# 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_cyg399
_database_code_depnum_ccdc_archive 'CCDC 2287548'
loop_
_audit_author_name
_audit_author_address
'Guanjie Wang'
;Nanyang Technological University
China
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2024-03-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 Br N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         478.33
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   11.7769(4)
_cell_length_b                   11.7769(4)
_cell_length_c                   31.359(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4349.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8371
_cell_measurement_theta_min      2.4458
_cell_measurement_theta_max      28.1789
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952

_exptl_absorpt_coefficient_mu    1.922
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.61

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker X8APEX'
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'APEX II CCD'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            45451
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_unetI/netI     0.1067
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       45

_refine_special_details          
;
;

_reflns_number_total             6940
_reflns_number_gt                4337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0867
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_number_reflns         6940
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.578
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(7)

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'
O O 0.0106 0.0060 '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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.42152(4) 0.16071(3) 0.49990(2) 0.03569(13) Uani d . . . 1 . .
O O2 0.4256(2) 0.3446(2) 0.73294(8) 0.0223(6) Uani d . . . 1 . .
O O3 0.5860(2) 0.3360(2) 0.69418(8) 0.0256(6) Uani d . . . 1 . .
O O4 0.3190(2) 0.6205(2) 0.60439(8) 0.0240(7) Uani d . . . 1 . .
O O5 0.6644(2) 0.6827(2) 0.66099(8) 0.0254(6) Uani d . . . 1 . .
N N1 0.5031(2) 0.6337(2) 0.62610(9) 0.0147(7) Uani d . . . 1 . .
C C20 0.5553(3) 0.8350(3) 0.63441(10) 0.0140(7) Uani d . . . 1 . .
C C5 0.5166(3) 0.5143(3) 0.64094(10) 0.0148(7) Uani d . . . 1 . .
H H5 0.599376 0.504351 0.647045 0.018000 Uiso calc U . R 1 . .
C C12 0.4119(3) 0.6605(3) 0.59771(11) 0.0168(8) Uani d . . . 1 . .
C C25 0.4505(3) 0.8817(3) 0.64481(11) 0.0159(8) Uani d . . . 1 . .
H H25 0.390356 0.834008 0.654106 0.019000 Uiso calc U . R 1 . .
C C13 0.4381(3) 0.7276(3) 0.55895(11) 0.0152(8) Uani d . . . 1 . .
C C3 0.4558(3) 0.4886(3) 0.68210(11) 0.0169(8) Uani d . . . 1 . .
C C9 0.4472(3) 0.2731(3) 0.54214(12) 0.0203(8) Uani d . . . 1 . .
C C7 0.3899(3) 0.3667(3) 0.60573(11) 0.0180(8) Uani d . . . 1 . .
H H7 0.335430 0.377731 0.627683 0.022000 Uiso calc U . R 1 . .
C C19 0.5805(3) 0.7129(3) 0.64116(11) 0.0165(8) Uani d . . . 1 . .
C C21 0.6425(3) 0.9057(3) 0.62083(10) 0.0191(8) Uani d . . . 1 . .
H H21 0.714921 0.874703 0.614314 0.023000 Uiso calc U . R 1 . .
C C6 0.4884(3) 0.4303(3) 0.60572(11) 0.0159(8) Uani d . . . 1 . .
C C18 0.5455(3) 0.7307(3) 0.54089(11) 0.0181(8) Uani d . . . 1 . .
H H18 0.606579 0.692056 0.554311 0.022000 Uiso calc U . R 1 . .
C C16 0.4752(3) 0.8472(3) 0.48434(11) 0.0241(9) Uani d . . . 1 . .
H H16 0.488246 0.889378 0.458999 0.029000 Uiso calc U . R 1 . .
C C10 0.5453(3) 0.3362(3) 0.54068(12) 0.0258(9) Uani d . . . 1 . .
H H10 0.597945 0.326232 0.518039 0.031000 Uiso calc U . R 1 . .
C C24 0.4337(3) 0.9980(3) 0.64163(11) 0.0231(9) Uani d . . . 1 . .
H H24 0.362456 1.030116 0.649096 0.028000 Uiso calc U . R 1 . .
C C14 0.3492(3) 0.7844(3) 0.53932(11) 0.0192(8) Uani d . . . 1 . .
H H14 0.275567 0.782543 0.551679 0.023000 Uiso calc U . R 1 . .
C C17 0.5640(3) 0.7898(3) 0.50347(12) 0.0211(8) Uani d . . . 1 . .
H H17 0.637406 0.790954 0.490935 0.025000 Uiso calc U . R 1 . .
C C23 0.5208(4) 1.0671(3) 0.62758(12) 0.0246(9) Uani d . . . 1 . .
H H23 0.509384 1.146738 0.625358 0.030000 Uiso calc U . R 1 . .
C C8 0.3696(3) 0.2872(3) 0.57424(13) 0.0233(9) Uani d . . . 1 . .
H H8 0.302342 0.242690 0.574849 0.028000 Uiso calc U . R 1 . .
C C2 0.4975(3) 0.3828(3) 0.70319(12) 0.0185(8) Uani d . . . 1 . .
C C11 0.5663(3) 0.4144(3) 0.57273(11) 0.0239(8) Uani d . . . 1 . .
H H11 0.634395 0.457688 0.572227 0.029000 Uiso calc U . R 1 . .
C C15 0.3671(3) 0.8436(3) 0.50187(13) 0.0247(8) Uani d . . . 1 . .
H H15 0.305875 0.881524 0.488235 0.030000 Uiso calc U . R 1 . .
C C22 0.6243(3) 1.0207(3) 0.61679(12) 0.0248(10) Uani d . . . 1 . .
H H22 0.683406 1.068241 0.606500 0.030000 Uiso calc U . R 1 . .
C C4 0.3756(3) 0.5510(3) 0.69934(13) 0.0283(10) Uani d . . . 1 . .
H H4A 0.342878 0.529188 0.725786 0.034000 Uiso calc U . R 1 . .
H H4B 0.350399 0.617983 0.685373 0.034000 Uiso calc U . R 1 . .
C C1 0.4583(3) 0.2412(3) 0.75443(13) 0.0283(10) Uani d . . . 1 . .
H H1A 0.469337 0.180756 0.733354 0.043000 Uiso calc U . R 1 . .
H H1B 0.398482 0.218920 0.774473 0.043000 Uiso calc U . R 1 . .
H H1C 0.529296 0.253759 0.770037 0.043000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.897(4) ?
O2 C2 . 1.338(4) ?
O2 C1 . 1.444(4) ?
O3 C2 . 1.211(4) ?
O4 C12 . 1.210(4) ?
O5 C19 . 1.221(4) ?
N1 C19 . 1.387(4) ?
N1 C12 . 1.431(4) ?
N1 C5 . 1.489(4) ?
C20 C21 . 1.390(5) ?
C20 C25 . 1.390(5) ?
C20 C19 . 1.483(5) ?
C5 C3 . 1.507(5) ?
C5 C6 . 1.520(5) ?
C12 C13 . 1.482(5) ?
C25 C24 . 1.388(5) ?
C13 C18 . 1.386(5) ?
C13 C14 . 1.386(5) ?
C3 C4 . 1.313(5) ?
C3 C2 . 1.493(5) ?
C9 C8 . 1.369(5) ?
C9 C10 . 1.374(5) ?
C7 C6 . 1.381(5) ?
C7 C8 . 1.382(5) ?
C21 C22 . 1.376(5) ?
C6 C11 . 1.395(5) ?
C18 C17 . 1.382(5) ?
C16 C17 . 1.382(5) ?
C16 C15 . 1.387(5) ?
C10 C11 . 1.386(5) ?
C24 C23 . 1.381(5) ?
C14 C15 . 1.382(5) ?
C23 C22 . 1.378(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O2 C1 . . 116.1(3) ?
C19 N1 C12 . . 123.8(3) ?
C19 N1 C5 . . 117.2(3) ?
C12 N1 C5 . . 118.9(3) ?
C21 C20 C25 . . 119.4(3) ?
C21 C20 C19 . . 118.5(3) ?
C25 C20 C19 . . 121.9(3) ?
N1 C5 C3 . . 114.0(3) ?
N1 C5 C6 . . 111.3(3) ?
C3 C5 C6 . . 112.8(3) ?
O4 C12 N1 . . 119.0(3) ?
O4 C12 C13 . . 122.6(3) ?
N1 C12 C13 . . 118.2(3) ?
C24 C25 C20 . . 120.0(3) ?
C18 C13 C14 . . 119.7(3) ?
C18 C13 C12 . . 122.6(3) ?
C14 C13 C12 . . 117.6(3) ?
C4 C3 C2 . . 121.4(3) ?
C4 C3 C5 . . 125.6(3) ?
C2 C3 C5 . . 113.0(3) ?
C8 C9 C10 . . 121.3(3) ?
C8 C9 Br1 . . 119.4(3) ?
C10 C9 Br1 . . 119.2(3) ?
C6 C7 C8 . . 120.9(3) ?
O5 C19 N1 . . 120.6(3) ?
O5 C19 C20 . . 121.1(3) ?
N1 C19 C20 . . 118.1(3) ?
C22 C21 C20 . . 120.2(4) ?
C7 C6 C11 . . 118.7(3) ?
C7 C6 C5 . . 122.5(3) ?
C11 C6 C5 . . 118.8(3) ?
C17 C18 C13 . . 120.3(3) ?
C17 C16 C15 . . 120.5(4) ?
C9 C10 C11 . . 119.0(3) ?
C23 C24 C25 . . 119.9(4) ?
C15 C14 C13 . . 120.3(4) ?
C18 C17 C16 . . 119.7(4) ?
C22 C23 C24 . . 120.1(4) ?
C9 C8 C7 . . 119.5(3) ?
O3 C2 O2 . . 123.6(3) ?
O3 C2 C3 . . 124.0(3) ?
O2 C2 C3 . . 112.4(3) ?
C10 C11 C6 . . 120.6(4) ?
C14 C15 C16 . . 119.5(3) ?
C21 C22 C23 . . 120.4(4) ?

