# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ysj-s-hclo4-1-1-173k_auto
_database_code_depnum_ccdc_archive 'CCDC 2321375'
loop_
_audit_author_name
_audit_author_address
'Shu Jing Yang'
;Nan Chang university
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl0.5 O2), C5 H13 N2'
_chemical_formula_sum            'C5 H13 Cl N2 O4'
_chemical_formula_weight         200.62
_chemical_absolute_configuration S
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.1484(2)
_cell_length_b                   8.1484(2)
_cell_length_c                   26.8449(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1782.41(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5633
_cell_measurement_temperature    172.8(2)
_cell_measurement_theta_max      30.7590
_cell_measurement_theta_min      2.6010
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.723
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.8(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  14.00   0.50    1.00    --   -5.14  28.00  -5.00   52
  2  ω     32.00  59.00   0.50    1.00    --   -5.14  28.00  -5.00   54
  3  ω    -18.00  26.00   0.50    1.00    --   -5.14 -99.00 -30.00   88
  4  ω     -7.00  27.00   0.50    1.00    --   -5.14 -99.00-150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0018542000
_diffrn_orient_matrix_UB_12      0.0270919000
_diffrn_orient_matrix_UB_13      -0.0251022000
_diffrn_orient_matrix_UB_21      0.0316658000
_diffrn_orient_matrix_UB_22      0.0772374000
_diffrn_orient_matrix_UB_23      0.0074673000
_diffrn_orient_matrix_UB_31      0.0810829000
_diffrn_orient_matrix_UB_32      -0.0295988000
_diffrn_orient_matrix_UB_33      -0.0034812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.761
_reflns_number_gt                2055
_reflns_number_total             2248
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+1.0487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 Cl2-O4 \\sim Cl2-O3
 with sigma of 0.02
2. Others
 Fixed Sof: O3(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2A)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.17892(8) 0.82108(8) 0.250000 0.0267(2) Uani 1 2 d S T P . .
N1 N 0.5582(3) 0.8133(3) 0.33588(8) 0.0235(5) Uani 1 1 d . . . . .
N2 N 0.7086(3) 1.1267(3) 0.35707(9) 0.0259(5) Uani 1 1 d . . . . .
C2 C 0.4672(3) 0.9358(3) 0.36750(9) 0.0246(5) Uani 1 1 d . . . . .
H2A H 0.394097 1.003279 0.345715 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6661(4) 0.8942(3) 0.29802(9) 0.0273(5) Uani 1 1 d . . . . .
H5A H 0.598490 0.960222 0.274830 0.033 Uiso 1 1 calc R U . . .
H5B H 0.725119 0.809874 0.278441 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7882(3) 1.0039(3) 0.32442(9) 0.0267(6) Uani 1 1 d . . . . .
H4A H 0.862637 0.935057 0.344718 0.032 Uiso 1 1 calc R U . . .
H4B H 0.855548 1.061744 0.299244 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5940(3) 1.0471(3) 0.39198(9) 0.0245(5) Uani 1 1 d . . . . .
H3A H 0.535597 1.133346 0.410945 0.029 Uiso 1 1 calc R U . . .
H3B H 0.658253 0.981367 0.416101 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3631(4) 0.8447(4) 0.40556(12) 0.0370(7) Uani 1 1 d . . . . .
H1C H 0.286701 0.771395 0.388254 0.056 Uiso 1 1 calc R U . . .
H1D H 0.301108 0.923999 0.425524 0.056 Uiso 1 1 calc R U . . .
H1E H 0.434535 0.780018 0.427413 0.056 Uiso 1 1 calc R U . . .
O2 O 0.2103(5) 0.9905(3) 0.25812(10) 0.0709(10) Uani 1 1 d . . . . .
O1 O 0.2314(3) 0.7299(3) 0.29248(10) 0.0560(8) Uani 1 1 d . . . . .
Cl2 Cl 0.58946(8) 1.41054(8) 0.250000 0.0357(3) Uani 1 2 d DS T P . .
O4 O 0.7072(3) 1.2928(3) 0.250000 0.101(2) Uani 1 2 d DS T P A 1
O5 O 0.5500(4) 1.4864(5) 0.29418(12) 0.0865(13) Uani 1 1 d . . . . .
H1A H 0.495(5) 0.748(5) 0.3213(13) 0.038(9) Uiso 1 1 d . . . . .
H1B H 0.624(4) 0.748(4) 0.3549(13) 0.035(9) Uiso 1 1 d . . . . .
H2 H 0.662(4) 1.189(4) 0.3396(12) 0.022(8) Uiso 1 1 d . . . . .
O3 O 0.4610(7) 1.2686(7) 0.2629(2) 0.0585(15) Uani 0.5 1 d D . P A 2


_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
Cl1 O2 1.421(3) 8_665 ?
Cl1 O2 1.421(3) . ?
Cl1 O1 1.427(2) 8_665 ?
Cl1 O1 1.427(2) . ?
N1 C2 1.505(3) . ?
N1 C5 1.497(4) . ?
N1 H1A 0.84(4) . ?
N1 H1B 0.92(4) . ?
N2 C4 1.480(3) . ?
N2 C3 1.473(4) . ?
N2 H2 0.78(3) . ?
C2 H2A 1.0000 . ?
C2 C3 1.523(4) . ?
C2 C1 1.521(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
Cl2 O4 1.356(4) . ?
Cl2 O5 1.375(3) . ?
Cl2 O5 1.376(3) 8_775 ?
Cl2 O3 1.599(5) . ?
Cl2 O3 1.599(5) 8_775 ?

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 Cl1 O2 111.9(3) 8_665 . ?
O2 Cl1 O1 108.67(18) 8_665 . ?
O2 Cl1 O1 109.23(17) . . ?
O2 Cl1 O1 109.23(17) 8_665 8_665 ?
O2 Cl1 O1 108.67(18) . 8_665 ?
O1 Cl1 O1 109.1(3) . 8_665 ?
C2 N1 H1A 112(3) . . ?
C2 N1 H1B 111(2) . . ?
C5 N1 C2 112.3(2) . . ?
C5 N1 H1A 109(2) . . ?
C5 N1 H1B 107(2) . . ?
H1A N1 H1B 104(3) . . ?
C4 N2 H2 107(2) . . ?
C3 N2 C4 110.9(2) . . ?
C3 N2 H2 111(2) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 C3 107.7(2) . . ?
N1 C2 C1 109.3(2) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 C3 112.3(2) . . ?
N1 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
N1 C5 C4 109.2(2) . . ?
H5A C5 H5B 108.3 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
N2 C4 C5 112.9(2) . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N2 C3 C2 114.7(2) . . ?
N2 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O4 Cl2 O5 118.88(15) . 8_775 ?
O4 Cl2 O5 118.88(15) . . ?
O4 Cl2 O3 87.2(2) . 8_775 ?
O5 Cl2 O5 122.2(3) . 8_775 ?
O5 Cl2 O3 93.6(3) 8_775 . ?
O5 Cl2 O3 93.6(3) . 8_775 ?
O5 Cl2 O3 89.1(3) . . ?
O5 Cl2 O3 89.1(3) 8_775 8_775 ?
O3 Cl2 O3 174.4(5) . 8_775 ?

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
N1 H1A O1 0.84(4) 2.29(4) 2.985(4) 141(3) . yes
N1 H1A O5 0.84(4) 2.30(4) 2.890(4) 128(3) 1_545 yes
N1 H1B N2 0.92(4) 1.97(4) 2.875(3) 172(3) 5_645 yes

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
N1 C2 C3 N2 54.3(3) . . . . ?
N1 C5 C4 N2 -55.8(3) . . . . ?
C2 N1 C5 C4 58.5(3) . . . . ?
C5 N1 C2 C3 -56.8(3) . . . . ?
C5 N1 C2 C1 -179.0(2) . . . . ?
C4 N2 C3 C2 -53.1(3) . . . . ?
C3 N2 C4 C5 53.0(3) . . . . ?
C1 C2 C3 N2 174.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.667
_oxdiff_exptl_absorpt_empirical_full_min 0.739
####################################################################### 
# 
# 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_ysj-220930-2-173k_auto
_database_code_depnum_ccdc_archive 'CCDC 2321376'
loop_
_audit_author_name
_audit_author_address
'Shu Jing Yang'
;Nan Chang university
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl O4, C9 H15 N4'
_chemical_formula_sum            'C9 H15 Cl N4 O4'
_chemical_formula_weight         278.70
_chemical_absolute_configuration S
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.9407(7)
_cell_length_b                   7.4715(4)
_cell_length_c                   18.8287(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.620(5)
_cell_angle_gamma                90
_cell_volume                     1879.23(17)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    13026
_cell_measurement_temperature    172.98(10)
_cell_measurement_theta_max      30.9270
_cell_measurement_theta_min      2.1020
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0852
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28322
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.212
_diffrn_reflns_theta_min         2.141
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  77.00   0.50    1.50    --    5.29  23.00-102.00   52
  2  ω     -6.00  41.00   0.50    1.50    --    5.29  23.00-102.00   94
  3  ω     -9.00  66.00   0.50    1.50    --    5.29  57.00 -90.00  150
  4  ω    -68.00  19.00   0.50    1.50    --    5.29 -23.00  92.00  174
  5  ω      1.00  27.00   0.50    1.50    --   -5.29 -99.00  30.00   52
  6  ω    -18.00  26.00   0.50    1.50    --   -5.29 -99.00  60.00   88
  7  ω     -5.00  27.00   0.50    1.50    --   -5.29 -99.00 -90.00   64
  8  ω    -19.00  67.00   0.50    1.50    --   -5.29  57.00 -30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124065000
_diffrn_orient_matrix_UB_12      -0.0877115000
_diffrn_orient_matrix_UB_13      -0.0087820000
_diffrn_orient_matrix_UB_21      -0.0513411000
_diffrn_orient_matrix_UB_22      -0.0240038000
_diffrn_orient_matrix_UB_23      -0.0099088000
_diffrn_orient_matrix_UB_31      -0.0053137000
_diffrn_orient_matrix_UB_32      0.0272711000
_diffrn_orient_matrix_UB_33      -0.0370217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.578
_reflns_number_gt                6695
_reflns_number_total             8681
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         8681
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1542
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 N7(H7), N10(H10), N2(H2), C13(H13), C6(H6), C24(H24)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C3(H3A,H3B), C5(H5A,H5B), C21(H21A,H21B),
 C17(H17A,H17B), C4(H4A,H4B), C23(H23A,H23B), C15(H15A,H15B), C11(H11A,H11B),
 C22(H22A,H22B), C20(H20A,H20B), C2(H2A,H2B), C26(H26A,H26B), C8(H8A,H8B)
1.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl2 Cl 0.37936(6) 0.53903(14) 0.29759(5) 0.0301(2) Uani 1 1 d . . . . .
Cl1 Cl 0.95264(7) 0.02024(14) 0.37097(5) 0.0311(2) Uani 1 1 d . . . . .
Cl3 Cl 0.29681(8) 0.91292(15) 0.04438(5) 0.0340(2) Uani 1 1 d . . . . .
O7 O 0.3429(3) 0.7048(5) 0.31771(19) 0.0497(9) Uani 1 1 d . . . . .
O3 O 0.9565(3) 0.1633(5) 0.32236(19) 0.0523(9) Uani 1 1 d . . . . .
O10 O 0.3523(3) 0.9562(6) 0.11941(16) 0.0532(10) Uani 1 1 d . . . . .
O6 O 0.3627(2) 0.3978(5) 0.34426(16) 0.0409(8) Uani 1 1 d . . . . .
O12 O 0.3183(2) 1.0430(6) -0.00490(17) 0.0466(8) Uani 1 1 d . . . . .
N7 N 0.5213(2) 0.4195(5) 0.15640(15) 0.0245(6) Uani 1 1 d . . . . .
H7 H 0.511412 0.394570 0.206020 0.029 Uiso 1 1 calc R U . . .
O4 O 0.8505(2) -0.0051(6) 0.37281(16) 0.0563(12) Uani 1 1 d . . . . .
N10 N 0.1509(2) 1.0004(5) 0.17727(16) 0.0254(7) Uani 1 1 d . . . . .
H10 H 0.161626 1.016443 0.127351 0.031 Uiso 1 1 calc R U . . .
O5 O 0.4844(2) 0.5537(6) 0.3041(2) 0.0558(10) Uani 1 1 d . . . . .
N2 N 0.8180(2) 0.0090(5) 0.51224(15) 0.0254(7) Uani 1 1 d . . . . .
H2 H 0.834259 0.022983 0.464142 0.030 Uiso 1 1 calc R U . . .
N6 N 0.7291(2) 0.5135(5) 0.20985(17) 0.0290(7) Uani 1 1 d . . . . .
O8 O 0.3271(3) 0.4976(5) 0.22149(16) 0.0508(9) Uani 1 1 d . . . . .
O9 O 0.1907(2) 0.9191(6) 0.03819(18) 0.0496(8) Uani 1 1 d . . . . .
N1 N 0.8954(3) -0.0231(5) 0.70492(19) 0.0409(9) Uani 1 1 d . . . . .
N3 N 0.6054(2) 0.0224(6) 0.45250(16) 0.0306(7) Uani 1 1 d . . . . .
N11 N -0.0482(2) 0.8594(6) 0.12734(17) 0.0356(9) Uani 1 1 d . . . . .
N4 N 0.5077(3) 0.1338(6) 0.26511(18) 0.0390(9) Uani 1 1 d . . . . .
O1 O 1.0111(3) 0.0631(7) 0.44433(17) 0.0613(12) Uani 1 1 d . . . . .
N9 N 0.2274(3) 1.0372(6) 0.36761(17) 0.0378(8) Uani 1 1 d . . . . .
O11 O 0.3236(3) 0.7397(5) 0.0253(2) 0.0566(9) Uani 1 1 d . . . . .
N8 N 0.4353(3) 0.4323(6) -0.03475(18) 0.0419(9) Uani 1 1 d . . . . .
C12 C 0.6950(3) 0.3299(6) 0.2118(2) 0.0303(8) Uani 1 1 d . . . . .
H12A H 0.679894 0.307714 0.259333 0.036 Uiso 1 1 calc R U . . .
H12B H 0.748619 0.246136 0.208481 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6023(3) 0.2972(6) 0.14799(19) 0.0296(8) Uani 1 1 d . . . . .
H16A H 0.616754 0.320905 0.100343 0.035 Uiso 1 1 calc R U . . .
H16B H 0.580739 0.170984 0.148209 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7545(3) -0.1554(6) 0.5059(2) 0.0346(9) Uani 1 1 d . . . . .
H3A H 0.734494 -0.172286 0.551841 0.042 Uiso 1 1 calc R U . . .
H3B H 0.792683 -0.262123 0.498619 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2337(3) 1.0498(6) 0.3093(2) 0.0305(8) Uani 1 1 d . . . . .
C5 C 0.6620(3) -0.1326(6) 0.4401(2) 0.0346(9) Uani 1 1 d . . . . .
H5A H 0.682228 -0.115454 0.394241 0.042 Uiso 1 1 calc R U . . .
H5B H 0.619872 -0.241351 0.434032 0.042 Uiso 1 1 calc R U . . .
N5 N 0.8143(3) 0.5017(8) 0.4001(2) 0.0541(12) Uani 1 1 d . . . . .
C21 C 0.1304(3) 0.8068(6) 0.1853(2) 0.0350(9) Uani 1 1 d . . . . .
H21A H 0.119708 0.785087 0.234364 0.042 Uiso 1 1 calc R U . . .
H21B H 0.188585 0.734582 0.182101 0.042 Uiso 1 1 calc R U . . .
O2 O 0.9871(3) -0.1387(6) 0.3448(3) 0.0703(12) Uani 1 1 d . . . . .
C17 C 0.4239(3) 0.3830(6) 0.09963(19) 0.0317(9) Uani 1 1 d . . . . .
H17A H 0.403613 0.257634 0.104496 0.038 Uiso 1 1 calc R U . . .
H17B H 0.371660 0.462510 0.108446 0.038 Uiso 1 1 calc R U . . .
C1 C 0.9014(3) -0.0167(6) 0.6464(2) 0.0324(9) Uani 1 1 d . . . . .
C13 C 0.6521(3) 0.6390(6) 0.21946(19) 0.0269(8) Uani 1 1 d . . . . .
H13 H 0.639203 0.614723 0.268145 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4315(3) 0.4124(7) 0.0240(2) 0.0323(8) Uani 1 1 d . . . . .
C9 C 0.5077(3) 0.0876(7) 0.3226(2) 0.0343(10) Uani 1 1 d . . . . .
N12 N -0.1441(3) 0.8444(8) -0.0634(2) 0.0575(12) Uani 1 1 d . . . . .
C4 C 0.7593(3) 0.1701(5) 0.5215(2) 0.0280(8) Uani 1 1 d . . . . .
H4A H 0.800912 0.278622 0.523975 0.034 Uiso 1 1 calc R U . . .
H4B H 0.741574 0.160637 0.568650 0.034 Uiso 1 1 calc R U . . .
C23 C 0.0388(3) 0.7517(7) 0.1250(2) 0.0372(9) Uani 1 1 d . . . . .
H23A H 0.051371 0.766842 0.076152 0.045 Uiso 1 1 calc R U . . .
H23B H 0.024613 0.623637 0.130916 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6818(3) 0.8340(6) 0.2168(2) 0.0374(9) Uani 1 1 d . . . . .
H14A H 0.740097 0.859944 0.259054 0.056 Uiso 1 1 calc R U . . .
H14B H 0.625843 0.910938 0.219238 0.056 Uiso 1 1 calc R U . . .
H14C H 0.698533 0.857045 0.170546 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5553(3) 0.6099(6) 0.1572(2) 0.0269(8) Uani 1 1 d . . . . .
H15A H 0.502626 0.690608 0.164547 0.032 Uiso 1 1 calc R U . . .
H15B H 0.566593 0.639376 0.109001 0.032 Uiso 1 1 calc R U . . .
C27 C -0.1431(3) 0.8195(9) -0.0037(2) 0.0466(12) Uani 1 1 d . . . . .
C6 C 0.6642(3) 0.1876(6) 0.4574(2) 0.0281(8) Uani 1 1 d . . . . .
H6 H 0.682252 0.205120 0.410138 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8261(3) 0.5396(8) 0.2641(2) 0.0368(9) Uani 1 1 d . . . . .
H11A H 0.851079 0.660788 0.257700 0.044 Uiso 1 1 calc R U . . .
H11B H 0.874140 0.451648 0.254683 0.044 Uiso 1 1 calc R U . . .
C22 C 0.0613(3) 1.1094(6) 0.1783(2) 0.0309(8) Uani 1 1 d . . . . .
H22A H 0.074612 1.237343 0.171106 0.037 Uiso 1 1 calc R U . . .
H22B H 0.048291 1.096630 0.227009 0.037 Uiso 1 1 calc R U . . .
C10 C 0.8223(3) 0.5193(7) 0.3423(2) 0.0391(10) Uani 1 1 d . . . . .
C20 C 0.2433(3) 1.0672(7) 0.2335(2) 0.0372(10) Uani 1 1 d . . . . .
H20A H 0.301971 0.997740 0.229502 0.045 Uiso 1 1 calc R U . . .
H20B H 0.254377 1.194330 0.223415 0.045 Uiso 1 1 calc R U . . .
C24 C -0.0303(3) 1.0487(7) 0.1172(2) 0.0375(10) Uani 1 1 d . . . . .
H24 H -0.019010 1.067974 0.067679 0.045 Uiso 1 1 calc R U . . .
C2 C 0.9151(3) -0.0064(7) 0.5717(2) 0.0350(10) Uani 1 1 d . . . . .
H2A H 0.950792 -0.114907 0.562837 0.042 Uiso 1 1 calc R U . . .
H2B H 0.957378 0.098584 0.569263 0.042 Uiso 1 1 calc R U . . .
C26 C -0.1392(3) 0.7891(11) 0.0755(2) 0.0578(17) Uani 1 1 d . . . . .
H26A H -0.197976 0.846883 0.085331 0.069 Uiso 1 1 calc R U . . .
H26B H -0.143431 0.659047 0.084057 0.069 Uiso 1 1 calc R U . . .
C8 C 0.5075(3) 0.0336(9) 0.3984(2) 0.0423(11) Uani 1 1 d . . . . .
H8A H 0.466359 0.120516 0.416634 0.051 Uiso 1 1 calc R U . . .
H8B H 0.474528 -0.084643 0.395403 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6080(4) 0.3511(8) 0.4722(3) 0.0591(15) Uani 1 1 d . . . . .
H7A H 0.551191 0.375723 0.428713 0.089 Uiso 1 1 calc R U . . .
H7B H 0.653136 0.454577 0.482143 0.089 Uiso 1 1 calc R U . . .
H7C H 0.583541 0.328620 0.515238 0.089 Uiso 1 1 calc R U . . .
C25 C -0.1178(4) 1.1634(11) 0.1240(3) 0.073(2) Uani 1 1 d . . . . .
H25A H -0.177196 1.136508 0.082774 0.110 Uiso 1 1 calc R U . . .
H25B H -0.100671 1.290298 0.122480 0.110 Uiso 1 1 calc R U . . .
H25C H -0.131803 1.137130 0.171043 0.110 Uiso 1 1 calc R U . . .


_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
Cl2 O7 1.430(4) . ?
Cl2 O6 1.434(3) . ?
Cl2 O5 1.438(3) . ?
Cl2 O8 1.443(3) . ?
Cl1 O3 1.418(3) . ?
Cl1 O4 1.447(3) . ?
Cl1 O1 1.425(3) . ?
Cl1 O2 1.420(4) . ?
Cl3 O10 1.440(3) . ?
Cl3 O12 1.433(3) . ?
Cl3 O9 1.450(3) . ?
Cl3 O11 1.422(4) . ?
N7 H7 1.0000 . ?
N7 C16 1.496(5) . ?
N7 C17 1.493(5) . ?
N7 C15 1.498(5) . ?
N10 H10 1.0000 . ?
N10 C21 1.491(6) . ?
N10 C22 1.496(5) . ?
N10 C20 1.499(5) . ?
N2 H2 1.0000 . ?
N2 C3 1.499(6) . ?
N2 C4 1.493(5) . ?
N2 C2 1.495(5) . ?
N6 C12 1.456(6) . ?
N6 C13 1.475(5) . ?
N6 C11 1.456(5) . ?
N1 C1 1.130(5) . ?
N3 C5 1.458(6) . ?
N3 C6 1.470(6) . ?
N3 C8 1.453(5) . ?
N11 C23 1.467(6) . ?
N11 C24 1.458(7) . ?
N11 C26 1.459(5) . ?
N4 C9 1.137(5) . ?
N9 C19 1.130(5) . ?
N8 C18 1.133(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C16 1.512(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C5 1.520(6) . ?
C19 C20 1.476(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N5 C10 1.134(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C23 1.504(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.474(5) . ?
C1 C2 1.473(5) . ?
C13 H13 1.0000 . ?
C13 C14 1.520(6) . ?
C13 C15 1.529(5) . ?
C9 C8 1.484(5) . ?
N12 C27 1.135(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C6 1.523(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C27 C26 1.494(6) . ?
C6 H6 1.0000 . ?
C6 C7 1.519(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.496(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C24 1.522(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C24 H24 1.0000 . ?
C24 C25 1.526(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
O7 Cl2 O6 110.1(2) . . ?
O7 Cl2 O5 109.9(3) . . ?
O7 Cl2 O8 109.4(2) . . ?
O6 Cl2 O5 110.0(2) . . ?
O6 Cl2 O8 109.1(2) . . ?
O5 Cl2 O8 108.3(2) . . ?
O3 Cl1 O4 109.5(2) . . ?
O3 Cl1 O1 109.9(3) . . ?
O3 Cl1 O2 109.1(2) . . ?
O1 Cl1 O4 107.44(18) . . ?
O2 Cl1 O4 109.3(3) . . ?
O2 Cl1 O1 111.6(3) . . ?
O10 Cl3 O9 108.71(19) . . ?
O12 Cl3 O10 109.3(2) . . ?
O12 Cl3 O9 108.9(2) . . ?
O11 Cl3 O10 110.2(2) . . ?
O11 Cl3 O12 109.6(2) . . ?
O11 Cl3 O9 110.1(2) . . ?
C16 N7 H7 107.1 . . ?
C16 N7 C15 109.6(3) . . ?
C17 N7 H7 107.1 . . ?
C17 N7 C16 111.8(3) . . ?
C17 N7 C15 113.7(3) . . ?
C15 N7 H7 107.1 . . ?
C21 N10 H10 107.2 . . ?
C21 N10 C22 110.0(3) . . ?
C21 N10 C20 113.7(3) . . ?
C22 N10 H10 107.2 . . ?
C22 N10 C20 111.2(3) . . ?
C20 N10 H10 107.2 . . ?
C3 N2 H2 107.2 . . ?
C4 N2 H2 107.2 . . ?
C4 N2 C3 109.8(3) . . ?
C4 N2 C2 112.6(3) . . ?
C2 N2 H2 107.2 . . ?
C2 N2 C3 112.6(3) . . ?
C12 N6 C13 110.0(3) . . ?
C11 N6 C12 110.6(3) . . ?
C11 N6 C13 113.0(3) . . ?
C5 N3 C6 111.0(3) . . ?
C8 N3 C5 112.1(4) . . ?
C8 N3 C6 113.0(4) . . ?
C24 N11 C23 110.7(3) . . ?
C24 N11 C26 114.2(4) . . ?
C26 N11 C23 110.5(4) . . ?
N6 C12 H12A 109.7 . . ?
N6 C12 H12B 109.7 . . ?
N6 C12 C16 110.1(3) . . ?
H12A C12 H12B 108.2 . . ?
C16 C12 H12A 109.7 . . ?
C16 C12 H12B 109.7 . . ?
N7 C16 C12 108.5(3) . . ?
N7 C16 H16A 110.0 . . ?
N7 C16 H16B 110.0 . . ?
C12 C16 H16A 110.0 . . ?
C12 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
N2 C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
N2 C3 C5 108.5(3) . . ?
H3A C3 H3B 108.4 . . ?
C5 C3 H3A 110.0 . . ?
C5 C3 H3B 110.0 . . ?
N9 C19 C20 179.3(5) . . ?
N3 C5 C3 109.3(3) . . ?
N3 C5 H5A 109.8 . . ?
N3 C5 H5B 109.8 . . ?
C3 C5 H5A 109.8 . . ?
C3 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N10 C21 H21A 109.8 . . ?
N10 C21 H21B 109.8 . . ?
N10 C21 C23 109.6(4) . . ?
H21A C21 H21B 108.2 . . ?
C23 C21 H21A 109.8 . . ?
C23 C21 H21B 109.8 . . ?
N7 C17 H17A 109.4 . . ?
N7 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 N7 111.2(3) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
N1 C1 C2 176.8(5) . . ?
N6 C13 H13 109.0 . . ?
N6 C13 C14 113.0(3) . . ?
N6 C13 C15 109.2(3) . . ?
C14 C13 H13 109.0 . . ?
C14 C13 C15 107.5(3) . . ?
C15 C13 H13 109.0 . . ?
N8 C18 C17 178.3(5) . . ?
N4 C9 C8 178.1(5) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
N2 C4 C6 111.0(3) . . ?
H4A C4 H4B 108.0 . . ?
C6 C4 H4A 109.4 . . ?
C6 C4 H4B 109.4 . . ?
N11 C23 C21 111.0(4) . . ?
N11 C23 H23A 109.4 . . ?
N11 C23 H23B 109.4 . . ?
C21 C23 H23A 109.4 . . ?
C21 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N7 C15 C13 110.5(3) . . ?
N7 C15 H15A 109.5 . . ?
N7 C15 H15B 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N12 C27 C26 178.5(5) . . ?
N3 C6 C4 108.7(3) . . ?
N3 C6 H6 109.4 . . ?
N3 C6 C7 112.3(4) . . ?
C4 C6 H6 109.4 . . ?
C7 C6 C4 107.5(3) . . ?
C7 C6 H6 109.4 . . ?
N6 C11 H11A 109.0 . . ?
N6 C11 H11B 109.0 . . ?
N6 C11 C10 113.0(3) . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
N10 C22 H22A 109.5 . . ?
N10 C22 H22B 109.5 . . ?
N10 C22 C24 110.6(3) . . ?
H22A C22 H22B 108.1 . . ?
C24 C22 H22A 109.5 . . ?
C24 C22 H22B 109.5 . . ?
N5 C10 C11 176.4(5) . . ?
N10 C20 H20A 109.4 . . ?
N10 C20 H20B 109.4 . . ?
C19 C20 N10 110.9(3) . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N11 C24 C22 109.2(3) . . ?
N11 C24 H24 109.9 . . ?
N11 C24 C25 111.3(5) . . ?
C22 C24 H24 109.9 . . ?
C22 C24 C25 106.7(4) . . ?
C25 C24 H24 109.9 . . ?
N2 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C1 C2 N2 112.4(3) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N11 C26 C27 113.0(4) . . ?
N11 C26 H26A 109.0 . . ?
N11 C26 H26B 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
N3 C8 C9 115.5(3) . . ?
N3 C8 H8A 108.4 . . ?
N3 C8 H8B 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
N7 H7 N4 1.00 2.25 3.001(5) 130.7 . yes
N10 H10 O9 1.00 1.98 2.893(4) 151.3 . yes
N2 H2 O4 1.00 1.81 2.791(4) 166.1 . yes

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
N10 C21 C23 N11 -58.1(5) . . . . ?
N10 C22 C24 N11 58.1(4) . . . . ?
N10 C22 C24 C25 178.5(4) . . . . ?
N2 C3 C5 N3 -61.0(4) . . . . ?
N2 C4 C6 N3 56.7(4) . . . . ?
N2 C4 C6 C7 178.5(4) . . . . ?
N6 C12 C16 N7 -61.9(4) . . . . ?
N6 C13 C15 N7 57.0(4) . . . . ?
C12 N6 C13 C14 -179.1(3) . . . . ?
C12 N6 C13 C15 -59.5(4) . . . . ?
C12 N6 C11 C10 -65.2(5) . . . . ?
C16 N7 C17 C18 -61.7(5) . . . . ?
C16 N7 C15 C13 -57.3(4) . . . . ?
C3 N2 C4 C6 -57.2(4) . . . . ?
C3 N2 C2 C1 -65.9(5) . . . . ?
C5 N3 C6 C4 -59.7(4) . . . . ?
C5 N3 C6 C7 -178.6(3) . . . . ?
C5 N3 C8 C9 -72.5(6) . . . . ?
C21 N10 C22 C24 -57.2(4) . . . . ?
C21 N10 C20 C19 -62.1(5) . . . . ?
C17 N7 C16 C12 -174.3(3) . . . . ?
C17 N7 C15 C13 176.8(3) . . . . ?
C13 N6 C12 C16 62.8(4) . . . . ?
C13 N6 C11 C10 58.7(5) . . . . ?
C4 N2 C3 C5 58.4(4) . . . . ?
C4 N2 C2 C1 58.9(5) . . . . ?
C23 N11 C24 C22 -59.2(4) . . . . ?
C23 N11 C24 C25 -176.8(3) . . . . ?
C23 N11 C26 C27 -70.4(7) . . . . ?
C14 C13 C15 N7 -180.0(3) . . . . ?
C15 N7 C16 C12 58.7(4) . . . . ?
C15 N7 C17 C18 63.0(4) . . . . ?
C6 N3 C5 C3 62.8(4) . . . . ?
C6 N3 C8 C9 53.9(6) . . . . ?
C11 N6 C12 C16 -171.7(3) . . . . ?
C11 N6 C13 C14 56.7(4) . . . . ?
C11 N6 C13 C15 176.3(3) . . . . ?
C22 N10 C21 C23 56.6(4) . . . . ?
C22 N10 C20 C19 62.7(5) . . . . ?
C20 N10 C21 C23 -178.0(3) . . . . ?
C20 N10 C22 C24 176.0(3) . . . . ?
C24 N11 C23 C21 60.2(4) . . . . ?
C24 N11 C26 C27 55.2(7) . . . . ?
C2 N2 C3 C5 -175.3(3) . . . . ?
C2 N2 C4 C6 176.4(3) . . . . ?
C26 N11 C23 C21 -172.2(4) . . . . ?
C26 N11 C24 C22 175.3(3) . . . . ?
C26 N11 C24 C25 57.7(4) . . . . ?
C8 N3 C5 C3 -169.8(3) . . . . ?
C8 N3 C6 C4 173.3(3) . . . . ?
C8 N3 C6 C7 54.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.155
_oxdiff_exptl_absorpt_empirical_full_min 0.158
####################################################################### 
# 
# 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_ysj-220930-2-298k_auto
_database_code_depnum_ccdc_archive 'CCDC 2321377'
loop_
_audit_author_name
_audit_author_address
'Shu Jing Yang'
;Nan Chang university
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl O4, C9 H15 N4'
_chemical_formula_sum            'C9 H15 Cl N4 O4'
_chemical_formula_weight         278.70
_chemical_absolute_configuration S
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8528(6)
_cell_length_b                   7.5471(7)
_cell_length_c                   9.7043(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.654(7)
_cell_angle_gamma                90
_cell_volume                     642.60(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4176
_cell_measurement_temperature    297.99(10)
_cell_measurement_theta_max      30.4020
_cell_measurement_theta_min      2.1650
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9594
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         2.117
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  24.00   0.50    1.03    --   -5.29 -99.00-180.00   74
  2  ω    -32.00  -7.00   0.50    1.03    --   -5.29 -86.00-142.00   50
  3  ω    -78.00   3.00   0.50    1.03    --   -5.29 -37.00 -30.00  162
  4  ω    -18.00  62.00   0.50    1.03    --   -5.29  19.00 -60.00  160
  5  ω    -27.00  10.00   0.50    1.03    --   -5.29  86.00 -23.00   74
  6  ω     -2.00  39.00   0.50    1.03    --    5.29  37.00-150.00   82
  7  ω     42.00  70.00   0.50    1.03    --    5.29  37.00-150.00   56
  8  ω    -13.00  26.00   0.50    1.03    --    5.29 -86.00-142.00   78
  9  ω    -18.00  38.00   0.50    1.03    --    5.29 -99.00 120.00  112
 10  ω     -8.00  12.00   0.50    1.03    --    5.29  86.00 -23.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297372000
_diffrn_orient_matrix_UB_12      0.0867993000
_diffrn_orient_matrix_UB_13      -0.0043529000
_diffrn_orient_matrix_UB_21      -0.0315503000
_diffrn_orient_matrix_UB_22      0.0242784000
_diffrn_orient_matrix_UB_23      0.0607482000
_diffrn_orient_matrix_UB_31      0.0682655000
_diffrn_orient_matrix_UB_32      -0.0265628000
_diffrn_orient_matrix_UB_33      0.0415323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.720
_reflns_number_gt                2051
_reflns_number_total             3179
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 686 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1306P)²+0.1856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C2-C1 = C1A-C2A
 1.461 with sigma of 0.00001
 C3-C4
 1.5 with sigma of 0.0001
 C5-C6 = C7-C4
 1.54 with sigma of 0.00001
 N3-C7 = N3-C6 = N2-C5 = N2-C4
 1.47 with sigma of 0.0001
2. Rigid bond restraints
 C2, C2A, C1A, C1, N1, N1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim C2 \\sim C2A \\sim C1 \\sim N1: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.01 within 2A
4. Rigid body (RIGU) restrains
 C2A, C2, C1, N1, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1A, N1, C1, C1A, C2, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=1-FVAR(1)
 Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
 Sof(N1A)=1-FVAR(2)
 Sof(N1)=FVAR(2)
 Fixed Sof: C1(0.5) C1A(0.5)
6.a Ternary CH refined with riding coordinates:
 N3(H3), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C6(H6A,H6B), C2(H2A,H2B), C5(H5A,H5B), C2A(H2AA,H2AB)
6.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.28735(12) 0.5706(5) 0.82607(13) 0.0767(6) Uani 1 1 d . . . . .
N3 N 0.7027(3) 0.5849(3) 0.8318(3) 0.0535(9) Uani 1 1 d D . . . .
H3 H 0.593480 0.583034 0.797585 0.064 Uiso 1 1 calc R U . . .
C4 C 0.7384(4) 0.4214(3) 0.61613(4) 0.079(2) Uani 1 1 d D . . . .
H4 H 0.628252 0.416234 0.586435 0.095 Uiso 1 1 calc R U . . .
O1 O 0.3879(4) 0.5686(15) 0.7236(5) 0.1039(16) Uani 1 1 d . . . . .
C7 C 0.7709(5) 0.4273(4) 0.77596(4) 0.0596(16) Uani 1 1 d D . . . .
H7A H 0.729928 0.321622 0.814140 0.072 Uiso 1 1 calc R U . . .
H7B H 0.880225 0.428423 0.804298 0.072 Uiso 1 1 calc R U . . .
N4 N 1.0000(5) 0.5796(13) 1.1021(5) 0.0821(14) Uani 1 1 d . . . . .
N2 N 0.8015(4) 0.5856(3) 0.5656(4) 0.0973(19) Uani 1 1 d D U . . .
C9 C 0.8787(6) 0.5801(16) 1.0485(5) 0.0730(14) Uani 1 1 d . . . . .
O2 O 0.3727(6) 0.561(2) 0.9553(6) 0.145(3) Uani 1 1 d . . . . .
O3 O 0.1833(11) 0.4394(19) 0.8063(14) 0.191(5) Uani 1 1 d . . . . .
O4 O 0.1945(15) 0.7244(18) 0.8091(10) 0.183(5) Uani 1 1 d . . . . .
C8 C 0.7186(6) 0.587(2) 0.9863(6) 0.108(3) Uani 1 1 d . . . . .
H8A H 0.672098 0.693774 1.016831 0.130 Uiso 1 1 calc R U . . .
H8B H 0.664844 0.486100 1.018196 0.130 Uiso 1 1 calc R U . . .
C6 C 0.7656(5) 0.7487(4) 0.78042(5) 0.089(3) Uani 1 1 d D . . . .
H6A H 0.874916 0.754534 0.808080 0.106 Uiso 1 1 calc R U . . .
H6B H 0.718803 0.851943 0.816614 0.106 Uiso 1 1 calc R U . . .
N1 N 0.498(3) 0.612(5) 0.302(3) 0.100(7) Uani 0.54(9) 1 d . U P A 1
C3 C 0.8124(8) 0.2534(6) 0.5767(9) 0.209(10) Uani 1 1 d D . . . .
H3A H 0.904465 0.281254 0.539100 0.313 Uiso 1 1 calc R U . . .
H3B H 0.743974 0.191128 0.508270 0.313 Uiso 1 1 calc R U . . .
H3C H 0.836062 0.180150 0.657631 0.313 Uiso 1 1 calc R U . . .
C1 C 0.62357(6) 0.6518(5) 0.35131(14) 0.091(4) Uani 0.5 1 d D U P A 1
C2 C 0.77884(6) 0.6740(5) 0.42176(14) 0.093(4) Uani 0.36(2) 1 d D U P A 1
H2A H 0.801410 0.799415 0.432224 0.112 Uiso 0.36(2) 1 calc R U P A 1
H2B H 0.849840 0.622932 0.364853 0.112 Uiso 0.36(2) 1 calc R U P A 1
C5 C 0.7282(5) 0.7400(4) 0.62098(5) 0.107(4) Uani 1 1 d D . . . .
H5A H 0.618697 0.732277 0.595396 0.128 Uiso 1 1 calc R U . . .
H5B H 0.763358 0.847402 0.580488 0.128 Uiso 1 1 calc R U . . .
C2A C 0.79391(6) 0.5406(13) 0.41291(13) 0.095(4) Uani 0.64(2) 1 d D U P A 2
H2AA H 0.851277 0.628775 0.368863 0.114 Uiso 0.64(2) 1 calc R U P A 2
H2AB H 0.842876 0.426935 0.404317 0.114 Uiso 0.64(2) 1 calc R U P A 2
C1A C 0.63943(6) 0.5326(12) 0.33829(13) 0.080(4) Uani 0.5 1 d D U P . .
N1A N 0.529(4) 0.507(14) 0.283(2) 0.12(2) Uani 0.46(9) 1 d . U P A 2


_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
Cl1 O1 1.420(4) . ?
Cl1 O2 1.378(5) . ?
Cl1 O3 1.349(9) . ?
Cl1 O4 1.419(9) . ?
N3 H3 0.9800 . ?
N3 C7 1.46999(17) . ?
N3 C8 1.487(6) . ?
N3 C6 1.47000(18) . ?
C4 H4 0.9800 . ?
C4 C7 1.54000(12) . ?
C4 N2 1.46998(17) . ?
C4 C3 1.50000(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N4 C9 1.129(6) . ?
N2 C2 1.536(4) . ?
N2 C5 1.46999(17) . ?
N2 C2A 1.513(4) . ?
C9 C8 1.465(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.54000(13) . ?
N1 C1 1.19(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 C2 1.46100(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C1A 1.46100(12) . ?
C1A N1A 1.07(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 Cl1 O1 108.5(3) . . ?
O2 Cl1 O4 112.9(8) . . ?
O3 Cl1 O1 111.8(6) . . ?
O3 Cl1 O2 111.8(8) . . ?
O3 Cl1 O4 102.1(7) . . ?
O4 Cl1 O1 109.6(6) . . ?
C7 N3 H3 107.4 . . ?
C7 N3 C8 113.0(6) . . ?
C8 N3 H3 107.4 . . ?
C6 N3 H3 107.4 . . ?
C6 N3 C7 111.3(3) . . ?
C6 N3 C8 110.1(6) . . ?
C7 C4 H4 110.0 . . ?
N2 C4 H4 110.0 . . ?
N2 C4 C7 106.4(2) . . ?
N2 C4 C3 115.4(4) . . ?
C3 C4 H4 110.0 . . ?
C3 C4 C7 104.6(4) . . ?
N3 C7 C4 111.3(2) . . ?
N3 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C4 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C4 N2 C2 131.3(3) . . ?
C4 N2 C5 109.9(3) . . ?
C4 N2 C2A 99.7(4) . . ?
C5 N2 C2 88.69(19) . . ?
C5 N2 C2A 124.9(4) . . ?
N4 C9 C8 176.5(8) . . ?
N3 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C9 C8 N3 111.8(4) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N3 C6 H6A 110.7 . . ?
N3 C6 H6B 110.7 . . ?
N3 C6 C5 105.3(2) . . ?
H6A C6 H6B 108.8 . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C1 C2 171.4(14) . . ?
N2 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
C1 C2 N2 112.1(2) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C5 C6 110.8(3) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N2 C2A H2AA 108.7 . . ?
N2 C2A H2AB 108.7 . . ?
H2AA C2A H2AB 107.6 . . ?
C1A C2A N2 114.28(19) . . ?
C1A C2A H2AA 108.7 . . ?
C1A C2A H2AB 108.7 . . ?
N1A C1A C2A 172(6) . . ?

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
N3 H3 O1 0.98 1.87 2.847(5) 176.2 . yes

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 C6 C5 N2 -61.4(4) . . . . ?
C4 N2 C2 C1 35.8(4) . . . . ?
C4 N2 C5 C6 64.4(4) . . . . ?
C4 N2 C2A C1A 69.7(7) . . . . ?
C7 N3 C8 C9 58.7(12) . . . . ?
C7 N3 C6 C5 59.4(4) . . . . ?
C7 C4 N2 C2 -166.3(3) . . . . ?
C7 C4 N2 C5 -59.7(3) . . . . ?
C7 C4 N2 C2A 167.6(3) . . . . ?
N2 C4 C7 N3 58.3(4) . . . . ?
C8 N3 C7 C4 174.4(4) . . . . ?
C8 N3 C6 C5 -174.4(4) . . . . ?
C6 N3 C7 C4 -61.0(4) . . . . ?
C6 N3 C8 C9 -66.5(12) . . . . ?
C3 C4 C7 N3 -179.0(4) . . . . ?
C3 C4 N2 C2 78.2(5) . . . . ?
C3 C4 N2 C5 -175.2(4) . . . . ?
C3 C4 N2 C2A 52.0(4) . . . . ?
C2 N2 C5 C6 -161.6(3) . . . . ?
C5 N2 C2 C1 -79.9(3) . . . . ?
C5 N2 C2A C1A -53.0(8) . . . . ?
C2A N2 C5 C6 -177.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.268
_oxdiff_exptl_absorpt_empirical_full_min 0.331
