# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_KK007_2
_database_code_depnum_ccdc_archive 'CCDC 2330354'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;University of Rennes
France
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13 octobre 2023                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H5 Br2 N'
_chemical_formula_sum            'C8 H5 Br2 N'
_chemical_formula_weight         274.95
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
_space_group_IT_number           62
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.7185(18)
_cell_length_b                   7.2021(9)
_cell_length_c                   8.8003(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     869.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4083
_cell_measurement_theta_min      2.7498
_cell_measurement_theta_max      27.4537
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0149689
_diffrn_orient_matrix_UB_21      0.0423291
_diffrn_orient_matrix_UB_31      0.1313886
_diffrn_orient_matrix_UB_12      0.0783379
_diffrn_orient_matrix_UB_22      0.0805342
_diffrn_orient_matrix_UB_32      -0.0170205
_diffrn_orient_matrix_UB_13      -0.0522151
_diffrn_orient_matrix_UB_23      0.0463761
_diffrn_orient_matrix_UB_33      -0.0208897


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             520
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.312
_exptl_absorpt_correction_T_max  0.435

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2022.10-0       #
# Number of scans            :        5                                        #
# Total length of scans  [*] :   291.00 (deg.)                                 #
# Total exposition time  [*] :      1 h 37 min.                                #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     2.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    2.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7  144.0  -44.5 150.0 #
#  4 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7  216.0  -44.5 150.0 #
#  5 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0183
_diffrn_reflns_av_r_equivalents  0.0304
_diffrn_reflns_number            7270
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.750
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             1074
_reflns_number_gt                883
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2023)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

# start Validation Reply Form
_vrf_PLATxxx_job                 
;
PROBLEM: 
RESPONSE:
blablabla
;
# end Validation Reply Form

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²+1.6587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         1074
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.073

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 0.20624(2) 0.53161(4) 0.49716(3) 0.03419(11) Uani 1 1 d . . . . .
C1 C 0.2813(3) 0.750000 0.4390(4) 0.0270(8) Uani 1 2 d S T P . .
H1 H 0.288738 0.749999 0.325936 0.032 Uiso 1 2 calc R U P . .
C2 C 0.3811(2) 0.750000 0.5090(4) 0.0220(6) Uani 1 2 d S T P . .
C3 C 0.3941(3) 0.750000 0.6659(4) 0.0272(8) Uani 1 2 d S T P . .
H3 H 0.338674 0.750000 0.730562 0.033 Uiso 1 2 calc R U P . .
C4 C 0.4862(3) 0.750000 0.7295(4) 0.0284(8) Uani 1 2 d S T P . .
H4 H 0.493816 0.750000 0.836794 0.034 Uiso 1 2 calc R U P . .
C5 C 0.5675(3) 0.750000 0.6359(4) 0.0268(8) Uani 1 2 d S T P . .
H5 H 0.630802 0.750000 0.679584 0.032 Uiso 1 2 calc R U P . .
C6 C 0.5572(3) 0.750000 0.4797(4) 0.0247(7) Uani 1 2 d S T P . .
H6 H 0.613112 0.750000 0.416034 0.030 Uiso 1 2 calc R U P . .
C7 C 0.4639(3) 0.750000 0.4161(4) 0.0202(7) Uani 1 2 d S T P . .
C8 C 0.4538(2) 0.750000 0.2527(4) 0.0234(7) Uani 1 2 d S T P . .
N9 N 0.4454(2) 0.750000 0.1235(3) 0.0310(7) Uani 1 2 d S T P . .



#------------------------------------------------------------------------------#
#                              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 1.948(2) . ?
C1 C2 1.501(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.393(5) . ?
C2 C7 1.401(5) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.445(5) . ?
C8 N9 1.143(4) . ?

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 C1 Br1 111.96(15) . 7_575 ?
C2 C1 Br1 111.96(15) . . ?
Br1 C1 Br1 107.66(16) 7_575 . ?
C2 C1 H1 108.4 . . ?
Br1 C1 H1 108.4 7_575 . ?
Br1 C1 H1 108.4 . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 121.7(3) . . ?
C7 C2 C1 120.0(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 C8 119.1(3) . . ?
C2 C7 C8 120.2(3) . . ?
N9 C8 C7 179.7(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
Br1 C1 C2 C3 60.50(15) 7_575 . . . ?
Br1 C1 C2 C3 -60.50(15) . . . . ?
Br1 C1 C2 C7 -119.50(15) 7_575 . . . ?
Br1 C1 C2 C7 119.50(15) . . . . ?
C7 C2 C3 C4 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C5 C6 C7 C2 0.000(0) . . . . ?
C5 C6 C7 C8 180.000(1) . . . . ?
C3 C2 C7 C6 0.000(0) . . . . ?
C1 C2 C7 C6 180.000(0) . . . . ?
C3 C2 C7 C8 180.000(0) . . . . ?
C1 C2 C7 C8 0.000(0) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


