#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/52/1505291.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_1505291
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            'C42 H54 B2 F8 N6 O12'
_chemical_formula_weight         1008.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.477(12)
_cell_angle_beta                 79.330(15)
_cell_angle_gamma                77.735(12)
_cell_formula_units_Z            1
_cell_length_a                   8.8787(16)
_cell_length_b                   11.0339(13)
_cell_length_c                   12.038(2)
_cell_measurement_reflns_used    5082
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.40
_cell_volume                     1125.2(3)
_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 0.992
_diffrn_measured_fraction_theta_max 0.855
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12750
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.40
_diffrn_reflns_theta_min         4.74
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5323
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0594
_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)+(0.0985P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                3266
_reflns_number_total             5323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062912xsi20061229_041259.cif
_cod_data_source_block           ll68
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.2013(2) 0.55566(17) 0.41514(17) 0.0203(4) Uani 1 1 d D . .
H101 H 0.184(3) 0.6414(16) 0.401(2) 0.030(7) Uiso 1 1 d D . .
C102 C 0.1159(3) 0.48406(19) 0.3751(2) 0.0191(5) Uani 1 1 d . . .
C103 C 0.0027(3) 0.5155(2) 0.3054(2) 0.0235(5) Uani 1 1 d . . .
H1-A H -0.0331 0.5995 0.2764 0.028 Uiso 1 1 calc R . .
C104 C -0.0556(3) 0.4178(2) 0.2803(2) 0.0259(5) Uani 1 1 d . . .
H10C H -0.1341 0.4351 0.2331 0.031 Uiso 1 1 calc R . .
C105 C -0.0011(3) 0.2929(2) 0.3232(2) 0.0245(5) Uani 1 1 d . . .
H10B H -0.0425 0.2282 0.3028 0.029 Uiso 1 1 calc R . .
C106 C 0.1104(3) 0.2624(2) 0.3939(2) 0.0241(5) Uani 1 1 d . . .
H10A H 0.1457 0.1785 0.4235 0.029 Uiso 1 1 calc R . .
C107 C 0.1686(2) 0.3605(2) 0.4197(2) 0.0195(5) Uani 1 1 d . . .
N108 N 0.2807(2) 0.36465(16) 0.48506(17) 0.0207(4) Uani 1 1 d D . .
H108 H 0.343(3) 0.303(2) 0.522(3) 0.051(9) Uiso 1 1 d D . .
C109 C 0.2997(3) 0.48221(19) 0.4804(2) 0.0193(5) Uani 1 1 d . . .
C110 C 0.4169(3) 0.5223(2) 0.5323(2) 0.0219(5) Uani 1 1 d . . .
H11A H 0.4104 0.4868 0.6131 0.026 Uiso 1 1 calc R . .
H11B H 0.3949 0.6144 0.5292 0.026 Uiso 1 1 calc R . .
C201 C 0.4309(3) 0.89531(19) 0.3889(2) 0.0241(5) Uani 1 1 d . . .
H20O H 0.3590 0.9293 0.3332 0.029 Uiso 1 1 calc R . .
H20P H 0.5054 0.9522 0.3829 0.029 Uiso 1 1 calc R . .
O202 O 0.51441(18) 0.77194(13) 0.36575(14) 0.0220(4) Uani 1 1 d . . .
C203 C 0.5837(3) 0.7678(2) 0.2488(2) 0.0243(5) Uani 1 1 d . . .
H20D H 0.6792 0.7022 0.2435 0.029 Uiso 1 1 calc R . .
H20E H 0.6149 0.8488 0.2181 0.029 Uiso 1 1 calc R . .
C204 C 0.4751(3) 0.74149(19) 0.1777(2) 0.0227(5) Uani 1 1 d . . .
H20F H 0.3709 0.7953 0.1943 0.027 Uiso 1 1 calc R . .
H20G H 0.5160 0.7587 0.0959 0.027 Uiso 1 1 calc R . .
O205 O 0.46328(18) 0.61193(13) 0.20520(14) 0.0232(4) Uani 1 1 d . . .
C206 C 0.3777(3) 0.5681(2) 0.1402(2) 0.0207(5) Uani 1 1 d . . .
C207 C 0.2866(3) 0.6430(2) 0.0652(2) 0.0239(5) Uani 1 1 d . . .
H20A H 0.2785 0.7310 0.0574 0.029 Uiso 1 1 calc R . .
C208 C 0.2071(3) 0.5909(2) 0.0016(2) 0.0255(5) Uani 1 1 d . . .
H20B H 0.1461 0.6431 -0.0503 0.031 Uiso 1 1 calc R . .
C209 C 0.2164(3) 0.4629(2) 0.0135(2) 0.0244(5) Uani 1 1 d . . .
H20C H 0.1613 0.4272 -0.0297 0.029 Uiso 1 1 calc R . .
C210 C 0.3067(3) 0.3870(2) 0.0890(2) 0.0216(5) Uani 1 1 d . . .
H21A H 0.3127 0.2992 0.0974 0.026 Uiso 1 1 calc R . .
C211 C 0.3880(3) 0.4376(2) 0.1522(2) 0.0209(5) Uani 1 1 d . . .
O212 O 0.47891(18) 0.36896(13) 0.22905(14) 0.0229(4) Uani 1 1 d . . .
C213 C 0.5109(3) 0.23641(19) 0.2241(2) 0.0216(5) Uani 1 1 d . . .
H21B H 0.5532 0.2179 0.1451 0.026 Uiso 1 1 calc R . .
H21C H 0.4135 0.2029 0.2489 0.026 Uiso 1 1 calc R . .
C214 C 0.6278(3) 0.1768(2) 0.3011(2) 0.0232(5) Uani 1 1 d . . .
H21D H 0.6781 0.0924 0.2804 0.028 Uiso 1 1 calc R . .
H21E H 0.7100 0.2274 0.2919 0.028 Uiso 1 1 calc R . .
O215 O 0.55199(18) 0.16819(13) 0.41621(14) 0.0226(4) Uani 1 1 d . . .
C216 C 0.6591(3) 0.1148(2) 0.4935(2) 0.0242(5) Uani 1 1 d . . .
H21K H 0.7373 0.1682 0.4885 0.029 Uiso 1 1 calc R . .
H21L H 0.7149 0.0311 0.4739 0.029 Uiso 1 1 calc R . .
B10 B -0.0056(3) 0.8817(2) 0.3030(3) 0.0266(6) Uani 1 1 d D . .
F11 F 0.11776(17) 0.80432(12) 0.35237(15) 0.0389(4) Uani 1 1 d D A .
F12 F 0.0267(3) 0.8647(5) 0.18758(18) 0.0550(12) Uani 0.825(14) 1 d P A 1
F13 F -0.0114(3) 1.00318(19) 0.3140(5) 0.0409(10) Uani 0.825(14) 1 d P A 1
F14 F -0.1450(4) 0.8450(4) 0.3513(5) 0.0366(14) Uani 0.825(14) 1 d P A 1
F12A F 0.021(3) 0.916(2) 0.1902(9) 0.103(10) Uiso 0.175(14) 1 d PD A 2
F13A F -0.0110(19) 0.9873(13) 0.3584(17) 0.051(5) Uiso 0.175(14) 1 d PD A 2
F14A F -0.1406(19) 0.837(3) 0.341(2) 0.067(13) Uiso 0.175(14) 1 d PD A 2
O01 O 0.2715(2) 0.95741(17) -0.02437(18) 0.0448(5) Uani 1 1 d . . .
O02 O 0.3320(2) 1.04394(17) 0.1078(2) 0.0460(6) Uani 1 1 d . . .
N02 N 0.2452(3) 1.03637(19) 0.0412(2) 0.0345(5) Uani 1 1 d . . .
C03 C 0.0971(3) 1.1294(2) 0.0421(3) 0.0376(7) Uani 1 1 d D . .
H03A H 0.0840 1.1636 -0.0362 0.056 Uiso 1 1 calc R . .
H03B H 0.1005 1.1971 0.0853 0.056 Uiso 1 1 calc R . .
H03C H 0.0092 1.0890 0.0778 0.056 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'
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'
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 110.03(18) . .
C109 N101 H101 127.2(17) . .
C102 N101 H101 122.7(17) . .
C103 C102 N101 132.0(2) . .
C103 C102 C107 122.5(2) . .
N101 C102 C107 105.50(19) . .
C104 C103 C102 116.3(2) . .
C104 C103 H1-A 121.8 . .
C102 C103 H1-A 121.8 . .
C103 C104 C105 121.5(2) . .
C103 C104 H10C 119.2 . .
C105 C104 H10C 119.2 . .
C106 C105 C104 121.9(2) . .
C106 C105 H10B 119.1 . .
C104 C105 H10B 119.1 . .
C105 C106 C107 116.7(2) . .
C105 C106 H10A 121.7 . .
C107 C106 H10A 121.7 . .
N108 C107 C106 132.4(2) . .
N108 C107 C102 106.49(19) . .
C106 C107 C102 121.1(2) . .
C109 N108 C107 109.66(18) . .
C109 N108 H108 119(2) . .
C107 N108 H108 131(2) . .
N108 C109 N101 108.30(19) . .
N108 C109 C110 125.36(19) . .
N101 C109 C110 126.23(19) . .
C109 C110 C110 110.1(2) . 2_666
C109 C110 H11A 109.6 . .
C110 C110 H11A 109.6 2_666 .
C109 C110 H11B 109.6 . .
C110 C110 H11B 109.6 2_666 .
H11A C110 H11B 108.2 . .
O202 C201 C216 108.05(18) . 2_666
O202 C201 H20O 110.1 . .
C216 C201 H20O 110.1 2_666 .
O202 C201 H20P 110.1 . .
C216 C201 H20P 110.1 2_666 .
H20O C201 H20P 108.4 . .
C203 O202 C201 112.37(17) . .
O202 C203 C204 112.37(19) . .
O202 C203 H20D 109.1 . .
C204 C203 H20D 109.1 . .
O202 C203 H20E 109.1 . .
C204 C203 H20E 109.1 . .
H20D C203 H20E 107.9 . .
O205 C204 C203 107.70(18) . .
O205 C204 H20F 110.2 . .
C203 C204 H20F 110.2 . .
O205 C204 H20G 110.2 . .
C203 C204 H20G 110.2 . .
H20F C204 H20G 108.5 . .
C206 O205 C204 115.70(17) . .
O205 C206 C207 124.48(19) . .
O205 C206 C211 116.18(19) . .
C207 C206 C211 119.3(2) . .
C206 C207 C208 120.6(2) . .
C206 C207 H20A 119.7 . .
C208 C207 H20A 119.7 . .
C209 C208 C207 120.2(2) . .
C209 C208 H20B 119.9 . .
C207 C208 H20B 119.9 . .
C208 C209 C210 119.7(2) . .
C208 C209 H20C 120.2 . .
C210 C209 H20C 120.2 . .
C211 C210 C209 120.8(2) . .
C211 C210 H21A 119.6 . .
C209 C210 H21A 119.6 . .
O212 C211 C210 124.30(19) . .
O212 C211 C206 116.29(19) . .
C210 C211 C206 119.4(2) . .
C211 O212 C213 114.84(17) . .
O212 C213 C214 108.36(18) . .
O212 C213 H21B 110.0 . .
C214 C213 H21B 110.0 . .
O212 C213 H21C 110.0 . .
C214 C213 H21C 110.0 . .
H21B C213 H21C 108.4 . .
O215 C214 C213 109.81(18) . .
O215 C214 H21D 109.7 . .
C213 C214 H21D 109.7 . .
O215 C214 H21E 109.7 . .
C213 C214 H21E 109.7 . .
H21D C214 H21E 108.2 . .
C214 O215 C216 112.03(17) . .
O215 C216 C201 108.34(18) . 2_666
O215 C216 H21K 110.0 . .
C201 C216 H21K 110.0 2_666 .
O215 C216 H21L 110.0 . .
C201 C216 H21L 110.0 2_666 .
H21K C216 H21L 108.4 . .
F12A B10 F13 85.8(9) . .
F12A B10 F14A 114.7(12) . .
F13 B10 F14A 116.4(13) . .
F12A B10 F14 119.0(10) . .
F13 B10 F14 111.2(3) . .
F13 B10 F12 109.3(3) . .
F14A B10 F12 103.7(13) . .
F14 B10 F12 109.5(3) . .
F12A B10 F11 117.5(10) . .
F13 B10 F11 110.9(3) . .
F14A B10 F11 109.9(11) . .
F14 B10 F11 109.9(3) . .
F12 B10 F11 105.9(2) . .
F12A B10 F13A 107.8(8) . .
F14A B10 F13A 108.8(13) . .
F14 B10 F13A 102.5(8) . .
F12 B10 F13A 131.0(8) . .
F11 B10 F13A 96.4(7) . .
O01 N02 O02 124.7(2) . .
O01 N02 C03 117.9(2) . .
O02 N02 C03 117.5(2) . .
N02 C03 H03A 109.5 . .
N02 C03 H03B 109.5 . .
H03A C03 H03B 109.5 . .
N02 C03 H03C 109.5 . .
H03A C03 H03C 109.5 . .
H03B C03 H03C 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 1.342(3) .
N101 C102 1.391(3) .
N101 H101 0.921(17) .
C102 C103 1.383(3) .
C102 C107 1.404(3) .
C103 C104 1.382(3) .
C103 H1-A 0.9500 .
C104 C105 1.414(3) .
C104 H10C 0.9500 .
C105 C106 1.380(3) .
C105 H10B 0.9500 .
C106 C107 1.390(3) .
C106 H10A 0.9500 .
C107 N108 1.390(3) .
N108 C109 1.335(3) .
N108 H108 0.902(18) .
C109 C110 1.478(3) .
C110 C110 1.551(4) 2_666
C110 H11A 0.9900 .
C110 H11B 0.9900 .
C201 O202 1.445(3) .
C201 C216 1.493(4) 2_666
C201 H20O 0.9900 .
C201 H20P 0.9900 .
O202 C203 1.432(3) .
C203 C204 1.498(3) .
C203 H20D 0.9900 .
C203 H20E 0.9900 .
C204 O205 1.440(3) .
C204 H20F 0.9900 .
C204 H20G 0.9900 .
O205 C206 1.383(3) .
C206 C207 1.385(3) .
C206 C211 1.411(3) .
C207 C208 1.385(3) .
C207 H20A 0.9500 .
C208 C209 1.384(3) .
C208 H20B 0.9500 .
C209 C210 1.389(3) .
C209 H20C 0.9500 .
C210 C211 1.383(3) .
C210 H21A 0.9500 .
C211 O212 1.375(3) .
O212 C213 1.438(3) .
C213 C214 1.502(3) .
C213 H21B 0.9900 .
C213 H21C 0.9900 .
C214 O215 1.423(3) .
C214 H21D 0.9900 .
C214 H21E 0.9900 .
O215 C216 1.430(3) .
C216 C201 1.493(4) 2_666
C216 H21K 0.9900 .
C216 H21L 0.9900 .
B10 F12A 1.344(8) .
B10 F13 1.356(3) .
B10 F14A 1.368(9) .
B10 F14 1.383(4) .
B10 F12 1.398(4) .
B10 F11 1.405(3) .
B10 F13A 1.415(8) .
O01 N02 1.219(3) .
O02 N02 1.233(3) .
N02 C03 1.486(3) .
C03 H03A 0.9800 .
C03 H03B 0.9800 .
C03 H03C 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 F11 0.921(17) 1.814(18) 2.716(2) 166(3) .
N108 H108 O215 0.902(18) 2.40(3) 2.960(2) 120(2) .
C110 H11B O202 0.99 2.65 3.330(3) 126.2 .
N108 H108 O202 0.902(18) 1.99(2) 2.837(2) 156(3) 2_666
C110 H11A O202 0.99 2.77 3.267(3) 111.3 2_666
C110 H11A O205 0.99 2.63 3.536(3) 152.4 2_666
C110 H11B O215 0.99 2.73 3.635(3) 151.7 2_666
