# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1529753'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Dinitro-1,3-pentadiene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N2 O4'
_chemical_formula_sum            'C5 H6 N2 O4'
_chemical_formula_weight         158.12

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'
_symmetry_Int_Tables_number      14


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0360(7)
_cell_length_b                   10.7787(8)
_cell_length_c                   10.9735(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.546(10)
_cell_angle_gamma                90.00
_cell_volume                     711.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5955
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.11

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Stoe Image plate diffraction system'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5955
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         28.11
_reflns_number_total             1712
_reflns_number_gt                1275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1712
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67633(18) -0.16942(10) -0.26809(10) 0.0591(3) Uani 1 1 d . . .
O2 O 0.82680(15) 0.01208(10) -0.24241(9) 0.0533(3) Uani 1 1 d . . .
O3 O -0.10550(16) 0.17130(9) 0.03737(10) 0.0559(3) Uani 1 1 d . . .
O4 O -0.02729(17) 0.36474(10) 0.05858(11) 0.0590(3) Uani 1 1 d . . .
N1 N 0.67343(16) -0.06039(10) -0.23480(8) 0.0394(3) Uani 1 1 d . . .
N2 N 0.01618(16) 0.26031(9) 0.02551(9) 0.0377(2) Uani 1 1 d . . .
C1 C 0.47348(19) -0.01992(12) -0.18056(10) 0.0371(3) Uani 1 1 d . . .
C2 C 0.45216(18) 0.09487(11) -0.14157(9) 0.0339(3) Uani 1 1 d . . .
C3 C 0.25634(18) 0.13172(11) -0.08235(10) 0.0337(3) Uani 1 1 d . . .
C4 C 0.22758(17) 0.24267(10) -0.03342(10) 0.0335(2) Uani 1 1 d . . .
C5 C 0.3742(2) 0.35309(14) -0.02748(16) 0.0520(4) Uani 1 1 d . . .
H1 H 0.369(2) -0.0876(14) -0.1761(12) 0.042(3) Uiso 1 1 d . . .
H2 H 0.564(2) 0.1512(13) -0.1491(13) 0.042(4) Uiso 1 1 d . . .
H3 H 0.145(2) 0.0712(14) -0.0805(12) 0.044(4) Uiso 1 1 d . . .
H5A H 0.419(3) 0.3718(18) 0.058(2) 0.082(6) Uiso 1 1 d . . .
H5B H 0.292(4) 0.424(2) -0.0582(19) 0.091(6) Uiso 1 1 d . . .
H5C H 0.514(4) 0.3360(16) -0.0668(18) 0.075(5) 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
O1 0.0636(6) 0.0483(6) 0.0679(6) -0.0205(5) 0.0207(5) 0.0048(5)
O2 0.0394(5) 0.0603(7) 0.0624(6) -0.0060(4) 0.0174(4) -0.0035(4)
O3 0.0457(5) 0.0492(6) 0.0766(7) 0.0017(4) 0.0293(5) -0.0073(4)
O4 0.0488(5) 0.0477(6) 0.0827(7) -0.0192(5) 0.0186(5) 0.0054(4)
N1 0.0404(5) 0.0442(6) 0.0344(5) -0.0038(4) 0.0083(4) 0.0025(4)
N2 0.0344(5) 0.0395(6) 0.0400(5) -0.0013(4) 0.0075(4) 0.0024(4)
C1 0.0364(6) 0.0388(6) 0.0374(5) -0.0025(4) 0.0110(4) -0.0019(5)
C2 0.0316(5) 0.0359(6) 0.0349(5) 0.0007(4) 0.0060(4) -0.0024(4)
C3 0.0310(5) 0.0331(6) 0.0375(5) 0.0005(4) 0.0059(4) -0.0026(4)
C4 0.0294(5) 0.0345(6) 0.0373(5) 0.0016(4) 0.0074(4) 0.0002(4)
C5 0.0452(7) 0.0388(8) 0.0746(10) -0.0099(6) 0.0209(6) -0.0082(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2311(14) . ?
O2 N1 1.2192(14) . ?
O3 N2 1.2215(13) . ?
O4 N2 1.2176(13) . ?
N1 C1 1.4543(14) . ?
N2 C4 1.4878(14) . ?
C1 C2 1.3188(17) . ?
C1 H1 0.967(15) . ?
C2 C3 1.4488(15) . ?
C2 H2 0.918(15) . ?
C3 C4 1.3279(16) . ?
C3 H3 0.939(15) . ?
C4 C5 1.4814(17) . ?
C5 H5A 0.98(2) . ?
C5 H5B 0.95(2) . ?
C5 H5C 0.99(2) . ?

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
_geom_angle_publ_flag
O2 N1 O1 124.23(10) . . ?
O2 N1 C1 119.67(11) . . ?
O1 N1 C1 116.07(10) . . ?
O4 N2 O3 123.29(10) . . ?
O4 N2 C4 117.40(10) . . ?
O3 N2 C4 119.31(10) . . ?
C2 C1 N1 121.31(11) . . ?
C2 C1 H1 127.6(8) . . ?
N1 C1 H1 111.1(8) . . ?
C1 C2 C3 120.45(11) . . ?
C1 C2 H2 120.0(9) . . ?
C3 C2 H2 119.5(9) . . ?
C4 C3 C2 124.45(10) . . ?
C4 C3 H3 120.0(9) . . ?
C2 C3 H3 115.6(9) . . ?
C3 C4 C5 130.13(11) . . ?
C3 C4 N2 115.79(10) . . ?
C5 C4 N2 114.08(10) . . ?
C4 C5 H5A 109.0(11) . . ?
C4 C5 H5B 109.5(13) . . ?
H5A C5 H5B 105.8(17) . . ?
C4 C5 H5C 110.9(10) . . ?
H5A C5 H5C 106.0(16) . . ?
H5B C5 H5C 115.4(17) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C2 1.49(17) . . . . ?
O1 N1 C1 C2 179.95(11) . . . . ?
N1 C1 C2 C3 -176.94(10) . . . . ?
C1 C2 C3 C4 175.47(11) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 N2 -178.63(10) . . . . ?
O4 N2 C4 C3 -171.68(11) . . . . ?
O3 N2 C4 C3 7.59(16) . . . . ?
O4 N2 C4 C5 8.55(16) . . . . ?
O3 N2 C4 C5 -172.19(12) . . . . ?


#--------------------Hydrogen bonding scheme-----------------------------# 

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag


#
# Hydrogen bonding scheme
# ======== ======= ======
#
#  D   H   A   D-H       H...A     D...A      D-H...A    symm  publ
#  -   -   -   ---       -----     -----      -------    ----  ----

C1 H1 O3 0.967(15) 2.460(14) 3.2585(15) 139.8(11) 3_555 yes
C2 H2 O1 0.918(15) 2.691(15) 3.5804(15) 163.5(12) 2_654 yes
C3 H3 O3 0.939(15) 2.670(15) 3.4368(15) 139.3(11) 3_555 yes
C3 H3 O2 0.939(15) 2.589(14) 3.2785(15) 130.5(11) 1_455 yes
C5 H5A O2 0.98(2) 2.62(2) 3.4816(19) 147.3(15) 4_566 yes
C5 H5B O4 0.95(2) 2.79(2) 3.693(2) 159.2(17) 3_565 yes
C5 H5C O1 0.99(2) 2.71(2) 3.6630(18) 161.7(15) 2_654 yes


_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.11
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.037


_iucr_refine_instruction_details 
;
#---------------------------------------------------------

TITL ip1715 in P2(1)/n
CELL  0.71073   6.0360  10.7787  10.9735   90.000   94.546   90.000
ZERR     4.00   0.0007   0.0008   0.0010    0.000    0.010    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  20   24   8    16
MERG   2
FMAP   2
PLAN    8
SIZE     0.23   0.26   0.27
ACTA
BOND
BOND   $H
CONF
 
EQIV $1 -X, -Y, -Z
EQIV $2 1.5-X, 0.5+Y, -0.5-Z
EQIV $3 -1+X, Y, Z
EQIV $4 -0.5+X, 0.5-Y, 0.5+Z
EQIV $5 -X, 1-Y, -Z
EQIV $6 0.5+X, 0.5-Y, -0.5+Z
EQIV $7 0.5-X, 0.5+Y, -0.5-Z
EQIV $8 1-X, -Y, -Z
 
RTAB XHY C1 H1 O3_$1
RTAB XHY C2 H2 O1_$2
RTAB XHY C3 H3 O3_$1
RTAB XHY C3 H3 O2_$3
RTAB XHY C5 H5A O2_$4
RTAB XHY C5 H5B O4_$5
RTAB XHY C5 H5C O1_$2
 
RTAB H..O H1 O3_$1
RTAB H..O H2 O1_$2
RTAB H..O H3 O3_$1
RTAB H..O H3 O2_$3
RTAB H..O H5A O2_$4
RTAB H..O H5B O4_$5
RTAB H..O H5C O1_$2
 
RTAB O..O C1 O3_$1
RTAB O..O C2 O1_$2
RTAB O..O C3 O3_$1
RTAB O..O C3 O2_$3
RTAB O..O C5 O2_$4
RTAB O..O C5 O4_$5
RTAB O..O C5 O1_$2
 
RTAB O..O N1 O4_$6
RTAB O..O N2 O1_$7
RTAB O..O N2 O1_$8
 
MPLA 4 C1 N1 O1 O2 O4_$6
MPLA 4 C4 N2 O3 O4 O1_$7 O1_$8
 
LIST   4
L.S.   4
TEMP   -60.00
WGHT    0.068300
FVAR       1.56646
O1    4    0.676327   -0.169417   -0.268086    11.00000    0.06364    0.04827 =
         0.06788   -0.02052    0.02068    0.00480
O2    4    0.826797    0.012078   -0.242412    11.00000    0.03939    0.06027 =
         0.06241   -0.00597    0.01743   -0.00354
O3    4   -0.105505    0.171298    0.037370    11.00000    0.04574    0.04923 =
         0.07657    0.00168    0.02932   -0.00731
O4    4   -0.027288    0.364743    0.058578    11.00000    0.04884    0.04774 =
         0.08268   -0.01916    0.01862    0.00542
N1    3    0.673431   -0.060395   -0.234800    11.00000    0.04038    0.04418 =
         0.03440   -0.00382    0.00826    0.00247
N2    3    0.016177    0.260315    0.025512    11.00000    0.03438    0.03949 =
         0.04002   -0.00129    0.00752    0.00244
C1    1    0.473476   -0.019917   -0.180564    11.00000    0.03642    0.03877 =
         0.03741   -0.00250    0.01096   -0.00185
C2    1    0.452163    0.094867   -0.141569    11.00000    0.03156    0.03586 =
         0.03487    0.00068    0.00598   -0.00242
C3    1    0.256339    0.131722   -0.082353    11.00000    0.03103    0.03311 =
         0.03745    0.00053    0.00586   -0.00265
C4    1    0.227581    0.242665   -0.033423    11.00000    0.02937    0.03447 =
         0.03730    0.00156    0.00740    0.00020
C5    1    0.374168    0.353091   -0.027482    11.00000    0.04523    0.03882 =
         0.07461   -0.00986    0.02090   -0.00818
H1    2    0.369147   -0.087558   -0.176115    11.00000    0.04220
H2    2    0.564253    0.151190   -0.149084    11.00000    0.04217
H3    2    0.144705    0.071173   -0.080498    11.00000    0.04389
H5A   2    0.418781    0.371755    0.058172    11.00000    0.08163
H5B   2    0.292256    0.423528   -0.058219    11.00000    0.09056
H5C   2    0.513873    0.336006   -0.066755    11.00000    0.07455
HKLF    4
 
REM  ip1715 in P2(1)/n
REM R1 =  0.0357 for   1275 Fo > 4sig(Fo)  and  0.0470 for all   1712 data
REM    124 parameters refined using      0 restraints
 
END
 
WGHT      0.0683      0.0000
REM Highest difference peak  0.221,  deepest hole -0.148,  1-sigma level  0.037
Q1    1   0.2064  0.1993 -0.0920  11.00000  0.05    0.22
Q2    1   0.3440  0.1147 -0.1163  11.00000  0.05    0.22
Q3    1   0.6316 -0.1240 -0.3149  11.00000  0.05    0.20
Q4    1   0.2905  0.1819 -0.0266  11.00000  0.05    0.20
Q5    1   0.4955  0.0224 -0.1236  11.00000  0.05    0.20
Q6    1   0.1398  0.2526 -0.0072  11.00000  0.05    0.19
Q7    1   0.5593 -0.0353 -0.1983  11.00000  0.05    0.19
Q8    1   0.4174  0.0436 -0.1957  11.00000  0.05    0.18
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 1529752'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Dinitro-1,3-butadiene 1,4-Dioxane (1/1) solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N2 O4, C4 H8 O2'
_chemical_formula_sum            'C8 H12 N2 O6'
_chemical_formula_weight         232.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_symmetry_Int_Tables_number      14


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'

_cell_length_a                   8.3219(7)
_cell_length_b                   5.2142(4)
_cell_length_c                   12.3799(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.819(12)
_cell_angle_gamma                90.00
_cell_volume                     537.13(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    4448
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      27.99

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Stoe Image plate diffraction system'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4448
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.99
_reflns_number_total             1266
_reflns_number_gt                986
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.40(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.02710(10) -0.02751(14) 0.16785(6) 0.0410(2) Uani 1 1 d . . .
O2 O 0.24259(11) 0.12941(15) 0.24151(6) 0.0469(3) Uani 1 1 d . . .
N1 N 0.13002(10) 0.13904(14) 0.17699(6) 0.0309(2) Uani 1 1 d . . .
C1 C 0.12010(12) 0.36392(17) 0.10809(8) 0.0312(2) Uani 1 1 d . . .
C2 C 0.00518(11) 0.38832(17) 0.03479(7) 0.0279(2) Uani 1 1 d . . .
H1 H 0.2005(17) 0.486(3) 0.1221(10) 0.044(3) Uiso 1 1 d . . .
H2 H -0.0736(15) 0.266(2) 0.0278(9) 0.035(3) Uiso 1 1 d . . .
O3 O 0.36403(9) 0.84654(15) 0.02012(6) 0.0397(2) Uani 1 1 d . . .
C4 C 0.40472(14) 0.9215(2) -0.08718(8) 0.0392(3) Uani 1 1 d . . .
C5 C 0.50584(13) 0.8281(2) 0.08555(8) 0.0369(3) Uani 1 1 d . . .
H4A H 0.3057(17) 0.935(2) -0.1263(11) 0.043(3) Uiso 1 1 d . . .
H4B H 0.4717(17) 0.789(3) -0.1205(10) 0.044(3) Uiso 1 1 d . . .
H5A H 0.5749(17) 0.696(3) 0.0562(10) 0.040(3) Uiso 1 1 d . . .
H5B H 0.4737(16) 0.786(3) 0.1600(10) 0.043(3) 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
O1 0.0567(5) 0.0308(4) 0.0356(4) 0.0028(3) 0.0019(3) -0.0091(3)
O2 0.0463(5) 0.0551(5) 0.0389(4) 0.0019(3) -0.0110(3) 0.0099(4)
N1 0.0366(5) 0.0310(4) 0.0251(4) -0.0025(3) 0.0018(3) 0.0033(3)
C1 0.0328(5) 0.0290(5) 0.0320(5) 0.0003(3) 0.0007(3) -0.0058(4)
C2 0.0294(5) 0.0272(5) 0.0272(4) -0.0016(3) 0.0035(3) -0.0052(3)
O3 0.0305(4) 0.0490(4) 0.0397(4) 0.0092(3) -0.0026(3) -0.0136(3)
C4 0.0362(6) 0.0461(6) 0.0351(5) 0.0039(4) -0.0056(4) -0.0110(5)
C5 0.0338(6) 0.0389(5) 0.0378(5) 0.0093(4) -0.0024(4) -0.0047(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2238(11) . ?
O2 N1 1.2234(11) . ?
N1 C1 1.4517(12) . ?
C1 C2 1.3151(14) . ?
C1 H1 0.937(14) . ?
C2 C2 1.4504(17) 3_565 ?
C2 H2 0.919(12) . ?
O3 C5 1.4251(12) . ?
O3 C4 1.4300(12) . ?
C4 C5 1.5028(14) 3_675 ?
C4 H4A 0.952(14) . ?
C4 H4B 0.984(14) . ?
C5 H5A 0.970(14) . ?
C5 H5B 0.989(12) . ?

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
_geom_angle_publ_flag
O2 N1 O1 124.03(8) . . ?
O2 N1 C1 116.96(8) . . ?
O1 N1 C1 119.01(8) . . ?
C2 C1 N1 121.22(8) . . ?
C2 C1 H1 124.9(8) . . ?
N1 C1 H1 113.9(8) . . ?
C1 C2 C2 121.60(10) . 3_565 ?
C1 C2 H2 120.5(7) . . ?
C2 C2 H2 117.8(7) 3_565 . ?
C5 O3 C4 109.95(8) . . ?
O3 C4 C5 110.41(9) . 3_675 ?
O3 C4 H4A 106.1(8) . . ?
C5 C4 H4A 111.5(8) 3_675 . ?
O3 C4 H4B 109.9(7) . . ?
C5 C4 H4B 109.5(8) 3_675 . ?
H4A C4 H4B 109.3(11) . . ?
O3 C5 C4 110.80(8) . 3_675 ?
O3 C5 H5A 109.0(7) . . ?
C4 C5 H5A 109.0(8) 3_675 . ?
O3 C5 H5B 108.2(8) . . ?
C4 C5 H5B 108.8(8) 3_675 . ?
H5A C5 H5B 111.1(11) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C2 178.56(9) . . . . ?
O1 N1 C1 C2 -1.62(13) . . . . ?
N1 C1 C2 C2 -179.67(10) . . . 3_565 ?
C5 O3 C4 C5 -57.45(13) . . . 3_675 ?
C4 O3 C5 C4 57.68(13) . . . 3_675 ?



#--------------------Hydrogen bonding scheme-----------------------------# 

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag


#
# Hydrogen bonding scheme
# ======== ======= ======
#
#  D   H   A   D-H       H...A     D...A      D-H...A    symm  publ
#  -   -   -   ---       -----     -----      -------    ----  ----

C1 H1 O3 0.937(14) 2.652(14) 3.4209(12) 139.7(10) . yes
C2 H2 O3 0.919(12) 2.548(13) 3.3678(12) 148.7(10) 3_565 yes



_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031



_iucr_refine_instruction_details 
;
#---------------------------------------------------------

TITL ip1720 in P2(1)/c
CELL  0.71073   8.3219   5.2142  12.3799   90.000   90.819   90.000
ZERR     2.00   0.0007   0.0004   0.0013    0.000    0.012    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  16   24   4    12
MERG   2
EQIV $1 -X, 1-Y, -Z
EQIV $2 -X, 0.5+Y, 0.5-Z
EQIV $3 X, -1+Y, Z
RTAB XHY C1 H1 O3
RTAB XHY C2 H2 O3_$1
RTAB H..O H1 O3
RTAB H..O H2 O3_$1
RTAB O..O C1 O3
RTAB O..O C2 O3_$1
RTAB O..O N1 O1_$2
RTAB O..O N1 O3_$3
MPLA 4 C1 N1 O1 O2 O1_$2 O3_$3
FMAP   2
PLAN    8
SIZE     0.24   0.24   0.28
ACTA
BOND
BOND   $H
CONF
LIST   4
L.S.   5
TEMP   -60.00
WGHT    0.057000
EXTI    0.399618
FVAR       2.42290
MOLE    1
O1    4    0.027102   -0.027511    0.167848    11.00000    0.05667    0.03085 =
         0.03559    0.00278    0.00193   -0.00912
O2    4    0.242588    0.129410    0.241513    11.00000    0.04631    0.05511 =
         0.03890    0.00195   -0.01097    0.00990
N1    3    0.130022    0.139036    0.176991    11.00000    0.03661    0.03097 =
         0.02513   -0.00251    0.00179    0.00328
C1    1    0.120103    0.363916    0.108090    11.00000    0.03277    0.02901 =
         0.03197    0.00029    0.00072   -0.00578
C2    1    0.005182    0.388321    0.034791    11.00000    0.02939    0.02717 =
         0.02718   -0.00161    0.00348   -0.00518
H1    2    0.200454    0.485828    0.122092    11.00000    0.04400
H2    2   -0.073596    0.265542    0.027822    11.00000    0.03459
MOLE    2
O3    4    0.364026    0.846538    0.020117    11.00000    0.03046    0.04896 =
         0.03965    0.00918   -0.00264   -0.01362
C4    1    0.404724    0.921484   -0.087183    11.00000    0.03618    0.04614 =
         0.03511    0.00389   -0.00558   -0.01104
C5    1    0.505844    0.828121    0.085548    11.00000    0.03385    0.03887 =
         0.03782    0.00931   -0.00238   -0.00471
H4A   2    0.305706    0.935301   -0.126273    11.00000    0.04276
H4B   2    0.471676    0.788541   -0.120516    11.00000    0.04373
H5A   2    0.574936    0.696203    0.056228    11.00000    0.03986
H5B   2    0.473651    0.785710    0.160014    11.00000    0.04323
HKLF    4
 
REM  ip1720 in P2(1)/c
REM R1 =  0.0301 for    986 Fo > 4sig(Fo)  and  0.0383 for all   1266 data
REM     98 parameters refined using      0 restraints
 
END
 
WGHT      0.0570      0.0000
REM Highest difference peak  0.196,  deepest hole -0.142,  1-sigma level  0.031
Q1    1   0.0000  0.5000  0.0000  10.50000  0.05    0.20
Q2    1   0.4518  1.0423 -0.0881  11.00000  0.05    0.19
Q3    1   0.1283  0.2609  0.1387  11.00000  0.05    0.18
Q4    1   0.1012  0.3376  0.0494  11.00000  0.05    0.16
Q5    1   0.3771  0.8834 -0.0286  11.00000  0.05    0.14
Q6    1   0.2843  0.2596  0.1989  11.00000  0.05    0.13
Q7    1   0.0244  0.4215  0.0901  11.00000  0.05    0.13
Q8    1   0.0484 -0.0907  0.0987  11.00000  0.05    0.11

;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1529754'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,4-Dinitro-2,4-hexadiene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 N2 O4'
_chemical_formula_weight         172.14

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'
_symmetry_Int_Tables_number      14


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.4312(8)
_cell_length_b                   6.1004(10)
_cell_length_c                   12.3902(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.006(5)
_cell_angle_gamma                90.00
_cell_volume                     402.97(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4576
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      28.68

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9239
_exptl_absorpt_correction_T_max  0.9372
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 area-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4576
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         28.68
_reflns_number_total             1038
_reflns_number_gt                666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#  


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.77(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1038
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6867(2) 0.0671(2) 0.27610(9) 0.0578(5) Uani 1 1 d . . .
O2 O 0.3842(2) 0.2859(2) 0.28481(9) 0.0556(5) Uani 1 1 d . . .
N1 N 0.5025(3) 0.1709(2) 0.23258(10) 0.0406(4) Uani 1 1 d . . .
C1 C 0.4172(3) 0.1601(3) 0.11215(11) 0.0410(5) Uani 1 1 d . . .
C2 C 0.5308(3) 0.0160(3) 0.05884(12) 0.0392(4) Uani 1 1 d . . .
C3 C 0.2111(7) 0.3117(6) 0.06990(19) 0.0847(10) Uani 1 1 d . . .
H2 H 0.656(3) -0.073(3) 0.0981(15) 0.048(5) Uiso 1 1 d . . .
H3A H 0.167(5) 0.304(5) -0.006(3) 0.113(9) Uiso 1 1 d . . .
H3B H 0.263(5) 0.443(5) 0.089(2) 0.102(11) Uiso 1 1 d . . .
H3C H 0.069(7) 0.293(5) 0.101(3) 0.124(12) 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
O1 0.0684(9) 0.0656(9) 0.0331(6) -0.0029(6) -0.0059(6) 0.0184(7)
O2 0.0709(9) 0.0622(8) 0.0356(6) -0.0098(6) 0.0155(6) 0.0087(6)
N1 0.0534(9) 0.0400(8) 0.0277(6) -0.0027(5) 0.0057(6) 0.0000(6)
C1 0.0489(10) 0.0469(9) 0.0255(7) -0.0004(6) 0.0026(6) 0.0034(7)
C2 0.0463(10) 0.0435(9) 0.0260(7) 0.0012(6) 0.0027(6) 0.0056(7)
C3 0.104(2) 0.107(2) 0.0356(11) -0.0122(12) -0.0058(12) 0.0596(18)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2194(17) . ?
O2 N1 1.2179(17) . ?
N1 C1 1.4770(18) . ?
C1 C2 1.321(2) . ?
C1 C3 1.469(3) . ?
C2 C2 1.446(3) 3_655 ?
C2 H2 0.931(19) . ?
C3 H3A 0.93(4) . ?
C3 H3B 0.86(3) . ?
C3 H3C 0.93(3) . ?

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
_geom_angle_publ_flag
O2 N1 O1 122.41(13) . . ?
O2 N1 C1 117.83(13) . . ?
O1 N1 C1 119.76(13) . . ?
C2 C1 C3 129.61(15) . . ?
C2 C1 N1 116.62(13) . . ?
C3 C1 N1 113.76(15) . . ?
C1 C2 C2 123.61(19) . 3_655 ?
C1 C2 H2 119.5(11) . . ?
C2 C2 H2 116.9(11) 3_655 . ?
C1 C3 H3A 111.1(17) . . ?
C1 C3 H3B 107.5(19) . . ?
H3A C3 H3B 109(2) . . ?
C1 C3 H3C 114(2) . . ?
H3A C3 H3C 110(3) . . ?
H3B C3 H3C 105(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C2 -172.68(15) . . . . ?
O1 N1 C1 C2 7.7(2) . . . . ?
O2 N1 C1 C3 6.1(3) . . . . ?
O1 N1 C1 C3 -173.6(2) . . . . ?
C3 C1 C2 C2 1.2(4) . . . 3_655 ?
N1 C1 C2 C2 179.69(19) . . . 3_655 ?


#--------------------Hydrogen bonding scheme-----------------------------# 

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag


#
# Hydrogen bonding scheme
# ======== ======= ======
#
#  D   H   A   D-H       H...A     D...A      D-H...A    symm  publ
#  -   -   -   ---       -----     -----      -------    ----  ----

C2 H2 O1 0.931(19) 2.733(19) 3.583(2) 152.2(14) 2_645 yes



_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038


_iucr_refine_instruction_details 
;
#---------------------------------------------------------

TITL dk11 in P2(1)/n
CELL  0.71073   5.4312   6.1004  12.3902   90.000  101.006   90.000
ZERR     2.00   0.0008   0.0010   0.0013    0.000    0.005    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  12   16   4    8
 
MERG   2
SHEL 0.74 8
FMAP   2
PLAN   10
SIZE     0.20   0.22   0.32
ACTA
CONF
BOND
BOND $H
 
EQIV $1 1.5-X, -0.5+Y, 0.5-Z
EQIV $2 1.5-X, 0.5+Y, 0.5-Z
EQIV $3 0.5-X, -0.5+Y, 0.5-Z
 
RTAB XHY C2 H2 O1_$1
RTAB H..O H2 O1_$1
RTAB O..O C2 O1_$1
 
RTAB O..O N1 O1_$2
RTAB O..O N1 O2_$3
 
MPLA 4 C1 N1 O1 O2 O1_$2 O2_$3
 
L.S.   4
TEMP    23.00
WGHT    0.050100    0.038800
EXTI    0.768000
FVAR       2.42405
O1    4    0.686734    0.067064    0.276101    11.00000    0.06837    0.06560 =
         0.03313   -0.00287   -0.00586    0.01840
O2    4    0.384209    0.285946    0.284810    11.00000    0.07094    0.06221 =
         0.03563   -0.00977    0.01548    0.00870
N1    3    0.502517    0.170877    0.232577    11.00000    0.05337    0.04000 =
         0.02770   -0.00275    0.00573    0.00000
C1    1    0.417200    0.160139    0.112146    11.00000    0.04893    0.04691 =
         0.02546   -0.00041    0.00260    0.00343
C2    1    0.530848    0.015986    0.058838    11.00000    0.04629    0.04345 =
         0.02605    0.00119    0.00268    0.00561
C3    1    0.211077    0.311665    0.069895    11.00000    0.10420    0.10663 =
         0.03556   -0.01218   -0.00577    0.05964
H2    2    0.655843   -0.073262    0.098052    11.00000    0.04805
H3A   2    0.166907    0.303785   -0.006455    11.00000    0.11339
H3B   2    0.262571    0.442812    0.088544    11.00000    0.10201
H3C   2    0.068944    0.292622    0.101129    11.00000    0.12354
HKLF    4
 
REM  dk11 in P2(1)/n
REM R1 =  0.0422 for    666 Fo > 4sig(Fo)  and  0.0783 for all   1038 data
REM     72 parameters refined using      0 restraints
 
END
 
WGHT      0.0502      0.0385
REM Highest difference peak  0.154,  deepest hole -0.170,  1-sigma level  0.038
Q1    1   0.5301  0.0338  0.0016  11.00000  0.05    0.15
Q2    1   0.4327  0.1462  0.1662  11.00000  0.05    0.15
Q3    1   0.3765  0.2616  0.3659  11.00000  0.05    0.12
Q4    1   0.7919  0.1432  0.2343  11.00000  0.05    0.12
Q5    1   0.5172  0.1415  0.0779  11.00000  0.05    0.12
Q6    1   0.3913  0.3664  0.2247  11.00000  0.05    0.12
Q7    1   0.3314  0.5047  0.1043  11.00000  0.05    0.11
Q8    1   0.0825  0.2133  0.0051  11.00000  0.05    0.11
Q9    1   0.5660 -0.1377  0.2230  11.00000  0.05    0.10
Q10   1   0.6864  0.1292  0.3580  11.00000  0.05    0.10

;


#   -------------  END of CIF  -----------------#



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1529751'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Dinitro-1,3-butadiene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N2 O4'
_chemical_formula_sum            'C4 H4 N2 O4'
_chemical_formula_weight         144.09

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_symmetry_Int_Tables_number      14


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'

_cell_length_a                   3.8306(3)
_cell_length_b                   10.3433(6)
_cell_length_c                   7.9532(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.516(6)
_cell_angle_gamma                90.00
_cell_volume                     307.63(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3158
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      28.24

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             148
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 area-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3158
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         28.24
_reflns_number_total             762
_reflns_number_gt                528
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'

#------------------------------- Refinement data-----------------------#  


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         762
_refine_ls_number_parameters     54
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2636(4) 0.26272(11) 0.26130(18) 0.0740(5) Uani 1 1 d . . .
O2 O 0.6360(4) 0.14293(14) 0.43439(18) 0.0828(5) Uani 1 1 d . . .
N1 N 0.3981(4) 0.15860(13) 0.30685(17) 0.0511(4) Uani 1 1 d . . .
C1 C 0.2789(4) 0.04488(13) 0.20389(19) 0.0427(4) Uani 1 1 d . . .
C2 C 0.0581(4) 0.05551(12) 0.05421(17) 0.0372(3) Uani 1 1 d . . .
H1 H 0.384(5) -0.0282(16) 0.255(2) 0.055(5) Uiso 1 1 d . . .
H2 H -0.026(4) 0.1395(15) 0.015(2) 0.049(4) 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
O1 0.0981(11) 0.0419(6) 0.0783(10) -0.0173(6) 0.0107(8) -0.0059(6)
O2 0.0860(10) 0.0912(10) 0.0572(8) -0.0108(7) -0.0154(7) -0.0280(8)
N1 0.0559(8) 0.0535(8) 0.0434(7) -0.0106(6) 0.0092(6) -0.0167(6)
C1 0.0482(9) 0.0357(7) 0.0417(8) -0.0028(6) 0.0042(7) -0.0033(6)
C2 0.0410(7) 0.0322(7) 0.0388(7) -0.0001(5) 0.0094(6) -0.0024(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2147(17) . ?
O2 N1 1.2186(18) . ?
N1 C1 1.4493(18) . ?
C1 C2 1.307(2) . ?
C1 H1 0.909(16) . ?
C2 C2 1.447(3) 3 ?
C2 H2 0.955(16) . ?

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
_geom_angle_publ_flag
O1 N1 O2 123.95(14) . . ?
O1 N1 C1 119.32(13) . . ?
O2 N1 C1 116.71(14) . . ?
C2 C1 N1 120.58(13) . . ?
C2 C1 H1 127.7(10) . . ?
N1 C1 H1 111.6(10) . . ?
C1 C2 C2 122.06(16) . 3 ?
C1 C2 H2 118.6(10) . . ?
C2 C2 H2 119.4(10) 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 7.4(2) . . . . ?
O2 N1 C1 C2 -171.34(15) . . . . ?
N1 C1 C2 C2 178.12(16) . . . 3 ?



#--------------------Hydrogen bonding scheme-----------------------------# 

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag


#
# Hydrogen bonding scheme
# ======== ======= ======
#
#  D   H   A   D-H       H...A     D...A      D-H...A    symm  publ
#  -   -   -   ---       -----     -----      -------    ----  ----

C1 H1 O1 0.909(16) 2.567(17) 3.3846(19) 149.9(14) 2_645 yes
C1 H1 O2 0.909(16) 2.758(17) 3.428(2) 131.4(14) 3_656 yes
C2 H2 O2 0.955(16) 2.606(16) 3.5473(19) 168.8(13) 4_465 yes


_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032


_iucr_refine_instruction_details 
;
#---------------------------------------------------------

TITL DK10A in P2(1)/c
CELL  0.71073   3.8306  10.3433   7.9532   90.000  102.516   90.000
ZERR     2.00   0.0003   0.0006   0.0006    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  8    8    4    8
MERG   2

EQIV $1 1-X, -0.5+Y, 0.5-Z
EQIV $2 -1+X, 0.5-Y, -0.5+Z
EQIV $3 -1+X, Y, Z
EQIV $4 1-X, -Y, 1-Z

RTAB XHY C1 H1 O1_$1
RTAB XHY C2 H2 O2_$2
RTAB XHY C1 H1 O2_$4

RTAB H..O H1 O1_$1
RTAB H..O H1 O2_$4
RTAB H..O H2 O2_$2

RTAB O..O C1 O1_$1
RTAB O..O C1 O2_$4
RTAB O..O C2 O2_$2

RTAB O..O N1 O2_$3

MPLA 4 C1 N1 O1 O2 O2_$3
FMAP   2
PLAN   10
SIZE     0.22   0.24   0.24
ACTA
BOND   $H
CONF
L.S.   5
TEMP    23.00
WGHT    0.037200    0.067900
FVAR       1.86687
O1    4    0.263569    0.262719    0.261302    11.00000    0.09811    0.04194 =
         0.07826   -0.01733    0.01072   -0.00593
O2    4    0.635964    0.142934    0.434389    11.00000    0.08605    0.09121 =
         0.05716   -0.01080   -0.01540   -0.02804
N1    3    0.398070    0.158605    0.306846    11.00000    0.05588    0.05349 =
         0.04339   -0.01055    0.00924   -0.01670
C1    1    0.278878    0.044878    0.203892    11.00000    0.04819    0.03571 =
         0.04172   -0.00277    0.00420   -0.00332
C2    1    0.058061    0.055507    0.054212    11.00000    0.04097    0.03217 =
         0.03881   -0.00008    0.00935   -0.00236
H1    2    0.384012   -0.028232    0.254763    11.00000    0.05461
H2    2   -0.026342    0.139530    0.015335    11.00000    0.04924
HKLF    4
 
REM  DK10A in P2(1)/c
REM R1 =  0.0356 for    528 Fo > 4sig(Fo)  and  0.0585 for all    762 data
REM     54 parameters refined using      0 restraints
 
END
 
WGHT      0.0372      0.0682
REM Highest difference peak  0.161,  deepest hole -0.149,  1-sigma level  0.032
Q1    1   0.0000  0.0000  0.0000  10.50000  0.05    0.16
Q2    1   0.4385  0.1510  0.4719  11.00000  0.05    0.15
Q3    1   0.2885  0.0575  0.0960  11.00000  0.05    0.14
Q4    1   0.6298  0.1649  0.3559  11.00000  0.05    0.12
Q5    1   0.3724  0.1005  0.2450  11.00000  0.05    0.12
Q6    1   0.0565  0.0324  0.1566  11.00000  0.05    0.12
Q7    1   0.7363  0.1308  0.4560  11.00000  0.05    0.10
Q8    1   0.4507  0.2372  0.2146  11.00000  0.05    0.10
Q9    1   0.7203  0.0771  0.4433  11.00000  0.05    0.09
Q10   1   0.2322 -0.0281  0.2945  11.00000  0.05    0.09

;
