# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_d8v22521
_database_code_depnum_ccdc_archive 'CCDC 2428416'
loop_
_audit_author_name
_audit_author_address
'Lingling Li'
;Shanghai Jiaotong University
China
;
_audit_update_record             
;
2025-03-03 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32

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                   9.6531(5)
_cell_length_b                   14.4417(6)
_cell_length_c                   9.9636(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1389.00(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4652
_cell_measurement_theta_min      5.076
_cell_measurement_theta_max      49.300

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4754
_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            11528
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         25.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2650
_reflns_number_gt                2172
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.948

_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)+(0.0822P)²+0.2634P] 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 852 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.9(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2650
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4085(4) 0.0752(3) 0.8143(4) 0.0938(11) Uani 1 1 d . . . . .
N1 N 0.5488(4) 0.1923(2) 0.7363(4) 0.0675(10) Uani 1 1 d . . . . .
N2 N 0.3955(3) 0.13268(19) 0.5968(4) 0.0562(8) Uani 1 1 d . . . . .
C1 C 0.4477(4) 0.1284(3) 0.7245(4) 0.0642(10) Uani 1 1 d . . . . .
C2 C 0.5009(4) 0.1795(2) 0.5121(4) 0.0537(9) Uani 1 1 d . . . . .
H2 H 0.5720 0.1343 0.4871 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5619(3) 0.2462(2) 0.6137(4) 0.0538(8) Uani 1 1 d . . . . .
H3 H 0.6598 0.2578 0.5936 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4827(4) 0.3373(2) 0.6220(5) 0.0580(10) Uani 1 1 d . . . . .
C5 C 0.4952(5) 0.3903(3) 0.7375(6) 0.0805(14) Uani 1 1 d . . . . .
H5 H 0.5516 0.3688 0.8064 0.097 Uiso 1 1 calc R U . . .
C6 C 0.4281(6) 0.4730(4) 0.7544(9) 0.1038(19) Uani 1 1 d . . . . .
H6 H 0.4380 0.5071 0.8331 0.125 Uiso 1 1 calc R U . . .
C7 C 0.3472(6) 0.5035(3) 0.6535(9) 0.106(2) Uani 1 1 d . . . . .
H7 H 0.3009 0.5596 0.6631 0.127 Uiso 1 1 calc R U . . .
C8 C 0.3310(5) 0.4531(3) 0.5350(8) 0.098(2) Uani 1 1 d . . . . .
H8 H 0.2733 0.4757 0.4678 0.117 Uiso 1 1 calc R U . . .
C9 C 0.4011(4) 0.3680(3) 0.5158(5) 0.0655(11) Uani 1 1 d . . . . .
C10 C 0.3922(4) 0.3141(3) 0.3918(5) 0.0709(13) Uani 1 1 d . . . . .
C11 C 0.3386(7) 0.3514(5) 0.2746(7) 0.114(2) Uani 1 1 d . . . . .
H11 H 0.3027 0.4111 0.2762 0.137 Uiso 1 1 calc R U . . .
C12 C 0.3371(10) 0.3044(7) 0.1599(8) 0.142(4) Uani 1 1 d . . . . .
H12 H 0.3012 0.3325 0.0835 0.170 Uiso 1 1 calc R U . . .
C13 C 0.3866(7) 0.2159(6) 0.1512(6) 0.116(2) Uani 1 1 d . . . . .
H13 H 0.3843 0.1841 0.0701 0.139 Uiso 1 1 calc R U . . .
C14 C 0.4423(6) 0.1727(4) 0.2698(5) 0.0914(16) Uani 1 1 d . . . . .
H14 H 0.4761 0.1125 0.2670 0.110 Uiso 1 1 calc R U . . .
C15 C 0.4444(4) 0.2226(3) 0.3869(4) 0.0621(10) Uani 1 1 d . . . . .
C16 C 0.6411(6) 0.1970(4) 0.8512(6) 0.0952(17) Uani 1 1 d . . . . .
H16A H 0.5993 0.2339 0.9204 0.143 Uiso 1 1 calc R U . . .
H16B H 0.7274 0.2245 0.8246 0.143 Uiso 1 1 calc R U . . .
H16C H 0.6577 0.1356 0.8847 0.143 Uiso 1 1 calc R U . . .
C17 C 0.3242(5) 0.0526(3) 0.5436(5) 0.0805(14) Uani 1 1 d . . . . .
H17A H 0.3909 0.0072 0.5156 0.121 Uiso 1 1 calc R U . . .
H17B H 0.2687 0.0708 0.4681 0.121 Uiso 1 1 calc R U . . .
H17C H 0.2657 0.0266 0.6118 0.121 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 C1 1.239(5) . ?
N1 C1 1.348(5) . ?
N1 C16 1.453(6) . ?
N1 C3 1.454(5) . ?
N2 C1 1.370(6) . ?
N2 C17 1.447(5) . ?
N2 C2 1.485(5) . ?
C2 C15 1.497(6) . ?
C2 C3 1.516(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.524(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.387(6) . ?
C4 C9 1.393(6) . ?
C5 C6 1.369(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.463(7) . ?
C10 C11 1.386(7) . ?
C10 C15 1.415(6) . ?
C11 C12 1.329(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.440(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(7) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 N1 C16 123.0(4) . . ?
C1 N1 C3 110.9(3) . . ?
C16 N1 C3 125.7(4) . . ?
C1 N2 C17 118.6(3) . . ?
C1 N2 C2 107.2(3) . . ?
C17 N2 C2 118.8(4) . . ?
O1 C1 N1 125.7(4) . . ?
O1 C1 N2 125.9(4) . . ?
N1 C1 N2 108.4(3) . . ?
N2 C2 C15 114.4(3) . . ?
N2 C2 C3 100.1(3) . . ?
C15 C2 C3 115.7(3) . . ?
N2 C2 H2 108.7 . . ?
C15 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
N1 C3 C2 100.8(3) . . ?
N1 C3 C4 111.9(3) . . ?
C2 C3 C4 112.9(3) . . ?
N1 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
C4 C3 H3 110.3 . . ?
C5 C4 C9 120.2(4) . . ?
C5 C4 C3 118.6(4) . . ?
C9 C4 C3 121.2(4) . . ?
C6 C5 C4 122.9(6) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C7 C6 C5 117.9(6) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 121.7(5) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 120.9(6) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C8 116.4(5) . . ?
C4 C9 C10 120.4(3) . . ?
C8 C9 C10 123.3(5) . . ?
C11 C10 C15 117.8(5) . . ?
C11 C10 C9 121.8(5) . . ?
C15 C10 C9 120.4(3) . . ?
C12 C11 C10 122.0(7) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 121.9(7) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 118.9(6) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 118.4(6) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 121.0(5) . . ?
C14 C15 C2 119.7(4) . . ?
C10 C15 C2 119.3(4) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C16 N1 C1 O1 10.3(7) . . . . ?
C3 N1 C1 O1 -176.7(4) . . . . ?
C16 N1 C1 N2 -169.9(4) . . . . ?
C3 N1 C1 N2 3.1(5) . . . . ?
C17 N2 C1 O1 -22.2(6) . . . . ?
C2 N2 C1 O1 -160.4(4) . . . . ?
C17 N2 C1 N1 158.0(4) . . . . ?
C2 N2 C1 N1 19.9(4) . . . . ?
C1 N2 C2 C15 -157.6(3) . . . . ?
C17 N2 C2 C15 64.4(5) . . . . ?
C1 N2 C2 C3 -33.2(3) . . . . ?
C17 N2 C2 C3 -171.2(3) . . . . ?
C1 N1 C3 C2 -23.7(4) . . . . ?
C16 N1 C3 C2 149.2(5) . . . . ?
C1 N1 C3 C4 96.6(4) . . . . ?
C16 N1 C3 C4 -90.6(5) . . . . ?
N2 C2 C3 N1 32.7(3) . . . . ?
C15 C2 C3 N1 156.2(3) . . . . ?
N2 C2 C3 C4 -86.8(4) . . . . ?
C15 C2 C3 C4 36.7(5) . . . . ?
N1 C3 C4 C5 45.4(4) . . . . ?
C2 C3 C4 C5 158.3(4) . . . . ?
N1 C3 C4 C9 -135.6(4) . . . . ?
C2 C3 C4 C9 -22.7(5) . . . . ?
C9 C4 C5 C6 1.1(7) . . . . ?
C3 C4 C5 C6 -179.9(4) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C5 C6 C7 C8 0.1(9) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
C5 C4 C9 C8 -1.7(5) . . . . ?
C3 C4 C9 C8 179.3(4) . . . . ?
C5 C4 C9 C10 177.5(4) . . . . ?
C3 C4 C9 C10 -1.4(5) . . . . ?
C7 C8 C9 C4 1.6(6) . . . . ?
C7 C8 C9 C10 -177.6(4) . . . . ?
C4 C9 C10 C11 -165.3(4) . . . . ?
C8 C9 C10 C11 13.9(7) . . . . ?
C4 C9 C10 C15 11.9(5) . . . . ?
C8 C9 C10 C15 -168.9(4) . . . . ?
C15 C10 C11 C12 -0.9(9) . . . . ?
C9 C10 C11 C12 176.4(6) . . . . ?
C10 C11 C12 C13 0.9(11) . . . . ?
C11 C12 C13 C14 -0.2(11) . . . . ?
C12 C13 C14 C15 -0.5(9) . . . . ?
C13 C14 C15 C10 0.4(7) . . . . ?
C13 C14 C15 C2 179.6(4) . . . . ?
C11 C10 C15 C14 0.2(6) . . . . ?
C9 C10 C15 C14 -177.1(4) . . . . ?
C11 C10 C15 C2 -179.0(4) . . . . ?
C9 C10 C15 C2 3.7(5) . . . . ?
N2 C2 C15 C14 -92.1(5) . . . . ?
C3 C2 C15 C14 152.2(4) . . . . ?
N2 C2 C15 C10 87.1(4) . . . . ?
C3 C2 C15 C10 -28.6(5) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.032

_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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2428418'
loop_
_audit_author_name
_audit_author_address
'Lingling Li'
;Shanghai Jiaotong University
China
;
_audit_update_record             
;
2025-03-03 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O2'
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.95460(10)
_cell_length_b                   15.5470(4)
_cell_length_c                   19.2131(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1479.97(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      68.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.698
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30609
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.657
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2694
_reflns_number_gt                2578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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-2019/1 (Sheldrick, 2019)'
_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)+(0.0578P)²+0.1415P] 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 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2694
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
N1 N 0.6183(3) 0.39806(8) 0.57162(7) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.2983(3) 0.44940(10) 0.64031(8) 0.0336(3) Uani 1 1 d . . . . .
C1 C 0.5936(3) 0.49764(10) 0.47003(9) 0.0275(4) Uani 1 1 d . . . . .
O1 O 0.4898(3) 0.38113(8) 0.39732(6) 0.0417(3) Uani 1 1 d . . . . .
O2 O 0.5328(3) 0.32973(8) 0.67714(6) 0.0394(3) Uani 1 1 d . . . . .
C6 C 0.7104(3) 0.57803(11) 0.48212(9) 0.0291(4) Uani 1 1 d . . . . .
C7 C 0.6799(3) 0.61935(11) 0.55144(9) 0.0285(4) Uani 1 1 d . . . . .
C8 C 0.8419(4) 0.68961(11) 0.57072(10) 0.0362(4) Uani 1 1 d . . . . .
H8 H 0.976911 0.709702 0.539588 0.043 Uiso 1 1 calc R U . . .
C9 C 0.8081(4) 0.73006(12) 0.63434(10) 0.0393(4) Uani 1 1 d . . . . .
H9 H 0.921646 0.776809 0.646854 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6102(4) 0.70262(12) 0.67952(10) 0.0404(5) Uani 1 1 d . . . . .
H10 H 0.580702 0.731906 0.722242 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4544(4) 0.63181(11) 0.66196(9) 0.0370(4) Uani 1 1 d . . . . .
H11 H 0.320679 0.612208 0.693645 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4888(3) 0.58869(10) 0.59911(9) 0.0293(4) Uani 1 1 d . . . . .
C13 C 0.3166(3) 0.51016(11) 0.58212(9) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.131974 0.528488 0.567233 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4426(3) 0.45190(11) 0.52706(8) 0.0279(4) Uani 1 1 d . . . . .
H14 H 0.298785 0.415055 0.505959 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7691(4) 0.32667(11) 0.54224(10) 0.0352(4) Uani 1 1 d . . . . .
H15A H 0.857543 0.345231 0.499150 0.053 Uiso 1 1 calc R U . . .
H15B H 0.645606 0.279066 0.532079 0.053 Uiso 1 1 calc R U . . .
H15C H 0.905995 0.307541 0.575646 0.053 Uiso 1 1 calc R U . . .
C16 C 0.4863(3) 0.38652(11) 0.63432(8) 0.0295(3) Uani 1 1 d . . . . .
C17 C 0.1154(4) 0.45490(13) 0.69923(10) 0.0399(4) Uani 1 1 d . . . . .
H17A H -0.036187 0.492660 0.687445 0.060 Uiso 1 1 calc R U . . .
H17B H 0.211895 0.478357 0.739514 0.060 Uiso 1 1 calc R U . . .
H17C H 0.047262 0.397385 0.710490 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5150(7) 0.33809(14) 0.33238(10) 0.0582(7) Uani 1 1 d . . . . .
H18A H 0.393925 0.288258 0.331502 0.087 Uiso 1 1 calc R U . . .
H18B H 0.701760 0.318740 0.326236 0.087 Uiso 1 1 calc R U . . .
H18C H 0.466801 0.377582 0.294620 0.087 Uiso 1 1 calc R U . . .
C2 C 0.6171(4) 0.45866(11) 0.40466(9) 0.0321(4) Uani 1 1 d . . . . .
C3 C 0.7641(4) 0.49841(13) 0.35171(10) 0.0384(4) Uani 1 1 d . . . . .
H3 H 0.786355 0.470971 0.307906 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8771(5) 0.57846(12) 0.36398(10) 0.0431(5) Uani 1 1 d . . . . .
H4 H 0.974429 0.606381 0.327868 0.052 Uiso 1 1 calc R U . . .
C5 C 0.8506(4) 0.61842(12) 0.42785(10) 0.0387(4) Uani 1 1 d . . . . .
H5 H 0.927935 0.673624 0.435025 0.046 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 C16 1.382(2) . ?
N1 C15 1.452(2) . ?
N1 C14 1.480(2) . ?
N2 C16 1.355(2) . ?
N2 C17 1.452(2) . ?
N2 C13 1.466(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.399(2) . ?
C1 C14 1.506(2) . ?
O1 C2 1.368(2) . ?
O1 C18 1.421(2) . ?
O2 C16 1.229(2) . ?
C6 C5 1.401(3) . ?
C6 C7 1.486(2) . ?
C7 C12 1.401(2) . ?
C7 C8 1.405(2) . ?
C8 C9 1.385(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.392(2) . ?
C12 C13 1.525(2) . ?
C13 C14 1.526(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.382(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C15 118.88(14) . . ?
C16 N1 C14 107.40(13) . . ?
C15 N1 C14 120.66(14) . . ?
C16 N2 C17 122.51(15) . . ?
C16 N2 C13 110.93(13) . . ?
C17 N2 C13 126.51(14) . . ?
C6 C1 C2 120.16(15) . . ?
C6 C1 C14 120.50(15) . . ?
C2 C1 C14 119.34(15) . . ?
C2 O1 C18 117.70(15) . . ?
C1 C6 C5 118.85(16) . . ?
C1 C6 C7 119.58(15) . . ?
C5 C6 C7 121.57(16) . . ?
C12 C7 C8 118.56(16) . . ?
C12 C7 C6 120.51(16) . . ?
C8 C7 C6 120.93(16) . . ?
C9 C8 C7 121.10(18) . . ?
C10 C9 C8 120.12(18) . . ?
C9 C10 C11 119.28(17) . . ?
C10 C11 C12 121.70(18) . . ?
C11 C12 C7 119.10(17) . . ?
C11 C12 C13 120.19(16) . . ?
C7 C12 C13 120.70(15) . . ?
N2 C13 C12 112.78(13) . . ?
N2 C13 C14 99.87(13) . . ?
C12 C13 C14 113.25(14) . . ?
N1 C14 C1 113.30(13) . . ?
N1 C14 C13 100.09(12) . . ?
C1 C14 C13 115.31(14) . . ?
O2 C16 N2 126.17(16) . . ?
O2 C16 N1 126.03(16) . . ?
N2 C16 N1 107.80(14) . . ?
O1 C2 C3 123.77(16) . . ?
O1 C2 C1 115.84(15) . . ?
C3 C2 C1 120.39(16) . . ?
C4 C3 C2 119.00(18) . . ?
C5 C4 C3 121.12(18) . . ?
C4 C5 C6 120.43(17) . . ?

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
C2 C1 C6 C5 0.0(2) . . . . ?
C14 C1 C6 C5 179.68(16) . . . . ?
C2 C1 C6 C7 178.96(15) . . . . ?
C14 C1 C6 C7 -1.3(2) . . . . ?
C1 C6 C7 C12 -14.3(2) . . . . ?
C5 C6 C7 C12 164.73(16) . . . . ?
C1 C6 C7 C8 165.53(15) . . . . ?
C5 C6 C7 C8 -15.5(3) . . . . ?
C12 C7 C8 C9 -2.3(2) . . . . ?
C6 C7 C8 C9 177.87(15) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 3.0(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C7 -2.1(2) . . . . ?
C10 C11 C12 C13 179.04(15) . . . . ?
C8 C7 C12 C11 3.9(2) . . . . ?
C6 C7 C12 C11 -176.32(14) . . . . ?
C8 C7 C12 C13 -177.25(14) . . . . ?
C6 C7 C12 C13 2.5(2) . . . . ?
C16 N2 C13 C12 -94.84(16) . . . . ?
C17 N2 C13 C12 82.6(2) . . . . ?
C16 N2 C13 C14 25.67(17) . . . . ?
C17 N2 C13 C14 -156.88(17) . . . . ?
C11 C12 C13 N2 -46.0(2) . . . . ?
C7 C12 C13 N2 135.13(15) . . . . ?
C11 C12 C13 C14 -158.53(14) . . . . ?
C7 C12 C13 C14 22.6(2) . . . . ?
C16 N1 C14 C1 157.97(14) . . . . ?
C15 N1 C14 C1 -61.3(2) . . . . ?
C16 N1 C14 C13 34.65(16) . . . . ?
C15 N1 C14 C13 175.37(14) . . . . ?
C6 C1 C14 N1 -87.49(18) . . . . ?
C2 C1 C14 N1 92.25(18) . . . . ?
C6 C1 C14 C13 27.0(2) . . . . ?
C2 C1 C14 C13 -153.25(15) . . . . ?
N2 C13 C14 N1 -34.57(14) . . . . ?
C12 C13 C14 N1 85.60(15) . . . . ?
N2 C13 C14 C1 -156.48(13) . . . . ?
C12 C13 C14 C1 -36.31(19) . . . . ?
C17 N2 C16 O2 -2.6(3) . . . . ?
C13 N2 C16 O2 174.92(17) . . . . ?
C17 N2 C16 N1 177.82(16) . . . . ?
C13 N2 C16 N1 -4.61(18) . . . . ?
C15 N1 C16 O2 19.0(3) . . . . ?
C14 N1 C16 O2 160.58(17) . . . . ?
C15 N1 C16 N2 -161.44(15) . . . . ?
C14 N1 C16 N2 -19.89(17) . . . . ?
C18 O1 C2 C3 1.6(3) . . . . ?
C18 O1 C2 C1 -178.20(19) . . . . ?
C6 C1 C2 O1 -178.26(15) . . . . ?
C14 C1 C2 O1 2.0(2) . . . . ?
C6 C1 C2 C3 2.0(3) . . . . ?
C14 C1 C2 C3 -177.76(16) . . . . ?
O1 C2 C3 C4 177.71(18) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C1 C6 C5 C4 -1.3(3) . . . . ?
C7 C6 C5 C4 179.72(17) . . . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2428420'
loop_
_audit_author_name
_audit_author_address
'Lingling Li'
;Shanghai Jiaotong University
China
;
_audit_update_record             
;
2025-03-03 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Br N2 O'
_chemical_formula_sum            'C17 H15 Br N2 O'
_chemical_formula_weight         343.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.1594(4)
_cell_length_b                   15.0950(11)
_cell_length_c                   18.2386(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1420.44(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5603
_cell_measurement_theta_min      3.7710
_cell_measurement_theta_max      75.4490

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.939
_shelx_estimated_absorpt_T_min   0.478
_shelx_estimated_absorpt_T_max   0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8693
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.801
_diffrn_reflns_theta_max         80.125
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2750
_reflns_number_gt                2384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.589
_reflns_Friedel_fraction_max     0.799
_reflns_Friedel_fraction_full    0.910

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0523P)²+3.8115P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.035(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
C7 C 0.3378(15) 0.5096(5) 0.5745(3) 0.0235(14) Uani 1 1 d . . . . .
H7 H 0.162696 0.530455 0.558572 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8005(16) 0.3307(5) 0.5284(4) 0.0286(17) Uani 1 1 d . . . . .
H6A H 0.928192 0.311252 0.564781 0.043 Uiso 1 1 calc R U . . .
H6B H 0.890409 0.354906 0.485538 0.043 Uiso 1 1 calc R U . . .
H6C H 0.693871 0.280109 0.513391 0.043 Uiso 1 1 calc R U . . .
C8 C 0.5073(14) 0.5875(4) 0.5970(3) 0.0239(16) Uani 1 1 d . . . . .
C5 C 0.5062(14) 0.3817(4) 0.6253(3) 0.0255(16) Uani 1 1 d . . . . .
C4 C 0.1305(16) 0.4433(6) 0.6924(4) 0.0351(19) Uani 1 1 d . . . . .
H4A H 0.210850 0.470437 0.735630 0.053 Uiso 1 1 calc R U . . .
H4B H 0.078505 0.382495 0.704009 0.053 Uiso 1 1 calc R U . . .
H4C H -0.022443 0.477735 0.678121 0.053 Uiso 1 1 calc R U . . .
C10 C 0.6415(16) 0.6917(5) 0.6908(4) 0.0297(18) Uani 1 1 d . . . . .
H10 H 0.617266 0.717206 0.737950 0.036 Uiso 1 1 calc R U . . .
C16 C 0.8884(14) 0.5963(5) 0.3500(4) 0.0293(16) Uani 1 1 d . . . . .
H16 H 0.985950 0.627706 0.314239 0.035 Uiso 1 1 calc R U . . .
C2 C 0.6041(15) 0.5038(4) 0.4565(3) 0.0222(16) Uani 1 1 d . . . . .
N2 N 0.3148(13) 0.4424(4) 0.6325(3) 0.0277(14) Uani 1 1 d . . . . .
C17 C 0.7700(17) 0.5170(5) 0.3320(4) 0.0285(17) Uani 1 1 d . . . . .
H17 H 0.787251 0.493233 0.284053 0.034 Uiso 1 1 calc R U . . .
C1 C 0.6267(15) 0.4729(4) 0.3843(4) 0.0239(16) Uani 1 1 d . . . . .
Br1 Br 0.44718(17) 0.36770(5) 0.35474(4) 0.0302(3) Uani 1 1 d . . . . .
O1 O 0.5558(12) 0.3216(3) 0.6688(2) 0.0320(12) Uani 1 1 d . . . . .
N1 N 0.6354(12) 0.3987(3) 0.5604(3) 0.0227(13) Uani 1 1 d . . . . .
C13 C 0.7004(14) 0.6206(4) 0.5500(3) 0.0240(15) Uani 1 1 d . . . . .
C3 C 0.4645(15) 0.4533(4) 0.5148(3) 0.0221(14) Uani 1 1 d . . . . .
H3 H 0.330159 0.414656 0.491561 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4784(15) 0.6248(4) 0.6668(3) 0.0264(15) Uani 1 1 d . . . . .
H9 H 0.344718 0.603911 0.698165 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8394(16) 0.7211(5) 0.6460(4) 0.0318(16) Uani 1 1 d . . . . .
H11 H 0.957244 0.764783 0.663123 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8657(16) 0.6865(5) 0.5760(4) 0.0309(17) Uani 1 1 d . . . . .
H12 H 0.999278 0.708291 0.544973 0.037 Uiso 1 1 calc R U . . .
C15 C 0.8640(14) 0.6297(5) 0.4205(3) 0.0269(15) Uani 1 1 d . . . . .
H15 H 0.943239 0.684787 0.432072 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7267(15) 0.5849(4) 0.4747(4) 0.0232(15) 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
C7 N2 1.470(8) . ?
C7 C8 1.522(9) . ?
C7 C3 1.528(9) . ?
C6 N1 1.456(9) . ?
C8 C9 1.400(8) . ?
C8 C13 1.406(10) . ?
C5 O1 1.232(8) . ?
C5 N2 1.353(9) . ?
C5 N1 1.383(8) . ?
C4 N2 1.448(9) . ?
C10 C11 1.382(12) . ?
C10 C9 1.385(10) . ?
C16 C17 1.383(10) . ?
C16 C15 1.386(9) . ?
C2 C1 1.403(8) . ?
C2 C14 1.417(9) . ?
C2 C3 1.494(9) . ?
C17 C1 1.378(10) . ?
C1 Br1 1.915(7) . ?
N1 C3 1.465(8) . ?
C13 C12 1.393(10) . ?
C13 C14 1.482(9) . ?
C11 C12 1.386(10) . ?
C15 C14 1.392(9) . ?

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 C7 C8 112.7(5) . . ?
N2 C7 C3 99.4(5) . . ?
C8 C7 C3 112.1(6) . . ?
C9 C8 C13 119.1(6) . . ?
C9 C8 C7 119.6(6) . . ?
C13 C8 C7 121.2(6) . . ?
O1 C5 N2 126.0(6) . . ?
O1 C5 N1 126.0(6) . . ?
N2 C5 N1 108.0(5) . . ?
C11 C10 C9 119.7(7) . . ?
C17 C16 C15 119.6(7) . . ?
C1 C2 C14 118.0(6) . . ?
C1 C2 C3 122.6(6) . . ?
C14 C2 C3 119.4(6) . . ?
C5 N2 C4 124.0(6) . . ?
C5 N2 C7 109.8(6) . . ?
C4 N2 C7 126.1(6) . . ?
C1 C17 C16 119.5(6) . . ?
C17 C1 C2 122.2(7) . . ?
C17 C1 Br1 117.8(5) . . ?
C2 C1 Br1 120.0(5) . . ?
C5 N1 C6 119.6(5) . . ?
C5 N1 C3 107.5(6) . . ?
C6 N1 C3 121.4(5) . . ?
C12 C13 C8 118.7(6) . . ?
C12 C13 C14 121.3(7) . . ?
C8 C13 C14 120.0(6) . . ?
N1 C3 C2 113.6(6) . . ?
N1 C3 C7 99.5(5) . . ?
C2 C3 C7 115.4(5) . . ?
C10 C9 C8 121.1(7) . . ?
C10 C11 C12 119.8(7) . . ?
C11 C12 C13 121.5(7) . . ?
C16 C15 C14 121.9(7) . . ?
C15 C14 C2 118.8(6) . . ?
C15 C14 C13 121.9(6) . . ?
C2 C14 C13 119.3(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
N2 C7 C8 C9 -44.1(9) . . . . ?
C3 C7 C8 C9 -155.2(6) . . . . ?
N2 C7 C8 C13 133.3(7) . . . . ?
C3 C7 C8 C13 22.1(9) . . . . ?
O1 C5 N2 C4 -2.5(11) . . . . ?
N1 C5 N2 C4 177.2(6) . . . . ?
O1 C5 N2 C7 172.9(7) . . . . ?
N1 C5 N2 C7 -7.4(7) . . . . ?
C8 C7 N2 C5 -90.0(7) . . . . ?
C3 C7 N2 C5 28.9(7) . . . . ?
C8 C7 N2 C4 85.3(9) . . . . ?
C3 C7 N2 C4 -155.8(7) . . . . ?
C15 C16 C17 C1 0.8(12) . . . . ?
C16 C17 C1 C2 -2.5(11) . . . . ?
C16 C17 C1 Br1 175.8(6) . . . . ?
C14 C2 C1 C17 2.2(11) . . . . ?
C3 C2 C1 C17 -175.7(7) . . . . ?
C14 C2 C1 Br1 -176.0(5) . . . . ?
C3 C2 C1 Br1 6.1(10) . . . . ?
O1 C5 N1 C6 16.8(10) . . . . ?
N2 C5 N1 C6 -162.9(6) . . . . ?
O1 C5 N1 C3 160.6(7) . . . . ?
N2 C5 N1 C3 -19.1(7) . . . . ?
C9 C8 C13 C12 3.3(10) . . . . ?
C7 C8 C13 C12 -174.1(6) . . . . ?
C9 C8 C13 C14 -177.2(6) . . . . ?
C7 C8 C13 C14 5.4(10) . . . . ?
C5 N1 C3 C2 159.1(5) . . . . ?
C6 N1 C3 C2 -57.9(8) . . . . ?
C5 N1 C3 C7 35.8(6) . . . . ?
C6 N1 C3 C7 178.8(6) . . . . ?
C1 C2 C3 N1 95.9(8) . . . . ?
C14 C2 C3 N1 -81.9(8) . . . . ?
C1 C2 C3 C7 -150.0(7) . . . . ?
C14 C2 C3 C7 32.2(10) . . . . ?
N2 C7 C3 N1 -37.3(6) . . . . ?
C8 C7 C3 N1 82.0(6) . . . . ?
N2 C7 C3 C2 -159.2(6) . . . . ?
C8 C7 C3 C2 -39.9(8) . . . . ?
C11 C10 C9 C8 -1.3(10) . . . . ?
C13 C8 C9 C10 -1.9(10) . . . . ?
C7 C8 C9 C10 175.5(6) . . . . ?
C9 C10 C11 C12 3.2(11) . . . . ?
C10 C11 C12 C13 -1.8(11) . . . . ?
C8 C13 C12 C11 -1.5(11) . . . . ?
C14 C13 C12 C11 179.0(7) . . . . ?
C17 C16 C15 C14 1.2(12) . . . . ?
C16 C15 C14 C2 -1.4(11) . . . . ?
C16 C15 C14 C13 -180.0(7) . . . . ?
C1 C2 C14 C15 -0.2(10) . . . . ?
C3 C2 C14 C15 177.7(7) . . . . ?
C1 C2 C14 C13 178.3(7) . . . . ?
C3 C2 C14 C13 -3.7(11) . . . . ?
C12 C13 C14 C15 -17.8(11) . . . . ?
C8 C13 C14 C15 162.8(7) . . . . ?
C12 C13 C14 C2 163.7(7) . . . . ?
C8 C13 C14 C2 -15.8(10) . . . . ?

_refine_diff_density_max         1.179
_refine_diff_density_min         -1.465
_refine_diff_density_rms         0.126

