#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/23/2012391.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_2012391
loop_
_publ_author_name
'Anwar Usman'
'Suchada Chantrapromma'
'Hoong-Kun Fun'
_publ_section_title
;
 The 143 and 300K polymorphs of hexamethylenetetraminium
 2,4-dinitrophenolate monohydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1443
_journal_page_last               1446
_journal_paper_doi               10.1107/S0108270101016742
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C6 H13 N4 1+, C6 H3 N2 O5 1-, H2 O'
_chemical_formula_moiety         'C6 H13 N4 1+, C6 H3 N2 O5 1-, H2 O'
_chemical_formula_sum            'C12 H18 N6 O6'
_chemical_formula_weight         342.32
_chemical_name_systematic
;
3,5,7-triaza-1-azoniatricyclo[3.3.1.1^3,7^]decane
2,4-dinitrophenolate monohydrate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 94.9150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8610(5)
_cell_length_b                   6.5980(4)
_cell_length_c                   14.4339(9)
_cell_measurement_reflns_used    3560
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      1.42
_cell_volume                     745.89(8)
_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      300(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .967
_diffrn_measured_fraction_theta_max .967
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  .0686
_diffrn_reflns_av_sigmaI/netI    .0957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5088
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .124
_exptl_absorpt_correction_T_max  .9757
_exptl_absorpt_correction_T_min  .9498
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .20
_refine_diff_density_max         .334
_refine_diff_density_min         -.313
_refine_ls_extinction_coef       .145(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   .948
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .948
_refine_ls_R_factor_all          .0743
_refine_ls_R_factor_gt           .0589
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0622P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1374
_refine_ls_wR_factor_ref         .1437
_reflns_number_gt                1288
_reflns_number_total             1900
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1495.cif
_cod_data_source_block           Iat300K
_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 

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_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2012391
_cod_database_fobs_code          2012391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
N1 .3354(3) .2500 .24704(13) .0402(5) Uani d S 1 . . N
N2 .0558(2) .2500 .53083(13) .0432(6) Uani d S 1 . . N
N3 .7478(2) .7500 .20852(12) .0325(5) Uani d S 1 . . N
H1N3 .727(4) .7500 .265(2) .047 Uiso d S 1 . . H
N4 .88545(17) .5660(2) .09159(9) .0337(4) Uani d . 1 . . N
N5 .6216(2) .7500 .04920(13) .0351(5) Uani d S 1 . . N
O1 .4692(3) .2500 .20695(11) .0526(6) Uani d S 1 . . O
O2 .1928(3) .2500 .20416(12) .0621(6) Uani d S 1 . . O
O3 -.0775(2) .2500 .48100(14) .0754(8) Uani d S 1 . . O
O4 .0538(2) .2500 .61478(13) .0811(9) Uani d S 1 . . O
O5 .3979(2) .2500 .63206(10) .0465(5) Uani d S 1 . . O
O1W .2668(3) .7500 .28182(14) .0585(6) Uani d S 1 . . O
H1W1 .379(4) .7500 .313(2) .060(9) Uiso d S 1 . . H
H2W1 .208(6) .7500 .318(3) .109(18) Uiso d S 1 . . H
C1 .3505(3) .2500 .34722(14) .0315(5) Uani d S 1 . . C
C2 .2036(3) .2500 .39233(15) .0341(6) Uani d S 1 . . C
H2A .100(3) .2500 .3631(18) .040(7) Uiso d S 1 . . H
C3 .2154(3) .2500 .48886(14) .0312(5) Uani d S 1 . . C
C4 .3758(3) .2500 .54426(14) .0317(5) Uani d S 1 . . C
C5 .5219(3) .2500 .49069(16) .0401(6) Uani d S 1 . . C
H5A .623(4) .2500 .522(2) .049(8) Uiso d S 1 . . H
C6 .5104(3) .2500 .39662(15) .0356(6) Uani d S 1 . . C
H6A .607(3) .2500 .3653(18) .045(7) Uiso d S 1 . . H
C7 .5830(3) .7500 .14533(17) .0393(6) Uani d S 1 . . C
H7A .516(2) .628(3) .1585(13) .045(5) Uiso d . 1 . . H
C8 .7247(2) .5697(3) .03182(12) .0390(4) Uani d . 1 . . C
H8A .655(2) .442(3) .0453(13) .047(5) Uiso d . 1 . . H
C9 .8499(2) .5642(3) .18767(11) .0353(4) Uani d . 1 . . C
H9B .957(2) .563(3) .2306(13) .045 Uiso d . 1 . . H
C10 .9820(3) .7500 .07362(16) .0368(6) Uani d S 1 . . C
H11A 1.009(3) .7500 .0117(19) .044 Uiso d S 1 . . H
H8B .754(2) .579(3) -.0316(15) .048(5) Uiso d . 1 . . H
H9A .784(3) .453(3) .2013(14) .053(6) Uiso d . 1 . . H
H11B 1.088(4) .7500 .1155(19) .045(7) Uiso d S 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 .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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 N1 O1 . . 122.4(2) yes
O2 N1 C1 . . 119.8(2) ?
O1 N1 C1 . . 117.9(2) ?
O4 N2 O3 . . 120.4(2) yes
O4 N2 C3 . . 120.4(2) ?
O3 N2 C3 . . 119.20(19) ?
C9 N3 C9 4_575 . 108.61(18) yes
C9 N3 C7 4_575 . 108.71(11) yes
C9 N3 C7 . . 108.71(11) yes
C9 N3 H1N3 4_575 . 110.0(10) ?
C9 N3 H1N3 . . 110.0(10) ?
C7 N3 H1N3 . . 111(2) ?
C9 N4 C10 . . 108.88(14) yes
C9 N4 C8 . . 109.75(14) yes
C10 N4 C8 . . 108.35(15) yes
C7 N5 C8 . 4_575 109.10(12) no
C7 N5 C8 . . 109.10(12) yes
C8 N5 C8 4_575 . 107.76(19) yes
H1W1 O1W H2W1 . . 106(4) no
C2 C1 C6 . . 121.11(19) ?
C2 C1 N1 . . 118.4(2) ?
C6 C1 N1 . . 120.51(19) ?
C1 C2 C3 . . 119.3(2) ?
C1 C2 H2A . . 123.4(16) ?
C3 C2 H2A . . 117.4(16) ?
C2 C3 C4 . . 122.66(19) ?
C2 C3 N2 . . 115.9(2) ?
C4 C3 N2 . . 121.47(18) ?
O5 C4 C3 . . 126.68(19) ?
O5 C4 C5 . . 119.4(2) ?
C3 C4 C5 . . 113.87(19) ?
C6 C5 C4 . . 123.5(2) ?
C6 C5 H5A . . 119.5(18) ?
C4 C5 H5A . . 117.1(18) ?
C5 C6 C1 . . 119.6(2) ?
C5 C6 H6A . . 120.6(17) ?
C1 C6 H6A . . 119.8(17) ?
N5 C7 N3 . . 109.74(18) yes
N5 C7 H7A . . 110.1(11) ?
N3 C7 H7A . . 109.0(11) ?
N4 C8 N5 . . 111.82(13) yes
N4 C8 H8A . . 108.6(11) ?
N5 C8 H8A . . 108.6(10) ?
N4 C8 H8B . . 106.9(12) ?
N5 C8 H8B . . 106.9(11) ?
H8A C8 H8B . . 114.0(15) ?
N4 C9 N3 . . 109.65(13) yes
N4 C9 H9B . . 112.0(10) ?
N3 C9 H9B . . 108.3(11) ?
N4 C9 H9A . . 111.7(12) ?
N3 C9 H9A . . 106.4(12) ?
H9B C9 H9A . . 108.7(16) ?
N4 C10 N4 . 4_575 111.77(18) yes
N4 C10 H11A . . 109.4(8) ?
N4 C10 H11A 4_575 . 109.4(8) ?
N4 C10 H11B . . 108.3(7) ?
N4 C10 H11B 4_575 . 108.3(7) ?
H11A C10 H11B . . 110(2) ?
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
N1 O2 . 1.234(3) yes
N1 O1 . 1.243(3) yes
N1 C1 . 1.441(3) yes
N2 O4 . 1.213(3) yes
N2 O3 . 1.219(3) yes
N2 C3 . 1.440(3) yes
N3 C9 4_575 1.510(2) no
N3 C9 . 1.510(2) yes
N3 C7 . 1.519(3) yes
N3 H1N3 . .85(3) no
N4 C9 . 1.438(2) yes
N4 C10 . 1.4666(19) yes
N4 C8 . 1.468(2) yes
N5 C7 . 1.446(3) yes
N5 C8 4_575 1.473(2) no
N5 C8 . 1.473(2) yes
O5 C4 . 1.264(3) yes
O1W H1W1 . .96(3) no
O1W H2W1 . .73(5) no
C1 C2 . 1.374(3) no
C1 C6 . 1.391(3) no
C2 C3 . 1.388(3) no
C2 H2A . .88(3) no
C3 C4 . 1.434(3) no
C4 C5 . 1.438(3) no
C5 C6 . 1.353(3) no
C5 H5A . .87(3) ?
C6 H6A . .91(3) ?
C7 H7A . .989(19) ?
C8 H8A . 1.029(19) ?
C8 H8B . .97(2) ?
C9 H9B . 1.00(2) ?
C9 H9A . .93(2) ?
C10 N4 4_575 1.4666(19) no
C10 H11A . .94(3) ?
C10 H11B . .99(3) ?
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
N3 H13N O5 2_656 .85(3) 1.85(3) 2.657(2) 159(3) yes
O1W H11W O5 2_656 .96(3) 1.86(3) 2.816(3) 177(3) yes
O1W H21W O4 2_556 .73(5) 2.35(5) 3.037(3) 159(5) yes
C5 H5A O3 1_655 .88(3) 2.48(3) 3.164(3) 135(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O2 N1 C1 C2 . . .0
O1 N1 C1 C2 . . 180.0
O2 N1 C1 C6 . . 180.0
O1 N1 C1 C6 . . .0
C6 C1 C2 C3 . . .0
N1 C1 C2 C3 . . 180.0
C1 C2 C3 C4 . . .0
C1 C2 C3 N2 . . 180.0
O4 N2 C3 C2 . . 180.0
O3 N2 C3 C2 . . .0
O4 N2 C3 C4 . . .0
O3 N2 C3 C4 . . 180.0
C2 C3 C4 O5 . . 180.0
N2 C3 C4 O5 . . .0
C2 C3 C4 C5 . . .0
N2 C3 C4 C5 . . 180.0
O5 C4 C5 C6 . . 180.0
C3 C4 C5 C6 . . .0
C4 C5 C6 C1 . . .0
C2 C1 C6 C5 . . .0
N1 C1 C6 C5 . . 180.0
C8 N5 C7 N3 4_575 . -58.75(12)
C8 N5 C7 N3 . . 58.75(12)
C9 N3 C7 N5 4_575 . 59.03(10)
C9 N3 C7 N5 . . -59.03(10)
C9 N4 C8 N5 . . 59.88(18)
C10 N4 C8 N5 . . -58.89(18)
C7 N5 C8 N4 . . -59.55(19)
C8 N5 C8 N4 4_575 . 58.8(2)
C10 N4 C9 N3 . . 59.37(19)
C8 N4 C9 N3 . . -59.07(18)
C9 N3 C9 N4 4_575 . -59.2(2)
C7 N3 C9 N4 . . 58.92(18)
C9 N4 C10 N4 . 4_575 -60.7(2)
C8 N4 C10 N4 . 4_575 58.6(2)
