# Electronic Supplementary Material (ESI) for Nanoscale.
# 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_exp_332-hbaclo4
_audit_block_doi                 10.5517/ccdc.csd.cc28d0d3
_database_code_depnum_ccdc_archive 'CCDC 2096914'
loop_
_audit_author_name
_audit_author_address
'ZhangRan Gao'
;Nanjing University
China
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'Cl O4, C3 H8 N'
_chemical_formula_sum            'C3 H8 Cl N O4'
_chemical_formula_weight         157.55
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.100(2)
_cell_length_b                   8.269(2)
_cell_length_c                   9.997(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.57(3)
_cell_angle_gamma                90
_cell_volume                     660.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    995
_cell_measurement_theta_max      26.6410
_cell_measurement_theta_min      2.4990
_exptl_crystal_description       lamellar
_exptl_crystal_colour            colorless
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.5850
_exptl_crystal_F_000             328.8085
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5242
_diffrn_reflns_theta_full        30.1788
_diffrn_reflns_theta_max         30.18
_diffrn_reflns_theta_min         2.55
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9467
_diffrn_measured_fraction_theta_max 0.9414
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  28.00   0.50    0.70    --   20.00  54.00   0.00   50
  2  ω     62.00 110.00   0.50    0.70    --   20.00  54.00   0.00   96
  3  ω    -73.00 -32.00   0.50    0.70    --   20.00  54.00 -90.00   82
  4  ω     -9.00  26.00   0.50    0.70    --   20.00  54.00 -90.00   70
  5  ω     66.00  92.00   0.50    0.70    --   20.00  54.00 -90.00   52
  6  ω    -74.00 107.00   0.50    0.70    --   20.00  54.00-150.00  362
  7  ω    -62.00 -37.00   0.50    0.70    --   20.00  54.00 -60.00   50
  8  ω     66.00  92.00   0.50    0.70    --   20.00  54.00 -60.00   52
  9  ω      4.00  59.00   0.50    0.70    --   20.00  54.00-120.00  110
 10  ω     75.00 100.00   0.50    0.70    --   20.00  54.00-120.00   50
 11  ω    -72.00 -46.00   0.50    0.70    --   20.00  54.00   0.00   52
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0029371000
_diffrn_orient_matrix_UB_12      0.0855030000
_diffrn_orient_matrix_UB_13      -0.0046781000
_diffrn_orient_matrix_UB_21      -0.0244582000
_diffrn_orient_matrix_UB_22      -0.0050955000
_diffrn_orient_matrix_UB_23      -0.0713207000
_diffrn_orient_matrix_UB_31      -0.0853220000
_diffrn_orient_matrix_UB_32      0.0045691000
_diffrn_orient_matrix_UB_33      0.0080386000
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1099
_reflns_number_total             1847
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.6511
_refine_diff_density_min         -0.8572
_refine_diff_density_rms         0.1678
_refine_ls_d_res_high            0.7069
_refine_ls_d_res_low             7.9872
_refine_ls_goodness_of_fit_ref   0.9533
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0753
_refine_ls_restrained_S_all      0.9533
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1403P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.2248
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b)
2.c Idealised Me refined as rotating group:
 N9(H9a,H9b,H9c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Cl2 Cl 0.34984(8) 0.24762(9) 0.47640(7) 0.0416(3) Uani 1.000000 .
O1 O 0.3599(4) 0.2502(3) 0.3347(3) 0.0647(8) Uani 1.000000 .
O3 O 0.5069(3) 0.1900(4) 0.5490(3) 0.0664(8) Uani 1.000000 .
N9 N 0.3308(3) 0.5882(4) 0.2289(2) 0.0503(7) Uani 1.000000 .
H9a H 0.3782(10) 0.594(2) 0.1548(6) 0.0603(9) Uiso 1.000000 GR
H9b H 0.3904(8) 0.6459(16) 0.2951(15) 0.0603(9) Uiso 1.000000 GR
H9c H 0.3274(3) 0.4855(8) 0.255(2) 0.0603(9) Uiso 1.000000 GR
O5 O 0.2205(3) 0.1415(4) 0.5005(3) 0.0722(8) Uani 1.000000 .
O4 O 0.3186(4) 0.4062(4) 0.5205(3) 0.0794(9) Uani 1.000000 .
C6 C 0.1595(4) 0.6530(4) 0.1988(3) 0.0452(7) Uani 1.000000 .
H6 H 0.0824(4) 0.5943(4) 0.1296(3) 0.0542(9) Uiso 1.000000 R
C7 C 0.1356(5) 0.8286(5) 0.2013(4) 0.0632(10) Uani 1.000000 .
H7a H 0.2341(5) 0.8958(5) 0.2258(4) 0.0758(12) Uiso 1.000000 R
H7b H 0.0482(5) 0.8753(5) 0.1343(4) 0.0758(12) Uiso 1.000000 R
C8 C 0.0839(5) 0.7254(5) 0.3082(5) 0.0634(11) Uani 1.000000 .
H8a H -0.0350(5) 0.7091(5) 0.3066(5) 0.0761(13) Uiso 1.000000 R
H8b H 0.1509(5) 0.7296(5) 0.3981(5) 0.0761(13) Uiso 1.000000 R


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 O1 1.433(3) . ?
Cl2 O3 1.437(2) . ?
Cl2 O5 1.418(3) . ?
Cl2 O4 1.419(3) . ?
N9 H9a 0.8900 . ?
N9 H9b 0.8900 . ?
N9 H9c 0.8900 . ?
N9 C6 1.471(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.465(5) . ?
C6 C8 1.467(5) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 C8 1.482(6) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cl2 O1 108.24(18) . . ?
O5 Cl2 O1 110.02(18) . . ?
O5 Cl2 O3 109.04(17) . . ?
O4 Cl2 O1 109.61(17) . . ?
O4 Cl2 O3 109.76(17) . . ?
O4 Cl2 O5 110.14(18) . . ?
H9b N9 H9a 109.5 . . ?
H9c N9 H9a 109.5 . . ?
H9c N9 H9b 109.5 . . ?
C6 N9 H9a 109.5 . . ?
C6 N9 H9b 109.5 . . ?
C6 N9 H9c 109.5 . . ?
H6 C6 N9 115.62(16) . . ?
C7 C6 N9 118.7(3) . . ?
C7 C6 H6 115.62(18) . . ?
C8 C6 N9 119.5(3) . . ?
C8 C6 H6 115.6(2) . . ?
C8 C6 C7 60.7(2) . . ?
H7a C7 C6 117.80(19) . . ?
H7b C7 C6 117.80(18) . . ?
H7b C7 H7a 114.9 . . ?
C8 C7 C6 59.7(2) . . ?
C8 C7 H7a 117.8(2) . . ?
C8 C7 H7b 117.8(2) . . ?
C7 C8 C6 59.6(3) . . ?
H8a C8 C6 117.8(2) . . ?
H8a C8 C7 117.8(2) . . ?
H8b C8 C6 117.8(2) . . ?
H8b C8 C7 117.8(2) . . ?
H8b C8 H8a 115.0 . . ?

_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 2.742
_oxdiff_exptl_absorpt_empirical_full_min 0.495
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2096917'
loop_
_audit_author_name
_audit_author_address
'ZhangRan Gao'
;Nanjing University
China
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Cl N O4'
_chemical_formula_weight         157.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.9117(4)
_cell_length_b                   8.1838(6)
_cell_length_c                   8.0560(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.683(9)
_cell_angle_gamma                90
_cell_volume                     319.21(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    195(2)
_cell_measurement_reflns_used    995
_cell_measurement_theta_min      2.4990
_cell_measurement_theta_max      26.6410

_exptl_crystal_description       lamellar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.540
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      195(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 924 diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2624
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         29.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1338
_reflns_number_gt                1107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.839
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1114P)²+0.3162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1338
_refine_ls_number_parameters     89
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1923
_refine_ls_wR_factor_gt          0.1734
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.5514(2) 0.4589(3) 0.64924(15) 0.0242(4) Uani 1 1 d . . . . .
O4 O 0.448(3) 0.2987(18) 0.6693(14) 0.028(2) Uani 0.5 1 d . . P A 1
O4' O 0.512(3) 0.3519(16) 0.7789(13) 0.028(2) Uani 0.5 1 d . . P A 2
O1 O 0.8425(8) 0.4572(14) 0.6437(6) 0.0350(10) Uani 1 1 d . . . . .
O2 O 0.477(2) 0.5976(14) 0.7341(16) 0.116(7) Uani 1 1 d . . . . .
O3 O 0.419(3) 0.401(2) 0.490(2) 0.0346(15) Uani 0.5 1 d . . P A 1
O3' O 0.401(3) 0.521(2) 0.487(2) 0.0346(15) Uani 0.5 1 d . . P A 2
N1 N -0.0507(12) 0.3003(8) 0.3318(8) 0.0321(14) Uani 1 1 d . . . . .
H1A H -0.2006 0.2484 0.3526 0.048 Uiso 1 1 calc R U . . .
H1B H 0.0921 0.2318 0.3464 0.048 Uiso 1 1 calc R U . . .
H1C H -0.0143 0.3844 0.4021 0.048 Uiso 1 1 calc R U . . .
C1 C -0.100(2) 0.5473(15) 0.1434(18) 0.046(3) Uani 1 1 d . . . . .
H1D H -0.2340 0.6033 0.0609 0.055 Uiso 1 1 calc R U . . .
H1E H -0.0541 0.6024 0.2511 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1214(14) 0.455(3) 0.0821(9) 0.051(2) Uani 1 1 d . . . . .
H2A H 0.3026 0.4545 0.1520 0.061 Uiso 1 1 calc R U . . .
H2B H 0.1229 0.4554 -0.0382 0.061 Uiso 1 1 calc R U . . .
C3 C -0.103(2) 0.3650(13) 0.1433(11) 0.028(2) Uani 1 1 d . . . . .
H3 H -0.2406 0.3088 0.0607 0.034 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
Cl1 O2 1.405(10) . ?
Cl1 O4' 1.401(11) . ?
Cl1 O4 1.425(14) . ?
Cl1 O3 1.421(14) . ?
Cl1 O1 1.438(4) . ?
Cl1 O3' 1.479(16) . ?
O4 O3 1.66(2) . ?
N1 C3 1.588(11) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C2 1.473(18) . ?
C1 C3 1.492(8) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C2 C3 1.479(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3 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
O2 Cl1 O4' 93.6(8) . . ?
O2 Cl1 O4 124.1(6) . . ?
O2 Cl1 O3 126.4(9) . . ?
O4 Cl1 O3 71.2(9) . . ?
O2 Cl1 O1 111.4(6) . . ?
O4' Cl1 O1 106.2(7) . . ?
O4 Cl1 O1 111.7(8) . . ?
O3 Cl1 O1 105.9(8) . . ?
O2 Cl1 O3' 91.2(10) . . ?
O4' Cl1 O3' 139.8(9) . . ?
O1 Cl1 O3' 109.0(7) . . ?
Cl1 O4 O3 54.3(8) . . ?
Cl1 O3 O4 54.5(7) . . ?
C3 N1 H1A 109.5 . . ?
C3 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C3 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 C1 C3 59.8(11) . . ?
C2 C1 H1D 117.8 . . ?
C3 C1 H1D 117.8 . . ?
C2 C1 H1E 117.8 . . ?
C3 C1 H1E 117.8 . . ?
H1D C1 H1E 114.9 . . ?
C1 C2 C3 60.7(4) . . ?
C1 C2 H2A 117.7 . . ?
C3 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C3 C2 H2B 117.7 . . ?
H2A C2 H2B 114.8 . . ?
C2 C3 C1 59.4(11) . . ?
C2 C3 N1 118.5(7) . . ?
C1 C3 N1 109.4(10) . . ?
C2 C3 H3 118.4 . . ?
C1 C3 H3 118.4 . . ?
N1 C3 H3 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cl1 O4 O3 121.7(10) . . . . ?
O1 Cl1 O4 O3 -100.1(8) . . . . ?
O2 Cl1 O3 O4 -119.0(9) . . . . ?
O1 Cl1 O3 O4 108.0(8) . . . . ?
C1 C2 C3 N1 -96.9(11) . . . . ?
C2 C1 C3 N1 112.2(9) . . . . ?

_refine_diff_density_max         0.906
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.127

