# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_C18H13BrN2O-1
_database_code_depnum_ccdc_archive 'CCDC 2296508'
loop_
_audit_author_name
_audit_author_address
'HIroshi Aoyama'
;Osaka University
Japan
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-12-17 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H13 Br N2 O'
_chemical_formula_moiety         'C18 H13 Br N2 O'
_chemical_formula_weight         353.22
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.0262(11)
_cell_length_b                   9.2338(14)
_cell_length_c                   24.100(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1563.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4428
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712.00
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_T_max  0.453

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10418
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.020
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3443
_reflns_number_gt                3099
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.961

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0539
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3443
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.20762(5) -0.07175(4) 0.60195(2) 0.01913(10) Uani 1 1 d . . . . .
O1 O 0.7320(4) -0.2184(2) 0.65752(8) 0.0228(6) Uani 1 1 d . . . . .
N1 N 1.0885(4) 0.1317(3) 0.68184(10) 0.0158(6) Uani 1 1 d . . . . .
N2 N 0.8492(3) 0.0455(3) 0.62824(10) 0.0139(6) Uani 1 1 d . . . . .
C1 C 1.0398(4) 0.0457(4) 0.64145(12) 0.0142(7) Uani 1 1 d . . . . .
C2 C 0.9154(5) 0.1946(4) 0.69782(12) 0.0151(7) Uani 1 1 d . . . . .
C3 C 0.8791(6) 0.2962(4) 0.73991(13) 0.0211(8) Uani 1 1 d . . . . .
H3 H 0.976751 0.332925 0.761854 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6929(5) 0.3394(4) 0.74739(12) 0.0198(8) Uani 1 1 d . . . . .
H4 H 0.664643 0.405377 0.775346 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5455(5) 0.2865(4) 0.71407(13) 0.0199(8) Uani 1 1 d . . . . .
H5 H 0.422197 0.319719 0.719994 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5783(5) 0.1861(4) 0.67247(13) 0.0178(8) Uani 1 1 d . . . . .
H6 H 0.480601 0.149527 0.650513 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7668(5) 0.1434(3) 0.66566(12) 0.0136(7) Uani 1 1 d . . . . .
C8 C 0.7529(4) -0.0430(3) 0.58858(11) 0.0132(7) Uani 1 1 d . . . . .
C9 C 0.7255(5) 0.0099(4) 0.53385(12) 0.0143(7) Uani 1 1 d . . . . .
C10 C 0.7994(5) 0.1440(4) 0.51525(13) 0.0224(8) Uani 1 1 d . . . . .
H10 H 0.863266 0.204410 0.539868 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7768(6) 0.1849(4) 0.46080(13) 0.0313(9) Uani 1 1 d . . . . .
H11 H 0.827852 0.272408 0.448803 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6777(5) 0.0969(4) 0.42290(14) 0.0325(10) Uani 1 1 d . . . . .
H12 H 0.664531 0.126178 0.386180 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6013(5) -0.0309(4) 0.43986(13) 0.0260(9) Uani 1 1 d . . . . .
H13 H 0.533832 -0.087513 0.414737 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6234(4) -0.0792(4) 0.49577(12) 0.0167(7) Uani 1 1 d . . . . .
C15 C 0.5538(4) -0.2139(4) 0.51404(13) 0.0195(8) Uani 1 1 d . . . . .
H15 H 0.483202 -0.270633 0.489677 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5869(5) -0.2638(4) 0.56667(13) 0.0192(8) Uani 1 1 d . . . . .
H16 H 0.542250 -0.354394 0.577416 0.023 Uiso 1 1 calc R U . . .
C17 C 0.6890(4) -0.1771(3) 0.60442(13) 0.0150(7) Uani 1 1 d . . . . .
C18 C 0.6822(6) -0.3629(4) 0.67442(13) 0.0297(9) Uani 1 1 d . . . . .
H18A H 0.720005 -0.377645 0.712285 0.036 Uiso 1 1 calc R U . . .
H18B H 0.547110 -0.375920 0.671174 0.036 Uiso 1 1 calc R U . . .
H18C H 0.746297 -0.431635 0.651090 0.036 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       DTREK
_computing_cell_refinement       DTREK
_computing_data_reduction        DTREK
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.864(3) . ?
O1 C17 1.369(3) . ?
O1 C18 1.439(4) . ?
N1 C1 1.302(4) . ?
N1 C2 1.402(4) . ?
N2 C1 1.376(4) . ?
N2 C7 1.402(4) . ?
N2 C8 1.428(3) . ?
C2 C7 1.383(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9300 . ?
C8 C17 1.371(4) . ?
C8 C9 1.420(4) . ?
C9 C10 1.416(5) . ?
C9 C14 1.426(4) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.407(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.428(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(5) . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.409(4) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C17 O1 C18 118.0(3) . . ?
C1 N1 C2 103.3(3) . . ?
C1 N2 C7 104.6(3) . . ?
C1 N2 C8 128.1(3) . . ?
C7 N2 C8 127.1(2) . . ?
N1 C1 N2 115.5(3) . . ?
N1 C1 Br1 124.8(2) . . ?
N2 C1 Br1 119.8(2) . . ?
C7 C2 N1 111.1(3) . . ?
C7 C2 C3 119.7(3) . . ?
N1 C2 C3 129.2(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 115.7(3) . . ?
C5 C6 H6 122.2 . . ?
C7 C6 H6 122.2 . . ?
C2 C7 C6 123.8(3) . . ?
C2 C7 N2 105.6(3) . . ?
C6 C7 N2 130.6(3) . . ?
C17 C8 C9 121.7(3) . . ?
C17 C8 N2 119.0(3) . . ?
C9 C8 N2 119.3(3) . . ?
C10 C9 C8 123.1(3) . . ?
C10 C9 C14 119.0(3) . . ?
C8 C9 C14 117.9(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C9 118.9(3) . . ?
C15 C14 C13 122.3(3) . . ?
C9 C14 C13 118.8(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O1 C17 C8 116.1(3) . . ?
O1 C17 C16 123.9(3) . . ?
C8 C17 C16 120.0(3) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C2 N1 C1 N2 0.5(4) . . . . ?
C2 N1 C1 Br1 -179.7(2) . . . . ?
C7 N2 C1 N1 -0.6(4) . . . . ?
C8 N2 C1 N1 -175.9(3) . . . . ?
C7 N2 C1 Br1 179.6(2) . . . . ?
C8 N2 C1 Br1 4.3(4) . . . . ?
C1 N1 C2 C7 -0.2(4) . . . . ?
C1 N1 C2 C3 179.6(3) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
N1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
N1 C2 C7 C6 179.5(3) . . . . ?
C3 C2 C7 C6 -0.4(5) . . . . ?
N1 C2 C7 N2 -0.1(4) . . . . ?
C3 C2 C7 N2 -180.0(3) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C5 C6 C7 N2 180.0(3) . . . . ?
C1 N2 C7 C2 0.4(3) . . . . ?
C8 N2 C7 C2 175.7(3) . . . . ?
C1 N2 C7 C6 -179.2(3) . . . . ?
C8 N2 C7 C6 -3.8(5) . . . . ?
C1 N2 C8 C17 86.4(4) . . . . ?
C7 N2 C8 C17 -87.9(4) . . . . ?
C1 N2 C8 C9 -93.7(4) . . . . ?
C7 N2 C8 C9 92.0(4) . . . . ?
C17 C8 C9 C10 -176.2(3) . . . . ?
N2 C8 C9 C10 3.9(5) . . . . ?
C17 C8 C9 C14 1.9(5) . . . . ?
N2 C8 C9 C14 -178.0(3) . . . . ?
C8 C9 C10 C11 176.3(3) . . . . ?
C14 C9 C10 C11 -1.8(5) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C10 C9 C14 C15 178.6(3) . . . . ?
C8 C9 C14 C15 0.4(4) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
C8 C9 C14 C13 -177.3(3) . . . . ?
C12 C13 C14 C15 -177.0(3) . . . . ?
C12 C13 C14 C9 0.7(5) . . . . ?
C9 C14 C15 C16 -2.3(5) . . . . ?
C13 C14 C15 C16 175.4(3) . . . . ?
C14 C15 C16 C17 1.8(5) . . . . ?
C18 O1 C17 C8 -174.7(3) . . . . ?
C18 O1 C17 C16 4.7(5) . . . . ?
C9 C8 C17 O1 177.0(3) . . . . ?
N2 C8 C17 O1 -3.1(4) . . . . ?
C9 C8 C17 C16 -2.5(5) . . . . ?
N2 C8 C17 C16 177.4(3) . . . . ?
C15 C16 C17 O1 -178.8(3) . . . . ?
C15 C16 C17 C8 0.6(5) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
