#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:49:56 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/33/7063329.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_7063329
loop_
_publ_author_name
'Osipov, Nikita G.'
'Faraonov, Maxim A.'
'Kuzmin, Alexey V.'
'Khasanov, Salavat S.'
'Shestakov, Alexander F.'
'Denisov, Nikolay N.'
'Savinykh, Tatiana A.'
'Otsuka, Akihiro'
'Kitagawa, Hiroshi'
'Konarev, Dmitri V.'
_publ_section_title
;
 Coordination vs. oxidative rearrangement of photochromic spiropyrans upon
 reacting with FeIIICl3 and FeIIIBr3
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13526
_journal_page_last               13537
_journal_paper_doi               10.1039/D4NJ02371D
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C22 H19 N2 O, Fe Br4'
_chemical_formula_sum            'C22 H19 Br4 Fe N2 O'
_chemical_formula_weight         702.88
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2024-03-26 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.385(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9996(5)
_cell_length_b                   9.8119(2)
_cell_length_c                   15.0378(4)
_cell_measurement_reflns_used    10914
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      33.9250
_cell_measurement_theta_min      2.4180
_cell_volume                     2380.25(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    WinGx
_computing_publication_material  WinGx
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2283
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            58663
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.696
_diffrn_reflns_theta_min         2.430
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.131
_refine_diff_density_max         1.132
_refine_diff_density_min         -1.139
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         12289
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0405
_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)+(0.0316P)²+0.5134P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8432
_reflns_number_total             12289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02371d2.cif
_cod_data_source_block           Photo-FeBr4
_cod_depositor_comments
'Adding full bibliography for 7063326--7063329.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063329
_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_min   0.208
_shelx_estimated_absorpt_t_max   0.445
_shelxl_version_number           2013-2
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
C1 C 0.21429(12) 0.75033(19) -0.00979(13) 0.0128(3) Uani 1 1 d . U . . .
C2 C 0.21694(12) 0.8557(2) 0.06524(13) 0.0136(3) Uani 1 1 d . U . . .
C3 C 0.12801(13) 0.8523(2) 0.06400(13) 0.0138(3) Uani 1 1 d . U . . .
C4 C 0.08803(14) 0.9236(2) 0.11654(14) 0.0174(4) Uani 1 1 d . U . . .
H4 H 0.1166 0.9900 0.1610 0.021 Uiso 1 1 calc R U . . .
C5 C 0.00512(14) 0.8952(2) 0.10243(15) 0.0194(4) Uani 1 1 d . U . . .
H5 H -0.0233 0.9427 0.1381 0.023 Uiso 1 1 calc R U . . .
C6 C -0.03740(14) 0.7987(2) 0.03716(15) 0.0197(4) Uani 1 1 d . U . . .
H6 H -0.0940 0.7809 0.0298 0.024 Uiso 1 1 calc R U . . .
C7 C 0.00121(13) 0.7275(2) -0.01774(15) 0.0174(4) Uani 1 1 d . U . . .
H7 H -0.0274 0.6623 -0.0632 0.021 Uiso 1 1 calc R U . . .
C8 C 0.08435(13) 0.7581(2) -0.00170(13) 0.0141(3) Uani 1 1 d . U . . .
N9 N 0.13963(11) 0.69954(17) -0.04540(11) 0.0137(3) Uani 1 1 d . U . . .
C10 C 0.11049(14) 0.5969(2) -0.11947(15) 0.0204(4) Uani 1 1 d . U . . .
H10A H 0.0513 0.5800 -0.1311 0.031 Uiso 1 1 calc R U . . .
H10B H 0.1415 0.5120 -0.0998 0.031 Uiso 1 1 calc R U . . .
H10C H 0.1193 0.6302 -0.1771 0.031 Uiso 1 1 calc R U . . .
C11 C 0.27569(13) 0.8085(2) 0.16129(14) 0.0181(4) Uani 1 1 d . U . . .
H11A H 0.3331 0.8115 0.1606 0.027 Uiso 1 1 calc R U . . .
H11B H 0.2616 0.7151 0.1736 0.027 Uiso 1 1 calc R U . . .
H11C H 0.2696 0.8690 0.2105 0.027 Uiso 1 1 calc R U . . .
C12 C 0.24158(14) 0.9984(2) 0.03983(16) 0.0193(4) Uani 1 1 d . U . . .
H12A H 0.2996 0.9972 0.0413 0.029 Uiso 1 1 calc R U . . .
H12B H 0.2346 1.0653 0.0852 0.029 Uiso 1 1 calc R U . . .
H12C H 0.2061 1.0233 -0.0232 0.029 Uiso 1 1 calc R U . . .
C13 C 0.28519(12) 0.70770(19) -0.03562(13) 0.0136(3) Uani 1 1 d . U . . .
O14 O 0.35781(9) 0.77539(14) 0.00761(10) 0.0150(3) Uani 1 1 d . U . . .
C15 C 0.41360(13) 0.7156(2) -0.02843(14) 0.0143(3) Uani 1 1 d . U . . .
C16 C 0.49749(13) 0.7488(2) -0.00932(14) 0.0170(4) Uani 1 1 d . U . . .
H16 H 0.5234 0.8196 0.0328 0.020 Uiso 1 1 calc R U . . .
C17 C 0.53952(13) 0.6718(2) -0.05568(14) 0.0172(4) Uani 1 1 d . U . . .
H17 H 0.5966 0.6905 -0.0453 0.021 Uiso 1 1 calc R U . . .
C18 C 0.50106(13) 0.5643(2) -0.11927(14) 0.0151(3) Uani 1 1 d . U . . .
C19 C 0.54620(13) 0.4866(2) -0.16634(15) 0.0190(4) Uani 1 1 d . U . . .
H19 H 0.6029 0.5070 -0.1566 0.023 Uiso 1 1 calc R U . . .
C20 C 0.50944(14) 0.3830(2) -0.22537(16) 0.0210(4) Uani 1 1 d . U . . .
H20 H 0.5407 0.3328 -0.2566 0.025 Uiso 1 1 calc R U . . .
C21 C 0.42547(14) 0.3498(2) -0.24044(15) 0.0199(4) Uani 1 1 d . U . . .
H21 H 0.4007 0.2766 -0.2809 0.024 Uiso 1 1 calc R U . . .
C22 C 0.37933(13) 0.4231(2) -0.19664(14) 0.0166(4) Uani 1 1 d . U . . .
H22 H 0.3228 0.4006 -0.2068 0.020 Uiso 1 1 calc R U . . .
C23 C 0.41608(12) 0.53167(19) -0.13677(13) 0.0128(3) Uani 1 1 d . U . . .
C24 C 0.37304(12) 0.61439(19) -0.08950(13) 0.0131(3) Uani 1 1 d . U . . .
N25 N 0.29085(11) 0.61136(17) -0.09319(11) 0.0140(3) Uani 1 1 d . U . . .
Fe1 Fe 0.20617(2) 0.42529(3) 0.24384(2) 0.01504(6) Uani 1 1 d . U . . .
Br1 Br 0.22048(2) 0.39966(2) 0.09427(2) 0.02133(5) Uani 1 1 d . U . . .
Br2 Br 0.10832(2) 0.59374(2) 0.24108(2) 0.02385(5) Uani 1 1 d . U . . .
Br3 Br 0.33615(2) 0.48673(2) 0.34339(2) 0.02346(5) Uani 1 1 d . U . . .
Br4 Br 0.15848(2) 0.22488(2) 0.29209(2) 0.02743(6) Uani 1 1 d . 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'
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'
Fe Fe 0.3463 0.8444 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 C1 C13 124.36(17) . . ?
N9 C1 C2 111.10(17) . . ?
C13 C1 C2 124.49(17) . . ?
C3 C2 C1 100.41(16) . . ?
C3 C2 C12 111.54(17) . . ?
C1 C2 C12 112.33(16) . . ?
C3 C2 C11 110.80(16) . . ?
C1 C2 C11 110.40(16) . . ?
C12 C2 C11 110.94(17) . . ?
C4 C3 C8 119.7(2) . . ?
C4 C3 C2 130.79(19) . . ?
C8 C3 C2 109.51(17) . . ?
C3 C4 C5 118.05(19) . . ?
C4 C5 C6 121.4(2) . . ?
C5 C6 C7 121.5(2) . . ?
C8 C7 C6 115.61(19) . . ?
C3 C8 C7 123.70(19) . . ?
C3 C8 N9 108.33(18) . . ?
C7 C8 N9 127.94(18) . . ?
C1 N9 C8 110.64(16) . . ?
C1 N9 C10 128.53(17) . . ?
C8 N9 C10 120.83(17) . . ?
N25 C13 O14 114.91(17) . . ?
N25 C13 C1 129.21(18) . . ?
O14 C13 C1 115.87(16) . . ?
C15 O14 C13 103.78(15) . . ?
O14 C15 C24 108.03(17) . . ?
O14 C15 C16 127.52(18) . . ?
C24 C15 C16 124.45(19) . . ?
C17 C16 C15 115.34(19) . . ?
C16 C17 C18 122.84(19) . . ?
C19 C18 C23 117.68(19) . . ?
C19 C18 C17 121.52(19) . . ?
C23 C18 C17 120.79(19) . . ?
C20 C19 C18 121.1(2) . . ?
C19 C20 C21 120.6(2) . . ?
C22 C21 C20 120.2(2) . . ?
C21 C22 C23 119.8(2) . . ?
C22 C23 C18 120.62(18) . . ?
C22 C23 C24 123.81(18) . . ?
C18 C23 C24 115.56(18) . . ?
C15 C24 N25 109.21(17) . . ?
C15 C24 C23 120.98(18) . . ?
N25 C24 C23 129.81(18) . . ?
C13 N25 C24 104.06(17) . . ?
Br3 Fe1 Br4 111.847(15) . . ?
Br3 Fe1 Br2 110.793(15) . . ?
Br4 Fe1 Br2 106.684(15) . . ?
Br3 Fe1 Br1 106.247(15) . . ?
Br4 Fe1 Br1 111.042(14) . . ?
Br2 Fe1 Br1 110.284(14) . . ?
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
C1 N9 1.311(3) . ?
C1 C13 1.440(3) . ?
C1 C2 1.521(3) . ?
C2 C3 1.506(3) . ?
C2 C12 1.543(3) . ?
C2 C11 1.545(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.385(3) . ?
C4 C5 1.386(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.389(3) . ?
C8 N9 1.426(3) . ?
N9 C10 1.467(2) . ?
C13 N25 1.306(2) . ?
C13 O14 1.372(2) . ?
O14 C15 1.364(2) . ?
C15 C24 1.381(3) . ?
C15 C16 1.401(3) . ?
C16 C17 1.371(3) . ?
C17 C18 1.435(3) . ?
C18 C19 1.419(3) . ?
C18 C23 1.421(3) . ?
C19 C20 1.364(3) . ?
C20 C21 1.411(3) . ?
C21 C22 1.376(3) . ?
C22 C23 1.407(3) . ?
C23 C24 1.424(3) . ?
C24 N25 1.381(3) . ?
Fe1 Br3 2.3238(4) . ?
Fe1 Br4 2.3285(4) . ?
Fe1 Br2 2.3360(4) . ?
Fe1 Br1 2.3509(4) . ?
