# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_qx396
_database_code_depnum_ccdc_archive 'CCDC 2150220'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2022-02-04 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-11
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        d4-diamino-dinitroethene
_chemical_name_common            FOX-7-d4
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 D4 N4 O4'
_chemical_formula_sum            'C2 D4 N4 O4'
_chemical_formula_weight         152.12

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'



_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.
;

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

_cell_length_a                   6.5238(13)
_cell_length_b                   6.9618(8)
_cell_length_c                   11.3592(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     515.91(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    1182
_cell_measurement_theta_min      3.5540
_cell_measurement_theta_max      28.5740

_exptl_crystal_description       block
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            8171
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_max         28.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1279
_reflns_number_gt                1090
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.0350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 426 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1279
_refine_ls_number_parameters     107
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000



_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
;



_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      0.0726169000
_diffrn_orient_matrix_UB_12      0.0739414000
_diffrn_orient_matrix_UB_13      -0.0103916000
_diffrn_orient_matrix_UB_21      -0.0806563000
_diffrn_orient_matrix_UB_22      0.0680440000
_diffrn_orient_matrix_UB_23      -0.0040287000
_diffrn_orient_matrix_UB_31      0.0069752000
_diffrn_orient_matrix_UB_32      0.0169637000
_diffrn_orient_matrix_UB_33      0.0614095000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  44.00   1.00   25.00    --  -19.09  57.00 -30.00   68
  2  ω    -29.00  46.00   1.00   25.00    --  -19.09  57.00-120.00   75
  3  ω    -73.00 -25.00   1.00   25.00    --  -19.09 127.00 136.43   48
  4  ω      4.00  46.00   1.00   25.00    --  -19.09  57.00 150.00   42
  5  ω      4.00  83.00   1.00   25.00    --   20.18  57.00-150.00   79
  6  ω      3.00  83.00   1.00   25.00    --   20.18  57.00  30.00   80
  7  ω      7.00  81.00   1.00   25.00    --   20.18  57.00 -60.00   74
  8  ω      3.00  84.00   1.00   25.00    --   20.18  57.00 120.00   81
  9  ω    -15.00  59.00   1.00   25.00    --   20.18 -99.00 120.00   74
 10  ω    -38.00  31.00   1.00   25.00    --   20.18 -57.00  30.00   69
 11  ω      8.00  59.00   1.00   25.00    --   20.18 -99.00 -30.00   51
 12  ω     -7.00  18.00   1.00   25.00    --   20.18  77.00-120.00   25
;



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'
D D 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_
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.4234(4) 0.7606(4) 0.3839(2) 0.0231(6) Uani 1 1 d . . . . .
O4 O 0.2847(4) 0.8191(4) 0.5530(2) 0.0254(7) Uani 1 1 d . . . . .
O2 O 0.3204(4) 0.4357(4) 0.3002(2) 0.0257(7) Uani 1 1 d . . . . .
O1 O 0.4169(5) 0.2146(3) 0.4217(2) 0.0256(7) Uani 1 1 d . . . . .
N4 N 0.3428(5) 0.7030(4) 0.4766(3) 0.0190(7) Uani 1 1 d . . . . .
N3 N 0.3580(5) 0.3817(4) 0.4018(3) 0.0217(7) Uani 1 1 d . . . . .
N2 N 0.2073(5) 0.5409(5) 0.6990(3) 0.0238(7) Uani 1 1 d . . . . .
N1 N 0.2675(6) 0.2400(5) 0.6334(3) 0.0217(8) Uani 1 1 d . . . . .
C2 C 0.3259(6) 0.5066(5) 0.4985(3) 0.0180(8) Uani 1 1 d . . . . .
C1 C 0.2675(6) 0.4287(5) 0.6132(3) 0.0201(8) Uani 1 1 d . . . . .
D2 D 0.220(6) 0.206(6) 0.701(4) 0.015(10) Uiso 1 1 d . . . . .
D1 D 0.311(6) 0.165(7) 0.575(4) 0.015(10) Uiso 1 1 d . . . . .
D4 D 0.203(6) 0.671(7) 0.683(4) 0.023(12) Uiso 1 1 d . . . . .
D3 D 0.182(6) 0.491(6) 0.767(4) 0.014(10) Uiso 1 1 d . . . . .


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
O3 N4 1.243(4) . ?
O4 N4 1.245(4) . ?
O2 N3 1.239(4) . ?
O1 N3 1.246(4) . ?
N4 C2 1.394(5) . ?
N3 C2 1.417(4) . ?
N2 C1 1.309(5) . ?
N2 D4 0.92(5) . ?
N2 D3 0.86(4) . ?
N1 C1 1.334(5) . ?
N1 D2 0.87(4) . ?
N1 D1 0.89(5) . ?
C2 C1 1.462(5) . ?

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
O3 N4 O4 120.6(3) . . ?
O3 N4 C2 120.1(3) . . ?
O4 N4 C2 119.2(3) . . ?
O2 N3 O1 120.9(3) . . ?
O2 N3 C2 120.5(3) . . ?
O1 N3 C2 118.6(3) . . ?
C1 N2 D4 117(3) . . ?
C1 N2 D3 119(3) . . ?
D4 N2 D3 124(4) . . ?
C1 N1 D2 115(3) . . ?
C1 N1 D1 116(3) . . ?
D2 N1 D1 128(4) . . ?
N4 C2 N3 116.9(3) . . ?
N4 C2 C1 122.9(3) . . ?
N3 C2 C1 120.1(3) . . ?
N2 C1 N1 117.3(4) . . ?
N2 C1 C2 121.4(3) . . ?
N1 C1 C2 121.3(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
O3 N4 C2 N3 -14.5(5) . . . . ?
O4 N4 C2 N3 168.7(3) . . . . ?
O3 N4 C2 C1 168.7(3) . . . . ?
O4 N4 C2 C1 -8.1(6) . . . . ?
O2 N3 C2 N4 -28.2(5) . . . . ?
O1 N3 C2 N4 154.6(3) . . . . ?
O2 N3 C2 C1 148.7(4) . . . . ?
O1 N3 C2 C1 -28.5(5) . . . . ?
N4 C2 C1 N2 7.1(6) . . . . ?
N3 C2 C1 N2 -169.7(4) . . . . ?
N4 C2 C1 N1 -175.0(4) . . . . ?
N3 C2 C1 N1 8.3(6) . . . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

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
N1 D2 O3 0.87(4) 2.31(4) 3.110(4) 154(4) 4_545




_refine_diff_density_max         0.268
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.056

_shelxl_version_number           ?






