#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/90/4509063.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509063
loop_
_publ_author_name
'Ojala, William H.'
'Lystad, Kendra M.'
'Deal, Tera L.'
'Engebretson, Jessica E.'
'Spude, Jill M.'
'Balidemaj, Barjeta'
'Ojala, Charles R.'
_publ_section_title
;
 Bridge Orientation as a Selector of Intermolecular Interactions in a
 Series of Crystalline Isomeric Benzylideneanilines
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              964
_journal_paper_doi               10.1021/cg8007443
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.14
_chemical_melting_point          370.0(10)
_chemical_name_systematic
; 
 N-(4-bromobenzylidene)-2-cyanoaniline 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-01-23 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.104(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7628(13)
_cell_length_b                   7.4094(7)
_cell_length_c                   23.245(2)
_cell_measurement_reflns_used    3360
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.311
_cell_measurement_theta_min      2.296
_cell_volume                     2370.4(4)
_computing_cell_refinement       'SAINTPLUS, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINTPLUS, Bruker'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26816
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    3.444
_exptl_absorpt_correction_T_max  0.708
_exptl_absorpt_correction_T_min  0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ\^2\^(Fo\^2\^)+(0.0329P)\^2\^+1.0883P], P=(Fo\^2\^+2Fc\^2\^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                4499
_reflns_number_total             5406
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg8007443sup1.cif
_cod_data_source_block           3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '369-371' was changed to '370.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4509063
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.236590(14) 0.42339(3) 0.222653(10) 0.03978(7) Uani 1 1 d .
Br2 Br -0.268039(14) 0.83798(3) 0.591259(10) 0.04225(8) Uani 1 1 d .
C1 C 0.82103(13) 0.4350(2) 0.30515(8) 0.0248(4) Uani 1 1 d .
C2 C 0.85941(13) 0.5315(2) 0.35196(8) 0.0248(4) Uani 1 1 d .
C3 C 0.95973(14) 0.5455(3) 0.35970(8) 0.0286(4) Uani 1 1 d .
H3 H 0.9852 0.6134 0.3909 0.034 Uiso 1 1 calc R
C4 C 1.02222(14) 0.4600(3) 0.32172(9) 0.0307(4) Uani 1 1 d .
H4 H 1.0905 0.4685 0.3270 0.037 Uiso 1 1 calc R
C5 C 0.98430(14) 0.3618(3) 0.27591(9) 0.0308(4) Uani 1 1 d .
H5 H 1.0271 0.3023 0.2501 0.037 Uiso 1 1 calc R
C6 C 0.88461(13) 0.3497(3) 0.26738(8) 0.0277(4) Uani 1 1 d .
H6 H 0.8597 0.2831 0.2357 0.033 Uiso 1 1 calc R
C7 C 0.57285(13) 0.4265(2) 0.24529(8) 0.0247(4) Uani 1 1 d .
C8 C 0.51171(14) 0.4263(3) 0.29306(8) 0.0307(4) Uani 1 1 d .
H8 H 0.5389 0.4277 0.3307 0.037 Uiso 1 1 calc R
C9 C 0.41231(14) 0.4242(3) 0.28620(9) 0.0335(4) Uani 1 1 d .
H9 H 0.3708 0.4248 0.3188 0.040 Uiso 1 1 calc R
C10 C 0.37364(13) 0.4211(2) 0.23117(9) 0.0270(4) Uani 1 1 d .
C11 C 0.43161(14) 0.4196(3) 0.18305(8) 0.0319(4) Uani 1 1 d .
H11 H 0.4039 0.4162 0.1456 0.038 Uiso 1 1 calc R
C12 C 0.53152(14) 0.4232(3) 0.19050(8) 0.0334(4) Uani 1 1 d .
H12 H 0.5726 0.4235 0.1577 0.040 Uiso 1 1 calc R
C13 C 0.67867(13) 0.4326(3) 0.25188(8) 0.0279(4) Uani 1 1 d .
H13 H 0.7182 0.4417 0.2186 0.033 Uiso 1 1 calc R
C14 C 0.79367(14) 0.6207(3) 0.39075(8) 0.0285(4) Uani 1 1 d .
C15 C 0.31357(13) 0.7378(3) 0.51198(8) 0.0263(4) Uani 1 1 d .
C16 C 0.35330(13) 0.7063(3) 0.45748(8) 0.0281(4) Uani 1 1 d .
C17 C 0.45359(14) 0.7056(3) 0.44936(9) 0.0333(4) Uani 1 1 d .
H17 H 0.4797 0.6847 0.4121 0.040 Uiso 1 1 calc R
C18 C 0.51513(14) 0.7353(3) 0.49541(9) 0.0372(5) Uani 1 1 d .
H18 H 0.5835 0.7373 0.4900 0.045 Uiso 1 1 calc R
C19 C 0.47580(14) 0.7621(3) 0.54972(9) 0.0375(5) Uani 1 1 d .
H19 H 0.5180 0.7808 0.5816 0.045 Uiso 1 1 calc R
C20 C 0.37635(14) 0.7619(3) 0.55830(9) 0.0337(4) Uani 1 1 d .
H20 H 0.3509 0.7783 0.5959 0.040 Uiso 1 1 calc R
C21 C 0.06519(13) 0.8505(2) 0.55824(8) 0.0243(4) Uani 1 1 d .
C22 C 0.00500(13) 0.7361(3) 0.52655(8) 0.0270(4) Uani 1 1 d .
H22 H 0.0324 0.6601 0.4980 0.032 Uiso 1 1 calc R
C23 C -0.09393(13) 0.7321(3) 0.53621(8) 0.0285(4) Uani 1 1 d .
H23 H -0.1347 0.6529 0.5150 0.034 Uiso 1 1 calc R
C24 C -0.13234(13) 0.8460(3) 0.57749(8) 0.0264(4) Uani 1 1 d .
C25 C -0.07519(14) 0.9630(3) 0.60904(9) 0.0322(4) Uani 1 1 d .
H25 H -0.1033 1.0410 0.6369 0.039 Uiso 1 1 calc R
C26 C 0.02430(14) 0.9641(3) 0.59919(9) 0.0311(4) Uani 1 1 d .
H26 H 0.0648 1.0432 0.6207 0.037 Uiso 1 1 calc R
C27 C 0.17095(13) 0.8503(3) 0.54964(8) 0.0268(4) Uani 1 1 d .
H27 H 0.2097 0.9377 0.5689 0.032 Uiso 1 1 calc R
C28 C 0.28832(14) 0.6813(3) 0.40916(9) 0.0314(4) Uani 1 1 d .
N1 N 0.71874(11) 0.4261(2) 0.30106(7) 0.0259(3) Uani 1 1 d .
N2 N 0.74267(14) 0.6948(3) 0.42183(8) 0.0408(4) Uani 1 1 d .
N3 N 0.21151(11) 0.7354(2) 0.51695(7) 0.0275(3) Uani 1 1 d .
N4 N 0.23875(14) 0.6643(3) 0.37012(8) 0.0424(4) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 118.92(17)
C6 C1 N1 124.34(16)
C2 C1 N1 116.70(16)
C3 C2 C1 120.55(17)
C3 C2 C14 120.51(17)
C1 C2 C14 118.90(16)
C4 C3 C2 119.89(17)
C4 C3 H3 120.
C2 C3 H3 120.
C3 C4 C5 119.62(17)
C3 C4 H4 120.
C5 C4 H4 120.
C6 C5 C4 120.82(19)
C6 C5 H5 120
C4 C5 H5 120
C5 C6 C1 120.17(18)
C5 C6 H6 120
C1 C6 H6 120
C12 C7 C8 118.79(17)
C12 C7 C13 120.00(17)
C8 C7 C13 121.20(17)
C9 C8 C7 120.58(18)
C9 C8 H8 120
C7 C8 H8 120
C8 C9 C10 119.15(18)
C8 C9 H9 120.
C10 C9 H9 120.
C11 C10 C9 121.94(17)
C11 C10 Br1 119.58(14)
C9 C10 Br1 118.48(14)
C10 C11 C12 118.37(18)
C10 C11 H11 121
C12 C11 H11 121
C11 C12 C7 121.17(18)
C11 C12 H12 119.
C7 C12 H12 119.
N1 C13 C7 121.55(17)
N1 C13 H13 119.
C7 C13 H13 119.
N2 C14 C2 178.5(2)
C20 C15 C16 118.60(17)
C20 C15 N3 123.77(17)
C16 C15 N3 117.56(16)
C17 C16 C15 120.77(17)
C17 C16 C28 120.37(17)
C15 C16 C28 118.81(17)
C18 C17 C16 120.04(18)
C18 C17 H17 120.
C16 C17 H17 120.
C17 C18 C19 119.19(18)
C17 C18 H18 120.
C19 C18 H18 120.
C20 C19 C18 121.21(19)
C20 C19 H19 119.
C18 C19 H19 119.
C19 C20 C15 120.13(19)
C19 C20 H20 120
C15 C20 H20 120
C26 C21 C22 119.25(17)
C26 C21 C27 119.74(17)
C22 C21 C27 121.00(17)
C23 C22 C21 120.82(17)
C23 C22 H22 120
C21 C22 H22 120
C22 C23 C24 118.53(17)
C22 C23 H23 121
C24 C23 H23 121
C25 C24 C23 122.24(17)
C25 C24 Br2 119.38(14)
C23 C24 Br2 118.38(14)
C24 C25 C26 118.50(18)
C24 C25 H25 121
C26 C25 H25 121
C25 C26 C21 120.66(18)
C25 C26 H26 120
C21 C26 H26 120
N3 C27 C21 121.21(17)
N3 C27 H27 119.
C21 C27 H27 119.
N4 C28 C16 178.1(2)
C13 N1 C1 119.35(16)
C27 N3 C15 118.63(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.8962(18)
Br2 C24 1.8963(18)
C1 C6 1.392(3)
C1 C2 1.404(3)
C1 N1 1.412(2)
C2 C3 1.396(3)
C2 C14 1.439(3)
C3 C4 1.387(3)
C3 H3 0.95
C4 C5 1.390(3)
C4 H4 0.95
C5 C6 1.389(3)
C5 H5 0.95
C6 H6 0.95
C7 C12 1.394(3)
C7 C8 1.394(3)
C7 C13 1.465(3)
C8 C9 1.377(3)
C8 H8 0.95
C9 C10 1.385(3)
C9 H9 0.95
C10 C11 1.375(3)
C11 C12 1.386(3)
C11 H11 0.95
C12 H12 0.95
C13 N1 1.269(2)
C13 H13 0.95
C14 N2 1.148(3)
C15 C20 1.391(3)
C15 C16 1.400(3)
C15 N3 1.410(2)
C16 C17 1.393(3)
C16 C28 1.446(3)
C17 C18 1.381(3)
C17 H17 0.95
C18 C19 1.389(3)
C18 H18 0.95
C19 C20 1.383(3)
C19 H19 0.95
C20 H20 0.95
C21 C26 1.390(3)
C21 C22 1.395(3)
C21 C27 1.470(2)
C22 C23 1.381(3)
C22 H22 0.95
C23 C24 1.384(3)
C23 H23 0.95
C24 C25 1.380(3)
C25 C26 1.389(3)
C25 H25 0.95
C26 H26 0.95
C27 N3 1.271(2)
C27 H27 0.95
C28 N4 1.141(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
C6 C1 C2 C3 1.6(3)
N1 C1 C2 C3 179.29(16)
C6 C1 C2 C14 179.54(17)
N1 C1 C2 C14 -2.7(2)
C1 C2 C3 C4 -1.5(3)
C14 C2 C3 C4 -179.47(18)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 0.6(3)
C4 C5 C6 C1 -0.6(3)
C2 C1 C6 C5 -0.5(3)
N1 C1 C6 C5 -178.04(17)
C12 C7 C8 C9 -0.4(3)
C13 C7 C8 C9 178.69(19)
C7 C8 C9 C10 0.4(3)
C8 C9 C10 C11 0.2(3)
C8 C9 C10 Br1 -178.67(16)
C9 C10 C11 C12 -0.7(3)
Br1 C10 C11 C12 178.16(16)
C10 C11 C12 C7 0.7(3)
C8 C7 C12 C11 -0.1(3)
C13 C7 C12 C11 -179.22(19)
C12 C7 C13 N1 -176.24(19)
C8 C7 C13 N1 4.7(3)
C20 C15 C16 C17 -2.3(3)
N3 C15 C16 C17 -179.63(18)
C20 C15 C16 C28 -179.95(19)
N3 C15 C16 C28 2.8(3)
C15 C16 C17 C18 0.4(3)
C28 C16 C17 C18 177.9(2)
C16 C17 C18 C19 1.3(3)
C17 C18 C19 C20 -0.9(4)
C18 C19 C20 C15 -1.1(4)
C16 C15 C20 C19 2.7(3)
N3 C15 C20 C19 179.8(2)
C26 C21 C22 C23 -1.3(3)
C27 C21 C22 C23 177.67(17)
C21 C22 C23 C24 0.9(3)
C22 C23 C24 C25 0.1(3)
C22 C23 C24 Br2 -179.26(14)
C23 C24 C25 C26 -0.7(3)
Br2 C24 C25 C26 178.62(15)
C24 C25 C26 C21 0.3(3)
C22 C21 C26 C25 0.7(3)
C27 C21 C26 C25 -178.34(18)
C26 C21 C27 N3 172.65(18)
C22 C21 C27 N3 -6.3(3)
C7 C13 N1 C1 -179.13(16)
C6 C1 N1 C13 -39.6(3)
C2 C1 N1 C13 142.83(18)
C21 C27 N3 C15 -177.78(16)
C20 C15 N3 C27 42.0(3)
C16 C15 N3 C27 -140.88(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146830
