#------------------------------------------------------------------------------
#$Date: 2020-11-04 22:00:37 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/57/7705728.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_7705728
loop_
_publ_author_name
'Möbs, Jakob'
'Gerhard, Marina'
'Heine, Johanna'
_publ_section_title
;
 (HPy)₂(Py)CuBi₃I₁₂, a low bandgap metal
 halide photoconductor.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14397
_journal_page_last               14400
_journal_paper_doi               10.1039/d0dt03427d
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'Bi2 I9, 2(C4 H10 O2), 3(C5 H6 N)'
_chemical_formula_sum            'C23 H38 Bi2 I9 N3 O4'
_chemical_formula_weight         1980.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5623(6)
_cell_length_b                   18.8440(10)
_cell_length_c                   28.796(2)
_cell_measurement_reflns_used    12754
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.7
_cell_measurement_theta_min      2.8
_cell_volume                     4646.2(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'imaging plate area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detetor, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.829
_diffrn_reflns_theta_min         1.414
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'STOE C-Tech Mo tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.572
_exptl_absorpt_correction_T_max  0.4012
_exptl_absorpt_correction_T_min  0.2975
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Red32 1.63.4'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.831
_exptl_crystal_description       block
_exptl_crystal_F_000             3488
_exptl_crystal_size_max          0.1905
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.111
_refine_diff_density_min         -1.928
_refine_diff_density_rms         0.274
_refine_ls_abs_structure_details
;
 Flack x determined using 1470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4939
_refine_ls_number_restraints     89
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0346
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3906
_reflns_number_total             4939
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03427d2.cif
_cod_data_source_block           compound3-Bi
_cod_database_code               7705728
_shelx_shelxl_version_number     2018/3
_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   0.410
_shelx_estimated_absorpt_t_min   0.182
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C10 \\sim N2-C14
 with sigma of 0.02
 C10-C11 \\sim C11-C12 \\sim C12-C13 \\sim C13-C14
 with sigma of 0.02
 N2-C13 \\sim N2-C11
 with sigma of 0.04
 C12-C14 \\sim C12-C10 \\sim C13-C11 \\sim C14-C10
 with sigma of 0.04
3. Restrained planarity
 N2, C10, C11, C12, C13, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N2 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 N2, C10, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N2(0.5) H2(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5)
 H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C5(H5), C8(H8), C9(H9), N2(H2), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14)
7.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.47187(7) 0.18283(3) 0.32328(2) 0.02068(14) Uani 1 1 d . . . . .
I1 I 0.19811(12) 0.24453(6) 0.37116(3) 0.0285(3) Uani 1 1 d . . . . .
I2 I 0.500000 0.31287(8) 0.250000 0.0276(4) Uani 1 2 d S T P . .
I3 I 0.25344(13) 0.11947(6) 0.24223(3) 0.0275(3) Uani 1 1 d . . . . .
I4 I 0.45992(14) 0.05497(6) 0.38209(4) 0.0320(3) Uani 1 1 d . . . . .
I5 I 0.70263(13) 0.25717(6) 0.38287(3) 0.0301(3) Uani 1 1 d . . . . .
O1 O 0.1707(13) 0.3803(6) 0.4634(4) 0.030(3) Uani 1 1 d . . . . .
O2 O 0.4681(13) 0.3955(6) 0.4999(4) 0.032(3) Uani 1 1 d . . . . .
N1 N -0.1445(16) -0.0549(7) 0.3978(5) 0.028(3) Uani 1 1 d . . . . .
H1 H -0.193852 -0.087899 0.413655 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2233(18) 0.3351(8) 0.4991(5) 0.028(4) Uani 1 1 d . . . . .
H2A H 0.171571 0.288301 0.496197 0.034 Uiso 1 1 calc R . . . .
H2B H 0.194712 0.355477 0.529626 0.034 Uiso 1 1 calc R . . . .
C1 C 0.0052(18) 0.3864(10) 0.4616(6) 0.037(4) Uani 1 1 d . . . . .
H1A H -0.023539 0.426792 0.441938 0.055 Uiso 1 1 calc GR . . . .
H1B H -0.035713 0.393676 0.492984 0.055 Uiso 1 1 calc GR . . . .
H1C H -0.039173 0.342764 0.448516 0.055 Uiso 1 1 calc GR . . . .
C6 C -0.041(2) 0.0595(9) 0.3929(5) 0.031(4) Uani 1 1 d . . . . .
H6 H -0.020309 0.104568 0.406372 0.037 Uiso 1 1 calc R . . . .
C4 C 0.6328(18) 0.3928(11) 0.4969(7) 0.044(5) Uani 1 1 d . . . . .
H4A H 0.663186 0.369244 0.467919 0.066 Uiso 1 1 calc GR . . . .
H4B H 0.674437 0.366158 0.523355 0.066 Uiso 1 1 calc GR . . . .
H4C H 0.674998 0.441152 0.497277 0.066 Uiso 1 1 calc GR . . . .
C7 C 0.0087(18) 0.0455(9) 0.3497(6) 0.030(4) Uani 1 1 d . . . . .
H7 H 0.062663 0.081176 0.332786 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3963(19) 0.3257(9) 0.4966(6) 0.033(4) Uani 1 1 d . . . . .
H3A H 0.432545 0.295153 0.522461 0.040 Uiso 1 1 calc R . . . .
H3B H 0.425533 0.302721 0.466940 0.040 Uiso 1 1 calc R . . . .
C5 C -0.1223(19) 0.0092(9) 0.4181(5) 0.027(4) Uani 1 1 d . . . . .
H5 H -0.160898 0.019025 0.448323 0.032 Uiso 1 1 calc R . . . .
C8 C -0.017(2) -0.0195(9) 0.3293(6) 0.042(4) Uani 1 1 d . . . . .
H8 H 0.017923 -0.029519 0.298709 0.050 Uiso 1 1 calc R . . . .
C9 C -0.097(2) -0.0704(9) 0.3561(6) 0.033(4) Uani 1 1 d . . . . .
H9 H -0.116166 -0.116229 0.343588 0.040 Uiso 1 1 calc R . . . .
N2 N -0.008(4) 0.3000(15) 0.2620(9) 0.042(9) Uani 0.5 1 d D U . A -1
H2 H -0.012693 0.256027 0.272169 0.050 Uiso 0.5 1 calc R . . A -1
C10 C -0.071(4) 0.3530(19) 0.2883(11) 0.043(10) Uani 0.5 1 d D U . A -1
H10 H -0.121895 0.342779 0.316940 0.051 Uiso 0.5 1 calc R . . A -1
C11 C -0.060(6) 0.4223(16) 0.2722(17) 0.054(12) Uani 0.5 1 d D U . A -1
H11 H -0.104719 0.459940 0.289655 0.065 Uiso 0.5 1 calc R . . A -1
C12 C 0.016(7) 0.4368(15) 0.2309(17) 0.049(11) Uani 0.5 1 d D U . A -1
H12 H 0.027277 0.484595 0.220905 0.059 Uiso 0.5 1 calc R . . A -1
C13 C 0.075(5) 0.3824(16) 0.2040(14) 0.048(10) Uani 0.5 1 d D U . A -1
H13 H 0.123721 0.392316 0.175072 0.058 Uiso 0.5 1 calc R . . A -1
C14 C 0.063(4) 0.3135(19) 0.2198(10) 0.034(9) Uani 0.5 1 d D U . A -1
H14 H 0.103489 0.275513 0.201815 0.041 Uiso 0.5 1 calc R . . A -1
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'
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
I1 Bi1 I2 93.74(3) . . ?
I1 Bi1 I3 172.20(3) . 3_655 ?
I1 Bi1 I3 91.34(3) . . ?
I1 Bi1 I5 94.16(4) . . ?
I2 Bi1 I3 81.13(3) . 3_655 ?
I3 Bi1 I2 81.47(3) . . ?
I3 Bi1 I3 82.13(4) . 3_655 ?
I4 Bi1 I1 91.49(3) . . ?
I4 Bi1 I2 173.94(4) . . ?
I4 Bi1 I3 93.35(3) . 3_655 ?
I4 Bi1 I3 95.35(3) . . ?
I4 Bi1 I5 94.40(3) . . ?
I5 Bi1 I2 88.29(3) . . ?
I5 Bi1 I3 168.67(3) . . ?
I5 Bi1 I3 91.56(3) . 3_655 ?
Bi1 I2 Bi1 81.83(4) 3_655 . ?
Bi1 I3 Bi1 82.18(3) . 3_655 ?
C2 O1 C1 113.1(12) . . ?
C4 O2 C3 112.6(14) . . ?
C9 N1 C5 123.6(14) . . ?
O1 C2 C3 110.7(14) . . ?
C7 C6 C5 120.7(16) . . ?
C6 C7 C8 121.3(16) . . ?
O2 C3 C2 108.0(14) . . ?
N1 C5 C6 117.2(15) . . ?
C7 C8 C9 116.8(16) . . ?
N1 C9 C8 120.3(16) . . ?
C10 N2 C14 122(4) . . ?
N2 C10 C11 118(2) . . ?
C12 C11 C10 120(2) . . ?
C13 C12 C11 121(2) . . ?
C14 C13 C12 119(2) . . ?
C13 C14 N2 120(3) . . ?
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
Bi1 I1 2.9576(12) . ?
Bi1 I2 3.2429(13) . ?
Bi1 I3 3.2204(12) . ?
Bi1 I3 3.2429(12) 3_655 ?
Bi1 I4 2.9468(12) . ?
Bi1 I5 2.9682(12) . ?
O1 C2 1.410(18) . ?
O1 C1 1.423(19) . ?
O2 C4 1.414(19) . ?
O2 C3 1.456(19) . ?
N1 C5 1.36(2) . ?
N1 C9 1.30(2) . ?
C2 C3 1.49(2) . ?
C6 C7 1.34(2) . ?
C6 C5 1.38(2) . ?
C7 C8 1.37(2) . ?
C8 C9 1.41(2) . ?
N2 C10 1.37(3) . ?
N2 C14 1.38(3) . ?
C10 C11 1.39(2) . ?
C11 C12 1.38(2) . ?
C12 C13 1.38(2) . ?
C13 C14 1.38(2) . ?
