#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/70/2237095.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_2237095
loop_
_publ_author_name
'Yan, Biao'
'Li, Hong-Ya'
'Zhao, Ning-Ning'
'Li, Jie'
'Ma, Hai-Xia'
_publ_section_title
;
 3,3-Dinitroazetidinium chloride
;
_journal_coeditor_code           ZQ2187
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3376
_journal_paper_doi               10.1107/S1600536812046302
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C3 H6 N3 O4 +, Cl -'
_chemical_formula_moiety         'C3 H6 N3 O4 +, Cl -'
_chemical_formula_sum            'C3 H6 Cl N3 O4'
_chemical_formula_weight         183.56
_chemical_name_systematic
;
3,3-Dinitroazetidinium chloride
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6807(17)
_cell_length_b                   10.4409(17)
_cell_length_c                   9.9707(19)
_cell_measurement_temperature    293(2)
_cell_volume                     695.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1968
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         3.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.162
_refine_ls_abs_structure_details 'Flack (1983), 252 Friedel pairs'
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_coef       0.227(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         708
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0313P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0549
_reflns_number_gt                696
_reflns_number_total             708
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2187.cif
_cod_data_source_block           I
_cod_database_code               2237095
_cod_database_fobs_code          2237095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
Cl Cl 0.0000 0.34257(4) 0.24339(6) 0.03211(19) Uani d S 1 2
N N2 0.0000 0.14030(15) 0.5026(2) 0.0277(4) Uani d S 1 2
O O3 0.0000 0.07128(19) 0.7449(3) 0.0571(6) Uani d S 1 2
C C1 0.1613(2) 0.35120(12) 0.57848(17) 0.0255(3) Uani d . 1 1
H H1A 0.2305 0.3773 0.6596 0.031 Uiso calc R 1 1
H H1B 0.2557 0.3293 0.5081 0.031 Uiso calc R 1 1
N N3 0.0000 0.1881(2) 0.7388(3) 0.0354(4) Uani d S 1 2
N N1 0.0000 0.44299(15) 0.5346(2) 0.0269(4) Uani d S 1 2
H H1C 0.0000 0.4581 0.4457 0.032 Uiso calc SR 1 2
H H1D 0.0000 0.5170 0.5808 0.032 Uiso calc SR 1 2
O O4 0.0000 0.2614(3) 0.8318(2) 0.0536(6) Uani d S 1 2
O O1 0.16253(18) 0.10036(10) 0.46749(16) 0.0425(4) Uani d . 1 1
C C2 0.0000 0.24966(18) 0.6017(2) 0.0217(4) Uani d S 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
Cl 0.0359(3) 0.0347(3) 0.0258(3) 0.000 0.000 0.0048(3)
N2 0.0314(9) 0.0207(8) 0.0309(11) 0.000 0.000 0.0002(7)
O3 0.0562(12) 0.0522(10) 0.0629(14) 0.000 0.000 0.0373(12)
C1 0.0226(7) 0.0236(7) 0.0304(8) -0.0015(5) 0.0008(6) -0.0013(5)
N3 0.0232(8) 0.0556(11) 0.0273(9) 0.000 0.000 0.0133(13)
N1 0.0323(10) 0.0202(7) 0.0283(9) 0.000 0.000 -0.0012(7)
O4 0.0463(12) 0.0904(16) 0.0240(9) 0.000 0.000 -0.0017(9)
O1 0.0365(7) 0.0362(6) 0.0549(9) 0.0117(4) -0.0002(7) -0.0136(6)
C2 0.0218(9) 0.0215(9) 0.0217(11) 0.000 0.000 0.0007(7)
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'
Cl Cl 0.1484 0.1585 '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
O1 N2 O1 4 . 126.74(19)
O1 N2 C2 4 . 116.63(9)
O1 N2 C2 . . 116.63(9)
N1 C1 C2 . . 88.89(11)
N1 C1 H1A . . 113.8
C2 C1 H1A . . 113.8
N1 C1 H1B . . 113.8
C2 C1 H1B . . 113.8
H1A C1 H1B . . 111.1
O4 N3 O3 . . 126.7(3)
O4 N3 C2 . . 115.2(2)
O3 N3 C2 . . 118.0(3)
C1 N1 C1 . 4 91.30(15)
C1 N1 H1C . . 113.4
C1 N1 H1D . . 113.4
H1C N1 H1D . . 110.7
N2 C2 N3 . . 105.67(17)
N2 C2 C1 . . 115.17(13)
N3 C2 C1 . . 115.58(13)
C1 C2 C1 . 4 89.62(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N2 O1 4 1.2147(14)
N2 O1 . 1.2147(14)
N2 C2 . 1.510(3)
O3 N3 . 1.221(3)
C1 N1 . 1.5073(18)
C1 C2 . 1.5294(19)
C1 H1A . 0.9700
C1 H1B . 0.9700
N3 O4 . 1.203(4)
N3 C2 . 1.511(3)
N1 C1 4 1.5073(19)
N1 H1C . 0.9000
N1 H1D . 0.9000
C2 C1 4 1.5294(19)
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
N1 H1C Cl . 0.90 2.35 3.087(2) 139 y
N1 H1D Cl 2_565 0.90 2.19 3.0575(19) 163 y
C1 H1B O1 . 0.97 2.50 2.8432(19) 100 ?
C1 H1B O4 7_554 0.97 2.58 3.543(2) 172 y
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 C1 N1 C1 . 4 8.66(17)
O1 N2 C2 N3 4 . 89.58(16)
O1 N2 C2 N3 . . -89.58(16)
O1 N2 C2 C1 4 . -141.56(16)
O1 N2 C2 C1 . . 39.3(2)
O1 N2 C2 C1 4 4 -39.3(2)
O1 N2 C2 C1 . 4 141.56(16)
O4 N3 C2 N2 . . 180.0
O3 N3 C2 N2 . . 0.0
O4 N3 C2 C1 . . 51.39(11)
O3 N3 C2 C1 . . -128.61(11)
O4 N3 C2 C1 . 4 -51.39(11)
O3 N3 C2 C1 . 4 128.61(11)
N1 C1 C2 N2 . . 109.30(15)
N1 C1 C2 N3 . . -126.93(15)
N1 C1 C2 C1 . 4 -8.53(17)
