# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_px233
_database_code_depnum_ccdc_archive 'CCDC 2094642'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;
_audit_creation_date             2020-06-19
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        2,2-dihydroxymethyl-5,5-bitetrazole
_chemical_name_common            2,2-dihydroxymethyl-5,5-bitetrazole
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N8 O2'
_chemical_formula_sum            'C4 H6 N8 O2'
_chemical_formula_weight         198.17

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

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.5207(5)
_cell_length_b                   7.9263(9)
_cell_length_c                   11.5245(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.503(10)
_cell_angle_gamma                90
_cell_volume                     408.41(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    107(2)
_cell_measurement_reflns_used    1388
_cell_measurement_theta_min      3.1090
_cell_measurement_theta_max      31.2460

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.141
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (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    1.611
_exptl_crystal_F_000             204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      107(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            3697
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         26.370
_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             834
_reflns_number_gt                727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (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)+(0.0399P)²+0.1263P] 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 ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         834
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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      -0.0633183000
_diffrn_orient_matrix_UB_12      -0.0784146000
_diffrn_orient_matrix_UB_13      0.0130051000
_diffrn_orient_matrix_UB_21      0.0483817000
_diffrn_orient_matrix_UB_22      -0.0363680000
_diffrn_orient_matrix_UB_23      -0.0502275000
_diffrn_orient_matrix_UB_31      0.1371288000
_diffrn_orient_matrix_UB_32      -0.0233332000
_diffrn_orient_matrix_UB_33      0.0343271000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -39.00   1.00   25.00    --  -28.86-178.00 120.00   69
  2  ω      6.00 100.00   1.00   25.00    --   29.64  57.00-150.00   94
  3  ω      6.00 100.00   1.00   25.00    --   29.64  57.00  60.00   94
  4  ω    -20.00  74.00   1.00   25.00    --   29.64 -99.00 -30.00   94
  5  ω     42.00 112.00   1.00   25.00    --   29.64-178.00-150.00   70
  6  ω    -35.00  97.00   1.00   25.00    --   29.64  19.00  30.00  132
;



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_
_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
O1 O 0.4446(2) 0.50400(12) 0.70959(9) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.2454(2) 0.27494(14) 0.59373(10) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.4539(2) 0.15558(14) 0.61325(10) 0.0240(3) Uani 1 1 d . . . . .
N4 N 0.1908(3) 0.13967(14) 0.43391(10) 0.0261(3) Uani 1 1 d . . . . .
N3 N 0.0855(3) 0.26915(15) 0.48818(10) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.4134(3) 0.07386(16) 0.51206(11) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.1948(3) 0.40196(18) 0.68352(13) 0.0265(3) Uani 1 1 d . . . . .
H2B H 0.023(3) 0.467(2) 0.6461(14) 0.027(4) Uiso 1 1 d . . . . .
H2A H 0.149(3) 0.334(2) 0.7485(15) 0.029(4) Uiso 1 1 d . . . . .
H1 H 0.554(5) 0.455(3) 0.778(2) 0.065(6) 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
O1 C2 1.3854(17) . ?
O1 H1 0.95(2) . ?
N2 N3 1.3206(16) . ?
N2 N1 1.3309(15) . ?
N2 C2 1.4856(17) . ?
N1 C1 1.3229(17) . ?
N4 N3 1.3263(17) . ?
N4 C1 1.3519(16) . ?
C1 C1 1.458(3) 3_656 ?
C2 H2B 0.980(16) . ?
C2 H2A 0.970(17) . ?

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
C2 O1 H1 104.6(13) . . ?
N3 N2 N1 114.11(11) . . ?
N3 N2 C2 123.05(11) . . ?
N1 N2 C2 122.83(11) . . ?
C1 N1 N2 101.35(10) . . ?
N3 N4 C1 105.55(11) . . ?
N2 N3 N4 105.99(10) . . ?
N1 C1 N4 113.00(12) . . ?
N1 C1 C1 123.58(14) . 3_656 ?
N4 C1 C1 123.41(15) . 3_656 ?
O1 C2 N2 110.01(11) . . ?
O1 C2 H2B 110.7(9) . . ?
N2 C2 H2B 104.3(9) . . ?
O1 C2 H2A 114.7(9) . . ?
N2 C2 H2A 103.4(9) . . ?
H2B C2 H2A 112.9(13) . . ?

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
N3 N2 N1 C1 -0.06(15) . . . . ?
C2 N2 N1 C1 179.17(12) . . . . ?
N1 N2 N3 N4 0.07(15) . . . . ?
C2 N2 N3 N4 -179.16(12) . . . . ?
C1 N4 N3 N2 -0.05(14) . . . . ?
N2 N1 C1 N4 0.03(15) . . . . ?
N2 N1 C1 C1 -178.84(16) . . . 3_656 ?
N3 N4 C1 N1 0.01(16) . . . . ?
N3 N4 C1 C1 178.88(15) . . . 3_656 ?
N3 N2 C2 O1 -116.46(14) . . . . ?
N1 N2 C2 O1 64.38(16) . . . . ?

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
C2 H2B N3 0.980(16) 2.602(16) 3.4022(19) 138.9(12) 3_566




_refine_diff_density_max         0.240
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039

_shelxl_version_number           ?







####################################################################### 
# 
# 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_px248
_database_code_depnum_ccdc_archive 'CCDC 2094643'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        2,2-dinitratomethyl-5,5-bitetrazole
_chemical_name_common            2,2-dinitratomethyl-5,5-bitetrazole
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N10 O6'
_chemical_formula_sum            'C4 H4 N10 O6'
_chemical_formula_weight         288.17

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 21 c'
_symmetry_Int_Tables_number      114
_symmetry_space_group_name_Hall  'P -4 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'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   9.44290(10)
_cell_length_b                   9.44290(10)
_cell_length_c                   12.3008(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1096.84(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    7011
_cell_measurement_theta_min      2.6900
_cell_measurement_theta_max      32.0890

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.323
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (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    1.745
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      108(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            22865
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.719
_diffrn_reflns_theta_max         32.757
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1950
_reflns_number_gt                1764
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.946
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (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)+(0.0458P)²+0.1267P] 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 706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1950
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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      -0.0545359000
_diffrn_orient_matrix_UB_12      -0.0168484000
_diffrn_orient_matrix_UB_13      0.0374903000
_diffrn_orient_matrix_UB_21      0.0094920000
_diffrn_orient_matrix_UB_22      0.0665175000
_diffrn_orient_matrix_UB_23      0.0257524000
_diffrn_orient_matrix_UB_31      -0.0507721000
_diffrn_orient_matrix_UB_32      0.0305208000
_diffrn_orient_matrix_UB_33      -0.0354635000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  44.00   1.00   15.00    --  -23.53  57.00 -30.00   84
  2  ω     18.00  71.00   1.00   15.00    --   24.78  57.00 -30.00   53
  3  ω      2.00  90.00   1.00   15.00    --   24.78  70.00 100.00   88
  4  ω     15.00  87.00   1.00   15.00    --   24.78  57.00  30.00   72
  5  ω     22.00  91.00   1.00   15.00    --   24.78  57.00 -90.00   69
  6  ω    -20.00  64.00   1.00   15.00    --   24.78 -99.00  60.00   84
  7  ω      8.00  91.00   1.00   15.00    --   24.78  57.00-150.00   83
  8  ω    -32.00  -7.00   1.00   15.00    --   24.78 131.00-141.59   25
  9  ω    -43.00  16.00   1.00   15.00    --   24.78 -37.00  90.00   59
 10  ω    -20.00  64.00   1.00   15.00    --   24.78 -99.00-180.00   84
 11  ω    -39.00  52.00   1.00   15.00    --   24.78 -77.00-120.00   91
;



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_
_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
O1 O 0.81086(11) 0.14021(12) 0.53433(9) 0.0231(2) Uani 1 1 d . . . . .
O2 O 0.63582(13) 0.05465(14) 0.42884(11) 0.0328(3) Uani 1 1 d . . . . .
O3 O 0.84119(14) 0.10962(13) 0.36026(10) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.60910(13) 0.23027(12) 0.62491(10) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.64050(13) 0.36720(13) 0.62291(10) 0.0206(2) Uani 1 1 d . . . . .
N5 N 0.75465(14) 0.09653(14) 0.43147(10) 0.0232(3) Uani 1 1 d . . . . .
N3 N 0.47204(13) 0.20223(14) 0.63498(11) 0.0234(2) Uani 1 1 d . . . . .
N4 N 0.40823(13) 0.32577(13) 0.63987(11) 0.0230(2) Uani 1 1 d . . . . .
C1 C 0.51248(14) 0.42401(14) 0.63185(11) 0.0189(2) Uani 1 1 d . . . . .
C2 C 0.71613(15) 0.11876(16) 0.62220(13) 0.0227(3) Uani 1 1 d . . . . .
H2A H 0.672(2) 0.031(2) 0.6220(17) 0.023(5) Uiso 1 1 d . . . . .
H2B H 0.769(2) 0.120(2) 0.6844(18) 0.027(5) 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
O1 C2 1.4176(18) . ?
O1 N5 1.4327(16) . ?
O2 N5 1.1902(17) . ?
O3 N5 1.2043(17) . ?
N2 N1 1.3268(16) . ?
N2 N3 1.3269(17) . ?
N2 C2 1.4599(17) . ?
N1 C1 1.3271(18) . ?
N3 N4 1.3143(18) . ?
N4 C1 1.3563(18) . ?
C1 C1 1.454(3) 2_665 ?
C2 H2A 0.928(19) . ?
C2 H2B 0.91(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
C2 O1 N5 113.48(11) . . ?
N1 N2 N3 114.47(12) . . ?
N1 N2 C2 123.21(12) . . ?
N3 N2 C2 122.24(12) . . ?
N2 N1 C1 100.88(11) . . ?
O2 N5 O3 130.85(14) . . ?
O2 N5 O1 117.97(12) . . ?
O3 N5 O1 111.19(12) . . ?
N4 N3 N2 105.92(11) . . ?
N3 N4 C1 105.72(12) . . ?
N1 C1 N4 113.00(12) . . ?
N1 C1 C1 123.13(15) . 2_665 ?
N4 C1 C1 123.87(16) . 2_665 ?
O1 C2 N2 110.56(12) . . ?
O1 C2 H2A 114.3(13) . . ?
N2 C2 H2A 109.3(13) . . ?
O1 C2 H2B 107.0(13) . . ?
N2 C2 H2B 110.3(14) . . ?
H2A C2 H2B 105.2(19) . . ?

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
N3 N2 N1 C1 -0.35(16) . . . . ?
C2 N2 N1 C1 -177.22(12) . . . . ?
C2 O1 N5 O2 3.57(18) . . . . ?
C2 O1 N5 O3 -176.33(12) . . . . ?
N1 N2 N3 N4 0.06(17) . . . . ?
C2 N2 N3 N4 176.96(12) . . . . ?
N2 N3 N4 C1 0.26(15) . . . . ?
N2 N1 C1 N4 0.52(15) . . . . ?
N2 N1 C1 C1 -178.89(7) . . . 2_665 ?
N3 N4 C1 N1 -0.52(15) . . . . ?
N3 N4 C1 C1 178.89(8) . . . 2_665 ?
N5 O1 C2 N2 -78.68(14) . . . . ?
N1 N2 C2 O1 -51.58(17) . . . . ?
N3 N2 C2 O1 131.79(14) . . . . ?

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
? ? ? ? ? ? ? ?





_refine_diff_density_max         0.293
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.047

_shelxl_version_number           ?






####################################################################### 
# 
# 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_px270
_database_code_depnum_ccdc_archive 'CCDC 2094644'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;
_audit_creation_date             2020-07-24
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        2,2-diazidomethyl-5,5-bitetrazole
_chemical_name_common            2,2-diazidomethyl-5,5-bitetrazole
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N14'
_chemical_formula_sum            'C4 H4 N14'
_chemical_formula_weight         248.21

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_Int_Tables_number      88
_symmetry_space_group_name_Hall  '-I 4ad'



_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+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   17.1656(10)
_cell_length_b                   17.1656(10)
_cell_length_c                   6.7040(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1975.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    830
_cell_measurement_theta_min      3.3310
_cell_measurement_theta_max      23.2350

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (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    1.669
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      113(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            6544
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         26.360
_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             1009
_reflns_number_gt                698
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (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)+(0.0397P)²+0.4034P] 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 ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1009
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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      -0.0127459000
_diffrn_orient_matrix_UB_12      -0.0150484000
_diffrn_orient_matrix_UB_13      0.0929326000
_diffrn_orient_matrix_UB_21      0.0322596000
_diffrn_orient_matrix_UB_22      0.0178268000
_diffrn_orient_matrix_UB_23      0.0479086000
_diffrn_orient_matrix_UB_31      -0.0224731000
_diffrn_orient_matrix_UB_32      0.0341057000
_diffrn_orient_matrix_UB_33      0.0160389000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  33.00   1.00   45.00    --  -20.37  77.00 -30.00   26
  2  ω      3.00  50.00   1.00   45.00    --  -20.37  57.00-150.00   47
  3  ω    -47.00  45.00   1.00   45.00    --   21.23 -57.00 -60.00   92
  4  ω     -3.00  28.00   1.00   45.00    --   21.23  77.00  60.00   31
  5  ω     -5.00  25.00   1.00   45.00    --   21.23  77.00 -60.00   30
  6  ω     11.00  92.00   1.00   45.00    --   21.23  57.00  90.00   81
  7  ω    -20.00  65.00   1.00   45.00    --   21.23 -99.00-180.00   85
;



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'


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
N2 N 0.40178(10) 0.45249(9) 0.3012(2) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.47356(10) 0.47574(10) 0.2572(2) 0.0224(4) Uani 1 1 d . . . . .
N4 N 0.39544(10) 0.47094(10) -0.0098(2) 0.0261(4) Uani 1 1 d . . . . .
N3 N 0.35387(10) 0.44858(10) 0.1460(2) 0.0272(4) Uani 1 1 d . . . . .
N6 N 0.47208(12) 0.34871(10) 0.6227(3) 0.0316(5) Uani 1 1 d . . . . .
N5 N 0.40522(11) 0.35222(11) 0.5515(2) 0.0342(5) Uani 1 1 d . . . . .
C1 C 0.46770(11) 0.48666(11) 0.0612(3) 0.0206(5) Uani 1 1 d . . . . .
N7 N 0.53114(13) 0.33558(11) 0.6909(3) 0.0453(6) Uani 1 1 d . . . . .
C2 C 0.37863(14) 0.43051(14) 0.5035(3) 0.0282(5) Uani 1 1 d . . . . .
H2B H 0.4001(11) 0.4682(11) 0.590(3) 0.018(5) Uiso 1 1 d . . . . .
H2A H 0.3211(13) 0.4307(11) 0.506(3) 0.024(6) 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
N2 N1 1.328(2) . ?
N2 N3 1.328(2) . ?
N2 C2 1.463(2) . ?
N1 C1 1.331(2) . ?
N4 N3 1.322(2) . ?
N4 C1 1.356(2) . ?
N6 N7 1.135(2) . ?
N6 N5 1.245(3) . ?
N5 C2 1.455(3) . ?
C1 C1 1.454(4) 9_665 ?
C2 H2B 0.945(19) . ?
C2 H2A 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
N1 N2 N3 114.53(15) . . ?
N1 N2 C2 122.40(17) . . ?
N3 N2 C2 123.04(17) . . ?
N2 N1 C1 101.06(15) . . ?
N3 N4 C1 105.93(15) . . ?
N4 N3 N2 105.67(15) . . ?
N7 N6 N5 171.2(2) . . ?
N6 N5 C2 114.76(18) . . ?
N1 C1 N4 112.81(17) . . ?
N1 C1 C1 123.0(2) . 9_665 ?
N4 C1 C1 124.2(2) . 9_665 ?
N5 C2 N2 110.97(17) . . ?
N5 C2 H2B 111.9(11) . . ?
N2 C2 H2B 106.8(11) . . ?
N5 C2 H2A 108.2(12) . . ?
N2 C2 H2A 106.8(11) . . ?
H2B C2 H2A 112.1(16) . . ?

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
N3 N2 N1 C1 0.2(2) . . . . ?
C2 N2 N1 C1 178.19(18) . . . . ?
C1 N4 N3 N2 0.6(2) . . . . ?
N1 N2 N3 N4 -0.5(2) . . . . ?
C2 N2 N3 N4 -178.49(18) . . . . ?
N2 N1 C1 N4 0.2(2) . . . . ?
N2 N1 C1 C1 179.7(2) . . . 9_665 ?
N3 N4 C1 N1 -0.5(2) . . . . ?
N3 N4 C1 C1 -180.0(2) . . . 9_665 ?
N6 N5 C2 N2 87.8(2) . . . . ?
N1 N2 C2 N5 -78.6(2) . . . . ?
N3 N2 C2 N5 99.2(2) . . . . ?

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
? ? ? ? ? ? ? ?





_refine_diff_density_max         0.177
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046

_shelxl_version_number           ?






####################################################################### 
# 
# 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_yv377
_database_code_depnum_ccdc_archive 'CCDC 2094645'
loop_
_audit_author_name
_audit_author_address
'Joerg Stierstorfer'
;University of Munich (LMU)
Germany
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        2,2-chloromethyl-5,5-bitetrazole
_chemical_name_common            2,2-chloromethyl-5,5-bitetrazole
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 Cl2 N8'
_chemical_formula_sum            'C4 H4 Cl2 N8'
_chemical_formula_weight         235.05

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



_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3693(4)
_cell_length_b                   8.2279(4)
_cell_length_c                   6.7862(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.194(2)
_cell_angle_gamma                90
_cell_volume                     443.95(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    7117
_cell_measurement_theta_min      3.5634
_cell_measurement_theta_max      30.5317

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_exptl_special_details           ?


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode generator'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            11605
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.563
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1355
_reflns_number_gt                1190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Microsoft Word 2016'

_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)+(0.0205P)²+0.3218P] 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 ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1355
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0622
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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  ?
_diffrn_measurement_device       ?

_diffrn_detector                 ?
_diffrn_detector_type            ?



_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?
_diffrn_measurement_details      ?



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'
Cl Cl 0.1484 0.1585 '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'


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
Cl1 Cl 0.14858(4) 0.33191(4) 0.93683(5) 0.02309(10) Uani 1 1 d . . . . .
N2 N 0.26922(13) 0.53424(14) 0.71052(16) 0.0161(2) Uani 1 1 d . . . . .
N4 N 0.28055(14) 0.57776(15) 0.40842(17) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.18054(14) 0.58798(14) 0.52389(17) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.42443(14) 0.48718(14) 0.72558(17) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.42701(15) 0.51578(16) 0.53388(19) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.20209(17) 0.53198(16) 0.8830(2) 0.0180(2) Uani 1 1 d . . . . .
H2A H 0.287(2) 0.572(2) 1.000(3) 0.026(4) Uiso 1 1 d . . . . .
H2B H 0.105(2) 0.594(2) 0.846(3) 0.026(5) 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
Cl1 C2 1.7737(14) . ?
N2 N3 1.3279(15) . ?
N2 N1 1.3285(15) . ?
N2 C2 1.4482(15) . ?
N4 N3 1.3157(15) . ?
N4 C1 1.3549(17) . ?
N1 C1 1.3288(15) . ?
C1 C1 1.457(2) 3_666 ?
C2 H2A 0.95(2) . ?
C2 H2B 0.92(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
N3 N2 N1 114.35(10) . . ?
N3 N2 C2 122.20(11) . . ?
N1 N2 C2 123.43(11) . . ?
N3 N4 C1 105.59(10) . . ?
N4 N3 N2 106.07(10) . . ?
N2 N1 C1 100.80(10) . . ?
N1 C1 N4 113.19(11) . . ?
N1 C1 C1 123.30(14) . 3_666 ?
N4 C1 C1 123.51(14) . 3_666 ?
N2 C2 Cl1 111.40(9) . . ?
N2 C2 H2A 107.1(11) . . ?
Cl1 C2 H2A 108.7(11) . . ?
N2 C2 H2B 107.7(12) . . ?
Cl1 C2 H2B 108.1(12) . . ?
H2A C2 H2B 113.8(16) . . ?

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
C1 N4 N3 N2 0.49(14) . . . . ?
N1 N2 N3 N4 -0.42(15) . . . . ?
C2 N2 N3 N4 178.01(11) . . . . ?
N3 N2 N1 C1 0.14(14) . . . . ?
C2 N2 N1 C1 -178.26(12) . . . . ?
N2 N1 C1 N4 0.20(14) . . . . ?
N2 N1 C1 C1 179.94(16) . . . 3_666 ?
N3 N4 C1 N1 -0.45(15) . . . . ?
N3 N4 C1 C1 179.80(16) . . . 3_666 ?
N3 N2 C2 Cl1 105.39(12) . . . . ?
N1 N2 C2 Cl1 -76.33(14) . . . . ?

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
? ? ? ? ? ? ? ?





_refine_diff_density_max         0.413
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.062

_shelxl_version_number           ?







