#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/52/1505285.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_1505285
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 Cl2 N6 O16'
_chemical_formula_weight         993.83
_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                 99.034(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.681(4)
_cell_length_b                   14.113(4)
_cell_length_c                   14.416(5)
_cell_measurement_reflns_used    5042
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      3.20
_cell_volume                     2347.1(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.903
_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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14222
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.7213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0524
_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)+(0.0667P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                2738
_reflns_number_total             5621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062912xsi20061229_041259.cif
_cod_data_source_block           ll1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505285
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
C201 C 0.1602(2) 0.43292(18) 0.56231(19) 0.0478(7) Uani 1 1 d . . .
H20A H 0.0913 0.4207 0.5927 0.057 Uiso 1 1 calc R . .
H20B H 0.2253 0.3942 0.5944 0.057 Uiso 1 1 calc R . .
O202 O 0.18954(14) 0.53051(11) 0.56910(12) 0.0448(5) Uani 1 1 d . . .
C203 C 0.2088(2) 0.56304(18) 0.66362(18) 0.0462(7) Uani 1 1 d . . .
H20F H 0.2691 0.5236 0.7012 0.055 Uiso 1 1 calc R . .
H20G H 0.1365 0.5569 0.6909 0.055 Uiso 1 1 calc R . .
C204 C 0.2466(2) 0.66377(17) 0.66758(18) 0.0421(6) Uani 1 1 d . . .
H20D H 0.1993 0.6999 0.6165 0.050 Uiso 1 1 calc R . .
H20E H 0.2347 0.6919 0.7282 0.050 Uiso 1 1 calc R . .
O205 O 0.36781(13) 0.67039(11) 0.65791(12) 0.0421(4) Uani 1 1 d . . .
C206 C 0.4137(2) 0.75998(17) 0.67074(17) 0.0371(6) Uani 1 1 d . . .
C207 C 0.3486(2) 0.84061(18) 0.67603(18) 0.0446(7) Uani 1 1 d . . .
H20C H 0.2667 0.8358 0.6705 0.054 Uiso 1 1 calc R . .
C208 C 0.4010(2) 0.92868(19) 0.68936(19) 0.0493(7) Uani 1 1 d . . .
H20H H 0.3549 0.9837 0.6923 0.059 Uiso 1 1 calc R . .
C209 C 0.5183(2) 0.93666(19) 0.69822(19) 0.0497(7) Uani 1 1 d . . .
H20I H 0.5539 0.9971 0.7085 0.060 Uiso 1 1 calc R . .
C210 C 0.5859(2) 0.85717(17) 0.69228(19) 0.0451(7) Uani 1 1 d . . .
H21G H 0.6677 0.8633 0.6985 0.054 Uiso 1 1 calc R . .
C211 C 0.5350(2) 0.76840(17) 0.67722(16) 0.0371(6) Uani 1 1 d . . .
O212 O 0.59591(13) 0.68641(11) 0.66893(12) 0.0429(4) Uani 1 1 d . . .
C213 C 0.7210(2) 0.69681(17) 0.68408(18) 0.0397(6) Uani 1 1 d . . .
H21C H 0.7476 0.7239 0.7471 0.048 Uiso 1 1 calc R . .
H21D H 0.7445 0.7404 0.6366 0.048 Uiso 1 1 calc R . .
C214 C 0.7750(2) 0.60174(17) 0.67631(18) 0.0439(6) Uani 1 1 d . . .
H21A H 0.8579 0.6048 0.7043 0.053 Uiso 1 1 calc R . .
H21B H 0.7368 0.5550 0.7126 0.053 Uiso 1 1 calc R . .
O215 O 0.76534(13) 0.57023(11) 0.58040(12) 0.0418(4) Uani 1 1 d . . .
C216 C 0.8649(2) 0.59255(18) 0.53925(19) 0.0459(7) Uani 1 1 d . . .
H21E H 0.9328 0.5564 0.5706 0.055 Uiso 1 1 calc R . .
H21F H 0.8827 0.6610 0.5465 0.055 Uiso 1 1 calc R . .
Cl1 Cl 0.00815(6) 0.36379(5) 0.79467(5) 0.0517(2) Uani 1 1 d D . .
O1 O 0.1134(2) 0.41221(16) 0.82537(18) 0.0925(8) Uani 1 1 d D A .
O2 O -0.0375(5) 0.3300(7) 0.8732(2) 0.123(3) Uani 0.831(15) 1 d P A 1
O3 O -0.0747(5) 0.4183(3) 0.7356(5) 0.1076(16) Uani 0.831(15) 1 d P A 1
O4 O 0.0384(5) 0.2850(4) 0.7409(6) 0.115(3) Uani 0.831(15) 1 d P A 1
O2A O -0.0619(11) 0.3887(14) 0.8636(11) 0.066(6) Uiso 0.169(15) 1 d PD A 2
O3A O -0.0470(16) 0.4068(12) 0.7106(9) 0.055(6) Uiso 0.169(15) 1 d PD A 2
O4A O 0.0123(11) 0.2703(9) 0.7878(13) 0.048(5) Uiso 0.169(15) 1 d PD A 2
N101 N 0.48490(17) 0.69806(14) 0.44022(15) 0.0397(5) Uani 1 1 d D . .
H101 H 0.5566(15) 0.7114(18) 0.4463(19) 0.060 Uiso 1 1 d D . .
C102 C 0.3984(2) 0.76588(17) 0.43257(16) 0.0374(6) Uani 1 1 d . . .
C103 C 0.4027(2) 0.86419(18) 0.43157(18) 0.0490(7) Uani 1 1 d . . .
H10A H 0.4740 0.8976 0.4367 0.059 Uiso 1 1 calc R . .
C104 C 0.2978(3) 0.91056(19) 0.4227(2) 0.0554(8) Uani 1 1 d . . .
H10B H 0.2965 0.9778 0.4208 0.066 Uiso 1 1 calc R . .
C105 C 0.1940(3) 0.8615(2) 0.4164(2) 0.0564(8) Uani 1 1 d . . .
H10C H 0.1237 0.8964 0.4103 0.068 Uiso 1 1 calc R . .
C106 C 0.1892(2) 0.76369(19) 0.41863(18) 0.0477(7) Uani 1 1 d . . .
H10E H 0.1179 0.7306 0.4151 0.057 Uiso 1 1 calc R . .
C107 C 0.2943(2) 0.71666(17) 0.42627(16) 0.0376(6) Uani 1 1 d . . .
N108 N 0.32371(18) 0.62143(14) 0.43044(14) 0.0392(5) Uani 1 1 d D . .
H108 H 0.277(2) 0.5738(16) 0.4355(19) 0.066(9) Uiso 1 1 d D . .
C109 C 0.4383(2) 0.61184(17) 0.43905(16) 0.0370(6) Uani 1 1 d . . .
C110 C 0.5032(2) 0.52139(16) 0.45149(17) 0.0395(6) Uani 1 1 d . . .
H11B H 0.5852 0.5327 0.4451 0.047 Uiso 1 1 calc R . .
H11A H 0.4701 0.4762 0.4020 0.047 Uiso 1 1 calc R . .
N01 N 0.7027(2) 0.80120(18) 0.4454(2) 0.0687(7) Uani 1 1 d . . .
C02 C 0.7770(3) 0.8504(2) 0.4408(2) 0.0563(8) Uani 1 1 d . . .
C03 C 0.8735(3) 0.9132(3) 0.4338(2) 0.0956(13) Uani 1 1 d . . .
H03C H 0.9204 0.9209 0.4959 0.115 Uiso 1 1 calc R . .
H03B H 0.8439 0.9751 0.4102 0.115 Uiso 1 1 calc R . .
H03A H 0.9214 0.8860 0.3904 0.115 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'
O O 0.0106 0.0060 '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'
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
O202 C201 C216 108.0(2) . 3_666
O202 C201 H20A 110.1 . .
C216 C201 H20A 110.1 3_666 .
O202 C201 H20B 110.1 . .
C216 C201 H20B 110.1 3_666 .
H20A C201 H20B 108.4 . .
C201 O202 C203 112.31(19) . .
O202 C203 C204 110.3(2) . .
O202 C203 H20F 109.6 . .
C204 C203 H20F 109.6 . .
O202 C203 H20G 109.6 . .
C204 C203 H20G 109.6 . .
H20F C203 H20G 108.1 . .
O205 C204 C203 110.3(2) . .
O205 C204 H20D 109.6 . .
C203 C204 H20D 109.6 . .
O205 C204 H20E 109.6 . .
C203 C204 H20E 109.6 . .
H20D C204 H20E 108.1 . .
C206 O205 C204 114.42(18) . .
O205 C206 C207 124.0(2) . .
O205 C206 C211 117.0(2) . .
C207 C206 C211 119.0(2) . .
C206 C207 C208 120.8(2) . .
C206 C207 H20C 119.6 . .
C208 C207 H20C 119.6 . .
C209 C208 C207 120.3(2) . .
C209 C208 H20H 119.9 . .
C207 C208 H20H 119.9 . .
C208 C209 C210 120.2(2) . .
C208 C209 H20I 119.9 . .
C210 C209 H20I 119.9 . .
C209 C210 C211 120.5(2) . .
C209 C210 H21G 119.8 . .
C211 C210 H21G 119.8 . .
O212 C211 C210 123.9(2) . .
O212 C211 C206 116.9(2) . .
C210 C211 C206 119.2(2) . .
C211 O212 C213 115.17(17) . .
O212 C213 C214 108.95(19) . .
O212 C213 H21C 109.9 . .
C214 C213 H21C 109.9 . .
O212 C213 H21D 109.9 . .
C214 C213 H21D 109.9 . .
H21C C213 H21D 108.3 . .
O215 C214 C213 112.3(2) . .
O215 C214 H21A 109.1 . .
C213 C214 H21A 109.1 . .
O215 C214 H21B 109.1 . .
C213 C214 H21B 109.1 . .
H21A C214 H21B 107.9 . .
C216 O215 C214 112.74(17) . .
O215 C216 C201 107.96(19) . 3_666
O215 C216 H21E 110.1 . .
C201 C216 H21E 110.1 3_666 .
O215 C216 H21F 110.1 . .
C201 C216 H21F 110.1 3_666 .
H21E C216 H21F 108.4 . .
O4A Cl1 O2 75.2(6) . .
O4A Cl1 O3 121.8(7) . .
O2 Cl1 O3 111.1(3) . .
O4A Cl1 O1 117.7(6) . .
O2 Cl1 O1 109.42(18) . .
O3 Cl1 O1 113.9(2) . .
O4A Cl1 O3A 112.3(8) . .
O2 Cl1 O3A 130.8(7) . .
O3 Cl1 O3A 22.2(7) . .
O1 Cl1 O3A 108.5(6) . .
O4A Cl1 O2A 109.2(7) . .
O2 Cl1 O2A 36.2(6) . .
O3 Cl1 O2A 82.7(6) . .
O1 Cl1 O2A 103.2(6) . .
O3A Cl1 O2A 104.9(7) . .
O4A Cl1 O4 33.9(5) . .
O2 Cl1 O4 109.2(3) . .
O3 Cl1 O4 107.5(2) . .
O1 Cl1 O4 105.6(3) . .
O3A Cl1 O4 89.3(7) . .
O2A Cl1 O4 141.8(6) . .
C109 N101 C102 109.8(2) . .
C109 N101 H101 126.7(19) . .
C102 N101 H101 123.4(19) . .
N101 C102 C103 131.7(2) . .
N101 C102 C107 106.3(2) . .
C103 C102 C107 122.1(2) . .
C104 C103 C102 116.3(2) . .
C104 C103 H10A 121.9 . .
C102 C103 H10A 121.9 . .
C103 C104 C105 121.7(3) . .
C103 C104 H10B 119.2 . .
C105 C104 H10B 119.2 . .
C106 C105 C104 122.4(3) . .
C106 C105 H10C 118.8 . .
C104 C105 H10C 118.8 . .
C105 C106 C107 116.3(2) . .
C105 C106 H10E 121.9 . .
C107 C106 H10E 121.9 . .
C106 C107 N108 132.8(2) . .
C106 C107 C102 121.4(2) . .
N108 C107 C102 105.8(2) . .
C109 N108 C107 110.0(2) . .
C109 N108 H108 123.2(19) . .
C107 N108 H108 126.2(19) . .
N101 C109 N108 108.1(2) . .
N101 C109 C110 125.9(2) . .
N108 C109 C110 125.9(2) . .
C109 C110 C110 110.6(2) . 3_666
C109 C110 H11B 109.5 . .
C110 C110 H11B 109.5 3_666 .
C109 C110 H11A 109.5 . .
C110 C110 H11A 109.5 3_666 .
H11B C110 H11A 108.1 . .
N01 C02 C03 179.2(4) . .
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
C201 O202 1.419(3) .
C201 C216 1.491(3) 3_666
C201 H20A 0.9900 .
C201 H20B 0.9900 .
O202 C203 1.422(3) .
C203 C204 1.487(3) .
C203 H20F 0.9900 .
C203 H20G 0.9900 .
C204 O205 1.447(3) .
C204 H20D 0.9900 .
C204 H20E 0.9900 .
O205 C206 1.375(3) .
C206 C207 1.378(3) .
C206 C211 1.409(3) .
C207 C208 1.386(4) .
C207 H20C 0.9500 .
C208 C209 1.360(4) .
C208 H20H 0.9500 .
C209 C210 1.382(4) .
C209 H20I 0.9500 .
C210 C211 1.389(3) .
C210 H21G 0.9500 .
C211 O212 1.374(3) .
O212 C213 1.451(3) .
C213 C214 1.494(3) .
C213 H21C 0.9900 .
C213 H21D 0.9900 .
C214 O215 1.440(3) .
C214 H21A 0.9900 .
C214 H21B 0.9900 .
O215 C216 1.422(3) .
C216 C201 1.491(3) 3_666
C216 H21E 0.9900 .
C216 H21F 0.9900 .
Cl1 O4A 1.325(13) .
Cl1 O2 1.408(3) .
Cl1 O3 1.412(3) .
Cl1 O1 1.415(2) .
Cl1 O3A 1.417(14) .
Cl1 O2A 1.427(13) .
Cl1 O4 1.431(4) .
N101 C109 1.332(3) .
N101 C102 1.383(3) .
N101 H101 0.849(17) .
C102 C103 1.388(3) .
C102 C107 1.392(3) .
C103 C104 1.378(4) .
C103 H10A 0.9500 .
C104 C105 1.386(4) .
C104 H10B 0.9500 .
C105 C106 1.382(4) .
C105 H10C 0.9500 .
C106 C107 1.384(3) .
C106 H10E 0.9500 .
C107 N108 1.386(3) .
N108 C109 1.332(3) .
N108 H108 0.879(17) .
C109 C110 1.481(3) .
C110 C110 1.536(5) 3_666
C110 H11B 0.9900 .
C110 H11A 0.9900 .
N01 C02 1.121(3) .
C02 C03 1.450(4) .
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 N01 0.849(17) 2.128(19) 2.922(3) 156(2) .
N108 H108 O202 0.879(17) 2.39(3) 3.014(3) 128(2) .
C110 H11B O215 0.99 2.69 3.394(3) 128.5 .
N108 H108 O215 0.879(17) 2.09(2) 2.893(3) 151(3) 3_666
C110 H11A O212 0.99 2.58 3.510(3) 156.6 3_666
C110 H11A O215 0.99 2.88 3.357(3) 110.7 3_666
C110 H11B O202 0.99 2.82 3.721(3) 152.3 3_666
C106 H10E O4 0.95 2.67 3.303(4) 124.2 3_566
