#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:52:01 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/68/7236856.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_7236856
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         'Br4 Sb, Br, C16 H20 N2'
_chemical_formula_sum            'C16 H20 Br5 N2 Sb'
_chemical_formula_weight         761.64
_chemical_name_systematic        AC-8-450K
_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
_atom_sites_solution_primary     iterative
_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
_cell_angle_beta                 99.598(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9137(5)
_cell_length_b                   15.1660(6)
_cell_length_c                   13.6160(5)
_cell_measurement_reflns_used    6017
_cell_measurement_temperature    295.00(10)
_cell_measurement_theta_max      28.5960
_cell_measurement_theta_min      3.7480
_cell_volume                     2222.13(16)
_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)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00   35.00   1.0000   31.7200
omega____ theta____ kappa____ phi______ frames
    -       10.3329  -38.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00   35.00   1.0000   31.7200
omega____ theta____ kappa____ phi______ frames
    -       10.3329  -38.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   22.00   1.0000   31.7200
omega____ theta____ kappa____ phi______ frames
    -       10.3329   19.0000   90.0000 53
;
_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      0.0538605000
_diffrn_orient_matrix_UB_12      0.0045737000
_diffrn_orient_matrix_UB_13      -0.0223686000
_diffrn_orient_matrix_UB_21      0.0215538000
_diffrn_orient_matrix_UB_22      0.0343161000
_diffrn_orient_matrix_UB_23      0.0339212000
_diffrn_orient_matrix_UB_31      0.0312848000
_diffrn_orient_matrix_UB_32      -0.0314581000
_diffrn_orient_matrix_UB_33      0.0337659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.567
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    10.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_refine_diff_density_max         1.256
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0362
_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)+(0.0199P)²+1.7458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3913
_reflns_number_total             5345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7tc02721d2.cif
_cod_data_source_block           zwc-8r
_cod_original_cell_volume        2222.15(15)
_cod_database_code               7236856
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N Bi 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.
;
_reflns_odcompleteness_completeness 99.64
_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.a Ternary CH refined with riding coordinates:
 N1(H1), C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C15(H15), C12(H12), C13(H13), C8(H8), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_olex2_submission_original_sample_id AC-8-450
_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
Sb1 Sb 0.18024(2) 0.54475(2) 0.47173(2) 0.02991(8) Uani 1 1 d .
Br1 Br 0.40192(4) 0.55173(3) 0.57773(3) 0.03319(10) Uani 1 1 d .
Br5 Br 0.17663(4) 0.73656(3) 0.54535(3) 0.04718(13) Uani 1 1 d .
Br4 Br 0.09161(4) 0.47051(3) 0.64576(3) 0.04866(13) Uani 1 1 d .
Br2 Br 0.24248(5) 0.60966(4) 0.30128(3) 0.05780(15) Uani 1 1 d .
Br3 Br 0.22259(5) 0.38369(3) 0.41208(4) 0.05934(15) Uani 1 1 d .
N2 N 0.5370(3) 0.7192(2) 0.3167(2) 0.0309(7) Uani 1 1 d .
C16 C 0.5702(5) 0.6457(3) 0.2552(3) 0.0482(12) Uani 1 1 d .
H16A H 0.5009 0.6062 0.2400 0.072 Uiso 1 1 calc GR
H16B H 0.6401 0.6144 0.2912 0.072 Uiso 1 1 calc GR
H16C H 0.5914 0.6685 0.1945 0.072 Uiso 1 1 calc GR
C3 C 0.9000(4) 0.8763(2) 0.4100(3) 0.0310(9) Uani 1 1 d .
N1 N 0.9969(3) 0.8314(2) 0.3660(2) 0.0370(8) Uani 1 1 d .
H1 H 1.0430 0.7950 0.4191 0.044 Uiso 1 1 calc R
C2 C 0.9421(5) 0.7690(3) 0.2854(4) 0.0565(13) Uani 1 1 d .
H2A H 0.8865 0.7292 0.3108 0.085 Uiso 1 1 calc GR
H2B H 1.0075 0.7361 0.2632 0.085 Uiso 1 1 calc GR
H2C H 0.8973 0.8017 0.2306 0.085 Uiso 1 1 calc GR
C14 C 0.5211(4) 0.8008(3) 0.2791(3) 0.0383(10) Uani 1 1 d .
H14 H 0.5295 0.8110 0.2132 0.046 Uiso 1 1 calc R
C4 C 0.8427(4) 0.9507(3) 0.3684(3) 0.0491(12) Uani 1 1 d .
H4 H 0.8678 0.9757 0.3126 0.059 Uiso 1 1 calc R
C11 C 0.4810(3) 0.8560(2) 0.4352(3) 0.0283(9) Uani 1 1 d .
C1 C 1.0900(4) 0.8901(3) 0.3314(4) 0.0525(12) Uani 1 1 d .
H1A H 1.0516 0.9219 0.2733 0.079 Uiso 1 1 calc GR
H1B H 1.1574 0.8553 0.3152 0.079 Uiso 1 1 calc GR
H1C H 1.1213 0.9312 0.3832 0.079 Uiso 1 1 calc GR
C15 C 0.4928(4) 0.8691(3) 0.3366(3) 0.0391(10) Uani 1 1 d .
H15 H 0.4813 0.9253 0.3092 0.047 Uiso 1 1 calc R
C12 C 0.4928(4) 0.7698(3) 0.4698(3) 0.0349(10) Uani 1 1 d .
H12 H 0.4813 0.7574 0.5346 0.042 Uiso 1 1 calc R
C13 C 0.5207(4) 0.7033(3) 0.4106(3) 0.0350(10) Uani 1 1 d .
H13 H 0.5287 0.6461 0.4354 0.042 Uiso 1 1 calc R
C9 C 0.5970(4) 0.9852(2) 0.5348(3) 0.0304(9) Uani 1 1 d .
H9 H 0.6190 0.9888 0.6074 0.036 Uiso 1 1 calc R
C8 C 0.8628(4) 0.8392(3) 0.4921(3) 0.0407(11) Uani 1 1 d .
H8 H 0.9011 0.7882 0.5202 0.049 Uiso 1 1 calc R
C6 C 0.7074(4) 0.9526(2) 0.4913(3) 0.0304(9) Uani 1 1 d .
C10 C 0.4717(4) 0.9297(2) 0.5057(3) 0.0304(9) Uani 1 1 d .
H10 H 0.4415 0.9086 0.5654 0.036 Uiso 1 1 calc R
C5 C 0.7473(4) 0.9891(3) 0.4091(3) 0.0475(12) Uani 1 1 d .
H5 H 0.7096 1.0401 0.3807 0.057 Uiso 1 1 calc R
C7 C 0.7684(4) 0.8777(3) 0.5326(3) 0.0390(10) Uani 1 1 d .
H7 H 0.7448 0.8529 0.5890 0.047 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 0.0033 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 Br4 88.213(15) . .
Br1 Sb1 Br2 96.752(16) . .
Br1 Sb1 Br3 90.801(16) . .
Br2 Sb1 Br4 174.948(18) . .
Br3 Sb1 Br4 89.517(18) . .
Br3 Sb1 Br2 89.481(19) . .
C14 N2 C16 120.6(3) . .
C14 N2 C13 120.1(3) . .
C13 N2 C16 119.3(3) . .
C4 C3 N1 121.7(3) . .
C4 C3 C8 120.0(4) . .
C8 C3 N1 118.2(3) . .
C3 N1 C2 111.5(3) . .
C3 N1 C1 115.4(3) . .
C1 N1 C2 110.9(3) . .
N2 C14 C15 120.6(4) . .
C3 C4 C5 120.2(4) . .
C15 C11 C12 116.5(3) . .
C15 C11 C10 123.1(3) . .
C12 C11 C10 120.1(3) . .
C14 C15 C11 121.0(4) . .
C13 C12 C11 121.0(4) . .
N2 C13 C12 120.8(4) . .
C6 C9 C10 120.2(3) . 3_676
C6 C9 C10 115.9(3) . .
C10 C9 C10 90.4(3) 3_676 .
C3 C8 C7 119.6(4) . .
C5 C6 C9 124.4(3) . .
C5 C6 C7 117.5(4) . .
C7 C6 C9 117.9(3) . .
C11 C10 C9 118.6(3) . 3_676
C11 C10 C9 114.0(3) . .
C9 C10 C9 89.6(3) 3_676 .
C6 C5 C4 121.0(4) . .
C8 C7 C6 121.7(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Br1 2.6045(5) .
Sb1 Br4 2.9297(5) .
Sb1 Br2 2.7097(5) .
Sb1 Br3 2.6391(5) .
N2 C16 1.475(5) .
N2 C14 1.340(5) .
N2 C13 1.341(5) .
C3 N1 1.467(5) .
C3 C4 1.366(5) .
C3 C8 1.372(5) .
N1 C2 1.496(6) .
N1 C1 1.486(5) .
C14 C15 1.365(5) .
C4 C5 1.387(6) .
C11 C15 1.385(5) .
C11 C12 1.388(5) .
C11 C10 1.487(5) .
C12 C13 1.358(5) .
C9 C6 1.512(5) .
C9 C10 1.547(5) 3_676
C9 C10 1.598(5) .
C8 C7 1.378(5) .
C6 C5 1.382(5) .
C6 C7 1.387(5) .
C10 C9 1.547(5) 3_676
