#------------------------------------------------------------------------------
#$Date: 2020-02-04 22:05:02 +0200 (Tue, 04 Feb 2020) $
#$Revision: 247595 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125623.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_7125623
loop_
_publ_author_name
'Liu, Tianlin'
'Liao, Sicheng'
'Song, Siwei'
'Wang, Kangcai'
'Jin, Yunhe'
'Zhang, Qinghua'
_publ_section_title
;
 Combination of gem-dinitromethyl functionality and a
 5-amino-1,3,4-oxadiazole framework for zwitterionic energetic materials.
;
_journal_issue                   2
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              209
_journal_page_last               212
_journal_paper_doi               10.1039/c9cc08182h
_journal_volume                  56
_journal_year                    2019
_chemical_formula_moiety         'C3 H3 N5 O5'
_chemical_formula_sum            'C3 H3 N5 O5'
_chemical_formula_weight         189.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_audit_update_record
;
2019-06-27 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2688(10)
_cell_length_b                   6.1121(7)
_cell_length_c                   13.2779(17)
_cell_measurement_reflns_used    2027
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      3.07
_cell_volume                     671.06(14)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3692
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.068
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0846 before and 0.0410 after correction. The Ratio of minimum to maximum transmission is 0.8906. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_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)+(0.0475P)²+0.0299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1367
_reflns_number_total             1436
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    mo_ltl-4-2-2_0ma.res created by SHELXL-2014/7

TITL mo_LTL-4-2-2_0ma in Pca2(1)
CELL 0.71073 8.2688 6.1121 13.2779 90 90 90
ZERR 4 0.001 0.0007 0.0017 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5-X,+Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SFAC C H N O
UNIT 12 12 20 20
 
L.S. 20
PLAN  -2 0 0
TEMP -100.15
HTAB
BOND $H
CONF
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\mo_LTL-4-2-2_0ma.hkl">
REM </olex2.extras>
 
WGHT    0.047500    0.029900
BASF   0.10811
FVAR       0.37566
O5    4   -0.246228    0.107425   -0.309301    11.00000    0.02291    0.02129 =
         0.01756   -0.00470    0.00266   -0.00313
O3    4   -0.347251   -0.274475   -0.577661    11.00000    0.03269    0.02914 =
         0.01674   -0.00609   -0.00106    0.00599
N4    3   -0.388049    0.016969   -0.179886    11.00000    0.02496    0.02354 =
         0.01568   -0.00288    0.00395    0.00192
O4    4   -0.470097   -0.023859   -0.490160    11.00000    0.03055    0.02846 =
         0.02276   -0.00447   -0.00648    0.01216
O2    4   -0.073849   -0.377102   -0.329793    11.00000    0.02514    0.03212 =
         0.02271    0.00244   -0.00539    0.00459
N1    3   -0.366665   -0.177211   -0.497481    11.00000    0.01962    0.01779 =
         0.01616   -0.00147    0.00001   -0.00067
N3    3   -0.400301   -0.157358   -0.245634    11.00000    0.02284    0.02286 =
         0.01725   -0.00286    0.00046    0.00045
O1    4   -0.117134   -0.485214   -0.482661    11.00000    0.04314    0.04591 =
         0.03216   -0.01691   -0.00748    0.02456
N5    3   -0.251224    0.358280   -0.180849    11.00000    0.04113    0.02464 =
         0.02365   -0.00904    0.00451   -0.00611
AFIX  93
H5A   2   -0.282992    0.396438   -0.120083    11.00000   -1.20000
H5B   2   -0.188872    0.446367   -0.216070    11.00000   -1.20000
AFIX   0
C3    1   -0.296275    0.172316   -0.218478    11.00000    0.02145    0.02400 =
         0.01644   -0.00227   -0.00161    0.00413
C2    1   -0.315209   -0.099212   -0.321617    11.00000    0.01599    0.01867 =
         0.01832   -0.00171   -0.00146    0.00064
C1    1   -0.280620   -0.222162   -0.411816    11.00000    0.01971    0.02101 =
         0.01680   -0.00273   -0.00076    0.00020
N2    3   -0.152726   -0.369930   -0.410360    11.00000    0.02292    0.02153 =
         0.02065   -0.00185   -0.00124    0.00293
H4    2   -0.429356    0.021532   -0.126573    11.00000    0.04402
HKLF 4
 
REM  mo_LTL-4-2-2_0ma in Pca2(1)
REM R1 =  0.0292 for    1367 Fo > 4sig(Fo)  and  0.0309 for all    1436 data
REM    123 parameters refined using      1 restraints
 
END  
     
WGHT      0.0475      0.0299 

REM Instructions for potential hydrogen bonds
EQIV $1 -x-1/2, y+1, z+1/2
HTAB N5 O1_$1
EQIV $2 x, y+1, z
HTAB N5 O2_$2
EQIV $3 -x-1, -y, z+1/2
HTAB N4 O3_$3
HTAB N4 O4_$3
HTAB N4 N1_$3

REM Highest difference peak  0.200,  deepest hole -0.183,  1-sigma level  0.051
Q1    1  -0.2867 -0.1675 -0.3624  11.00000  0.05    0.20
Q2    1   0.1426  0.6104  0.4589  11.00000  0.05    0.16

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0292 for 1367 Fo > 4sig(Fo) and 0.0309 for all 4111 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.20, deepest hole -0.18
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0309
  REM R1_gt = 0.0292
  REM wR_ref = 0.0779
  REM GOOF = 1.105
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4111
  REM Reflections_gt = 1367
  REM Parameters = n/a
  REM Hole = -0.18
  REM Peak = 0.20
  REM Flack = n/a

  
;
_cod_data_source_file            c9cc08182h2.cif
_cod_data_source_block           mo_ltl-4-2-2_0ma
_cod_depositor_comments
'Adding full bibliography for 7125621--7125624.cif.'
_cod_database_code               7125623
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(17)
 0.1(17)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
3.a X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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
O5 O -0.2462(2) 0.1074(3) -0.30930(13) 0.0206(4) Uani 1 1 d .
O3 O -0.3473(2) -0.2745(3) -0.57766(12) 0.0262(4) Uani 1 1 d .
N4 N -0.3880(2) 0.0170(3) -0.17989(15) 0.0214(4) Uani 1 1 d .
O4 O -0.4701(2) -0.0239(3) -0.49016(13) 0.0273(4) Uani 1 1 d .
O2 O -0.0738(2) -0.3771(3) -0.32979(12) 0.0267(4) Uani 1 1 d .
N1 N -0.3667(2) -0.1772(3) -0.49748(13) 0.0179(4) Uani 1 1 d .
N3 N -0.4003(3) -0.1574(3) -0.24563(14) 0.0210(4) Uani 1 1 d .
O1 O -0.1171(2) -0.4852(4) -0.48266(14) 0.0404(6) Uani 1 1 d .
N5 N -0.2512(3) 0.3583(3) -0.18085(17) 0.0298(5) Uani 1 1 d .
H5A H -0.2830 0.3964 -0.1201 0.036 Uiso 1 1 calc R
H5B H -0.1889 0.4464 -0.2161 0.036 Uiso 1 1 calc R
C3 C -0.2963(3) 0.1723(4) -0.21848(17) 0.0206(5) Uani 1 1 d .
C2 C -0.3152(3) -0.0992(4) -0.32162(17) 0.0177(4) Uani 1 1 d .
C1 C -0.2806(3) -0.2222(4) -0.41182(16) 0.0192(5) Uani 1 1 d .
N2 N -0.1527(3) -0.3699(3) -0.41036(15) 0.0217(4) Uani 1 1 d .
H4 H -0.429(5) 0.022(6) -0.127(3) 0.044(10) Uiso 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
O5 0.0229(8) 0.0213(9) 0.0176(7) -0.0047(6) 0.0027(6) -0.0031(7)
O3 0.0327(9) 0.0291(10) 0.0167(7) -0.0061(7) -0.0011(7) 0.0060(8)
N4 0.0250(11) 0.0235(11) 0.0157(9) -0.0029(7) 0.0040(7) 0.0019(8)
O4 0.0306(10) 0.0285(10) 0.0228(7) -0.0045(7) -0.0065(7) 0.0122(8)
O2 0.0251(9) 0.0321(11) 0.0227(9) 0.0024(7) -0.0054(7) 0.0046(7)
N1 0.0196(10) 0.0178(10) 0.0162(8) -0.0015(8) 0.0000(7) -0.0007(7)
N3 0.0228(9) 0.0229(11) 0.0173(9) -0.0029(7) 0.0005(7) 0.0004(8)
O1 0.0431(12) 0.0459(14) 0.0322(11) -0.0169(9) -0.0075(8) 0.0246(10)
N5 0.0411(13) 0.0246(11) 0.0236(10) -0.0090(9) 0.0045(9) -0.0061(9)
C3 0.0215(12) 0.0240(12) 0.0164(9) -0.0023(9) -0.0016(8) 0.0041(8)
C2 0.0160(10) 0.0187(11) 0.0183(10) -0.0017(8) -0.0015(8) 0.0006(8)
C1 0.0197(11) 0.0210(12) 0.0168(9) -0.0027(8) -0.0008(7) 0.0002(9)
N2 0.0229(11) 0.0215(11) 0.0207(9) -0.0019(7) -0.0012(8) 0.0029(8)
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
C3 O5 C2 104.36(19)
N3 N4 H4 124(3)
C3 N4 N3 110.61(19)
C3 N4 H4 125(3)
O3 N1 O4 120.65(18)
O3 N1 C1 123.65(19)
O4 N1 C1 115.69(19)
C2 N3 N4 104.1(2)
H5A N5 H5B 120.0
C3 N5 H5A 120.0
C3 N5 H5B 120.0
N4 C3 O5 108.4(2)
N5 C3 O5 121.3(2)
N5 C3 N4 130.3(2)
O5 C2 C1 119.19(19)
N3 C2 O5 112.6(2)
N3 C2 C1 128.2(2)
N1 C1 C2 118.8(2)
N1 C1 N2 122.5(2)
N2 C1 C2 118.52(19)
O2 N2 C1 115.48(19)
O1 N2 O2 121.5(2)
O1 N2 C1 123.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C3 1.335(3)
O5 C2 1.395(3)
O3 N1 1.230(2)
N4 N3 1.381(3)
N4 C3 1.319(3)
N4 H4 0.79(4)
O4 N1 1.273(2)
O2 N2 1.254(3)
N1 C1 1.369(3)
N3 C2 1.280(3)
O1 N2 1.227(3)
N5 H5A 0.8800
N5 H5B 0.8800
N5 C3 1.296(3)
C2 C1 1.443(3)
C1 N2 1.391(3)
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
O5 C2 C1 N1 -82.0(3)
O5 C2 C1 N2 93.2(3)
O3 N1 C1 C2 -179.2(2)
O3 N1 C1 N2 5.9(4)
N4 N3 C2 O5 0.1(2)
N4 N3 C2 C1 177.6(2)
O4 N1 C1 C2 1.4(3)
O4 N1 C1 N2 -173.6(2)
N1 C1 N2 O2 172.5(2)
N1 C1 N2 O1 -6.9(4)
N3 N4 C3 O5 0.2(3)
N3 N4 C3 N5 -178.1(3)
N3 C2 C1 N1 100.6(3)
N3 C2 C1 N2 -84.3(3)
C3 O5 C2 N3 0.1(3)
C3 O5 C2 C1 -177.8(2)
C3 N4 N3 C2 -0.1(2)
C2 O5 C3 N4 -0.1(2)
C2 O5 C3 N5 178.3(2)
C2 C1 N2 O2 -2.5(3)
C2 C1 N2 O1 178.1(2)
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(17)
2 0.1(17)
