#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:20:24 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/77/7127784.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_7127784
loop_
_publ_author_name
'Li, Heng'
'Lv, Fan'
'Guo, Xing'
'Wu, Qinghua'
'Wu, Hao'
'Tang, Bing'
'Yu, Changjiang'
'Wang, Hua'
'Jiao, Lijuan'
'Hao, Erhong'
_publ_section_title
;
 Direct C-H alkoxylation of BODIPY dyes via cation radical accelerated
 oxidative nucleophilic hydrogen substitution: a new route to building
 blocks for functionalized BODIPYs.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1647
_journal_page_last               1650
_journal_paper_doi               10.1039/d0cc07961h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C16 H11 B Cl2 F2 N2 O'
_chemical_formula_sum            'C16 H11 B Cl2 F2 N2 O'
_chemical_formula_weight         366.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-11-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                114.913(2)
_cell_angle_beta                 91.931(3)
_cell_angle_gamma                96.868(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5368(3)
_cell_length_b                   10.9882(6)
_cell_length_c                   12.5935(7)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.15
_cell_volume                     810.95(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.895
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22138
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         3.153
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.1057
_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)+(0.0127P)²+2.7081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2498
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc07961h2.cif
_cod_data_source_block           mo_20200714c_0m
_cod_depositor_comments
'Adding full bibliography for 7127784--7127786.cif.'
_cod_original_cell_volume        810.95(7)
_cod_database_code               7127784
_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   0.920
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl1 Cl 0.8638(2) 0.72483(13) 1.01516(12) 0.0505(4) Uani 1 1 d . . . . .
Cl2 Cl 0.4167(3) 0.42493(16) 0.59634(14) 0.0686(5) Uani 1 1 d . . . . .
F1 F 0.6056(6) 0.9506(5) 0.6395(4) 0.0836(13) Uani 1 1 d . . . . .
F2 F 0.8201(6) 1.0487(3) 0.8047(4) 0.0790(12) Uani 1 1 d . . . . .
O1 O 1.0228(6) 0.8903(4) 0.5719(4) 0.0601(11) Uani 1 1 d . . . . .
N1 N 0.8259(6) 0.8138(4) 0.6828(3) 0.0352(9) Uani 1 1 d . . . . .
N2 N 0.5277(6) 0.8890(4) 0.7956(3) 0.0373(9) Uani 1 1 d . . . . .
C1 C 0.6264(10) 0.3379(5) 0.8505(6) 0.0567(16) Uani 1 1 d . . . . .
H1 H 0.624747 0.261093 0.864434 0.068 Uiso 1 1 calc R U . . .
C2 C 0.5297(10) 0.3258(6) 0.7481(6) 0.0567(15) Uani 1 1 d . . . . .
H2 H 0.460096 0.242464 0.693714 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5370(8) 0.4404(5) 0.7263(5) 0.0444(12) Uani 1 1 d . . . . .
C4 C 0.6412(7) 0.5655(5) 0.8059(4) 0.0364(11) Uani 1 1 d . . . . .
C5 C 0.7342(7) 0.5724(5) 0.9105(4) 0.0378(11) Uani 1 1 d . . . . .
C6 C 0.7254(9) 0.4594(5) 0.9332(5) 0.0508(14) Uani 1 1 d . . . . .
H6 H 0.786069 0.466059 1.003657 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6575(7) 0.6862(4) 0.7797(4) 0.0323(10) Uani 1 1 d . . . . .
C8 C 0.5167(7) 0.7786(5) 0.8219(4) 0.0350(10) Uani 1 1 d . . . . .
C9 C 0.3493(8) 0.7821(5) 0.8887(4) 0.0427(12) Uani 1 1 d . . . . .
H9 H 0.306256 0.719653 0.918273 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2599(8) 0.8939(5) 0.9028(5) 0.0481(13) Uani 1 1 d . . . . .
H10 H 0.145773 0.921711 0.943873 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3721(8) 0.9579(5) 0.8443(5) 0.0458(13) Uani 1 1 d . . . . .
H11 H 0.344113 1.036494 0.839357 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8096(7) 0.7039(4) 0.7128(4) 0.0332(10) Uani 1 1 d . . . . .
C13 C 0.9640(8) 0.6254(5) 0.6594(4) 0.0435(12) Uani 1 1 d . . . . .
H13 H 0.988867 0.546783 0.665182 0.052 Uiso 1 1 calc R U . . .
C14 C 1.0710(8) 0.6840(5) 0.5977(4) 0.0445(12) Uani 1 1 d . . . . .
H14 H 1.181195 0.653742 0.553794 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9804(8) 0.7996(5) 0.6142(4) 0.0414(12) Uani 1 1 d . . . . .
C16 C 1.1648(11) 0.8590(8) 0.4813(7) 0.084(2) Uani 1 1 d . . . . .
H16A H 1.105021 0.778836 0.413267 0.126 Uiso 1 1 calc R U . . .
H16B H 1.292581 0.843769 0.510156 0.126 Uiso 1 1 calc R U . . .
H16C H 1.190975 0.933565 0.460373 0.126 Uiso 1 1 calc R U . . .
B1 B 0.6954(10) 0.9314(6) 0.7298(6) 0.0428(14) 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'
Cl Cl 0.1484 0.1585 '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'
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
C15 O1 C16 116.4(5) . . ?
C12 N1 B1 125.0(4) . . ?
C15 N1 C12 106.6(4) . . ?
C15 N1 B1 128.4(4) . . ?
C8 N2 B1 126.3(4) . . ?
C11 N2 C8 107.5(4) . . ?
C11 N2 B1 126.0(4) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C6 C1 C2 121.9(5) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(5) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 Cl2 118.9(4) . . ?
C4 C3 Cl2 119.6(4) . . ?
C4 C3 C2 121.5(5) . . ?
C3 C4 C5 117.1(4) . . ?
C3 C4 C7 121.3(5) . . ?
C5 C4 C7 121.5(4) . . ?
C4 C5 Cl1 120.1(3) . . ?
C6 C5 Cl1 118.3(4) . . ?
C6 C5 C4 121.6(5) . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C4 119.9(4) . . ?
C12 C7 C4 119.1(4) . . ?
C12 C7 C8 121.0(4) . . ?
N2 C8 C7 120.2(4) . . ?
N2 C8 C9 107.9(4) . . ?
C9 C8 C7 131.9(4) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 C8 107.8(4) . . ?
C10 C9 H9 126.1 . . ?
C9 C10 H10 126.5 . . ?
C9 C10 C11 107.0(4) . . ?
C11 C10 H10 126.5 . . ?
N2 C11 C10 109.8(4) . . ?
N2 C11 H11 125.1 . . ?
C10 C11 H11 125.1 . . ?
N1 C12 C13 107.5(4) . . ?
C7 C12 N1 120.9(4) . . ?
C7 C12 C13 131.6(4) . . ?
C12 C13 H13 125.7 . . ?
C14 C13 C12 108.6(4) . . ?
C14 C13 H13 125.7 . . ?
C13 C14 H14 127.1 . . ?
C13 C14 C15 105.8(4) . . ?
C15 C14 H14 127.1 . . ?
O1 C15 N1 117.9(4) . . ?
O1 C15 C14 130.5(5) . . ?
N1 C15 C14 111.6(4) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 B1 F2 109.5(5) . . ?
F1 B1 N1 111.0(5) . . ?
F1 B1 N2 110.1(5) . . ?
F2 B1 N1 109.5(5) . . ?
F2 B1 N2 110.7(5) . . ?
N2 B1 N1 106.0(4) . . ?
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
C1 H1 0.9300 . ?
C1 C2 1.365(8) . ?
C1 C6 1.365(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(7) . ?
C3 Cl2 1.724(6) . ?
C3 C4 1.388(7) . ?
C4 C5 1.401(7) . ?
C4 C7 1.488(6) . ?
C5 Cl1 1.728(5) . ?
C5 C6 1.382(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(7) . ?
C7 C12 1.373(6) . ?
C8 N2 1.382(6) . ?
C8 C9 1.396(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(7) . ?
C11 N2 1.349(6) . ?
C11 H11 0.9300 . ?
C12 N1 1.402(5) . ?
C12 C13 1.407(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(7) . ?
C15 O1 1.321(6) . ?
C15 N1 1.332(6) . ?
C16 O1 1.449(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 F1 1.367(7) . ?
B1 F2 1.374(7) . ?
B1 N1 1.550(7) . ?
B1 N2 1.539(7) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C5 C6 C1 -179.0(4) . . . . ?
Cl2 C3 C4 C5 179.3(4) . . . . ?
Cl2 C3 C4 C7 -2.1(7) . . . . ?
F1 B1 N1 C12 -128.8(5) . . . . ?
F1 B1 N1 C15 55.8(7) . . . . ?
F1 B1 N2 C8 128.9(5) . . . . ?
F1 B1 N2 C11 -55.5(7) . . . . ?
F2 B1 N1 C12 110.2(5) . . . . ?
F2 B1 N1 C15 -65.2(7) . . . . ?
F2 B1 N2 C8 -109.9(5) . . . . ?
F2 B1 N2 C11 65.7(7) . . . . ?
O1 C15 N1 C12 178.4(5) . . . . ?
O1 C15 N1 B1 -5.5(8) . . . . ?
N1 C12 C13 C14 -0.5(6) . . . . ?
N1 C15 O1 C16 -169.1(5) . . . . ?
N1 B1 N2 C8 8.8(7) . . . . ?
N1 B1 N2 C11 -175.6(5) . . . . ?
N2 C8 C9 C10 -0.1(6) . . . . ?
N2 B1 N1 C12 -9.2(7) . . . . ?
N2 B1 N1 C15 175.4(5) . . . . ?
C1 C2 C3 Cl2 179.5(5) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C1 C6 C5 -2.3(9) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C2 C3 C4 C7 177.0(5) . . . . ?
C3 C4 C5 Cl1 -179.1(4) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C3 C4 C7 C8 96.0(6) . . . . ?
C3 C4 C7 C12 -83.2(6) . . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C4 C7 C8 N2 -178.4(4) . . . . ?
C4 C7 C8 C9 -0.3(8) . . . . ?
C4 C7 C12 N1 177.8(4) . . . . ?
C4 C7 C12 C13 0.4(8) . . . . ?
C5 C4 C7 C8 -85.5(6) . . . . ?
C5 C4 C7 C12 95.3(6) . . . . ?
C6 C1 C2 C3 1.6(9) . . . . ?
C7 C4 C5 Cl1 2.3(6) . . . . ?
C7 C4 C5 C6 -177.7(5) . . . . ?
C7 C8 N2 C11 178.4(4) . . . . ?
C7 C8 N2 B1 -5.3(7) . . . . ?
C7 C8 C9 C10 -178.4(5) . . . . ?
C7 C12 N1 C15 -177.3(4) . . . . ?
C7 C12 N1 B1 6.5(7) . . . . ?
C7 C12 C13 C14 177.2(5) . . . . ?
C8 C7 C12 N1 -1.3(7) . . . . ?
C8 C7 C12 C13 -178.7(5) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C9 C8 N2 C11 -0.1(6) . . . . ?
C9 C8 N2 B1 176.1(5) . . . . ?
C9 C10 C11 N2 -0.4(6) . . . . ?
C10 C11 N2 C8 0.3(6) . . . . ?
C10 C11 N2 B1 -176.0(5) . . . . ?
C12 C7 C8 N2 0.7(7) . . . . ?
C12 C7 C8 C9 178.8(5) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C12 N1 C15 0.6(5) . . . . ?
C13 C12 N1 B1 -175.6(5) . . . . ?
C13 C14 C15 O1 -178.5(6) . . . . ?
C13 C14 C15 N1 0.3(6) . . . . ?
C14 C15 O1 C16 9.7(9) . . . . ?
C14 C15 N1 C12 -0.6(6) . . . . ?
C14 C15 N1 B1 175.5(5) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.091 0.329 0.761 21.6 0.8 ?
2 -0.091 0.671 0.239 21.6 0.7 ?
