#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/83/1508384.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_1508384
loop_
_publ_author_name
'Bag, Pradip '
'Itkis, Mikhail E. '
'Pal, Sushanta K. '
'Bekyarova, Elena '
'Donnadieu, Bruno '
'Haddon, Robert C. '
_publ_section_title
;
 Synthesis, Structure and Solid State Properties of Cyclohexanemethylamine
 Substituted Phenalenyl Based Molecular Conductor
;
_journal_issue                   2
_journal_name_full               Crystals
_journal_page_first              446
_journal_page_last               465
_journal_paper_doi               10.3390/cryst2020446
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C20 H20 B0.50 N O'
_chemical_formula_sum            'C20 H20 B0.5 N O'
_chemical_formula_weight         295.78
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 97.597(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.4373(15)
_cell_length_b                   6.1623(4)
_cell_length_c                   23.2775(16)
_cell_measurement_reflns_used    5553
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.77
_cell_volume                     3048.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir 97'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19619
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0401
_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)+(0.0517P)²+2.9244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                2583
_reflns_number_total             3460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file
C20H20B0.50NO_C2_c_crystals-02-00446-s002_DC128.cif
_cod_data_source_block           11_chateigner_1508384
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C20 H20 B0.50 N O'
_cod_database_code               1508384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
B1 B 0.0000 0.7343(4) 0.2500 0.0203(4) Uani 1 2 d S
O1 O -0.02005(4) 0.87779(15) 0.29411(4) 0.0220(2) Uani 1 1 d .
N1 N -0.05438(5) 0.58347(19) 0.22434(5) 0.0208(3) Uani 1 1 d .
C1 C -0.07382(6) 0.8511(2) 0.31670(6) 0.0195(3) Uani 1 1 d .
C2 C -0.08794(7) 0.9986(2) 0.35914(6) 0.0226(3) Uani 1 1 d .
C3 C -0.14077(7) 0.9728(2) 0.38563(6) 0.0237(3) Uani 1 1 d .
C4 C -0.23490(7) 0.7557(3) 0.40136(6) 0.0276(3) Uani 1 1 d .
C5 C -0.27216(7) 0.5749(3) 0.38861(7) 0.0298(3) Uani 1 1 d .
C6 C -0.25894(7) 0.4273(3) 0.34670(7) 0.0276(3) Uani 1 1 d .
C7 C -0.19323(7) 0.3187(2) 0.27137(6) 0.0245(3) Uani 1 1 d .
C8 C -0.14464(7) 0.3567(2) 0.24049(6) 0.0236(3) Uani 1 1 d .
C9 C -0.10362(6) 0.5381(2) 0.25304(5) 0.0205(3) Uani 1 1 d .
C20 C -0.04103(7) 0.4411(2) 0.17689(6) 0.0219(3) Uani 1 1 d .
C21 C -0.08423(7) 0.4697(2) 0.11993(6) 0.0223(3) Uani 1 1 d .
C22 C -0.06334(8) 0.3125(2) 0.07556(6) 0.0266(3) Uani 1 1 d .
C23 C -0.10313(9) 0.3323(3) 0.01627(6) 0.0305(4) Uani 1 1 d .
C24 C -0.10522(9) 0.5644(3) -0.00578(6) 0.0304(4) Uani 1 1 d .
C25 C -0.12738(8) 0.7186(3) 0.03859(6) 0.0295(3) Uani 1 1 d .
C26 C -0.08552(8) 0.7012(2) 0.09698(6) 0.0252(3) Uani 1 1 d .
C3A C -0.18180(7) 0.7936(2) 0.37261(6) 0.0225(3) Uani 1 1 d .
C6A C -0.20774(7) 0.4608(2) 0.31612(6) 0.0230(3) Uani 1 1 d .
C9A C -0.11523(6) 0.6789(2) 0.29970(5) 0.0194(3) Uani 1 1 d .
C9B C -0.16828(6) 0.6448(2) 0.32938(6) 0.0201(3) Uani 1 1 d .
H2 H -0.0593(8) 1.118(3) 0.3680(7) 0.0321(10) Uiso 1 1 d .
H3 H -0.1514(8) 1.077(3) 0.4149(8) 0.0321(10) Uiso 1 1 d .
H4 H -0.2437(8) 0.862(3) 0.4317(8) 0.0321(10) Uiso 1 1 d .
H5 H -0.3074(8) 0.554(3) 0.4090(7) 0.0321(10) Uiso 1 1 d .
H6 H -0.2860(8) 0.297(3) 0.3369(7) 0.0321(10) Uiso 1 1 d .
H7 H -0.2202(8) 0.190(3) 0.2632(7) 0.0321(10) Uiso 1 1 d .
H8 H -0.1358(8) 0.254(3) 0.2104(8) 0.0321(10) Uiso 1 1 d .
H20A H -0.0413(8) 0.287(3) 0.1897(7) 0.0321(10) Uiso 1 1 d .
H20B H 0.0035(9) 0.474(3) 0.1694(8) 0.0321(10) Uiso 1 1 d .
H21 H -0.1303(8) 0.432(3) 0.1267(7) 0.0321(10) Uiso 1 1 d .
H22A H -0.0637(8) 0.160(3) 0.0909(8) 0.0321(10) Uiso 1 1 d .
H22B H -0.0196(9) 0.345(3) 0.0715(7) 0.0321(10) Uiso 1 1 d .
H23A H -0.0851(8) 0.232(3) -0.0119(8) 0.0321(10) Uiso 1 1 d .
H23B H -0.1490(9) 0.283(3) 0.0190(8) 0.0321(10) Uiso 1 1 d .
H24A H -0.1335(8) 0.570(3) -0.0435(8) 0.0321(10) Uiso 1 1 d .
H24B H -0.0612(8) 0.612(3) -0.0125(7) 0.0321(10) Uiso 1 1 d .
H25A H -0.1736(8) 0.682(3) 0.0435(7) 0.0321(10) Uiso 1 1 d .
H25B H -0.1266(8) 0.873(3) 0.0238(7) 0.0321(10) Uiso 1 1 d .
H26A H -0.0407(9) 0.740(3) 0.0910(8) 0.0321(10) Uiso 1 1 d .
H26B H -0.1014(8) 0.802(3) 0.1266(8) 0.0321(10) 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 0.0033 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'
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'
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
O1 B1 O1 105.57(16) 2 .
O1 B1 N1 111.62(6) 2 .
O1 B1 N1 110.97(6) . .
O1 B1 N1 110.97(6) 2 2
O1 B1 N1 111.62(6) . 2
N1 B1 N1 106.19(16) . 2
C1 O1 B1 123.35(10) . .
C9 N1 C20 119.40(12) . .
C9 N1 B1 122.10(9) . .
C20 N1 B1 115.95(10) . .
O1 C1 C2 118.27(12) . .
O1 C1 C9A 121.76(12) . .
C2 C1 C9A 119.96(13) . .
C3 C2 C1 120.66(13) . .
C3 C2 H2 122.3(10) . .
C1 C2 H2 117.0(10) . .
C2 C3 C3A 121.39(13) . .
C2 C3 H3 121.1(10) . .
C3A C3 H3 117.5(10) . .
C5 C4 C3A 120.73(14) . .
C5 C4 H4 121.5(10) . .
C3A C4 H4 117.7(10) . .
C4 C5 C6 120.87(14) . .
C4 C5 H5 118.5(11) . .
C6 C5 H5 120.7(11) . .
C5 C6 C6A 120.45(14) . .
C5 C6 H6 121.3(10) . .
C6A C6 H6 118.2(10) . .
C8 C7 C6A 122.42(13) . .
C8 C7 H7 120.5(10) . .
C6A C7 H7 117.1(10) . .
C7 C8 C9 121.30(13) . .
C7 C8 H8 120.0(10) . .
C9 C8 H8 118.6(10) . .
N1 C9 C8 124.12(12) . .
N1 C9 C9A 118.25(12) . .
C8 C9 C9A 117.62(13) . .
N1 C20 C21 115.40(11) . .
N1 C20 H20A 109.6(10) . .
C21 C20 H20A 110.2(10) . .
N1 C20 H20B 106.9(10) . .
C21 C20 H20B 107.8(10) . .
H20A C20 H20B 106.6(14) . .
C26 C21 C20 113.24(12) . .
C26 C21 C22 110.54(12) . .
C20 C21 C22 108.45(12) . .
C26 C21 H21 106.8(10) . .
C20 C21 H21 108.6(10) . .
C22 C21 H21 109.1(10) . .
C21 C22 C23 112.44(13) . .
C21 C22 H22A 109.7(10) . .
C23 C22 H22A 111.4(10) . .
C21 C22 H22B 107.8(10) . .
C23 C22 H22B 108.9(10) . .
H22A C22 H22B 106.3(14) . .
C24 C23 C22 111.62(13) . .
C24 C23 H23A 110.5(10) . .
C22 C23 H23A 108.7(10) . .
C24 C23 H23B 108.2(10) . .
C22 C23 H23B 109.9(10) . .
H23A C23 H23B 107.9(14) . .
C23 C24 C25 110.85(13) . .
C23 C24 H24A 108.4(10) . .
C25 C24 H24A 111.5(10) . .
C23 C24 H24B 109.6(10) . .
C25 C24 H24B 107.7(10) . .
H24A C24 H24B 108.7(14) . .
C24 C25 C26 111.05(13) . .
C24 C25 H25A 109.1(10) . .
C26 C25 H25A 110.1(9) . .
C24 C25 H25B 109.5(10) . .
C26 C25 H25B 109.6(10) . .
H25A C25 H25B 107.5(14) . .
C21 C26 C25 111.03(12) . .
C21 C26 H26A 107.2(10) . .
C25 C26 H26A 108.3(10) . .
C21 C26 H26B 109.0(10) . .
C25 C26 H26B 110.4(10) . .
H26A C26 H26B 110.8(14) . .
C4 C3A C3 122.86(13) . .
C4 C3A C9B 118.77(13) . .
C3 C3A C9B 118.36(13) . .
C6 C6A C9B 119.34(13) . .
C6 C6A C7 122.84(13) . .
C9B C6A C7 117.82(13) . .
C1 C9A C9B 119.35(12) . .
C1 C9A C9 120.14(12) . .
C9B C9A C9 120.50(12) . .
C3A C9B C9A 120.03(12) . .
C3A C9B C6A 119.81(13) . .
C9A C9B C6A 120.16(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O1 1.4622(16) 2
B1 O1 1.4622(16) .
B1 N1 1.5477(17) .
B1 N1 1.5477(17) 2
O1 C1 1.3387(16) .
N1 C9 1.3511(18) .
N1 C20 1.4682(17) .
C1 C2 1.4045(19) .
C1 C9A 1.4066(19) .
C2 C3 1.368(2) .
C2 H2 0.962(19) .
C3 C3A 1.419(2) .
C3 H3 0.986(18) .
C4 C5 1.380(2) .
C4 C3A 1.414(2) .
C4 H4 1.001(18) .
C5 C6 1.390(2) .
C5 H5 0.953(18) .
C6 C6A 1.400(2) .
C6 H6 1.002(18) .
C7 C8 1.362(2) .
C7 C6A 1.426(2) .
C7 H7 0.986(18) .
C8 C9 1.428(2) .
C8 H8 0.979(18) .
C9 C9A 1.4373(19) .
C20 C21 1.5238(18) .
C20 H20A 0.993(18) .
C20 H20B 1.014(18) .
C21 C26 1.5224(19) .
C21 C22 1.526(2) .
C21 H21 1.047(18) .
C22 C23 1.528(2) .
C22 H22A 1.005(18) .
C22 H22B 0.977(18) .
C23 C24 1.519(2) .
C23 H23A 1.012(18) .
C23 H23B 1.040(18) .
C24 C25 1.525(2) .
C24 H24A 1.000(18) .
C24 H24B 1.019(18) .
C25 C26 1.530(2) .
C25 H25A 1.036(18) .
C25 H25B 1.011(18) .
C26 H26A 1.017(18) .
C26 H26B 1.021(18) .
C3A C9B 1.4194(19) .
C6A C9B 1.4238(19) .
C9A C9B 1.4223(19) .
