#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007271.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_2007271
loop_
_publ_author_name
'Li, W.-S.'
'Vatsadze, S. V.'
'Blake, A. J.'
'Mountford, P.'
_publ_section_title
;
 1,4-Bis(2-aminobenzyl)-1,4-diazacyclohexane
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9800019
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C18 H24 N4'
_chemical_formula_sum            'C18 H24 N4'
_chemical_formula_weight         296.41
_chemical_melting_point          ?
_chemical_name_systematic
;
 1,4-bis(2-aminobenzyl)-1,4-diazacyclohexane
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5694(15)
_cell_length_b                   8.917(2)
_cell_length_c                   13.696(3)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      17.35
_cell_measurement_theta_min      14.2
_cell_volume                     797.7(3)
_computing_cell_refinement       STADI-4
_computing_data_collection       'STADI-4 (Stoe, 1995a)'
_computing_data_reduction        'X-RED (Stoe, 1995b)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Stoe Stadi-4 four-circle with Oxford Cryosystems
open-flow cryostat (Cosier & Glazer, 1986)
;
_diffrn_measurement_method       \w/\q
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2607
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        'random variation +-3'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-RED (Stoe, 1995a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.14
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment
'free refinement with common group isotropic displacement parameters'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0357
_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/[\s^2^(Fo^2^)+(0.0354P)^2^+0.263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                1157
_reflns_number_total             1404
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    qb0038.cif
_[local]_cod_data_source_block   oampip
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2007271
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_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_occupancy
_atom_site_type_symbol
N1 0.1909(2) 0.29660(15) 0.14268(9) 0.0274(3) Uani d 1 N
H1N 0.072(3) 0.346(2) 0.1249(13) 0.038(3) Uiso d 1 H
H2N 0.252(3) 0.253(2) 0.0928(13) 0.038(3) Uiso d 1 H
C1 0.3707(2) 0.04204(16) 0.34530(10) 0.0253(4) Uani d 1 C
H1 0.487(3) -0.025(2) 0.3622(12) 0.034(2) Uiso d 1 H
N2 0.48353(18) 0.07982(13) 0.08989(8) 0.0216(3) Uani d 1 N
C2 0.2223(2) 0.06272(17) 0.40913(11) 0.0291(4) Uani d 1 C
H2 0.232(2) 0.0088(19) 0.4721(13) 0.034(2) Uiso d 1 H
C3 0.0635(2) 0.16221(18) 0.38334(11) 0.0297(4) Uani d 1 C
H3 -0.042(3) 0.1795(19) 0.4288(12) 0.034(2) Uiso d 1 H
C4 0.0513(2) 0.23785(18) 0.29460(11) 0.0272(4) Uani d 1 C
H4 -0.062(3) 0.3110(19) 0.2766(12) 0.034(2) Uiso d 1 H
C5 0.1986(2) 0.21615(16) 0.22956(10) 0.0222(3) Uani d 1 C
C6 0.3632(2) 0.11776(16) 0.25615(10) 0.0215(3) Uani d 1 C
C7 0.5415(2) 0.10758(18) 0.19526(10) 0.0245(4) Uani d 1 C
H71 0.616(2) 0.2061(19) 0.1998(12) 0.0299(17) Uiso d 1 H
H72 0.642(2) 0.0293(19) 0.2245(12) 0.0299(17) Uiso d 1 H
C8 0.3953(2) -0.06973(17) 0.07290(11) 0.0272(4) Uani d 1 C
H81 0.493(3) -0.1511(19) 0.0981(12) 0.0299(17) Uiso d 1 H
H82 0.273(3) -0.0775(18) 0.1092(12) 0.0299(17) Uiso d 1 H
C9 0.6634(2) 0.09471(19) 0.03607(11) 0.0278(4) Uani d 1 C
H91 0.719(2) 0.2001(19) 0.0479(12) 0.0299(17) Uiso d 1 H
H92 0.774(2) 0.0200(19) 0.0605(12) 0.0299(17) Uiso d 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
N1 0.0277(7) 0.0309(7) 0.0237(7) 0.0062(6) 0.0027(5) 0.0031(5)
C1 0.0318(8) 0.0215(8) 0.0218(7) -0.0004(6) -0.0009(6) -0.0024(6)
N2 0.0244(6) 0.0213(6) 0.0197(6) -0.0027(5) 0.0054(5) -0.0017(5)
C2 0.0409(9) 0.0263(8) 0.0205(8) -0.0062(7) 0.0048(7) -0.0007(6)
C3 0.0302(9) 0.0342(9) 0.0260(8) -0.0062(7) 0.0097(6) -0.0075(7)
C4 0.0223(8) 0.0305(8) 0.0286(8) -0.0007(6) 0.0016(6) -0.0049(7)
C5 0.0223(7) 0.0230(8) 0.0209(7) -0.0045(6) 0.0000(6) -0.0031(6)
C6 0.0243(8) 0.0203(7) 0.0197(7) -0.0034(6) 0.0010(6) -0.0048(6)
C7 0.0244(8) 0.0270(8) 0.0216(8) -0.0004(6) 0.0006(6) -0.0021(6)
C8 0.0342(9) 0.0244(8) 0.0249(8) -0.0068(7) 0.0114(7) -0.0011(6)
C9 0.0265(8) 0.0308(9) 0.0274(8) -0.0086(7) 0.0084(7) -0.0060(7)
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
C5 N1 H1N . . 115.6(11)
C5 N1 H2N . . 116.3(11)
H1N N1 H2N . . 116.1(16)
C2 C1 C6 . . 121.78(14)
C2 C1 H1 . . 120.9(10)
C6 C1 H1 . . 117.3(10)
C8 N2 C9 . . 109.26(11)
C8 N2 C7 . . 111.44(11)
C9 N2 C7 . . 109.87(11)
C3 C2 C1 . . 118.95(14)
C3 C2 H2 . . 120.7(10)
C1 C2 H2 . . 120.3(10)
C4 C3 C2 . . 120.45(14)
C4 C3 H3 . . 119.8(10)
C2 C3 H3 . . 119.7(10)
C3 C4 C5 . . 120.86(15)
C3 C4 H4 . . 120.4(10)
C5 C4 H4 . . 118.7(9)
N1 C5 C4 . . 120.76(14)
N1 C5 C6 . . 120.04(13)
C4 C5 C6 . . 119.09(13)
C1 C6 C5 . . 118.84(13)
C1 C6 C7 . . 119.90(14)
C5 C6 C7 . . 120.88(13)
N2 C7 C6 . . 114.58(12)
N2 C7 H71 . . 106.3(9)
C6 C7 H71 . . 108.4(9)
N2 C7 H72 . . 111.1(9)
C6 C7 H72 . . 109.4(9)
H71 C7 H72 . . 106.7(13)
N2 C8 C9 . 3_655 110.18(12)
N2 C8 H81 . . 112.2(9)
C9 C8 H81 3_655 . 108.5(9)
N2 C8 H82 . . 108.2(9)
C9 C8 H82 3_655 . 110.4(9)
H81 C8 H82 . . 107.4(13)
N2 C9 C8 . 3_655 110.37(12)
N2 C9 H91 . . 107.5(9)
C8 C9 H91 3_655 . 110.0(9)
N2 C9 H92 . . 111.2(9)
C8 C9 H92 3_655 . 109.0(9)
H91 C9 H92 . . 108.8(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.3857(19)
N1 H1N . 0.904(19)
N1 H2N . 0.915(19)
C1 C2 . 1.389(2)
C1 C6 . 1.392(2)
C1 H1 . 0.977(18)
N2 C8 . 1.4626(19)
N2 C9 . 1.4638(18)
N2 C7 . 1.4736(18)
C2 C3 . 1.386(2)
C2 H2 . 0.984(17)
C3 C4 . 1.385(2)
C3 H3 . 0.990(17)
C4 C5 . 1.397(2)
C4 H4 . 0.998(18)
C5 C6 . 1.410(2)
C6 C7 . 1.511(2)
C7 H71 . 1.004(17)
C7 H72 . 1.012(17)
C8 C9 3_655 1.517(2)
C8 H81 . 1.003(17)
C8 H82 . 0.993(16)
C9 C8 3_655 1.517(2)
C9 H91 . 1.015(17)
C9 H92 . 1.015(17)
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
C6 C1 C2 C3 . -0.4(2)
C1 C2 C3 C4 . 1.0(2)
C2 C3 C4 C5 . -0.3(2)
C3 C4 C5 N1 . -177.28(14)
C3 C4 C5 C6 . -1.2(2)
C2 C1 C6 C5 . -1.0(2)
C2 C1 C6 C7 . 171.98(13)
N1 C5 C6 C1 . 177.94(13)
C4 C5 C6 C1 . 1.8(2)
N1 C5 C6 C7 . 5.0(2)
C4 C5 C6 C7 . -171.17(13)
C8 N2 C7 C6 . -67.30(16)
C9 N2 C7 C6 . 171.46(13)
C1 C6 C7 N2 . 134.40(14)
C5 C6 C7 N2 . -52.72(18)
C9 N2 C8 C9 3_655 -58.58(18)
C7 N2 C8 C9 3_655 179.82(12)
C8 N2 C9 C8 3_655 58.70(18)
C7 N2 C9 C8 3_655 -178.76(13)