#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:40:34 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179122 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/84/4308476.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_4308476
loop_
_publ_author_name
'Yi Cui'
'Qin-De Liu'
'Dong-Ren Bai'
'Wen-Li Jia'
'Ye Tao'
'Suning Wang'
_publ_section_title
;
Organoboron Compounds with an 8-Hydroxyquinolato Chelate and Its
Derivatives: Substituent Effects on Structures and Luminescence
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              601
_journal_page_last               609
_journal_paper_doi               10.1021/ic0489746
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C31 H22 B N O'
_chemical_formula_weight         435.31
_chemical_name_systematic
; 
 ? 
;
_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                 107.837(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.850(5)
_cell_length_b                   7.776(2)
_cell_length_c                   18.372(6)
_cell_measurement_temperature    293(2)
_cell_volume                     2291.5(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.908
_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  0.1483
_diffrn_reflns_av_sigmaI/netI    0.3690
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14684
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0015(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.707
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.707
_refine_ls_R_factor_all          0.3101
_refine_ls_R_factor_gt           0.0711
_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)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1630
_reflns_number_gt                1180
_reflns_number_total             5222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0489746si20040728_035901.cif
_cod_data_source_block           cui1
_cod_original_cell_volume        2291.6(12)
_cod_database_code               4308476
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
O1 O 0.19681(17) 0.2056(3) 0.40222(16) 0.0541(9) Uani 1 1 d . . .
N1 N 0.1787(2) 0.4895(4) 0.44508(18) 0.0433(10) Uani 1 1 d . . .
C1 C 0.0456(3) 0.3140(5) 0.3733(3) 0.0509(13) Uani 1 1 d . . .
B1 B 0.1345(3) 0.2986(6) 0.4344(3) 0.0447(14) Uani 1 1 d . . .
C2 C -0.0193(3) 0.4111(6) 0.3846(3) 0.0581(14) Uani 1 1 d . . .
H2A H -0.0099 0.4682 0.4310 0.070 Uiso 1 1 calc R . .
C4 C -0.1127(3) 0.3451(7) 0.2617(3) 0.0728(16) Uani 1 1 d . . .
H4A H -0.1645 0.3555 0.2248 0.087 Uiso 1 1 calc R . .
C3 C -0.0960(3) 0.4269(6) 0.3313(3) 0.0665(15) Uani 1 1 d . . .
H3A H -0.1370 0.4930 0.3421 0.080 Uiso 1 1 calc R . .
C5 C -0.0509(4) 0.2482(7) 0.2486(3) 0.0770(17) Uani 1 1 d . . .
H5A H -0.0611 0.1914 0.2021 0.092 Uiso 1 1 calc R . .
C6 C 0.0265(3) 0.2328(5) 0.3029(3) 0.0615(15) Uani 1 1 d . . .
H6A H 0.0670 0.1657 0.2919 0.074 Uiso 1 1 calc R . .
C7 C 0.1419(3) 0.2229(5) 0.5176(3) 0.0427(12) Uani 1 1 d . . .
C8 C 0.2188(3) 0.2119(6) 0.5729(3) 0.0685(15) Uani 1 1 d . . .
H8A H 0.2652 0.2517 0.5607 0.082 Uiso 1 1 calc R . .
C9 C 0.2306(4) 0.1455(6) 0.6450(3) 0.0792(17) Uani 1 1 d . . .
H9A H 0.2837 0.1394 0.6801 0.095 Uiso 1 1 calc R . .
C12 C 0.0750(3) 0.1626(5) 0.5392(3) 0.0564(14) Uani 1 1 d . . .
H12A H 0.0218 0.1683 0.5043 0.068 Uiso 1 1 calc R . .
C10 C 0.1620(4) 0.0885(6) 0.6640(3) 0.0830(19) Uani 1 1 d . . .
H10A H 0.1686 0.0462 0.7129 0.100 Uiso 1 1 calc R . .
C11 C 0.0847(4) 0.0935(6) 0.6117(3) 0.0728(17) Uani 1 1 d . . .
H11A H 0.0388 0.0513 0.6241 0.087 Uiso 1 1 calc R . .
C13 C 0.2525(3) 0.3155(5) 0.3905(2) 0.0443(12) Uani 1 1 d . . .
C14 C 0.3136(3) 0.2852(5) 0.3587(3) 0.0542(13) Uani 1 1 d . . .
H14A H 0.3200 0.1776 0.3391 0.065 Uiso 1 1 calc R . .
C15 C 0.3673(3) 0.4221(6) 0.3563(3) 0.0698(16) Uani 1 1 d . . .
H15A H 0.4107 0.4008 0.3361 0.084 Uiso 1 1 calc R . .
C16 C 0.3594(3) 0.5855(6) 0.3817(3) 0.0701(16) Uani 1 1 d . . .
C17 C 0.2935(3) 0.6198(5) 0.4124(3) 0.0508(13) Uani 1 1 d . . .
C18 C 0.2733(3) 0.7747(5) 0.4406(3) 0.0604(14) Uani 1 1 d . . .
H18A H 0.3042 0.8729 0.4390 0.072 Uiso 1 1 calc R . .
C19 C 0.2089(3) 0.7835(5) 0.4705(3) 0.0553(14) Uani 1 1 d . . .
H19A H 0.1963 0.8875 0.4896 0.066 Uiso 1 1 calc R . .
C20 C 0.1616(3) 0.6383(5) 0.4728(2) 0.0529(13) Uani 1 1 d . . .
H20A H 0.1180 0.6450 0.4938 0.063 Uiso 1 1 calc R . .
C21 C 0.2427(3) 0.4816(4) 0.4156(2) 0.0369(11) Uani 1 1 d . . .
C22 C 0.4250(4) 0.7242(7) 0.3841(4) 0.0808(18) Uani 1 1 d . . .
C23 C 0.4919(4) 0.7482(7) 0.4452(4) 0.093(2) Uani 1 1 d . . .
H23A H 0.4976 0.6780 0.4876 0.112 Uiso 1 1 calc R . .
C24 C 0.5538(4) 0.8713(9) 0.4500(4) 0.101(2) Uani 1 1 d . . .
H24A H 0.5992 0.8798 0.4940 0.121 Uiso 1 1 calc R . .
C25 C 0.5475(4) 0.9797(8) 0.3893(5) 0.106(2) Uani 1 1 d . . .
H25A H 0.5875 1.0633 0.3909 0.127 Uiso 1 1 calc R . .
C26 C 0.4752(4) 0.9564(6) 0.3227(5) 0.0729(19) Uani 1 1 d . . .
C27 C 0.4668(5) 1.0534(8) 0.2603(6) 0.130(3) Uani 1 1 d . . .
H27A H 0.5067 1.1361 0.2605 0.156 Uiso 1 1 calc R . .
C28 C 0.4012(5) 1.0315(11) 0.1978(5) 0.121(3) Uani 1 1 d . . .
H28A H 0.3970 1.1020 0.1559 0.146 Uiso 1 1 calc R . .
C29 C 0.3388(4) 0.9101(9) 0.1915(4) 0.107(2) Uani 1 1 d . . .
H29A H 0.2949 0.9002 0.1464 0.129 Uiso 1 1 calc R . .
C30 C 0.3429(4) 0.8054(7) 0.2525(4) 0.0785(17) Uani 1 1 d . . .
H30A H 0.3021 0.7232 0.2501 0.094 Uiso 1 1 calc R . .
C31 C 0.4138(4) 0.8278(6) 0.3212(4) 0.0605(16) 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C13 O1 B1 111.0(3) . . ?
C20 N1 C21 119.2(3) . . ?
C20 N1 B1 133.3(3) . . ?
C21 N1 B1 107.4(3) . . ?
C6 C1 C2 114.6(5) . . ?
C6 C1 B1 121.9(5) . . ?
C2 C1 B1 123.5(5) . . ?
O1 B1 C1 111.9(4) . . ?
O1 B1 C7 109.3(4) . . ?
C1 B1 C7 119.0(4) . . ?
O1 B1 N1 97.6(3) . . ?
C1 B1 N1 108.2(4) . . ?
C7 B1 N1 108.5(4) . . ?
C3 C2 C1 123.6(5) . . ?
C5 C4 C3 118.0(6) . . ?
C2 C3 C4 120.2(5) . . ?
C4 C5 C6 121.4(5) . . ?
C5 C6 C1 122.2(5) . . ?
C8 C7 C12 115.4(4) . . ?
C8 C7 B1 120.3(5) . . ?
C12 C7 B1 124.3(5) . . ?
C9 C8 C7 123.9(5) . . ?
C8 C9 C10 118.5(6) . . ?
C7 C12 C11 122.3(5) . . ?
C11 C10 C9 120.5(6) . . ?
C10 C11 C12 119.3(5) . . ?
O1 C13 C14 128.6(4) . . ?
O1 C13 C21 112.3(4) . . ?
C14 C13 C21 119.1(4) . . ?
C13 C14 C15 117.7(4) . . ?
C16 C15 C14 124.0(4) . . ?
C15 C16 C17 118.6(4) . . ?
C15 C16 C22 121.0(4) . . ?
C17 C16 C22 120.1(4) . . ?
C21 C17 C18 115.4(4) . . ?
C21 C17 C16 116.1(4) . . ?
C18 C17 C16 128.4(4) . . ?
C19 C18 C17 120.7(4) . . ?
C18 C19 C20 120.4(4) . . ?
N1 C20 C19 120.1(4) . . ?
N1 C21 C17 124.2(4) . . ?
N1 C21 C13 111.4(4) . . ?
C17 C21 C13 124.4(4) . . ?
C23 C22 C31 119.2(6) . . ?
C23 C22 C16 122.3(6) . . ?
C31 C22 C16 118.5(6) . . ?
C22 C23 C24 124.6(7) . . ?
C25 C24 C23 119.9(7) . . ?
C24 C25 C26 116.3(7) . . ?
C27 C26 C31 119.2(7) . . ?
C27 C26 C25 119.5(7) . . ?
C31 C26 C25 121.3(6) . . ?
C28 C27 C26 120.3(8) . . ?
C27 C28 C29 124.3(8) . . ?
C30 C29 C28 119.2(7) . . ?
C29 C30 C31 117.4(6) . . ?
C22 C31 C26 118.7(7) . . ?
C22 C31 C30 121.6(6) . . ?
C26 C31 C30 119.7(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.334(4) . ?
O1 B1 1.535(5) . ?
N1 C20 1.331(4) . ?
N1 C21 1.347(4) . ?
N1 B1 1.646(5) . ?
C1 C6 1.385(5) . ?
C1 C2 1.397(5) . ?
C1 B1 1.578(6) . ?
B1 C7 1.606(6) . ?
C2 C3 1.367(5) . ?
C4 C5 1.365(6) . ?
C4 C3 1.378(6) . ?
C5 C6 1.384(6) . ?
C7 C8 1.382(5) . ?
C7 C12 1.386(5) . ?
C8 C9 1.379(6) . ?
C9 C10 1.379(6) . ?
C12 C11 1.400(6) . ?
C10 C11 1.361(6) . ?
C13 C14 1.352(5) . ?
C13 C21 1.398(5) . ?
C14 C15 1.406(5) . ?
C15 C16 1.374(5) . ?
C16 C17 1.416(5) . ?
C16 C22 1.536(6) . ?
C17 C21 1.387(5) . ?
C17 C18 1.394(5) . ?
C18 C19 1.361(5) . ?
C19 C20 1.390(5) . ?
C22 C23 1.339(6) . ?
C22 C31 1.373(6) . ?
C23 C24 1.399(6) . ?
C24 C25 1.375(7) . ?
C25 C26 1.449(7) . ?
C26 C27 1.344(8) . ?
C26 C31 1.433(6) . ?
C27 C28 1.338(8) . ?
C28 C29 1.390(8) . ?
C29 C30 1.370(6) . ?
C30 C31 1.459(6) . ?
