#------------------------------------------------------------------------------
#$Date: 2024-08-05 23:06:31 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293943 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/89/7248904.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_7248904
loop_
_publ_author_name
'Bhakta, Viki'
'Guchhait, Nikhil'
_publ_section_title
;
 Switching of photoinduced proton transfer from one six-membered
 hydrogen-bonded ring to other: a molecule of hydrazine and pH sensor.
;
_journal_issue                   28
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              19290
_journal_page_last               19301
_journal_paper_doi               10.1039/d4cp01998a
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C14 H8 Br N O3'
_chemical_formula_sum            'C14 H8 Br N O3'
_chemical_formula_weight         318.12
_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
_audit_creation_date             2023-04-11
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2024-06-16 deposited with the CCDC.	2024-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.6540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7750(2)
_cell_length_b                   11.0709(5)
_cell_length_c                   22.9812(9)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.56
_cell_volume                     1208.96(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37158
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_min         1.781
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.402
_exptl_absorpt_correction_T_max  0.506
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0153P)²+1.3868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1884
_reflns_number_total             2299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cp01998a2.cif
_cod_data_source_block           vk_a
_cod_depositor_comments          'Adding full bibliography for 7248904.cif.'
_cod_database_code               7248904
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.549
_shelx_estimated_absorpt_t_min   0.172
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C2(H2A), C3(H3), C6(H6), C1(H1), C14(H14)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br1 Br -0.36152(7) 0.52924(3) 0.40563(2) 0.04699(12) Uani 1 1 d . . . . .
O1 O 0.3974(4) 0.25067(19) 0.31391(9) 0.0374(5) Uani 1 1 d . . . . .
O2 O 0.3083(5) 0.0829(2) 0.47562(10) 0.0495(6) Uani 1 1 d . . . . .
H2 H 0.406403 0.062680 0.449925 0.074 Uiso 1 1 calc R U . . .
N1 N 0.5379(5) 0.0966(2) 0.37360(11) 0.0368(6) Uani 1 1 d . . . . .
O3 O -0.1962(6) 0.2113(2) 0.58929(11) 0.0678(8) Uani 1 1 d . . . . .
C7 C 0.3803(6) 0.1915(3) 0.36543(12) 0.0336(7) Uani 1 1 d . . . . .
C9 C 0.0319(6) 0.3434(3) 0.39004(13) 0.0339(7) Uani 1 1 d . . . . .
H9 H 0.047940 0.381319 0.354414 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1897(6) 0.2403(3) 0.40503(12) 0.0331(7) Uani 1 1 d . . . . .
C13 C 0.1651(6) 0.1835(3) 0.45907(13) 0.0346(7) Uani 1 1 d . . . . .
C5 C 0.6779(6) 0.0888(3) 0.32277(13) 0.0350(7) Uani 1 1 d . . . . .
C4 C 0.5900(6) 0.1833(3) 0.28631(13) 0.0359(7) Uani 1 1 d . . . . .
C10 C -0.1474(6) 0.3891(3) 0.42775(13) 0.0356(7) Uani 1 1 d . . . . .
C11 C -0.1716(6) 0.3350(3) 0.48125(13) 0.0381(7) Uani 1 1 d . . . . .
H11 H -0.291998 0.367410 0.506603 0.046 Uiso 1 1 calc R U . . .
C12 C -0.0161(7) 0.2323(3) 0.49706(13) 0.0371(7) Uani 1 1 d . . . . .
C2 C 0.8837(7) 0.1235(3) 0.21680(14) 0.0474(9) Uani 1 1 d . . . . .
H2A H 0.957252 0.133607 0.181130 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6842(7) 0.2045(3) 0.23267(14) 0.0425(8) Uani 1 1 d . . . . .
H3 H 0.618996 0.268524 0.208849 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8769(7) 0.0073(3) 0.30593(14) 0.0435(8) Uani 1 1 d . . . . .
H6 H 0.939065 -0.057442 0.329526 0.052 Uiso 1 1 calc R U . . .
C1 C 0.9774(7) 0.0276(3) 0.25236(14) 0.0473(8) Uani 1 1 d . . . . .
H1 H 1.111667 -0.024627 0.239816 0.057 Uiso 1 1 calc R U . . .
C14 C -0.0389(8) 0.1770(3) 0.55495(15) 0.0514(9) Uani 1 1 d . . . . .
H14 H 0.076106 0.111199 0.565551 0.062 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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 O1 C4 103.8(2) . . ?
C13 O2 H2 109.5 . . ?
C7 N1 C5 104.3(3) . . ?
O1 C7 C8 117.4(3) . . ?
N1 C7 O1 115.6(3) . . ?
N1 C7 C8 127.0(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 C13 119.7(3) . . ?
C13 C8 C7 119.9(3) . . ?
O2 C13 C8 122.4(3) . . ?
O2 C13 C12 118.3(3) . . ?
C12 C13 C8 119.3(3) . . ?
C4 C5 N1 108.5(3) . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 N1 131.7(3) . . ?
C5 C4 O1 107.8(2) . . ?
C3 C4 O1 127.6(3) . . ?
C3 C4 C5 124.6(3) . . ?
C9 C10 Br1 119.0(2) . . ?
C9 C10 C11 120.8(3) . . ?
C11 C10 Br1 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C14 120.5(3) . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 C14 119.4(3) . . ?
C3 C2 H2A 118.9 . . ?
C3 C2 C1 122.1(3) . . ?
C1 C2 H2A 118.9 . . ?
C4 C3 C2 114.9(3) . . ?
C4 C3 H3 122.6 . . ?
C2 C3 H3 122.6 . . ?
C5 C6 H6 121.7 . . ?
C1 C6 C5 116.7(3) . . ?
C1 C6 H6 121.7 . . ?
C2 C1 H1 119.0 . . ?
C6 C1 C2 121.9(3) . . ?
C6 C1 H1 119.0 . . ?
O3 C14 C12 124.4(3) . . ?
O3 C14 H14 117.8 . . ?
C12 C14 H14 117.8 . . ?
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 C10 1.899(3) . ?
O1 C7 1.363(3) . ?
O1 C4 1.385(3) . ?
O2 H2 0.8200 . ?
O2 C13 1.343(4) . ?
N1 C7 1.295(4) . ?
N1 C5 1.404(4) . ?
O3 C14 1.203(4) . ?
C7 C8 1.453(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.391(4) . ?
C9 C10 1.374(4) . ?
C8 C13 1.407(4) . ?
C13 C12 1.397(4) . ?
C5 C4 1.380(4) . ?
C5 C6 1.392(4) . ?
C4 C3 1.374(4) . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 C14 1.478(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.383(5) . ?
C2 C1 1.387(5) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.383(5) . ?
C1 H1 0.9300 . ?
C14 H14 0.9300 . ?
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 C10 C11 C12 179.6(2) . . . . ?
O1 C7 C8 C9 0.2(4) . . . . ?
O1 C7 C8 C13 -179.5(3) . . . . ?
O1 C4 C3 C2 178.3(3) . . . . ?
O2 C13 C12 C11 -178.9(3) . . . . ?
O2 C13 C12 C14 2.6(5) . . . . ?
N1 C7 C8 C9 -179.7(3) . . . . ?
N1 C7 C8 C13 0.6(5) . . . . ?
N1 C5 C4 O1 0.3(3) . . . . ?
N1 C5 C4 C3 179.7(3) . . . . ?
N1 C5 C6 C1 -178.7(3) . . . . ?
C7 O1 C4 C5 -0.4(3) . . . . ?
C7 O1 C4 C3 -179.7(3) . . . . ?
C7 N1 C5 C4 -0.1(3) . . . . ?
C7 N1 C5 C6 179.1(3) . . . . ?
C7 C8 C13 O2 -1.4(5) . . . . ?
C7 C8 C13 C12 179.2(3) . . . . ?
C9 C8 C13 O2 178.9(3) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C8 C9 C10 Br1 -179.6(2) . . . . ?
C8 C9 C10 C11 0.9(5) . . . . ?
C8 C13 C12 C11 0.6(5) . . . . ?
C8 C13 C12 C14 -177.9(3) . . . . ?
C13 C12 C14 O3 -177.6(4) . . . . ?
C5 N1 C7 O1 -0.2(3) . . . . ?
C5 N1 C7 C8 179.8(3) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C5 C6 C1 C2 -0.5(5) . . . . ?
C4 O1 C7 N1 0.3(3) . . . . ?
C4 O1 C7 C8 -179.6(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C10 C9 C8 C7 -179.9(3) . . . . ?
C10 C9 C8 C13 -0.2(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 C14 178.6(3) . . . . ?
C11 C12 C14 O3 3.9(6) . . . . ?
C3 C2 C1 C6 0.0(5) . . . . ?
C6 C5 C4 O1 -179.0(3) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
