#------------------------------------------------------------------------------
#$Date: 2019-10-27 22:51:20 +0200 (Sun, 27 Oct 2019) $
#$Revision: 219529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/44/4514425.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_4514425
loop_
_publ_author_name
'Fabian, David M.'
'Ganose, Alex M.'
'Ziller, Joseph W.'
'Scanlon, David O.'
'Beard, Matthew C.'
'Ardo, Shane'
_publ_section_title
;
 Influence of One Specific Carbon--Carbon Bond on the Quality, Stability,
 and Photovoltaic Performance of Hybrid Organic--Inorganic Bismuth Iodide
 Materials
;
_journal_issue                   3
_journal_name_full               'ACS Applied Energy Materials'
_journal_page_first              1579
_journal_paper_doi               10.1021/acsaem.8b01809
_journal_volume                  2
_journal_year                    2019
_chemical_formula_sum            'C10 H34 Bi2 I9 N3 O'
_chemical_formula_weight         1772.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                92.014(2)
_cell_angle_beta                 92.398(2)
_cell_angle_gamma                108.0020(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4726(10)
_cell_length_b                   12.2421(15)
_cell_length_c                   17.789(2)
_cell_measurement_reflns_used    8548
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      2.29
_cell_volume                     1751.0(4)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16809
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         1.147
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    17.978
_exptl_absorpt_correction_T_max  0.3352
_exptl_absorpt_correction_T_min  0.1592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    3.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       plate
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.062
_refine_diff_density_max         2.696
_refine_diff_density_min         -2.595
_refine_diff_density_rms         0.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         6628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0685
_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)+(0.0205P)²+101.0663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5553
_reflns_number_total             6628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ae8b01809_si_003.cif
_cod_data_source_block           sa17
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514425
_shelx_shelxl_version_number     2014/7
_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   0.112
_shelx_estimated_absorpt_t_max   0.402
_exptl_absorpt_special_details
; 
Reflections not merged 
19788 Corrected reflections written to file sa17s.hkl 
Estimated minimum and maximum transmission:  0.1592  0.3352 
The ratio (0.4749) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.8000 
Lambda/2 correction factor = 0.00150 
;
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.34679(8) 0.65671(6) 0.68671(4) 0.02665(18) Uani 1 1 d . . . . .
Bi2 Bi 0.18499(8) 0.37371(6) 0.81807(4) 0.02622(18) Uani 1 1 d . . . . .
I1 I 0.48546(18) 0.43887(12) 0.70202(8) 0.0368(3) Uani 1 1 d . . . . .
I2 I -0.0037(11) 0.4599(13) 0.6696(15) 0.028(3) Uani 0.47(6) 1 d . . P A 1
I2B I -0.0239(14) 0.4747(6) 0.6978(15) 0.029(3) Uani 0.53(6) 1 d . . P A 2
I3 I 0.34212(18) 0.65148(11) 0.86271(8) 0.0380(3) Uani 1 1 d . . . . .
I4 I 0.3739(18) 0.6338(4) 0.5155(2) 0.0359(18) Uani 0.67(4) 1 d . . P A 1
I4B I 0.301(4) 0.6397(5) 0.5211(4) 0.030(4) Uani 0.33(4) 1 d . . P A 2
I5 I 0.69270(16) 0.81428(14) 0.69895(9) 0.0456(4) Uani 1 1 d . . . . .
I6 I 0.18932(18) 0.84054(13) 0.68270(11) 0.0508(4) Uani 1 1 d . . . . .
I7 I 0.0658(2) 0.13240(12) 0.76385(10) 0.0503(4) Uani 1 1 d . . . . .
I8 I 0.4144(2) 0.33399(13) 0.93340(8) 0.0456(4) Uani 1 1 d . . . . .
I9 I -0.0797(19) 0.3585(7) 0.9267(14) 0.041(3) Uani 0.57(5) 1 d . . P A 1
I9B I -0.1141(17) 0.3557(8) 0.8984(14) 0.034(3) Uani 0.43(5) 1 d . . P A 2
N1 N 0.829(3) 0.655(2) 0.5551(15) 0.086(8) Uiso 1 1 d . . . . .
H1D H 0.8474 0.5892 0.5685 0.130 Uiso 1 1 calc R U . . .
H1E H 0.7179 0.6459 0.5549 0.130 Uiso 1 1 calc R U . . .
H1F H 0.8843 0.7137 0.5886 0.130 Uiso 1 1 calc R U . . .
N2 N -0.242(5) 0.596(3) 0.862(2) 0.145(14) Uiso 1 1 d . . . . .
H2C H -0.2136 0.5502 0.8276 0.217 Uiso 1 1 calc R U . . .
H2D H -0.3194 0.6249 0.8410 0.217 Uiso 1 1 calc R U . . .
H2E H -0.2839 0.5551 0.9024 0.217 Uiso 1 1 calc R U . . .
N3 N 0.547(5) 0.165(3) 0.773(2) 0.135(13) Uiso 1 1 d . . . . .
H3C H 0.4911 0.1409 0.7277 0.203 Uiso 1 1 calc R U . . .
H3D H 0.6458 0.2195 0.7660 0.203 Uiso 1 1 calc R U . . .
H3E H 0.4855 0.1957 0.8030 0.203 Uiso 1 1 calc R U . . .
C1 C 0.803(5) 0.867(4) 0.457(2) 0.108(13) Uiso 1 1 d . . . . .
H1A H 0.8533 0.9381 0.4311 0.162 Uiso 1 1 calc R U . . .
H1B H 0.7598 0.8862 0.5043 0.162 Uiso 1 1 calc R U . . .
H1C H 0.7115 0.8159 0.4247 0.162 Uiso 1 1 calc R U . . .
C2 C 0.912(6) 0.818(4) 0.471(3) 0.131(16) Uiso 1 1 d . . . . .
H2A H 0.9768 0.8598 0.5162 0.157 Uiso 1 1 calc R U . . .
H2B H 0.9873 0.8363 0.4289 0.157 Uiso 1 1 calc R U . . .
C3 C 0.884(6) 0.681(4) 0.485(2) 0.119(14) Uiso 1 1 d . . . . .
H3A H 0.8010 0.6327 0.4462 0.143 Uiso 1 1 calc R U . . .
H3B H 0.9896 0.6640 0.4792 0.143 Uiso 1 1 calc R U . . .
C4 C 0.055(6) 0.884(4) 0.923(3) 0.144(18) Uiso 1 1 d . . . . .
H4A H 0.0270 0.9435 0.9522 0.215 Uiso 1 1 calc R U . . .
H4B H 0.1160 0.9174 0.8791 0.215 Uiso 1 1 calc R U . . .
H4C H 0.1253 0.8511 0.9543 0.215 Uiso 1 1 calc R U . . .
C5 C -0.083(4) 0.801(3) 0.899(2) 0.087(10) Uiso 1 1 d . . . . .
H5A H -0.1198 0.8280 0.8516 0.105 Uiso 1 1 calc R U . . .
H5B H -0.1656 0.8054 0.9361 0.105 Uiso 1 1 calc R U . . .
C6 C -0.109(5) 0.682(3) 0.885(2) 0.093(11) Uiso 1 1 d . . . . .
H6A H -0.0263 0.6787 0.8480 0.111 Uiso 1 1 calc R U . . .
H6B H -0.0704 0.6563 0.9324 0.111 Uiso 1 1 calc R U . . .
C7 C 0.626(6) -0.007(4) 0.913(3) 0.131(16) Uiso 1 1 d . . . . .
H7A H 0.5744 -0.0594 0.9517 0.196 Uiso 1 1 calc R U . . .
H7B H 0.7140 0.0588 0.9368 0.196 Uiso 1 1 calc R U . . .
H7C H 0.6739 -0.0475 0.8763 0.196 Uiso 1 1 calc R U . . .
C8 C 0.511(7) 0.031(5) 0.878(3) 0.148(19) Uiso 1 1 d . . . . .
H8A H 0.4892 0.0927 0.9087 0.178 Uiso 1 1 calc R U . . .
H8B H 0.4051 -0.0331 0.8689 0.178 Uiso 1 1 calc R U . . .
C9 C 0.576(9) 0.073(6) 0.807(4) 0.22(3) Uiso 1 1 d . . . . .
H9A H 0.6986 0.0916 0.8137 0.263 Uiso 1 1 calc R U . . .
H9B H 0.5382 0.0070 0.7698 0.263 Uiso 1 1 calc R U . . .
O1 O 0.631(3) 0.170(2) 0.6411(15) 0.109(8) Uiso 1 1 d . . . . .
H1 H 0.6340 0.2302 0.6191 0.130 Uiso 1 1 calc R U . . .
C10 C 0.630(5) 0.083(3) 0.588(2) 0.105(12) Uiso 1 1 d . . . . .
H10A H 0.6233 0.1102 0.5368 0.157 Uiso 1 1 calc R U . . .
H10B H 0.5339 0.0150 0.5938 0.157 Uiso 1 1 calc R U . . .
H10C H 0.7325 0.0623 0.5948 0.157 Uiso 1 1 calc R 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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
I4B Bi1 I6 86.7(4)
I4B Bi1 I5 97.8(5)
I6 Bi1 I5 95.37(5)
I6 Bi1 I4 95.9(3)
I5 Bi1 I4 89.0(2)
I4B Bi1 I3 171.8(5)
I6 Bi1 I3 92.39(5)
I5 Bi1 I3 90.44(5)
I4 Bi1 I3 171.7(2)
I6 Bi1 I2 92.3(3)
I5 Bi1 I2 172.2(4)
I4 Bi1 I2 88.9(6)
I3 Bi1 I2 90.7(5)
I4B Bi1 I1 96.4(4)
I6 Bi1 I1 173.57(5)
I5 Bi1 I1 89.82(5)
I4 Bi1 I1 88.0(2)
I3 Bi1 I1 83.75(4)
I2 Bi1 I1 82.6(3)
I4B Bi1 I2B 89.9(7)
I6 Bi1 I2B 87.6(2)
I5 Bi1 I2B 171.9(4)
I3 Bi1 I2B 81.8(5)
I1 Bi1 I2B 86.79(18)
I9B Bi2 I8 103.5(6)
I9B Bi2 I7 93.04(15)
I8 Bi2 I7 93.49(5)
I8 Bi2 I9 92.9(5)
I7 Bi2 I9 96.4(3)
I9B Bi2 I2B 79.0(7)
I8 Bi2 I2B 167.77(14)
I7 Bi2 I2B 98.4(2)
I9B Bi2 I1 165.2(5)
I8 Bi2 I1 89.49(5)
I7 Bi2 I1 93.21(5)
I9 Bi2 I1 169.97(14)
I2B Bi2 I1 86.8(5)
I9B Bi2 I3 92.35(14)
I8 Bi2 I3 88.16(4)
I7 Bi2 I3 173.83(5)
I9 Bi2 I3 89.5(3)
I2B Bi2 I3 79.7(2)
I1 Bi2 I3 80.85(4)
I8 Bi2 I2 167.30(19)
I7 Bi2 I2 92.9(4)
I9 Bi2 I2 97.3(6)
I1 Bi2 I2 79.2(4)
I3 Bi2 I2 84.4(3)
Bi1 I1 Bi2 79.23(3)
Bi1 I2 Bi2 78.1(2)
Bi2 I2B Bi1 79.50(12)
Bi1 I3 Bi2 80.33(4)
C1 C2 C3 129(4)
N1 C3 C2 110(4)
C4 C5 C6 129(4)
N2 C6 C5 132(4)
C7 C8 C9 107(5)
N3 C9 C8 124(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Bi1 I4B 2.946(6)
Bi1 I6 2.9512(15)
Bi1 I5 2.9632(15)
Bi1 I4 3.073(6)
Bi1 I3 3.1353(17)
Bi1 I2 3.189(6)
Bi1 I1 3.2445(14)
Bi1 I2B 3.259(11)
Bi2 I9B 2.914(7)
Bi2 I8 2.9230(16)
Bi2 I7 2.9243(16)
Bi2 I9 2.988(8)
Bi2 I2B 3.235(10)
Bi2 I1 3.2679(15)
Bi2 I3 3.2999(15)
Bi2 I2 3.395(11)
N1 C3 1.37(4)
N2 C6 1.31(4)
N3 C9 1.38(7)
C1 C2 1.27(5)
C2 C3 1.65(6)
C4 C5 1.33(5)
C5 C6 1.42(4)
C7 C8 1.34(6)
C8 C9 1.45(7)
O1 C10 1.40(4)
