#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009093.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_2009093
loop_
_publ_author_name
'Borbulevych, Oleg Ya.'
'Shishkin, Oleg V.'
'Knyazev, Victor N.'
_publ_section_title
4-Triethylammoniomethyl-1,3-dioxolane-2-spiro-1'-2',4',6'-trinitrocyclohexadienide
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1918
_journal_page_last               1920
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H22 N4 O8'
_chemical_formula_weight         386.37
_chemical_name_systematic
;
(4-triethylammoniomethyl-1,3-dioxolane)-2-spiro-1'-2',4',6'-trinitro-
cyclohexadienide
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.879(3)
_cell_length_b                   10.971(6)
_cell_length_c                   19.831(9)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     1713.8(14)
_computing_cell_refinement       'P3 (Siemens, 1989)'
_computing_data_collection       'P3 (Siemens, 1989)'
_computing_data_reduction        'XDISK (Siemens, 1991)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELXTL (Sheldrick, 1994)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1994)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'Syntex P2~1~/PC'
_diffrn_measurement_method       \q/2\q
_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  0.079
_diffrn_reflns_av_sigmaI/netI    0.21
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3223
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.876
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_restrained_S_obs      1.177
_refine_ls_R_factor_all          0.2099
_refine_ls_R_factor_gt           0.0771
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.1024P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.2640
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                1256
_reflns_number_total             2996
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bm1348.cif
_[local]_cod_data_source_block   k3002
_[local]_cod_cif_authors_sg_H-M  'P 21/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_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_cell_volume        1713.9(13)
_cod_database_code               2009093
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_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
N1 .051(3) .019(3) .041(3) -.003(2) -.011(2) .009(2)
N2 .042(3) .034(3) .028(2) .000(2) -.001(2) .006(2)
N3 .061(4) .036(3) .037(3) -.004(3) .008(3) -.007(2)
N4 .044(3) .046(3) .027(2) -.008(3) .000(2) .009(2)
O1 .074(3) .041(3) .042(2) -.005(2) .001(2) .020(2)
O2 .076(3) .026(3) .059(3) .010(2) -.003(2) .001(2)
O3 .073(3) .057(3) .034(2) .010(2) .013(2) -.004(2)
O4 .049(3) .038(2) .036(2) -.009(2) -.003(2) .015(2)
O5 .100(4) .016(2) .066(3) .008(2) .029(3) .004(2)
O6 .079(3) .038(3) .036(2) .004(2) .012(2) -.008(2)
O7 .043(2) .043(2) .017(2) -.012(2) -.001(2) .001(2)
O8 .039(2) .041(2) .026(2) -.004(2) -.005(2) .003(2)
C1 .033(3) .032(3) .029(3) -.003(3) -.006(2) .006(2)
C2 .029(3) .026(3) .028(3) -.004(2) -.006(2) .003(2)
C3 .038(3) .027(3) .026(3) .001(3) -.011(2) -.004(2)
C4 .032(3) .026(3) .022(3) -.004(3) -.005(2) .001(2)
C5 .035(3) .023(3) .028(3) -.002(2) -.003(2) .004(2)
C6 .042(3) .026(3) .028(3) .000(3) .000(3) .000(2)
C7 .064(5) .090(6) .025(3) -.031(4) -.004(3) .010(3)
C8 .043(4) .062(4) .025(3) -.015(3) .002(3) .005(3)
C9 .059(5) .076(5) .042(4) -.016(4) -.001(3) .007(4)
C10 .059(4) .042(4) .040(3) -.019(3) -.002(3) .001(3)
C11 .098(6) .030(4) .061(4) -.020(4) .009(4) -.002(3)
C12 .079(5) .010(3) .054(4) .003(3) -.010(3) .004(3)
C13 .072(5) .043(4) .053(4) .009(4) .005(4) -.008(3)
C14 .051(4) .019(3) .075(4) -.002(3) .009(3) -.022(3)
C15 .063(5) .024(3) .063(4) .001(3) .008(4) .008(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .7810(6) 1.7655(4) .3995(2) .0373(12) Uani d . 1 . N
N2 .6461(6) 1.4811(4) .5764(2) .0345(11) Uani d . 1 . N
N3 .9403(7) 1.3238(5) .3840(2) .0446(13) Uani d . 1 . N
N4 .6872(6) 1.5015(5) .1622(2) .0391(12) Uani d . 1 . N
O1 .8402(6) 1.7906(4) .3437(2) .0523(12) Uani d . 1 . O
O2 .7133(6) 1.8454(4) .4350(2) .0536(12) Uani d . 1 . O
O3 .6058(6) 1.5705(4) .6112(2) .0544(12) Uani d . 1 . O
O4 .6221(5) 1.3746(4) .5938(2) .0413(10) Uani d . 1 . O
O5 .9486(6) 1.2261(4) .4145(2) .0599(14) Uani d . 1 . O
O6 .9949(6) 1.3358(4) .3260(2) .0509(12) Uani d . 1 . O
O7 .7697(5) 1.5375(3) .3166(2) .0344(10) Uani d . 1 . O
O8 1.0343(5) 1.5798(3) .3618(2) .0355(10) Uani d . 1 . O
C1 .8667(7) 1.5465(5) .3781(2) .0313(13) Uani d . 1 . C
C2 .7894(7) 1.6436(5) .4245(2) .0280(12) Uani d . 1 . C
C3 .7242(7) 1.6213(5) .4859(2) .0305(13) Uani d . 1 . C
H3 .6796(7) 1.6865(5) .5116(2) .037 Uiso calc R 1 . H
C4 .7222(6) 1.5024(5) .5119(2) .0267(12) Uani d . 1 . C
C5 .7950(7) 1.4075(5) .4775(2) .0286(13) Uani d . 1 . C
H5 .7969(7) 1.3282(5) .4967(2) .034 Uiso calc R 1 . H
C6 .8648(7) 1.4269(5) .4158(3) .0321(13) Uani d . 1 . C
C7 .8705(9) 1.5841(8) .2616(3) .060(2) Uani d . 1 . C
H7 .8322(9) 1.6689(8) .2505(3) .072 Uiso calc R 1 . H
C8 1.0492(7) 1.5890(6) .2896(2) .043(2) Uani d . 1 . C
H8A 1.1171(7) 1.5205(6) .2720(2) .052 Uiso calc R 1 . H
H8B 1.1045(7) 1.6666(6) .2771(2) .052 Uiso calc R 1 . H
C9 .8573(8) 1.5103(7) .2012(3) .059(2) Uani d . 1 . C
H9A .8915(8) 1.4263(7) .2138(3) .071 Uiso calc R 1 . H
H9B .9427(8) 1.5409(7) .1695(3) .071 Uiso calc R 1 . H
C10 .5447(8) 1.4582(6) .2066(3) .047(2) Uani d . 1 . C
H10A .4380(8) 1.4591(6) .1794(3) .056 Uiso calc R 1 . H
H10B .5317(8) 1.5182(6) .2435(3) .056 Uiso calc R 1 . H
C11 .5641(10) 1.3312(6) .2386(3) .063(2) Uani d . 1 . C
H11A .465(3) 1.3138(17) .2662(18) .095 Uiso calc R 1 . H
H11B .667(3) 1.3290(13) .2670(17) .095 Uiso calc R 1 . H
H11C .572(6) 1.2697(7) .2029(3) .095 Uiso calc R 1 . H
C12 .7178(9) 1.4086(5) .1072(3) .048(2) Uani d . 1 . C
H12A .7570(9) 1.3320(5) .1289(3) .057 Uiso calc R 1 . H
H12B .6077(9) 1.3911(5) .0842(3) .057 Uiso calc R 1 . H
C13 .8438(9) 1.4431(6) .0544(3) .056(2) Uani d . 1 . C
H13A .846(4) 1.380(2) .0196(12) .084 Uiso calc R 1 . H
H13B .9569(13) 1.451(4) .0754(5) .084 Uiso calc R 1 . H
H13C .810(3) 1.521(2) .0337(15) .084 Uiso calc R 1 . H
C14 .6396(8) 1.6258(5) .1301(3) .048(2) Uani d . 1 . C
H14A .6210(8) 1.6851(5) .1669(3) .058 Uiso calc R 1 . H
H14B .7375(8) 1.6551(5) .1042(3) .058 Uiso calc R 1 . H
C15 .4881(8) 1.6260(5) .0851(3) .050(2) Uani d . 1 . C
H15A .470(3) 1.7081(10) .0668(16) .075 Uiso calc R 1 . H
H15B .3886(12) 1.602(4) .1107(6) .075 Uiso calc R 1 . H
H15C .505(2) 1.569(3) .0480(11) .075 Uiso calc R 1 . H
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O1 . . 1.241(6) no
N1 O2 . . 1.251(6) no
N1 C2 . . 1.428(7) yes
N2 O4 . . 1.234(6) no
N2 O3 . . 1.244(6) no
N2 C4 . . 1.444(7) yes
N3 O5 . . 1.232(6) no
N3 O6 . . 1.244(5) no
N3 C6 . . 1.430(7) yes
N4 C12 . . 1.516(7) yes
N4 C10 . . 1.518(7) yes
N4 C9 . . 1.537(8) yes
N4 C14 . . 1.548(8) yes
O7 C1 . . 1.429(6) yes
O7 C7 . . 1.456(7) yes
O8 C1 . . 1.414(6) yes
O8 C8 . . 1.444(6) yes
C1 C6 . . 1.510(7) yes
C1 C2 . . 1.542(7) yes
C2 C3 . . 1.353(7) yes
C3 C4 . . 1.402(7) yes
C4 C5 . . 1.377(7) yes
C5 C6 . . 1.369(7) yes
C7 C9 . . 1.447(9) no
C7 C8 . . 1.504(8) no
C10 C11 . . 1.537(8) no
C12 C13 . . 1.507(8) no
C14 C15 . . 1.475(9) no
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_publ_flag
O1 N1 O2 121.3(5) no
O1 N1 C2 120.2(5) no
O2 N1 C2 118.6(5) no
O4 N2 O3 123.3(4) no
O4 N2 C4 118.0(5) no
O3 N2 C4 118.7(5) no
O5 N3 O6 122.0(5) no
O5 N3 C6 119.4(5) no
O6 N3 C6 118.6(5) no
C12 N4 C10 109.7(5) no
C12 N4 C9 104.7(5) no
C10 N4 C9 112.0(4) no
C12 N4 C14 109.8(4) no
C10 N4 C14 109.8(5) no
C9 N4 C14 110.7(5) no
C1 O7 C7 109.0(4) yes
C1 O8 C8 109.9(4) yes
O8 C1 O7 108.0(4) yes
O8 C1 C6 110.9(4) no
O7 C1 C6 110.6(4) no
O8 C1 C2 109.9(4) no
O7 C1 C2 110.3(4) no
C6 C1 C2 107.3(4) yes
C3 C2 N1 117.8(5) no
C3 C2 C1 125.1(5) yes
N1 C2 C1 117.1(4) no
C2 C3 C4 120.4(5) yes
C5 C4 C3 120.9(5) yes
C5 C4 N2 120.1(5) no
C3 C4 N2 119.0(5) no
C6 C5 C4 120.3(5) yes
C5 C6 N3 116.7(5) no
C5 C6 C1 125.9(5) yes
N3 C6 C1 117.4(4) no
C9 C7 O7 113.1(5) no
C9 C7 C8 112.0(6) no
O7 C7 C8 104.9(4) yes
O8 C8 C7 105.6(4) yes
C7 C9 N4 119.9(6) no
N4 C10 C11 117.0(5) no
C13 C12 N4 116.6(5) no
C15 C14 N4 115.8(5) no
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_publ_flag
C8 O8 C1 O7 -1.9(6) yes
C8 O8 C1 C6 119.5(5) no
C8 O8 C1 C2 -122.1(5) no
C7 O7 C1 O8 -8.9(6) yes
C7 O7 C1 C6 -130.3(5) no
C7 O7 C1 C2 111.2(5) no
O1 N1 C2 C3 179.4(5) no
O2 N1 C2 C3 -0.4(7) no
O1 N1 C2 C1 -2.7(7) no
O2 N1 C2 C1 177.5(5) no
O8 C1 C2 C3 -124.0(5) no
O7 C1 C2 C3 117.1(5) no
C6 C1 C2 C3 -3.4(7) yes
O8 C1 C2 N1 58.3(6) no
O7 C1 C2 N1 -60.6(6) no
C6 C1 C2 N1 178.9(5) no
N1 C2 C3 C4 177.2(5) no
C1 C2 C3 C4 -0.5(8) no
C2 C3 C4 C5 3.9(8) yes
C2 C3 C4 N2 -177.7(5) no
O4 N2 C4 C5 -12.4(7) no
O3 N2 C4 C5 168.7(5) no
O4 N2 C4 C3 169.2(5) no
O3 N2 C4 C3 -9.7(7) no
C3 C4 C5 C6 -2.7(8) yes
N2 C4 C5 C6 178.9(5) no
C4 C5 C6 N3 179.0(5) no
C4 C5 C6 C1 -2.0(8) yes
O5 N3 C6 C5 -4.4(8) no
O6 N3 C6 C5 175.2(5) no
O5 N3 C6 C1 176.5(5) no
O6 N3 C6 C1 -3.9(7) no
O8 C1 C6 C5 124.6(6) no
O7 C1 C6 C5 -115.6(6) no
C2 C1 C6 C5 4.6(7) yes
O8 C1 C6 N3 -56.4(6) no
O7 C1 C6 N3 63.4(6) no
C2 C1 C6 N3 -176.4(4) no
C1 O7 C7 C9 137.8(6) no
C1 O7 C7 C8 15.4(7) yes
C1 O8 C8 C7 11.3(6) yes
C9 C7 C8 O8 -139.1(6) no
O7 C7 C8 O8 -16.1(7) yes
O7 C7 C9 N4 66.1(8) no
C8 C7 C9 N4 -175.6(5) no
C12 N4 C9 C7 -174.8(6) no
C10 N4 C9 C7 -55.9(8) no
C14 N4 C9 C7 67.0(7) no
C12 N4 C10 C11 54.8(6) no
C9 N4 C10 C11 -61.1(7) no
C14 N4 C10 C11 175.6(5) no
C10 N4 C12 C13 174.2(5) no
C9 N4 C12 C13 -65.4(6) no
C14 N4 C12 C13 53.4(7) no
C12 N4 C14 C15 58.5(7) no
C10 N4 C14 C15 -62.2(6) no
C9 N4 C14 C15 173.6(5) no
_journal_paper_doi 10.1107/S0108270199009233