#------------------------------------------------------------------------------
#$Date: 2019-11-07 20:42:01 +0100 (jue 07 de nov de 2019) $
#$Revision: 223583 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/19/7231972.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_7231972
loop_
_publ_author_name
'Zhang, Tianhe'
'Du, Jiang'
'Li, Zhimin'
'Lin, Xinyu'
'Wang, Lin'
'Yang, Li'
'Zhang, Tonglai'
_publ_section_title
;
 Alkali metal salts of 3,6-dinitramino-1,2,4,5-tetrazine: promising
 nitrogen-rich energetic materials
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              765
_journal_paper_doi               10.1039/C8CE01827H
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C2 H2 N8 O4'
_chemical_formula_sum            'C2 H2 N8 O4'
_chemical_formula_weight         202.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-08-05 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4039(19)
_cell_length_b                   7.8696(16)
_cell_length_c                   9.4732(19)
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      2.5882
_cell_volume                     701.1(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4220
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         4.303
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.230
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0606
_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)+(0.0467P)²+0.8802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                762
_reflns_number_total             786
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    a.res created by SHELXL-2014/7

TITL A in Pbca
CELL 0.71073 9.4039 7.8696 9.4732 90 90 90
ZERR 4 0.0019 0.0016 0.0019 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 8 8 32 16
 
L.S. 4
PLAN  5
SIZE 0.08 0.05 0.02
TEMP -120
BOND
fmap 2
ACTA
BOND $H
CONF
OMIT 6 3 1
OMIT 7 2 2
REM <olex2.extras>
REM <HklSrc "%.\\A.hkl">
REM </olex2.extras>
 
WGHT    0.046700    0.880200
FVAR       0.73699
O1    4    0.733888   -0.146792    0.737001    11.00000    0.02996    0.03238 =
         0.02378    0.00586    0.00039    0.00242
O2    4    0.545684    0.009309    0.702153    11.00000    0.02123    0.03777 =
         0.03730    0.00046    0.01210    0.00387
N1    3    0.665302   -0.039883    0.672934    11.00000    0.02095    0.02425 =
         0.02215   -0.00236    0.00309   -0.00149
N2    3    0.724233    0.032467    0.553573    11.00000    0.01476    0.01843 =
         0.02553    0.00414    0.00423    0.00195
AFIX   3  0.8500
H2    2    0.690203    0.131627    0.542413    11.00000   -1.20000
AFIX   0
N3    3    0.942901    0.158638    0.516489    11.00000    0.01401    0.01719 =
         0.01945    0.00090    0.00168   -0.00122
N4    3    1.079842    0.143566    0.487078    11.00000    0.01550    0.01746 =
         0.01999   -0.00064    0.00193    0.00016
C1    1    0.869502    0.013956    0.529178    11.00000    0.01677    0.01553 =
         0.01645    0.00012   -0.00099    0.00059
HKLF 4
 
REM  A in Pbca
REM R1 =  0.0606 for     762 Fo > 4sig(Fo)  and  0.0640 for all     786 data
REM     64 parameters refined using      0 restraints
 
END  
     
WGHT      0.0467      0.8802 

REM Highest difference peak  0.254,  deepest hole -0.297,  1-sigma level  0.065
Q1    1   1.0518  0.1506  0.5182  11.00000  0.05    0.25
Q2    1   0.8892 -0.0573  0.5205  11.00000  0.05    0.24
Q3    1   0.9342  0.1684  0.4713  11.00000  0.05    0.21
Q4    1   0.4826  0.1460  0.5882  11.00000  0.05    0.19
Q5    1   0.8196  0.0224  0.5400  11.00000  0.05    0.19

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0606 for 762 Fo > 4sig(Fo) and 0.0640 for all 4785 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.25, deepest hole -0.30
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0640
  REM R1_gt = 0.0606
  REM wR_ref = 0.1402
  REM GOOF = 1.230
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4785
  REM Reflections_gt = 762
  REM Parameters = n/a
  REM Hole = -0.30
  REM Peak = 0.25
  REM Flack = n/a

  
;
_cod_data_source_file            c8ce01827h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7231971--7231978.cif.'
_cod_database_code               7231972
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Riding coordinates:
 N2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.7339(2) -0.1468(2) 0.73700(18) 0.0287(5) Uani 1 1 d .
O2 O 0.54568(19) 0.0093(2) 0.7022(2) 0.0321(5) Uani 1 1 d .
N1 N 0.6653(2) -0.0399(3) 0.6729(2) 0.0224(5) Uani 1 1 d .
N2 N 0.7242(2) 0.0325(3) 0.5536(2) 0.0196(5) Uani 1 1 d .
H2 H 0.6902 0.1316 0.5424 0.023 Uiso 1 1 d R
N3 N 0.94290(19) 0.1586(2) 0.51649(19) 0.0169(5) Uani 1 1 d .
N4 N 1.0798(2) 0.1436(2) 0.48708(19) 0.0177(5) Uani 1 1 d .
C1 C 0.8695(2) 0.0140(3) 0.5292(2) 0.0162(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0300(10) 0.0324(10) 0.0238(9) 0.0059(7) 0.0004(7) 0.0024(8)
O2 0.0212(10) 0.0378(11) 0.0373(11) 0.0005(8) 0.0121(8) 0.0039(8)
N1 0.0209(11) 0.0242(11) 0.0221(9) -0.0024(8) 0.0031(8) -0.0015(9)
N2 0.0148(10) 0.0184(10) 0.0255(10) 0.0041(8) 0.0042(7) 0.0020(8)
N3 0.0140(9) 0.0172(10) 0.0195(9) 0.0009(7) 0.0017(7) -0.0012(7)
N4 0.0155(9) 0.0175(10) 0.0200(9) -0.0006(7) 0.0019(7) 0.0002(8)
C1 0.0168(11) 0.0155(11) 0.0165(10) 0.0001(8) -0.0010(8) 0.0006(9)
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_site_symmetry_1
_geom_angle_site_symmetry_3
O1 N1 N2 118.59(19) . .
O2 N1 O1 126.3(2) . .
O2 N1 N2 115.1(2) . .
N1 N2 H2 109.2 . .
N1 N2 C1 119.07(18) . .
C1 N2 H2 116.4 . .
N4 N3 C1 116.43(19) . .
N3 N4 C1 117.02(19) . 5_756
N3 C1 N2 115.60(19) . .
N3 C1 N4 126.5(2) . 5_756
N4 C1 N2 117.7(2) 5_756 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.222(3) .
O2 N1 1.221(3) .
N1 N2 1.382(3) .
N2 H2 0.8500 .
N2 C1 1.393(3) .
N3 N4 1.323(3) .
N3 C1 1.337(3) .
N4 C1 1.337(3) 5_756
C1 N4 1.337(3) 5_756
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_site_symmetry_4
O1 N1 N2 C1 -15.4(3) .
O2 N1 N2 C1 165.9(2) .
N1 N2 C1 N3 -122.3(2) .
N1 N2 C1 N4 61.3(3) 5_756
N4 N3 C1 N2 -177.10(18) .
N4 N3 C1 N4 -1.1(3) 5_756
C1 N3 N4 C1 1.0(3) 5_756
