#------------------------------------------------------------------------------
#$Date: 2022-01-05 00:57:58 +0200 (Wed, 05 Jan 2022) $
#$Revision: 271796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129500.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_7129500
loop_
_publ_author_name
'Thompson, Brena L.'
'Kieffer, Ian A.'
'Heiden, Zachariah M.'
_publ_section_title
;
 Utilization of BODIPY-based redox events to manipulate the Lewis acidity
 of fluorescent boranes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06400B
_journal_year                    2022
_chemical_formula_moiety         'C30 H27 B3 Cl4 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C32 H31 B3 Cl8 N6'
_chemical_formula_weight         815.66
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-11-11 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2766(7)
_cell_length_b                   17.6234(10)
_cell_length_c                   17.1711(10)
_cell_measurement_reflns_used    9646
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.34
_cell_volume                     3715.1(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_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  0.0410
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27384
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.736
_diffrn_reflns_theta_max         24.736
_diffrn_reflns_theta_min         2.311
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1457 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.8773.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0424
_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)+(0.0341P)²+6.6332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2645
_reflns_number_total             3175
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06400b2.cif
_cod_data_source_block           bt_3_0ma
_cod_database_code               7129500
_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   0.831
_shelx_estimated_absorpt_t_min   0.663
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C1S(H1SA,H1SB)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.22704(7) 0.36179(6) 0.60034(4) 0.0605(3) Uani 1 1 d . . . . .
Cl2 Cl 0.19874(6) 0.46284(4) 0.45863(6) 0.0496(2) Uani 1 1 d . . . . .
N1 N 0.44310(17) 0.28098(11) 0.30301(12) 0.0223(5) Uani 1 1 d . . . . .
N2 N 0.22276(16) 0.30771(12) 0.44764(12) 0.0243(5) Uani 1 1 d . . . . .
N3 N 0.38628(17) 0.37756(12) 0.48734(12) 0.0232(5) Uani 1 1 d . . . . .
C1 C 0.2017(2) 0.24043(15) 0.33675(16) 0.0277(6) Uani 1 1 d . . . . .
H1 H 0.2157 0.2162 0.2884 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1033(2) 0.24128(15) 0.37644(17) 0.0324(6) Uani 1 1 d . . . . .
H2 H 0.0376 0.2176 0.3604 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1187(2) 0.28297(15) 0.44375(17) 0.0308(6) Uani 1 1 d . . . . .
H3 H 0.0641 0.2928 0.4817 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4602(2) 0.41300(15) 0.53240(15) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.4442 0.4392 0.5794 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5638(2) 0.40567(15) 0.49988(16) 0.0294(6) Uani 1 1 d . . . . .
H5 H 0.6297 0.4256 0.5204 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5524(2) 0.36402(14) 0.43242(15) 0.0254(6) Uani 1 1 d . . . . .
H6 H 0.6093 0.3497 0.3979 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4415(2) 0.34670(14) 0.42403(14) 0.0219(5) Uani 1 1 d . . . . .
C8 C 0.3862(2) 0.30242(13) 0.36909(14) 0.0211(5) Uani 1 1 d . . . . .
C9 C 0.2765(2) 0.28194(14) 0.38129(14) 0.0226(5) Uani 1 1 d . . . . .
C10 C 0.5000 0.4185(2) 0.2500 0.0242(8) Uani 1 2 d S T P . .
C11 C 0.5932(2) 0.45950(15) 0.22956(15) 0.0303(6) Uani 1 1 d . . . . .
H11 H 0.6576 0.4330 0.2154 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5932(3) 0.53831(16) 0.22954(17) 0.0398(7) Uani 1 1 d . . . . .
H12 H 0.6572 0.5654 0.2155 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5000 0.5771(2) 0.2500 0.0407(11) Uani 1 2 d S T P . .
H13 H 0.5000 0.6310 0.2500 0.049 Uiso 1 2 calc R U P . .
C14 C 0.4446(2) 0.20262(13) 0.27028(14) 0.0219(5) Uani 1 1 d . . . . .
H14 H 0.3863 0.1985 0.2298 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4360(2) 0.13518(14) 0.32474(15) 0.0261(6) Uani 1 1 d . . . . .
H15A H 0.3646 0.1353 0.3516 0.031 Uiso 1 1 calc R U . . .
H15B H 0.4943 0.1372 0.3645 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4480(2) 0.06357(14) 0.27449(16) 0.0298(6) Uani 1 1 d . . . . .
H16A H 0.4482 0.0184 0.3088 0.036 Uiso 1 1 calc R U . . .
H16B H 0.3843 0.0595 0.2394 0.036 Uiso 1 1 calc R U . . .
B1 B 0.5000 0.3298(2) 0.2500 0.0239(9) Uani 1 2 d S T P . .
B2 B 0.2636(3) 0.37307(18) 0.49750(18) 0.0293(7) Uani 1 1 d . . . . .
Cl1S Cl 0.35984(9) 0.13063(6) 0.69863(5) 0.0671(3) Uani 1 1 d . . . . .
Cl2S Cl 0.34512(6) 0.15930(5) 0.53271(5) 0.0456(2) Uani 1 1 d . . . . .
C1S C 0.3877(3) 0.09552(19) 0.60555(18) 0.0491(8) Uani 1 1 d . . . . .
H1SA H 0.3498 0.0464 0.5984 0.059 Uiso 1 1 calc R U . . .
H1SB H 0.4669 0.0864 0.6004 0.059 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'
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'
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
C8 N1 C14 124.6(2) . . ?
C8 N1 B1 127.0(2) . . ?
B1 N1 C14 108.1(2) . . ?
C3 N2 C9 107.6(2) . . ?
C3 N2 B2 125.7(2) . . ?
C9 N2 B2 123.5(2) . . ?
C4 N3 C7 107.6(2) . . ?
C4 N3 B2 128.8(2) . . ?
C7 N3 B2 123.5(2) . . ?
C2 C1 H1 126.4 . . ?
C2 C1 C9 107.3(2) . . ?
C9 C1 H1 126.4 . . ?
C1 C2 H2 126.3 . . ?
C3 C2 C1 107.3(2) . . ?
C3 C2 H2 126.3 . . ?
N2 C3 C2 110.0(2) . . ?
N2 C3 H3 125.0 . . ?
C2 C3 H3 125.0 . . ?
N3 C4 H4 125.0 . . ?
N3 C4 C5 110.0(2) . . ?
C5 C4 H4 125.0 . . ?
C4 C5 H5 126.5 . . ?
C6 C5 C4 107.1(2) . . ?
C6 C5 H5 126.5 . . ?
C5 C6 H6 126.3 . . ?
C5 C6 C7 107.5(2) . . ?
C7 C6 H6 126.3 . . ?
N3 C7 C6 107.9(2) . . ?
N3 C7 C8 120.5(2) . . ?
C8 C7 C6 131.4(2) . . ?
N1 C8 C7 117.4(2) . . ?
N1 C8 C9 122.2(2) . . ?
C7 C8 C9 120.4(2) . . ?
N2 C9 C1 107.9(2) . . ?
N2 C9 C8 119.4(2) . . ?
C1 C9 C8 132.7(2) . . ?
C11 C10 C11 117.8(3) . 3_655 ?
C11 C10 B1 121.12(17) . . ?
C11 C10 B1 121.12(17) 3_655 . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C12 120.5(4) . 3_655 ?
C12 C13 H13 119.7 . . ?
C12 C13 H13 119.7 3_655 . ?
N1 C14 C14 100.54(14) . 3_655 ?
N1 C14 H14 108.7 . . ?
N1 C14 C15 119.5(2) . . ?
C14 C14 H14 108.7 3_655 . ?
C15 C14 C14 110.08(18) . 3_655 ?
C15 C14 H14 108.7 . . ?
C14 C15 H15A 110.3 . . ?
C14 C15 H15B 110.3 . . ?
C14 C15 C16 106.9(2) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C16 C16 C15 112.92(18) 3_655 . ?
C16 C16 H16A 109.0 3_655 . ?
C16 C16 H16B 109.0 3_655 . ?
H16A C16 H16B 107.8 . . ?
N1 B1 N1 106.2(3) 3_655 . ?
N1 B1 C10 126.89(15) 3_655 . ?
N1 B1 C10 126.89(15) . . ?
Cl1 B2 Cl2 109.12(16) . . ?
N2 B2 Cl1 112.3(2) . . ?
N2 B2 Cl2 107.23(19) . . ?
N3 B2 Cl1 111.0(2) . . ?
N3 B2 Cl2 109.5(2) . . ?
N3 B2 N2 107.6(2) . . ?
Cl1S C1S Cl2S 111.45(18) . . ?
Cl1S C1S H1SA 109.3 . . ?
Cl1S C1S H1SB 109.3 . . ?
Cl2S C1S H1SA 109.3 . . ?
Cl2S C1S H1SB 109.3 . . ?
H1SA C1S H1SB 108.0 . . ?
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
Cl1 B2 1.833(3) . ?
Cl2 B2 1.893(3) . ?
N1 C8 1.385(3) . ?
N1 C14 1.491(3) . ?
N1 B1 1.435(3) . ?
N2 C3 1.352(3) . ?
N2 C9 1.392(3) . ?
N2 B2 1.520(4) . ?
N3 C4 1.346(3) . ?
N3 C7 1.392(3) . ?
N3 B2 1.519(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(4) . ?
C1 C9 1.401(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.395(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(3) . ?
C7 C8 1.400(4) . ?
C8 C9 1.410(3) . ?
C10 C11 1.398(3) . ?
C10 C11 1.398(3) 3_655 ?
C10 B1 1.563(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(4) . ?
C13 C12 1.378(4) 3_655 ?
C13 H13 0.9500 . ?
C14 C14 1.528(5) 3_655 ?
C14 H14 1.0000 . ?
C14 C15 1.516(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.536(4) . ?
C16 C16 1.528(5) 3_655 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
B1 N1 1.435(3) 3_655 ?
Cl1S C1S 1.748(3) . ?
Cl2S C1S 1.761(3) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
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
N1 C8 C9 N2 -177.6(2) . . . . ?
N1 C8 C9 C1 -0.7(4) . . . . ?
N1 C14 C15 C16 -176.1(2) . . . . ?
N3 C4 C5 C6 -0.1(3) . . . . ?
N3 C7 C8 N1 172.6(2) . . . . ?
N3 C7 C8 C9 -6.6(4) . . . . ?
C1 C2 C3 N2 -0.3(3) . . . . ?
C2 C1 C9 N2 -0.1(3) . . . . ?
C2 C1 C9 C8 -177.3(3) . . . . ?
C3 N2 C9 C1 -0.1(3) . . . . ?
C3 N2 C9 C8 177.5(2) . . . . ?
C3 N2 B2 Cl1 54.1(3) . . . . ?
C3 N2 B2 Cl2 -65.8(3) . . . . ?
C3 N2 B2 N3 176.6(2) . . . . ?
C4 N3 C7 C6 0.5(3) . . . . ?
C4 N3 C7 C8 176.3(2) . . . . ?
C4 N3 B2 Cl1 -39.2(4) . . . . ?
C4 N3 B2 Cl2 81.3(3) . . . . ?
C4 N3 B2 N2 -162.5(2) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 N3 -0.6(3) . . . . ?
C5 C6 C7 C8 -175.7(3) . . . . ?
C6 C7 C8 N1 -12.7(4) . . . . ?
C6 C7 C8 C9 168.1(3) . . . . ?
C7 N3 C4 C5 -0.3(3) . . . . ?
C7 N3 B2 Cl1 144.2(2) . . . . ?
C7 N3 B2 Cl2 -95.3(3) . . . . ?
C7 N3 B2 N2 20.9(3) . . . . ?
C7 C8 C9 N2 1.5(3) . . . . ?
C7 C8 C9 C1 178.5(3) . . . . ?
C8 N1 C14 C14 -152.6(2) . . . 3_655 ?
C8 N1 C14 C15 -32.2(3) . . . . ?
C8 N1 B1 N1 172.9(3) . . . 3_655 ?
C8 N1 B1 C10 -7.1(3) . . . . ?
C9 N2 C3 C2 0.3(3) . . . . ?
C9 N2 B2 Cl1 -148.7(2) . . . . ?
C9 N2 B2 Cl2 91.4(3) . . . . ?
C9 N2 B2 N3 -26.2(3) . . . . ?
C9 C1 C2 C3 0.2(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C10 C11 C12 0.0(2) 3_655 . . . ?
C11 C10 B1 N1 144.57(16) . . . . ?
C11 C10 B1 N1 -35.43(16) . . . 3_655 ?
C11 C10 B1 N1 -35.43(16) 3_655 . . . ?
C11 C10 B1 N1 144.57(16) 3_655 . . 3_655 ?
C11 C12 C13 C12 0.0(2) . . . 3_655 ?
C14 N1 C8 C7 133.5(2) . . . . ?
C14 N1 C8 C9 -47.3(3) . . . . ?
C14 N1 B1 N1 -13.35(12) . . . 3_655 ?
C14 N1 B1 C10 166.65(12) . . . . ?
C14 C14 C15 C16 -60.6(3) 3_655 . . . ?
C14 C15 C16 C16 54.6(3) . . . 3_655 ?
B1 N1 C8 C7 -53.7(3) . . . . ?
B1 N1 C8 C9 125.5(2) . . . . ?
B1 N1 C14 C14 33.5(3) . . . 3_655 ?
B1 N1 C14 C15 153.92(19) . . . . ?
B1 C10 C11 C12 180.0(2) . . . . ?
B2 N2 C3 C2 160.5(2) . . . . ?
B2 N2 C9 C1 -160.8(2) . . . . ?
B2 N2 C9 C8 16.8(4) . . . . ?
B2 N3 C4 C5 -177.3(3) . . . . ?
B2 N3 C7 C6 177.8(2) . . . . ?
B2 N3 C7 C8 -6.5(4) . . . . ?
