#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513278.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_1513278
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 Se'
_chemical_formula_weight         372.12
_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                   12.149(2)
_cell_length_b                   15.807(3)
_cell_length_c                   17.735(3)
_cell_measurement_temperature    93(2)
_cell_volume                     3405.8(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.2567
_diffrn_reflns_av_sigmaI/netI    0.2355
_diffrn_reflns_limit_h_max       15
_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            29373
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_T_max  0.8096
_exptl_absorpt_correction_T_min  0.5575
_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    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.308
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.2296
_refine_ls_R_factor_gt           0.0654
_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)+(0.0090P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                1574
_reflns_number_total             3863
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ma900008msup1.cif
_cod_data_source_block           2
_cod_original_cell_volume        3405.9(10)
_cod_original_sg_symbol_Hall     -p_2ac_2ab
_cod_original_sg_symbol_H-M      p_b_c_a
_cod_database_code               1513278
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
Se1 Se 0.75237(7) 0.07451(4) 0.64624(3) 0.02159(13) Uani 1 1 d .
N1 N 0.5254(3) 0.1100(3) 0.6717(2) 0.0099(12) Uani 1 1 d .
C16 C 0.6885(4) 0.1827(4) 0.6359(3) 0.0169(13) Uani 1 1 d .
C17 C 0.5101(4) 0.2578(4) 0.6356(3) 0.0161(14) Uani 1 1 d .
C18 C 0.7357(5) 0.2573(4) 0.6145(3) 0.0262(15) Uani 1 1 d .
H11 H 0.8128 0.2584 0.6057 0.031 Uiso 1 1 calc R
C19 C 0.6532(4) 0.0093(4) 0.9397(3) 0.0216(17) Uani 1 1 d .
H2 H 0.6650 0.0044 0.9925 0.026 Uiso 1 1 calc R
C20 C 0.6169(4) 0.0258(4) 0.7831(3) 0.0106(14) Uani 1 1 d .
C21 C 0.5005(4) -0.1144(4) 0.6931(3) 0.0193(16) Uani 1 1 d .
H3 H 0.4963 -0.1090 0.7464 0.023 Uiso 1 1 calc R
C22 C 0.4508(4) -0.1846(4) 0.6594(3) 0.0261(15) Uani 1 1 d .
H4 H 0.4139 -0.2258 0.6892 0.031 Uiso 1 1 calc R
C23 C 0.6960(4) -0.0301(4) 0.8126(3) 0.0186(16) Uani 1 1 d .
H5 H 0.7375 -0.0638 0.7785 0.022 Uiso 1 1 calc R
C24 C 0.4161(4) 0.1066(4) 0.6807(3) 0.0148(16) Uani 1 1 d .
H12 H 0.3839 0.0550 0.6972 0.018 Uiso 1 1 calc R
B1 B 0.6026(5) 0.0311(5) 0.6936(4) 0.0192(17) Uani 1 1 d .
C26 C 0.3933(4) 0.2508(4) 0.6458(3) 0.0232(15) Uani 1 1 d .
H13 H 0.3474 0.2986 0.6377 0.028 Uiso 1 1 calc R
C27 C 0.5569(4) 0.0725(4) 0.8360(3) 0.0156(15) Uani 1 1 d .
H1 H 0.5032 0.1115 0.8185 0.019 Uiso 1 1 calc R
C28 C 0.5724(4) 0.1835(4) 0.6486(3) 0.0152(12) Uani 1 1 d .
C30 C 0.5558(4) -0.0522(3) 0.6531(3) 0.0110(14) Uani 1 1 d .
C31 C 0.5592(4) -0.0633(4) 0.5746(3) 0.0211(15) Uani 1 1 d .
H6 H 0.5961 -0.0227 0.5443 0.025 Uiso 1 1 calc R
C32 C 0.5643(4) 0.3325(4) 0.6131(3) 0.0243(15) Uani 1 1 d .
H14 H 0.5234 0.3827 0.6038 0.029 Uiso 1 1 calc R
C33 C 0.4563(4) -0.1927(4) 0.5825(3) 0.0274(18) Uani 1 1 d .
H7 H 0.4232 -0.2400 0.5585 0.033 Uiso 1 1 calc R
C34 C 0.3482(4) 0.1752(5) 0.6671(2) 0.0208(15) Uani 1 1 d .
H15 H 0.2707 0.1698 0.6724 0.025 Uiso 1 1 calc R
C35 C 0.5097(4) -0.1327(4) 0.5402(3) 0.0266(18) Uani 1 1 d .
H8 H 0.5129 -0.1385 0.4870 0.032 Uiso 1 1 calc R
C36 C 0.6759(5) 0.3324(5) 0.6049(3) 0.0282(16) Uani 1 1 d .
H16 H 0.7133 0.3833 0.5925 0.034 Uiso 1 1 calc R
C38 C 0.5728(4) 0.0643(4) 0.9119(3) 0.0203(16) Uani 1 1 d .
H9 H 0.5288 0.0960 0.9459 0.024 Uiso 1 1 calc R
C39 C 0.7159(4) -0.0380(3) 0.8893(3) 0.0194(16) Uani 1 1 d .
H10 H 0.7716 -0.0752 0.9072 0.023 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'
Se Se -0.0929 2.2259 '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
C16 Se1 B1 88.8(2)
C24 N1 C28 119.2(5)
C24 N1 B1 121.2(5)
C28 N1 B1 119.4(4)
C18 C16 C28 116.8(6)
C18 C16 Se1 129.6(4)
C28 C16 Se1 113.5(5)
C32 C17 C28 119.4(5)
C32 C17 C26 124.2(6)
C28 C17 C26 116.3(5)
C16 C18 C36 123.2(5)
C39 C19 C38 119.3(5)
C27 C20 C23 116.0(5)
C27 C20 B1 125.6(5)
C23 C20 B1 118.4(5)
C30 C21 C22 123.6(5)
C33 C22 C21 118.5(6)
C39 C23 C20 122.7(6)
N1 C24 C34 122.6(6)
C20 B1 C30 116.1(5)
C20 B1 N1 110.1(5)
C30 B1 N1 108.7(4)
C20 B1 Se1 108.5(4)
C30 B1 Se1 113.1(4)
N1 B1 Se1 98.9(4)
C34 C26 C17 119.9(5)
C38 C27 C20 122.5(6)
N1 C28 C17 122.3(4)
N1 C28 C16 117.1(6)
C17 C28 C16 120.6(6)
C21 C30 C31 115.7(5)
C21 C30 B1 121.6(5)
C31 C30 B1 122.5(5)
C35 C31 C30 121.4(5)
C36 C32 C17 119.6(6)
C35 C33 C22 120.2(6)
C26 C34 C24 119.6(5)
C33 C35 C31 120.6(5)
C32 C36 C18 120.2(6)
C27 C38 C19 120.5(6)
C23 C39 C19 119.0(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C16 1.887(6)
Se1 B1 2.119(6)
N1 C24 1.338(6)
N1 C28 1.358(7)
N1 B1 1.608(8)
C16 C18 1.364(7)
C16 C28 1.429(6)
C17 C32 1.409(8)
C17 C28 1.416(7)
C17 C26 1.434(6)
C18 C36 1.402(8)
C19 C39 1.393(6)
C19 C38 1.397(7)
C20 C27 1.399(7)
C20 C23 1.406(7)
C20 B1 1.599(7)
C21 C30 1.386(6)
C21 C22 1.398(7)
C22 C33 1.372(6)
C23 C39 1.389(6)
C24 C34 1.384(7)
B1 C30 1.604(8)
C26 C34 1.369(8)
C27 C38 1.365(6)
C30 C31 1.403(6)
C31 C35 1.390(7)
C32 C36 1.364(6)
C33 C35 1.372(7)
