#------------------------------------------------------------------------------
#$Date: 2019-11-17 12:16:10 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229821 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/62/7046223.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_7046223
loop_
_publ_author_name
'Stanoppi, Marco'
'Lorbach, Andreas'
_publ_section_title
;
 Boron-based donor-spiro-acceptor compounds exhibiting thermally activated
 delayed fluorescence (TADF).
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10394
_journal_page_last               10398
_journal_paper_doi               10.1039/c8dt01255e
_journal_volume                  47
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H16 B N S'
_chemical_formula_sum            'C23 H16 B N S'
_chemical_formula_weight         349.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-16 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.428(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6076(3)
_cell_length_b                   9.4500(5)
_cell_length_c                   10.8046(4)
_cell_measurement_reflns_used    20114
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.70
_cell_measurement_theta_min      2.16
_cell_volume                     866.99(6)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14213
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.269
_diffrn_reflns_theta_min         2.399
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.03509
_exptl_absorpt_correction_T_min  0.89452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'MULABS / PLATON Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Spek, A.L. (2009). Acta Cryst. D65, 148-155.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.275
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0275
_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)+(0.0454P)²+0.0456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4852
_reflns_number_total             5160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01255e3.cif
_cod_data_source_block           AL43
_cod_depositor_comments
'Adding full bibliography for 7046223--7046226.cif.'
_cod_database_code               7046223
_shelxl_version_number           2013-4
_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   0.949
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_exptl_crystal_mounting_method
'Mounted on MiTeGen Dual-Thickness MicroMounts in paraffin oil.'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
S1 S 0.59921(4) 0.41481(4) 0.93710(4) 0.01969(9) Uani 1 1 d .
N1 N 0.64506(16) 0.83903(15) 0.71836(12) 0.0187(3) Uani 1 1 d .
C1 C 0.71754(18) 0.60550(18) 0.65618(14) 0.0179(3) Uani 1 1 d .
C2 C 0.7643(2) 0.46710(19) 0.63741(15) 0.0205(3) Uani 1 1 d .
H2 H 0.7496 0.3955 0.6961 0.025 Uiso 1 1 calc R
C3 C 0.8327(2) 0.4331(2) 0.53288(15) 0.0249(4) Uani 1 1 d .
H3 H 0.8657 0.3387 0.5216 0.030 Uiso 1 1 calc R
C4 C 0.8532(2) 0.5364(2) 0.44456(16) 0.0279(4) Uani 1 1 d .
H4 H 0.8996 0.5115 0.3736 0.033 Uiso 1 1 calc R
C5 C 0.8064(2) 0.6747(2) 0.45941(16) 0.0255(3) Uani 1 1 d .
H5 H 0.8186 0.7451 0.3990 0.031 Uiso 1 1 calc R
C6 C 0.74070(18) 0.70766(18) 0.56600(14) 0.0196(3) Uani 1 1 d .
C7 C 0.69051(19) 0.84654(18) 0.60346(15) 0.0204(3) Uani 1 1 d .
C8 C 0.6830(2) 0.9750(2) 0.53945(17) 0.0259(3) Uani 1 1 d .
H8 H 0.7145 0.9810 0.4593 0.031 Uiso 1 1 calc R
C9 C 0.6292(2) 1.0935(2) 0.59417(18) 0.0285(4) Uani 1 1 d .
H9 H 0.6216 1.1815 0.5511 0.034 Uiso 1 1 calc R
C10 C 0.5861(2) 1.08368(19) 0.71277(18) 0.0268(3) Uani 1 1 d .
H10 H 0.5512 1.1651 0.7519 0.032 Uiso 1 1 calc R
C11 C 0.5949(2) 0.95417(18) 0.77248(16) 0.0226(3) Uani 1 1 d .
H11 H 0.5650 0.9465 0.8530 0.027 Uiso 1 1 calc R
C12 C 0.76247(18) 0.66201(16) 0.90186(14) 0.0165(3) Uani 1 1 d .
C13 C 0.74463(18) 0.54679(17) 0.98013(14) 0.0174(3) Uani 1 1 d .
C14 C 0.84527(19) 0.52550(18) 1.09380(14) 0.0210(3) Uani 1 1 d .
H14 H 0.8280 0.4486 1.1465 0.025 Uiso 1 1 calc R
C15 C 0.9707(2) 0.61730(19) 1.12948(16) 0.0226(3) Uani 1 1 d .
H15 H 1.0402 0.6028 1.2063 0.027 Uiso 1 1 calc R
C16 C 0.99393(19) 0.73017(18) 1.05263(16) 0.0219(3) Uani 1 1 d .
H16 H 1.0808 0.7921 1.0756 0.026 Uiso 1 1 calc R
C17 C 0.88956(19) 0.75237(17) 0.94173(15) 0.0192(3) Uani 1 1 d .
H17 H 0.9051 0.8318 0.8912 0.023 Uiso 1 1 calc R
C18 C 0.46862(18) 0.63253(16) 0.77988(14) 0.0167(3) Uani 1 1 d .
C19 C 0.44240(19) 0.51214(18) 0.84894(14) 0.0184(3) Uani 1 1 d .
C20 C 0.2915(2) 0.4602(2) 0.85386(16) 0.0228(3) Uani 1 1 d .
H20 H 0.2782 0.3762 0.8992 0.027 Uiso 1 1 calc R
C21 C 0.1610(2) 0.5324(2) 0.79193(16) 0.0258(3) Uani 1 1 d .
H21 H 0.0579 0.4980 0.7945 0.031 Uiso 1 1 calc R
C22 C 0.1821(2) 0.65544(19) 0.72606(16) 0.0234(3) Uani 1 1 d .
H22 H 0.0933 0.7065 0.6849 0.028 Uiso 1 1 calc R
C23 C 0.33364(19) 0.70350(18) 0.72061(14) 0.0192(3) Uani 1 1 d .
H23 H 0.3461 0.7876 0.6750 0.023 Uiso 1 1 calc R
B1 B 0.6465(2) 0.67955(19) 0.76973(16) 0.0168(3) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C13 S1 C19 102.60(8)
C7 N1 B1 112.12(13)
C11 N1 C7 121.08(14)
C11 N1 B1 126.61(13)
C2 C1 C6 117.75(14)
C2 C1 B1 132.15(14)
C6 C1 B1 110.01(14)
C1 C2 C3 120.32(16)
C2 C3 C4 120.67(17)
C5 C4 C3 120.59(16)
C4 C5 C6 118.06(17)
C1 C6 C7 110.03(14)
C5 C6 C1 122.59(16)
C5 C6 C7 127.36(16)
N1 C7 C6 110.36(14)
N1 C7 C8 120.04(16)
C8 C7 C6 129.60(15)
C9 C8 C7 119.03(16)
C8 C9 C10 119.88(17)
C11 C10 C9 119.08(17)
N1 C11 C10 120.88(16)
C13 C12 B1 120.07(14)
C17 C12 C13 116.46(14)
C17 C12 B1 123.35(14)
C12 C13 S1 122.01(12)
C14 C13 S1 116.01(12)
C14 C13 C12 121.91(15)
C15 C14 C13 119.73(15)
C16 C15 C14 119.74(15)
C15 C16 C17 119.73(15)
C16 C17 C12 122.37(15)
C19 C18 C23 116.02(14)
C19 C18 B1 119.83(13)
C23 C18 B1 124.14(14)
C18 C19 S1 122.17(12)
C20 C19 S1 115.30(13)
C20 C19 C18 122.53(15)
C21 C20 C19 119.51(16)
C20 C21 C22 119.65(16)
C21 C22 C23 119.74(16)
C22 C23 C18 122.47(16)
N1 B1 C1 97.27(12)
N1 B1 C12 111.82(13)
N1 B1 C18 109.14(13)
C12 B1 C1 111.82(13)
C12 B1 C18 111.60(12)
C18 B1 C1 114.39(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C13 1.7742(16)
S1 C19 1.7760(17)
N1 C7 1.363(2)
N1 C11 1.340(2)
N1 B1 1.605(2)
C1 C2 1.393(2)
C1 C6 1.409(2)
C1 B1 1.617(2)
C2 C3 1.394(2)
C3 C4 1.396(3)
C4 C5 1.384(3)
C5 C6 1.399(2)
C6 C7 1.459(2)
C7 C8 1.393(2)
C8 C9 1.381(3)
C9 C10 1.394(3)
C10 C11 1.380(2)
C12 C13 1.402(2)
C12 C17 1.399(2)
C12 B1 1.611(2)
C13 C14 1.397(2)
C14 C15 1.389(2)
C15 C16 1.386(2)
C16 C17 1.391(2)
C18 C19 1.399(2)
C18 C23 1.402(2)
C18 B1 1.616(2)
C19 C20 1.398(2)
C20 C21 1.388(3)
C21 C22 1.390(3)
C22 C23 1.392(2)
