# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_AB190623_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2306269'
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C20 H12 Br N O3'
_chemical_formula_sum            'C20 H12 Br N O3'
_chemical_formula_weight         394.227
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.47(3)
_cell_length_b                   15.27(2)
_cell_length_c                   6.904(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.65(7)
_cell_angle_gamma                90
_cell_volume                     1706(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4321
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      25.139
_cell_measurement_theta_min      2.533
_exptl_absorpt_coefficient_mu    2.428
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1723 before and 0.0905 after correction.
The Ratio of minimum to maximum transmission is 0.4040.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             791.684
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.9926
_diffrn_reflns_Laue_measured_fraction_max 0.9804
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19041
_diffrn_reflns_point_group_measured_fraction_full 0.9926
_diffrn_reflns_point_group_measured_fraction_max 0.9804
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.27
_diffrn_reflns_theta_min         2.52
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9926
_diffrn_measured_fraction_theta_max 0.9804
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2081
_reflns_number_total             3751
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.9564
_refine_diff_density_min         -0.9213
_refine_diff_density_rms         0.1290
_refine_ls_d_res_high            0.7756
_refine_ls_d_res_low             8.0920
_refine_ls_goodness_of_fit_ref   1.0367
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.0367
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1268P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2357
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00B(H00B), C00E(H00E), C00G(H00G), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P)
2.b Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
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_refinement_flags_posn
Br01 Br 0.03101(4) 0.38376(5) 0.55291(15) 0.1298(5) Uani 1.000000 .
O002 O 0.53118(18) 0.67919(17) 0.8751(5) 0.0568(8) Uani 1.000000 .
H002 H 0.5376(10) 0.7319(4) 0.895(7) 0.0852(12) Uiso 1.000000 GR
O003 O 0.5538(2) 0.4831(2) 0.8006(5) 0.0684(9) Uani 1.000000 .
O004 O 0.4369(2) 0.3516(2) 0.6043(5) 0.0751(10) Uani 1.000000 .
N005 N 0.3448(2) 0.4685(2) 0.5712(5) 0.0482(8) Uani 1.000000 .
C006 C 0.2899(2) 0.6219(2) 0.5805(5) 0.0353(8) Uani 1.000000 .
H006 H 0.2372(2) 0.6079(2) 0.5130(5) 0.0424(10) Uiso 1.000000 R
C007 C 0.3113(2) 0.7088(2) 0.6441(4) 0.0344(8) Uani 1.000000 .
C008 C 0.2467(2) 0.7789(2) 0.6085(4) 0.0367(8) Uani 1.000000 .
C009 C 0.3917(2) 0.7288(2) 0.7411(5) 0.0377(8) Uani 1.000000 .
H009 H 0.4047(2) 0.7861(2) 0.7805(5) 0.0453(10) Uiso 1.000000 R
C00A C 0.3505(2) 0.5595(2) 0.6234(5) 0.0401(9) Uani 1.000000 .
C00B C 0.2684(3) 0.8654(2) 0.5719(5) 0.0443(9) Uani 1.000000 .
H00B H 0.3231(3) 0.8795(2) 0.5689(5) 0.0531(11) Uiso 1.000000 R
C00C C 0.4529(2) 0.6636(2) 0.7798(5) 0.0408(9) Uani 1.000000 .
C00D C 0.4316(2) 0.5779(2) 0.7228(5) 0.0410(9) Uani 1.000000 .
C00E C 0.1636(3) 0.7596(3) 0.6134(5) 0.0482(10) Uani 1.000000 .
H00E H 0.1485(3) 0.7025(3) 0.6376(5) 0.0579(12) Uiso 1.000000 R
C00F C 0.4812(3) 0.4983(3) 0.7342(6) 0.0486(10) Uani 1.000000 .
C00G C 0.2079(3) 0.9298(3) 0.5402(6) 0.0576(12) Uani 1.000000 .
H00G H 0.2225(3) 0.9871(3) 0.5164(6) 0.0691(14) Uiso 1.000000 R
C00H C 0.2724(3) 0.4237(2) 0.4688(6) 0.0526(11) Uani 1.000000 .
C00I C 0.1992(3) 0.4281(3) 0.5405(7) 0.0599(12) Uani 1.000000 .
H00I H 0.1961(3) 0.4609(3) 0.6523(7) 0.0719(15) Uiso 1.000000 R
C00J C 0.4207(3) 0.4279(3) 0.6300(6) 0.0530(11) Uani 1.000000 .
C00K C 0.1036(3) 0.8248(3) 0.5826(7) 0.0645(13) Uani 1.000000 .
H00K H 0.0489(3) 0.8114(3) 0.5881(7) 0.0773(15) Uiso 1.000000 R
C00L C 0.2779(4) 0.3753(3) 0.3024(7) 0.0740(16) Uani 1.000000 .
H00L H 0.3272(4) 0.3730(3) 0.2549(7) 0.089(2) Uiso 1.000000 R
C00M C 0.1256(4) 0.9098(3) 0.5438(7) 0.0712(14) Uani 1.000000 .
H00M H 0.0855(4) 0.9534(3) 0.5201(7) 0.0855(17) Uiso 1.000000 R
C00N C 0.1308(4) 0.3826(3) 0.4430(10) 0.0831(18) Uani 1.000000 .
C00O C 0.2091(6) 0.3304(4) 0.2079(10) 0.102(2) Uani 1.000000 .
H00O H 0.2123(6) 0.2973(4) 0.0965(10) 0.122(3) Uiso 1.000000 R
C00P C 0.1340(5) 0.3344(4) 0.2784(11) 0.107(3) Uani 1.000000 .
H00P H 0.0875(5) 0.3046(4) 0.2138(11) 0.129(3) Uiso 1.000000 R


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
Br01 C00N 1.933(7) . ?
O002 H002 0.8200 . ?
O002 C00C 1.356(5) . ?
O003 C00F 1.221(5) . ?
O004 C00J 1.216(5) . ?
N005 C00A 1.434(5) . ?
N005 C00H 1.441(6) . ?
N005 C00J 1.388(6) . ?
C006 H006 0.9300 . ?
C006 C007 1.422(5) . ?
C006 C00A 1.372(5) . ?
C007 C008 1.496(5) . ?
C007 C009 1.402(5) . ?
C008 C00B 1.404(5) . ?
C008 C00E 1.406(6) . ?
C009 H009 0.9300 . ?
C009 C00C 1.406(5) . ?
C00A C00D 1.413(6) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.388(6) . ?
C00C C00D 1.392(5) . ?
C00D C00F 1.458(5) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.390(6) . ?
C00F C00J 1.549(6) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.395(7) . ?
C00H C00I 1.386(7) . ?
C00H C00L 1.384(6) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.388(7) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.387(7) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.380(9) . ?
C00M H00M 0.9300 . ?
C00N C00P 1.363(10) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.412(11) . ?
C00P H00P 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
C00C O002 H002 109.5 . . ?
C00H N005 C00A 126.4(3) . . ?
C00J N005 C00A 110.2(3) . . ?
C00J N005 C00H 123.4(3) . . ?
C007 C006 H006 121.6(2) . . ?
C00A C006 H006 121.6(2) . . ?
C00A C006 C007 116.9(3) . . ?
C008 C007 C006 119.2(3) . . ?
C009 C007 C006 120.6(3) . . ?
C009 C007 C008 120.2(3) . . ?
C00B C008 C007 120.3(3) . . ?
C00E C008 C007 120.8(3) . . ?
C00E C008 C00B 118.8(4) . . ?
H009 C009 C007 119.4(2) . . ?
C00C C009 C007 121.2(3) . . ?
C00C C009 H009 119.4(2) . . ?
C006 C00A N005 127.3(4) . . ?
C00D C00A N005 109.1(3) . . ?
C00D C00A C006 123.5(3) . . ?
H00B C00B C008 120.1(2) . . ?
C00G C00B C008 119.7(4) . . ?
C00G C00B H00B 120.1(3) . . ?
C009 C00C O002 123.5(3) . . ?
C00D C00C O002 118.0(3) . . ?
C00D C00C C009 118.5(3) . . ?
C00C C00D C00A 119.3(3) . . ?
C00F C00D C00A 109.3(3) . . ?
C00F C00D C00C 131.2(4) . . ?
H00E C00E C008 119.5(2) . . ?
C00K C00E C008 121.0(4) . . ?
C00K C00E H00E 119.5(3) . . ?
C00D C00F O003 132.7(4) . . ?
C00J C00F O003 122.9(4) . . ?
C00J C00F C00D 104.4(3) . . ?
H00G C00G C00B 119.5(3) . . ?
C00M C00G C00B 120.9(4) . . ?
C00M C00G H00G 119.5(3) . . ?
C00I C00H N005 119.8(4) . . ?
C00L C00H N005 119.1(5) . . ?
C00L C00H C00I 121.1(5) . . ?
H00I C00I C00H 120.5(3) . . ?
C00N C00I C00H 119.0(5) . . ?
C00N C00I H00I 120.5(4) . . ?
N005 C00J O004 126.5(4) . . ?
C00F C00J O004 126.4(4) . . ?
C00F C00J N005 107.0(3) . . ?
H00K C00K C00E 120.2(3) . . ?
C00M C00K C00E 119.7(5) . . ?
C00M C00K H00K 120.2(3) . . ?
H00L C00L C00H 120.5(3) . . ?
C00O C00L C00H 118.9(6) . . ?
C00O C00L H00L 120.5(5) . . ?
C00K C00M C00G 119.9(4) . . ?
H00M C00M C00G 120.1(3) . . ?
H00M C00M C00K 120.1(3) . . ?
C00I C00N Br01 118.6(5) . . ?
C00P C00N Br01 119.9(5) . . ?
C00P C00N C00I 121.4(7) . . ?
H00O C00O C00L 119.6(5) . . ?
C00P C00O C00L 120.7(6) . . ?
C00P C00O H00O 119.6(4) . . ?
C00O C00P C00N 118.8(6) . . ?
H00P C00P C00N 120.6(5) . . ?
H00P C00P C00O 120.6(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
Br01 C00N C00I C00H 176.5(3) . . . . ?
Br01 C00N C00P C00O -176.3(5) . . . . ?
O002 C00C C009 C007 -179.2(3) . . . . ?
O002 C00C C00D C00A 179.9(3) . . . . ?
O002 C00C C00D C00F -5.0(5) . . . . ?
O003 C00F C00D C00A 177.8(5) . . . . ?
O003 C00F C00D C00C 2.3(6) . . . . ?
O003 C00F C00J O004 1.0(5) . . . . ?
O003 C00F C00J N005 -178.9(4) . . . . ?
O004 C00J N005 C00A -178.5(4) . . . . ?
O004 C00J N005 C00H 0.2(6) . . . . ?
O004 C00J C00F C00D 179.1(5) . . . . ?
N005 C00A C006 C007 -178.4(3) . . . . ?
N005 C00A C00D C00C 177.0(3) . . . . ?
N005 C00A C00D C00F 1.0(3) . . . . ?
N005 C00H C00I C00N -178.3(4) . . . . ?
N005 C00H C00L C00O 178.2(4) . . . . ?
N005 C00J C00F C00D -0.7(3) . . . . ?
C006 C007 C008 C00B -147.2(3) . . . . ?
C006 C007 C008 C00E 33.6(4) . . . . ?
C006 C007 C009 C00C -0.6(4) . . . . ?
C006 C00A C00D C00C -0.8(4) . . . . ?
C006 C00A C00D C00F -176.8(4) . . . . ?
C007 C008 C00B C00G -179.6(3) . . . . ?
C007 C008 C00E C00K 179.2(3) . . . . ?
C007 C009 C00C C00D -1.2(4) . . . . ?
C008 C00B C00G C00M -0.2(4) . . . . ?
C008 C00E C00K C00M 0.9(4) . . . . ?
C009 C00C C00D C00A 1.8(4) . . . . ?
C009 C00C C00D C00F 176.9(3) . . . . ?
C00A C00D C00F C00J -0.2(3) . . . . ?
C00B C00G C00M C00K 1.1(5) . . . . ?
C00C C00D C00F C00J -175.6(5) . . . . ?
C00E C00K C00M C00G -1.5(5) . . . . ?
C00H C00I C00N C00P -0.3(5) . . . . ?
C00H C00L C00O C00P 0.6(5) . . . . ?
C00I C00N C00P C00O 0.5(6) . . . . ?
C00L C00O C00P C00N -0.7(7) . . . . ?


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

data_gs-s-135
_database_code_depnum_ccdc_archive 'CCDC 2306506'
_audit_update_record             
;
2023-11-08 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-10-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   22.7753(7)
_cell_length_b                   9.6966(3)
_cell_length_c                   17.8720(9)
_cell_angle_alpha                90
_cell_angle_beta                 126.1900(10)
_cell_angle_gamma                90
_cell_volume                     3185.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9447
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.63
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.5621
_exptl_absorpt_correction_T_min  0.4944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1620 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.8796.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32298
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_min         2.405
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  "'Bruker D8 QUEST SCXRD"
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2301
_reflns_number_total             3024
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+3.5196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31378(15) 0.1551(4) 0.11106(18) 0.0772(10) Uani 1 1 d . . . . .
H1A H 0.321362 0.157733 0.063640 0.116 Uiso 1 1 calc R U . . .
H1B H 0.278927 0.224315 0.098675 0.116 Uiso 1 1 calc R U . . .
H1C H 0.295850 0.065858 0.111681 0.116 Uiso 1 1 calc R U . . .
C2 C 0.26944(15) 0.3005(3) 0.3436(2) 0.0715(9) Uani 1 1 d . . . . .
H2A H 0.288822 0.387044 0.341449 0.107 Uiso 1 1 calc R U . . .
H2B H 0.265700 0.300991 0.394399 0.107 Uiso 1 1 calc R U . . .
H2C H 0.222087 0.286736 0.286599 0.107 Uiso 1 1 calc R U . . .
C3 C 0.29207(15) 0.0455(3) 0.3681(2) 0.0713(9) Uani 1 1 d . . . . .
H3A H 0.243877 0.028263 0.313397 0.107 Uiso 1 1 calc R U . . .
H3B H 0.290976 0.050859 0.420931 0.107 Uiso 1 1 calc R U . . .
H3C H 0.323716 -0.028248 0.376877 0.107 Uiso 1 1 calc R U . . .
C4 C 0.32038(12) 0.1826(3) 0.35722(17) 0.0495(6) Uani 1 1 d . . . . .
C5 C 0.31977(13) 0.1751(3) 0.27258(16) 0.0492(6) Uani 1 1 d . . . . .
H5 H 0.275237 0.161327 0.215533 0.059 Uiso 1 1 calc R U . . .
C6 C 0.37840(12) 0.1869(2) 0.27372(16) 0.0426(6) Uani 1 1 d . . . . .
C7 C 0.44886(12) 0.2106(2) 0.36011(15) 0.0390(5) Uani 1 1 d . . . . .
C8 C 0.45217(12) 0.2222(2) 0.44341(15) 0.0410(5) Uani 1 1 d . . . . .
C9 C 0.39471(12) 0.2097(3) 0.44484(17) 0.0468(6) Uani 1 1 d . . . . .
H9 H 0.400599 0.217918 0.500765 0.056 Uiso 1 1 calc R U . . .
C10 C 0.51640(12) 0.2260(2) 0.38305(16) 0.0443(6) Uani 1 1 d . . . . .
H10 H 0.529061 0.220635 0.342278 0.053 Uiso 1 1 calc R U . . .
C11 C 0.56687(12) 0.2528(3) 0.48321(16) 0.0457(6) Uani 1 1 d . . . . .
C12 C 0.55031(11) 0.2742(2) 0.60966(15) 0.0411(5) Uani 1 1 d . . . . .
C13 C 0.56670(14) 0.4054(3) 0.64507(17) 0.0514(6) Uani 1 1 d . . . . .
H13 H 0.563355 0.478212 0.608877 0.062 Uiso 1 1 calc R U . . .
C14 C 0.58815(13) 0.4303(3) 0.73411(17) 0.0521(6) Uani 1 1 d . . . . .
H14 H 0.599042 0.519705 0.757474 0.063 Uiso 1 1 calc R U . . .
C15 C 0.59341(12) 0.3233(3) 0.78809(16) 0.0450(6) Uani 1 1 d . . . . .
C16 C 0.57713(13) 0.1908(3) 0.75267(17) 0.0506(6) Uani 1 1 d . . . . .
H16 H 0.580670 0.117943 0.788952 0.061 Uiso 1 1 calc R U . . .
C17 C 0.55576(13) 0.1664(3) 0.66419(17) 0.0480(6) Uani 1 1 d . . . . .
H17 H 0.544901 0.076983 0.640808 0.058 Uiso 1 1 calc R U . . .
C18 C 0.62479(18) 0.4718(3) 0.9124(2) 0.0781(9) Uani 1 1 d . . . . .
H18A H 0.580711 0.523505 0.872703 0.117 Uiso 1 1 calc R U . . .
H18B H 0.663634 0.516098 0.914987 0.117 Uiso 1 1 calc R U . . .
H18C H 0.636663 0.467476 0.973614 0.117 Uiso 1 1 calc R U . . .
N1 N 0.52522(9) 0.2489(2) 0.51640(13) 0.0446(5) Uani 1 1 d . . . . .
O1 O 0.38107(9) 0.1812(2) 0.19917(11) 0.0556(5) Uani 1 1 d . . . . .
O2 O 0.63224(9) 0.2763(2) 0.53077(12) 0.0602(5) Uani 1 1 d . . . . .
O3 O 0.61500(10) 0.3366(2) 0.87700(12) 0.0629(5) 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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.429(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C4 1.542(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.539(4) . ?
C4 C5 1.506(3) . ?
C4 C9 1.502(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.328(3) . ?
C6 C7 1.444(3) . ?
C6 O1 1.370(3) . ?
C7 C8 1.450(3) . ?
C7 C10 1.346(3) . ?
C8 C9 1.329(3) . ?
C8 N1 1.405(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.471(3) . ?
C11 N1 1.385(3) . ?
C11 O2 1.223(3) . ?
C12 C13 1.371(3) . ?
C12 C17 1.384(3) . ?
C12 N1 1.428(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(3) . ?
C15 C16 1.382(3) . ?
C15 O3 1.364(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 O3 1.415(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C3 C4 C2 109.1(2) . . ?
C5 C4 C2 108.5(2) . . ?
C5 C4 C3 109.2(2) . . ?
C9 C4 C2 108.3(2) . . ?
C9 C4 C3 108.5(2) . . ?
C9 C4 C5 113.1(2) . . ?
C4 C5 H5 117.7 . . ?
C6 C5 C4 124.6(2) . . ?
C6 C5 H5 117.7 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 O1 127.1(2) . . ?
O1 C6 C7 112.74(19) . . ?
C6 C7 C8 117.46(19) . . ?
C10 C7 C6 133.8(2) . . ?
C10 C7 C8 108.8(2) . . ?
C9 C8 C7 123.9(2) . . ?
C9 C8 N1 129.7(2) . . ?
N1 C8 C7 106.42(18) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C7 C10 H10 125.6 . . ?
C7 C10 C11 108.8(2) . . ?
C11 C10 H10 125.6 . . ?
N1 C11 C10 106.02(19) . . ?
O2 C11 C10 129.4(2) . . ?
O2 C11 N1 124.6(2) . . ?
C13 C12 C17 119.3(2) . . ?
C13 C12 N1 120.7(2) . . ?
C17 C12 N1 120.0(2) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 119.5(2) . . ?
O3 C15 C14 124.7(2) . . ?
O3 C15 C16 115.9(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
C8 N1 C12 123.61(18) . . ?
C11 N1 C8 110.03(19) . . ?
C11 N1 C12 126.31(18) . . ?
C6 O1 C1 116.37(19) . . ?
C15 O3 C18 117.5(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
C2 C4 C5 C6 122.1(3) . . . . ?
C2 C4 C9 C8 -121.5(3) . . . . ?
C3 C4 C5 C6 -119.1(3) . . . . ?
C3 C4 C9 C8 120.1(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 O1 -179.9(2) . . . . ?
C5 C4 C9 C8 -1.2(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C7 C10 179.7(3) . . . . ?
C5 C6 O1 C1 -2.3(4) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C6 C7 C8 N1 -178.27(19) . . . . ?
C6 C7 C10 C11 178.0(2) . . . . ?
C7 C6 O1 C1 178.8(2) . . . . ?
C7 C8 C9 C4 -0.3(4) . . . . ?
C7 C8 N1 C11 -0.7(3) . . . . ?
C7 C8 N1 C12 176.7(2) . . . . ?
C7 C10 C11 N1 1.2(3) . . . . ?
C7 C10 C11 O2 -177.7(3) . . . . ?
C8 C7 C10 C11 -1.7(3) . . . . ?
C9 C4 C5 C6 1.9(4) . . . . ?
C9 C8 N1 C11 179.8(3) . . . . ?
C9 C8 N1 C12 -2.9(4) . . . . ?
C10 C7 C8 C9 -178.9(2) . . . . ?
C10 C7 C8 N1 1.5(3) . . . . ?
C10 C11 N1 C8 -0.3(3) . . . . ?
C10 C11 N1 C12 -177.6(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
C13 C12 N1 C8 -103.5(3) . . . . ?
C13 C12 N1 C11 73.4(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 O3 179.0(2) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C14 C15 O3 C18 7.4(4) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
C16 C15 O3 C18 -173.5(2) . . . . ?
C17 C12 C13 C14 -0.3(4) . . . . ?
C17 C12 N1 C8 74.1(3) . . . . ?
C17 C12 N1 C11 -109.0(3) . . . . ?
N1 C8 C9 C4 179.2(2) . . . . ?
N1 C12 C13 C14 177.4(2) . . . . ?
N1 C12 C17 C16 -177.5(2) . . . . ?
O1 C6 C7 C8 178.4(2) . . . . ?
O1 C6 C7 C10 -1.3(4) . . . . ?
O2 C11 N1 C8 178.7(2) . . . . ?
O2 C11 N1 C12 1.4(4) . . . . ?
O3 C15 C16 C17 -179.2(2) . . . . ?

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

data_kpgss2
_database_code_depnum_ccdc_archive 'CCDC 2306270'
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Br N O2'
_chemical_formula_sum            'C16 H16 Br N O2'
_chemical_formula_weight         334.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.3095(2)
_cell_length_b                   10.9116(2)
_cell_length_c                   13.1608(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.8270(10)
_cell_angle_gamma                90
_cell_volume                     1474.00(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.525
_shelx_estimated_absorpt_T_min   0.367
_exptl_absorpt_coefficient_mu    2.789
_exptl_absorpt_correction_T_max  0.5635
_exptl_absorpt_correction_T_min  0.3048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1150 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.5409.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.265
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            58867
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.753
_diffrn_reflns_theta_min         1.984
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST SC-XRD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2894
_reflns_number_total             3816
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.8127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.15103(3) 0.40426(3) 0.97916(2) 0.06455(11) Uani 1 1 d . . . . .
O1 O 0.09976(17) 0.37445(15) 0.56726(15) 0.0593(4) Uani 1 1 d . . . . .
O2 O 0.40835(19) 0.59062(15) 0.38820(15) 0.0630(5) Uani 1 1 d . . . . .
N1 N 0.20361(15) 0.56111(14) 0.62419(13) 0.0361(3) Uani 1 1 d . . . . .
C1 C 0.1691(2) 0.45427(19) 0.55913(17) 0.0428(4) Uani 1 1 d . . . . .
C2 C 0.2346(2) 0.4620(2) 0.47976(18) 0.0483(5) Uani 1 1 d . . . . .
H2A H 0.295240 0.394813 0.491954 0.058 Uiso 1 1 calc R U . . .
H2B H 0.170831 0.460903 0.402352 0.058 Uiso 1 1 calc R U . . .
C3 C 0.3042(2) 0.58213(18) 0.50911(16) 0.0399(4) Uani 1 1 d . . . . .
C4 C 0.28412(18) 0.63536(17) 0.59259(15) 0.0343(4) Uani 1 1 d . . . . .
C5 C 0.3852(2) 0.6391(2) 0.46156(17) 0.0440(5) Uani 1 1 d . . . . .
C6 C 0.4349(2) 0.76541(19) 0.50507(18) 0.0460(5) Uani 1 1 d . . . . .
H6A H 0.371283 0.825043 0.459113 0.055 Uiso 1 1 calc R U . . .
H6B H 0.514558 0.779577 0.496017 0.055 Uiso 1 1 calc R U . . .
C7 C 0.46237(19) 0.78858(18) 0.62820(17) 0.0407(4) Uani 1 1 d . . . . .
C8 C 0.4904(2) 0.9248(2) 0.6556(2) 0.0549(6) Uani 1 1 d . . . . .
H8A H 0.414427 0.971963 0.611308 0.082 Uiso 1 1 calc R U . . .
H8B H 0.561797 0.949860 0.639127 0.082 Uiso 1 1 calc R U . . .
H8C H 0.512419 0.938077 0.733606 0.082 Uiso 1 1 calc R U . . .
C9 C 0.5793(2) 0.7125(2) 0.7044(2) 0.0553(6) Uani 1 1 d . . . . .
H9A H 0.594824 0.725912 0.781053 0.083 Uiso 1 1 calc R U . . .
H9B H 0.654828 0.736544 0.693520 0.083 Uiso 1 1 calc R U . . .
H9C H 0.561760 0.627222 0.686487 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3406(2) 0.75367(18) 0.64728(17) 0.0409(4) Uani 1 1 d . . . . .
H10A H 0.364411 0.747464 0.727007 0.049 Uiso 1 1 calc R U . . .
H10B H 0.275609 0.817730 0.617337 0.049 Uiso 1 1 calc R U . . .
C11 C 0.15887(17) 0.58823(17) 0.70827(16) 0.0351(4) Uani 1 1 d . . . . .
C12 C 0.17063(18) 0.49902(18) 0.78713(16) 0.0378(4) Uani 1 1 d . . . . .
H12 H 0.206275 0.422789 0.784946 0.045 Uiso 1 1 calc R U . . .
C13 C 0.12814(19) 0.5260(2) 0.86912(17) 0.0433(5) Uani 1 1 d . . . . .
C14 C 0.0741(2) 0.6375(2) 0.87376(19) 0.0508(5) Uani 1 1 d . . . . .
H14 H 0.045932 0.653898 0.929386 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0625(2) 0.7247(2) 0.7941(2) 0.0517(5) Uani 1 1 d . . . . .
H15 H 0.026204 0.800606 0.796227 0.062 Uiso 1 1 calc R U . . .
C16 C 0.1042(2) 0.7006(2) 0.71109(18) 0.0442(5) Uani 1 1 d . . . . .
H16 H 0.095426 0.759736 0.657532 0.053 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 C13 1.901(2) . ?
O1 C1 1.206(2) . ?
O2 C5 1.222(2) . ?
N1 C1 1.401(3) . ?
N1 C4 1.406(2) . ?
N1 C11 1.428(2) . ?
C1 C2 1.515(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.494(3) . ?
C3 C4 1.344(3) . ?
C3 C5 1.449(3) . ?
C4 C10 1.485(3) . ?
C5 C6 1.508(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.537(3) . ?
C7 C8 1.531(3) . ?
C7 C9 1.526(3) . ?
C7 C10 1.548(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.388(3) . ?
C11 C16 1.380(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(3) . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 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 N1 C4 110.33(15) . . ?
C1 N1 C11 123.20(15) . . ?
C4 N1 C11 126.45(15) . . ?
O1 C1 N1 124.83(19) . . ?
O1 C1 C2 128.69(19) . . ?
N1 C1 C2 106.48(16) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 C1 103.15(16) . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C4 C3 C2 109.81(17) . . ?
C4 C3 C5 121.49(19) . . ?
C5 C3 C2 128.69(17) . . ?
N1 C4 C10 123.90(16) . . ?
C3 C4 N1 110.22(17) . . ?
C3 C4 C10 125.86(17) . . ?
O2 C5 C3 122.7(2) . . ?
O2 C5 C6 121.79(19) . . ?
C3 C5 C6 115.49(17) . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C5 C6 C7 115.41(16) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C6 C7 C10 109.30(16) . . ?
C8 C7 C6 109.77(18) . . ?
C8 C7 C10 108.10(17) . . ?
C9 C7 C6 109.83(18) . . ?
C9 C7 C8 109.69(18) . . ?
C9 C7 C10 110.13(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 C7 111.48(16) . . ?
C4 C10 H10A 109.3 . . ?
C4 C10 H10B 109.3 . . ?
C7 C10 H10A 109.3 . . ?
C7 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 N1 118.70(17) . . ?
C16 C11 N1 120.89(17) . . ?
C16 C11 C12 120.40(17) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.56(19) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 Br1 117.68(16) . . ?
C14 C13 Br1 120.36(15) . . ?
C14 C13 C12 121.94(19) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.59(19) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.7(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?

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
Br1 C13 C14 C15 178.20(17) . . . . ?
O1 C1 C2 C3 179.1(2) . . . . ?
O2 C5 C6 C7 -149.6(2) . . . . ?
N1 C1 C2 C3 -0.5(2) . . . . ?
N1 C4 C10 C7 158.08(18) . . . . ?
N1 C11 C12 C13 179.47(17) . . . . ?
N1 C11 C16 C15 -179.53(19) . . . . ?
C1 N1 C4 C3 0.1(2) . . . . ?
C1 N1 C4 C10 -178.33(19) . . . . ?
C1 N1 C11 C12 49.7(3) . . . . ?
C1 N1 C11 C16 -129.9(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 C5 179.4(2) . . . . ?
C2 C3 C4 N1 -0.4(2) . . . . ?
C2 C3 C4 C10 177.9(2) . . . . ?
C2 C3 C5 O2 -1.2(4) . . . . ?
C2 C3 C5 C6 176.3(2) . . . . ?
C3 C4 C10 C7 -20.1(3) . . . . ?
C3 C5 C6 C7 32.9(3) . . . . ?
C4 N1 C1 O1 -179.3(2) . . . . ?
C4 N1 C1 C2 0.3(2) . . . . ?
C4 N1 C11 C12 -131.7(2) . . . . ?
C4 N1 C11 C16 48.7(3) . . . . ?
C4 C3 C5 O2 177.5(2) . . . . ?
C4 C3 C5 C6 -5.0(3) . . . . ?
C5 C3 C4 N1 -179.35(18) . . . . ?
C5 C3 C4 C10 -1.0(3) . . . . ?
C5 C6 C7 C8 -170.83(18) . . . . ?
C5 C6 C7 C9 68.5(2) . . . . ?
C5 C6 C7 C10 -52.4(2) . . . . ?
C6 C7 C10 C4 44.1(2) . . . . ?
C8 C7 C10 C4 163.59(18) . . . . ?
C9 C7 C10 C4 -76.6(2) . . . . ?
C11 N1 C1 O1 -0.5(3) . . . . ?
C11 N1 C1 C2 179.11(17) . . . . ?
C11 N1 C4 C3 -178.68(18) . . . . ?
C11 N1 C4 C10 2.9(3) . . . . ?
C11 C12 C13 Br1 -177.82(14) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C16 C11 C12 C13 -0.9(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
