#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/25/2012596.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012596
loop_
_publ_author_name
'Kaftory, Menahem'
'Shteiman, Vitaly'
'Botoshansky, Mark'
_publ_section_title
;Dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole]
 1-oxide and
 dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole]
 1,1''-dioxide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o183
_journal_page_last               o186
_journal_paper_doi               10.1107/S0108270102001099
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C18 H16 N4 O2'
_chemical_formula_moiety         'C18 H16 N4 O2'
_chemical_formula_sum            'C18 H16 N4 O2'
_chemical_formula_weight         320.34
_chemical_name_common            Magnet-5
_chemical_name_systematic
;
dispiro [2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole]
,1,1''-dioxide
;
_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                104.39(3)
_cell_angle_beta                 104.15(3)
_cell_angle_gamma                98.41(3)
_cell_formula_units_Z            1
_cell_length_a                   5.416(2)
_cell_length_b                   7.290(2)
_cell_length_c                   10.426(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.21
_cell_measurement_theta_min      3.09
_cell_volume                     377.1(2)
_computing_cell_refinement       'Philips PW1100/20 Software'
_computing_data_collection       'Philips PW1100/20 Software (Philips, 1973)'
_computing_data_reduction        'Philips PW1100/20 Software'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Philips PW1100'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0359
_diffrn_reflns_av_sigmaI/netI    .0669
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1422
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        7.3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             168
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .25
_refine_diff_density_max         .203
_refine_diff_density_min         -.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          .0936
_refine_ls_R_factor_gt           .0534
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0567P)²+0.0683P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1258
_refine_ls_wR_factor_ref         .1393
_reflns_number_gt                885
_reflns_number_total             1339
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            oa1128.cif
_cod_data_source_block           IV
_cod_database_code               2012596
_cod_database_fobs_code          2012596
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 -.0836(4) .7268(3) .3112(2) .0567(6) Uani d . 1 . . O
N1 .0766(4) .7937(3) .2539(2) .0381(6) Uani d . 1 . . N
N2 .2981(4) .8060(3) .0879(2) .0372(6) Uani d . 1 . . N
C1 .2504(5) .9603(4) .2994(3) .0362(6) Uani d . 1 . . C
C2 .3161(6) 1.1149(4) .4242(3) .0449(7) Uani d . 1 . . C
C3 .5157(6) 1.2607(4) .4436(3) .0517(8) Uani d . 1 . . C
C4 .6519(6) 1.2672(4) .3419(3) .0521(8) Uani d . 1 . . C
C5 .5908(6) 1.1253(4) .2206(3) .0470(8) Uani d . 1 . . C
C6 .3842(5) .9614(4) .1951(3) .0360(6) Uani d . 1 . . C
C7 .0962(5) .6816(4) .1158(3) .0338(6) Uani d . 1 . . C
C8 -.1671(5) .6423(4) .0080(3) .0399(7) Uani d . 1 . . C
C9 .1757(5) .4932(4) .1304(3) .0389(7) Uani d . 1 . . C
H2 .2249 1.1148 .4890 .066(10) Uiso calc R 1 . . H
H3 .5684 1.3616 .5259 .046(8) Uiso calc R 1 . . H
H4 .7873 1.3734 .3603 .045(8) Uiso calc R 1 . . H
H5 .6800 1.1335 .1557 .058(9) Uiso calc R 1 . . H
H81 -.3026 .5852 .0414 .054(8) Uiso calc R 1 . . H
H82 -.2026 .7643 -.0047 .051(8) Uiso calc R 1 . . H
H91 .3512 .5239 .1929 .033(6) Uiso calc R 1 . . H
H92 .0592 .4280 .1705 .044(8) Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .0637(14) .0596(13) .0520(13) .0013(10) .0365(11) .0136(10)
N1 .0409(13) .0416(13) .0351(12) .0062(10) .0198(11) .0104(10)
N2 .0371(12) .0403(13) .0360(12) .0063(10) .0140(10) .0124(10)
C1 .0406(15) .0363(15) .0325(14) .0104(12) .0103(12) .0112(11)
C2 .0604(19) .0427(17) .0342(16) .0166(15) .0159(14) .0107(13)
C3 .074(2) .0330(16) .0382(17) .0129(15) .0049(15) .0045(13)
C4 .0565(19) .0384(17) .0560(19) .0009(14) .0084(16) .0177(15)
C5 .0501(18) .0441(17) .0474(18) .0015(14) .0173(15) .0170(14)
C6 .0412(15) .0391(15) .0313(14) .0119(12) .0110(12) .0147(12)
C7 .0345(14) .0338(14) .0310(14) .0054(11) .0123(11) .0048(11)
C8 .0355(15) .0388(16) .0441(16) .0106(12) .0114(13) .0088(12)
C9 .0358(15) .0433(16) .0343(15) .0069(12) .0060(12) .0111(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 '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_site_symmetry_1
_geom_angle
O1 N1 C1 . 129.2(2)
O1 N1 C7 . 122.3(2)
C1 N1 C7 . 108.5(2)
C6 N2 C7 . 106.3(2)
N1 C1 C2 . 131.2(3)
N1 C1 C6 . 106.4(2)
C2 C1 C6 . 122.4(3)
C3 C2 C1 . 116.6(3)
C3 C2 H2 . 121.7
C1 C2 H2 . 121.7
C2 C3 C4 . 122.5(3)
C2 C3 H3 . 118.8
C4 C3 H3 . 118.8
C5 C4 C3 . 122.6(3)
C5 C4 H4 . 118.7
C3 C4 H4 . 118.7
C4 C5 C6 . 117.8(3)
C4 C5 H5 . 121.1
C6 C5 H5 . 121.1
N2 C6 C5 . 128.3(2)
N2 C6 C1 . 113.6(2)
C5 C6 C1 . 118.1(2)
N2 C7 N1 . 105.13(19)
N2 C7 C8 . 112.0(2)
N1 C7 C8 . 108.63(19)
N2 C7 C9 . 111.1(2)
N1 C7 C9 . 107.9(2)
C8 C7 C9 . 111.7(2)
C9 C8 C7 2_565 112.1(2)
C9 C8 H81 2_565 109.2
C7 C8 H81 . 109.2
C9 C8 H82 2_565 109.2
C7 C8 H82 . 109.2
H81 C8 H82 . 107.9
C8 C9 C7 2_565 112.0(2)
C8 C9 H91 2_565 109.2
C7 C9 H91 . 109.2
C8 C9 H92 2_565 109.2
C7 C9 H92 . 109.2
H91 C9 H92 . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.273(3) ?
N1 C1 . 1.322(3) ?
N1 C7 . 1.505(3) ?
N2 C6 . 1.308(3) ?
N2 C7 . 1.449(3) ?
C1 C2 . 1.420(4) ?
C1 C6 . 1.447(4) ?
C2 C3 . 1.337(4) ?
C2 H2 . .9300 ?
C3 C4 . 1.438(4) ?
C3 H3 . .9300 ?
C4 C5 . 1.351(4) ?
C4 H4 . .9300 ?
C5 C6 . 1.434(4) ?
C5 H5 . .9300 ?
C7 C8 . 1.522(4) ?
C7 C9 . 1.530(4) ?
C8 C9 2_565 1.518(3) ?
C8 H81 . .9700 ?
C8 H82 . .9700 ?
C9 C8 2_565 1.518(3) ?
C9 H91 . .9700 ?
C9 H92 . .9700 ?
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_site_symmetry_4
_geom_torsion
O1 N1 C1 C2 . .6(5)
C7 N1 C1 C2 . -178.3(3)
O1 N1 C1 C6 . 178.9(3)
C7 N1 C1 C6 . .1(3)
N1 C1 C2 C3 . 175.8(3)
C6 C1 C2 C3 . -2.3(4)
C1 C2 C3 C4 . 2.7(4)
C2 C3 C4 C5 . -1.1(5)
C3 C4 C5 C6 . -1.0(4)
C7 N2 C6 C5 . 177.5(3)
C7 N2 C6 C1 . -1.6(3)
C4 C5 C6 N2 . -177.8(3)
C4 C5 C6 C1 . 1.3(4)
N1 C1 C6 N2 . 1.0(3)
C2 C1 C6 N2 . 179.5(2)
N1 C1 C6 C5 . -178.2(2)
C2 C1 C6 C5 . .3(4)
C6 N2 C7 N1 . 1.5(3)
C6 N2 C7 C8 . 119.3(2)
C6 N2 C7 C9 . -115.0(2)
O1 N1 C7 N2 . -179.9(2)
C1 N1 C7 N2 . -1.0(3)
O1 N1 C7 C8 . 60.1(3)
C1 N1 C7 C8 . -121.0(2)
O1 N1 C7 C9 . -61.2(3)
C1 N1 C7 C9 . 117.7(2)
N2 C7 C8 C9 2_565 72.0(3)
N1 C7 C8 C9 2_565 -172.3(2)
C9 C7 C8 C9 2_565 -53.4(3)
N2 C7 C9 C8 2_565 -72.6(3)
N1 C7 C9 C8 2_565 172.7(2)
C8 C7 C9 C8 2_565 53.3(3)
