#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:41:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/01/7230130.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_7230130
loop_
_publ_author_name
'Filatov, Mikhail A.'
'Karuthedath, Safakath'
'Polestshuk, Pavel M.'
'Callaghan, Susan'
'Flanagan, Keith J.'
'Telitchko, Maxime'
'Wiesner, Thomas'
'Laquai, Frédéric'
'Senge, Mathias O.'
_publ_section_title
;
 Control of triplet state generation in heavy atom-free BODIPY-anthracene
 dyads by media polarity and structural factors.
;
_journal_issue                   12
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              8016
_journal_page_last               8031
_journal_paper_doi               10.1039/c7cp08472b
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C26 H21 B F2 N2'
_chemical_formula_sum            'C26 H21 B F2 N2'
_chemical_formula_weight         410.26
_chemical_name_systematic
3,5-Dimethyl-8-(methylanthracen-9-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-12 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.6700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2460(6)
_cell_length_b                   12.7829(6)
_cell_length_c                   12.8418(6)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.678
_cell_measurement_theta_min      2.324
_cell_volume                     1975.94(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016) '
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30018
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.324
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0501 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.9253. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0395
_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)+(0.0495P)²+2.2286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1954
_reflns_number_total             2272
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cp08472b2.cif
_cod_data_source_block           kjf173
_cod_depositor_comments
'Adding full bibliography for 7230130--7230136.cif.'
_cod_database_code               7230130
_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   0.987
_shelx_estimated_absorpt_t_min   0.973
_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. Others
 Fixed Sof: H23A(0.5) H23B(0.5) H23C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C17(H17), C18(H18), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN micromount with oil'
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F13 F 0.42274(7) -0.07952(6) 0.16592(7) 0.0238(2) Uani 1 1 d . . . . .
N10 N 0.55982(9) 0.05564(8) 0.19641(9) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.62728(11) 0.20198(10) 0.14696(11) 0.0180(3) Uani 1 1 d . . . . .
H1 H 0.6430 0.2731 0.1381 0.022 Uiso 1 1 calc R . . . .
C2 C 0.66518(11) 0.11586(11) 0.10959(11) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.7118 0.1167 0.0699 0.025 Uiso 1 1 calc R . . . .
C3 C 0.62228(11) 0.02606(11) 0.14083(11) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.5000 0.21917(14) 0.2500 0.0143(3) Uani 1 2 d S T P . .
C9 C 0.56062(10) 0.16470(9) 0.20106(10) 0.0153(3) Uani 1 1 d . . . . .
C15 C 0.5000 0.33600(13) 0.2500 0.0144(3) Uani 1 2 d S T P . .
C16 C 0.55671(10) 0.39068(10) 0.35348(10) 0.0145(3) Uani 1 1 d . . . . .
C17 C 0.61877(10) 0.33706(10) 0.45919(11) 0.0171(3) Uani 1 1 d . . . . .
H17 H 0.6244 0.2630 0.4592 0.021 Uiso 1 1 calc R . . . .
C18 C 0.66981(11) 0.39030(11) 0.55944(11) 0.0195(3) Uani 1 1 d . . . . .
H18 H 0.7108 0.3533 0.6285 0.023 Uiso 1 1 calc R . . . .
C19 C 0.66196(11) 0.50120(11) 0.56098(11) 0.0207(3) Uani 1 1 d . . . . .
H19 H 0.6953 0.5378 0.6316 0.025 Uiso 1 1 calc R . . . .
C20 C 0.60714(11) 0.55517(10) 0.46227(11) 0.0183(3) Uani 1 1 d . . . . .
H20 H 0.6041 0.6293 0.4651 0.022 Uiso 1 1 calc R . . . .
C21 C 0.55356(10) 0.50318(10) 0.35364(11) 0.0153(3) Uani 1 1 d . . . . .
C22 C 0.5000 0.55869(14) 0.2500 0.0168(4) Uani 1 2 d S T P . .
C23 C 0.5000 0.67686(15) 0.2500 0.0261(4) Uani 1 2 d S T P . .
H23A H 0.471(4) 0.704(3) 0.307(4) 0.039 Uiso 0.5 1 d R . . A -1
H23B H 0.455(4) 0.707(3) 0.179(4) 0.039 Uiso 0.5 1 d R . . B -1
H23C H 0.578(4) 0.704(3) 0.283(4) 0.039 Uiso 0.5 1 d R . . C -1
C24 C 0.63788(13) -0.08537(11) 0.11667(13) 0.0250(3) Uani 1 1 d . . . . .
H24A H 0.6652 -0.1254 0.1882 0.038 Uiso 1 1 calc GR . . . .
H24B H 0.6919 -0.0895 0.0830 0.038 Uiso 1 1 calc GR . . . .
H24C H 0.5667 -0.1145 0.0629 0.038 Uiso 1 1 calc GR . . . .
B4 B 0.5000 -0.01716(16) 0.2500 0.0171(4) Uani 1 2 d S T P . .
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'
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
C3 N10 C9 107.85(11) . .
C3 N10 B4 127.05(11) . .
C9 N10 B4 125.08(11) . .
C2 C1 H1 126.4 . .
C2 C1 C9 107.15(12) . .
C9 C1 H1 126.4 . .
C1 C2 H2 126.2 . .
C1 C2 C3 107.62(12) . .
C3 C2 H2 126.2 . .
N10 C3 C2 109.28(11) . .
N10 C3 C24 123.06(12) . .
C2 C3 C24 127.65(12) . .
C9 C8 C9 120.12(16) . 2_655
C9 C8 C15 119.94(8) . .
C9 C8 C15 119.94(8) 2_655 .
N10 C9 C1 108.10(11) . .
C8 C9 N10 121.50(12) . .
C8 C9 C1 130.37(12) . .
C16 C15 C8 119.74(8) . .
C16 C15 C8 119.74(8) 2_655 .
C16 C15 C16 120.52(16) 2_655 .
C15 C16 C17 121.66(12) . .
C15 C16 C21 119.52(12) . .
C17 C16 C21 118.81(11) . .
C16 C17 H17 119.4 . .
C18 C17 C16 121.25(12) . .
C18 C17 H17 119.4 . .
C17 C18 H18 120.0 . .
C17 C18 C19 120.10(12) . .
C19 C18 H18 120.0 . .
C18 C19 H19 119.8 . .
C20 C19 C18 120.49(12) . .
C20 C19 H19 119.8 . .
C19 C20 H20 119.1 . .
C19 C20 C21 121.77(12) . .
C21 C20 H20 119.1 . .
C20 C21 C16 117.44(11) . .
C22 C21 C16 120.33(12) . .
C22 C21 C20 122.23(12) . .
C21 C22 C21 119.60(16) 2_655 .
C21 C22 C23 120.20(8) 2_655 .
C21 C22 C23 120.20(8) . .
C22 C23 H23A 110(2) . .
C22 C23 H23B 114(3) . .
C22 C23 H23C 110(2) . .
H23A C23 H23B 107(3) . .
H23A C23 H23C 102(3) . .
H23B C23 H23C 113(3) . .
C3 C24 H24A 109.5 . .
C3 C24 H24B 109.5 . .
C3 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
F13 B4 F13 109.89(15) . 2_655
F13 B4 N10 109.95(5) . 2_655
F13 B4 N10 110.22(5) 2_655 2_655
F13 B4 N10 109.95(5) 2_655 .
F13 B4 N10 110.22(5) . .
N10 B4 N10 106.56(14) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F13 B4 1.3879(14) .
N10 C3 1.3527(17) .
N10 C9 1.3952(16) .
N10 B4 1.5565(16) .
C1 H1 0.9500 .
C1 C2 1.3768(18) .
C1 C9 1.4147(17) .
C2 H2 0.9500 .
C2 C3 1.4113(19) .
C3 C24 1.4904(19) .
C8 C9 1.3950(15) 2_655
C8 C9 1.3950(15) .
C8 C15 1.493(2) .
C15 C16 1.4090(14) 2_655
C15 C16 1.4091(15) .
C16 C17 1.4341(17) .
C16 C21 1.4387(17) .
C17 H17 0.9500 .
C17 C18 1.3605(18) .
C18 H18 0.9500 .
C18 C19 1.4222(19) .
C19 H19 0.9500 .
C19 C20 1.3571(19) .
C20 H20 0.9500 .
C20 C21 1.4371(17) .
C21 C22 1.4106(15) .
C22 C21 1.4106(15) 2_655
C22 C23 1.511(3) .
C23 H23A 1.02(4) .
C23 H23B 0.94(5) .
C23 H23C 1.00(4) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
B4 F13 1.3879(14) 2_655
B4 N10 1.5566(16) 2_655
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_4
C1 C2 C3 N10 -0.21(15) . .
C1 C2 C3 C24 178.42(13) . .
C2 C1 C9 N10 0.46(14) . .
C2 C1 C9 C8 -177.66(11) . .
C3 N10 C9 C1 -0.59(14) . .
C3 N10 C9 C8 177.73(10) . .
C3 N10 B4 F13 60.42(15) . 2_655
C3 N10 B4 F13 -60.88(15) . .
C3 N10 B4 N10 179.86(13) . 2_655
C8 C15 C16 C17 2.54(13) . .
C8 C15 C16 C21 -178.07(8) . .
C9 N10 C3 C2 0.50(14) . .
C9 N10 C3 C24 -178.21(12) . .
C9 N10 B4 F13 -117.45(13) . 2_655
C9 N10 B4 F13 121.26(13) . .
C9 N10 B4 N10 2.00(8) . 2_655
C9 C1 C2 C3 -0.16(15) . .
C9 C8 C9 N10 1.98(8) 2_655 .
C9 C8 C9 C1 179.88(15) 2_655 .
C9 C8 C15 C16 71.05(8) 2_655 .
C9 C8 C15 C16 -108.95(8) . .
C9 C8 C15 C16 71.05(8) . 2_655
C9 C8 C15 C16 -108.95(8) 2_655 2_655
C15 C8 C9 N10 -178.02(8) . .
C15 C8 C9 C1 -0.12(15) . .
C15 C16 C17 C18 -177.51(11) . .
C15 C16 C21 C20 176.43(10) . .
C15 C16 C21 C22 -3.93(16) . .
C16 C15 C16 C17 -177.46(13) 2_655 .
C16 C15 C16 C21 1.93(8) 2_655 .
C16 C17 C18 C19 0.22(19) . .
C16 C21 C22 C21 1.96(8) . 2_655
C16 C21 C22 C23 -178.04(8) . .
C17 C16 C21 C20 -4.17(17) . .
C17 C16 C21 C22 175.48(10) . .
C17 C18 C19 C20 -2.4(2) . .
C18 C19 C20 C21 1.2(2) . .
C19 C20 C21 C16 2.11(18) . .
C19 C20 C21 C22 -177.53(11) . .
C20 C21 C22 C21 -178.42(13) . 2_655
C20 C21 C22 C23 1.59(13) . .
C21 C16 C17 C18 3.10(18) . .
B4 N10 C3 C2 -177.67(9) . .
B4 N10 C3 C24 3.62(19) . .
B4 N10 C9 C1 177.62(9) . .
B4 N10 C9 C8 -4.07(16) . .
