#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:06:54 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/38/7243803.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_7243803
loop_
_publ_author_name
'Adcock, Alyssa K.'
'Marwitz, Alexander C.'
'Sanz, Lulio A.'
'Lee Ayscue, R.'
'Bertke, Jeffery A.'
'Knope, Karah E.'
_publ_section_title
;
 Synthesis, structural characterization, and luminescence properties of
 heteroleptic bismuth-organic compounds
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8183
_journal_page_last               8197
_journal_paper_doi               10.1039/D1CE01242H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C32 H28 Bi2 N8 O8, 2(N O3)'
_chemical_formula_sum            'C32 H28 Bi2 N10 O14'
_chemical_formula_weight         1194.60
_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_method           SHELXL-2018/3
_audit_update_record
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0626(5)
_cell_length_b                   13.5522(6)
_cell_length_c                   11.9227(5)
_cell_measurement_reflns_used    7938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.28
_cell_volume                     1782.70(14)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_molecular_graphics    'ShelXle (Sheldrick, 2011)'
_computing_publication_material  'enCIFer V1.6.1. (IUCr, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23111
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_min         2.380
_exptl_absorpt_coefficient_mu    9.944
_exptl_absorpt_correction_T_max  0.7361
_exptl_absorpt_correction_T_min  0.6042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.056
_refine_diff_density_max         2.297
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0277
_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)+(0.0080P)²+4.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0417
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2845
_reflns_number_total             3652
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01242h2.cif
_cod_data_source_block           p21onn_a
_cod_depositor_comments
'Adding full bibliography for 7243803--7243808.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7243803
_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_min   0.427
_shelx_estimated_absorpt_t_max   0.606
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.48971(2) 0.56062(2) 0.35468(2) 0.01184(6) Uani 1 1 d . . . . .
C11 C 0.2592(5) 0.6351(4) 0.4941(4) 0.0165(12) Uani 1 1 d . . . . .
H11 H 0.324687 0.657916 0.543286 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1430(4) 0.6523(4) 0.5220(4) 0.0164(12) Uani 1 1 d . . . . .
H12 H 0.128256 0.686468 0.589239 0.020 Uiso 1 1 calc R U . . .
C13 C 0.0474(5) 0.6188(4) 0.4503(4) 0.0195(12) Uani 1 1 d . . . . .
H13 H -0.034062 0.628562 0.468094 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0728(4) 0.5710(4) 0.3524(4) 0.0205(12) Uani 1 1 d . . . . .
H14 H 0.008528 0.547494 0.302307 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1916(4) 0.5574(4) 0.3273(4) 0.0145(10) Uani 1 1 d . . . . .
C16 C 0.2253(4) 0.5082(4) 0.2229(4) 0.0141(11) Uani 1 1 d . . . . .
C17 C 0.1390(4) 0.4863(4) 0.1356(4) 0.0172(12) Uani 1 1 d . . . . .
H17 H 0.056684 0.504896 0.139984 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1752(4) 0.4371(4) 0.0428(4) 0.0176(11) Uani 1 1 d . . . . .
H18 H 0.117510 0.420997 -0.017355 0.021 Uiso 1 1 calc R U . . .
C19 C 0.2952(4) 0.4112(4) 0.0372(4) 0.0183(12) Uani 1 1 d . . . . .
H19 H 0.320688 0.375820 -0.025707 0.022 Uiso 1 1 calc R U . . .
C110 C 0.3780(4) 0.4376(4) 0.1251(4) 0.0122(10) Uani 1 1 d . . . . .
C111 C 0.5081(5) 0.4123(3) 0.1242(4) 0.0162(12) Uani 1 1 d . . . . .
C112 C 0.5546(4) 0.3606(3) 0.0365(4) 0.0170(12) Uani 1 1 d . . . . .
H112 H 0.503376 0.342161 -0.027466 0.020 Uiso 1 1 calc R U . . .
C113 C 0.6767(5) 0.3360(4) 0.0432(4) 0.0186(12) Uani 1 1 d . . . . .
H113 H 0.709416 0.299642 -0.015560 0.022 Uiso 1 1 calc R U . . .
C114 C 0.7499(5) 0.3647(4) 0.1355(4) 0.0185(12) Uani 1 1 d . . . . .
H114 H 0.833609 0.348231 0.142091 0.022 Uiso 1 1 calc R U . . .
C115 C 0.6985(4) 0.4182(4) 0.2184(4) 0.0173(12) Uani 1 1 d . . . . .
H115 H 0.749315 0.439422 0.281524 0.021 Uiso 1 1 calc R U . . .
N11 N 0.2841(3) 0.5873(3) 0.3998(3) 0.0139(9) Uani 1 1 d . . . . .
N12 N 0.3423(4) 0.4857(3) 0.2155(3) 0.0132(9) Uani 1 1 d . . . . .
N13 N 0.5813(3) 0.4414(3) 0.2144(3) 0.0140(9) Uani 1 1 d . . . . .
N21 N 0.4365(4) 0.7684(3) 0.2625(3) 0.0175(10) Uani 1 1 d . . . . .
O21 O 0.3845(3) 0.6940(3) 0.2156(3) 0.0186(8) Uani 1 1 d . . . . .
O22 O 0.4714(3) 0.7615(2) 0.3653(3) 0.0174(8) Uani 1 1 d . . . . .
O23 O 0.4522(3) 0.8446(3) 0.2087(3) 0.0258(9) Uani 1 1 d . . . . .
N31 N 0.7427(4) 0.6436(3) 0.2653(4) 0.0194(10) Uani 1 1 d . . . . .
O31 O 0.6422(3) 0.6644(3) 0.2130(3) 0.0181(8) Uani 1 1 d . . . . .
O32 O 0.7418(3) 0.6077(3) 0.3634(3) 0.0213(8) Uani 1 1 d . . . . .
O33 O 0.8382(3) 0.6581(3) 0.2208(3) 0.0340(10) Uani 1 1 d . . . . .
O41 O 0.4694(3) 0.4202(2) 0.4482(2) 0.0133(8) Uani 1 1 d . . . . .
C41 C 0.4060(5) 0.3349(4) 0.4049(4) 0.0233(13) Uani 1 1 d . . . . .
H41A H 0.321755 0.352513 0.382497 0.035 Uiso 1 1 calc R U . . .
H41B H 0.407715 0.283761 0.463042 0.035 Uiso 1 1 calc R U . . .
H41C H 0.445126 0.310030 0.339380 0.035 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'
Bi Bi -4.1077 10.2566 '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
O41 Bi1 O41 67.44(13) . 3_666 ?
O41 Bi1 N11 83.35(12) . . ?
O41 Bi1 N11 82.94(12) 3_666 . ?
O41 Bi1 N12 84.19(12) . . ?
O41 Bi1 N12 141.43(12) 3_666 . ?
N11 Bi1 N12 67.74(13) . . ?
O41 Bi1 N13 81.29(12) . . ?
O41 Bi1 N13 130.78(11) 3_666 . ?
N11 Bi1 N13 131.38(12) . . ?
N12 Bi1 N13 65.00(12) . . ?
O41 Bi1 O21 146.83(11) . . ?
O41 Bi1 O21 125.82(10) 3_666 . ?
N11 Bi1 O21 70.10(11) . . ?
N12 Bi1 O21 67.79(12) . . ?
N13 Bi1 O21 101.27(11) . . ?
O41 Bi1 O22 144.85(10) . . ?
O41 Bi1 O22 81.64(10) 3_666 . ?
N11 Bi1 O22 76.42(11) . . ?
N12 Bi1 O22 113.24(11) . . ?
N13 Bi1 O22 133.35(11) . . ?
O21 Bi1 O22 47.33(10) . . ?
N11 C11 C12 122.6(5) . . ?
N11 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C13 118.7(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N11 C15 C14 120.5(4) . . ?
N11 C15 C16 116.5(4) . . ?
C14 C15 C16 123.0(4) . . ?
N12 C16 C17 121.0(4) . . ?
N12 C16 C15 117.5(4) . . ?
C17 C16 C15 121.5(4) . . ?
C18 C17 C16 118.7(5) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C110 118.8(5) . . ?
C18 C19 H19 120.6 . . ?
C110 C19 H19 120.6 . . ?
N12 C110 C19 121.0(4) . . ?
N12 C110 C111 117.5(4) . . ?
C19 C110 C111 121.6(4) . . ?
N13 C111 C112 120.7(5) . . ?
N13 C111 C110 116.8(4) . . ?
C112 C111 C110 122.5(4) . . ?
C113 C112 C111 119.4(5) . . ?
C113 C112 H112 120.3 . . ?
C111 C112 H112 120.3 . . ?
C114 C113 C112 119.5(5) . . ?
C114 C113 H113 120.2 . . ?
C112 C113 H113 120.2 . . ?
C113 C114 C115 118.2(5) . . ?
C113 C114 H114 120.9 . . ?
C115 C114 H114 120.9 . . ?
N13 C115 C114 123.3(5) . . ?
N13 C115 H115 118.4 . . ?
C114 C115 H115 118.4 . . ?
C11 N11 C15 119.2(4) . . ?
C11 N11 Bi1 121.0(3) . . ?
C15 N11 Bi1 119.7(3) . . ?
C16 N12 C110 120.4(4) . . ?
C16 N12 Bi1 117.3(3) . . ?
C110 N12 Bi1 121.5(3) . . ?
C115 N13 C111 118.9(4) . . ?
C115 N13 Bi1 123.4(3) . . ?
C111 N13 Bi1 117.1(3) . . ?
O23 N21 O22 121.5(4) . . ?
O23 N21 O21 120.8(4) . . ?
O22 N21 O21 117.7(4) . . ?
N21 O21 Bi1 95.8(2) . . ?
N21 O22 Bi1 92.7(3) . . ?
O33 N31 O32 121.6(4) . . ?
O33 N31 O31 120.1(4) . . ?
O32 N31 O31 118.3(4) . . ?
C41 O41 Bi1 125.1(3) . . ?
C41 O41 Bi1 119.9(3) . 3_666 ?
Bi1 O41 Bi1 112.56(13) . 3_666 ?
O41 C41 H41A 109.5 . . ?
O41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O41 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
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 O41 2.225(3) . ?
Bi1 O41 2.375(3) 3_666 ?
Bi1 N11 2.402(4) . ?
Bi1 N12 2.459(4) . ?
Bi1 N13 2.585(4) . ?
Bi1 O21 2.663(3) . ?
Bi1 O22 2.734(3) . ?
C11 N11 1.343(6) . ?
C11 C12 1.372(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(6) . ?
C14 H14 0.9500 . ?
C15 N11 1.353(6) . ?
C15 C16 1.483(6) . ?
C16 N12 1.339(6) . ?
C16 C17 1.393(6) . ?
C17 C18 1.375(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(7) . ?
C18 H18 0.9500 . ?
C19 C110 1.387(6) . ?
C19 H19 0.9500 . ?
C110 N12 1.344(6) . ?
C110 C111 1.480(7) . ?
C111 N13 1.357(6) . ?
C111 C112 1.388(6) . ?
C112 C113 1.387(7) . ?
C112 H112 0.9500 . ?
C113 C114 1.374(7) . ?
C113 H113 0.9500 . ?
C114 C115 1.382(7) . ?
C114 H114 0.9500 . ?
C115 N13 1.332(6) . ?
C115 H115 0.9500 . ?
N21 O23 1.235(5) . ?
N21 O22 1.261(5) . ?
N21 O21 1.270(5) . ?
N31 O33 1.232(5) . ?
N31 O32 1.267(5) . ?
N31 O31 1.267(5) . ?
O41 C41 1.429(5) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
