#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/52/1505289.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_1505289
loop_
_publ_author_name
'Li, Liwei'
'Clarkson, Guy J.'
_publ_section_title
;
 New bis(benzimidazole) cations for threading through dibenzo-24-crown-8.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              497
_journal_page_last               500
_journal_paper_doi               10.1021/ol062912x
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C44 H54 B2 F8 N6 O8'
_chemical_formula_weight         968.55
_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                 100.314(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.526(10)
_cell_length_b                   14.191(13)
_cell_length_c                   14.332(13)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.240
_cell_measurement_theta_min      2.301
_cell_volume                     2306(4)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Siemens SMART diffractometer'
_diffrn_measurement_method       '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  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26148
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0614
_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)+(0.0763P)²+0.8707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                4516
_reflns_number_total             5828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062912xsi20061229_041259.cif
_cod_data_source_block           ll55
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505289
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
N101 N 0.31897(13) 0.88033(11) -0.07464(11) 0.0322(3) Uani 1 1 d . . .
H101 H 0.270(2) 0.9268(16) -0.0760(16) 0.048 Uiso 1 1 d . . .
C102 C 0.28934(16) 0.78522(13) -0.07894(12) 0.0325(4) Uani 1 1 d . . .
C103 C 0.18215(17) 0.73805(14) -0.08921(14) 0.0394(4) Uani 1 1 d . . .
H10A H 0.1094 0.7709 -0.0947 0.047 Uiso 1 1 calc R . .
C104 C 0.18726(19) 0.64015(15) -0.09101(15) 0.0450(5) Uani 1 1 d . . .
H10B H 0.1159 0.6052 -0.0985 0.054 Uiso 1 1 calc R . .
C105 C 0.2941(2) 0.59158(14) -0.08216(15) 0.0447(5) Uani 1 1 d . . .
H10C H 0.2932 0.5247 -0.0838 0.054 Uiso 1 1 calc R . .
C106 C 0.40056(18) 0.63792(13) -0.07111(14) 0.0396(4) Uani 1 1 d . . .
H10D H 0.4732 0.6049 -0.0645 0.047 Uiso 1 1 calc R . .
C107 C 0.39583(16) 0.73604(13) -0.07016(12) 0.0321(4) Uani 1 1 d . . .
N108 N 0.48381(14) 0.80392(10) -0.06122(11) 0.0329(3) Uani 1 1 d . . .
H108 H 0.557(2) 0.7913(16) -0.0542(17) 0.049 Uiso 1 1 d . . .
C109 C 0.43506(15) 0.88955(12) -0.06341(12) 0.0302(4) Uani 1 1 d . . .
C110 C 0.50165(16) 0.98013(12) -0.05010(13) 0.0331(4) Uani 1 1 d . . .
H11A H 0.4659 1.0261 -0.0988 0.040 Uiso 1 1 calc R . .
H11B H 0.5844 0.9695 -0.0574 0.040 Uiso 1 1 calc R . .
C201 C 0.86904(15) 0.90435(13) 0.04199(14) 0.0356(4) Uani 1 1 d . . .
H20G H 0.8862 0.8361 0.0487 0.043 Uiso 1 1 calc R . .
H20H H 0.9390 0.9396 0.0742 0.043 Uiso 1 1 calc R . .
O202 O 0.76807(10) 0.92736(8) 0.08374(9) 0.0325(3) Uani 1 1 d . . .
C203 C 0.78038(16) 0.89465(13) 0.17951(13) 0.0339(4) Uani 1 1 d . . .
H20I H 0.7435 0.9408 0.2169 0.041 Uiso 1 1 calc R . .
H20J H 0.8653 0.8909 0.2075 0.041 Uiso 1 1 calc R . .
C204 C 0.72476(14) 0.79965(12) 0.18667(13) 0.0323(4) Uani 1 1 d . . .
H20K H 0.7482 0.7561 0.1394 0.039 Uiso 1 1 calc R . .
H20L H 0.7517 0.7728 0.2506 0.039 Uiso 1 1 calc R . .
O205 O 0.59834(10) 0.81076(8) 0.16930(9) 0.0341(3) Uani 1 1 d . . .
C206 C 0.53551(15) 0.72959(12) 0.17672(12) 0.0305(4) Uani 1 1 d . . .
C207 C 0.58633(16) 0.64077(13) 0.19174(13) 0.0351(4) Uani 1 1 d . . .
H20A H 0.6694 0.6341 0.1983 0.042 Uiso 1 1 calc R . .
C208 C 0.51648(18) 0.56112(13) 0.19731(14) 0.0392(4) Uani 1 1 d . . .
H20B H 0.5520 0.5008 0.2081 0.047 Uiso 1 1 calc R . .
C209 C 0.39649(18) 0.57051(14) 0.18710(14) 0.0401(4) Uani 1 1 d . . .
H20C H 0.3490 0.5162 0.1898 0.048 Uiso 1 1 calc R . .
C210 C 0.34325(16) 0.65900(13) 0.17275(13) 0.0358(4) Uani 1 1 d . . .
H21A H 0.2600 0.6646 0.1658 0.043 Uiso 1 1 calc R . .
C211 C 0.41200(15) 0.73913(12) 0.16861(12) 0.0299(4) Uani 1 1 d . . .
O212 O 0.36607(10) 0.82862(8) 0.15528(9) 0.0336(3) Uani 1 1 d . . .
C213 C 0.24361(14) 0.83640(13) 0.16409(13) 0.0324(4) Uani 1 1 d . . .
H21C H 0.2316 0.8075 0.2245 0.039 Uiso 1 1 calc R . .
H21D H 0.1939 0.8022 0.1114 0.039 Uiso 1 1 calc R . .
C214 C 0.20786(16) 0.93821(13) 0.16183(13) 0.0342(4) Uani 1 1 d . . .
H21E H 0.1356 0.9454 0.1895 0.041 Uiso 1 1 calc R . .
H21F H 0.2713 0.9761 0.2001 0.041 Uiso 1 1 calc R . .
O215 O 0.18648(11) 0.97118(9) 0.06629(9) 0.0349(3) Uani 1 1 d . . .
C216 C 0.15866(17) 1.06921(13) 0.06093(14) 0.0377(4) Uani 1 1 d . . .
H21G H 0.2264 1.1065 0.0938 0.045 Uiso 1 1 calc R . .
H21H H 0.0899 1.0820 0.0916 0.045 Uiso 1 1 calc R . .
B10 B 0.9918(2) 0.62927(18) 0.20762(18) 0.0449(5) Uani 1 1 d . . .
F11 F 1.0328(7) 0.6719(6) 0.1375(5) 0.098(3) Uani 0.574(17) 1 d P A 1
F12 F 1.0558(7) 0.5823(6) 0.2871(6) 0.0729(17) Uani 0.574(17) 1 d P A 1
F13 F 0.8825(5) 0.5897(6) 0.1772(7) 0.0613(16) Uani 0.574(17) 1 d P A 1
F14 F 0.9531(5) 0.6989(7) 0.2644(5) 0.080(2) Uani 0.574(17) 1 d P A 1
F1A F 0.9862(8) 0.7224(3) 0.2210(10) 0.086(4) Uani 0.426(17) 1 d P A 2
F2A F 1.0559(6) 0.6129(14) 0.1336(7) 0.120(5) Uani 0.426(17) 1 d P A 2
F3A F 1.0802(11) 0.5821(8) 0.2576(9) 0.081(2) Uani 0.426(17) 1 d P A 2
F4A F 0.9003(12) 0.5698(11) 0.1721(9) 0.095(3) Uani 0.426(17) 1 d P A 2
N01 N 0.70394(17) 0.69972(14) -0.05262(16) 0.0560(5) Uani 1 1 d . . .
C02 C 0.77716(18) 0.64782(17) -0.05484(15) 0.0458(5) Uani 1 1 d . . .
C03 C 0.8717(2) 0.5795(3) -0.0579(2) 0.0787(9) Uani 1 1 d . . .
H03C H 0.9305 0.5843 0.0004 0.118 Uiso 1 1 calc R . .
H03B H 0.9092 0.5929 -0.1127 0.118 Uiso 1 1 calc R . .
H03A H 0.8386 0.5157 -0.0636 0.118 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C109 N101 C102 109.62(15) . .
C109 N101 H101 124.5(16) . .
C102 N101 H101 125.8(16) . .
C103 C102 N101 132.75(17) . .
C103 C102 C107 121.25(18) . .
N101 C102 C107 106.00(16) . .
C102 C103 C104 116.31(19) . .
C102 C103 H10A 121.8 . .
C104 C103 H10A 121.8 . .
C103 C104 C105 122.06(19) . .
C103 C104 H10B 119.0 . .
C105 C104 H10B 119.0 . .
C106 C105 C104 121.9(2) . .
C106 C105 H10C 119.1 . .
C104 C105 H10C 119.1 . .
C105 C106 C107 116.29(19) . .
C105 C106 H10D 121.9 . .
C107 C106 H10D 121.9 . .
N108 C107 C106 131.70(18) . .
N108 C107 C102 106.09(17) . .
C106 C107 C102 122.21(17) . .
C109 N108 C107 109.37(16) . .
C109 N108 H108 126.7(16) . .
C107 N108 H108 123.9(16) . .
N101 C109 N108 108.92(16) . .
N101 C109 C110 125.86(16) . .
N108 C109 C110 125.15(17) . .
C109 C110 C110 109.55(18) . 3_675
C109 C110 H11A 109.8 . .
C110 C110 H11A 109.8 3_675 .
C109 C110 H11B 109.8 . .
C110 C110 H11B 109.8 3_675 .
H11A C110 H11B 108.2 . .
O202 C201 C216 107.86(15) . 3_675
O202 C201 H20G 110.1 . .
C216 C201 H20G 110.1 3_675 .
O202 C201 H20H 110.1 . .
C216 C201 H20H 110.1 3_675 .
H20G C201 H20H 108.4 . .
C203 O202 C201 112.12(14) . .
O202 C203 C204 112.68(15) . .
O202 C203 H20I 109.1 . .
C204 C203 H20I 109.1 . .
O202 C203 H20J 109.1 . .
C204 C203 H20J 109.1 . .
H20I C203 H20J 107.8 . .
O205 C204 C203 108.66(14) . .
O205 C204 H20K 110.0 . .
C203 C204 H20K 110.0 . .
O205 C204 H20L 110.0 . .
C203 C204 H20L 110.0 . .
H20K C204 H20L 108.3 . .
C206 O205 C204 115.15(13) . .
O205 C206 C207 123.94(16) . .
O205 C206 C211 116.74(15) . .
C207 C206 C211 119.32(16) . .
C206 C207 C208 120.71(18) . .
C206 C207 H20A 119.6 . .
C208 C207 H20A 119.6 . .
C209 C208 C207 119.71(18) . .
C209 C208 H20B 120.1 . .
C207 C208 H20B 120.1 . .
C208 C209 C210 120.75(18) . .
C208 C209 H20C 119.6 . .
C210 C209 H20C 119.6 . .
C211 C210 C209 120.12(18) . .
C211 C210 H21A 119.9 . .
C209 C210 H21A 119.9 . .
O212 C211 C210 123.47(16) . .
O212 C211 C206 117.16(15) . .
C210 C211 C206 119.36(16) . .
C211 O212 C213 114.60(13) . .
O212 C213 C214 109.91(14) . .
O212 C213 H21C 109.7 . .
C214 C213 H21C 109.7 . .
O212 C213 H21D 109.7 . .
C214 C213 H21D 109.7 . .
H21C C213 H21D 108.2 . .
O215 C214 C213 109.63(14) . .
O215 C214 H21E 109.7 . .
C213 C214 H21E 109.7 . .
O215 C214 H21F 109.7 . .
C213 C214 H21F 109.7 . .
H21E C214 H21F 108.2 . .
C214 O215 C216 111.72(14) . .
O215 C216 C201 107.65(15) . 3_675
O215 C216 H21G 110.2 . .
C201 C216 H21G 110.2 3_675 .
O215 C216 H21H 110.2 . .
C201 C216 H21H 110.2 3_675 .
H21G C216 H21H 108.5 . .
F3A B10 F11 107.3(9) . .
F3A B10 F1A 118.4(6) . .
F11 B10 F1A 72.1(5) . .
F3A B10 F4A 110.9(8) . .
F11 B10 F4A 110.6(6) . .
F1A B10 F4A 127.2(10) . .
F3A B10 F13 122.6(7) . .
F11 B10 F13 112.0(5) . .
F1A B10 F13 112.5(5) . .
F4A B10 F13 15.2(8) . .
F3A B10 F14 109.8(6) . .
F11 B10 F14 108.1(4) . .
F1A B10 F14 36.1(3) . .
F4A B10 F14 110.1(10) . .
F13 B10 F14 95.9(5) . .
F3A B10 F12 22.9(4) . .
F11 B10 F12 128.4(6) . .
F1A B10 F12 112.5(7) . .
F4A B10 F12 105.3(7) . .
F13 B10 F12 112.3(5) . .
F14 B10 F12 92.3(7) . .
F3A B10 F2A 82.4(11) . .
F11 B10 F2A 37.3(5) . .
F1A B10 F2A 108.3(5) . .
F4A B10 F2A 95.2(10) . .
F13 B10 F2A 105.4(6) . .
F14 B10 F2A 144.4(5) . .
F12 B10 F2A 105.1(10) . .
N01 C02 C03 179.5(3) . .
C02 C03 H03C 109.5 . .
C02 C03 H03B 109.5 . .
H03C C03 H03B 109.5 . .
C02 C03 H03A 109.5 . .
H03C C03 H03A 109.5 . .
H03B C03 H03A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N101 C109 1.325(3) .
N101 C102 1.391(3) .
N101 H101 0.86(2) .
C102 C103 1.390(3) .
C102 C107 1.398(3) .
C103 C104 1.391(3) .
C103 H10A 0.9500 .
C104 C105 1.397(3) .
C104 H10B 0.9500 .
C105 C106 1.376(3) .
C105 H10C 0.9500 .
C106 C107 1.394(3) .
C106 H10D 0.9500 .
C107 N108 1.388(2) .
N108 C109 1.337(2) .
N108 H108 0.85(2) .
C109 C110 1.492(3) .
C110 C110 1.550(4) 3_675
C110 H11A 0.9900 .
C110 H11B 0.9900 .
C201 O202 1.438(2) .
C201 C216 1.500(3) 3_675
C201 H20G 0.9900 .
C201 H20H 0.9900 .
O202 C203 1.432(2) .
C203 C204 1.504(3) .
C203 H20I 0.9900 .
C203 H20J 0.9900 .
C204 O205 1.442(2) .
C204 H20K 0.9900 .
C204 H20L 0.9900 .
O205 C206 1.375(2) .
C206 C207 1.390(3) .
C206 C211 1.414(3) .
C207 C208 1.398(3) .
C207 H20A 0.9500 .
C208 C209 1.371(3) .
C208 H20B 0.9500 .
C209 C210 1.397(3) .
C209 H20C 0.9500 .
C210 C211 1.393(3) .
C210 H21A 0.9500 .
C211 O212 1.376(2) .
O212 C213 1.444(2) .
C213 C214 1.501(3) .
C213 H21C 0.9900 .
C213 H21D 0.9900 .
C214 O215 1.426(2) .
C214 H21E 0.9900 .
C214 H21F 0.9900 .
O215 C216 1.427(2) .
C216 C201 1.500(3) 3_675
C216 H21G 0.9900 .
C216 H21H 0.9900 .
B10 F3A 1.318(11) .
B10 F11 1.330(5) .
B10 F1A 1.338(7) .
B10 F4A 1.375(12) .
B10 F13 1.377(8) .
B10 F14 1.403(5) .
B10 F12 1.409(8) .
B10 F2A 1.417(6) .
N01 C02 1.125(3) .
C02 C03 1.465(3) .
C03 H03C 0.9800 .
C03 H03B 0.9800 .
C03 H03A 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N101 H101 O215 0.86(2) 2.49(2) 3.030(3) 121.3(19) .
N108 H108 N01 0.85(2) 2.13(2) 2.920(3) 154(2) .
C110 H11B O202 0.99 2.72 3.400(3) 126.2 .
N101 H101 O202 0.86(2) 2.11(2) 2.903(3) 151(2) 3_675
C110 H11A O202 0.99 2.82 3.329(3) 112.5 3_675
C110 H11A O205 0.99 2.58 3.514(3) 157.1 3_675
C110 H11B O215 0.99 2.80 3.708(4) 153.5 3_675
