#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:58:49 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179029 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/27/4122799.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_4122799
loop_
_publ_author_name
'Ishibashi, Jacob S. A.'
'Marshall, Jonathan L.'
'Mazière, Audrey'
'Lovinger, Gabriel J.'
'Li, Bo'
'Zakharov, Lev N.'
'Dargelos, Alain'
'Graciaa, Alain'
'Chrostowska, Anna'
'Liu, Shih-Yuan'
_publ_section_title
;
 Two BN Isosteres of Anthracene: Synthesis and Characterization.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15414
_journal_page_last               15421
_journal_paper_doi               10.1021/ja508813v
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C18 H14 B N'
_chemical_formula_weight         255.11
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.583(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6082(4)
_cell_length_b                   5.8948(3)
_cell_length_c                   28.6991(15)
_cell_measurement_reflns_used    4215
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.74
_cell_measurement_theta_min      3.09
_cell_volume                     1284.60(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8807
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.777
_diffrn_reflns_theta_min         3.086
_diffrn_source                   'Incoatec I\mSCu'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+1.7109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2034
_reflns_number_total             2260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja508813v_si_003.cif
_cod_data_source_block           cu_liur245_0m
_cod_depositor_comments
'Adding full bibliography for 4122799--4122800.cif.'
_cod_database_code               4122799
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.870
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
N1 N 0.4341(2) 0.0227(4) 0.23458(7) 0.0267(5) Uani 1 1 d
B1 B 0.4641(3) 0.1633(5) 0.19611(9) 0.0280(6) Uani 1 1 d
C1 C 0.5476(3) 0.3926(4) 0.20891(8) 0.0302(6) Uani 1 1 d
C2 C 0.5971(3) 0.4406(4) 0.25347(8) 0.0254(5) Uani 1 1 d
C3 C 0.5738(3) 0.2824(4) 0.29107(8) 0.0270(5) Uani 1 1 d
C4 C 0.4861(3) 0.0682(4) 0.28080(7) 0.0228(5) Uani 1 1 d
C5 C 0.4633(3) -0.0826(4) 0.31654(8) 0.0265(5) Uani 1 1 d
C6 C 0.5300(3) -0.0389(4) 0.36298(8) 0.0258(5) Uani 1 1 d
C7 C 0.6210(3) 0.1679(4) 0.37282(8) 0.0279(5) Uani 1 1 d
C8 C 0.6387(3) 0.3251(4) 0.33634(8) 0.0280(5) Uani 1 1 d
C9 C 0.6912(3) 0.2098(4) 0.41910(9) 0.0324(6) Uani 1 1 d
C10 C 0.6692(3) 0.0554(5) 0.45349(9) 0.0365(6) Uani 1 1 d
C11 C 0.5772(3) -0.1477(5) 0.44380(8) 0.0332(6) Uani 1 1 d
C12 C 0.5099(3) -0.1939(4) 0.39992(8) 0.0302(6) Uani 1 1 d
C13 C 0.4194(3) 0.0838(4) 0.14439(8) 0.0275(5) Uani 1 1 d
C14 C 0.3348(3) -0.1214(4) 0.13269(8) 0.0304(6) Uani 1 1 d
C15 C 0.2987(3) -0.1853(5) 0.08645(9) 0.0346(6) Uani 1 1 d
C16 C 0.3467(3) -0.0441(5) 0.05081(9) 0.0362(6) Uani 1 1 d
C17 C 0.4312(3) 0.1578(5) 0.06140(9) 0.0351(6) Uani 1 1 d
C18 C 0.4667(3) 0.2199(4) 0.10746(9) 0.0313(6) Uani 1 1 d
H1 H 0.572(4) 0.500(5) 0.1822(10) 0.054(9) Uiso 1 1 d
H1N H 0.391(4) -0.121(6) 0.2282(10) 0.050(9) Uiso 1 1 d
H2 H 0.652(3) 0.578(5) 0.2628(8) 0.033(7) Uiso 1 1 d
H5 H 0.402(4) -0.233(5) 0.3082(9) 0.042(8) Uiso 1 1 d
H8 H 0.711(4) 0.470(5) 0.3439(9) 0.041(8) Uiso 1 1 d
H9 H 0.759(3) 0.351(5) 0.4251(8) 0.032(7) Uiso 1 1 d
H10 H 0.712(3) 0.089(5) 0.4845(9) 0.038(7) Uiso 1 1 d
H11 H 0.559(3) -0.255(5) 0.4691(9) 0.038(7) Uiso 1 1 d
H12 H 0.446(4) -0.329(5) 0.3933(9) 0.043(8) Uiso 1 1 d
H14 H 0.301(3) -0.226(5) 0.1581(9) 0.039(7) Uiso 1 1 d
H15 H 0.245(3) -0.324(5) 0.0792(9) 0.036(7) Uiso 1 1 d
H16 H 0.329(3) -0.086(5) 0.0180(10) 0.039(7) Uiso 1 1 d
H17 H 0.471(4) 0.262(5) 0.0364(10) 0.046(8) Uiso 1 1 d
H18 H 0.534(4) 0.362(5) 0.1144(9) 0.043(8) Uiso 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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
C4 N1 B1 125.8(2)
C4 N1 H1N 116.3(18)
B1 N1 H1N 117.2(18)
N1 B1 C1 114.6(2)
N1 B1 C13 121.8(2)
C1 B1 C13 123.5(2)
C2 C1 B1 120.2(2)
C2 C1 H1 122.1(17)
B1 C1 H1 117.5(17)
C1 C2 C3 122.4(2)
C1 C2 H2 123.0(15)
C3 C2 H2 114.6(15)
C8 C3 C2 122.0(2)
C8 C3 C4 118.8(2)
C2 C3 C4 119.1(2)
C5 C4 N1 123.1(2)
C5 C4 C3 119.3(2)
N1 C4 C3 117.6(2)
C4 C5 C6 121.8(2)
C4 C5 H5 117.5(15)
C6 C5 H5 120.6(15)
C12 C6 C5 122.5(2)
C12 C6 C7 118.6(2)
C5 C6 C7 118.9(2)
C8 C7 C6 118.9(2)
C8 C7 C9 122.1(2)
C6 C7 C9 119.0(2)
C3 C8 C7 122.2(2)
C3 C8 H8 120.1(15)
C7 C8 H8 117.6(15)
C10 C9 C7 120.3(2)
C10 C9 H9 121.6(15)
C7 C9 H9 118.0(15)
C9 C10 C11 120.6(2)
C9 C10 H10 119.2(17)
C11 C10 H10 120.2(17)
C12 C11 C10 120.6(2)
C12 C11 H11 119.7(16)
C10 C11 H11 119.7(16)
C11 C12 C6 120.9(2)
C11 C12 H12 121.1(17)
C6 C12 H12 118.0(17)
C18 C13 C14 116.8(2)
C18 C13 B1 119.6(2)
C14 C13 B1 123.5(2)
C15 C14 C13 121.5(2)
C15 C14 H14 119.0(16)
C13 C14 H14 119.4(16)
C16 C15 C14 119.8(2)
C16 C15 H15 119.6(16)
C14 C15 H15 120.6(16)
C17 C16 C15 119.8(2)
C17 C16 H16 117.8(17)
C15 C16 H16 122.3(17)
C16 C17 C18 120.0(2)
C16 C17 H17 121.8(17)
C18 C17 H17 118.2(17)
C17 C18 C13 122.0(2)
C17 C18 H18 118.7(16)
C13 C18 H18 119.2(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.387(3)
N1 B1 1.410(3)
N1 H1N 0.92(3)
B1 C1 1.529(4)
B1 C13 1.573(3)
C1 C2 1.341(3)
C1 H1 1.02(3)
C2 C3 1.445(3)
C2 H2 0.94(3)
C3 C8 1.384(3)
C3 C4 1.450(3)
C4 C5 1.376(3)
C5 C6 1.420(3)
C5 H5 1.02(3)
C6 C12 1.415(3)
C6 C7 1.422(3)
C7 C8 1.410(3)
C7 C9 1.422(3)
C8 H8 1.03(3)
C9 C10 1.361(4)
C9 H9 0.99(3)
C10 C11 1.405(4)
C10 H10 0.95(3)
C11 C12 1.357(3)
C11 H11 0.98(3)
C12 H12 0.94(3)
C13 C18 1.394(3)
C13 C14 1.401(3)
C14 C15 1.390(3)
C14 H14 1.00(3)
C15 C16 1.385(4)
C15 H15 0.93(3)
C16 C17 1.378(4)
C16 H16 0.97(3)
C17 C18 1.382(3)
C17 H17 1.00(3)
C18 H18 1.00(3)
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
C4 N1 B1 C1 -5.5(3)
C4 N1 B1 C13 172.7(2)
N1 B1 C1 C2 4.5(3)
C13 B1 C1 C2 -173.8(2)
B1 C1 C2 C3 -0.4(3)
C1 C2 C3 C8 174.4(2)
C1 C2 C3 C4 -3.1(3)
B1 N1 C4 C5 -175.5(2)
B1 N1 C4 C3 2.3(3)
C8 C3 C4 C5 2.7(3)
C2 C3 C4 C5 -179.8(2)
C8 C3 C4 N1 -175.3(2)
C2 C3 C4 N1 2.2(3)
N1 C4 C5 C6 175.0(2)
C3 C4 C5 C6 -2.8(3)
C4 C5 C6 C12 -179.0(2)
C4 C5 C6 C7 0.8(3)
C12 C6 C7 C8 -178.8(2)
C5 C6 C7 C8 1.4(3)
C12 C6 C7 C9 1.1(3)
C5 C6 C7 C9 -178.7(2)
C2 C3 C8 C7 -178.0(2)
C4 C3 C8 C7 -0.5(3)
C6 C7 C8 C3 -1.5(3)
C9 C7 C8 C3 178.6(2)
C8 C7 C9 C10 179.0(2)
C6 C7 C9 C10 -0.9(3)
C7 C9 C10 C11 0.1(4)
C9 C10 C11 C12 0.5(4)
C10 C11 C12 C6 -0.2(4)
C5 C6 C12 C11 179.2(2)
C7 C6 C12 C11 -0.6(3)
N1 B1 C13 C18 -174.0(2)
C1 B1 C13 C18 4.1(3)
N1 B1 C13 C14 5.2(3)
C1 B1 C13 C14 -176.6(2)
C18 C13 C14 C15 -0.4(3)
B1 C13 C14 C15 -179.7(2)
C13 C14 C15 C16 -0.1(4)
C14 C15 C16 C17 0.6(4)
C15 C16 C17 C18 -0.5(4)
C16 C17 C18 C13 0.0(4)
C14 C13 C18 C17 0.5(3)
B1 C13 C18 C17 179.7(2)
