#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2003110.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_2003110
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     1999
_journal_volume     B55
_journal_page_first     448
_journal_page_last     458
_publ_section_title
;
Phase Transition Induced Twinning in the 1:1
Adduct of Hexamethylenetetramine and Azelaic Acid
;
loop_
    _publ_author_name
    'Marc Hostettler'
    'Henrik Birkedal'
    'Manual Gardon'
    'Gervais Chapuis'
    'Dieter Schwarzenbach'
    'Michel Bonin'
_chemical_name_common
                         "1:1 adduct of hexamethylenetetramine and azelaic acid"
_chemical_formula_moiety     'C6 H12 N4,C9 H16 O4'
_chemical_formula_sum     'C15 H28 N4 O4'
_chemical_formula_weight     328.41
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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'
_cell_length_a     5.8907(7)
_cell_length_b     26.071(2)
_cell_length_c     11.8868(11)
_cell_angle_alpha     90.00
_cell_angle_beta     106.118(9)
_cell_angle_gamma     90.00
_cell_volume     1753.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     258.0(10)
_exptl_crystal_description     platelet
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.244
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     712
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     258.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     "Stoe IPDS imaging plate system"
_diffrn_measurement_method     oscillation
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6256
_diffrn_reflns_av_R_equivalents     "see _diffrn_special_details"
_diffrn_reflns_av_sigmaI/netI     0.0295
_diffrn_reflns_theta_min     2.37
_diffrn_reflns_theta_max     20.80
_diffrn_reflns_theta_full     20.80
_diffrn_measured_fraction_theta_max     0.657
_diffrn_measured_fraction_theta_full     0.657
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     1443
_reflns_number_gt     1443
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0469
_refine_ls_R_factor_gt     0.0469
_refine_ls_wR_factor_ref     0.1364
_refine_ls_goodness_of_fit_ref     1.150
_refine_ls_restrained_S_all     1.147
_refine_ls_number_reflns     1443
_refine_ls_number_parameters     246
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme
         'calc w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+0.0702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.168
_refine_diff_density_min     -0.115
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
                     'EXPOSE (STOE & CIE GmbH (1997) IPDS 2.87 Software Manual)'
                'INDEX, CELL (STOE & CIE GmbH (1997) IPDS 2.87 Software Manual)'
;
PROFILE, EMS, INTEGRATE (STOE & CIE GmbH (1997) IPDS 2.87 Software
Manual), XPREP Version 5.04, Siemens Analytical X-ray Insts. (1996)
and home written programs
;
;
XP Version 5.04, Siemens Analytical X-ray Insts. (1996)
;
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
    O1A -0.025(7) 0.875(2) 0.098(4) 0.108(12) Uani d PU 0.29(4) . . O
    O1B -0.056(2) 0.8552(4) 0.0475(16) 0.076(3) Uani d PU 0.71(4) . . O
    O2A 0.291(7) 0.8681(16) 0.048(4) 0.090(11) Uani d PU 0.29(4) . . O
    O2B 0.310(2) 0.8795(6) 0.0680(14) 0.075(4) Uani d PU 0.71(4) . . O
    H2O 0.3406 0.8557 0.1214 0.112 Uiso calc PR 0.71(4) . . H
    C11 0.0823(9) 0.88405(15) 0.0257(4) 0.0509(12) Uani d U 1 . . C
    C12 0.0111(8) 0.92394(16) -0.0675(4) 0.0568(13) Uani d . 1 . . C
    H12A 0.0357 0.9101 -0.1389 0.068 Uiso calc R 1 . . H
    H12B 0.1164 0.9530 -0.0446 0.068 Uiso calc R 1 . . H
    C13 -0.2383(8) 0.94317(15) -0.0946(4) 0.0575(13) Uani d . 1 . . C
    H13A -0.2578 0.9624 -0.0281 0.069 Uiso calc R 1 . . H
    H13B -0.3452 0.9141 -0.1068 0.069 Uiso calc R 1 . . H
    C14 -0.3034(9) 0.97712(18) -0.2026(5) 0.0692(15) Uani d . 1 . . C
    H14A -0.1861 1.0041 -0.1919 0.083 Uiso calc R 1 . . H
    H14B -0.2920 0.9567 -0.2690 0.083 Uiso calc R 1 . . H
    C15 -0.5437(8) 1.00182(18) -0.2334(4) 0.0607(12) Uani d . 1 . . C
    H15A -0.5499 1.0265 -0.1732 0.073 Uiso calc R 1 . . H
    H15B -0.6623 0.9758 -0.2354 0.073 Uiso calc R 1 . . H
    C16 -0.6007(9) 1.02870(18) -0.3506(4) 0.0666(15) Uani d . 1 . . C
    H16A -0.4717 1.0519 -0.3502 0.080 Uiso calc R 1 . . H
    H16B -0.6058 1.0031 -0.4105 0.080 Uiso calc R 1 . . H
    C17 -0.8278(9) 1.05880(16) -0.3857(4) 0.0596(14) Uani d . 1 . . C
    H17A -0.8190 1.0869 -0.3312 0.072 Uiso calc R 1 . . H
    H17B -0.9577 1.0368 -0.3814 0.072 Uiso calc R 1 . . H
    C18 -0.8753(8) 1.07994(17) -0.5081(4) 0.0569(13) Uani d . 1 . . C
    H18A -0.7358 1.0984 -0.5134 0.068 Uiso calc R 1 . . H
    H18B -0.8967 1.0512 -0.5620 0.068 Uiso calc R 1 . . H
    C19 -1.0829(9) 1.11470(15) -0.5487(5) 0.0546(12) Uani d U 1 . . C
    O3A -1.237(8) 1.1182(16) -0.499(5) 0.072(9) Uani d PU 0.29(4) . . O
    O3B -1.178(4) 1.1367(7) -0.486(2) 0.088(5) Uani d PU 0.71(4) . . O
    O4A -1.119(6) 1.1335(18) -0.652(4) 0.078(11) Uani d PU 0.29(4) . . O
    O4B -1.130(2) 1.1250(7) -0.6618(14) 0.067(4) Uani d PU 0.71(4) . . O
    H4O -1.2724 1.1373 -0.6868 0.101 Uiso calc PR 0.71(4) . . H
    N1 0.4557(6) 0.79563(12) 0.2069(3) 0.0460(9) Uani d . 1 . . N
    H1 0.3891 0.8230 0.1622 0.055 Uiso calc PR 0.29(4) . . H
    N2 0.4336(6) 0.70364(11) 0.2341(3) 0.0449(9) Uani d . 1 . . N
    H2 0.3519 0.6746 0.2058 0.054 Uiso calc PR 0.29(4) . . H
    N3 0.8159(6) 0.74534(13) 0.2758(3) 0.0495(10) Uani d . 1 . . N
    N4 0.5608(7) 0.75981(13) 0.4034(3) 0.0509(10) Uani d . 1 . . N
    C1 0.3276(8) 0.74864(15) 0.1633(4) 0.0486(10) Uani d . 1 . . C
    H1A 0.3282 0.7432 0.0826 0.058 Uiso calc R 1 . . H
    H1B 0.1645 0.7522 0.1648 0.058 Uiso calc R 1 . . H
    C2 0.7049(7) 0.78895(16) 0.2057(4) 0.0507(12) Uani d . 1 . . C
    H2A 0.7106 0.7841 0.1256 0.061 Uiso calc R 1 . . H
    H2B 0.7930 0.8198 0.2356 0.061 Uiso calc R 1 . . H
    C3 0.4510(9) 0.80276(16) 0.3295(4) 0.0566(13) Uani d . 1 . . C
    H3A 0.5338 0.8342 0.3600 0.068 Uiso calc R 1 . . H
    H3B 0.2885 0.8062 0.3319 0.068 Uiso calc R 1 . . H
    C4 0.6794(8) 0.69955(16) 0.2305(4) 0.0548(13) Uani d . 1 . . C
    H4A 0.7522 0.6701 0.2764 0.066 Uiso calc R 1 . . H
    H4B 0.6825 0.6939 0.1503 0.066 Uiso calc R 1 . . H
    C5 0.8048(8) 0.75397(17) 0.3963(5) 0.0589(12) Uani d . 1 . . C
    H5A 0.8938 0.7846 0.4271 0.071 Uiso calc R 1 . . H
    H5B 0.8783 0.7253 0.4448 0.071 Uiso calc R 1 . . H
    C6 0.4308(7) 0.71313(15) 0.3560(4) 0.0483(12) Uani d . 1 . . C
    H6A 0.2685 0.7163 0.3590 0.058 Uiso calc R 1 . . H
    H6B 0.5010 0.6841 0.4042 0.058 Uiso calc R 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
    O1A 0.098(17) 0.16(3) 0.08(2) 0.007(19) 0.044(17) 0.057(19)
    O1B 0.065(4) 0.069(5) 0.084(9) -0.014(3) 0.007(5) 0.036(4)
    O2A 0.116(17) 0.09(2) 0.100(17) 0.062(18) 0.086(17) 0.028(14)
    O2B 0.066(5) 0.054(5) 0.092(8) -0.008(4) 0.003(5) 0.033(5)
    C11 0.058(3) 0.041(3) 0.053(4) -0.004(2) 0.015(3) 0.002(2)
    C12 0.071(3) 0.046(2) 0.052(3) -0.002(2) 0.014(3) 0.010(2)
    C13 0.071(3) 0.043(2) 0.060(3) 0.004(2) 0.020(3) 0.006(2)
    C14 0.085(4) 0.064(3) 0.061(4) 0.015(3) 0.023(3) 0.018(2)
    C15 0.074(3) 0.054(2) 0.055(3) 0.010(2) 0.019(3) 0.009(2)
    C16 0.080(4) 0.061(3) 0.061(4) 0.012(3) 0.023(3) 0.014(2)
    C17 0.075(3) 0.045(2) 0.060(4) 0.010(2) 0.022(3) 0.006(2)
    C18 0.070(3) 0.049(2) 0.052(3) 0.011(2) 0.017(3) 0.002(2)
    C19 0.071(4) 0.038(2) 0.059(4) 0.004(2) 0.025(3) -0.003(2)
    O3A 0.081(15) 0.07(2) 0.071(18) 0.031(14) 0.037(13) 0.023(17)
    O3B 0.129(13) 0.079(9) 0.066(5) 0.048(8) 0.044(8) 0.004(8)
    O4A 0.101(18) 0.09(2) 0.077(14) -0.003(12) 0.074(15) 0.014(13)
    O4B 0.082(7) 0.062(5) 0.050(5) 0.039(5) 0.006(5) 0.008(3)
    N1 0.051(2) 0.0436(19) 0.045(3) 0.0034(17) 0.0157(18) 0.0069(16)
    N2 0.047(2) 0.0436(19) 0.044(3) -0.0037(16) 0.0125(18) -0.0031(16)
    N3 0.038(2) 0.063(2) 0.049(3) 0.0004(17) 0.0128(18) 0.0026(18)
    N4 0.057(2) 0.058(2) 0.040(3) -0.0041(19) 0.017(2) -0.0025(18)
    C1 0.045(3) 0.058(3) 0.040(3) 0.001(2) 0.007(2) 0.000(2)
    C2 0.049(3) 0.058(3) 0.047(3) -0.005(2) 0.017(2) 0.005(2)
    C3 0.070(3) 0.049(2) 0.056(4) 0.001(2) 0.026(3) -0.008(2)
    C4 0.060(3) 0.054(3) 0.055(3) 0.015(2) 0.023(3) 0.002(2)
    C5 0.050(3) 0.071(3) 0.048(4) -0.008(2) 0.002(2) 0.003(2)
    C6 0.046(3) 0.056(3) 0.046(3) -0.002(2) 0.018(2) 0.007(2)