# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_dd19291_0m
_database_code_depnum_ccdc_archive 'CCDC 2016180'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 Br N O2'
_chemical_formula_weight         454.31

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6941(3)
_cell_length_b                   18.5267(5)
_cell_length_c                   11.8970(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.2540(10)
_cell_angle_gamma                90
_cell_volume                     2102.57(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7725
_cell_measurement_theta_min      4.803
_cell_measurement_theta_max      50.855

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.977
_shelx_estimated_absorpt_T_min   0.730
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4874
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22758
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4116
_reflns_number_gt                3161
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0376P)²+0.8706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4116
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Br1 Br 0.48605(3) 0.36471(2) 0.33668(2) 0.06796(13) Uani 1 1 d . . . . .
O1 O 0.63503(18) 0.47885(9) 0.42242(13) 0.0557(4) Uani 1 1 d . . . . .
O2 O 0.79766(17) 0.50773(9) 0.61252(13) 0.0543(4) Uani 1 1 d . . . . .
N1 N 0.3577(3) 0.45256(13) 0.0525(2) 0.0716(7) Uani 1 1 d . . . . .
C1 C 0.5484(3) 0.45956(13) 0.3262(2) 0.0485(6) Uani 1 1 d . . . . .
C2 C 0.5146(2) 0.50029(12) 0.23366(19) 0.0456(5) Uani 1 1 d . . . . .
C3 C 0.5680(3) 0.57704(12) 0.22872(19) 0.0470(5) Uani 1 1 d . . . . .
H3 H 0.6200 0.5797 0.1653 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6698(2) 0.59405(12) 0.33799(19) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.7022(2) 0.54636(12) 0.42176(19) 0.0463(5) Uani 1 1 d . . . . .
C6 C 0.8133(3) 0.55125(12) 0.52166(19) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.9330(3) 0.58798(13) 0.5428(2) 0.0499(6) Uani 1 1 d . . . . .
H7 H 0.9652 0.6205 0.4937 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0027(2) 0.56839(13) 0.6544(2) 0.0474(6) Uani 1 1 d . . . . .
C9 C 1.1290(3) 0.58660(16) 0.7264(3) 0.0637(7) Uani 1 1 d . . . . .
H9 H 1.1903 0.6200 0.7038 0.076 Uiso 1 1 calc R U . . .
C10 C 1.1593(3) 0.55325(18) 0.8319(2) 0.0698(8) Uani 1 1 d . . . . .
H10 H 1.2423 0.5646 0.8809 0.084 Uiso 1 1 calc R U . . .
C11 C 1.0698(3) 0.50384(18) 0.8661(2) 0.0705(8) Uani 1 1 d . . . . .
H11 H 1.0947 0.4821 0.9373 0.085 Uiso 1 1 calc R U . . .
C12 C 0.9452(3) 0.48562(17) 0.7989(2) 0.0665(7) Uani 1 1 d . . . . .
H12 H 0.8838 0.4528 0.8228 0.080 Uiso 1 1 calc R U . . .
C13 C 0.9162(3) 0.51888(13) 0.69338(19) 0.0490(6) Uani 1 1 d . . . . .
C14 C 0.4264(3) 0.47241(13) 0.1344(2) 0.0506(6) Uani 1 1 d . . . . .
C15 C 0.4449(3) 0.62928(13) 0.2029(2) 0.0545(6) Uani 1 1 d . . . . .
C16 C 0.4090(4) 0.65686(17) 0.0938(3) 0.0816(9) Uani 1 1 d . . . . .
H16 H 0.4644 0.6467 0.0395 0.098 Uiso 1 1 calc R U . . .
C17 C 0.2908(5) 0.6996(2) 0.0650(4) 0.1107(14) Uani 1 1 d . . . . .
H17 H 0.2657 0.7174 -0.0089 0.133 Uiso 1 1 calc R U . . .
C18 C 0.2128(5) 0.7151(2) 0.1443(5) 0.1086(14) Uani 1 1 d . . . . .
H18 H 0.1338 0.7440 0.1245 0.130 Uiso 1 1 calc R U . . .
C19 C 0.2461(4) 0.6896(2) 0.2528(4) 0.0998(12) Uani 1 1 d . . . . .
H19 H 0.1911 0.7012 0.3067 0.120 Uiso 1 1 calc R U . . .
C20 C 0.3645(3) 0.64534(18) 0.2823(3) 0.0780(9) Uani 1 1 d . . . . .
H20 H 0.3879 0.6270 0.3561 0.094 Uiso 1 1 calc R U . . .
C21 C 0.7348(2) 0.66679(12) 0.34279(19) 0.0450(5) Uani 1 1 d . . . . .
C22 C 0.8133(3) 0.68852(15) 0.2624(2) 0.0646(7) Uani 1 1 d . . . . .
H22 H 0.8271 0.6569 0.2047 0.078 Uiso 1 1 calc R U . . .
C23 C 0.8711(3) 0.75655(17) 0.2672(3) 0.0802(9) Uani 1 1 d . . . . .
H23 H 0.9234 0.7704 0.2125 0.096 Uiso 1 1 calc R U . . .
C24 C 0.8528(3) 0.80372(16) 0.3506(3) 0.0755(9) Uani 1 1 d . . . . .
H24 H 0.8932 0.8494 0.3534 0.091 Uiso 1 1 calc R U . . .
C25 C 0.7754(3) 0.78399(14) 0.4300(3) 0.0700(8) Uani 1 1 d . . . . .
H25 H 0.7625 0.8162 0.4872 0.084 Uiso 1 1 calc R U . . .
C26 C 0.7157(3) 0.71600(14) 0.4259(2) 0.0593(7) Uani 1 1 d . . . . .
H26 H 0.6617 0.7032 0.4800 0.071 Uiso 1 1 calc R U . . .


_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
Br1 C1 1.870(2) . ?
O1 C1 1.342(3) . ?
O1 C5 1.411(3) . ?
O2 C13 1.377(3) . ?
O2 C6 1.378(3) . ?
N1 C14 1.139(3) . ?
C1 C2 1.327(3) . ?
C2 C14 1.425(3) . ?
C2 C3 1.518(3) . ?
C3 C4 1.519(3) . ?
C3 C15 1.525(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.327(3) . ?
C4 C21 1.484(3) . ?
C5 C6 1.458(3) . ?
C6 C7 1.330(3) . ?
C7 C8 1.426(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.378(3) . ?
C8 C9 1.404(3) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C15 C20 1.361(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.385(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.341(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.382(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.376(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.358(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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 C5 116.79(17) . . ?
C13 O2 C6 105.41(18) . . ?
C2 C1 O1 125.5(2) . . ?
C2 C1 Br1 123.69(18) . . ?
O1 C1 Br1 110.74(16) . . ?
C1 C2 C14 120.3(2) . . ?
C1 C2 C3 121.9(2) . . ?
C14 C2 C3 117.76(19) . . ?
C2 C3 C4 109.60(18) . . ?
C2 C3 C15 110.0(2) . . ?
C4 C3 C15 114.01(19) . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C15 C3 H3 107.7 . . ?
C5 C4 C21 122.3(2) . . ?
C5 C4 C3 122.4(2) . . ?
C21 C4 C3 115.34(19) . . ?
C4 C5 O1 123.2(2) . . ?
C4 C5 C6 127.8(2) . . ?
O1 C5 C6 108.98(18) . . ?
C7 C6 O2 111.4(2) . . ?
C7 C6 C5 132.8(2) . . ?
O2 C6 C5 115.8(2) . . ?
C6 C7 C8 107.4(2) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
C13 C8 C9 118.1(2) . . ?
C13 C8 C7 105.5(2) . . ?
C9 C8 C7 136.4(3) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 115.9(3) . . ?
C11 C12 H12 122.0 . . ?
C13 C12 H12 122.0 . . ?
O2 C13 C8 110.3(2) . . ?
O2 C13 C12 125.3(2) . . ?
C8 C13 C12 124.4(2) . . ?
N1 C14 C2 177.0(3) . . ?
C20 C15 C16 119.5(3) . . ?
C20 C15 C3 121.6(2) . . ?
C16 C15 C3 118.8(3) . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.7(4) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 119.1(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C15 C20 C19 119.8(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C26 C21 C22 117.6(2) . . ?
C26 C21 C4 121.1(2) . . ?
C22 C21 C4 121.3(2) . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 121.0(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 121.1(3) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?

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
C5 O1 C1 C2 -4.2(4) . . . . ?
C5 O1 C1 Br1 173.27(16) . . . . ?
O1 C1 C2 C14 177.0(2) . . . . ?
Br1 C1 C2 C14 -0.2(3) . . . . ?
O1 C1 C2 C3 -2.6(4) . . . . ?
Br1 C1 C2 C3 -179.77(18) . . . . ?
C1 C2 C3 C4 4.6(3) . . . . ?
C14 C2 C3 C4 -174.9(2) . . . . ?
C1 C2 C3 C15 -121.5(3) . . . . ?
C14 C2 C3 C15 59.0(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C15 C3 C4 C5 123.7(3) . . . . ?
C2 C3 C4 C21 177.7(2) . . . . ?
C15 C3 C4 C21 -58.5(3) . . . . ?
C21 C4 C5 O1 175.6(2) . . . . ?
C3 C4 C5 O1 -6.7(4) . . . . ?
C21 C4 C5 C6 -8.3(4) . . . . ?
C3 C4 C5 C6 169.3(2) . . . . ?
C1 O1 C5 C4 9.0(3) . . . . ?
C1 O1 C5 C6 -167.7(2) . . . . ?
C13 O2 C6 C7 -0.2(3) . . . . ?
C13 O2 C6 C5 177.3(2) . . . . ?
C4 C5 C6 C7 -23.3(4) . . . . ?
O1 C5 C6 C7 153.2(3) . . . . ?
C4 C5 C6 O2 159.8(2) . . . . ?
O1 C5 C6 O2 -23.7(3) . . . . ?
O2 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C8 -177.1(2) . . . . ?
C6 C7 C8 C13 0.3(3) . . . . ?
C6 C7 C8 C9 180.0(3) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C6 O2 C13 C8 0.5(3) . . . . ?
C6 O2 C13 C12 -179.7(2) . . . . ?
C9 C8 C13 O2 179.8(2) . . . . ?
C7 C8 C13 O2 -0.5(3) . . . . ?
C9 C8 C13 C12 -0.1(4) . . . . ?
C7 C8 C13 C12 179.6(2) . . . . ?
C11 C12 C13 O2 179.4(2) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C2 C3 C15 C20 72.3(3) . . . . ?
C4 C3 C15 C20 -51.2(3) . . . . ?
C2 C3 C15 C16 -103.2(3) . . . . ?
C4 C3 C15 C16 133.2(3) . . . . ?
C20 C15 C16 C17 -1.0(5) . . . . ?
C3 C15 C16 C17 174.6(3) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C3 C15 C20 C19 -175.4(3) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C5 C4 C21 C26 -62.9(3) . . . . ?
C3 C4 C21 C26 119.3(3) . . . . ?
C5 C4 C21 C22 119.0(3) . . . . ?
C3 C4 C21 C22 -58.8(3) . . . . ?
C26 C21 C22 C23 0.9(4) . . . . ?
C4 C21 C22 C23 179.1(3) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 -0.6(5) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C22 C21 C26 C25 -1.4(4) . . . . ?
C4 C21 C26 C25 -179.6(2) . . . . ?
C24 C25 C26 C21 0.9(5) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd19401_0m
_database_code_depnum_ccdc_archive 'CCDC 2016181'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H30 N2 O2'
_chemical_formula_weight         618.70

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'

_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                   9.9622(7)
_cell_length_b                   10.2570(7)
_cell_length_c                   18.2695(11)
_cell_angle_alpha                90.165(2)
_cell_angle_beta                 93.058(2)
_cell_angle_gamma                93.993(2)
_cell_volume                     1859.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8614
_cell_measurement_theta_min      4.551
_cell_measurement_theta_max      53.932

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27147
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6914
_reflns_number_gt                4516
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1046P)²+0.1587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6914
_refine_ls_number_parameters     482
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1938
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 6 0 ' '
2 0.102 0.208 0.160 9 0 ' '
3 0.500 1.000 1.000 290 30 ' '
4 0.898 0.792 0.840 9 0 ' '
_platon_squeeze_details          
;
;


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
N1 N 1.0595(2) 0.7327(2) 0.52980(12) 0.0750(6) Uani 1 1 d . . . . .
N2 N 0.8262(2) 0.4094(2) 0.82126(11) 0.0782(6) Uani 1 1 d . . . . .
O1 O 0.66124(14) 0.44994(14) 0.48552(7) 0.0528(4) Uani 1 1 d . . . . .
O2 O 0.4951(7) 0.2508(7) 0.4437(3) 0.064(2) Uani 0.6 1 d . U P A 1
C1 C 0.4041(8) 0.1727(9) 0.4072(4) 0.082(4) Uani 0.5 1 d G U P A 1
C2 C 0.3166(8) 0.0822(8) 0.4403(3) 0.098(3) Uani 0.5 1 d G U P A 1
H2 H 0.3228 0.0716 0.4909 0.117 Uiso 0.5 1 calc R U P A 1
C3 C 0.2199(6) 0.0076(6) 0.3978(4) 0.083(2) Uani 0.5 1 d G U P A 1
H3 H 0.1614 -0.0530 0.4199 0.100 Uiso 0.5 1 calc R U P A 1
C4 C 0.2107(5) 0.0234(6) 0.3222(3) 0.072(2) Uani 0.5 1 d G U P A 1
H4 H 0.1459 -0.0265 0.2937 0.087 Uiso 0.5 1 calc R U P A 1
C5 C 0.2981(7) 0.1139(7) 0.2891(3) 0.080(2) Uani 0.5 1 d G U P A 1
H5 H 0.2919 0.1245 0.2385 0.096 Uiso 0.5 1 calc R U P A 1
C6 C 0.3948(7) 0.1885(7) 0.3316(4) 0.047(2) Uani 0.5 1 d G U P A 1
C7 C 0.5017(10) 0.2954(10) 0.3238(4) 0.051(2) Uani 0.8 1 d . U P A 1
H7 H 0.5279 0.3353 0.2807 0.061 Uiso 0.8 1 calc R U P A 1
O2' O 0.5073(17) 0.2948(17) 0.3281(8) 0.085(5) Uani 0.4 1 d D U P A 2
C1' C 0.3896(7) 0.1622(8) 0.4033(4) 0.049(3) Uani 0.5 1 d DG U P A 2
C2' C 0.2897(7) 0.0638(7) 0.4143(3) 0.087(2) Uani 0.5 1 d G U P A 2
H2' H 0.2733 0.0357 0.4615 0.105 Uiso 0.5 1 calc R U P A 2
C3' C 0.2144(5) 0.0075(5) 0.3547(4) 0.081(2) Uani 0.5 1 d G U P A 2
H3' H 0.1476 -0.0584 0.3620 0.097 Uiso 0.5 1 calc R U P A 2
C4' C 0.2390(6) 0.0495(6) 0.2841(3) 0.082(2) Uani 0.5 1 d G U P A 2
H4' H 0.1886 0.0118 0.2442 0.099 Uiso 0.5 1 calc R U P A 2
C5' C 0.3389(7) 0.1479(8) 0.2731(3) 0.089(3) Uani 0.5 1 d G U P A 2
H5' H 0.3553 0.1760 0.2258 0.106 Uiso 0.5 1 calc R U P A 2
C6' C 0.4142(8) 0.2043(8) 0.3327(4) 0.077(3) Uani 0.5 1 d G U P A 2
C7' C 0.4852(19) 0.2411(19) 0.4417(9) 0.026(5) Uani 0.2 1 d D U P A 2
H7' H 0.5019 0.2401 0.4923 0.031 Uiso 0.2 1 calc R U P A 2
C8 C 0.5533(2) 0.3228(2) 0.39373(15) 0.0537(6) Uani 1 1 d D . . . .
C9 C 0.65693(19) 0.42630(19) 0.41026(11) 0.0452(5) Uani 1 1 d . . . . .
C10 C 0.7365(2) 0.49313(19) 0.36554(10) 0.0457(5) Uani 1 1 d . . . . .
C11 C 0.82598(19) 0.60979(18) 0.39429(11) 0.0446(5) Uani 1 1 d . . . . .
H11 H 0.9133 0.6065 0.3723 0.054 Uiso 1 1 calc R U . . .
C12 C 0.8501(2) 0.59853(19) 0.47676(11) 0.0457(5) Uani 1 1 d . . . . .
C13 C 0.7687(2) 0.52180(19) 0.51740(11) 0.0465(5) Uani 1 1 d . . . . .
C14 C 0.7821(2) 0.4968(2) 0.59655(11) 0.0496(5) Uani 1 1 d . . . . .
C15 C 0.8278(2) 0.5920(2) 0.64722(12) 0.0570(6) Uani 1 1 d . . . . .
H15 H 0.8492 0.6768 0.6316 0.068 Uiso 1 1 calc R U . . .
C16 C 0.8421(2) 0.5628(3) 0.72070(12) 0.0651(6) Uani 1 1 d . . . . .
H16 H 0.8728 0.6283 0.7540 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8118(3) 0.4384(3) 0.74547(12) 0.0647(6) Uani 1 1 d . . . . .
C18 C 0.7647(3) 0.3421(2) 0.69510(12) 0.0680(7) Uani 1 1 d . . . . .
H18 H 0.7430 0.2576 0.7111 0.082 Uiso 1 1 calc R U . . .
C19 C 0.7498(2) 0.3708(2) 0.62186(12) 0.0617(6) Uani 1 1 d . . . . .
H19 H 0.7179 0.3054 0.5887 0.074 Uiso 1 1 calc R U . . .
C20 C 0.7491(2) 0.4521(2) 0.28823(12) 0.0580(6) Uani 1 1 d . . . . .
C21 C 0.8029(3) 0.3344(3) 0.27414(15) 0.0818(8) Uani 1 1 d . . . . .
H21 H 0.8292 0.2814 0.3128 0.098 Uiso 1 1 calc R U . . .
C22 C 0.8176(4) 0.2956(5) 0.2030(2) 0.1196(14) Uani 1 1 d . . . . .
H22 H 0.8541 0.2165 0.1939 0.144 Uiso 1 1 calc R U . . .
C23 C 0.7792(5) 0.3723(6) 0.1454(2) 0.1301(18) Uani 1 1 d . . . . .
H23 H 0.7881 0.3451 0.0974 0.156 Uiso 1 1 calc R U . . .
C24 C 0.7286(5) 0.4866(5) 0.15904(18) 0.1300(16) Uani 1 1 d . . . . .
H24 H 0.7034 0.5389 0.1199 0.156 Uiso 1 1 calc R U . . .
C25 C 0.7127(4) 0.5294(3) 0.23025(14) 0.0955(10) Uani 1 1 d . . . . .
H25 H 0.6779 0.6096 0.2385 0.115 Uiso 1 1 calc R U . . .
C26 C 0.7719(2) 0.74145(19) 0.37534(11) 0.0465(5) Uani 1 1 d . . . . .
C27 C 0.6366(2) 0.7604(2) 0.36941(13) 0.0616(6) Uani 1 1 d . . . . .
H27 H 0.5742 0.6896 0.3743 0.074 Uiso 1 1 calc R U . . .
C28 C 0.5919(3) 0.8827(3) 0.35627(17) 0.0795(8) Uani 1 1 d . . . . .
H28 H 0.5000 0.8941 0.3521 0.095 Uiso 1 1 calc R U . . .
C29 C 0.6828(3) 0.9870(3) 0.34933(18) 0.0884(9) Uani 1 1 d . . . . .
H29 H 0.6526 1.0693 0.3399 0.106 Uiso 1 1 calc R U . . .
C30 C 0.8175(3) 0.9714(3) 0.35615(19) 0.0923(10) Uani 1 1 d . . . . .
H30 H 0.8793 1.0432 0.3530 0.111 Uiso 1 1 calc R U . . .
C31 C 0.8614(2) 0.8490(2) 0.36766(15) 0.0712(7) Uani 1 1 d . . . . .
H31 H 0.9534 0.8381 0.3704 0.085 Uiso 1 1 calc R U . . .
C32 C 0.9662(2) 0.6716(2) 0.50873(12) 0.0521(5) Uani 1 1 d . . . . .
C33 C 0.7871(3) 0.5021(3) 0.87257(13) 0.0768(8) Uani 1 1 d . . . . .
C34 C 0.6607(3) 0.5475(4) 0.86598(18) 0.1120(12) Uani 1 1 d . . . . .
H34 H 0.5992 0.5161 0.8289 0.134 Uiso 1 1 calc R U . . .
C35 C 0.6256(4) 0.6416(5) 0.9157(2) 0.1433(17) Uani 1 1 d . . . . .
H35 H 0.5411 0.6748 0.9106 0.172 Uiso 1 1 calc R U . . .
C36 C 0.7129(5) 0.6850(5) 0.9711(2) 0.1363(16) Uani 1 1 d . . . . .
H36 H 0.6877 0.7455 1.0049 0.164 Uiso 1 1 calc R U . . .
C37 C 0.8369(5) 0.6397(4) 0.97699(19) 0.1207(13) Uani 1 1 d . . . . .
H37 H 0.8975 0.6703 1.0147 0.145 Uiso 1 1 calc R U . . .
C38 C 0.8744(3) 0.5498(4) 0.92847(16) 0.0939(10) Uani 1 1 d . . . . .
H38 H 0.9606 0.5202 0.9333 0.113 Uiso 1 1 calc R U . . .
C39 C 0.8840(3) 0.2948(3) 0.84489(13) 0.0722(7) Uani 1 1 d . . . . .
C40 C 0.8378(3) 0.2273(4) 0.90478(17) 0.1003(10) Uani 1 1 d . . . . .
H40 H 0.7687 0.2581 0.9308 0.120 Uiso 1 1 calc R U . . .
C41 C 0.8957(5) 0.1120(5) 0.9260(2) 0.1259(14) Uani 1 1 d . . . . .
H41 H 0.8627 0.0645 0.9653 0.151 Uiso 1 1 calc R U . . .
C42 C 1.0007(5) 0.0684(4) 0.8895(3) 0.1272(14) Uani 1 1 d . . . . .
H42 H 1.0405 -0.0068 0.9050 0.153 Uiso 1 1 calc R U . . .
C43 C 1.0458(4) 0.1340(4) 0.8317(2) 0.1101(11) Uani 1 1 d . . . . .
H43 H 1.1155 0.1031 0.8062 0.132 Uiso 1 1 calc R U . . .
C44 C 0.9891(3) 0.2481(3) 0.80972(16) 0.0873(9) Uani 1 1 d . . . . .
H44 H 1.0231 0.2940 0.7701 0.105 Uiso 1 1 calc R U . . .


_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
N1 C32 1.133(3) . ?
N2 C39 1.403(3) . ?
N2 C17 1.419(3) . ?
N2 C33 1.422(4) . ?
O1 C13 1.360(2) . ?
O1 C9 1.393(2) . ?
O2 C8 1.310(6) . ?
O2 C1 1.318(6) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.487(11) . ?
C7 C8 1.372(9) . ?
C7 H7 0.9300 . ?
O2' C6' 1.272(17) . ?
O2' C8 1.285(14) . ?
C1' C7' 1.368(17) . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C2' C3' 1.3900 . ?
C2' H2' 0.9300 . ?
C3' C4' 1.3900 . ?
C3' H3' 0.9300 . ?
C4' C5' 1.3900 . ?
C4' H4' 0.9300 . ?
C5' C6' 1.3900 . ?
C5' H5' 0.9300 . ?
C7' C8 1.385(16) . ?
C7' H7' 0.9300 . ?
C8 C9 1.448(3) . ?
C9 C10 1.328(3) . ?
C10 C20 1.487(3) . ?
C10 C11 1.516(3) . ?
C11 C12 1.519(3) . ?
C11 C26 1.523(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.345(3) . ?
C12 C32 1.430(3) . ?
C13 C14 1.470(3) . ?
C14 C15 1.380(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.373(4) . ?
C20 C21 1.384(4) . ?
C21 C22 1.377(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.335(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.393(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.374(3) . ?
C26 C31 1.381(3) . ?
C27 C28 1.377(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.362(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.362(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.371(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C33 C34 1.372(4) . ?
C33 C38 1.372(4) . ?
C34 C35 1.398(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.352(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.348(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.362(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.371(4) . ?
C39 C40 1.379(4) . ?
C40 C41 1.398(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.369(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.336(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.386(4) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?

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
C39 N2 C17 120.6(2) . . ?
C39 N2 C33 120.9(2) . . ?
C17 N2 C33 118.4(2) . . ?
C13 O1 C9 119.12(15) . . ?
C8 O2 C1 105.3(5) . . ?
O2 C1 C2 123.9(6) . . ?
O2 C1 C6 116.1(6) . . ?
C2 C1 C6 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 140.1(6) . . ?
C1 C6 C7 99.9(6) . . ?
C8 C7 C6 105.4(7) . . ?
C8 C7 H7 127.3 . . ?
C6 C7 H7 127.3 . . ?
C6' O2' C8 107.2(12) . . ?
C7' C1' C2' 140.7(8) . . ?
C7' C1' C6' 99.3(8) . . ?
C2' C1' C6' 120.0 . . ?
C3' C2' C1' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C3' C4' C5' 120.0 . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
O2' C6' C5' 124.5(8) . . ?
O2' C6' C1' 115.5(8) . . ?
C5' C6' C1' 120.0 . . ?
C1' C7' C8 109.6(12) . . ?
C1' C7' H7' 125.2 . . ?
C8 C7' H7' 125.2 . . ?
O2 C8 C7 113.4(5) . . ?
O2' C8 C7' 108.5(10) . . ?
O2' C8 C9 122.8(8) . . ?
O2 C8 C9 123.8(3) . . ?
C7 C8 C9 122.7(5) . . ?
C7' C8 C9 128.7(7) . . ?
C10 C9 O1 122.60(18) . . ?
C10 C9 C8 129.6(2) . . ?
O1 C9 C8 107.77(18) . . ?
C9 C10 C20 122.08(18) . . ?
C9 C10 C11 120.03(18) . . ?
C20 C10 C11 117.74(17) . . ?
C10 C11 C12 109.57(15) . . ?
C10 C11 C26 114.18(16) . . ?
C12 C11 C26 110.04(16) . . ?
C10 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
C26 C11 H11 107.6 . . ?
C13 C12 C32 121.67(19) . . ?
C13 C12 C11 121.93(17) . . ?
C32 C12 C11 116.38(17) . . ?
C12 C13 O1 120.69(18) . . ?
C12 C13 C14 128.13(18) . . ?
O1 C13 C14 111.10(17) . . ?
C15 C14 C19 118.2(2) . . ?
C15 C14 C13 122.94(19) . . ?
C19 C14 C13 118.84(19) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.8(2) . . ?
C16 C17 N2 120.6(2) . . ?
C18 C17 N2 120.6(2) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C25 C20 C21 118.9(2) . . ?
C25 C20 C10 122.0(2) . . ?
C21 C20 C10 119.1(2) . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 121.8(4) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C20 C25 C24 119.4(4) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C31 117.8(2) . . ?
C27 C26 C11 122.80(18) . . ?
C31 C26 C11 119.31(18) . . ?
C26 C27 C28 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 119.8(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.5(2) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C31 119.4(3) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C26 121.5(2) . . ?
C30 C31 H31 119.3 . . ?
C26 C31 H31 119.3 . . ?
N1 C32 C12 175.6(2) . . ?
C34 C33 C38 118.7(3) . . ?
C34 C33 N2 120.1(3) . . ?
C38 C33 N2 121.3(3) . . ?
C33 C34 C35 119.2(3) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C36 C35 C34 120.8(4) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C37 C36 C35 119.4(4) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C38 120.9(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C37 C38 C33 121.0(3) . . ?
C37 C38 H38 119.5 . . ?
C33 C38 H38 119.5 . . ?
C44 C39 C40 118.3(3) . . ?
C44 C39 N2 120.9(2) . . ?
C40 C39 N2 120.9(3) . . ?
C39 C40 C41 119.4(4) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C42 C41 C40 120.6(4) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C43 C42 C41 120.0(4) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.1(4) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 121.5(3) . . ?
C39 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?

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 O2 C1 C2 -178.1(5) . . . . ?
C8 O2 C1 C6 -0.8(9) . . . . ?
O2 C1 C2 C3 177.3(10) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 -176.8(11) . . . . ?
O2 C1 C6 C5 -177.5(9) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
O2 C1 C6 C7 0.5(7) . . . . ?
C2 C1 C6 C7 177.9(7) . . . . ?
C5 C6 C7 C8 177.2(7) . . . . ?
C1 C6 C7 C8 0.0(7) . . . . ?
C7' C1' C2' C3' -178.8(18) . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C8 O2' C6' C5' 179.5(7) . . . . ?
C8 O2' C6' C1' -0.4(16) . . . . ?
C4' C5' C6' O2' -179.9(13) . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C7' C1' C6' O2' -0.9(14) . . . . ?
C2' C1' C6' O2' 179.9(12) . . . . ?
C7' C1' C6' C5' 179.2(12) . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?
C2' C1' C7' C8 -179.4(8) . . . . ?
C6' C1' C7' C8 1.7(15) . . . . ?
C6' O2' C8 O2 1.4(16) . . . . ?
C6' O2' C8 C7 -90(45) . . . . ?
C6' O2' C8 C7' 1.5(17) . . . . ?
C6' O2' C8 C9 -177.1(8) . . . . ?
C1 O2 C8 O2' -1.0(12) . . . . ?
C1 O2 C8 C7 0.7(9) . . . . ?
C1 O2 C8 C7' -2(14) . . . . ?
C1 O2 C8 C9 177.5(6) . . . . ?
C6 C7 C8 O2' 89(45) . . . . ?
C6 C7 C8 O2 -0.5(9) . . . . ?
C6 C7 C8 C7' -0.2(12) . . . . ?
C6 C7 C8 C9 -177.3(5) . . . . ?
C1' C7' C8 O2' -2.1(19) . . . . ?
C1' C7' C8 O2 177(16) . . . . ?
C1' C7' C8 C7 -0.5(17) . . . . ?
C1' C7' C8 C9 176.4(7) . . . . ?
C13 O1 C9 C10 -15.2(3) . . . . ?
C13 O1 C9 C8 165.68(17) . . . . ?
O2' C8 C9 C10 -12.3(10) . . . . ?
O2 C8 C9 C10 169.4(5) . . . . ?
C7 C8 C9 C10 -14.2(6) . . . . ?
C7' C8 C9 C10 169.4(12) . . . . ?
O2' C8 C9 O1 166.8(10) . . . . ?
O2 C8 C9 O1 -11.6(5) . . . . ?
C7 C8 C9 O1 164.9(5) . . . . ?
C7' C8 C9 O1 -11.5(12) . . . . ?
O1 C9 C10 C20 168.70(19) . . . . ?
C8 C9 C10 C20 -12.4(4) . . . . ?
O1 C9 C10 C11 -6.8(3) . . . . ?
C8 C9 C10 C11 172.1(2) . . . . ?
C9 C10 C11 C12 22.6(3) . . . . ?
C20 C10 C11 C12 -153.10(18) . . . . ?
C9 C10 C11 C26 -101.3(2) . . . . ?
C20 C10 C11 C26 83.0(2) . . . . ?
C10 C11 C12 C13 -19.9(3) . . . . ?
C26 C11 C12 C13 106.4(2) . . . . ?
C10 C11 C12 C32 158.67(17) . . . . ?
C26 C11 C12 C32 -75.0(2) . . . . ?
C32 C12 C13 O1 -177.89(18) . . . . ?
C11 C12 C13 O1 0.6(3) . . . . ?
C32 C12 C13 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 177.24(19) . . . . ?
C9 O1 C13 C12 18.2(3) . . . . ?
C9 O1 C13 C14 -158.99(17) . . . . ?
C12 C13 C14 C15 37.5(3) . . . . ?
O1 C13 C14 C15 -145.6(2) . . . . ?
C12 C13 C14 C19 -141.2(2) . . . . ?
O1 C13 C14 C19 35.7(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C13 C14 C15 C16 -178.2(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C15 C16 C17 N2 -179.7(2) . . . . ?
C39 N2 C17 C16 -137.0(3) . . . . ?
C33 N2 C17 C16 39.9(4) . . . . ?
C39 N2 C17 C18 44.1(4) . . . . ?
C33 N2 C17 C18 -139.0(3) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
N2 C17 C18 C19 179.5(2) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C15 C14 C19 C18 -0.7(3) . . . . ?
C13 C14 C19 C18 178.1(2) . . . . ?
C9 C10 C20 C25 118.0(3) . . . . ?
C11 C10 C20 C25 -66.3(3) . . . . ?
C9 C10 C20 C21 -64.1(3) . . . . ?
C11 C10 C20 C21 111.6(2) . . . . ?
C25 C20 C21 C22 -0.9(4) . . . . ?
C10 C20 C21 C22 -178.8(2) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 0.9(6) . . . . ?
C22 C23 C24 C25 -0.6(6) . . . . ?
C21 C20 C25 C24 1.2(4) . . . . ?
C10 C20 C25 C24 179.1(3) . . . . ?
C23 C24 C25 C20 -0.4(6) . . . . ?
C10 C11 C26 C27 32.7(3) . . . . ?
C12 C11 C26 C27 -91.0(2) . . . . ?
C10 C11 C26 C31 -151.1(2) . . . . ?
C12 C11 C26 C31 85.3(2) . . . . ?
C31 C26 C27 C28 0.0(4) . . . . ?
C11 C26 C27 C28 176.3(2) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C28 C29 C30 C31 2.2(5) . . . . ?
C29 C30 C31 C26 -2.5(5) . . . . ?
C27 C26 C31 C30 1.4(4) . . . . ?
C11 C26 C31 C30 -175.0(3) . . . . ?
C39 N2 C33 C34 -130.0(3) . . . . ?
C17 N2 C33 C34 53.1(4) . . . . ?
C39 N2 C33 C38 51.2(4) . . . . ?
C17 N2 C33 C38 -125.7(3) . . . . ?
C38 C33 C34 C35 0.7(5) . . . . ?
N2 C33 C34 C35 -178.1(3) . . . . ?
C33 C34 C35 C36 -2.0(7) . . . . ?
C34 C35 C36 C37 2.1(8) . . . . ?
C35 C36 C37 C38 -0.9(7) . . . . ?
C36 C37 C38 C33 -0.4(6) . . . . ?
C34 C33 C38 C37 0.5(5) . . . . ?
N2 C33 C38 C37 179.3(3) . . . . ?
C17 N2 C39 C44 36.9(4) . . . . ?
C33 N2 C39 C44 -139.9(3) . . . . ?
C17 N2 C39 C40 -144.0(3) . . . . ?
C33 N2 C39 C40 39.2(4) . . . . ?
C44 C39 C40 C41 -2.2(5) . . . . ?
N2 C39 C40 C41 178.7(3) . . . . ?
C39 C40 C41 C42 2.3(6) . . . . ?
C40 C41 C42 C43 -2.1(7) . . . . ?
C41 C42 C43 C44 1.7(6) . . . . ?
C40 C39 C44 C43 1.9(4) . . . . ?
N2 C39 C44 C43 -179.0(3) . . . . ?
C42 C43 C44 C39 -1.7(5) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

