#------------------------------------------------------------------------------
#$Date: 2023-12-12 14:54:19 +0200 (Tue, 12 Dec 2023) $
#$Revision: 288248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/68/7236859.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_7236859
loop_
_publ_author_name
'Zhang, Weichuan'
'Sun, Zhihua'
'Zhang, Jing'
'Han, Shiguo'
'Ji, Chengmin'
'Li, Lina'
'Hong, Maochun'
'Luo, Junhua'
_publ_section_title
;
 Thermochromism to tune the optical bandgap of a lead-free perovskite-type
 hybrid semiconductor for efficiently enhancing photocurrent generation
;
_journal_issue                   38
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9967
_journal_paper_doi               10.1039/C7TC02721D
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'Br5 Sb, C16 H20 N2'
_chemical_formula_sum            'C16 H20 Br5 N2 Sb'
_chemical_formula_weight         761.64
_chemical_name_systematic        AC-8-400K
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-02-20 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 99.313(6)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   11.0102(6)
_cell_length_b                   15.1858(8)
_cell_length_c                   13.6416(9)
_cell_measurement_reflns_used    4077
_cell_measurement_temperature    400.01(10)
_cell_measurement_theta_max      29.1900
_cell_measurement_theta_min      3.7290
_cell_volume                     2250.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      400.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00   29.00   1.0000   30.6250
omega____ theta____ kappa____ phi______ frames
    -      -11.7391  -19.0000 -120.0000 121

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00   63.00   1.0000   30.6250
omega____ theta____ kappa____ phi______ frames
    -      -11.7391   38.0000 -150.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -64.00  -25.00   1.0000   30.6250
omega____ theta____ kappa____ phi______ frames
    -       10.4891  -38.0000    0.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0259850000
_diffrn_orient_matrix_UB_12      0.0251127000
_diffrn_orient_matrix_UB_13      -0.0420213000
_diffrn_orient_matrix_UB_21      0.0213673000
_diffrn_orient_matrix_UB_22      -0.0314339000
_diffrn_orient_matrix_UB_23      -0.0317111000
_diffrn_orient_matrix_UB_31      -0.0559298000
_diffrn_orient_matrix_UB_32      -0.0237252000
_diffrn_orient_matrix_UB_33      -0.0025817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.1268
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15239
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.726
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    10.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24371
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.248
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_refine_diff_density_max         1.563
_refine_diff_density_min         -2.094
_refine_diff_density_rms         0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0887
_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)+(0.0978P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.2256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2904
_reflns_number_total             5576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7tc02721d2.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'P 1 21/c 1'
_cod_database_code               7236859
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N Sb 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.
;
_cell_oxdiff_angle_alpha         90.057(5)
_cell_oxdiff_angle_beta          99.347(4)
_cell_oxdiff_angle_gamma         90.041(4)
_cell_oxdiff_length_a            11.0137(5)
_cell_oxdiff_length_b            15.1859(9)
_cell_oxdiff_length_c            13.6385(8)
_cell_oxdiff_measurement_reflns_used 4077
_cell_oxdiff_volume              2250.8(2)
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 1*[Sof(Br2)]+1*[Sof(Br2A)]+1*[Sof(Br3)]+1*[Sof(Br3A)]+1*[Sof(Br4)]+1*
 [Sof(Br4A)]=3 with esd of 0.0005
3.a Ternary CH refined with riding coordinates:
 N1(H1), C10(H10), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C15(H15), C14(H14), C13(H13), C5(H5), C7(H7), C4(H4)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C2(H2A,H2B,H2C)
;
_olex2_submission_original_sample_id AC-8-400K
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.67961(6) 0.04496(4) 0.47101(6) 0.0462(3) Uani 1 1 d . . . .
Br1 Br 0.89922(9) 0.05222(7) 0.57616(9) 0.0524(3) Uani 1 1 d . . . .
Br2 Br 0.7158(14) 0.1065(17) 0.3005(16) 0.059(3) Uani 0.233(13) 1 d . P A 1
Br5 Br 0.67283(11) 0.23655(9) 0.54470(11) 0.0717(4) Uani 1 1 d . . . .
Br4 Br 0.583(2) -0.0428(19) 0.6328(18) 0.070(5) Uani 0.258(13) 1 d . P A 5
Br3 Br 0.7267(13) -0.1149(10) 0.3994(18) 0.076(3) Uani 0.359(14) 1 d . P A 3
N1 N 0.4941(8) 0.3320(6) 0.3681(8) 0.058(2) Uani 1 1 d . . . .
H1 H 0.5384 0.2955 0.4214 0.070 Uiso 1 1 calc R . . .
N2 N -0.0354(7) 0.7803(5) 0.6822(6) 0.0426(19) Uani 1 1 d . . . .
C3 C 0.3962(9) 0.3769(6) 0.4078(9) 0.047(2) Uani 1 1 d . . . .
C12 C 0.0054(10) 0.7291(6) 0.5292(9) 0.053(3) Uani 1 1 d . . . .
H12 H 0.0151 0.7413 0.4641 0.063 Uiso 1 1 calc R . . .
C10 C 0.0280(9) 0.5694(7) 0.4950(9) 0.050(3) Uani 1 1 d . . . .
H10 H 0.0597 0.5902 0.4361 0.060 Uiso 1 1 calc R . . .
C1 C 0.5865(10) 0.3909(8) 0.3320(12) 0.073(4) Uani 1 1 d . . . .
H1A H 0.5499 0.4184 0.2710 0.110 Uiso 1 1 calc GR . . .
H1B H 0.6563 0.3567 0.3209 0.110 Uiso 1 1 calc GR . . .
H1C H 0.6125 0.4353 0.3810 0.110 Uiso 1 1 calc GR . . .
C9 C 0.0967(9) 0.4854(6) 0.5366(8) 0.047(2) Uani 1 1 d . . . .
H9 H 0.1187 0.4884 0.6091 0.056 Uiso 1 1 calc R . . .
C11 C 0.0189(8) 0.6442(6) 0.5654(9) 0.045(2) Uani 1 1 d . . . .
C6 C 0.2058(9) 0.4535(6) 0.4891(8) 0.048(3) Uani 1 1 d . . . .
C8 C 0.3629(10) 0.3414(8) 0.4932(9) 0.062(3) Uani 1 1 d . . . .
H8 H 0.4038 0.2923 0.5232 0.074 Uiso 1 1 calc R . . .
C16 C -0.0723(11) 0.8541(8) 0.7419(10) 0.070(4) Uani 1 1 d . . . .
H16A H -0.0260 0.8515 0.8078 0.105 Uiso 1 1 calc GR . . .
H16B H -0.1586 0.8496 0.7451 0.105 Uiso 1 1 calc GR . . .
H16C H -0.0564 0.9090 0.7115 0.105 Uiso 1 1 calc GR . . .
C15 C 0.0088(11) 0.6317(7) 0.6619(9) 0.059(3) Uani 1 1 d . . . .
H15 H 0.0209 0.5758 0.6896 0.071 Uiso 1 1 calc R . . .
C14 C -0.0189(10) 0.7003(7) 0.7191(9) 0.057(3) Uani 1 1 d . . . .
H14 H -0.0262 0.6903 0.7852 0.068 Uiso 1 1 calc R . . .
C13 C -0.0224(11) 0.7953(7) 0.5900(10) 0.064(3) Uani 1 1 d . . . .
H13 H -0.0323 0.8523 0.5651 0.076 Uiso 1 1 calc R . . .
C5 C 0.2442(11) 0.4885(7) 0.4082(10) 0.067(4) Uani 1 1 d . . . .
H5 H 0.2066 0.5390 0.3792 0.081 Uiso 1 1 calc R . . .
C7 C 0.2675(10) 0.3801(8) 0.5331(10) 0.061(3) Uani 1 1 d . . . .
H7 H 0.2445 0.3564 0.5903 0.073 Uiso 1 1 calc R . . .
C4 C 0.3399(12) 0.4494(8) 0.3680(11) 0.077(4) Uani 1 1 d . . . .
H4 H 0.3649 0.4744 0.3123 0.092 Uiso 1 1 calc R . . .
C2 C 0.4388(14) 0.2706(9) 0.2849(14) 0.097(5) Uani 1 1 d . . . .
H2A H 0.3894 0.2269 0.3107 0.145 Uiso 1 1 calc GR . . .
H2B H 0.5037 0.2422 0.2576 0.145 Uiso 1 1 calc GR . . .
H2C H 0.3884 0.3038 0.2340 0.145 Uiso 1 1 calc GR . . .
Br2A Br 0.7495(6) 0.1123(6) 0.3016(6) 0.0822(15) Uani 0.758(13) 1 d . P A 2
Br4A Br 0.5937(6) -0.0260(7) 0.6485(6) 0.0638(15) Uani 0.739(13) 1 d . P A 6
Br3A Br 0.7203(9) -0.1165(5) 0.4184(11) 0.090(3) Uani 0.652(14) 1 d . P A 4
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'
Sb Sb -0.5866 1.5461 '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
Br1 Sb1 Br5 81.37(4) . .
Br1 Sb1 Br4 174.5(4) . 3_656
Br1 Sb1 Br4 91.3(4) . .
Br1 Sb1 Br3 91.3(3) . .
Br1 Sb1 Br2A 94.94(15) . .
Br1 Sb1 Br4A 87.46(15) . .
Br1 Sb1 Br3A 90.3(2) . .
Br2 Sb1 Br1 102.4(4) . .
Br2 Sb1 Br5 88.2(5) . .
Br4 Sb1 Br5 95.3(5) 3_656 .
Br4 Sb1 Br5 98.8(5) . .
Br4 Sb1 Br4 84.9(7) . 3_656
Br3 Sb1 Br5 169.5(4) . .
Br2A Sb1 Br5 87.0(2) . .
Br4A Sb1 Br5 92.84(19) . .
Br3A Sb1 Br5 171.5(2) . .
Sb1 Br4 Sb1 95.1(7) . 3_656
C3 N1 C1 115.3(8) . .
C3 N1 C2 109.6(9) . .
C1 N1 C2 109.5(10) . .
C14 N2 C16 121.4(10) . .
C13 N2 C16 118.7(9) . .
C13 N2 C14 119.8(9) . .
C8 C3 N1 116.4(9) . .
C4 C3 N1 124.0(10) . .
C4 C3 C8 119.7(10) . .
C13 C12 C11 119.4(11) . .
C9 C10 C9 91.0(7) . 3_566
C11 C10 C9 115.0(8) . 3_566
C11 C10 C9 118.0(9) . .
C10 C9 C10 89.0(7) . 3_566
C6 C9 C10 114.7(8) . 3_566
C6 C9 C10 118.5(9) . .
C12 C11 C10 119.5(10) . .
C15 C11 C12 117.3(10) . .
C15 C11 C10 122.7(9) . .
C5 C6 C9 126.2(9) . .
C5 C6 C7 118.1(10) . .
C7 C6 C9 115.6(10) . .
C3 C8 C7 119.0(10) . .
C11 C15 C14 120.7(10) . .
N2 C14 C15 121.0(11) . .
N2 C13 C12 121.7(10) . .
C6 C5 C4 120.6(10) . .
C8 C7 C6 121.2(11) . .
C3 C4 C5 121.3(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Br1 2.6065(13) .
Sb1 Br2 2.60(2) .
Sb1 Br5 3.0830(14) .
Sb1 Br4 2.92(3) .
Sb1 Br4 3.01(2) 3_656
Sb1 Br3 2.698(16) .
Sb1 Br2A 2.749(7) .
Sb1 Br4A 2.943(8) .
Sb1 Br3A 2.614(7) .
Br4 Sb1 3.01(2) 3_656
N1 C3 1.452(12) .
N1 C1 1.496(13) .
N1 C2 1.517(18) .
N2 C16 1.480(13) .
N2 C14 1.317(13) .
N2 C13 1.309(15) .
C3 C8 1.385(15) .
C3 C4 1.336(15) .
C12 C11 1.381(13) .
C12 C13 1.368(15) .
C10 C9 1.544(13) .
C10 C9 1.603(14) 3_566
C10 C11 1.501(15) .
C9 C10 1.603(14) 3_566
C9 C6 1.533(13) .
C11 C15 1.352(16) .
C6 C5 1.352(15) .
C6 C7 1.391(14) .
C8 C7 1.390(14) .
C15 C14 1.366(15) .
C5 C4 1.396(15) .
