# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_b4-b_298k
_database_code_depnum_ccdc_archive 'CCDC 2191897'
loop_
_audit_author_name
_audit_author_address
'hassan allouchi'
;University of Tours
France
;

_audit_update_record             
;
2022-07-21 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Br N3 O2'
_chemical_formula_weight         384.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.1311(9)
_cell_length_b                   4.8926(3)
_cell_length_c                   20.9345(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.669(6)
_cell_angle_gamma                90
_cell_volume                     1618.07(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2486
_cell_measurement_theta_min      2.9990
_cell_measurement_theta_max      23.5530

_exptl_crystal_description       'needle, axis [0 1 0]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6100
_exptl_crystal_size_mid          0.0450
_exptl_crystal_size_min          0.0200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 0 0.0200 0.9963 -0.0002 0.0003 -0.0037 0.0446 0.0018
-1 0 0 0.0200 -0.9963 0.0002 -0.0003 0.0037 -0.0446 -0.0018
0 1 0 0.3300 0.0012 0.9964 0.0010 -0.0084 0.0052 -0.1441
0 -1 0 0.2800 -0.0012 -0.9964 -0.0010 0.0084 -0.0052 0.1441
0 0 1 0.0150 0.0004 0.0000 0.9959 -0.0341 0.0041 0.0021
0 0 -1 0.0050 -0.0004 -0.0000 -0.9959 0.0341 -0.0041 -0.0021
_exptl_absorpt_coefficient_mu    2.556
_shelx_estimated_absorpt_T_min   0.305
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_T_min  0.4077
_exptl_absorpt_correction_T_max  0.9506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11840
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_orient_matrix_UB_11      -0.0036592000
_diffrn_orient_matrix_UB_12      -0.0084246000
_diffrn_orient_matrix_UB_13      -0.0342774000
_diffrn_orient_matrix_UB_21      0.0447174000
_diffrn_orient_matrix_UB_22      0.0051455000
_diffrn_orient_matrix_UB_23      0.0041325000
_diffrn_orient_matrix_UB_31      0.0017835000
_diffrn_orient_matrix_UB_32      -0.1446473000
_diffrn_orient_matrix_UB_33      0.0021339000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00  -42.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0112  117.0000  -82.0041 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   72.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0112   57.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00   18.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0112  -99.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega -106.00    9.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0112  -57.0000 -180.0000 115

#__ type_ start__ end____ width___ exp.time_
  5 omega  -60.00  -35.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7924  -38.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7924 -178.0000   90.0000 71

;

_reflns_number_total             3299
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3299
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0603(2) 0.9604(7) 0.29544(18) 0.0454(9) Uani 1 1 d . . . . .
H4 H 0.0835 0.8962 0.2611 0.055 Uiso 1 1 calc R U . . .
C1 C -0.0941(2) 1.4301(7) 0.40482(18) 0.0408(8) Uani 1 1 d . . . . .
C6 C 0.0563(2) 0.9345(6) 0.40786(18) 0.0419(8) Uani 1 1 d . . . . .
H6 H 0.0733 0.8635 0.4497 0.050 Uiso 1 1 calc R U . . .
C2 C -0.0899(2) 1.4411(6) 0.33920(17) 0.0380(8) Uani 1 1 d . . . . .
C7 C -0.1385(2) 1.6247(7) 0.28991(19) 0.0422(9) Uani 1 1 d . . . . .
C5 C 0.0897(2) 0.8420(6) 0.35714(17) 0.0377(8) Uani 1 1 d . . . . .
C8 C -0.1684(2) 1.7519(9) 0.17909(18) 0.0549(10) Uani 1 1 d . . . . .
H8A H -0.1526 1.9419 0.1872 0.066 Uiso 1 1 calc R U . . .
H8B H -0.2289 1.7348 0.1765 0.066 Uiso 1 1 calc R U . . .
C9 C -0.1455(3) 1.6567(8) 0.1171(2) 0.0710(13) Uani 1 1 d . . . . .
H9A H -0.0856 1.6756 0.1203 0.107 Uiso 1 1 calc R U . . .
H9B H -0.1750 1.7651 0.0814 0.107 Uiso 1 1 calc R U . . .
H9C H -0.1613 1.4683 0.1098 0.107 Uiso 1 1 calc R U . . .
C10 C 0.1536(2) 0.6321(7) 0.36547(18) 0.0436(9) Uani 1 1 d . . . . .
N3 N 0.00286(18) 1.1540(5) 0.28219(14) 0.0437(7) Uani 1 1 d . . . . .
O1 O -0.18615(17) 1.7974(5) 0.30153(13) 0.0638(8) Uani 1 1 d . . . . .
C3 C -0.0300(2) 1.2428(7) 0.33269(17) 0.0374(8) Uani 1 1 d . . . . .
O2 O -0.12265(15) 1.5808(5) 0.23068(13) 0.0502(6) Uani 1 1 d . . . . .
N2 N -0.00284(16) 1.1344(5) 0.39469(14) 0.0372(7) Uani 1 1 d . . . . .
N1 N -0.04279(18) 1.2494(6) 0.44011(14) 0.0444(7) Uani 1 1 d . . . . .
Br1 Br -0.16122(2) 1.63368(8) 0.45012(2) 0.05976(18) Uani 1 1 d . . . . .
C11 C 0.2074(2) 0.4637(7) 0.37034(17) 0.0437(9) Uani 1 1 d . . . . .
C12 C 0.2737(2) 0.2604(7) 0.37707(18) 0.0402(8) Uani 1 1 d . . . . .
C13 C 0.3005(2) 0.1625(7) 0.32204(18) 0.0471(9) Uani 1 1 d . . . . .
H13 H 0.2751 0.2260 0.2809 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3649(2) -0.0287(7) 0.32847(18) 0.0455(9) Uani 1 1 d . . . . .
H14 H 0.3822 -0.0913 0.2913 0.055 Uiso 1 1 calc R U . . .
C15 C 0.4043(2) -0.1290(6) 0.38867(19) 0.0426(9) Uani 1 1 d . . . . .
C16 C 0.3771(2) -0.0299(8) 0.44325(19) 0.0520(10) Uani 1 1 d . . . . .
H16 H 0.4024 -0.0941 0.4844 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3135(2) 0.1616(7) 0.43742(19) 0.0531(10) Uani 1 1 d . . . . .
H17 H 0.2970 0.2259 0.4748 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4730(2) -0.3414(7) 0.3953(2) 0.0577(11) Uani 1 1 d . . . . .
H18A H 0.4483 -0.5204 0.3940 0.087 Uiso 1 1 calc R U . . .
H18B H 0.5120 -0.3167 0.4360 0.087 Uiso 1 1 calc R U . . .
H18C H 0.5024 -0.3227 0.3600 0.087 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
C4 N3 1.315(4) . ?
C4 C5 1.407(5) . ?
C4 H4 0.9300 . ?
C1 N1 1.328(4) . ?
C1 C2 1.390(5) . ?
C1 Br1 1.866(3) . ?
C6 N2 1.355(4) . ?
C6 C5 1.362(4) . ?
C6 H6 0.9300 . ?
C2 C3 1.395(4) . ?
C2 C7 1.469(5) . ?
C7 O1 1.200(4) . ?
C7 O2 1.333(4) . ?
C5 C10 1.440(5) . ?
C8 O2 1.446(4) . ?
C8 C9 1.494(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.186(4) . ?
N3 C3 1.347(4) . ?
C3 N2 1.388(4) . ?
N2 N1 1.373(3) . ?
C11 C12 1.447(5) . ?
C12 C17 1.384(5) . ?
C12 C13 1.395(5) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(5) . ?
C15 C18 1.505(4) . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 H17 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
N3 C4 C5 125.6(3) . . ?
N3 C4 H4 117.2 . . ?
C5 C4 H4 117.2 . . ?
N1 C1 C2 115.2(3) . . ?
N1 C1 Br1 115.7(3) . . ?
C2 C1 Br1 129.1(3) . . ?
N2 C6 C5 117.0(3) . . ?
N2 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C1 C2 C3 104.0(3) . . ?
C1 C2 C7 126.3(3) . . ?
C3 C2 C7 129.7(3) . . ?
O1 C7 O2 123.6(3) . . ?
O1 C7 C2 124.1(4) . . ?
O2 C7 C2 112.3(3) . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 C10 121.9(3) . . ?
C4 C5 C10 120.3(3) . . ?
O2 C8 C9 106.8(3) . . ?
O2 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O2 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 177.4(4) . . ?
C4 N3 C3 116.1(3) . . ?
N3 C3 N2 120.7(3) . . ?
N3 C3 C2 133.7(3) . . ?
N2 C3 C2 105.5(3) . . ?
C7 O2 C8 115.9(3) . . ?
C6 N2 N1 124.4(3) . . ?
C6 N2 C3 122.8(3) . . ?
N1 N2 C3 112.8(3) . . ?
C1 N1 N2 102.4(3) . . ?
C10 C11 C12 179.2(4) . . ?
C17 C12 C13 118.0(3) . . ?
C17 C12 C11 121.8(3) . . ?
C13 C12 C11 120.2(3) . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 117.6(3) . . ?
C14 C15 C18 121.5(3) . . ?
C16 C15 C18 120.9(4) . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.071




_publcif_funding_html            
;
;
