# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_sgdp_409_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2292970'
loop_
_audit_author_name
_audit_author_address
'Subhash Chandra Ghosh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2025-01-30 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_audit_creation_date             2025-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O4'
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3356(4)
_cell_length_b                   12.1862(6)
_cell_length_c                   16.2134(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.601(2)
_cell_angle_gamma                90
_cell_volume                     1444.70(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.362
_cell_measurement_theta_min      3.249
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1290 before and 0.0861 after correction. The Ratio of minimum to maximum transmission is 0.7990. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            98963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         3.025
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3829
_reflns_number_total             4431
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.096
_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)+(0.0634P)²+0.4083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1438
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O4 O 0.40858(17) 0.84490(10) 0.35439(6) 0.0543(3) Uani 1 1 d . . . . .
O2 O 0.19249(13) 0.60055(10) 0.37917(8) 0.0547(3) Uani 1 1 d . . . . .
O3 O 0.82492(19) 0.82349(9) 0.50982(7) 0.0590(3) Uani 1 1 d . . . . .
O1 O 0.84922(19) 0.70306(10) 0.61352(6) 0.0562(3) Uani 1 1 d . . . . .
N1 N 0.47874(13) 0.65629(8) 0.43064(6) 0.0335(2) Uani 1 1 d . . . . .
N2 N 0.37746(14) 0.83959(9) 0.43179(7) 0.0356(2) Uani 1 1 d . . . . .
C1 C 0.8604(3) 0.79250(17) 0.67206(11) 0.0689(5) Uani 1 1 d . . . . .
H1A H 0.953335 0.843110 0.658033 0.103 Uiso 1 1 calc GR . . . .
H1B H 0.890611 0.764272 0.726732 0.103 Uiso 1 1 calc GR . . . .
H1C H 0.744734 0.829613 0.670359 0.103 Uiso 1 1 calc GR . . . .
C2 C 0.82826(18) 0.73043(11) 0.53439(8) 0.0384(3) Uani 1 1 d . . . . .
C3 C 0.80855(17) 0.63071(10) 0.47936(8) 0.0358(3) Uani 1 1 d . . . . .
H3A H 0.770550 0.568605 0.511246 0.043 Uiso 1 1 calc R . . . .
H3B H 0.926063 0.613165 0.459196 0.043 Uiso 1 1 calc R . . . .
C4 C 0.66923(15) 0.64985(10) 0.40627(7) 0.0302(2) Uani 1 1 d . . . . .
H4 H 0.699206 0.718018 0.378287 0.036 Uiso 1 1 calc R . . . .
C5 C 0.41362(15) 0.74466(10) 0.47528(7) 0.0319(2) Uani 1 1 d . . . . .
C6 C 0.3093(2) 0.92693(12) 0.47076(10) 0.0483(3) Uani 1 1 d . . . . .
H6 H 0.281765 0.990875 0.441024 0.058 Uiso 1 1 calc R . . . .
C7 C 0.2801(3) 0.92305(14) 0.55280(11) 0.0576(4) Uani 1 1 d . . . . .
H7 H 0.233562 0.984111 0.578368 0.069 Uiso 1 1 calc R . . . .
C8 C 0.35741(16) 0.59641(10) 0.37872(8) 0.0345(2) Uani 1 1 d . . . . .
C9 C 0.47040(16) 0.52925(10) 0.32725(7) 0.0321(2) Uani 1 1 d . . . . .
C10 C 0.4152(2) 0.44979(12) 0.26916(9) 0.0425(3) Uani 1 1 d . . . . .
H10 H 0.292360 0.432212 0.257804 0.051 Uiso 1 1 calc R . . . .
C11 C 0.5502(2) 0.39783(13) 0.22886(9) 0.0497(3) Uani 1 1 d . . . . .
H11 H 0.517970 0.344194 0.189571 0.060 Uiso 1 1 calc R . . . .
C12 C 0.7325(2) 0.42453(14) 0.24618(9) 0.0499(3) Uani 1 1 d . . . . .
H12 H 0.820648 0.387782 0.218582 0.060 Uiso 1 1 calc R . . . .
C13 C 0.78748(19) 0.50492(12) 0.30381(9) 0.0427(3) Uani 1 1 d . . . . .
H13 H 0.910309 0.522556 0.315044 0.051 Uiso 1 1 calc R . . . .
C14 C 0.65237(16) 0.55780(10) 0.34392(7) 0.0312(2) Uani 1 1 d . . . . .
C15 C 0.3842(2) 0.73886(13) 0.55765(9) 0.0465(3) Uani 1 1 d . . . . .
H15 H 0.408066 0.673900 0.586644 0.056 Uiso 1 1 calc R . . . .
C16 C 0.3193(3) 0.82919(17) 0.59773(10) 0.0613(5) Uani 1 1 d . . . . .
H16 H 0.302576 0.826504 0.653940 0.074 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
O4 N2 1.2949(14) . ?
O2 C8 1.2114(15) . ?
O3 C2 1.2015(18) . ?
O1 C1 1.443(2) . ?
O1 C2 1.3226(17) . ?
N1 C4 1.4844(14) . ?
N1 C5 1.4026(15) . ?
N1 C8 1.3831(16) . ?
N2 C5 1.3696(15) . ?
N2 C6 1.3538(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.5077(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5194(16) . ?
C4 H4 0.9800 . ?
C4 C14 1.5085(16) . ?
C5 C15 1.3716(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.365(2) . ?
C7 H7 0.9300 . ?
C7 C16 1.374(3) . ?
C8 C9 1.4712(17) . ?
C9 C10 1.3884(17) . ?
C9 C14 1.3849(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.3870(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(2) . ?
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
C2 O1 C1 116.33(13) . . ?
C5 N1 C4 123.02(10) . . ?
C8 N1 C4 112.56(9) . . ?
C8 N1 C5 119.34(10) . . ?
O4 N2 C5 119.95(11) . . ?
O4 N2 C6 120.89(12) . . ?
C6 N2 C5 119.16(11) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 O1 123.87(13) . . ?
O3 C2 C3 124.48(13) . . ?
O1 C2 C3 111.65(12) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.37(10) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
N1 C4 C3 112.91(10) . . ?
N1 C4 H4 109.2 . . ?
N1 C4 C14 100.92(9) . . ?
C3 C4 H4 109.2 . . ?
C14 C4 C3 114.99(10) . . ?
C14 C4 H4 109.2 . . ?
N2 C5 N1 116.28(10) . . ?
N2 C5 C15 120.39(11) . . ?
C15 C5 N1 123.33(12) . . ?
N2 C6 H6 119.3 . . ?
N2 C6 C7 121.35(14) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C16 120.19(14) . . ?
C16 C7 H7 119.9 . . ?
O2 C8 N1 124.65(12) . . ?
O2 C8 C9 129.41(12) . . ?
N1 C8 C9 105.93(10) . . ?
C10 C9 C8 128.74(12) . . ?
C14 C9 C8 109.12(10) . . ?
C14 C9 C10 122.13(12) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 C9 117.30(13) . . ?
C11 C10 H10 121.3 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.93(13) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.69(14) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.2 . . ?
C14 C13 C12 117.56(13) . . ?
C14 C13 H13 121.2 . . ?
C9 C14 C4 110.09(10) . . ?
C9 C14 C13 120.37(11) . . ?
C13 C14 C4 129.53(11) . . ?
C5 C15 H15 119.9 . . ?
C5 C15 C16 120.24(14) . . ?
C16 C15 H15 119.9 . . ?
C7 C16 C15 118.63(14) . . ?
C7 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?

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
O4 N2 C5 N1 -1.88(17) . . . . ?
O4 N2 C5 C15 178.82(13) . . . . ?
O4 N2 C6 C7 -178.41(15) . . . . ?
O2 C8 C9 C10 -3.6(2) . . . . ?
O2 C8 C9 C14 175.52(14) . . . . ?
O3 C2 C3 C4 -38.08(19) . . . . ?
O1 C2 C3 C4 141.71(12) . . . . ?
N1 C4 C14 C9 8.08(12) . . . . ?
N1 C4 C14 C13 -173.26(13) . . . . ?
N1 C5 C15 C16 -179.84(15) . . . . ?
N1 C8 C9 C10 175.37(12) . . . . ?
N1 C8 C9 C14 -5.53(13) . . . . ?
N2 C5 C15 C16 -0.6(2) . . . . ?
N2 C6 C7 C16 -0.2(3) . . . . ?
C1 O1 C2 O3 2.7(2) . . . . ?
C1 O1 C2 C3 -177.06(14) . . . . ?
C2 C3 C4 N1 -69.93(13) . . . . ?
C2 C3 C4 C14 174.99(10) . . . . ?
C3 C4 C14 C9 129.89(11) . . . . ?
C3 C4 C14 C13 -51.44(18) . . . . ?
C4 N1 C5 N2 75.68(14) . . . . ?
C4 N1 C5 C15 -105.04(15) . . . . ?
C4 N1 C8 O2 -169.73(13) . . . . ?
C4 N1 C8 C9 11.25(13) . . . . ?
C5 N1 C4 C3 70.25(14) . . . . ?
C5 N1 C4 C14 -166.48(10) . . . . ?
C5 N1 C8 O2 -14.2(2) . . . . ?
C5 N1 C8 C9 166.80(10) . . . . ?
C5 N2 C6 C7 1.6(2) . . . . ?
C5 C15 C16 C7 1.9(3) . . . . ?
C6 N2 C5 N1 178.13(12) . . . . ?
C6 N2 C5 C15 -1.18(19) . . . . ?
C6 C7 C16 C15 -1.5(3) . . . . ?
C8 N1 C4 C3 -135.24(11) . . . . ?
C8 N1 C4 C14 -11.97(12) . . . . ?
C8 N1 C5 N2 -77.20(14) . . . . ?
C8 N1 C5 C15 102.08(15) . . . . ?
C8 C9 C10 C11 -179.87(13) . . . . ?
C8 C9 C14 C4 -2.01(13) . . . . ?
C8 C9 C14 C13 179.18(12) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C9 C14 C4 177.15(11) . . . . ?
C10 C9 C14 C13 -1.65(19) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C4 -177.58(13) . . . . ?
C12 C13 C14 C9 1.0(2) . . . . ?
C14 C9 C10 C11 1.1(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_sgdp_373_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2292973'
loop_
_audit_author_name
_audit_author_address
'Subhash Chandra Ghosh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2025-01-30 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_audit_creation_date             2023-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 Br F N2 O4'
_chemical_formula_sum            'C17 H14 Br F N2 O4'
_chemical_formula_weight         409.21
_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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9400(5)
_cell_length_b                   9.2953(5)
_cell_length_c                   11.9582(7)
_cell_angle_alpha                84.896(2)
_cell_angle_beta                 72.675(2)
_cell_angle_gamma                61.415(2)
_cell_volume                     831.31(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.506
_cell_measurement_theta_min      2.501
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.540
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1092 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.7311.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            58517
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.658
_diffrn_reflns_theta_min         2.500
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3836
_reflns_number_total             5132
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.040
_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)+(0.0485P)²+0.5711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C12(H12), C13(H13), C17(H17)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.40775(4) 0.35585(4) 0.60751(2) 0.06192(12) Uani 1 1 d . . . . .
O3 O 0.4990(2) 0.4033(3) 0.20088(19) 0.0653(6) Uani 1 1 d . . . . .
O1 O 0.5400(2) -0.0346(2) 0.14741(16) 0.0515(4) Uani 1 1 d . . . . .
O4 O -0.0057(2) 0.2400(3) 0.40234(15) 0.0534(4) Uani 1 1 d . . . . .
F1 F 0.86833(19) -0.1825(2) 0.22700(15) 0.0612(4) Uani 1 1 d . . . . .
N1 N 0.3220(2) 0.1846(2) 0.27856(15) 0.0358(4) Uani 1 1 d . . . . .
O2 O 0.2693(3) 0.6521(2) 0.2336(2) 0.0714(7) Uani 1 1 d . . . . .
N3 N 0.0266(2) 0.2563(2) 0.29004(16) 0.0389(4) Uani 1 1 d . . . . .
C1 C -0.0742(3) 0.3148(4) 0.1200(2) 0.0570(7) Uani 1 1 d . . . . .
H1 H -0.165328 0.342741 0.086477 0.068 Uiso 1 1 calc R . . . .
C2 C 0.0900(4) 0.2928(4) 0.0506(2) 0.0596(7) Uani 1 1 d . . . . .
H2 H 0.110999 0.305369 -0.029701 0.071 Uiso 1 1 calc R . . . .
C3 C 0.2224(3) 0.2516(3) 0.1030(2) 0.0497(5) Uani 1 1 d . . . . .
H3 H 0.334197 0.235540 0.057469 0.060 Uiso 1 1 calc R . . . .
C4 C 0.1903(3) 0.2340(3) 0.22214(19) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.3031(3) 0.2768(3) 0.38071(18) 0.0341(4) Uani 1 1 d . . . . .
H5 H 0.217349 0.264987 0.449168 0.041 Uiso 1 1 calc R . . . .
C6 C 0.2365(3) 0.4590(3) 0.36115(19) 0.0392(4) Uani 1 1 d . . . . .
H6A H 0.118488 0.504878 0.351491 0.047 Uiso 1 1 calc R . . . .
H6B H 0.225250 0.513370 0.431034 0.047 Uiso 1 1 calc R . . . .
C7 C 0.3528(3) 0.4975(3) 0.2569(2) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.3631(5) 0.7084(5) 0.1326(4) 0.0953(15) Uani 1 1 d . . . . .
H8A H 0.447782 0.729142 0.154110 0.114 Uiso 1 1 calc R . . . .
H8B H 0.428600 0.623588 0.069117 0.114 Uiso 1 1 calc R . . . .
C9 C 0.2405(6) 0.8537(6) 0.0947(4) 0.0894(12) Uani 1 1 d . . . . .
H9A H 0.303931 0.891350 0.030082 0.134 Uiso 1 1 calc GR . . . .
H9B H 0.174103 0.936786 0.158129 0.134 Uiso 1 1 calc GR . . . .
H9C H 0.160168 0.831654 0.070051 0.134 Uiso 1 1 calc GR . . . .
C10 C 0.4874(3) 0.1789(3) 0.39621(18) 0.0350(4) Uani 1 1 d . . . . .
C11 C 0.5536(3) 0.1929(3) 0.4832(2) 0.0407(4) Uani 1 1 d . . . . .
C12 C 0.7279(3) 0.0825(3) 0.4814(2) 0.0479(5) Uani 1 1 d . . . . .
H12 H 0.772799 0.092936 0.539260 0.058 Uiso 1 1 calc R . . . .
C13 C 0.8348(3) -0.0426(3) 0.3943(2) 0.0479(5) Uani 1 1 d . . . . .
H13 H 0.951675 -0.115426 0.392922 0.058 Uiso 1 1 calc R . . . .
C14 C 0.7669(3) -0.0583(3) 0.3099(2) 0.0429(5) Uani 1 1 d . . . . .
C15 C 0.5938(3) 0.0518(3) 0.31030(19) 0.0367(4) Uani 1 1 d . . . . .
C16 C 0.4921(3) 0.0550(3) 0.23198(19) 0.0375(4) Uani 1 1 d . . . . .
C17 C -0.1034(3) 0.2957(3) 0.2378(2) 0.0479(5) Uani 1 1 d . . . . .
H17 H -0.214427 0.309943 0.283465 0.057 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 C11 1.887(2) . ?
O3 C7 1.188(3) . ?
O1 C16 1.204(3) . ?
O4 N3 1.298(3) . ?
F1 C14 1.343(3) . ?
N1 C4 1.398(3) . ?
N1 C5 1.476(3) . ?
N1 C16 1.391(3) . ?
O2 C7 1.314(3) . ?
O2 C8 1.462(4) . ?
N3 C4 1.369(3) . ?
N3 C17 1.363(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(4) . ?
C1 C17 1.366(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.525(3) . ?
C5 C10 1.515(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.506(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.416(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.383(3) . ?
C10 C15 1.383(3) . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.476(3) . ?
C17 H17 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
C4 N1 C5 123.80(17) . . ?
C16 N1 C4 121.49(17) . . ?
C16 N1 C5 114.17(16) . . ?
C7 O2 C8 117.4(2) . . ?
O4 N3 C4 121.07(18) . . ?
O4 N3 C17 119.97(19) . . ?
C17 N3 C4 119.0(2) . . ?
C2 C1 H1 119.9 . . ?
C17 C1 H1 119.9 . . ?
C17 C1 C2 120.2(2) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
N3 C4 N1 116.79(18) . . ?
N3 C4 C3 120.3(2) . . ?
C3 C4 N1 122.77(19) . . ?
N1 C5 H5 108.6 . . ?
N1 C5 C6 112.07(17) . . ?
N1 C5 C10 100.90(16) . . ?
C6 C5 H5 108.6 . . ?
C10 C5 H5 108.6 . . ?
C10 C5 C6 117.65(17) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C5 115.06(18) . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
O3 C7 O2 123.4(2) . . ?
O3 C7 C6 126.0(2) . . ?
O2 C7 C6 110.6(2) . . ?
O2 C8 H8A 109.6 . . ?
O2 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 O2 110.3(3) . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 130.3(2) . . ?
C11 C10 C15 119.52(19) . . ?
C15 C10 C5 110.03(17) . . ?
C10 C11 Br1 120.77(17) . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 Br1 119.43(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
F1 C14 C13 119.7(2) . . ?
F1 C14 C15 119.7(2) . . ?
C13 C14 C15 120.6(2) . . ?
C10 C15 C14 120.2(2) . . ?
C10 C15 C16 110.01(18) . . ?
C14 C15 C16 129.8(2) . . ?
O1 C16 N1 126.0(2) . . ?
O1 C16 C15 129.2(2) . . ?
N1 C16 C15 104.81(17) . . ?
N3 C17 C1 121.5(2) . . ?
N3 C17 H17 119.3 . . ?
C1 C17 H17 119.3 . . ?

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 C11 C12 C13 177.05(18) . . . . ?
O4 N3 C4 N1 3.3(3) . . . . ?
O4 N3 C4 C3 179.9(2) . . . . ?
O4 N3 C17 C1 179.6(2) . . . . ?
F1 C14 C15 C10 179.1(2) . . . . ?
F1 C14 C15 C16 1.8(4) . . . . ?
N1 C5 C6 C7 -58.9(2) . . . . ?
N1 C5 C10 C11 -174.0(2) . . . . ?
N1 C5 C10 C15 1.4(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C17 N3 0.6(4) . . . . ?
C2 C3 C4 N1 176.8(2) . . . . ?
C2 C3 C4 N3 0.4(4) . . . . ?
C4 N1 C5 C6 -48.5(3) . . . . ?
C4 N1 C5 C10 -174.54(18) . . . . ?
C4 N1 C16 O1 -6.4(3) . . . . ?
C4 N1 C16 C15 175.03(18) . . . . ?
C4 N3 C17 C1 -0.6(4) . . . . ?
C5 N1 C4 N3 -56.9(3) . . . . ?
C5 N1 C4 C3 126.6(2) . . . . ?
C5 N1 C16 O1 -178.2(2) . . . . ?
C5 N1 C16 C15 3.2(2) . . . . ?
C5 C6 C7 O3 -11.2(4) . . . . ?
C5 C6 C7 O2 167.8(2) . . . . ?
C5 C10 C11 Br1 -0.9(3) . . . . ?
C5 C10 C11 C12 177.1(2) . . . . ?
C5 C10 C15 C14 -177.50(19) . . . . ?
C5 C10 C15 C16 0.3(2) . . . . ?
C6 C5 C10 C11 63.8(3) . . . . ?
C6 C5 C10 C15 -120.8(2) . . . . ?
C7 O2 C8 C9 159.8(4) . . . . ?
C8 O2 C7 O3 0.4(5) . . . . ?
C8 O2 C7 C6 -178.6(3) . . . . ?
C10 C5 C6 C7 57.4(3) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C10 C15 C16 O1 179.4(2) . . . . ?
C10 C15 C16 N1 -2.1(2) . . . . ?
C11 C10 C15 C14 -1.5(3) . . . . ?
C11 C10 C15 C16 176.29(19) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 F1 -178.0(2) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C13 C14 C15 C16 -177.5(2) . . . . ?
C14 C15 C16 O1 -3.1(4) . . . . ?
C14 C15 C16 N1 175.5(2) . . . . ?
C15 C10 C11 Br1 -175.91(16) . . . . ?
C15 C10 C11 C12 2.1(3) . . . . ?
C16 N1 C4 N3 132.0(2) . . . . ?
C16 N1 C4 C3 -44.5(3) . . . . ?
C16 N1 C5 C6 123.12(19) . . . . ?
C16 N1 C5 C10 -2.9(2) . . . . ?
C17 N3 C4 N1 -176.5(2) . . . . ?
C17 N3 C4 C3 0.1(3) . . . . ?
C17 C1 C2 C3 -0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
