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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/35/4503550.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_4503550
loop_
_publ_author_name
'Scott, Janet L.'
'Hachiken, Satoshi'
'Tanaka, Koichi'
_publ_section_title
;
 Efficient Isomeric Enrichment in Cocrystals of Cyclohexanediamines and
 Low Molecular Weight Diols
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2447
_journal_paper_doi               10.1021/cg800032m
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C6 H14 N2, C8 H10 O2 '
_chemical_formula_sum            'C14 H24 N2 O2'
_chemical_formula_weight         252.35
_chemical_name_common
;
1,4-benzenedimethanol trans-1,2-cyclohexanediamine co-crystal 
;
_chemical_name_systematic
; 
1,4-benzenedimethanol trans-1,2-cyclohexanediamine co-crystal 
;
_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                98.83(3)
_cell_angle_beta                 99.36(3)
_cell_angle_gamma                91.31(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0490(10)
_cell_length_b                   10.400(2)
_cell_length_c                   13.804(3)
_cell_measurement_temperature    123(2)
_cell_volume                     705.9(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    X-Seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '0.5 deg scansin phi and omega'
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13133
_diffrn_reflns_theta_full        40.06
_diffrn_reflns_theta_max         40.06
_diffrn_reflns_theta_min         3.88
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             276
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         8285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0618
_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)+(0.0808P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1707
_reflns_number_gt                5096
_reflns_number_total             8285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800032m-file.002.cif
_cod_data_source_block           1.trans-4
_cod_original_cell_volume        705.9(2)
_cod_original_sg_symbol_H-M      p_-1
_cod_database_code               4503550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1A O 0.21592(15) 0.82130(6) 0.52223(6) 0.02020(14) Uani 1 1 d .
C3A C 0.4109(2) 0.53606(9) 0.40805(7) 0.01883(17) Uani 1 1 d .
H3A H 0.3512 0.5604 0.3448 0.023 Uiso 1 1 calc R
C2A C 0.30420(19) 0.59388(8) 0.49039(7) 0.01653(16) Uani 1 1 d .
C1A C 0.0963(2) 0.69437(9) 0.48097(8) 0.01962(17) Uani 1 1 d .
H1A1 H 0.0195 0.6922 0.4100 0.024 Uiso 1 1 calc R
H1A2 H -0.0512 0.6746 0.5165 0.024 Uiso 1 1 calc R
C4A C 0.6033(2) 0.44335(9) 0.41745(7) 0.01876(17) Uani 1 1 d .
H4A H 0.6729 0.4048 0.3605 0.023 Uiso 1 1 calc R
C2 C 0.40249(18) 0.95901(9) 0.25773(7) 0.01634(15) Uani 1 1 d .
H2 H 0.5719 1.0122 0.2874 0.020 Uiso 1 1 calc R
N2 N 0.42361(17) 0.82863(8) 0.28739(7) 0.01847(15) Uani 1 1 d .
C1 C 0.16515(18) 1.02717(9) 0.29610(7) 0.01581(15) Uani 1 1 d .
H1 H -0.0009 0.9701 0.2695 0.019 Uiso 1 1 calc R
N1 N 0.19605(18) 1.05070(8) 0.40542(6) 0.01917(15) Uani 1 1 d .
C6 C 0.1256(2) 1.15732(9) 0.25817(8) 0.02049(18) Uani 1 1 d .
H6A H -0.0366 1.1964 0.2796 0.025 Uiso 1 1 calc R
H6B H 0.2819 1.2176 0.2883 0.025 Uiso 1 1 calc R
C3 C 0.3684(2) 0.94399(10) 0.14440(7) 0.02216(19) Uani 1 1 d .
H3B H 0.2094 0.8853 0.1145 0.027 Uiso 1 1 calc R
H3C H 0.5282 0.9036 0.1219 0.027 Uiso 1 1 calc R
C5 C 0.0946(2) 1.14224(12) 0.14514(8) 0.0253(2) Uani 1 1 d .
H5A H -0.0730 1.0901 0.1147 0.030 Uiso 1 1 calc R
H5B H 0.0807 1.2292 0.1244 0.030 Uiso 1 1 calc R
C4 C 0.3333(2) 1.07546(11) 0.10846(8) 0.0260(2) Uani 1 1 d .
H4B H 0.4985 1.1318 0.1335 0.031 Uiso 1 1 calc R
H4C H 0.3044 1.0622 0.0349 0.031 Uiso 1 1 calc R
O1B O 0.92232(16) 0.70277(8) 0.21267(6) 0.02473(16) Uani 1 1 d .
C2B C 0.7139(2) 0.53698(9) 0.07944(7) 0.01912(17) Uani 1 1 d .
C3B C 0.6308(2) 0.62153(9) 0.01242(8) 0.02171(18) Uani 1 1 d .
H3B1 H 0.7189 0.7051 0.0205 0.026 Uiso 1 1 calc R
C4B C 0.4201(2) 0.58455(9) -0.06603(8) 0.02217(19) Uani 1 1 d .
H4B1 H 0.3667 0.6431 -0.1112 0.027 Uiso 1 1 calc R
C1B C 0.9477(2) 0.57553(10) 0.16310(9) 0.0264(2) Uani 1 1 d .
H1B1 H 0.9542 0.5133 0.2109 0.032 Uiso 1 1 calc R
H1B2 H 1.1178 0.5718 0.1360 0.032 Uiso 1 1 calc R
H1N2 H 0.204(3) 0.9743(16) 0.4316(12) 0.035(4) Uiso 1 1 d .
H1OA H 0.084(4) 0.8668(18) 0.5487(13) 0.046(5) Uiso 1 1 d .
H1N1 H 0.342(3) 1.0982(16) 0.4279(12) 0.031(4) Uiso 1 1 d .
H1OB H 1.083(4) 0.7387(18) 0.2395(13) 0.045(5) Uiso 1 1 d .
H2N1 H 0.457(4) 0.8360(18) 0.3544(14) 0.044(5) Uiso 1 1 d .
H2N2 H 0.564(3) 0.7887(17) 0.2638(12) 0.039(4) Uiso 1 1 d .
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'
O O 0.0106 0.0060 '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
C4A C3A C2A 120.79(9) . .
C3A C2A C4A 118.34(9) . 2_666
C3A C2A C1A 121.16(9) . .
C4A C2A C1A 120.49(9) 2_666 .
O1A C1A C2A 109.94(8) . .
C3A C4A C2A 120.87(9) . 2_666
N2 C2 C3 108.85(8) . .
N2 C2 C1 110.01(8) . .
C3 C2 C1 111.05(8) . .
N1 C1 C6 108.77(8) . .
N1 C1 C2 113.12(8) . .
C6 C1 C2 110.57(8) . .
C5 C6 C1 112.34(9) . .
C2 C3 C4 111.46(9) . .
C4 C5 C6 110.83(9) . .
C5 C4 C3 110.53(9) . .
C4B C2B C3B 118.39(9) 2_665 .
C4B C2B C1B 120.94(9) 2_665 .
C3B C2B C1B 120.65(9) . .
C4B C3B C2B 120.57(9) . .
C3B C4B C2B 121.04(9) . 2_665
O1B C1B C2B 110.62(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C1A 1.4326(13) .
C3A C4A 1.3895(14) .
C3A C2A 1.3955(14) .
C2A C4A 1.3974(14) 2_666
C2A C1A 1.5026(13) .
C4A C2A 1.3974(14) 2_666
C2 N2 1.4767(12) .
C2 C3 1.5289(14) .
C2 C1 1.5326(13) .
C1 N1 1.4730(13) .
C1 C6 1.5304(13) .
C6 C5 1.5257(15) .
C3 C4 1.5291(15) .
C5 C4 1.5231(15) .
O1B C1B 1.4122(14) .
C2B C4B 1.3922(14) 2_665
C2B C3B 1.3950(15) .
C2B C1B 1.5101(15) .
C3B C4B 1.3896(15) .
C4B C2B 1.3922(14) 2_665
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C4A C3A C2A C4A 0.30(16) . 2_666
C4A C3A C2A C1A 179.90(9) . .
C3A C2A C1A O1A -105.38(11) . .
C4A C2A C1A O1A 74.22(12) 2_666 .
C2A C3A C4A C2A -0.30(16) . 2_666
N2 C2 C1 N1 62.72(10) . .
C3 C2 C1 N1 -176.71(8) . .
N2 C2 C1 C6 -175.01(8) . .
C3 C2 C1 C6 -54.44(11) . .
N1 C1 C6 C5 179.42(8) . .
C2 C1 C6 C5 54.64(11) . .
N2 C2 C3 C4 177.57(8) . .
C1 C2 C3 C4 56.32(11) . .
C1 C6 C5 C4 -55.70(12) . .
C6 C5 C4 C3 56.05(13) . .
C2 C3 C4 C5 -56.94(12) . .
C4B C2B C3B C4B -0.35(17) 2_665 .
C1B C2B C3B C4B 178.32(10) . .
C2B C3B C4B C2B 0.36(18) . 2_665
C4B C2B C1B O1B -134.08(11) 2_665 .
C3B C2B C1B O1B 47.28(14) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145263
