#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:54:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180362 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/31/7203138.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_7203138
loop_
_publ_author_name
'van den Ancker, Tania R.'
'Cave, Gareth W. V.'
'Raston, Colin L.'
_publ_section_title
;
 Benign approaches for the synthesis of bis-imine Schiff bases
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              50
_journal_paper_doi               10.1039/b513289d
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         C5NH4CHNC6H10NCHC5NH4
_chemical_formula_sum            'C18 H20 N4'
_chemical_formula_weight         292.38
_chemical_name_common
;(N-Pyridin-4-ylmethylene)(N'-pyridin-2-ylmethylene)
cyclohexane-1,2-diamine
;
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 112.752(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.5824(14)
_cell_length_b                   5.7010(3)
_cell_length_c                   16.8318(9)
_cell_measurement_temperature    150(2)
_cell_volume                     3148.7(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor)'
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      396(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type
;
Nonius KappaCCD area detector
diffractometer
;
_diffrn_measurement_method
;
Detector set at 30mm from sample with different 2theta offsets
1 degree phi exposures for chi=0 degree settings
1 degree omega exposures for chi=0 degree settings
;
_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  0.1037
_diffrn_reflns_av_sigmaI/netI    0.0978
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11262
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0665
_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)+(0.0833P)²+1.5120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1844
_reflns_number_gt                2278
_reflns_number_total             3804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b513289d.txt
_cod_data_source_block           dipyridine
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7203138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.08119(6) 1.0234(4) 0.12361(13) 0.0307(5) Uani 1 1 d . . .
H1 H 0.1063 1.0208 0.1187 0.037 Uiso 1 1 calc R . .
C2 C 0.07181(7) 1.1991(4) 0.16802(14) 0.0366(5) Uani 1 1 d . . .
H2 H 0.0909 1.3156 0.1941 0.044 Uiso 1 1 calc R . .
C3 C 0.03476(7) 1.2060(4) 0.17455(15) 0.0368(6) Uani 1 1 d . . .
H3 H 0.0280 1.3269 0.2037 0.044 Uiso 1 1 calc R . .
C4 C 0.00788(7) 1.0286(5) 0.13667(16) 0.0440(6) Uani 1 1 d . . .
H4 H -0.0173 1.0322 0.1413 0.053 Uiso 1 1 calc R . .
N5 N 0.01566(6) 0.8471(4) 0.09261(13) 0.0416(5) Uani 1 1 d . . .
C6 C 0.05258(6) 0.8485(4) 0.08584(12) 0.0269(5) Uani 1 1 d . . .
C7 C 0.06040(6) 0.6526(4) 0.03756(13) 0.0292(5) Uani 1 1 d . . .
H7 H 0.0423 0.5269 0.0216 0.035 Uiso 1 1 calc R . .
N8 N 0.09125(5) 0.6507(3) 0.01712(11) 0.0301(4) Uani 1 1 d . . .
C9 C 0.09703(6) 0.4432(4) -0.02741(13) 0.0285(5) Uani 1 1 d . . .
H9 H 0.0832 0.3096 -0.0140 0.034 Uiso 1 1 calc R . .
C10 C 0.07950(7) 0.4827(4) -0.12487(13) 0.0345(5) Uani 1 1 d . . .
H10A H 0.0504 0.5106 -0.1447 0.041 Uiso 1 1 calc R . .
H10B H 0.0919 0.6210 -0.1380 0.041 Uiso 1 1 calc R . .
C11 C 0.08705(7) 0.2734(4) -0.17226(14) 0.0355(5) Uani 1 1 d . . .
H11A H 0.0774 0.3090 -0.2333 0.043 Uiso 1 1 calc R . .
H11B H 0.0717 0.1400 -0.1652 0.043 Uiso 1 1 calc R . .
C12 C 0.13204(7) 0.2098(4) -0.13918(14) 0.0375(6) Uani 1 1 d . . .
H12A H 0.1468 0.3337 -0.1540 0.045 Uiso 1 1 calc R . .
H12B H 0.1353 0.0668 -0.1670 0.045 Uiso 1 1 calc R . .
C13 C 0.14986(7) 0.1747(4) -0.04193(14) 0.0349(5) Uani 1 1 d . . .
H13A H 0.1789 0.1450 -0.0225 0.042 Uiso 1 1 calc R . .
H13B H 0.1373 0.0390 -0.0275 0.042 Uiso 1 1 calc R . .
C14 C 0.14280(6) 0.3902(4) 0.00416(13) 0.0288(5) Uani 1 1 d . . .
H14 H 0.1567 0.5251 -0.0083 0.035 Uiso 1 1 calc R . .
N15 N 0.15901(5) 0.3509(3) 0.09710(11) 0.0298(4) Uani 1 1 d . . .
C16 C 0.18014(6) 0.5139(4) 0.14457(13) 0.0286(5) Uani 1 1 d . . .
H16 H 0.1849 0.6488 0.1188 0.034 Uiso 1 1 calc R . .
C17 C 0.19764(6) 0.4971(4) 0.23979(13) 0.0276(5) Uani 1 1 d . . .
C18 C 0.21996(6) 0.6802(4) 0.28684(14) 0.0302(5) Uani 1 1 d . . .
H18 H 0.2238 0.8140 0.2593 0.036 Uiso 1 1 calc R . .
C19 C 0.23672(7) 0.6657(4) 0.37533(16) 0.0400(6) Uani 1 1 d . . .
H19 H 0.2518 0.7927 0.4060 0.048 Uiso 1 1 calc R . .
N20 N 0.23258(6) 0.4799(4) 0.41991(13) 0.0477(6) Uani 1 1 d . . .
C21 C 0.21020(8) 0.2986(4) 0.37218(16) 0.0456(6) Uani 1 1 d . . .
H21 H 0.2067 0.1663 0.4009 0.055 Uiso 1 1 calc R . .
C22 C 0.19249(7) 0.3012(4) 0.28362(15) 0.0354(5) Uani 1 1 d . . .
H22 H 0.1773 0.1737 0.2535 0.043 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'
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
_geom_angle_publ_flag
C2 C1 C6 119.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C2 C3 C4 117.7(2) . . ?
N5 C4 C3 124.2(2) . . ?
C6 N5 C4 116.5(2) . . ?
N5 C6 C1 121.69(19) . . ?
N5 C6 C7 115.91(19) . . ?
C1 C6 C7 122.40(19) . . ?
N8 C7 C6 121.61(19) . . ?
C7 N8 C9 117.02(18) . . ?
N8 C9 C10 110.61(17) . . ?
N8 C9 C14 108.88(16) . . ?
C10 C9 C14 109.76(16) . . ?
C11 C10 C9 111.52(18) . . ?
C10 C11 C12 111.75(18) . . ?
C11 C12 C13 111.51(18) . . ?
C12 C13 C14 111.05(18) . . ?
N15 C14 C13 110.32(17) . . ?
N15 C14 C9 109.11(15) . . ?
C13 C14 C9 110.13(17) . . ?
C16 N15 C14 117.12(17) . . ?
N15 C16 C17 122.29(19) . . ?
C18 C17 C22 118.27(19) . . ?
C18 C17 C16 119.04(19) . . ?
C22 C17 C16 122.68(18) . . ?
C17 C18 C19 119.6(2) . . ?
N20 C19 C18 124.0(2) . . ?
C19 N20 C21 115.9(2) . . ?
N20 C21 C22 123.3(2) . . ?
C21 C22 C17 119.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.366(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.365(3) . ?
C3 C4 1.368(3) . ?
C4 N5 1.363(3) . ?
N5 C6 1.362(3) . ?
C6 C7 1.470(3) . ?
C7 N8 1.271(3) . ?
N8 C9 1.457(3) . ?
C9 C10 1.530(3) . ?
C9 C14 1.535(3) . ?
C10 C11 1.516(3) . ?
C11 C12 1.521(3) . ?
C12 C13 1.523(3) . ?
C13 C14 1.525(3) . ?
C14 N15 1.460(3) . ?
N15 C16 1.266(3) . ?
C16 C17 1.481(3) . ?
C17 C18 1.364(3) . ?
C17 C22 1.389(3) . ?
C18 C19 1.376(3) . ?
C19 N20 1.339(3) . ?
N20 C21 1.361(3) . ?
C21 C22 1.376(3) . ?
