#------------------------------------------------------------------------------
#$Date: 2022-10-25 03:50:47 +0300 (Tue, 25 Oct 2022) $
#$Revision: 278763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061985.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061985
loop_
_publ_author_name
'Hulushe, Siya T.'
'Malan, Frederick P.'
'Hosten, Eric C.'
'Lobb, Kevin A.'
'Khanye, Setshaba D.'
'Watkins, Gareth M.'
_publ_section_title
;
 Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state
 studies and structural aspects
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D1NJ03056F
_journal_year                    2022
_chemical_formula_moiety         'C13 H8 Br N2 O3'
_chemical_formula_sum            'C13 H8 Br N2 O3'
_chemical_formula_weight         320.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2022-03-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.49820(10)
_cell_length_b                   11.5476(2)
_cell_length_c                   14.0374(2)
_cell_measurement_reflns_used    12726
_cell_measurement_temperature    210.00(10)
_cell_measurement_theta_max      78.5220
_cell_measurement_theta_min      3.1200
_cell_volume                     1212.68(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 119.00   0.50    0.05    --   46.83  73.00 139.00  186
  2  ω     24.00 119.00   0.50    0.05    --   46.83  77.00  60.00  190
  3  ω     32.00 118.00   0.50    0.05    --   46.83  57.00-120.00  172
  4  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00   0.00   80
  5  ω    -27.00  13.00   0.50    0.05    --   46.83 -19.00 -60.00   80
  6  ω    -25.00  68.00   0.50    0.05    --   46.83 -73.00  10.00  186
  7  ω     38.00 133.00   0.50    0.06    --  110.25 -77.00 -90.00  190
  8  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00   0.00   84
  9  ω     38.00 131.00   0.50    0.06    --  110.25 -73.00  10.00  186
 10  ω     38.00  80.00   0.50    0.06    --  110.25 -61.00 150.00   84
 11  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 150.00  136
 12  ω     38.00 106.00   0.50    0.06    --  110.25 -94.00 -90.00  136
 13  ω     38.00 111.00   0.50    0.06    --  110.25-125.00-180.00  146
 14  ω     98.00 178.00   0.50    0.06    --  110.25  30.00 -90.00  160
 15  ω     98.00 178.00   0.50    0.06    --  110.25  30.00 -30.00  160
 16  ω     98.00 178.00   0.50    0.06    --  110.25  30.00-150.00  160
 17  ω     88.00 140.00   0.50    0.06    --  110.25  77.00   0.00  104
 18  ω     98.00 178.00   0.50    0.06    --  110.25  30.00  60.00  160
 19  ω     89.00 178.00   0.50    0.06    --  110.25  73.00 139.00  178
 20  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00-120.00   68
 21  ω     -5.00  29.00   0.50    0.05    --  -46.83  19.00 -60.00   68
 22  ω    -68.00  26.00   0.50    0.05    --  -46.83  73.00 139.00  188
 23  ω   -123.00 -29.00   0.50    0.06    -- -102.00  73.00 139.00  188
 24  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 120.00   86
 25  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00  90.00   86
 26  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00   0.00   86
 27  ω    -72.00 -29.00   0.50    0.06    -- -102.00  61.00 -30.00   86
 28  ω   -112.00 -29.00   0.50    0.06    -- -102.00 125.00-120.00  166
 29  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00 -60.00  188
 30  ω   -118.00 -24.00   0.50    0.05    --  -46.83 -77.00  30.00  188
 31  ω   -175.00 -81.00   0.50    0.06    -- -102.00 -73.00  10.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1556919000
_diffrn_orient_matrix_UB_12      -0.0289614000
_diffrn_orient_matrix_UB_13      0.0621287000
_diffrn_orient_matrix_UB_21      0.1051217000
_diffrn_orient_matrix_UB_22      -0.1048397000
_diffrn_orient_matrix_UB_23      0.0421446000
_diffrn_orient_matrix_UB_31      0.0842154000
_diffrn_orient_matrix_UB_32      0.0773318000
_diffrn_orient_matrix_UB_33      0.0803833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.855
_diffrn_reflns_theta_min         4.964
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             636
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0484P)²+0.7965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2399
_reflns_number_total             2542
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f3.cif
_cod_data_source_block           sh36_210_auto
_cod_database_code               7061985
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C10 H10 N4 O4 Br'
_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.
;
_diffrn_oxdiff_digest_frames
;
01af40cdf37c4d69c79936b26c90f38c92000410690
;
_diffrn_oxdiff_digest_hkl
;
01b9340e8b04aa4e9960c8d3459395b68173ce
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C5(H5), C13(H13), C10(H10), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.630
loop_
_space_group_symop_operation_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_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
Br15 Br 0.08918(3) 0.60446(2) 0.24027(2) 0.04275(12) Uani 1 1 d . . . . .
O19 O 0.1105(2) 0.35741(15) 0.40570(11) 0.0404(4) Uani 1 1 d . . . . .
O18 O 0.4204(3) 0.11607(16) 0.77795(15) 0.0521(5) Uani 1 1 d . . . . .
N8 N 0.2162(2) 0.56686(16) 0.44802(12) 0.0310(4) Uani 1 1 d . . . . .
O17 O 0.4525(3) 0.29511(19) 0.81892(13) 0.0599(5) Uani 1 1 d . . . . .
N16 N 0.4066(2) 0.2200(2) 0.76092(13) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.2731(3) 0.40760(17) 0.55300(15) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.1753(3) 0.71778(18) 0.32929(15) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.3459(3) 0.37053(19) 0.64212(15) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.403675 0.423584 0.684578 0.039 Uiso 1 1 calc R . . . .
C9 C 0.2287(3) 0.68479(18) 0.42284(15) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.1868(3) 0.32580(19) 0.49076(15) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.3323(3) 0.25596(19) 0.66726(15) 0.0328(4) Uani 1 1 d . . . . .
C4 C 0.2515(3) 0.17439(19) 0.60554(16) 0.0364(5) Uani 1 1 d . . . . .
H4 H 0.246537 0.096202 0.623794 0.044 Uiso 1 1 calc R . . . .
C7 C 0.2877(3) 0.52820(18) 0.52717(14) 0.0314(4) Uani 1 1 d . . . . .
H7 H 0.350881 0.579270 0.569261 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1792(3) 0.2091(2) 0.51777(16) 0.0374(5) Uani 1 1 d . . . . .
H5 H 0.124528 0.154445 0.475619 0.045 Uiso 1 1 calc R . . . .
C13 C 0.1829(3) 0.8317(2) 0.29971(17) 0.0384(5) Uani 1 1 d . . . . .
H13 H 0.145401 0.851765 0.236613 0.046 Uiso 1 1 calc R . . . .
C10 C 0.2874(3) 0.7721(2) 0.48624(16) 0.0386(5) Uani 1 1 d . . . . .
H10 H 0.320440 0.753130 0.550132 0.046 Uiso 1 1 calc R . . . .
C11 C 0.2979(4) 0.8856(2) 0.45679(19) 0.0431(5) Uani 1 1 d . . . . .
H11 H 0.340489 0.942816 0.500228 0.052 Uiso 1 1 calc R . . . .
C12 C 0.2459(3) 0.9160(2) 0.3633(2) 0.0423(5) Uani 1 1 d . . . . .
H12 H 0.253423 0.993460 0.343340 0.051 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N8 C9 121.49(18) . . ?
O18 N16 C3 118.6(2) . . ?
O17 N16 O18 123.2(2) . . ?
O17 N16 C3 118.2(2) . . ?
C2 C1 C6 118.90(19) . . ?
C2 C1 C7 119.22(19) . . ?
C6 C1 C7 121.88(19) . . ?
C9 C14 Br15 119.64(16) . . ?
C13 C14 Br15 118.62(16) . . ?
C13 C14 C9 121.7(2) . . ?
C3 C2 C1 119.6(2) . . ?
C14 C9 N8 118.55(18) . . ?
C10 C9 N8 124.08(19) . . ?
C10 C9 C14 117.4(2) . . ?
O19 C6 C1 121.26(19) . . ?
O19 C6 C5 118.72(19) . . ?
C5 C6 C1 120.0(2) . . ?
C2 C3 N16 118.5(2) . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 N16 119.6(2) . . ?
C5 C4 C3 119.4(2) . . ?
N8 C7 C1 121.28(19) . . ?
C4 C5 C6 120.2(2) . . ?
C14 C13 C12 119.7(2) . . ?
C11 C10 C9 121.2(2) . . ?
C10 C11 C12 120.4(2) . . ?
C13 C12 C11 119.6(2) . . ?
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
Br15 C14 1.893(2) . ?
O19 C6 1.339(3) . ?
O18 N16 1.226(3) . ?
N8 C9 1.412(3) . ?
N8 C7 1.281(3) . ?
O17 N16 1.223(3) . ?
N16 C3 1.454(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.414(3) . ?
C1 C7 1.445(3) . ?
C14 C9 1.400(3) . ?
C14 C13 1.382(3) . ?
C2 C3 1.375(3) . ?
C9 C10 1.396(3) . ?
C6 C5 1.402(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.372(3) . ?
C13 C12 1.382(4) . ?
C10 C11 1.378(3) . ?
C11 C12 1.389(4) . ?
