#------------------------------------------------------------------------------
#$Date: 2019-11-22 23:14:48 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231536 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/33/4003361.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_4003361
loop_
_publ_author_name
'Zhang, Weichuan'
'Liu, Xitao'
'Li, Lina'
'Sun, Zhihua'
'Han, Shiguo'
'Wu, Zhenyue'
'Luo, Junhua'
_publ_section_title
;
 Triiodide-Induced Band-Edge Reconstruction of a Lead-Free
 Perovskite-Derivative Hybrid for Strong Light Absorption
;
_journal_issue                   12
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4081
_journal_paper_doi               10.1021/acs.chemmater.8b01200
_journal_volume                  30
_journal_year                    2018
_chemical_formula_moiety         'Bi0.5 I3, I1.5, 2(C6 H14 N)'
_chemical_formula_sum            'C12 H28 Bi0.5 I4.5 N2'
_chemical_formula_weight         875.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                91.017(3)
_cell_angle_beta                 102.753(3)
_cell_angle_gamma                100.403(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5348(3)
_cell_length_b                   10.2038(4)
_cell_length_c                   14.0759(6)
_cell_measurement_reflns_used    7160
_cell_measurement_temperature    290.01(10)
_cell_measurement_theta_max      28.8910
_cell_measurement_theta_min      3.5240
_cell_volume                     1173.82(8)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.01(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 0.849
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   86.00   1.0000    7.0300
omega____ theta____ kappa____ phi______ frames
    -       10.3329   77.0000  -90.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   86.00   1.0000    7.0300
omega____ theta____ kappa____ phi______ frames
    -       10.3329   77.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   65.00   1.0000    7.0300
omega____ theta____ kappa____ phi______ frames
    -      -11.5829   77.0000  150.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   99.00   1.0000    7.0300
omega____ theta____ kappa____ phi______ frames
    -       10.3329  178.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega   34.00   97.00   1.0000    7.0300
omega____ theta____ kappa____ phi______ frames
    -       10.3329 -178.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
  6 omega  -86.00  -57.00   1.0000    7.0300
omega____ theta____ kappa____ phi______ frames
    -      -11.5829  -38.0000  120.0000 29
;
_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      -0.0017753000
_diffrn_orient_matrix_UB_12      -0.0598978000
_diffrn_orient_matrix_UB_13      0.0248879000
_diffrn_orient_matrix_UB_21      -0.0866839000
_diffrn_orient_matrix_UB_22      -0.0106915000
_diffrn_orient_matrix_UB_23      -0.0104922000
_diffrn_orient_matrix_UB_31      -0.0035677000
_diffrn_orient_matrix_UB_32      -0.0362069000
_diffrn_orient_matrix_UB_33      -0.0441530000
_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     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15590
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.643
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58627
_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            Black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.478
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_refine_diff_density_max         0.664
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         5630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0310
_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)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0633
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4610
_reflns_number_total             5630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm8b01200_si_002.cif
_cod_data_source_block           WeiChuanZhang-23-(C6H13N)4I3BiI6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_colour_primary' value 'Black' was changed
to 'black' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1173.83(8)
_cod_original_formula_sum        'C12 H28 Bi0.50 I4.50 N2'
_cod_database_code               4003361
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N Bi I'
_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 99.69
_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 C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), C11(H11A,H11B), C5(H5A,H5B), C4(H4A,H4B), C10(H10A,
 H10B), C8(H8A,H8B), C2(H2A,H2B), C9(H9A,H9B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Bi1 Bi 0.5000 0.5000 0.5000 0.03325(7) Uani 1 2 d S T P
I1 I 0.42933(4) 0.48274(3) 0.27572(2) 0.04025(9) Uani 1 1 d . . .
I2 I 0.75923(4) 0.32568(3) 0.49497(2) 0.04377(9) Uani 1 1 d . . .
I3 I 0.24443(4) 0.24278(3) 0.48844(3) 0.05039(10) Uani 1 1 d . . .
I5 I 0.0000 0.0000 0.0000 0.05409(14) Uani 1 2 d S T P
I4 I 0.01197(5) 0.10779(4) 0.19626(3) 0.06318(12) Uani 1 1 d . . .
N1 N 0.8772(5) 0.5784(4) 0.3155(3) 0.0450(10) Uani 1 1 d . . .
H1A H 0.7706 0.5520 0.3117 0.054 Uiso 1 1 calc R . .
H1B H 0.9282 0.5860 0.3783 0.054 Uiso 1 1 calc R . .
N2 N 0.4480(5) 1.1137(4) 0.3083(3) 0.0492(11) Uani 1 1 d . . .
H2C H 0.4859 1.1704 0.3606 0.059 Uiso 1 1 calc R . .
H2D H 0.3526 1.1317 0.2767 0.059 Uiso 1 1 calc R . .
C7 C 0.4769(6) 0.8941(5) 0.1824(4) 0.0475(13) Uani 1 1 d . . .
H7 H 0.5821 0.8736 0.2164 0.057 Uiso 1 1 calc R . .
C11 C 0.5049(7) 1.0366(5) 0.1543(4) 0.0515(14) Uani 1 1 d . . .
H11A H 0.4032 1.0561 0.1163 0.062 Uiso 1 1 calc R . .
H11B H 0.5841 1.0482 0.1138 0.062 Uiso 1 1 calc R . .
C5 C 0.8208(7) 0.6962(5) 0.1650(4) 0.0502(13) Uani 1 1 d . . .
H5A H 0.7036 0.6707 0.1585 0.060 Uiso 1 1 calc R . .
H5B H 0.8416 0.7820 0.1369 0.060 Uiso 1 1 calc R . .
C1 C 0.8778(7) 0.5937(5) 0.1084(4) 0.0492(13) Uani 1 1 d . . .
H1 H 0.9951 0.6234 0.1128 0.059 Uiso 1 1 calc R . .
C4 C 0.9053(7) 0.7109(5) 0.2733(4) 0.0538(14) Uani 1 1 d . . .
H4A H 1.0217 0.7437 0.2812 0.065 Uiso 1 1 calc R . .
H4B H 0.8613 0.7745 0.3069 0.065 Uiso 1 1 calc R . .
C10 C 0.5664(7) 1.1337(6) 0.2430(5) 0.0610(16) Uani 1 1 d . . .
H10A H 0.6726 1.1196 0.2784 0.073 Uiso 1 1 calc R . .
H10B H 0.5787 1.2245 0.2224 0.073 Uiso 1 1 calc R . .
C8 C 0.3616(7) 0.8773(5) 0.2520(4) 0.0544(14) Uani 1 1 d . . .
H8A H 0.2543 0.8902 0.2174 0.065 Uiso 1 1 calc R . .
H8B H 0.3505 0.7871 0.2736 0.065 Uiso 1 1 calc R . .
C12 C 0.4088(8) 0.7988(6) 0.0926(4) 0.0659(17) Uani 1 1 d . . .
H12A H 0.3056 0.8177 0.0585 0.099 Uiso 1 1 calc GR . .
H12B H 0.3937 0.7086 0.1122 0.099 Uiso 1 1 calc GR . .
H12C H 0.4840 0.8098 0.0505 0.099 Uiso 1 1 calc GR . .
C2 C 0.8547(7) 0.4623(5) 0.1566(4) 0.0555(14) Uani 1 1 d . . .
H2A H 0.7386 0.4287 0.1492 0.067 Uiso 1 1 calc R . .
H2B H 0.8984 0.3980 0.1236 0.067 Uiso 1 1 calc R . .
C9 C 0.4225(8) 0.9754(6) 0.3402(4) 0.0594(15) Uani 1 1 d . . .
H9A H 0.3432 0.9651 0.3807 0.071 Uiso 1 1 calc R . .
H9B H 0.5247 0.9573 0.3787 0.071 Uiso 1 1 calc R . .
C3 C 0.9374(7) 0.4746(6) 0.2640(5) 0.0607(16) Uani 1 1 d . . .
H3A H 0.9138 0.3893 0.2923 0.073 Uiso 1 1 calc R . .
H3B H 1.0550 0.4993 0.2719 0.073 Uiso 1 1 calc R . .
C6 C 0.7916(9) 0.5802(7) 0.0019(4) 0.078(2) Uani 1 1 d . . .
H6A H 0.6757 0.5553 -0.0041 0.117 Uiso 1 1 calc GR . .
H6B H 0.8289 0.5129 -0.0311 0.117 Uiso 1 1 calc GR . .
H6C H 0.8154 0.6640 -0.0269 0.117 Uiso 1 1 calc GR . .
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
I1 Bi1 I1 180.0 . 2_666
I1 Bi1 I2 86.917(9) 2_666 2_666
I1 Bi1 I2 93.083(9) 2_666 .
I1 Bi1 I2 86.916(9) . .
I1 Bi1 I2 93.083(9) . 2_666
I2 Bi1 I2 180.0 2_666 .
I3 Bi1 I1 88.501(10) 2_666 2_666
I3 Bi1 I1 91.499(10) . 2_666
I3 Bi1 I1 88.501(10) . .
I3 Bi1 I1 91.499(10) 2_666 .
I3 Bi1 I2 88.558(10) . .
I3 Bi1 I2 91.442(10) . 2_666
I3 Bi1 I2 88.559(10) 2_666 2_666
I3 Bi1 I2 91.442(10) 2_666 .
I3 Bi1 I3 180.0 2_666 .
I4 I5 I4 180.0 2 .
C4 N1 C3 112.3(4) . .
C9 N2 C10 111.7(4) . .
C11 C7 C8 109.6(4) . .
C11 C7 C12 110.9(5) . .
C12 C7 C8 110.8(5) . .
C7 C11 C10 111.8(5) . .
C1 C5 C4 113.0(5) . .
C5 C1 C2 108.6(4) . .
C6 C1 C5 112.0(5) . .
C6 C1 C2 112.1(5) . .
N1 C4 C5 108.8(4) . .
N2 C10 C11 110.0(4) . .
C9 C8 C7 112.1(5) . .
C3 C2 C1 112.8(5) . .
N2 C9 C8 109.9(4) . .
N1 C3 C2 109.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 I1 3.0761(3) .
Bi1 I1 3.0761(3) 2_666
Bi1 I2 3.0903(3) .
Bi1 I2 3.0903(3) 2_666
Bi1 I3 3.0714(3) .
Bi1 I3 3.0714(4) 2_666
I5 I4 2.9289(5) 2
I5 I4 2.9289(5) .
N1 C4 1.488(6) .
N1 C3 1.499(7) .
N2 C10 1.501(6) .
N2 C9 1.481(7) .
C7 C11 1.505(7) .
C7 C8 1.525(7) .
C7 C12 1.520(8) .
C11 C10 1.514(8) .
C5 C1 1.514(7) .
C5 C4 1.527(7) .
C1 C2 1.514(7) .
C1 C6 1.509(8) .
C8 C9 1.515(8) .
C2 C3 1.512(8) .
