#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/13/2201341.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_2201341
loop_
_publ_author_name
'Jian-Feng Li'
'Lin-Hong Weng'
'Shu-Ping Huang'
'Hong-Bo Tong'
'Jian-Ping Guo'
'Dian-Sheng Liu'
_publ_section_title
;
 (1R,2R)-({-})-1,2-Dibenzamidino-cyclohexane
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1078
_journal_page_last               o1080
_journal_paper_doi               10.1107/S1600536802016045
_journal_volume                  58
_journal_year                    2002
_chemical_formula_sum            'C20 H24 N4'
_chemical_formula_weight         320.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.696(5)
_cell_length_b                   8.698(5)
_cell_length_c                   22.806(13)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.45
_cell_measurement_theta_min      2.49
_cell_volume                     1725.0(17)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       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  0.0984
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7152
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         1773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0587
_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)+(0.0443P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                1505
_reflns_number_total             1773
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6198.cif
_cod_data_source_block           I
_cod_original_cell_volume        1725.1(17)
_cod_database_code               2201341
_cod_database_fobs_code          2201341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_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
C1 0.6641(4) 1.1146(5) -0.07579(17) 0.0281(10) Uani d . 1 . . C
H1A 0.6654 1.2138 -0.0952 0.034 Uiso calc R 1 . . H
H1B 0.7203 1.0422 -0.1000 0.034 Uiso calc R 1 . . H
C2 0.4994(5) 1.0606(5) -0.06898(17) 0.0296(10) Uani d . 1 . . C
H2A 0.4535 1.0475 -0.1074 0.036 Uiso calc R 1 . . H
H2B 0.4407 1.1379 -0.0480 0.036 Uiso calc R 1 . . H
C3 0.4926(5) 0.9086(4) -0.03554(16) 0.0262(10) Uani d . 1 . . C
H3A 0.5409 0.8288 -0.0588 0.031 Uiso calc R 1 . . H
H3B 0.3860 0.8800 -0.0296 0.031 Uiso calc R 1 . . H
C4 0.5733(4) 0.9190(4) 0.02394(17) 0.0245(9) Uani d . 1 . . C
H4A 0.5186 0.9948 0.0479 0.029 Uiso calc R 1 . . H
C5 0.7401(4) 0.9739(4) 0.01648(16) 0.0240(9) Uani d . 1 . . C
H5A 0.7963 0.8976 -0.0068 0.029 Uiso calc R 1 . . H
C6 0.7416(5) 1.1278(4) -0.01648(16) 0.0260(9) Uani d . 1 . . C
H6A 0.6890 1.2049 0.0068 0.031 Uiso calc R 1 . . H
H6B 0.8471 1.1612 -0.0218 0.031 Uiso calc R 1 . . H
C7 0.5489(4) 0.7581(5) 0.11289(17) 0.0258(10) Uani d . 1 . . C
C8 0.5178(4) 0.5991(5) 0.13581(16) 0.0247(9) Uani d . 1 . . C
C9 0.4193(4) 0.5804(5) 0.18368(18) 0.0289(10) Uani d . 1 . . C
H9A 0.3752 0.6662 0.2013 0.035 Uiso calc R 1 . . H
C10 0.3867(5) 0.4353(5) 0.20511(18) 0.0324(11) Uani d . 1 . . C
H10A 0.3180 0.4235 0.2360 0.039 Uiso calc R 1 . . H
C11 0.4564(5) 0.3077(5) 0.18059(19) 0.0362(11) Uani d . 1 . . C
H11A 0.4358 0.2102 0.1954 0.043 Uiso calc R 1 . . H
C12 0.5573(5) 0.3254(5) 0.13381(18) 0.0327(11) Uani d . 1 . . C
H12A 0.6054 0.2398 0.1176 0.039 Uiso calc R 1 . . H
C13 0.5862(4) 0.4699(5) 0.11131(17) 0.0267(10) Uani d . 1 . . C
H13A 0.6521 0.4808 0.0795 0.032 Uiso calc R 1 . . H
C14 0.9680(4) 0.9955(4) 0.08144(17) 0.0234(9) Uani d . 1 . . C
C15 1.0205(4) 1.0202(4) 0.14344(16) 0.0214(9) Uani d . 1 . . C
C16 1.1602(4) 0.9610(5) 0.16201(17) 0.0296(10) Uani d . 1 . . C
H16A 1.2196 0.9029 0.1363 0.036 Uiso calc R 1 . . H
C17 1.2127(5) 0.9880(5) 0.21909(17) 0.0315(10) Uani d . 1 . . C
H17A 1.3063 0.9471 0.2311 0.038 Uiso calc R 1 . . H
C18 1.1274(5) 1.0740(5) 0.25730(19) 0.0331(11) Uani d . 1 . . C
H18A 1.1636 1.0926 0.2950 0.040 Uiso calc R 1 . . H
C19 0.9872(5) 1.1334(5) 0.23974(19) 0.0392(12) Uani d . 1 . . C
H19A 0.9283 1.1909 0.2658 0.047 Uiso calc R 1 . . H
C20 0.9349(4) 1.1068(5) 0.18318(18) 0.0323(10) Uani d . 1 . . C
H20A 0.8408 1.1475 0.1716 0.039 Uiso calc R 1 . . H
N1 0.8139(4) 0.9876(4) 0.07407(15) 0.0254(8) Uani d . 1 . . N
N2 0.5649(4) 0.7690(4) 0.05406(15) 0.0256(8) Uani d . 1 . . N
N3 1.0598(4) 0.9847(4) 0.03657(15) 0.0275(8) Uani d . 1 . . N
N4 0.5610(4) 0.8788(4) 0.14562(16) 0.0290(8) Uani d . 1 . . N
H1 0.760(4) 0.974(4) 0.1038(15) 0.016(10) Uiso d . 1 . . H
H2 0.557(5) 0.687(5) 0.0293(19) 0.054(15) Uiso d . 1 . . H
H6 0.547(4) 0.855(4) 0.1835(17) 0.022(11) Uiso d . 1 . . H
H4 1.147(5) 1.005(6) 0.051(2) 0.063(18) Uiso d . 1 . . 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 0.0000 '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 0.0000 '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
_geom_angle_publ_flag
C2 C1 C6 110.7(3) ?
C2 C1 H1A 109.5 ?
C6 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
C6 C1 H1B 109.5 ?
H1A C1 H1B 108.1 ?
C1 C2 C3 110.9(3) ?
C1 C2 H2A 109.5 ?
C3 C2 H2A 109.5 ?
C1 C2 H2B 109.5 ?
C3 C2 H2B 109.5 ?
H2A C2 H2B 108.1 ?
C2 C3 C4 112.0(3) ?
C2 C3 H3A 109.2 ?
C4 C3 H3A 109.2 ?
C2 C3 H3B 109.2 ?
C4 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
N2 C4 C3 109.8(3) ?
N2 C4 C5 111.9(3) yes
C3 C4 C5 110.7(3) ?
N2 C4 H4A 108.1 ?
C3 C4 H4A 108.1 ?
C5 C4 H4A 108.1 ?
N1 C5 C6 111.3(3) ?
N1 C5 C4 109.8(3) yes
C6 C5 C4 109.5(3) ?
N1 C5 H5A 108.7 ?
C6 C5 H5A 108.7 ?
C4 C5 H5A 108.7 ?
C1 C6 C5 111.5(3) ?
C1 C6 H6A 109.3 ?
C5 C6 H6A 109.3 ?
C1 C6 H6B 109.3 ?
C5 C6 H6B 109.3 ?
H6A C6 H6B 108.0 ?
N4 C7 N2 120.5(4) yes
N4 C7 C8 124.2(4) yes
N2 C7 C8 115.4(3) yes
C13 C8 C9 118.9(4) ?
C13 C8 C7 121.9(3) ?
C9 C8 C7 119.3(3) ?
C10 C9 C8 120.5(4) ?
C10 C9 H9A 119.7 ?
C8 C9 H9A 119.7 ?
C11 C10 C9 120.0(4) ?
C11 C10 H10A 120.0 ?
C9 C10 H10A 120.0 ?
C10 C11 C12 119.9(4) ?
C10 C11 H11A 120.0 ?
C12 C11 H11A 120.0 ?
C13 C12 C11 120.1(4) ?
C13 C12 H12A 120.0 ?
C11 C12 H12A 120.0 ?
C12 C13 C8 120.6(4) ?
C12 C13 H13A 119.7 ?
C8 C13 H13A 119.7 ?
N3 C14 N1 120.4(4) yes
N3 C14 C15 124.3(4) yes
N1 C14 C15 115.2(3) yes
C16 C15 C20 118.1(4) ?
C16 C15 C14 120.1(3) ?
C20 C15 C14 121.8(3) ?
C15 C16 C17 120.5(4) ?
C15 C16 H16A 119.7 ?
C17 C16 H16A 119.7 ?
C18 C17 C16 120.5(4) ?
C18 C17 H17A 119.7 ?
C16 C17 H17A 119.7 ?
C17 C18 C19 119.9(4) ?
C17 C18 H18A 120.1 ?
C19 C18 H18A 120.1 ?
C18 C19 C20 119.8(4) ?
C18 C19 H19A 120.1 ?
C20 C19 H19A 120.1 ?
C19 C20 C15 121.3(4) ?
C19 C20 H20A 119.4 ?
C15 C20 H20A 119.4 ?
C14 N1 C5 123.3(3) yes
C14 N1 H1 118(3) ?
C5 N1 H1 118(3) ?
C7 N2 C4 121.9(3) yes
C7 N2 H2 124(3) ?
C4 N2 H2 114(3) ?
C14 N3 H4 103(3) ?
C7 N4 H6 111(2) ?
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
C1 C2 . 1.515(5) ?
C1 C6 . 1.516(5) ?
C1 H1A . 0.970 ?
C1 H1B . 0.970 ?
C2 C3 . 1.527(5) ?
C2 H2A . 0.970 ?
C2 H2B . 0.970 ?
C3 C4 . 1.530(5) ?
C3 H3A . 0.970 ?
C3 H3B . 0.970 ?
C4 N2 . 1.476(5) yes
C4 C5 . 1.537(5) yes
C4 H4A . 0.980 ?
C5 N1 . 1.467(5) yes
C5 C6 . 1.536(5) ?
C5 H5A . 0.980 ?
C6 H6A . 0.970 ?
C6 H6B . 0.970 ?
C7 N4 . 1.293(5) yes
C7 N2 . 1.352(5) yes
C7 C8 . 1.503(6) yes
C8 C13 . 1.389(5) ?
C8 C9 . 1.397(5) ?
C9 C10 . 1.383(5) ?
C9 H9A . 0.930 ?
C10 C11 . 1.382(6) ?
C10 H10A . 0.930 ?
C11 C12 . 1.390(6) ?
C11 H11A . 0.930 ?
C12 C13 . 1.381(5) ?
C12 H12A . 0.930 ?
C13 H13A . 0.930 ?
C14 N3 . 1.301(5) yes
C14 N1 . 1.352(5) yes
C14 C15 . 1.501(5) yes
C15 C16 . 1.386(5) ?
C15 C20 . 1.394(5) ?
C16 C17 . 1.399(5) ?
C16 H16A . 0.930 ?
C17 C18 . 1.367(6) ?
C17 H17A . 0.930 ?
C18 C19 . 1.383(6) ?
C18 H18A . 0.930 ?
C19 C20 . 1.387(6) ?
C19 H19A . 0.930 ?
C20 H20A . 0.930 ?
N1 H1 . 0.83(4) ?
N2 H2 . 0.91(4) ?
N3 H4 . 0.85(4) ?
N4 H6 . 0.90(4) ?
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
N2 H2 N3 4_465 0.91(4) 2.12(5) 3.024(5) 172(4) yes
N1 H1 N4 . 0.83(4) 2.14(4) 2.898(5) 151(3) 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
_geom_torsion_publ_flag
C6 C1 C2 C3 -56.1(4) ?
C1 C2 C3 C4 55.4(4) ?
C2 C3 C4 N2 -179.6(3) ?
C2 C3 C4 C5 -55.5(4) ?
N2 C4 C5 N1 -58.8(4) yes
C3 C4 C5 N1 178.4(3) ?
N2 C4 C5 C6 178.6(3) ?
C3 C4 C5 C6 55.8(4) ?
C2 C1 C6 C5 58.1(4) ?
N1 C5 C6 C1 -179.4(3) ?
C4 C5 C6 C1 -57.7(4) ?
N4 C7 C8 C13 -142.5(4) ?
N2 C7 C8 C13 37.2(5) ?
N4 C7 C8 C9 36.5(5) ?
N2 C7 C8 C9 -143.8(3) ?
C13 C8 C9 C10 -2.0(5) ?
C7 C8 C9 C10 178.9(3) ?
C8 C9 C10 C11 2.5(5) ?
C9 C10 C11 C12 -1.0(6) ?
C10 C11 C12 C13 -1.0(6) ?
C11 C12 C13 C8 1.5(5) ?
C9 C8 C13 C12 0.0(5) ?
C7 C8 C13 C12 179.1(3) ?
N3 C14 C15 C16 -32.1(5) ?
N1 C14 C15 C16 149.3(3) ?
N3 C14 C15 C20 145.9(4) ?
N1 C14 C15 C20 -32.8(5) ?
C20 C15 C16 C17 -0.4(5) ?
C14 C15 C16 C17 177.6(3) ?
C15 C16 C17 C18 -0.1(5) ?
C16 C17 C18 C19 0.6(6) ?
C17 C18 C19 C20 -0.6(6) ?
C18 C19 C20 C15 0.1(6) ?
C16 C15 C20 C19 0.4(5) ?
C14 C15 C20 C19 -177.6(3) ?
N3 C14 N1 C5 -3.0(5) yes
C15 C14 N1 C5 175.8(3) yes
C4 C5 N1 C14 162.9(3) yes
C6 C5 N1 C14 -75.5(4) ?
N4 C7 N2 C4 -9.2(5) yes
C8 C7 N2 C4 171.1(3) yes
C3 C4 N2 C7 -144.8(3) ?
C5 C4 N2 C7 92.1(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24731767
