#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:02:40 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179464 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/61/4336144.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_4336144
loop_
_publ_author_name
'Grzegorz Wesela-Bauman'
'Paulina Ciećwierz'
'Krzysztof Durka'
'Sergiusz Luliński'
'Janusz Serwatowski'
'Krzysztof Woźniak'
_publ_contact_author_address
; 
 Crystallochemistry Laboratory 
 Department of Chemistry 
 University of Warsaw 
 Pasteura 1, 02-093 Warszawa, Poland 
 Laboratory of Fine Technologies 
 Department of Chemistry 
 Warsaw University of Technology 
 ul. Noakowskiego 3, 00-664 Warszawa, Poland 
;
_publ_contact_author_email       grzegorz.wesela@chem.uw.edu.pl
_publ_contact_author_name        'Grzegorz Wesela-Bauman'
_publ_section_title
;
 Heteroleptic (2-Fluoro-3-pyridyl)arylborinic 8-Oxyquinolinates for the
 Potential Application in Organic Light-Emitting Devices
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10846
_journal_page_last               10859
_journal_paper_doi               10.1021/ic400729t
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C18 H12 B F N2 O S'
_chemical_formula_weight         334.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.901(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5208(3)
_cell_length_b                   14.3566(4)
_cell_length_c                   12.1658(4)
_cell_measurement_reflns_used    15184
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.6590
_cell_measurement_theta_min      2.7517
_cell_volume                     1563.59(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.7 (release 14-02-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,09:34:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.7 (release 14-02-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,09:34:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.7 (release 14-02-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,09:34:54)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            54028
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.7 (release 14-02-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,09:34:54)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       unspecified
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.439
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.263
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0774
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0693P)²+5.9385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.1997
_reflns_number_gt                2608
_reflns_number_total             3074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400729t_si_004.cif
_cod_data_source_block           gwbpc5
_cod_original_cell_volume        1563.59(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4336144
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.3188(5) 0.0851(3) 0.0872(4) 0.0219(9) Uani 1 1 d . A .
C8 C 0.3339(5) 0.1136(3) 0.2011(4) 0.0211(9) Uani 1 1 d . A .
C7 C 0.2631(5) 0.0624(3) 0.2624(4) 0.0261(10) Uani 1 1 d . . .
H7 H 0.2683 0.0802 0.3389 0.031 Uiso 1 1 calc R . .
C6 C 0.1820(5) -0.0179(3) 0.2077(4) 0.0306(10) Uani 1 1 d . . .
H6 H 0.1332 -0.0537 0.2497 0.037 Uiso 1 1 calc R . .
C2 C 0.3058(6) 0.0541(4) -0.1342(4) 0.0358(12) Uani 1 1 d . . .
H2 H 0.3026 0.0441 -0.2122 0.043 Uiso 1 1 calc R . .
C1 C 0.3810(6) 0.1324(3) -0.0726(4) 0.0310(11) Uani 1 1 d . A .
H1 H 0.4276 0.1750 -0.1092 0.037 Uiso 1 1 calc R . .
C4 C 0.2391(5) 0.0064(3) 0.0314(4) 0.0246(9) Uani 1 1 d . . .
C3 C 0.2368(6) -0.0082(3) -0.0838(4) 0.0321(11) Uani 1 1 d . . .
H3 H 0.1875 -0.0611 -0.1265 0.039 Uiso 1 1 calc R . .
C5 C 0.1704(5) -0.0466(3) 0.0972(4) 0.0294(10) Uani 1 1 d . . .
H5 H 0.1166 -0.1016 0.0652 0.035 Uiso 1 1 calc R . .
C15 C 0.3690(5) 0.3262(3) 0.0883(3) 0.0210(9) Uani 1 1 d . . .
C14 C 0.2094(5) 0.3361(3) 0.0437(4) 0.0268(10) Uani 1 1 d . . .
C16 C 0.4399(5) 0.4127(3) 0.1040(4) 0.0215(9) Uani 1 1 d . . .
H16 H 0.5458 0.4161 0.1333 0.026 Uiso 1 1 calc R . .
C17 C 0.3556(5) 0.4942(3) 0.0767(4) 0.0237(9) Uani 1 1 d . . .
H17 H 0.4031 0.5533 0.0880 0.028 Uiso 1 1 calc R . .
C18 C 0.2031(5) 0.4873(3) 0.0335(4) 0.0257(10) Uani 1 1 d . . .
H18 H 0.1455 0.5429 0.0154 0.031 Uiso 1 1 calc R . .
C10 C 0.6280(3) 0.2340(3) 0.1593(2) 0.0237(8) Uani 1 1 d D . .
N1 N 0.3870(4) 0.1468(2) 0.0366(3) 0.0230(8) Uani 1 1 d . . .
N2 N 0.1318(5) 0.4046(3) 0.0156(4) 0.0347(10) Uani 1 1 d . . .
O1 O 0.4180(3) 0.1914(2) 0.2336(2) 0.0229(7) Uani 1 1 d . . .
B1 B 0.4564(6) 0.2292(3) 0.1307(4) 0.0220(10) Uani 1 1 d . A .
F1 F 0.1356(3) 0.2508(2) 0.0237(3) 0.0392(7) Uani 1 1 d . . .
S1A S 0.76496(16) 0.2029(2) 0.28680(14) 0.0309(4) Uani 0.848(4) 1 d PD A 1
C11A C 0.7061(5) 0.2619(5) 0.0767(5) 0.0237(8) Uani 0.848(4) 1 d PD A 1
H11A H 0.6547 0.2784 -0.0025 0.028 Uiso 0.848(4) 1 calc PR A 1
C12A C 0.8578(6) 0.2615(4) 0.1255(4) 0.0297(13) Uani 0.848(4) 1 d PD A 1
H12A H 0.9215 0.2813 0.0845 0.036 Uiso 0.848(4) 1 calc PR A 1
C13A C 0.9132(3) 0.2288(4) 0.2429(4) 0.0311(14) Uani 0.848(4) 1 d PD A 1
H13A H 1.0156 0.2224 0.2892 0.037 Uiso 0.848(4) 1 calc PR A 1
S1B S 0.7204(11) 0.2746(9) 0.0706(8) 0.0309(4) Uani 0.152(4) 1 d PD A 2
C13B C 0.891(2) 0.249(3) 0.172(2) 0.0311(14) Uani 0.152(4) 1 d PD A 2
H13B H 0.9842 0.2584 0.1599 0.037 Uiso 0.152(4) 1 calc PR A 2
C12B C 0.876(3) 0.212(2) 0.275(3) 0.0297(13) Uani 0.152(4) 1 d PD A 2
H12B H 0.9596 0.1928 0.3397 0.036 Uiso 0.152(4) 1 calc PR A 2
C11B C 0.732(2) 0.206(5) 0.278(2) 0.0237(8) Uani 0.152(4) 1 d PD A 2
H11B H 0.7037 0.1870 0.3422 0.028 Uiso 0.152(4) 1 calc PR A 2
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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C9 C4 124.6(4)
N1 C9 C8 110.6(4)
C4 C9 C8 124.7(4)
O1 C8 C7 129.2(4)
O1 C8 C9 112.4(3)
C7 C8 C9 118.4(4)
C8 C7 C6 117.9(4)
C5 C6 C7 123.5(4)
C3 C2 C1 121.2(4)
N1 C1 C2 120.0(4)
C9 C4 C3 115.1(4)
C9 C4 C5 116.0(4)
C3 C4 C5 129.0(4)
C2 C3 C4 120.0(4)
C6 C5 C4 119.6(4)
C16 C15 C14 111.4(4)
C16 C15 B1 123.5(4)
C14 C15 B1 124.8(4)
N2 C14 F1 116.3(4)
N2 C14 C15 130.9(4)
F1 C14 C15 112.7(4)
C17 C16 C15 120.1(4)
C18 C17 C16 118.8(4)
N2 C18 C17 122.3(4)
C11A C10 C11B 113.8(9)
C11A C10 B1 126.0(3)
C11B C10 B1 120.2(9)
C11A C10 S1B 4.7(7)
C11B C10 S1B 112.7(10)
B1 C10 S1B 127.0(4)
C11A C10 S1A 106.2(3)
C11B C10 S1A 7.6(9)
B1 C10 S1A 127.7(3)
S1B C10 S1A 105.3(4)
C1 N1 C9 119.1(4)
C1 N1 B1 133.5(4)
C9 N1 B1 107.3(3)
C14 N2 C18 116.5(4)
C8 O1 B1 109.8(3)
O1 B1 C10 111.2(3)
O1 B1 C15 109.2(3)
C10 B1 C15 115.0(4)
O1 B1 N1 99.6(3)
C10 B1 N1 109.6(3)
C15 B1 N1 111.2(3)
C10 S1A C13A 96.64(19)
C12A C11A C10 113.7(4)
C11A C12A C13A 114.5(4)
C12A C13A S1A 108.8(3)
C10 S1B C13B 92.5(12)
C12B C13B S1B 111(2)
C11B C12B C13B 117(2)
C12B C11B C10 107.3(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 N1 1.363(5)
C9 C4 1.400(6)
C9 C8 1.404(6)
C8 O1 1.353(5)
C8 C7 1.376(6)
C7 C6 1.421(7)
C6 C5 1.373(7)
C2 C3 1.371(7)
C2 C1 1.405(7)
C1 N1 1.327(6)
C4 C3 1.411(6)
C4 C5 1.415(6)
C15 C16 1.395(6)
C15 C14 1.436(6)
C15 B1 1.615(6)
C14 N2 1.207(6)
C14 F1 1.392(5)
C16 C17 1.392(6)
C17 C18 1.370(6)
C18 N2 1.349(6)
C10 C11A 1.4949(12)
C10 C11B 1.4969(12)
C10 B1 1.551(6)
C10 S1B 1.7106(12)
C10 S1A 1.7111(12)
N1 B1 1.622(6)
O1 B1 1.520(5)
S1A C13A 1.7117(12)
C11A C12A 1.3624(12)
C12A C13A 1.4233(12)
S1B C13B 1.7120(12)
C13B C12B 1.4240(12)
C12B C11B 1.3840(8)
