# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Op
_database_code_depnum_ccdc_archive 'CCDC 1919853'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.0547(13)
_cell_length_b                   19.198(3)
_cell_length_c                   8.7595(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1690.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            10996
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.774
_diffrn_reflns_theta_max         27.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.856
_reflns_number_total             3330
_reflns_number_gt                2997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_max     0.681
_reflns_Friedel_fraction_full    0.708

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0507P)²+0.2444P] 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_abs_structure_details 
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3330
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.7372(4) 0.99222(16) 0.9107(4) 0.0703(8) Uani 1 1 d . . . . .
H1A H 0.730896 0.968655 1.007139 0.106 Uiso 1 1 calc R U . . .
H1B H 0.731415 1.041601 0.926706 0.106 Uiso 1 1 calc R U . . .
H1C H 0.820679 0.981195 0.863427 0.106 Uiso 1 1 calc R U . . .
C2 C 0.6174(2) 0.90113(12) 0.7873(3) 0.0465(5) Uani 1 1 d . . . . .
C3 C 0.7023(2) 0.84990(13) 0.8399(3) 0.0488(5) Uani 1 1 d . . . . .
H3 H 0.776025 0.861597 0.898682 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6766(2) 0.78108(13) 0.8042(3) 0.0483(5) Uani 1 1 d . . . . .
H4 H 0.733266 0.746739 0.841321 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5697(2) 0.76170(11) 0.7153(2) 0.0408(4) Uani 1 1 d . . . . .
C6 C 0.4857(2) 0.81430(12) 0.6630(3) 0.0466(5) Uani 1 1 d . . . . .
H6 H 0.412647 0.802920 0.602929 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5097(3) 0.88277(12) 0.6992(3) 0.0495(5) Uani 1 1 d . . . . .
H7 H 0.452404 0.917167 0.663732 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5422(2) 0.68841(11) 0.6807(3) 0.0423(5) Uani 1 1 d . . . . .
C9 C 0.6012(3) 0.62795(13) 0.7460(3) 0.0572(6) Uani 1 1 d . . . . .
H9 H 0.668910 0.626420 0.818193 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5384(3) 0.57337(12) 0.6814(3) 0.0557(6) Uani 1 1 d . . . . .
H10 H 0.553588 0.526451 0.701220 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3527(3) 0.56365(12) 0.4971(3) 0.0479(5) Uani 1 1 d . . . . .
C12 C 0.2591(2) 0.60854(12) 0.4066(3) 0.0449(5) Uani 1 1 d . . . . .
H12 H 0.222687 0.645170 0.472348 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3367(2) 0.64139(11) 0.2764(2) 0.0410(5) Uani 1 1 d . . . . .
C14 C 0.3204(2) 0.71601(11) 0.2379(2) 0.0404(5) Uani 1 1 d . . . . .
C15 C 0.2256(3) 0.75784(14) 0.3060(3) 0.0569(6) Uani 1 1 d . . . . .
H15 H 0.169556 0.739455 0.380167 0.068 Uiso 1 1 calc R U . . .
C16 C 0.2141(3) 0.82688(15) 0.2641(4) 0.0687(8) Uani 1 1 d . . . . .
H16 H 0.149039 0.854584 0.308880 0.082 Uiso 1 1 calc R U . . .
C17 C 0.2975(3) 0.85481(14) 0.1573(4) 0.0654(8) Uani 1 1 d . . . . .
H17 H 0.289778 0.901478 0.130281 0.079 Uiso 1 1 calc R U . . .
C18 C 0.3927(3) 0.81386(14) 0.0901(3) 0.0619(7) Uani 1 1 d . . . . .
H18 H 0.450111 0.832929 0.018093 0.074 Uiso 1 1 calc R U . . .
C19 C 0.4036(3) 0.74452(13) 0.1290(3) 0.0502(5) Uani 1 1 d . . . . .
H19 H 0.467273 0.716789 0.081760 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1462(3) 0.56468(18) 0.3425(4) 0.0698(8) Uani 1 1 d . . . . .
H20A H 0.181800 0.530082 0.274686 0.105 Uiso 1 1 calc R U . . .
H20B H 0.085613 0.594081 0.287511 0.105 Uiso 1 1 calc R U . . .
H20C H 0.099983 0.542188 0.424705 0.105 Uiso 1 1 calc R U . . .
N1 N 0.4504(2) 0.67153(9) 0.5805(2) 0.0418(4) Uani 1 1 d . . . . .
N2 N 0.4485(2) 0.60029(9) 0.5816(2) 0.0451(4) Uani 1 1 d . . . . .
O1 O 0.6325(2) 0.97057(9) 0.8155(3) 0.0653(5) Uani 1 1 d . . . . .
O2 O 0.4103(2) 0.60442(9) 0.2024(2) 0.0620(5) Uani 1 1 d . . . . .
O3 O 0.3503(3) 0.50110(9) 0.5031(3) 0.0723(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.405(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.364(3) . ?
C2 C7 1.376(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C8 1.466(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.314(3) . ?
C8 C9 1.423(3) . ?
C9 C10 1.348(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.359(3) . ?
C10 H10 0.9300 . ?
C11 O3 1.202(3) . ?
C11 N2 1.403(3) . ?
C11 C12 1.503(4) . ?
C12 C13 1.519(3) . ?
C12 C20 1.521(3) . ?
C12 H12 0.9800 . ?
C13 O2 1.213(3) . ?
C13 C14 1.481(3) . ?
C14 C19 1.381(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.368(2) . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 116.1(2) . . ?
O1 C2 C3 124.5(2) . . ?
C7 C2 C3 119.4(2) . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 C8 121.50(19) . . ?
C6 C5 C8 120.9(2) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N1 C8 C9 111.1(2) . . ?
N1 C8 C5 120.46(19) . . ?
C9 C8 C5 128.4(2) . . ?
C10 C9 C8 105.7(2) . . ?
C10 C9 H9 127.2 . . ?
C8 C9 H9 127.2 . . ?
C9 C10 N2 106.6(2) . . ?
C9 C10 H10 126.7 . . ?
N2 C10 H10 126.7 . . ?
O3 C11 N2 119.4(3) . . ?
O3 C11 C12 125.7(3) . . ?
N2 C11 C12 114.87(18) . . ?
C11 C12 C13 108.22(19) . . ?
C11 C12 C20 110.2(2) . . ?
C13 C12 C20 109.6(2) . . ?
C11 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
C20 C12 H12 109.6 . . ?
O2 C13 C14 120.8(2) . . ?
O2 C13 C12 118.1(2) . . ?
C14 C13 C12 121.05(18) . . ?
C19 C14 C15 119.0(2) . . ?
C19 C14 C13 118.3(2) . . ?
C15 C14 C13 122.7(2) . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 N2 104.58(18) . . ?
C10 N2 N1 112.04(19) . . ?
C10 N2 C11 127.2(2) . . ?
N1 N2 C11 120.47(19) . . ?
C2 O1 C1 118.7(2) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_op_a
_database_code_depnum_ccdc_archive 'CCDC 1919855'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Br N2 O2'
_chemical_formula_weight         408.27

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic'
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.3784(10)
_cell_length_b                   8.5648(7)
_cell_length_c                   37.271(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3632.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6386
_cell_measurement_theta_min      2.8255
_cell_measurement_theta_max      25.0055

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6220
_exptl_absorpt_correction_T_max  0.6583
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34343
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3336
_reflns_number_gt                2131
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0453P)²+3.6831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3336
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.47388(5) 0.22845(6) 0.337172(12) 0.0879(2) Uani 1 1 d . . .
C1 C 0.2587(4) 0.5057(5) 0.53928(11) 0.0675(11) Uani 1 1 d . . .
H1 H 0.2096 0.5602 0.5548 0.081 Uiso 1 1 calc R . .
C2 C 0.2552(4) 0.5107(5) 0.50329(10) 0.0691(12) Uani 1 1 d . . .
H2 H 0.2037 0.5689 0.4892 0.083 Uiso 1 1 calc R . .
C3 C 0.3440(3) 0.4116(4) 0.49107(9) 0.0433(8) Uani 1 1 d . . .
C4 C 0.3772(3) 0.3706(4) 0.45429(9) 0.0445(8) Uani 1 1 d . . .
C5 C 0.3119(3) 0.4231(5) 0.42542(10) 0.0550(10) Uani 1 1 d . . .
H5 H 0.2475 0.4875 0.4295 0.066 Uiso 1 1 calc R . .
C6 C 0.3398(3) 0.3826(5) 0.39086(10) 0.0580(10) Uani 1 1 d . . .
H6 H 0.2952 0.4195 0.3717 0.070 Uiso 1 1 calc R . .
C7 C 0.4338(4) 0.2875(5) 0.38493(10) 0.0563(10) Uani 1 1 d . . .
C8 C 0.5019(4) 0.2324(5) 0.41277(10) 0.0597(10) Uani 1 1 d . . .
H8 H 0.5660 0.1679 0.4084 0.072 Uiso 1 1 calc R . .
C9 C 0.4727(3) 0.2755(4) 0.44734(10) 0.0525(9) Uani 1 1 d . . .
H9 H 0.5182 0.2397 0.4664 0.063 Uiso 1 1 calc R . .
C10 C 0.3858(3) 0.3585(4) 0.58348(8) 0.0407(8) Uani 1 1 d . . .
C11 C 0.4764(3) 0.2555(4) 0.58644(9) 0.0481(8) Uani 1 1 d . . .
C12 C 0.5215(4) 0.2014(5) 0.62156(9) 0.0599(10) Uani 1 1 d . . .
H12A H 0.6066 0.1993 0.6206 0.072 Uiso 1 1 calc R . .
H12B H 0.4946 0.0954 0.6256 0.072 Uiso 1 1 calc R . .
C13 C 0.4847(4) 0.2993(7) 0.65236(12) 0.0876(16) Uani 1 1 d . . .
H13 H 0.5308 0.3949 0.6491 0.105 Uiso 1 1 calc R . .
C14 C 0.3664(4) 0.3541(5) 0.65083(10) 0.0682(12) Uani 1 1 d . . .
H14A H 0.3573 0.4366 0.6684 0.082 Uiso 1 1 calc R . .
H14B H 0.3148 0.2692 0.6579 0.082 Uiso 1 1 calc R . .
C15 C 0.3260(3) 0.4147(4) 0.61529(10) 0.0517(9) Uani 1 1 d . . .
C16 C 0.5304(4) 0.2354(5) 0.68796(10) 0.0628(11) Uani 1 1 d . . .
C17 C 0.6404(4) 0.2785(6) 0.69861(12) 0.0801(13) Uani 1 1 d . . .
H17 H 0.6840 0.3447 0.6840 0.096 Uiso 1 1 calc R . .
C18 C 0.6888(5) 0.2278(7) 0.73011(13) 0.0992(17) Uani 1 1 d . . .
H18 H 0.7636 0.2605 0.7368 0.119 Uiso 1 1 calc R . .
C19 C 0.6272(6) 0.1299(8) 0.75150(13) 0.1009(18) Uani 1 1 d . . .
H19 H 0.6596 0.0951 0.7730 0.121 Uiso 1 1 calc R . .
C20 C 0.5188(6) 0.0829(7) 0.74167(14) 0.0987(17) Uani 1 1 d . . .
H20 H 0.4767 0.0149 0.7563 0.118 Uiso 1 1 calc R . .
C21 C 0.4703(4) 0.1357(6) 0.70990(12) 0.0824(13) Uani 1 1 d . . .
H21 H 0.3954 0.1028 0.7034 0.099 Uiso 1 1 calc R . .
N1 N 0.3458(2) 0.4079(3) 0.54897(7) 0.0433(7) Uani 1 1 d . . .
N2 N 0.3988(2) 0.3492(3) 0.51911(7) 0.0425(7) Uani 1 1 d . . .
O1 O 0.2428(3) 0.5046(4) 0.61409(7) 0.0768(9) Uani 1 1 d . . .
O4 O 0.5322(2) 0.1927(4) 0.55878(7) 0.0675(8) Uani 1 1 d . . .
H4 H 0.5063 0.2294 0.5401 0.101 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
Br1 C7 1.906(4) . ?
C1 C2 1.343(5) . ?
C1 N1 1.347(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(5) . ?
C2 H2 0.9300 . ?
C3 N2 1.329(4) . ?
C3 C4 1.465(5) . ?
C4 C5 1.383(5) . ?
C4 C9 1.383(5) . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.363(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(5) . ?
C8 C9 1.381(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.361(5) . ?
C10 N1 1.428(4) . ?
C10 C15 1.449(5) . ?
C11 O4 1.325(4) . ?
C11 C12 1.481(5) . ?
C12 C13 1.481(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.426(6) . ?
C13 C16 1.527(6) . ?
C13 H13 0.9800 . ?
C14 C15 1.495(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O1 1.221(4) . ?
C16 C17 1.364(6) . ?
C16 C21 1.366(6) . ?
C17 C18 1.368(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.353(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.348(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 N2 1.362(4) . ?
O4 H4 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 108.0(4) . . ?
C2 C1 H1 126.0 . . ?
N1 C1 H1 126.0 . . ?
C1 C2 C3 106.6(3) . . ?
C1 C2 H2 126.7 . . ?
C3 C2 H2 126.7 . . ?
N2 C3 C2 109.1(3) . . ?
N2 C3 C4 121.2(3) . . ?
C2 C3 C4 129.7(3) . . ?
C5 C4 C9 117.9(3) . . ?
C5 C4 C3 120.8(3) . . ?
C9 C4 C3 121.3(3) . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 Br1 119.9(3) . . ?
C8 C7 Br1 118.5(3) . . ?
C7 C8 C9 118.4(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C4 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C11 C10 N1 120.4(3) . . ?
C11 C10 C15 120.3(3) . . ?
N1 C10 C15 119.3(3) . . ?
O4 C11 C10 124.3(3) . . ?
O4 C11 C12 113.2(3) . . ?
C10 C11 C12 122.5(3) . . ?
C11 C12 C13 114.2(3) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 115.0(4) . . ?
C14 C13 C16 118.3(4) . . ?
C12 C13 C16 112.0(4) . . ?
C14 C13 H13 103.0 . . ?
C12 C13 H13 103.0 . . ?
C16 C13 H13 103.0 . . ?
C13 C14 C15 116.1(4) . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O1 C15 C10 122.9(3) . . ?
O1 C15 C14 119.3(3) . . ?
C10 C15 C14 117.7(3) . . ?
C17 C16 C21 117.0(4) . . ?
C17 C16 C13 117.9(4) . . ?
C21 C16 C13 125.0(5) . . ?
C16 C17 C18 122.2(5) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C19 C18 C17 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0(5) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 121.1(5) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C1 N1 N2 109.6(3) . . ?
C1 N1 C10 131.3(3) . . ?
N2 N1 C10 119.1(3) . . ?
C3 N2 N1 106.6(3) . . ?
C11 O4 H4 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_20170607a_0m
_database_code_depnum_ccdc_archive 'CCDC 1919916'
loop_
_audit_author_name
_audit_author_address
youpengzuo
;no
China
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36

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      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                   6.8253(4)
_cell_length_b                   7.8483(4)
_cell_length_c                   30.9897(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.986(2)
_cell_angle_gamma                90
_cell_volume                     1643.93(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_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            32327
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.964
_diffrn_reflns_theta_max         25.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2988
_reflns_number_gt                2762
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.3500P)²] 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         2988
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.3521
_refine_ls_wR_factor_gt          0.3322
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.005

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 0.9252(3) 0.3830(2) 0.11419(5) 0.0579(6) Uani 1 1 d . . . . .
O2 O 0.5804(3) 0.0169(3) 0.10504(7) 0.0678(7) Uani 1 1 d . . . . .
N1 N 0.8175(3) 0.28398(19) 0.04667(5) 0.0360(6) Uani 1 1 d . . . . .
N2 N 0.7731(3) 0.1455(2) 0.01941(5) 0.0425(6) Uani 1 1 d . . . . .
C1 C 0.5990(4) 0.4671(4) -0.09816(8) 0.0579(7) Uani 1 1 d . . . . .
H1A H 0.4970 0.5449 -0.1101 0.087 Uiso 1 1 calc R U . . .
H1B H 0.5472 0.3533 -0.0993 0.087 Uiso 1 1 calc R U . . .
H1C H 0.7073 0.4732 -0.1148 0.087 Uiso 1 1 calc R U . . .
C2 C 0.6699(3) 0.5140(3) -0.05182(7) 0.0402(6) Uani 1 1 d . . . . .
C3 C 0.6943(3) 0.6808(3) -0.03867(8) 0.0474(7) Uani 1 1 d . . . . .
H3 H 0.6633 0.7668 -0.0591 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7640(3) 0.7256(2) 0.00423(9) 0.0473(7) Uani 1 1 d . . . . .
H4 H 0.7792 0.8405 0.0113 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8113(3) 0.6061(2) 0.03665(7) 0.0410(6) Uani 1 1 d . . . . .
H5 H 0.8582 0.6365 0.0652 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7840(3) 0.4370(2) 0.02374(6) 0.0320(6) Uani 1 1 d . . . . .
C7 C 0.7153(3) 0.3909(2) -0.01916(6) 0.0337(6) Uani 1 1 d . . . . .
C8 C 0.7112(3) 0.2085(2) -0.01912(6) 0.0410(6) Uani 1 1 d . . . . .
H8 H 0.6693 0.1426 -0.0436 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8931(3) 0.2608(3) 0.09010(6) 0.0407(6) Uani 1 1 d . . . . .
C10 C 0.9308(3) 0.0789(3) 0.10478(7) 0.0458(7) Uani 1 1 d . . . . .
H10 H 0.9703 0.0128 0.0806 0.055 Uiso 1 1 calc R U . . .
C11 C 1.0903(3) 0.0597(3) 0.14462(7) 0.0492(7) Uani 1 1 d . . . . .
H11A H 1.0790 0.1488 0.1658 0.059 Uiso 1 1 calc R U . . .
H11B H 1.2219 0.0632 0.1362 0.059 Uiso 1 1 calc R U . . .
C12 C 1.0465(4) -0.1164(3) 0.16293(7) 0.0513(7) Uani 1 1 d . . . . .
H12 H 1.0901 -0.2032 0.1436 0.062 Uiso 1 1 calc R U . . .
C13 C 0.8229(4) -0.1209(3) 0.15787(9) 0.0620(8) Uani 1 1 d . . . . .
H13A H 0.7753 -0.2363 0.1522 0.074 Uiso 1 1 calc R U . . .
H13B H 0.7765 -0.0802 0.1842 0.074 Uiso 1 1 calc R U . . .
C14 C 0.7499(3) -0.0071(3) 0.12015(7) 0.0477(7) Uani 1 1 d . . . . .
C15 C 1.1534(3) -0.1475(3) 0.20836(7) 0.0464(7) Uani 1 1 d . . . . .
C16 C 1.1002(4) -0.0667(3) 0.24460(8) 0.0620(8) Uani 1 1 d . . . . .
H16 H 0.9936 0.0082 0.2414 0.074 Uiso 1 1 calc R U . . .
C17 C 1.2029(6) -0.0954(4) 0.28550(9) 0.0718(9) Uani 1 1 d . . . . .
H17 H 1.1636 -0.0410 0.3095 0.086 Uiso 1 1 calc R U . . .
C18 C 1.3621(7) -0.2033(4) 0.29101(9) 0.0820(11) Uani 1 1 d . . . . .
H18 H 1.4319 -0.2211 0.3186 0.098 Uiso 1 1 calc R U . . .
C19 C 1.4174(6) -0.2846(5) 0.25578(10) 0.0829(11) Uani 1 1 d . . . . .
H19 H 1.5247 -0.3587 0.2593 0.100 Uiso 1 1 calc R U . . .
C20 C 1.3133(4) -0.2567(4) 0.21435(9) 0.0659(8) Uani 1 1 d . . . . .
H20 H 1.3522 -0.3125 0.1905 0.079 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
O1 C9 1.216(3) . ?
O2 C14 1.201(3) . ?
N1 N2 1.384(2) . ?
N1 C9 1.385(2) . ?
N1 C6 1.398(2) . ?
N2 C8 1.307(3) . ?
C1 C2 1.496(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.374(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(2) . ?
C7 C8 1.432(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.510(3) . ?
C10 C11 1.536(3) . ?
C10 C14 1.539(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.539(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(4) . ?
C12 C15 1.513(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.500(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C20 1.380(4) . ?
C15 C16 1.381(3) . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(4) . ?
C19 H19 0.9300 . ?
C20 H20 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
N2 N1 C9 120.70(15) . . ?
N2 N1 C6 110.97(15) . . ?
C9 N1 C6 128.26(16) . . ?
C8 N2 N1 106.02(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 115.9(2) . . ?
C3 C2 C1 121.9(2) . . ?
C7 C2 C1 122.2(2) . . ?
C2 C3 C4 122.32(19) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 122.49(18) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 115.5(2) . . ?
C4 C5 H5 122.2 . . ?
C6 C5 H5 122.2 . . ?
C5 C6 C7 122.38(18) . . ?
C5 C6 N1 131.87(19) . . ?
C7 C6 N1 105.73(15) . . ?
C6 C7 C2 121.36(18) . . ?
C6 C7 C8 105.23(16) . . ?
C2 C7 C8 133.40(18) . . ?
N2 C8 C7 112.04(16) . . ?
N2 C8 H8 124.0 . . ?
C7 C8 H8 124.0 . . ?
O1 C9 N1 120.27(19) . . ?
O1 C9 C10 123.51(19) . . ?
N1 C9 C10 116.22(18) . . ?
C9 C10 C11 114.01(19) . . ?
C9 C10 C14 113.43(17) . . ?
C11 C10 C14 102.58(16) . . ?
C9 C10 H10 108.9 . . ?
C11 C10 H10 108.9 . . ?
C14 C10 H10 108.9 . . ?
C10 C11 C12 103.41(18) . . ?
C10 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C15 116.2(2) . . ?
C13 C12 C11 103.16(18) . . ?
C15 C12 C11 113.3(2) . . ?
C13 C12 H12 107.9 . . ?
C15 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
C14 C13 C12 106.7(2) . . ?
C14 C13 H13A 110.4 . . ?
C12 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
O2 C14 C13 126.5(2) . . ?
O2 C14 C10 125.5(2) . . ?
C13 C14 C10 107.94(17) . . ?
C20 C15 C16 117.9(2) . . ?
C20 C15 C12 119.7(2) . . ?
C16 C15 C12 122.4(2) . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.9(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?

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
C9 N1 N2 C8 -178.19(18) . . . . ?
C6 N1 N2 C8 -0.9(2) . . . . ?
C7 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C4 -178.7(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C4 C5 C6 N1 179.00(19) . . . . ?
N2 N1 C6 C5 -178.25(19) . . . . ?
C9 N1 C6 C5 -1.2(4) . . . . ?
N2 N1 C6 C7 0.4(2) . . . . ?
C9 N1 C6 C7 177.43(18) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
N1 C6 C7 C2 -178.70(15) . . . . ?
C5 C6 C7 C8 179.02(18) . . . . ?
N1 C6 C7 C8 0.2(2) . . . . ?
C3 C2 C7 C6 -1.0(3) . . . . ?
C1 C2 C7 C6 179.03(18) . . . . ?
C3 C2 C7 C8 -179.6(2) . . . . ?
C1 C2 C7 C8 0.4(3) . . . . ?
N1 N2 C8 C7 1.0(2) . . . . ?
C6 C7 C8 N2 -0.8(2) . . . . ?
C2 C7 C8 N2 177.9(2) . . . . ?
N2 N1 C9 O1 -177.42(18) . . . . ?
C6 N1 C9 O1 5.8(3) . . . . ?
N2 N1 C9 C10 2.4(3) . . . . ?
C6 N1 C9 C10 -174.39(17) . . . . ?
O1 C9 C10 C11 -25.4(3) . . . . ?
N1 C9 C10 C11 154.75(19) . . . . ?
O1 C9 C10 C14 91.5(3) . . . . ?
N1 C9 C10 C14 -88.3(2) . . . . ?
C9 C10 C11 C12 159.52(18) . . . . ?
C14 C10 C11 C12 36.5(2) . . . . ?
C10 C11 C12 C13 -40.0(3) . . . . ?
C10 C11 C12 C15 -166.4(2) . . . . ?
C15 C12 C13 C14 152.1(2) . . . . ?
C11 C12 C13 C14 27.5(3) . . . . ?
C12 C13 C14 O2 176.9(3) . . . . ?
C12 C13 C14 C10 -4.8(3) . . . . ?
C9 C10 C14 O2 35.1(4) . . . . ?
C11 C10 C14 O2 158.5(3) . . . . ?
C9 C10 C14 C13 -143.3(2) . . . . ?
C11 C10 C14 C13 -19.8(3) . . . . ?
C13 C12 C15 C20 134.7(3) . . . . ?
C11 C12 C15 C20 -106.1(3) . . . . ?
C13 C12 C15 C16 -47.0(3) . . . . ?
C11 C12 C15 C16 72.2(3) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?
C12 C15 C16 C17 -178.8(3) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C12 C15 C20 C19 178.5(3) . . . . ?
C18 C19 C20 C15 -0.1(6) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045

