#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:05:19 +0100 (Sat 06 de Nov de 2021) $
#$Revision: 270407 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/90/7129094.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_7129094
loop_
_publ_author_name
'Feng, Siyang'
'Qu, Zhirong'
'Zhou, Zhikuan'
'Chen, Jiaying'
'Gai, Lizhi'
'Lu, Hua'
_publ_section_title
;
 Si-Bridged annulated BODIPYs: synthesis, unique structure and
 photophysical properties.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11689
_journal_page_last               11692
_journal_paper_doi               10.1039/d1cc04687j
_journal_volume                  57
_journal_year                    2021
_chemical_compound_source        Roomtemperature
_chemical_formula_moiety         'C15 H10 B F2 I N2'
_chemical_formula_sum            'C15 H10 B F2 I N2'
_chemical_formula_weight         393.96
_chemical_name_common            o-I-BDP
_chemical_name_systematic        o-I-BDP
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc237f5z
_audit_creation_date             2019-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-26 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.335(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7660(8)
_cell_length_b                   15.9828(16)
_cell_length_c                   12.3621(12)
_cell_measurement_reflns_used    3689
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.72
_cell_volume                     1479.8(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  'Bruker 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  0.0286
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11036
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.461
_diffrn_reflns_theta_min         2.131
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0901 before and 0.0398 after correction. The Ratio of minimum to maximum transmission is 0.7964. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.167
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0367P)²+1.2869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2914
_reflns_number_total             3842
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04687j2.cif
_cod_data_source_block           mo190507b
_cod_depositor_comments
'Adding full bibliography for 7129094--7129095.cif.'
_cod_database_code               7129094
_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_max   0.812
_shelx_estimated_absorpt_t_min   0.695
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 0.32953(3) 0.87521(2) 0.65025(2) 0.05868(11) Uani 1 1 d . . . . .
F1 F 0.0510(3) 0.56048(13) 0.30667(19) 0.0745(7) Uani 1 1 d . . . . .
F2 F -0.0755(3) 0.62484(14) 0.4296(2) 0.0705(6) Uani 1 1 d . . . . .
N1 N 0.0840(3) 0.70931(15) 0.3275(2) 0.0394(5) Uani 1 1 d . . . . .
N2 N 0.2439(4) 0.61316(15) 0.4777(2) 0.0425(6) Uani 1 1 d . . . . .
C1 C 0.2929(5) 0.5471(2) 0.5446(3) 0.0570(9) Uani 1 1 d . . . . .
H1 H 0.2244 0.4990 0.5423 0.068 Uiso 1 1 calc R . . . .
C2 C 0.4616(5) 0.5599(2) 0.6187(3) 0.0647(10) Uani 1 1 d . . . . .
H2 H 0.5235 0.5228 0.6732 0.078 Uiso 1 1 calc R . . . .
C3 C 0.5180(5) 0.6379(2) 0.5953(3) 0.0553(9) Uani 1 1 d . . . . .
H3 H 0.6254 0.6634 0.6313 0.066 Uiso 1 1 calc R . . . .
C4 C 0.3830(4) 0.67166(19) 0.5069(3) 0.0409(7) Uani 1 1 d . . . . .
C5 C 0.3718(4) 0.74699(18) 0.4504(2) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.2238(4) 0.76633(19) 0.3615(2) 0.0389(6) Uani 1 1 d . . . . .
C7 C 0.1876(4) 0.8353(2) 0.2896(3) 0.0490(8) Uani 1 1 d . . . . .
H7 H 0.2593 0.8824 0.2931 0.059 Uiso 1 1 calc R . . . .
C8 C 0.0268(5) 0.8209(2) 0.2128(3) 0.0546(9) Uani 1 1 d . . . . .
H8 H -0.0313 0.8565 0.1552 0.065 Uiso 1 1 calc R . . . .
C9 C -0.0327(4) 0.7431(2) 0.2377(3) 0.0507(8) Uani 1 1 d . . . . .
H9 H -0.1383 0.7179 0.1978 0.061 Uiso 1 1 calc R . . . .
C10 C 0.5214(4) 0.80905(19) 0.4826(2) 0.0403(7) Uani 1 1 d . . . . .
C11 C 0.6602(5) 0.8064(3) 0.4276(3) 0.0614(10) Uani 1 1 d . . . . .
H11 H 0.6589 0.7664 0.3728 0.074 Uiso 1 1 calc R . . . .
C12 C 0.7967(5) 0.8637(3) 0.4564(4) 0.0733(12) Uani 1 1 d . . . . .
H12 H 0.8884 0.8619 0.4210 0.088 Uiso 1 1 calc R . . . .
C13 C 0.7996(5) 0.9233(2) 0.5364(3) 0.0609(10) Uani 1 1 d . . . . .
H13 H 0.8924 0.9620 0.5538 0.073 Uiso 1 1 calc R . . . .
C14 C 0.6684(4) 0.9269(2) 0.5908(3) 0.0506(8) Uani 1 1 d . . . . .
H14 H 0.6721 0.9674 0.6454 0.061 Uiso 1 1 calc R . . . .
C15 C 0.5280(4) 0.86915(17) 0.5640(3) 0.0394(6) Uani 1 1 d . . . . .
B1 B 0.0692(5) 0.6239(2) 0.3840(3) 0.0455(8) Uani 1 1 d . . . . .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C6 N1 B1 125.7(2) . . ?
C9 N1 C6 106.6(3) . . ?
C9 N1 B1 127.6(3) . . ?
C1 N2 C4 107.1(3) . . ?
C1 N2 B1 127.1(3) . . ?
C4 N2 B1 125.7(2) . . ?
N2 C1 H1 124.6 . . ?
N2 C1 C2 110.7(3) . . ?
C2 C1 H1 124.6 . . ?
C1 C2 H2 126.6 . . ?
C3 C2 C1 106.8(3) . . ?
C3 C2 H2 126.6 . . ?
C2 C3 H3 126.4 . . ?
C2 C3 C4 107.3(3) . . ?
C4 C3 H3 126.4 . . ?
N2 C4 C3 108.0(3) . . ?
C5 C4 N2 120.6(3) . . ?
C5 C4 C3 131.4(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 C10 120.1(3) . . ?
C6 C5 C10 118.7(3) . . ?
N1 C6 C5 120.3(3) . . ?
N1 C6 C7 108.4(3) . . ?
C7 C6 C5 131.2(3) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 C6 107.4(3) . . ?
C8 C7 H7 126.3 . . ?
C7 C8 H8 126.5 . . ?
C7 C8 C9 107.0(3) . . ?
C9 C8 H8 126.5 . . ?
N1 C9 C8 110.6(3) . . ?
N1 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C11 C10 C5 119.2(3) . . ?
C15 C10 C5 122.0(3) . . ?
C15 C10 C11 118.8(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 I1 120.8(2) . . ?
C10 C15 C14 120.5(3) . . ?
C14 C15 I1 118.7(2) . . ?
F1 B1 F2 110.3(3) . . ?
F1 B1 N1 110.0(3) . . ?
F1 B1 N2 110.4(3) . . ?
F2 B1 N1 109.7(3) . . ?
F2 B1 N2 110.1(3) . . ?
N2 B1 N1 106.3(2) . . ?
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
I1 C15 2.096(3) . ?
F1 B1 1.374(4) . ?
F2 B1 1.384(5) . ?
N1 C6 1.394(4) . ?
N1 C9 1.347(4) . ?
N1 B1 1.552(4) . ?
N2 C1 1.334(4) . ?
N2 C4 1.402(4) . ?
N2 B1 1.542(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.401(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.407(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.399(4) . ?
C5 C10 1.499(4) . ?
C6 C7 1.397(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.419(5) . ?
C10 C15 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(4) . ?
