#------------------------------------------------------------------------------
#$Date: 2019-10-02 03:07:17 +0200 (Wed 02 de Oct de 2019) $
#$Revision: 218988 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/12/7701282.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_7701282
loop_
_publ_author_name
'Oswald, Iain W. H.'
'Ahn, Hyochul'
'Neilson, James Richmond'
_publ_section_title
;
 Influence of organic cation planarity on structural templating in hybrid
 metal-halides
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C9DT03207J
_journal_year                    2019
_chemical_formula_sum            'C10 H9 Bi Br2 I4 N2 O'
_chemical_formula_weight         1049.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-08-06 deposited with the CCDC.    2019-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.266(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8894(12)
_cell_length_b                   16.2437(11)
_cell_length_c                   7.7193(5)
_cell_measurement_reflns_used    6078
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.51
_cell_volume                     2011.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'APEX3 (Bruker-AXS, 2015)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Vesta (K. Momma and F. Izumi, 2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.537
_diffrn_reflns_theta_min         2.508
_diffrn_source                   'I\ms microfocus tube'
_exptl_absorpt_coefficient_mu    18.878
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.467
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.358
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         2095
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0250
_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)+(0.0265P)²+8.0203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1887
_reflns_number_total             2095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03207j2.cif
_cod_data_source_block           jrn102_a1_a
_cod_database_code               7701282
_shelx_shelxl_version_number     2017/1
_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.
;
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Bi1 Bi 0.500000 0.91986(2) 0.750000 0.03140(10) Uani 1 2 d S T P
I1 I 0.60717(2) 0.93344(2) 0.49435(5) 0.03774(11) Uani 1 1 d . . .
I2 I 0.38325(3) 0.79661(2) 0.52703(6) 0.04507(12) Uani 1 1 d . . .
Br1 Br 0.31099(5) 0.56428(4) 0.43143(10) 0.05210(18) Uani 1 1 d . . .
N1 N 0.4272(3) 0.4506(3) 0.6211(7) 0.0357(10) Uani 1 1 d . . .
H1 H 0.453176 0.494432 0.670659 0.043 Uiso 0.5 1 calc R U P
C1 C 0.3547(4) 0.4571(4) 0.4895(8) 0.0386(13) Uani 1 1 d . . .
C2 C 0.3102(4) 0.3894(5) 0.4018(9) 0.0498(16) Uani 1 1 d . . .
H2 H 0.259475 0.395277 0.310000 0.060 Uiso 1 1 calc R U .
C3 C 0.3444(5) 0.3127(5) 0.4567(10) 0.0591(19) Uani 1 1 d . . .
H3 H 0.317121 0.265692 0.399241 0.071 Uiso 1 1 calc R U .
C4 C 0.4188(5) 0.3056(4) 0.5962(10) 0.0517(17) Uani 1 1 d . . .
H4 H 0.440964 0.253969 0.635590 0.062 Uiso 1 1 calc R U .
C5 C 0.4603(4) 0.3768(3) 0.6774(8) 0.0360(12) Uani 1 1 d . . .
O1 O 0.500000 0.6065(4) 0.750000 0.080(3) Uani 1 2 d DS T P
H5 H 0.537(4) 0.653(3) 0.770(13) 0.097 Uiso 1 1 d D 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'
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'
Br Br -0.2901 2.4595 '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
I2 Bi1 I2 94.698(19) . 2_656
I2 Bi1 I1 90.163(12) . 2_656
I2 Bi1 I1 95.414(13) 2_656 2_656
I2 Bi1 I1 95.413(13) . .
I2 Bi1 I1 90.161(12) 2_656 .
I1 Bi1 I1 171.775(17) 2_656 .
I2 Bi1 I1 172.932(12) . 6_576
I2 Bi1 I1 90.584(12) 2_656 6_576
I1 Bi1 I1 84.658(11) 2_656 6_576
I1 Bi1 I1 89.254(11) . 6_576
I2 Bi1 I1 90.585(12) . 5_676
I2 Bi1 I1 172.931(12) 2_656 5_676
I1 Bi1 I1 89.254(11) 2_656 5_676
I1 Bi1 I1 84.658(11) . 5_676
I1 Bi1 I1 84.555(16) 6_576 5_676
Bi1 I1 Bi1 95.341(11) . 5_676
C1 N1 C5 120.7(5) . .
C1 N1 H1 119.6 . .
C5 N1 H1 119.6 . .
N1 C1 C2 122.8(6) . .
N1 C1 Br1 116.9(4) . .
C2 C1 Br1 120.3(5) . .
C1 C2 C3 117.1(7) . .
C1 C2 H2 121.5 . .
C3 C2 H2 121.5 . .
C4 C3 C2 120.4(6) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 119.2(6) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
N1 C5 C4 119.8(6) . .
N1 C5 C5 116.2(3) . 2_656
C4 C5 C5 124.0(4) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 I2 2.9549(4) .
Bi1 I2 2.9549(4) 2_656
Bi1 I1 3.0754(4) 2_656
Bi1 I1 3.0755(4) .
Bi1 I1 3.2206(4) 6_576
Bi1 I1 3.2206(4) 5_676
Br1 C1 1.890(7) .
N1 C1 1.328(8) .
N1 C5 1.337(7) .
N1 H1 0.8600 .
C1 C2 1.382(9) .
C2 C3 1.383(10) .
C2 H2 0.9300 .
C3 C4 1.379(10) .
C3 H3 0.9300 .
C4 C5 1.395(8) .
C4 H4 0.9300 .
C5 C5 1.453(12) 2_656
O1 H5 0.955(10) .
