#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513279.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1513279
loop_
_publ_author_name
'Tokoro, Yuichiro'
'Nagai, Atsushi'
'Kokado, Kenta'
'Chujo, Yoshiki'
_publ_section_title
;
 Synthesis of Organoboron Quinoline-8-thiolate and Quinoline-8-selenolate
 Complexes and Their Incorporation into the π-Conjugated Polymer
 Main-Chain
;
_journal_issue                   8
_journal_name_full               Macromolecules
_journal_page_first              2988
_journal_paper_doi               10.1021/ma900008m
_journal_volume                  42
_journal_year                    2009
_chemical_formula_sum            'C21 H16 B N S'
_chemical_formula_weight         325.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.080(2)
_cell_length_b                   15.806(4)
_cell_length_c                   17.537(5)
_cell_measurement_temperature    93(2)
_cell_volume                     3348.5(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.2224
_diffrn_reflns_av_sigmaI/netI    0.1606
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30702
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.2047
_refine_ls_R_factor_gt           0.0892
_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)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                2047
_reflns_number_total             3837
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ma900008msup2.cif
_cod_data_source_block           5
_cod_original_cell_volume        3348.5(15)
_cod_original_sg_symbol_Hall     -p_2ac_2ab
_cod_original_sg_symbol_H-M      p_b_c_a
_cod_database_code               1513279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
S1 S 0.25976(8) 0.07473(7) 0.34962(6) 0.0306(3) Uani 1 1 d .
N1 N 0.4784(2) 0.10987(19) 0.32552(16) 0.0158(7) Uani 1 1 d .
C2 C 0.4286(3) 0.1825(2) 0.3501(2) 0.0198(8) Uani 1 1 d .
C11 C 0.3841(3) 0.0250(2) 0.2147(2) 0.0159(8) Uani 1 1 d .
C17 C 0.4467(3) -0.0517(2) 0.3459(2) 0.0195(9) Uani 1 1 d .
C3 C 0.5872(3) 0.1084(2) 0.3161(2) 0.0219(9) Uani 1 1 d .
H1 H 0.6212 0.0577 0.2988 0.026 Uiso 1 1 calc R
C4 C 0.6050(3) 0.2520(3) 0.3535(2) 0.0281(10) Uani 1 1 d .
H2 H 0.6496 0.3005 0.3626 0.034 Uiso 1 1 calc R
C12 C 0.3036(3) -0.0294(2) 0.1850(2) 0.0216(9) Uani 1 1 d .
H3 H 0.2611 -0.0623 0.2196 0.026 Uiso 1 1 calc R
C13 C 0.4453(3) 0.0704(2) 0.1612(2) 0.0206(9) Uani 1 1 d .
H4 H 0.5009 0.1083 0.1785 0.025 Uiso 1 1 calc R
C5 C 0.3128(3) 0.1770(3) 0.3627(2) 0.0255(10) Uani 1 1 d .
C6 C 0.6535(3) 0.1786(3) 0.3307(2) 0.0259(10) Uani 1 1 d .
H5 H 0.7315 0.1753 0.3249 0.031 Uiso 1 1 calc R
C14 C 0.4275(3) 0.0620(3) 0.0834(2) 0.0296(10) Uani 1 1 d .
H6 H 0.4717 0.0932 0.0486 0.036 Uiso 1 1 calc R
B1 B 0.3999(3) 0.0319(3) 0.3055(3) 0.0198(10) Uani 1 1 d .
C18 C 0.5017(3) -0.1140(2) 0.3056(2) 0.0250(10) Uani 1 1 d .
H7 H 0.5070 -0.1089 0.2517 0.030 Uiso 1 1 calc R
C15 C 0.2830(3) -0.0374(2) 0.1077(2) 0.0246(10) Uani 1 1 d .
H8 H 0.2264 -0.0742 0.0900 0.029 Uiso 1 1 calc R
C7 C 0.4896(3) 0.2572(2) 0.3636(2) 0.0226(9) Uani 1 1 d .
C19 C 0.5495(3) -0.1837(3) 0.3408(3) 0.0326(10) Uani 1 1 d .
H9 H 0.5872 -0.2250 0.3112 0.039 Uiso 1 1 calc R
C8 C 0.4305(4) 0.3292(3) 0.3877(2) 0.0346(11) Uani 1 1 d .
H10 H 0.4681 0.3809 0.3974 0.042 Uiso 1 1 calc R
C9 C 0.2586(4) 0.2484(3) 0.3853(2) 0.0427(12) Uani 1 1 d .
H11 H 0.1808 0.2474 0.3931 0.051 Uiso 1 1 calc R
C16 C 0.3459(3) 0.0087(2) 0.0564(2) 0.0272(10) Uani 1 1 d .
H12 H 0.3331 0.0037 0.0031 0.033 Uiso 1 1 calc R
C10 C 0.3186(4) 0.3237(3) 0.3971(2) 0.0439(13) Uani 1 1 d .
H13 H 0.2793 0.3730 0.4122 0.053 Uiso 1 1 calc R
C20 C 0.4400(3) -0.0627(3) 0.4250(2) 0.0273(10) Uani 1 1 d .
H14 H 0.4024 -0.0217 0.4549 0.033 Uiso 1 1 calc R
C21 C 0.5422(4) -0.1928(3) 0.4183(3) 0.0372(12) Uani 1 1 d .
H15 H 0.5746 -0.2404 0.4427 0.045 Uiso 1 1 calc R
C22 C 0.4873(3) -0.1324(3) 0.4607(3) 0.0357(12) Uani 1 1 d .
H16 H 0.4819 -0.1384 0.5144 0.043 Uiso 1 1 calc R
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
C5 S1 B1 93.09(18)
C3 N1 C2 119.5(3)
C3 N1 B1 123.3(3)
C2 N1 B1 117.1(3)
N1 C2 C7 121.7(3)
N1 C2 C5 115.7(3)
C7 C2 C5 122.6(4)
C13 C11 C12 115.7(3)
C13 C11 B1 124.7(3)
C12 C11 B1 119.5(3)
C18 C17 C20 116.5(4)
C18 C17 B1 122.0(4)
C20 C17 B1 121.4(4)
N1 C3 C6 122.2(4)
C6 C4 C7 120.9(4)
C15 C12 C11 123.1(4)
C14 C13 C11 122.1(4)
C9 C5 C2 117.9(4)
C9 C5 S1 128.7(3)
C2 C5 S1 113.3(3)
C4 C6 C3 119.1(3)
C16 C14 C13 120.5(4)
N1 B1 C17 109.3(3)
N1 B1 C11 109.9(3)
C17 B1 C11 115.1(3)
N1 B1 S1 99.1(2)
C17 B1 S1 114.3(3)
C11 B1 S1 108.0(3)
C17 C18 C19 122.5(4)
C16 C15 C12 119.3(4)
C4 C7 C8 125.9(4)
C4 C7 C2 116.6(3)
C8 C7 C2 117.5(3)
C21 C19 C18 119.9(4)
C10 C8 C7 119.1(4)
C5 C9 C10 119.7(4)
C14 C16 C15 119.3(4)
C8 C10 C9 123.1(4)
C22 C20 C17 121.4(4)
C19 C21 C22 119.5(4)
C21 C22 C20 120.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.754(4)
S1 B1 1.980(4)
N1 C3 1.325(4)
N1 C2 1.366(4)
N1 B1 1.594(5)
C2 C7 1.413(5)
C2 C5 1.418(5)
C11 C13 1.394(5)
C11 C12 1.398(5)
C11 B1 1.608(6)
C17 C18 1.383(5)
C17 C20 1.400(5)
C17 B1 1.602(6)
C3 C6 1.392(5)
C4 C6 1.360(5)
C4 C7 1.407(5)
C12 C15 1.385(5)
C13 C14 1.386(5)
C5 C9 1.364(5)
C14 C16 1.381(5)
C18 C19 1.389(5)
C15 C16 1.384(5)
C7 C8 1.409(5)
C19 C21 1.371(6)
C8 C10 1.365(6)
C9 C10 1.409(6)
C20 C22 1.389(5)
C21 C22 1.380(6)
