#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/64/2206463.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_2206463
loop_
_publ_author_name
'Yliana López'
'Rosa Santillan'
'M. Eugenia Ochoa'
'Norberto Farfán'
'Efrén V. García-Báez'
'Itzia I. Padilla-Martínez'
_publ_section_title
;
 1,1',3,3'-Tetrabenzyl-2,2'-biimidazolidine
;
_journal_coeditor_code           IS6094
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2464
_journal_page_last               o2466
_journal_paper_doi               10.1107/S1600536805021136
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C34 H38 N4'
_chemical_formula_moiety         'C34 H38 N4'
_chemical_formula_sum            'C34 H38 N4'
_chemical_formula_weight         502.68
_chemical_name_systematic
;
1,1',3,3'-Tetrabenzyl-2,2'-biimidazolidine
;
_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
_cell_angle_beta                 93.4210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.83840(10)
_cell_length_b                   9.6253(2)
_cell_length_c                   25.7216(4)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     1442.88(4)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4969
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         4.23
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0482
_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)+(0.0668P)²+0.1647P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                2262
_reflns_number_total             3185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6094.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206463
_cod_database_fobs_code          2206463
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+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_thermal_displace_type
_atom_site_occupancy
_atom_site_type_symbol
N1 1.04063(19) 0.40326(11) 0.06374(4) 0.0564(4) Uani 1.000 N
N2 0.88401(19) 0.32282(10) -0.01848(4) 0.0560(4) Uani 1.000 N
C1 1.0966(3) 0.25582(15) 0.05534(5) 0.0726(6) Uani 1.000 C
C2 0.9154(3) 0.20451(15) 0.01646(6) 0.0749(6) Uani 1.000 C
C3 0.9255(2) 0.44887(13) 0.01398(5) 0.0544(4) Uani 1.000 C
C4 0.6618(2) 0.32237(15) -0.04776(6) 0.0662(5) Uani 1.000 C
C5 0.6365(2) 0.20049(14) -0.08443(5) 0.0602(5) Uani 1.000 C
C6 0.4453(3) 0.11588(18) -0.08482(6) 0.0763(6) Uani 1.000 C
C7 0.4219(3) 0.0047(2) -0.11832(6) 0.0833(6) Uani 1.000 C
C8 0.5887(3) -0.02533(16) -0.15198(6) 0.0729(5) Uani 1.000 C
C9 0.7787(3) 0.05820(16) -0.15233(6) 0.0742(5) Uani 1.000 C
C10 0.8016(3) 0.17010(16) -0.11901(7) 0.0721(6) Uani 1.000 C
C11 0.8997(3) 0.42454(17) 0.10822(5) 0.0665(5) Uani 1.000 C
C12 1.0251(3) 0.38645(15) 0.15938(5) 0.0630(5) Uani 1.000 C
C13 0.9354(3) 0.29056(19) 0.19243(6) 0.0805(6) Uani 1.000 C
C14 1.0523(4) 0.2546(2) 0.23927(6) 0.0961(8) Uani 1.000 C
C15 1.2567(4) 0.3158(2) 0.25372(7) 0.0941(8) Uani 1.000 C
C16 1.3470(3) 0.4111(2) 0.22160(7) 0.0909(7) Uani 1.000 C
C17 1.2336(3) 0.44596(19) 0.17477(6) 0.0787(6) Uani 1.000 C
H1A 1.24763 0.24666 0.04191 0.0871 Uiso 1.000 H
H1B 1.09343 0.20399 0.08763 0.0871 Uiso 1.000 H
H2A 0.77479 0.18235 0.03296 0.0898 Uiso 1.000 H
H2B 0.96681 0.12316 -0.00181 0.0898 Uiso 1.000 H
H3A 0.77860 0.49270 0.02062 0.0653 Uiso 1.000 H
H4A 0.54068 0.31920 -0.02357 0.0794 Uiso 1.000 H
H4B 0.64474 0.40789 -0.06756 0.0794 Uiso 1.000 H
H6 0.33093 0.13429 -0.06212 0.0915 Uiso 1.000 H
H7 0.29150 -0.05069 -0.11817 0.1000 Uiso 1.000 H
H8 0.57313 -0.10134 -0.17423 0.0874 Uiso 1.000 H
H9 0.89248 0.03932 -0.17513 0.0890 Uiso 1.000 H
H10 0.93085 0.22632 -0.11982 0.0865 Uiso 1.000 H
H11A 0.85367 0.52127 0.10934 0.0798 Uiso 1.000 H
H11B 0.76183 0.36862 0.10358 0.0798 Uiso 1.000 H
H13 0.79470 0.24927 0.18330 0.0966 Uiso 1.000 H
H14 0.99062 0.18853 0.26079 0.1153 Uiso 1.000 H
H15 1.33380 0.29273 0.28521 0.1128 Uiso 1.000 H
H16 1.48642 0.45318 0.23131 0.1091 Uiso 1.000 H
H17 1.29869 0.51063 0.15320 0.0945 Uiso 1.000 H
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'
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C3 . . 104.62(10) yes
C1 N1 C11 . . 112.90(11) yes
C3 N1 C11 . . 112.84(11) yes
C2 N2 C3 . . 106.37(10) yes
C2 N2 C4 . . 113.03(11) yes
C3 N2 C4 . . 113.73(10) yes
N1 C1 C2 . . 105.16(12) yes
N2 C2 C1 . . 102.27(11) yes
N1 C3 N2 . . 107.16(10) yes
N1 C3 C3 . 3_765 111.00(10) yes
N2 C3 C3 . 3_765 109.96(10) yes
N2 C4 C5 . . 112.08(10) yes
C4 C5 C6 . . 120.83(12) no
C4 C5 C10 . . 121.45(12) no
C6 C5 C10 . . 117.72(13) no
C5 C6 C7 . . 120.88(15) no
C6 C7 C8 . . 120.76(16) no
C7 C8 C9 . . 119.07(15) no
C8 C9 C10 . . 120.20(16) no
C5 C10 C9 . . 121.36(15) no
N1 C11 C12 . . 112.39(13) yes
C11 C12 C13 . . 121.11(15) no
C11 C12 C17 . . 121.42(14) no
C13 C12 C17 . . 117.47(14) no
C12 C13 C14 . . 121.01(17) no
C13 C14 C15 . . 120.31(17) no
C14 C15 C16 . . 119.36(17) no
C15 C16 C17 . . 120.67(17) no
C12 C17 C16 . . 121.17(16) no
N1 C1 H1A . . 110.71 no
N1 C1 H1B . . 110.71 no
C2 C1 H1A . . 110.71 no
C2 C1 H1B . . 110.72 no
H1A C1 H1B . . 108.81 no
N2 C2 H2A . . 111.31 no
N2 C2 H2B . . 111.32 no
C1 C2 H2A . . 111.31 no
C1 C2 H2B . . 111.32 no
H2A C2 H2B . . 109.20 no
N1 C3 H3A . . 109.56 no
N2 C3 H3A . . 109.56 no
C3 C3 H3A 3_765 . 109.56 no
N2 C4 H4A . . 109.18 no
N2 C4 H4B . . 109.17 no
C5 C4 H4A . . 109.21 no
C5 C4 H4B . . 109.20 no
H4A C4 H4B . . 107.91 no
C5 C6 H6 . . 119.56 no
C7 C6 H6 . . 119.56 no
C6 C7 H7 . . 119.62 no
C8 C7 H7 . . 119.61 no
C7 C8 H8 . . 120.47 no
C9 C8 H8 . . 120.46 no
C8 C9 H9 . . 119.90 no
C10 C9 H9 . . 119.90 no
C5 C10 H10 . . 119.32 no
C9 C10 H10 . . 119.32 no
N1 C11 H11A . . 109.11 no
N1 C11 H11B . . 109.12 no
C12 C11 H11A . . 109.11 no
C12 C11 H11B . . 109.13 no
H11A C11 H11B . . 107.88 no
C12 C13 H13 . . 119.51 no
C14 C13 H13 . . 119.49 no
C13 C14 H14 . . 119.86 no
C15 C14 H14 . . 119.83 no
C14 C15 H15 . . 120.33 no
C16 C15 H15 . . 120.31 no
C15 C16 H16 . . 119.66 no
C17 C16 H16 . . 119.66 no
C12 C17 H17 . . 119.40 no
C16 C17 H17 . . 119.43 no
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
N1 C1 . 1.4751(18) yes
N1 C3 . 1.4765(16) yes
N1 C11 . 1.4630(18) yes
N2 C2 . 1.4555(18) yes
N2 C3 . 1.4845(16) yes
N2 C4 . 1.4607(17) yes
C1 C2 . 1.496(2) no
C3 C3 3_765 1.5223(17) no
C4 C5 . 1.507(2) no
C5 C6 . 1.381(2) no
C5 C10 . 1.381(2) no
C6 C7 . 1.376(2) no
C7 C8 . 1.372(2) no
C8 C9 . 1.370(2) no
C9 C10 . 1.378(2) no
C11 C12 . 1.512(2) no
C12 C13 . 1.379(2) no
C12 C17 . 1.382(2) no
C13 C14 . 1.392(2) no
C14 C15 . 1.362(3) no
C15 C16 . 1.362(3) no
C16 C17 . 1.381(2) no
C1 H1A . 0.9700 no
C1 H1B . 0.9700 no
C2 H2A . 0.9701 no
C2 H2B . 0.9700 no
C3 H3A . 0.9799 no
C4 H4A . 0.9699 no
C4 H4B . 0.9700 no
C6 H6 . 0.9299 no
C7 H7 . 0.9296 no
C8 H8 . 0.9300 no
C9 H9 . 0.9299 no
C10 H10 . 0.9298 no
C11 H11A . 0.9700 no
C11 H11B . 0.9698 no
C13 H13 . 0.9300 no
C14 H14 . 0.9297 no
C15 H15 . 0.9298 no
C16 H16 . 0.9299 no
C17 H17 . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 N2 2.9260(14) 3_765 no
N1 C4 3.2011(17) 3_765 no
N2 N1 2.9260(14) 3_765 no
N1 H17 2.8669 . no
N1 H4B 2.5820 3_765 no
N2 H10 2.7959 . no
C2 C10 3.524(2) . no
C4 N1 3.2011(17) 3_765 no
C10 C2 3.524(2) . no
C2 H11B 2.9258 . no
C5 H2A 3.0836 . no
C5 H2B 2.8810 . no
C8 H15 3.0904 4_454 no
C8 H1B 2.9622 3_755 no
C9 H1B 3.0899 3_755 no
C11 H2A 3.0895 . no
C12 H1B 2.5956 . no
C13 H1B 3.0181 . no
H1A H4A 2.5682 1_655 no
H1B C12 2.5956 . no
H1B C13 3.0181 . no
H1B H11B 2.5539 . no
H1B C8 2.9622 3_755 no
H1B C9 3.0899 3_755 no
H2A C5 3.0836 . no
H2A C11 3.0895 . no
H2A H4A 2.3410 . no
H2A H11B 2.5566 . no
H2A H7 2.5808 3_655 no
H2B C5 2.8810 . no
H2B H2B 2.4033 3_755 no
H3A H4A 2.4129 . no
H3A H4B 2.4920 . no
H3A H11A 2.3143 . no
H3A H11B 2.4524 . no
H4A H1A 2.5682 1_455 no
H4A H2A 2.3410 . no
H4A H3A 2.4129 . no
H4A H6 2.3464 . no
H4B H3A 2.4920 . no
H4B N1 2.5820 3_765 no
H4B H17 2.3798 3_765 no
H6 H4A 2.3464 . no
H7 H2A 2.5808 3_655 no
H7 H13 2.5715 3_655 no
H8 H13 2.5756 3_655 no
H10 N2 2.7959 . no
H11A H3A 2.3143 . no
H11B C2 2.9258 . no
H11B H1B 2.5539 . no
H11B H2A 2.5566 . no
H11B H3A 2.4524 . no
H11B H13 2.3482 . no
H13 H11B 2.3482 . no
H13 H7 2.5715 3_655 no
H13 H8 2.5756 3_655 no
H15 C8 3.0904 4_655 no
H17 N1 2.8669 . no
H17 H4B 2.3798 3_765 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4B N1 3_765 0.97 2.58 3.2011(17) 122 yes
C8 H8 Cg1 3_755 0.93 3.07 3.8140(18) 139 yes
C15 H15 Cg2 4_655 0.93 3.10 3.894(2) 144 yes
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C1 C2 . . -29.26(14) no
C11 N1 C1 C2 . . 93.80(13) no
C1 N1 C3 N2 . . 9.03(13) no
C11 N1 C3 N2 . . -114.08(12) no
C1 N1 C3 C3 . 3_765 -111.06(12) no
C11 N1 C3 C3 . 3_765 125.84(12) no
C3 N1 C11 C12 . . -176.18(11) no
C1 N1 C11 C12 . . 65.45(16) no
C4 N2 C2 C1 . . -157.97(12) no
C3 N2 C2 C1 . . -32.47(14) no
C4 N2 C3 N1 . . 140.17(10) no
C2 N2 C4 C5 . . -64.61(15) no
C2 N2 C3 N1 . . 15.09(13) no
C2 N2 C3 C3 . 3_765 135.84(11) no
C4 N2 C3 C3 . 3_765 -99.09(12) no
C3 N2 C4 C5 . . 173.95(10) no
N1 C1 C2 N2 . . 38.44(14) no
N2 C3 C3 N1 3_765 3_765 61.59(13) no
N2 C3 C3 N2 3_765 3_765 -179.98(13) no
N1 C3 C3 N2 3_765 3_765 -61.59(13) no
N1 C3 C3 N1 3_765 3_765 179.98(12) no
N2 C4 C5 C6 . . 129.43(14) no
N2 C4 C5 C10 . . -51.15(18) no
C4 C5 C6 C7 . . 179.92(15) no
C6 C5 C10 C9 . . -0.9(2) no
C10 C5 C6 C7 . . 0.5(2) no
C4 C5 C10 C9 . . 179.67(14) no
C5 C6 C7 C8 . . 0.4(3) no
C6 C7 C8 C9 . . -0.8(3) no
C7 C8 C9 C10 . . 0.4(2) no
C8 C9 C10 C5 . . 0.4(2) no
N1 C11 C12 C13 . . -124.08(16) no
N1 C11 C12 C17 . . 55.81(19) no
C17 C12 C13 C14 . . -0.6(3) no
C11 C12 C13 C14 . . 179.34(16) no
C11 C12 C17 C16 . . 179.80(16) no
C13 C12 C17 C16 . . -0.3(3) no
C12 C13 C14 C15 . . 1.2(3) no
C13 C14 C15 C16 . . -0.9(3) no
C14 C15 C16 C17 . . 0.0(3) no
C15 C16 C17 C12 . . 0.6(3) no
