#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012438.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_2012438
loop_
_publ_author_name
'Usman, Anwar'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Poh, Bo-Long'
'Karalai, Chatchanok'
_publ_section_title
;
 Hexamethylenetetraminium 2,4,6-trinitrophenolate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o46
_journal_page_last               o47
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C6 H13 N4 1+, C6 H2 N3 O7 1-'
_chemical_formula_sum            'C12 H15 N7 O7'
_chemical_formula_weight         369.31
_chemical_name_systematic
;
Hexamethylenetetramine-2,4,6-trinitrophenol
;
_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'
_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                 107.0220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4995(2)
_cell_length_b                   6.63440(10)
_cell_length_c                   18.6203(2)
_cell_measurement_reflns_used    6652
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.23
_cell_volume                     1476.48(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .975
_diffrn_measured_fraction_theta_max .975
_diffrn_measurement_device_type
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0690
_diffrn_reflns_av_sigmaI/netI    .0961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8504
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .139
_exptl_absorpt_correction_T_max  .9570
_exptl_absorpt_correction_T_min  .9466
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .32
_refine_diff_density_max         .425
_refine_diff_density_min         -.430
_refine_ls_extinction_coef       .033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   .951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .951
_refine_ls_R_factor_all          .0689
_refine_ls_R_factor_gt           .0580
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0807P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1474
_refine_ls_wR_factor_ref         .1539
_reflns_number_gt                2697
_reflns_number_total             3575
_reflns_threshold_expression     'I > 2\s(I)'
_[local]_cod_data_source_file    ln1125.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P21/c
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2012438
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 .60294(10) .5516(2) .07795(8) .0320(3) Uani d . 1 O
O2 .45903(14) .8527(2) .04912(12) .0550(5) Uani d . 1 O
O3 .29116(13) .7894(3) .04515(12) .0615(6) Uani d . 1 O
O4 .18616(10) .2220(2) .15681(8) .0312(4) Uani d . 1 O
O5 .30662(12) -.0030(2) .21338(10) .0438(4) Uani d . 1 O
O6 .67789(12) .0254(2) .20283(10) .0431(4) Uani d . 1 O
O7 .73586(11) .2486(2) .14037(10) .0408(4) Uani d . 1 O
N3 .66203(12) .1781(2) .16407(9) .0223(3) Uani d . 1 N
N2 .28268(12) .1539(2) .17746(8) .0227(3) Uani d . 1 N
N1 .38972(12) .7422(2) .06093(9) .0243(3) Uani d . 1 N
N4 .81992(11) .61547(19) .09625(7) .0149(3) Uani d . 1 N
N5 .97556(10) .7577(2) .19366(7) .0157(3) Uani d . 1 N
N6 1.00739(11) .59303(19) .08449(8) .0160(3) Uani d . 1 N
N7 .91067(11) .91728(19) .07003(8) .0151(3) Uani d . 1 N
C1 .53481(13) .4662(2) .10504(9) .0182(3) Uani d . 1 C
C2 .42297(13) .5466(2) .09739(9) .0171(3) Uani d . 1 C
C3 .34367(13) .4483(2) .12158(9) .0168(3) Uani d . 1 C
H3A .2733 .5054 .1143 .020 Uiso calc R 1 H
C4 .36892(13) .2631(2) .15695(9) .0170(3) Uani d . 1 C
C5 .47419(13) .1785(2) .17098(9) .0175(3) Uani d . 1 C
H5A .4908 .0567 .1966 .021 Uiso calc R 1 H
C6 .55404(13) .2770(2) .14654(9) .0176(3) Uani d . 1 C
C7 .86933(13) .6544(2) .17982(9) .0167(3) Uani d . 1 C
H7A .8181 .7361 .1978 .020 Uiso calc R 1 H
H7B .8802 .5274 .2068 .020 Uiso calc R 1 H
C8 .90167(14) .4883(2) .06953(9) .0174(3) Uani d . 1 C
H8A .9127 .3597 .0954 .021 Uiso calc R 1 H
H8B .8717 .4629 .0161 .021 Uiso calc R 1 H
C9 .80422(13) .8160(2) .05523(9) .0162(3) Uani d . 1 C
H9A .7730 .7938 .0017 .019 Uiso calc R 1 H
H9B .7524 .8994 .0720 .019 Uiso calc R 1 H
C10 1.05185(13) .6316(2) .16567(9) .0181(3) Uani d . 1 C
H10A 1.1237 .6986 .1758 .022 Uiso calc R 1 H
H10B 1.0635 .5042 .1924 .022 Uiso calc R 1 H
C11 .98830(13) .7876(2) .04477(9) .0173(3) Uani d . 1 C
H11A .9580 .7635 -.0087 .021 Uiso calc R 1 H
H11B 1.0593 .8568 .0532 .021 Uiso calc R 1 H
C12 .95718(13) .9492(2) .15161(9) .0169(3) Uani d . 1 C
H12A .9062 1.0326 .1691 .020 Uiso calc R 1 H
H12B 1.0277 1.0207 .1615 .020 Uiso calc R 1 H
H1N4 .751(2) .550(3) .0879(14) .046(7) 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
O1 .0130(6) .0422(8) .0414(8) -.0030(5) .0087(6) .0185(6)
O2 .0472(10) .0246(8) .1038(16) -.0003(7) .0387(10) .0197(8)
O3 .0211(8) .0479(10) .1066(16) .0081(7) .0046(9) .0446(10)
O4 .0117(6) .0399(8) .0434(8) .0009(5) .0104(6) .0099(6)
O5 .0277(8) .0465(9) .0591(10) .0008(6) .0156(7) .0337(8)
O6 .0261(8) .0465(9) .0603(11) .0174(6) .0181(7) .0281(8)
O7 .0222(7) .0264(7) .0838(13) .0037(5) .0310(8) .0089(7)
N3 .0146(7) .0219(7) .0309(8) .0009(5) .0074(6) -.0016(6)
N2 .0145(7) .0314(8) .0226(7) -.0016(6) .0062(6) .0078(6)
N1 .0219(8) .0202(7) .0281(8) -.0014(6) .0032(6) .0033(6)
N4 .0103(6) .0165(6) .0183(7) -.0016(5) .0048(5) .0009(5)
N5 .0119(6) .0188(6) .0160(6) .0006(5) .0033(5) .0012(5)
N6 .0148(7) .0172(6) .0183(7) .0019(5) .0082(5) .0020(5)
N7 .0143(6) .0144(6) .0175(6) .0007(5) .0058(5) .0019(5)
C1 .0115(7) .0242(8) .0181(8) -.0041(6) .0030(6) -.0002(6)
C2 .0139(8) .0174(7) .0184(8) -.0014(6) .0022(6) .0011(6)
C3 .0117(7) .0219(8) .0165(7) .0001(6) .0035(6) -.0013(6)
C4 .0116(8) .0229(8) .0176(8) -.0023(6) .0062(6) .0021(6)
C5 .0143(8) .0190(7) .0181(8) .0000(6) .0031(6) .0012(6)
C6 .0099(7) .0218(8) .0204(8) .0006(6) .0033(6) -.0016(6)
C7 .0158(8) .0218(8) .0145(7) -.0005(6) .0078(6) .0019(6)
C8 .0188(8) .0142(7) .0208(8) .0001(6) .0083(6) -.0020(6)
C9 .0118(7) .0185(7) .0166(7) .0026(5) .0016(6) .0020(6)
C10 .0124(7) .0223(8) .0189(8) .0044(6) .0034(6) .0039(6)
C11 .0164(8) .0193(8) .0192(8) .0014(6) .0099(6) .0031(6)
C12 .0159(7) .0141(7) .0204(8) -.0018(5) .0049(6) -.0023(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
O6 N3 O7 121.20(15) yes
O6 N3 C6 119.06(14) ?
O7 N3 C6 119.74(14) ?
O5 N2 O4 122.60(14) yes
O5 N2 C4 119.32(14) ?
O4 N2 C4 118.07(14) ?
O2 N1 O3 121.94(16) yes
O2 N1 C2 120.14(15) ?
O3 N1 C2 117.89(14) ?
C8 N4 C9 108.82(12) ?
C8 N4 C7 108.64(12) ?
C9 N4 C7 108.69(12) ?
C8 N4 H1N4 111.3(14) ?
C9 N4 H1N4 110.2(15) ?
C7 N4 H1N4 109.2(15) ?
C7 N5 C10 108.83(12) ?
C7 N5 C12 108.73(12) ?
C10 N5 C12 108.51(12) ?
C8 N6 C11 108.66(12) ?
C8 N6 C10 109.30(12) ?
C11 N6 C10 108.68(12) ?
C9 N7 C11 108.89(12) ?
C9 N7 C12 109.09(12) ?
C11 N7 C12 108.35(12) ?
O1 C1 C6 125.47(15) ?
O1 C1 C2 122.79(15) ?
C6 C1 C2 111.73(13) ?
C3 C2 C1 123.88(15) ?
C3 C2 N1 116.08(14) ?
C1 C2 N1 120.03(14) ?
C2 C3 C4 119.52(15) ?
C2 C3 H3A 120.2 ?
C4 C3 H3A 120.2 ?
C5 C4 C3 121.41(14) ?
C5 C4 N2 119.35(14) ?
C3 C4 N2 119.21(14) ?
C6 C5 C4 119.11(15) ?
C6 C5 H5A 120.4 ?
C4 C5 H5A 120.4 ?
C5 C6 N3 115.37(14) ?
C5 C6 C1 124.14(14) ?
N3 C6 C1 120.49(14) ?
N5 C7 N4 109.83(12) ?
N5 C7 H7A 109.7 ?
N4 C7 H7A 109.7 ?
N5 C7 H7B 109.7 ?
N4 C7 H7B 109.7 ?
H7A C7 H7B 108.2 ?
N6 C8 N4 109.58(12) ?
N6 C8 H8A 109.8 ?
N4 C8 H8A 109.8 ?
N6 C8 H8B 109.8 ?
N4 C8 H8B 109.8 ?
H8A C8 H8B 108.2 ?
N7 C9 N4 109.62(12) ?
N7 C9 H9A 109.7 ?
N4 C9 H9A 109.7 ?
N7 C9 H9B 109.7 ?
N4 C9 H9B 109.7 ?
H9A C9 H9B 108.2 ?
N6 C10 N5 111.90(12) ?
N6 C10 H10A 109.2 ?
N5 C10 H10A 109.2 ?
N6 C10 H10B 109.2 ?
N5 C10 H10B 109.2 ?
H10A C10 H10B 107.9 ?
N6 C11 N7 112.14(12) ?
N6 C11 H11A 109.2 ?
N7 C11 H11A 109.2 ?
N6 C11 H11B 109.2 ?
N7 C11 H11B 109.2 ?
H11A C11 H11B 107.9 ?
N7 C12 N5 112.13(12) ?
N7 C12 H12A 109.2 ?
N5 C12 H12A 109.2 ?
N7 C12 H12B 109.2 ?
N5 C12 H12B 109.2 ?
H12A C12 H12B 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.2456(19) yes
O2 N1 1.2037(19) yes
O3 N1 1.221(2) yes
O4 N2 1.2393(18) yes
O5 N2 1.2258(19) yes
O6 N3 1.226(2) yes
O7 N3 1.2262(18) yes
N3 C6 1.449(2) ?
N2 C4 1.4403(19) ?
N1 C2 1.467(2) ?
N4 C8 1.517(2) yes
N4 C9 1.5181(19) yes
N4 C7 1.519(2) yes
N4 H1N4 .94(3) ?
N5 C7 1.4488(19) yes
N5 C10 1.4737(19) yes
N5 C12 1.474(2) yes
N6 C8 1.446(2) yes
N6 C11 1.4719(19) yes
N6 C10 1.472(2) yes
N7 C9 1.4431(19) yes
N7 C11 1.4733(19) yes
N7 C12 1.474(2) yes
C1 C6 1.457(2) ?
C1 C2 1.464(2) ?
C2 C3 1.368(2) ?
C3 C4 1.386(2) ?
C3 H3A .9300 ?
C4 C5 1.383(2) ?
C5 C6 1.377(2) ?
C5 H5A .9300 ?
C7 H7A .9700 ?
C7 H7B .9700 ?
C8 H8A .9700 ?
C8 H8B .9700 ?
C9 H9A .9700 ?
C9 H9B .9700 ?
C10 H10A .9700 ?
C10 H10B .9700 ?
C11 H11A .9700 ?
C11 H11B .9700 ?
C12 H12A .9700 ?
C12 H12B .9700 ?
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
_geom_hbond_publ_flag
N4 H14N O1 1_555 .94(2) 1.81(3) 2.666(2) 152(2) yes
N4 H14N O7 1_555 .94(2) 2.26(2) 2.865(2) 122(2) yes
C12 H12A O7 1_565 .97 2.49 3.362(2) 149 yes
C12 H12B O4 1_665 .97 2.41 3.364(2) 167 yes
C5 H5A Cg 2_645 .93 3.30 4.07 142 yes
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
O1 C1 C2 C3 174.80(16)
C6 C1 C2 C3 -4.4(2)
O1 C1 C2 N1 -4.2(3)
C6 C1 C2 N1 176.62(14)
O2 N1 C2 C3 167.90(18)
O3 N1 C2 C3 -10.3(2)
O2 N1 C2 C1 -13.0(3)
O3 N1 C2 C1 168.81(18)
C1 C2 C3 C4 1.3(3)
N1 C2 C3 C4 -179.67(14)
C2 C3 C4 C5 2.5(2)
C2 C3 C4 N2 -175.61(15)
O5 N2 C4 C5 6.9(2)
O4 N2 C4 C5 -172.03(15)
O5 N2 C4 C3 -174.93(17)
O4 N2 C4 C3 6.1(2)
C3 C4 C5 C6 -2.6(3)
N2 C4 C5 C6 175.49(14)
C4 C5 C6 N3 179.64(14)
C4 C5 C6 C1 -1.0(3)
O6 N3 C6 C5 -4.9(2)
O7 N3 C6 C5 175.43(17)
O6 N3 C6 C1 175.74(16)
O7 N3 C6 C1 -3.9(3)
O1 C1 C6 C5 -174.91(17)
C2 C1 C6 C5 4.3(2)
O1 C1 C6 N3 4.4(3)
C2 C1 C6 N3 -176.45(14)
C10 N5 C7 N4 -59.11(16)
C12 N5 C7 N4 58.91(15)
C8 N4 C7 N5 59.14(15)
C9 N4 C7 N5 -59.12(15)
C11 N6 C8 N4 -59.31(16)
C10 N6 C8 N4 59.14(16)
C9 N4 C8 N6 59.25(16)
C7 N4 C8 N6 -58.93(15)
C11 N7 C9 N4 58.91(16)
C12 N7 C9 N4 -59.16(15)
C8 N4 C9 N7 -59.03(16)
C7 N4 C9 N7 59.12(15)
C8 N6 C10 N5 -60.44(16)
C11 N6 C10 N5 57.99(16)
C7 N5 C10 N6 60.22(16)
C12 N5 C10 N6 -57.94(16)
C8 N6 C11 N7 60.76(16)
C10 N6 C11 N7 -58.08(16)
C9 N7 C11 N6 -60.66(17)
C12 N7 C11 N6 57.88(16)
C9 N7 C12 N5 60.49(16)
C11 N7 C12 N5 -57.92(16)
C7 N5 C12 N7 -60.16(16)
C10 N5 C12 N7 58.06(16)