#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/42/2014246.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_2014246
loop_
_publ_author_name
'Venkatraman, Ramaiyer'
'Ray, Paresh Chandra'
'Fronczek, Frank R.'
_publ_section_title
;
 The 1:1 adduct of hexamethylenetetramine (HMT) with racemic
 trans-1,2-cyclohexanedicarboxylic acid (CDA)
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o633
_journal_page_last               o635
_journal_paper_doi               10.1107/S0108270104015963
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C6 H12 N4 , C8 H12 O4'
_chemical_formula_moiety         'C6 H12 N4 , C8 H12 O4'
_chemical_formula_sum            'C14 H24 N4 O4'
_chemical_formula_weight         312.37
_chemical_name_systematic
;
Hexamethylenetetramine--rac-trans-1,2-cyclohexanedicarboxylic acid (1:1)
;
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.990(3)
_cell_length_b                   11.814(3)
_cell_length_c                   22.606(6)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    102
_cell_measurement_theta_max      33.1
_cell_measurement_theta_min      2.5
_cell_volume                     3202.1(14)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      102
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Nonius KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            17655
_diffrn_reflns_theta_full        33.1
_diffrn_reflns_theta_max         33.1
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.041
_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)+(0.0511P)²+0.5607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.097
_reflns_number_gt                2652
_reflns_number_total             3119
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1744.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               2014246
_cod_database_fobs_code          2014246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.43824(11) 0.29207(10) 0.22175(6) 0.0225(3) Uani d . 1 . . O
H1O 0.396(2) 0.275(2) 0.2526(13) 0.034 Uiso d . 1 . . H
O2 0.36053(11) 0.46191(11) 0.23555(6) 0.0247(3) Uani d . 1 . . O
O3 0.30918(11) 0.39861(12) 0.50944(6) 0.0252(3) Uani d . 1 . . O
H3O 0.296(2) 0.352(2) 0.4769(13) 0.038 Uiso d . 1 . . H
O4 0.48849(11) 0.35855(12) 0.49274(6) 0.0272(3) Uani d . 1 . . O
N1 0.11509(11) 0.23047(12) 0.34622(7) 0.0154(3) Uani d . 1 . . N
N2 0.24139(12) 0.07814(11) 0.37716(6) 0.0151(3) Uani d . 1 . . N
N3 0.30955(11) 0.22983(11) 0.31311(6) 0.0136(2) Uani d . 1 . . N
N4 0.26459(11) 0.26894(11) 0.41666(6) 0.0148(3) Uani d . 1 . . N
C1 0.12582(13) 0.10846(13) 0.36051(8) 0.0159(3) Uani d . 1 . . C
H1A 0.0750 0.0896 0.3936 0.019 Uiso calc R 1 . . H
H1B 0.1030 0.0631 0.3257 0.019 Uiso calc R 1 . . H
C2 0.31559(14) 0.10774(13) 0.32809(8) 0.0155(3) Uani d . 1 . . C
H2A 0.2950 0.0625 0.2929 0.019 Uiso calc R 1 . . H
H2B 0.3933 0.0882 0.3389 0.019 Uiso calc R 1 . . H
C3 0.33904(13) 0.29520(14) 0.36651(8) 0.0153(3) Uani d . 1 . . C
H3A 0.3344 0.3771 0.3575 0.018 Uiso calc R 1 . . H
H3B 0.4170 0.2779 0.3778 0.018 Uiso calc R 1 . . H
C4 0.14829(13) 0.29488(14) 0.39864(8) 0.0157(3) Uani d . 1 . . C
H4A 0.0971 0.2767 0.4317 0.019 Uiso calc R 1 . . H
H4B 0.1417 0.3768 0.3902 0.019 Uiso calc R 1 . . H
C5 0.19139(14) 0.25643(15) 0.29739(7) 0.0168(3) Uani d . 1 . . C
H5A 0.1852 0.3377 0.2872 0.020 Uiso calc R 1 . . H
H5B 0.1696 0.2120 0.2621 0.020 Uiso calc R 1 . . H
C6 0.27195(15) 0.14611(14) 0.42904(7) 0.0176(3) Uani d . 1 . . C
H6A 0.3491 0.1271 0.4412 0.021 Uiso calc R 1 . . H
H6B 0.2216 0.1271 0.4623 0.021 Uiso calc R 1 . . H
C7 0.42306(13) 0.39993(14) 0.20842(7) 0.0153(3) Uani d . 1 . . C
C8 0.48856(13) 0.43654(14) 0.15431(7) 0.0145(3) Uani d . 1 . . C
H8 0.5615 0.3955 0.1540 0.017 Uiso calc R 1 . . H
C9 0.42250(16) 0.40338(16) 0.09842(8) 0.0212(3) Uani d . 1 . . C
H9A 0.4095 0.3206 0.0983 0.025 Uiso calc R 1 . . H
H9B 0.3490 0.4416 0.0988 0.025 Uiso calc R 1 . . H
C10 0.48636(19) 0.43710(19) 0.04264(8) 0.0298(4) Uani d . 1 . . C
H10A 0.5564 0.3930 0.0403 0.036 Uiso calc R 1 . . H
H10B 0.4409 0.4188 0.0074 0.036 Uiso calc R 1 . . H
C11 0.41698(14) 0.40626(14) 0.52135(7) 0.0152(3) Uani d . 1 . . C
C12 0.44029(13) 0.47767(14) 0.57575(7) 0.0139(3) Uani d . 1 . . C
H12 0.3881 0.5437 0.5758 0.017 Uiso calc R 1 . . H
C13 0.41838(15) 0.40650(14) 0.63174(8) 0.0189(3) Uani d . 1 . . C
H13A 0.3399 0.3803 0.6319 0.023 Uiso calc R 1 . . H
H13B 0.4672 0.3389 0.6315 0.023 Uiso calc R 1 . . H
C14 0.44094(17) 0.47615(18) 0.68738(8) 0.0252(4) Uani d . 1 . . C
H14A 0.3867 0.5392 0.6896 0.030 Uiso calc R 1 . . H
H14B 0.4304 0.4278 0.7227 0.030 Uiso calc R 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 O1 H1O . . 108.4(17)
C11 O3 H3O . . 111.2(17)
C4 N1 C5 . . 109.34(13)
C4 N1 C1 . . 107.78(13)
C5 N1 C1 . . 108.26(13)
C2 N2 C6 . . 108.84(13)
C2 N2 C1 . . 108.56(13)
C6 N2 C1 . . 107.73(13)
C3 N3 C2 . . 108.08(13)
C3 N3 C5 . . 108.16(12)
C2 N3 C5 . . 107.77(12)
C3 N4 C6 . . 108.37(13)
C3 N4 C4 . . 108.30(13)
C6 N4 C4 . . 108.07(12)
N2 C1 N1 . . 111.84(12)
N2 C1 H1A . . 109.2
N1 C1 H1A . . 109.2
N2 C1 H1B . . 109.2
N1 C1 H1B . . 109.2
H1A C1 H1B . . 107.9
N2 C2 N3 . . 112.06(12)
N2 C2 H2A . . 109.2
N3 C2 H2A . . 109.2
N2 C2 H2B . . 109.2
N3 C2 H2B . . 109.2
H2A C2 H2B . . 107.9
N3 C3 N4 . . 111.92(12)
N3 C3 H3A . . 109.2
N4 C3 H3A . . 109.2
N3 C3 H3B . . 109.2
N4 C3 H3B . . 109.2
H3A C3 H3B . . 107.9
N1 C4 N4 . . 111.74(13)
N1 C4 H4A . . 109.3
N4 C4 H4A . . 109.3
N1 C4 H4B . . 109.3
N4 C4 H4B . . 109.3
H4A C4 H4B . . 107.9
N1 C5 N3 . . 111.63(13)
N1 C5 H5A . . 109.3
N3 C5 H5A . . 109.3
N1 C5 H5B . . 109.3
N3 C5 H5B . . 109.3
H5A C5 H5B . . 108.0
N2 C6 N4 . . 111.73(13)
N2 C6 H6A . . 109.3
N4 C6 H6A . . 109.3
N2 C6 H6B . . 109.3
N4 C6 H6B . . 109.3
H6A C6 H6B . . 107.9
O2 C7 O1 . . 123.45(15)
O2 C7 C8 . . 123.72(15)
O1 C7 C8 . . 112.79(14)
C7 C8 C8 . 2_665 111.95(11)
C7 C8 C9 . . 108.82(13)
C8 C8 C9 2_665 . 110.02(12)
C7 C8 H8 . . 108.7
C8 C8 H8 2_665 . 108.7
C9 C8 H8 . . 108.7
C10 C9 C8 . . 110.65(14)
C10 C9 H9A . . 109.5
C8 C9 H9A . . 109.5
C10 C9 H9B . . 109.5
C8 C9 H9B . . 109.5
H9A C9 H9B . . 108.1
C10 C10 C9 2_665 . 111.24(15)
C10 C10 H10A 2_665 . 109.4
C9 C10 H10A . . 109.4
C10 C10 H10B 2_665 . 109.4
C9 C10 H10B . . 109.4
H10A C10 H10B . . 108.0
O4 C11 O3 . . 123.38(16)
O4 C11 C12 . . 124.08(16)
O3 C11 C12 . . 112.51(14)
C11 C12 C12 . 2_665 111.41(11)
C11 C12 C13 . . 109.31(13)
C12 C12 C13 2_665 . 110.39(11)
C11 C12 H12 . . 108.6
C12 C12 H12 2_665 . 108.6
C13 C12 H12 . . 108.6
C14 C13 C12 . . 110.61(14)
C14 C13 H13A . . 109.5
C12 C13 H13A . . 109.5
C14 C13 H13B . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 108.1
C14 C14 C13 2_665 . 111.33(13)
C14 C14 H14A 2_665 . 109.4
C13 C14 H14A . . 109.4
C14 C14 H14B 2_665 . 109.4
C13 C14 H14B . . 109.4
H14A C14 H14B . . 108.0
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
O1 C7 . 1.322(2) y
O1 H1O . 0.88(3) ?
O2 C7 . 1.214(2) y
O3 C11 . 1.323(2) y
O3 H3O . 0.93(3) ?
O4 C11 . 1.213(2) y
N1 C4 . 1.464(2) y
N1 C5 . 1.466(2) y
N1 C1 . 1.483(2) y
N2 C2 . 1.464(2) y
N2 C6 . 1.468(2) y
N2 C1 . 1.480(2) y
N3 C3 . 1.476(2) y
N3 C2 . 1.483(2) y
N3 C5 . 1.494(2) y
N4 C3 . 1.476(2) y
N4 C6 . 1.481(2) y
N4 C4 . 1.485(2) y
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.516(2) ?
C8 C8 2_665 1.524(3) ?
C8 C9 . 1.542(2) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.528(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C10 2_665 1.522(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.517(2) ?
C12 C12 2_665 1.526(3) ?
C12 C13 . 1.542(2) ?
C12 H12 . 1.0000 ?
C13 C14 . 1.527(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C14 2_665 1.524(4) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
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
O1 H1O N3 . 0.88(3) 1.80(3) 2.6808(19) 175(3)
O3 H3O N4 . 0.93(3) 1.72(3) 2.6518(19) 177(3)
C1 H1A O4 4_455 0.99 2.54 3.435(2) 150
C1 H1B O2 3_545 0.99 2.40 3.317(2) 153
C2 H2A O2 3_545 0.99 2.56 3.436(2) 147
C3 H3A N2 3 0.99 2.58 3.487(2) 152
C3 H3B N1 4 0.99 2.48 3.355(2) 147
C4 H4A O4 4_455 0.99 2.48 3.388(2) 152
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C2 N2 C1 N1 . . -58.26(17)
C6 N2 C1 N1 . . 59.46(17)
C4 N1 C1 N2 . . -59.52(17)
C5 N1 C1 N2 . . 58.64(17)
C6 N2 C2 N3 . . -58.47(17)
C1 N2 C2 N3 . . 58.53(16)
C3 N3 C2 N2 . . 58.10(17)
C5 N3 C2 N2 . . -58.57(17)
C2 N3 C3 N4 . . -58.10(16)
C5 N3 C3 N4 . . 58.32(16)
C6 N4 C3 N3 . . 58.38(17)
C4 N4 C3 N3 . . -58.62(16)
C5 N1 C4 N4 . . -58.42(17)
C1 N1 C4 N4 . . 59.04(16)
C3 N4 C4 N1 . . 58.22(16)
C6 N4 C4 N1 . . -58.98(17)
C4 N1 C5 N3 . . 58.12(17)
C1 N1 C5 N3 . . -59.04(17)
C3 N3 C5 N1 . . -57.73(17)
C2 N3 C5 N1 . . 58.89(17)
C2 N2 C6 N4 . . 58.40(17)
C1 N2 C6 N4 . . -59.14(17)
C3 N4 C6 N2 . . -58.21(17)
C4 N4 C6 N2 . . 58.95(18)
O2 C7 C8 C8 . 2_665 26.6(2)
O1 C7 C8 C8 . 2_665 -155.58(16)
O2 C7 C8 C9 . . -95.17(19)
O1 C7 C8 C9 . . 82.61(17)
C7 C8 C9 C10 . . -179.13(16)
C8 C8 C9 C10 2_665 . 57.9(2)
C8 C9 C10 C10 . 2_665 -56.1(3)
O4 C11 C12 C12 . 2_665 23.5(2)
O3 C11 C12 C12 . 2_665 -158.52(16)
O4 C11 C12 C13 . . -98.8(2)
O3 C11 C12 C13 . . 79.21(17)
C11 C12 C13 C14 . . -179.90(15)
C12 C12 C13 C14 2_665 . 57.2(2)
C12 C13 C14 C14 . 2_665 -56.0(2)
