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#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024001.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_4024001
loop_
_publ_author_name
'Cory A. Jaska'
'Warren E. Piers'
'Robert McDonald'
'Masood Parvez'
_publ_section_title
;
 Synthesis, Characterization, and Fluorescence Behavior of
 Twisted and Planar B₂N₂-Quaterphenyl Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5234
_journal_page_last               5243
_journal_paper_doi               10.1021/jo0706574
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C16 H25 B Cl N Si'
_chemical_formula_weight         305.72
_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                 97.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.601(5)
_cell_length_b                   11.924(6)
_cell_length_c                   13.140(5)
_cell_measurement_temperature    173(2)
_cell_volume                     1802.9(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6912
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.6355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                2818
_reflns_number_total             4111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0706574si20070330_124629.cif
_cod_data_source_block           c3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024001
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
Cl1 Cl 0.88406(5) 0.17480(5) 0.82909(4) 0.03336(15) Uani 1 1 d . . .
Si1 Si 0.58394(5) 0.18892(5) 0.71385(5) 0.03338(17) Uani 1 1 d . . .
N1 N 0.85273(14) 0.11097(14) 0.61860(12) 0.0258(4) Uani 1 1 d . . .
C1 C 0.71082(17) 0.26555(18) 0.67093(15) 0.0278(4) Uani 1 1 d . . .
C2 C 0.68853(18) 0.36005(18) 0.61691(16) 0.0313(5) Uani 1 1 d . . .
H2 H 0.6103 0.3879 0.6050 0.038 Uiso 1 1 d R . .
C3 C 0.77500(17) 0.43259(18) 0.57004(16) 0.0298(5) Uani 1 1 d . . .
H3 H 0.7611 0.4157 0.4981 0.036 Uiso 1 1 d R . .
C4 C 0.89969(17) 0.40513(18) 0.60887(16) 0.0309(5) Uani 1 1 d . . .
H4 H 0.9605 0.4566 0.5976 0.037 Uiso 1 1 d R . .
C5 C 0.93277(17) 0.31201(17) 0.66099(15) 0.0270(4) Uani 1 1 d . . .
H5 H 1.0138 0.2973 0.6812 0.032 Uiso 1 1 d R . .
C6 C 0.74564(19) 0.55833(18) 0.57526(16) 0.0331(5) Uani 1 1 d . . .
H6 H 0.6645 0.5645 0.5501 0.040 Uiso 1 1 d R . .
C7 C 0.7666(2) 0.6036(2) 0.68449(18) 0.0445(6) Uani 1 1 d . . .
H7A H 0.7470 0.6818 0.6843 0.053 Uiso 1 1 d R . .
H7B H 0.8471 0.5943 0.7108 0.053 Uiso 1 1 d R . .
H7C H 0.7194 0.5635 0.7271 0.053 Uiso 1 1 d R . .
C8 C 0.8098(2) 0.6279(2) 0.50310(18) 0.0408(6) Uani 1 1 d . . .
H8A H 0.7902 0.7057 0.5085 0.049 Uiso 1 1 d R . .
H8B H 0.7881 0.6030 0.4338 0.049 Uiso 1 1 d R . .
H8C H 0.8920 0.6183 0.5215 0.049 Uiso 1 1 d R . .
C9 C 0.89084(18) 0.00931(18) 0.65119(16) 0.0324(5) Uani 1 1 d . . .
H9 H 0.9166 -0.0023 0.7228 0.039 Uiso 1 1 d R . .
C10 C 0.8945(2) -0.07929(19) 0.58383(18) 0.0390(5) Uani 1 1 d . . .
H10 H 0.9218 -0.1512 0.6094 0.047 Uiso 1 1 d R . .
C11 C 0.8585(2) -0.0634(2) 0.48089(18) 0.0408(6) Uani 1 1 d . . .
H11 H 0.8588 -0.1251 0.4340 0.049 Uiso 1 1 d R . .
C12 C 0.8213(2) 0.0418(2) 0.44731(17) 0.0392(5) Uani 1 1 d . . .
H12 H 0.7982 0.0546 0.3755 0.047 Uiso 1 1 d R . .
C13 C 0.81980(19) 0.12685(19) 0.51735(15) 0.0331(5) Uani 1 1 d . . .
H13 H 0.7941 0.1998 0.4934 0.040 Uiso 1 1 d R . .
C14 C 0.4492(2) 0.2206(3) 0.62520(19) 0.0562(8) Uani 1 1 d . . .
H14A H 0.3843 0.1814 0.6471 0.067 Uiso 1 1 d R . .
H14B H 0.4593 0.1974 0.5569 0.067 Uiso 1 1 d R . .
H14C H 0.4349 0.2999 0.6258 0.067 Uiso 1 1 d R . .
C15 C 0.5594(2) 0.2327(3) 0.84577(18) 0.0488(7) Uani 1 1 d . . .
H15A H 0.4942 0.1926 0.8660 0.059 Uiso 1 1 d R . .
H15B H 0.5438 0.3117 0.8458 0.059 Uiso 1 1 d R . .
H15C H 0.6274 0.2168 0.8932 0.059 Uiso 1 1 d R . .
C16 C 0.6062(3) 0.0347(2) 0.7151(3) 0.0660(8) Uani 1 1 d . . .
H16A H 0.5401 -0.0022 0.7371 0.079 Uiso 1 1 d R . .
H16B H 0.6743 0.0174 0.7618 0.079 Uiso 1 1 d R . .
H16C H 0.6166 0.0093 0.6475 0.079 Uiso 1 1 d R . .
B1 B 0.8424(2) 0.2224(2) 0.69090(17) 0.0268(5) 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'
Cl Cl 0.1484 0.1585 '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'
Si Si 0.0817 0.0704 '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'
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
C16 Si1 C14 108.07(15) . . ?
C16 Si1 C15 107.84(14) . . ?
C14 Si1 C15 107.98(13) . . ?
C16 Si1 C1 111.78(11) . . ?
C14 Si1 C1 109.91(11) . . ?
C15 Si1 C1 111.14(11) . . ?
C9 N1 C13 118.80(18) . . ?
C9 N1 B1 126.18(17) . . ?
C13 N1 B1 115.02(17) . . ?
C2 C1 B1 118.22(18) . . ?
C2 C1 Si1 117.54(16) . . ?
B1 C1 Si1 124.19(15) . . ?
C1 C2 C3 127.10(19) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 113.5 . . ?
C4 C3 C2 113.29(17) . . ?
C4 C3 C6 113.84(18) . . ?
C2 C3 C6 112.10(17) . . ?
C4 C3 H3 108.8 . . ?
C2 C3 H3 104.1 . . ?
C6 C3 H3 103.7 . . ?
C5 C4 C3 123.71(19) . . ?
C5 C4 H4 116.2 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 B1 122.21(19) . . ?
C4 C5 H5 120.1 . . ?
B1 C5 H5 117.7 . . ?
C7 C6 C8 111.2(2) . . ?
C7 C6 C3 112.15(18) . . ?
C8 C6 C3 111.97(17) . . ?
C7 C6 H6 109.2 . . ?
C8 C6 H6 106.2 . . ?
C3 C6 H6 105.8 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.8 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 110.0 . . ?
C6 C8 H8B 109.4 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.1 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 121.5(2) . . ?
N1 C9 H9 119.4 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 121.1 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 119.7 . . ?
N1 C13 C12 122.1(2) . . ?
N1 C13 H13 119.2 . . ?
C12 C13 H13 118.7 . . ?
Si1 C14 H14A 110.0 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.0 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.7 . . ?
Si1 C15 H15B 109.0 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.7 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 110.0 . . ?
Si1 C16 H16B 108.7 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.8 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 B1 C1 113.03(18) . . ?
C5 B1 N1 107.62(15) . . ?
C1 B1 N1 107.61(16) . . ?
C5 B1 Cl1 110.03(15) . . ?
C1 B1 Cl1 111.90(14) . . ?
N1 B1 Cl1 106.31(14) . . ?
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
Cl1 B1 1.905(2) . ?
Si1 C16 1.857(3) . ?
Si1 C14 1.865(3) . ?
Si1 C15 1.866(3) . ?
Si1 C1 1.879(2) . ?
N1 C9 1.342(3) . ?
N1 C13 1.350(3) . ?
N1 B1 1.647(3) . ?
C1 C2 1.339(3) . ?
C1 B1 1.600(3) . ?
C2 C3 1.514(3) . ?
C2 H2 0.9600 . ?
C3 C4 1.507(3) . ?
C3 C6 1.541(3) . ?
C3 H3 0.9600 . ?
C4 C5 1.335(3) . ?
C4 H4 0.9600 . ?
C5 B1 1.581(3) . ?
C5 H5 0.9601 . ?
C6 C7 1.524(3) . ?
C6 C8 1.524(3) . ?
C6 H6 0.9600 . ?
C7 H7A 0.9599 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9601 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9600 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9600 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9599 . ?
C13 H13 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9601 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 Si1 C1 C2 146.1(2) . . . . ?
C14 Si1 C1 C2 26.1(2) . . . . ?
C15 Si1 C1 C2 -93.35(19) . . . . ?
C16 Si1 C1 B1 -31.3(2) . . . . ?
C14 Si1 C1 B1 -151.28(18) . . . . ?
C15 Si1 C1 B1 89.25(19) . . . . ?
B1 C1 C2 C3 0.7(3) . . . . ?
Si1 C1 C2 C3 -176.82(16) . . . . ?
C1 C2 C3 C4 -13.4(3) . . . . ?
C1 C2 C3 C6 -143.9(2) . . . . ?
C2 C3 C4 C5 14.0(3) . . . . ?
C6 C3 C4 C5 143.7(2) . . . . ?
C3 C4 C5 B1 -2.3(3) . . . . ?
C4 C3 C6 C7 -59.8(2) . . . . ?
C2 C3 C6 C7 70.4(2) . . . . ?
C4 C3 C6 C8 65.9(2) . . . . ?
C2 C3 C6 C8 -163.84(18) . . . . ?
C13 N1 C9 C10 -1.5(3) . . . . ?
B1 N1 C9 C10 179.10(19) . . . . ?
N1 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C9 N1 C13 C12 1.7(3) . . . . ?
B1 N1 C13 C12 -178.82(19) . . . . ?
C11 C12 C13 N1 -0.5(3) . . . . ?
C4 C5 B1 C1 -10.5(3) . . . . ?
C4 C5 B1 N1 108.2(2) . . . . ?
C4 C5 B1 Cl1 -136.41(18) . . . . ?
C2 C1 B1 C5 11.1(3) . . . . ?
Si1 C1 B1 C5 -171.51(14) . . . . ?
C2 C1 B1 N1 -107.6(2) . . . . ?
Si1 C1 B1 N1 69.8(2) . . . . ?
C2 C1 B1 Cl1 136.00(18) . . . . ?
Si1 C1 B1 Cl1 -46.6(2) . . . . ?
C9 N1 B1 C5 113.7(2) . . . . ?
C13 N1 B1 C5 -65.8(2) . . . . ?
C9 N1 B1 C1 -124.2(2) . . . . ?
C13 N1 B1 C1 56.3(2) . . . . ?
C9 N1 B1 Cl1 -4.2(2) . . . . ?
C13 N1 B1 Cl1 176.36(15) . . . . ?
