5 . . ?
C24 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

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
O3 C15 C16 C17 -174.8(2) . . . . ?
O3 C15 C16 C21 2.1(4) . . . . ?
N1 C4 C5 C6 96.25(17) . . . . ?
N1 C4 C5 C11 -25.29(19) . . . . ?
N1 C4 C17 C16 -124.46(18) . . . . ?
N1 C4 C17 C18 54.5(3) . . . . ?
N1 C10 C11 C5 -31.4(2) . . . . ?
N2 C4 C5 C6 -21.75(19) . . . . ?
N2 C4 C5 C11 -143.29(16) . . . . ?
N2 C4 C17 C16 -1.6(2) . . . . ?
N2 C4 C17 C18 177.4(2) . . . . ?
N2 C12 C14 C13 179.02(19) . . . . ?
N2 C15 C16 C17 3.6(2) . . . . ?
N2 C15 C16 C21 -179.5(2) . . . . ?
N3 C26 C27 C28 -96.17(17) . . . . ?
N3 C26 C27 C33 24.7(2) . . . . ?
N3 C26 C35 C36 124.00(18) . . . . ?
N3 C26 C35 C40 -55.6(3) . . . . ?
N3 C32 C33 C27 32.6(2) . . . . ?
N4 C26 C27 C28 21.75(19) . . . . ?
N4 C26 C27 C33 142.62(16) . . . . ?
N4 C26 C35 C36 1.2(2) . . . . ?
N4 C26 C35 C40 -178.4(2) . . . . ?
N4 C34 C42 C43 -179.85(19) . . . . ?
C2 O1 C3 O2 -16.4(3) . . . . ?
C2 O1 C3 N1 165.49(16) . . . . ?
C3 O1 C2 C1 70.3(2) . . . . ?
C3 O1 C2 C9 -172.33(17) . . . . ?
C3 O1 C2 C22 -53.9(2) . . . . ?
C3 N1 C4 N2 -53.9(2) . . . . ?
C3 N1 C4 C5 -165.61(18) . . . . ?
C3 N1 C4 C17 63.2(2) . . . . ?
C3 N1 C10 C11 -172.11(17) . . . . ?
C4 N1 C3 O1 -8.3(3) . . . . ?
C4 N1 C3 O2 173.56(19) . . . . ?
C4 N1 C10 C11 16.1(2) . . . . ?
C4 N2 C12 C6 -11.3(2) . . . . ?
C4 N2 C12 C14 169.1(2) . . . . ?
C4 N2 C15 O3 173.70(19) . . . . ?
C4 N2 C15 C16 -4.8(2) . . . . ?
C4 C5 C6 C7 -168.1(2) . . . . ?
C4 C5 C6 C12 16.2(2) . . . . ?
C4 C5 C11 C10 35.7(2) . . . . ?
C4 C17 C18 C19 178.6(2) . . . . ?
C5 C4 C17 C16 113.7(2) . . . . ?
C5 C4 C17 C18 -67.4(3) . . . . ?
C5 C6 C7 C8 -174.5(2) . . . . ?
C5 C6 C12 N2 -3.9(2) . . . . ?
C5 C6 C12 C14 175.74(18) . . . . ?
C6 C5 C11 C10 -75.2(2) . . . . ?
C6 C7 C8 C13 -0.3(3) . . . . ?
C6 C12 C14 C13 -0.6(3) . . . . ?
C7 C6 C12 N2 179.80(18) . . . . ?
C7 C6 C12 C14 -0.5(3) . . . . ?
C7 C8 C13 C14 -0.9(3) . . . . ?
C8 C13 C14 C12 1.3(3) . . . . ?
C10 N1 C3 O1 -179.08(17) . . . . ?
C10 N1 C3 O2 2.8(3) . . . . ?
C10 N1 C4 N2 117.46(18) . . . . ?
C10 N1 C4 C5 5.7(2) . . . . ?
C10 N1 C4 C17 -125.46(18) . . . . ?
C11 C5 C6 C7 -55.3(3) . . . . ?
C11 C5 C6 C12 128.95(19) . . . . ?
C12 N2 C4 N1 -89.17(19) . . . . ?
C12 N2 C4 C5 21.1(2) . . . . ?
C12 N2 C4 C17 147.05(16) . . . . ?
C12 N2 C15 O3 37.5(3) . . . . ?
C12 N2 C15 C16 -140.92(19) . . . . ?
C12 C6 C7 C8 0.9(3) . . . . ?
C15 N2 C4 N1 127.78(18) . . . . ?
C15 N2 C4 C5 -121.95(17) . . . . ?
C15 N2 C4 C17 4.0(2) . . . . ?
C15 N2 C12 C6 126.0(2) . . . . ?
C15 N2 C12 C14 -53.6(3) . . . . ?
C15 C16 C17 C4 -1.2(2) . . . . ?
C15 C16 C17 C18 179.81(18) . . . . ?
C15 C16 C21 C20 -177.5(2) . . . . ?
C16 C17 C18 C19 -2.6(3) . . . . ?
C17 C4 C5 C6 -136.03(18) . . . . ?
C17 C4 C5 C11 102.4(2) . . . . ?
C17 C16 C21 C20 -0.9(3) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C21 C16 C17 C4 -178.28(18) . . . . ?
C21 C16 C17 C18 2.7(3) . . . . ?
C24 O4 C25 O6 6.0(3) . . . . ?
C24 O4 C25 N3 -174.41(17) . . . . ?
C25 O4 C24 C23 61.0(3) . . . . ?
C25 O4 C24 C31 178.55(19) . . . . ?
C25 O4 C24 C44 -63.7(3) . . . . ?
C25 N3 C26 N4 58.3(3) . . . . ?
C25 N3 C26 C27 169.97(18) . . . . ?
C25 N3 C26 C35 -58.7(3) . . . . ?
C25 N3 C32 C33 167.71(18) . . . . ?
C26 N3 C25 O4 3.7(3) . . . . ?
C26 N3 C25 O6 -176.7(2) . . . . ?
C26 N3 C32 C33 -17.9(2) . . . . ?
C26 N4 C34 C28 12.4(2) . . . . ?
C26 N4 C34 C42 -168.6(2) . . . . ?
C26 N4 C41 O5 -173.6(2) . . . . ?
C26 N4 C41 C36 4.3(2) . . . . ?
C26 C27 C28 C29 167.2(2) . . . . ?
C26 C27 C28 C34 -15.5(2) . . . . ?
C26 C27 C33 C32 -36.0(2) . . . . ?
C26 C35 C36 C37 178.53(19) . . . . ?
C26 C35 C36 C41 1.3(2) . . . . ?
C26 C35 C40 C39 -178.0(2) . . . . ?
C27 C26 C35 C36 -113.8(2) . . . . ?
C27 C26 C35 C40 66.6(3) . . . . ?
C27 C28 C29 C30 176.7(2) . . . . ?
C27 C28 C34 N4 2.8(2) . . . . ?
C27 C28 C34 C42 -176.32(19) . . . . ?
C28 C27 C33 C32 74.9(2) . . . . ?
C28 C29 C30 C43 -0.9(3) . . . . ?
C28 C34 C42 C43 -1.0(3) . . . . ?
C29 C28 C34 N4 -179.58(18) . . . . ?
C29 C28 C34 C42 1.3(3) . . . . ?
C29 C30 C43 C42 1.3(3) . . . . ?
C32 N3 C25 O4 177.38(18) . . . . ?
C32 N3 C25 O6 -3.0(3) . . . . ?
C32 N3 C26 N4 -115.77(19) . . . . ?
C32 N3 C26 C27 -4.1(2) . . . . ?
C32 N3 C26 C35 127.20(19) . . . . ?
C33 C27 C28 C29 54.5(3) . . . . ?
C33 C27 C28 C34 -128.17(19) . . . . ?
C34 N4 C26 N3 88.63(19) . . . . ?
C34 N4 C26 C27 -21.7(2) . . . . ?
C34 N4 C26 C35 -147.45(16) . . . . ?
C34 N4 C41 O5 -36.8(3) . . . . ?
C34 N4 C41 C36 141.13(19) . . . . ?
C34 C28 C29 C30 -0.4(3) . . . . ?
C34 C42 C43 C30 -0.3(3) . . . . ?
C35 C26 C27 C28 135.79(18) . . . . ?
C35 C26 C27 C33 -103.3(2) . . . . ?
C35 C36 C37 C38 -0.1(3) . . . . ?
C35 C36 C41 O5 174.4(2) . . . . ?
C35 C36 C41 N4 -3.4(2) . . . . ?
C36 C35 C40 C39 2.5(3) . . . . ?
C36 C37 C38 C39 1.3(3) . . . . ?
C37 C36 C41 O5 -2.6(4) . . . . ?
C37 C36 C41 N4 179.6(2) . . . . ?
C37 C38 C39 C40 -0.7(3) . . . . ?
C38 C39 C40 C35 -1.2(3) . . . . ?
C40 C35 C36 C37 -1.9(3) . . . . ?
C40 C35 C36 C41 -179.08(18) . . . . ?
C41 N4 C26 N3 -127.42(18) . . . . ?
C41 N4 C26 C27 122.27(18) . . . . ?
C41 N4 C26 C35 -3.5(2) . . . . ?
C41 N4 C34 C28 -125.8(2) . . . . ?
C41 N4 C34 C42 53.2(3) . . . . ?
C41 C36 C37 C38 176.6(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
