# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_cu_petn_br_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2252052'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2.5 H4 Br N O3)'
_chemical_formula_sum            'C5 H8 Br2 N2 O6'
_chemical_formula_weight         351.95
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.8421(4)
_cell_length_b                   6.7381(2)
_cell_length_c                   12.6407(6)
_cell_angle_alpha                90
_cell_angle_beta                 120.534(2)
_cell_angle_gamma                90
_cell_volume                     1088.86(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4588
_cell_measurement_temperature    305.00
_cell_measurement_theta_max      70.00
_cell_measurement_theta_min      4.060
_shelx_estimated_absorpt_T_max   0.682
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    9.634
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1632 before and 0.1015 after correction.
The Ratio of minimum to maximum transmission is 0.6867.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.051
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11399
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.079
_diffrn_reflns_theta_min         4.060
_diffrn_ambient_temperature      305.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                1730
_reflns_number_total             1960
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.527
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.132
_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)+(0.0407P)²+1.4224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1(H1A,H1B), C2(H2A,H2B), C2A(H2AA,H2AB)
;
_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
Br1 Br 0.58795(8) 0.26592(15) 0.18304(10) 0.0519(4) Uani 1 1 d . . . . .
Br1A Br 0.36285(9) -0.06355(15) 0.34019(11) 0.0601(4) Uani 1 1 d . . . . .
O1A O 0.5668(5) 0.5072(10) 0.4288(6) 0.0465(17) Uani 1 1 d . . . . .
O1 O 0.6066(5) 0.8401(10) -0.0072(6) 0.0458(16) Uani 1 1 d . . . . .
O3 O 0.7601(6) 0.9278(13) 0.1533(7) 0.065(2) Uani 1 1 d . . . . .
O3A O 0.7328(6) 0.6008(14) 0.5290(8) 0.064(2) Uani 1 1 d . . . . .
O2A O 0.6217(7) 0.7287(12) 0.3521(7) 0.074(3) Uani 1 1 d . . . . .
N1 N 0.6988(6) 0.9526(13) 0.0475(9) 0.048(2) Uani 1 1 d . . . . .
N1A N 0.6479(7) 0.6211(13) 0.4391(8) 0.047(2) Uani 1 1 d . . . . .
C3A C 0.500000 0.251(2) 0.500000 0.033(2) Uani 1 2 d S T P . .
O2 O 0.7031(7) 1.0621(13) -0.0237(9) 0.075(3) Uani 1 1 d . . . . .
C1A C 0.5962(7) 0.3769(13) 0.5335(8) 0.038(2) Uani 1 1 d . . . . .
H1AA H 0.615987 0.454150 0.606893 0.045 Uiso 1 1 calc R U . . .
H1AB H 0.654629 0.293267 0.548283 0.045 Uiso 1 1 calc R U . . .
C1 C 0.5977(7) 0.7106(12) 0.0772(8) 0.037(2) Uani 1 1 d . . . . .
H1A H 0.590177 0.787121 0.137264 0.045 Uiso 1 1 calc R U . . .
H1B H 0.659332 0.627483 0.120135 0.045 Uiso 1 1 calc R U . . .
C2 C 0.4777(7) 0.4554(15) 0.0849(8) 0.040(2) Uani 1 1 d . . . . .
H2A H 0.412742 0.383729 0.035307 0.048 Uiso 1 1 calc R U . . .
H2B H 0.468040 0.542386 0.139538 0.048 Uiso 1 1 calc R U . . .
C3 C 0.500000 0.583(2) 0.000000 0.040(3) Uani 1 2 d S T P . .
C2A C 0.4760(7) 0.1240(16) 0.3873(8) 0.043(2) Uani 1 1 d . . . . .
H2AA H 0.538577 0.051676 0.404898 0.051 Uiso 1 1 calc R U . . .
H2AB H 0.458162 0.211443 0.318392 0.051 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
Br1 C2 1.946(9) . ?
Br1A C2A 1.938(10) . ?
O1A N1A 1.377(10) . ?
O1A C1A 1.458(11) . ?
O1 N1 1.400(10) . ?
O1 C1 1.436(10) . ?
O3 N1 1.186(11) . ?
O3A N1A 1.201(11) . ?
O2A N1A 1.205(11) . ?
N1 O2 1.192(11) . ?
C3A C1A 1.523(11) 2_656 ?
C3A C1A 1.523(11) . ?
C3A C2A 1.541(12) . ?
C3A C2A 1.541(12) 2_656 ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C3 1.536(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.535(12) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 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
N1A O1A C1A 114.0(7) . . ?
N1 O1 C1 113.4(7) . . ?
O3 N1 O1 118.6(8) . . ?
O3 N1 O2 129.3(9) . . ?
O2 N1 O1 112.1(8) . . ?
O3A N1A O1A 118.2(9) . . ?
O3A N1A O2A 129.0(9) . . ?
O2A N1A O1A 112.8(8) . . ?
C1A C3A C1A 112.4(11) 2_656 . ?
C1A C3A C2A 107.9(5) . 2_656 ?
C1A C3A C2A 108.1(5) 2_656 2_656 ?
C1A C3A C2A 108.1(5) . . ?
C1A C3A C2A 107.9(5) 2_656 . ?
C2A C3A C2A 112.5(11) . 2_656 ?
O1A C1A C3A 106.1(6) . . ?
O1A C1A H1AA 110.5 . . ?
O1A C1A H1AB 110.5 . . ?
C3A C1A H1AA 110.5 . . ?
C3A C1A H1AB 110.5 . . ?
H1AA C1A H1AB 108.7 . . ?
O1 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
O1 C1 C3 106.4(6) . . ?
H1A C1 H1B 108.6 . . ?
C3 C1 H1A 110.4 . . ?
C3 C1 H1B 110.4 . . ?
Br1 C2 H2A 108.8 . . ?
Br1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 Br1 113.7(6) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C3 C1 111.7(11) 2_655 . ?
C2 C3 C1 106.7(5) . 2_655 ?
C2 C3 C1 106.7(5) 2_655 . ?
C2 C3 C1 109.8(5) 2_655 2_655 ?
C2 C3 C1 109.8(5) . . ?
C2 C3 C2 112.1(11) . 2_655 ?
Br1A C2A H2AA 108.8 . . ?
Br1A C2A H2AB 108.8 . . ?
C3A C2A Br1A 113.8(6) . . ?
C3A C2A H2AA 108.8 . . ?
C3A C2A H2AB 108.8 . . ?
H2AA C2A H2AB 107.7 . . ?

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
Br1 C2 C3 C1 175.6(6) . . . 2_655 ?
Br1 C2 C3 C1 -63.1(10) . . . . ?
Br1 C2 C3 C2 55.3(4) . . . 2_655 ?
O1 C1 C3 C1 -55.6(5) . . . 2_655 ?
O1 C1 C3 C2 64.5(9) . . . 2_655 ?
O1 C1 C3 C2 -173.8(8) . . . . ?
N1 O1 C1 C3 -173.5(7) . . . . ?
N1A O1A C1A C3A -174.9(7) . . . . ?
C1A O1A N1A O3A 1.3(12) . . . . ?
C1A O1A N1A O2A -179.4(8) . . . . ?
C1A C3A C1A O1A -55.9(5) 2_656 . . . ?
C1A C3A C2A Br1A -63.4(9) 2_656 . . . ?
C1A C3A C2A Br1A 174.8(6) . . . . ?
C1 O1 N1 O3 2.2(12) . . . . ?
C1 O1 N1 O2 -178.3(8) . . . . ?
C2A C3A C1A O1A -174.9(8) 2_656 . . . ?
C2A C3A C1A O1A 63.2(9) . . . . ?
C2A C3A C2A Br1A 55.8(5) 2_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_cu_petn_i_1g_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2252053'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H7 I N3 O9, C5 H8 I N3 O9'
_chemical_formula_sum            'C10 H15 I2 N6 O18'
_chemical_formula_weight         761.08
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.7370(4)
_cell_length_b                   12.6197(7)
_cell_length_c                   27.5521(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2342.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2616
_cell_measurement_temperature    305.00
_cell_measurement_theta_max      55.15
_cell_measurement_theta_min      3.208
_shelx_estimated_absorpt_T_max   0.643
_shelx_estimated_absorpt_T_min   0.222
_exptl_absorpt_coefficient_mu    21.997
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1461 before and 0.0929 after correction.
The Ratio of minimum to maximum transmission is 0.6845.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1302
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24860
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_temperature      305.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2783
_reflns_number_total             4105
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.881
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details 
;
 Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(11)
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      0.976
_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)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1300
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C3(H3A,H3B), C4A(H4AA,H4AB), C4(H4A,H4B), C2A(H2AA,
 H2AB), C3A(H3AA,H3AB)
2.b Aromatic/amide H refined with riding coordinates:
 C1A(H1AA)
;
_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
I1A I 0.28075(14) 0.74313(9) 0.94741(4) 0.0648(4) Uani 1 1 d . . . . .
I1 I 1.20391(13) 0.50631(10) 0.55197(4) 0.0672(4) Uani 1 1 d . . . . .
O7 O 0.6421(13) 0.7246(9) 0.5931(3) 0.057(3) Uani 1 1 d . . . . .
O4 O 0.6261(13) 0.5189(9) 0.6604(3) 0.050(3) Uani 1 1 d . . . . .
O5 O 0.3931(16) 0.4267(10) 0.6924(4) 0.074(3) Uani 1 1 d . . . . .
O1A O 0.3100(14) 0.5813(9) 0.8276(3) 0.058(3) Uani 1 1 d . . . . .
O4A O 0.8562(12) 0.7427(9) 0.8382(3) 0.047(2) Uani 1 1 d . . . . .
O1 O 1.1771(15) 0.6754(8) 0.6678(4) 0.057(3) Uani 1 1 d . . . . .
O5A O 0.9144(14) 0.7419(9) 0.7580(3) 0.066(3) Uani 1 1 d . . . . .
O6 O 0.5813(15) 0.5172(9) 0.7401(3) 0.066(3) Uani 1 1 d . . . . .
O9A O 0.9036(17) 0.5149(10) 0.9795(4) 0.076(3) Uani 1 1 d . . . . .
O8A O 1.0695(16) 0.4243(11) 0.9275(4) 0.080(3) Uani 1 1 d . . . . .
O2 O 1.2342(19) 0.8496(11) 0.6757(5) 0.079(3) Uani 1 1 d . . . . .
O6A O 1.0986(15) 0.8334(9) 0.8061(4) 0.067(3) Uani 1 1 d . . . . .
O7A O 0.8504(15) 0.5383(9) 0.9016(3) 0.058(3) Uani 1 1 d . . . . .
N2A N 0.9641(17) 0.7761(10) 0.7969(4) 0.050(3) Uani 1 1 d . . . . .
N2 N 0.5275(17) 0.4869(10) 0.7027(4) 0.051(3) Uani 1 1 d . . . . .
O3 O 1.3894(16) 0.7358(12) 0.7203(4) 0.087(4) Uani 1 1 d . . . . .
N3A N 0.9458(18) 0.4887(11) 0.9400(4) 0.056(3) Uani 1 1 d . . . . .
O8 O 0.4357(17) 0.8413(10) 0.5663(4) 0.081(4) Uani 1 1 d . . . . .
O2A O 0.2611(18) 0.4087(11) 0.8187(4) 0.071(3) Uani 1 1 d . . . . .
N3 N 0.5447(15) 0.7711(11) 0.5539(5) 0.059(3) Uani 1 1 d . . . . .
O9 O 0.5705(18) 0.7349(11) 0.5138(4) 0.082(4) Uani 1 1 d . . . . .
C5A C 0.5866(17) 0.6466(11) 0.8735(4) 0.042(3) Uani 1 1 d . . . . .
N1A N 0.2160(17) 0.4934(13) 0.8071(4) 0.056(3) Uani 1 1 d . . . . .
C2 C 0.782(2) 0.5977(11) 0.6701(4) 0.046(3) Uani 1 1 d . . . . .
H2A H 0.868444 0.573504 0.696044 0.056 Uiso 1 1 calc R U . . .
H2B H 0.723673 0.664813 0.679620 0.056 Uiso 1 1 calc R U . . .
O3A O 0.0928(17) 0.5205(11) 0.7767(4) 0.083(4) Uani 1 1 d . . . . .
C5 C 0.8991(18) 0.6099(11) 0.6227(4) 0.043(3) Uani 1 1 d . . . . .
N1 N 1.2762(18) 0.7622(14) 0.6899(5) 0.068(4) Uani 1 1 d . . . . .
C1 C 1.0355(19) 0.7066(12) 0.6300(5) 0.049(4) Uani 1 1 d . . . . .
H1A H 1.104276 0.723834 0.600079 0.059 Uiso 1 1 calc R U . . .
H1B H 0.959153 0.767835 0.640215 0.059 Uiso 1 1 calc R U . . .
C3 C 0.7633(19) 0.6331(11) 0.5797(4) 0.049(4) Uani 1 1 d . . . . .
H3A H 0.841294 0.648775 0.551003 0.059 Uiso 1 1 calc R U . . .
H3B H 0.679428 0.572430 0.572899 0.059 Uiso 1 1 calc R U . . .
C4A C 0.465(2) 0.7487(13) 0.8842(5) 0.050(3) Uani 1 1 d . . . . .
H4AA H 0.381965 0.763684 0.856331 0.060 Uiso 1 1 calc R U . . .
H4AB H 0.557228 0.807312 0.887728 0.060 Uiso 1 1 calc R U . . .
C4 C 1.013(2) 0.5075(13) 0.6136(5) 0.052(3) Uani 1 1 d . . . . .
H4A H 0.917008 0.450561 0.609878 0.063 Uiso 1 1 calc R U . . .
H4B H 1.091503 0.491907 0.642123 0.063 Uiso 1 1 calc R U . . .
C2A C 0.704(2) 0.6681(12) 0.8261(4) 0.044(3) Uani 1 1 d . . . . .
H2AA H 0.761427 0.603014 0.813818 0.053 Uiso 1 1 calc R U . . .
H2AB H 0.616526 0.697209 0.801397 0.053 Uiso 1 1 calc R U . . .
C1A C 0.450(2) 0.5521(13) 0.8648(5) 0.056(4) Uani 1 1 d . . . . .
H1AA H 0.455795 0.487118 0.880632 0.068 Uiso 1 1 calc R U . . .
C3A C 0.717(2) 0.6233(12) 0.9155(5) 0.054(4) Uani 1 1 d . . . . .
H3AA H 0.793008 0.685819 0.924267 0.065 Uiso 1 1 calc R U . . .
H3AB H 0.638382 0.602042 0.943273 0.065 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
I1A C4A 2.140(13) . ?
I1 C4 2.131(14) . ?
O7 N3 1.394(15) . ?
O7 C3 1.461(15) . ?
O4 N2 1.399(13) . ?
O4 C2 1.471(16) . ?
O5 N2 1.215(15) . ?
O1A N1A 1.397(16) . ?
O1A C1A 1.438(16) . ?
O4A N2A 1.415(14) . ?
O4A C2A 1.433(15) . ?
O1 N1 1.420(18) . ?
O1 C1 1.466(17) . ?
O5A N2A 1.203(14) . ?
O6 N2 1.159(13) . ?
O9A N3A 1.172(15) . ?
O8A N3A 1.214(16) . ?
O2 N1 1.203(17) . ?
O6A N2A 1.187(15) . ?
O7A N3A 1.387(14) . ?
O7A C3A 1.449(16) . ?
O3 N1 1.181(17) . ?
O8 N3 1.201(16) . ?
O2A N1A 1.157(16) . ?
N3 O9 1.207(17) . ?
C5A C4A 1.554(19) . ?
C5A C2A 1.549(17) . ?
C5A C1A 1.53(2) . ?
C5A C3A 1.485(18) . ?
N1A O3A 1.226(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C5 1.533(18) . ?
C5 C1 1.541(19) . ?
C5 C3 1.526(16) . ?
C5 C4 1.523(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C1A H1AA 0.9300 . ?
C3A H3AA 0.9700 . ?
C3A H3AB 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
N3 O7 C3 113.5(10) . . ?
N2 O4 C2 112.5(9) . . ?
N1A O1A C1A 112.4(12) . . ?
N2A O4A C2A 112.1(9) . . ?
N1 O1 C1 113.8(11) . . ?
N3A O7A C3A 114.7(10) . . ?
O5A N2A O4A 117.8(12) . . ?
O6A N2A O4A 113.6(11) . . ?
O6A N2A O5A 128.5(13) . . ?
O5 N2 O4 109.9(10) . . ?
O6 N2 O4 119.8(12) . . ?
O6 N2 O5 130.3(12) . . ?
O9A N3A O8A 128.2(12) . . ?
O9A N3A O7A 118.0(13) . . ?
O8A N3A O7A 113.8(12) . . ?
O8 N3 O7 112.2(14) . . ?
O8 N3 O9 128.8(14) . . ?
O9 N3 O7 118.9(13) . . ?
C2A C5A C4A 106.5(11) . . ?
C1A C5A C4A 111.1(10) . . ?
C1A C5A C2A 108.2(11) . . ?
C3A C5A C4A 109.2(11) . . ?
C3A C5A C2A 113.0(11) . . ?
C3A C5A C1A 109.0(12) . . ?
O2A N1A O1A 120.1(13) . . ?
O2A N1A O3A 128.7(15) . . ?
O3A N1A O1A 111.2(15) . . ?
O4 C2 H2A 110.5 . . ?
O4 C2 H2B 110.5 . . ?
O4 C2 C5 106.3(10) . . ?
H2A C2 H2B 108.7 . . ?
C5 C2 H2A 110.5 . . ?
C5 C2 H2B 110.5 . . ?
C2 C5 C1 106.0(10) . . ?
C3 C5 C2 111.9(11) . . ?
C3 C5 C1 107.8(11) . . ?
C4 C5 C2 108.3(11) . . ?
C4 C5 C1 113.2(11) . . ?
C4 C5 C3 109.6(11) . . ?
O2 N1 O1 117.2(13) . . ?
O3 N1 O1 112.9(16) . . ?
O3 N1 O2 129.8(17) . . ?
O1 C1 C5 105.5(11) . . ?
O1 C1 H1A 110.6 . . ?
O1 C1 H1B 110.6 . . ?
C5 C1 H1A 110.6 . . ?
C5 C1 H1B 110.6 . . ?
H1A C1 H1B 108.8 . . ?
O7 C3 C5 106.9(10) . . ?
O7 C3 H3A 110.3 . . ?
O7 C3 H3B 110.3 . . ?
C5 C3 H3A 110.3 . . ?
C5 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
I1A C4A H4AA 108.4 . . ?
I1A C4A H4AB 108.4 . . ?
C5A C4A I1A 115.7(9) . . ?
C5A C4A H4AA 108.4 . . ?
C5A C4A H4AB 108.4 . . ?
H4AA C4A H4AB 107.4 . . ?
I1 C4 H4A 108.2 . . ?
I1 C4 H4B 108.2 . . ?
C5 C4 I1 116.2(9) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
O4A C2A C5A 106.5(9) . . ?
O4A C2A H2AA 110.4 . . ?
O4A C2A H2AB 110.4 . . ?
C5A C2A H2AA 110.4 . . ?
C5A C2A H2AB 110.4 . . ?
H2AA C2A H2AB 108.6 . . ?
O1A C1A C5A 107.8(12) . . ?
O1A C1A H1AA 126.1 . . ?
C5A C1A H1AA 126.1 . . ?
O7A C3A C5A 107.9(10) . . ?
O7A C3A H3AA 110.1 . . ?
O7A C3A H3AB 110.1 . . ?
C5A C3A H3AA 110.1 . . ?
C5A C3A H3AB 110.1 . . ?
H3AA C3A H3AB 108.4 . . ?

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
O4 C2 C5 C1 169.6(10) . . . . ?
O4 C2 C5 C3 52.3(14) . . . . ?
O4 C2 C5 C4 -68.6(13) . . . . ?
N2A O4A C2A C5A -174.9(10) . . . . ?
N2 O4 C2 C5 170.3(10) . . . . ?
N3A O7A C3A C5A -164.1(11) . . . . ?
N3 O7 C3 C5 165.6(10) . . . . ?
N1A O1A C1A C5A 162.8(10) . . . . ?
C2 O4 N2 O5 176.1(11) . . . . ?
C2 O4 N2 O6 -5.0(18) . . . . ?
C2 C5 C1 O1 66.4(13) . . . . ?
C2 C5 C3 O7 53.3(15) . . . . ?
C2 C5 C4 I1 -176.1(9) . . . . ?
N1 O1 C1 C5 -162.1(10) . . . . ?
C1 O1 N1 O2 0.2(17) . . . . ?
C1 O1 N1 O3 179.9(12) . . . . ?
C1 C5 C3 O7 -62.9(13) . . . . ?
C1 C5 C4 I1 -58.9(13) . . . . ?
C3 O7 N3 O8 175.2(11) . . . . ?
C3 O7 N3 O9 -1.5(17) . . . . ?
C3 C5 C1 O1 -173.6(10) . . . . ?
C3 C5 C4 I1 61.5(13) . . . . ?
C4A C5A C2A O4A 71.5(12) . . . . ?
C4A C5A C1A O1A 53.2(14) . . . . ?
C4A C5A C3A O7A -171.2(11) . . . . ?
C4 C5 C1 O1 -52.2(13) . . . . ?
C4 C5 C3 O7 173.4(10) . . . . ?
C2A O4A N2A O5A 1.8(16) . . . . ?
C2A O4A N2A O6A -176.1(11) . . . . ?
C2A C5A C4A I1A 178.8(8) . . . . ?
C2A C5A C1A O1A -63.3(13) . . . . ?
C2A C5A C3A O7A -53.0(16) . . . . ?
C1A O1A N1A O2A -3.6(17) . . . . ?
C1A O1A N1A O3A 177.7(11) . . . . ?
C1A C5A C4A I1A 61.2(12) . . . . ?
C1A C5A C2A O4A -169.0(10) . . . . ?
C1A C5A C3A O7A 67.3(14) . . . . ?
C3A O7A N3A O9A 4.2(19) . . . . ?
C3A O7A N3A O8A -173.8(12) . . . . ?
C3A C5A C4A I1A -59.0(12) . . . . ?
C3A C5A C2A O4A -48.2(15) . . . . ?
C3A C5A C1A O1A 173.5(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    Heat-sensitive,Energetic
####################################################################### 
# 
# 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_mo_petn_cl3_f_0m
_database_code_depnum_ccdc_archive 'CCDC 2252055'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-10-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H8 Cl3 N O3)'
_chemical_formula_sum            'C10 H16 Cl6 N2 O6'
_chemical_formula_weight         472.95
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.074(4)
_cell_length_b                   6.959(3)
_cell_length_c                   22.562(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.017(13)
_cell_angle_gamma                90
_cell_volume                     1895.7(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6548
_cell_measurement_temperature    250.00
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      3.375
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1125 before and 0.0799 after correction.
The Ratio of minimum to maximum transmission is 0.9232.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            48599
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         3.375
_diffrn_ambient_temperature      250.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4143
_reflns_number_total             4626
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.181
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+0.5789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4A(H4AA,H4AB), C2(H2A,H2B), C1(H1A,H1B), C3A(H3AA,H3AB), C3(H3A,
 H3B), C1A(H1AA,H1AB), C2A(H2AA,H2AB)
;
_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 0.36399(7) 0.97079(13) 0.50866(4) 0.0501(2) Uani 1 1 d . . . . .
Cl1A Cl 0.39914(7) 0.10439(13) 0.69448(4) 0.0527(2) Uani 1 1 d . . . . .
Cl3A Cl 0.61474(7) 0.75835(13) 0.61375(4) 0.0528(2) Uani 1 1 d . . . . .
Cl2A Cl 0.62955(7) 0.45225(15) 0.75958(4) 0.0536(2) Uani 1 1 d . . . . .
Cl1 Cl 0.59851(7) 0.65111(13) 0.44554(5) 0.0556(2) Uani 1 1 d . . . . .
Cl3 Cl 0.38021(7) 1.29222(13) 0.35722(4) 0.0514(2) Uani 1 1 d . . . . .
O1 O 0.60347(17) 1.0141(3) 0.32004(9) 0.0400(5) Uani 1 1 d . . . . .
O1A O 0.39265(17) 0.4556(3) 0.56986(9) 0.0377(5) Uani 1 1 d . . . . .
O3 O 0.76647(17) 1.1651(3) 0.32056(10) 0.0426(5) Uani 1 1 d . . . . .
O2A O 0.23386(19) 0.6210(3) 0.56565(12) 0.0463(5) Uani 1 1 d . . . . .
N1 N 0.7002(2) 1.0758(4) 0.29218(12) 0.0370(6) Uani 1 1 d . . . . .
O3A O 0.3009(2) 0.4781(4) 0.48788(12) 0.0565(7) Uani 1 1 d . . . . .
C5 C 0.4904(2) 0.9804(4) 0.40597(12) 0.0304(6) Uani 1 1 d . . . . .
N1A N 0.3008(2) 0.5253(4) 0.53907(13) 0.0389(6) Uani 1 1 d . . . . .
C4 C 0.5984(2) 1.0658(4) 0.38225(13) 0.0347(6) Uani 1 1 d . . . . .
H4A H 0.598555 1.205808 0.386912 0.042 Uiso 1 1 calc R U . . .
H4B H 0.662090 1.012745 0.403651 0.042 Uiso 1 1 calc R U . . .
O2 O 0.7048(2) 1.0282(4) 0.24116(11) 0.0593(7) Uani 1 1 d . . . . .
C4A C 0.3960(2) 0.5159(5) 0.63140(13) 0.0345(6) Uani 1 1 d . . . . .
H4AA H 0.332790 0.463103 0.653223 0.041 Uiso 1 1 calc R U . . .
H4AB H 0.393916 0.656374 0.634261 0.041 Uiso 1 1 calc R U . . .
C5A C 0.5046(2) 0.4383(4) 0.65639(13) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.4825(3) 1.0580(5) 0.46932(14) 0.0380(7) Uani 1 1 d . . . . .
H2A H 0.479394 1.198666 0.467917 0.046 Uiso 1 1 calc R U . . .
H2B H 0.549524 1.021682 0.491072 0.046 Uiso 1 1 calc R U . . .
C1 C 0.4910(2) 0.7593(4) 0.40279(13) 0.0355(7) Uani 1 1 d . . . . .
H1A H 0.499368 0.720062 0.361315 0.043 Uiso 1 1 calc R U . . .
H1B H 0.419356 0.711050 0.416797 0.043 Uiso 1 1 calc R U . . .
C3A C 0.6050(3) 0.5034(4) 0.61994(14) 0.0357(6) Uani 1 1 d . . . . .
H3AA H 0.599947 0.447679 0.580134 0.043 Uiso 1 1 calc R U . . .
H3AB H 0.672631 0.454194 0.638536 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3902(2) 1.0389(4) 0.36798(13) 0.0349(6) Uani 1 1 d . . . . .
H3A H 0.322360 0.993038 0.387161 0.042 Uiso 1 1 calc R U . . .
H3B H 0.395711 0.975895 0.329239 0.042 Uiso 1 1 calc R U . . .
C1A C 0.5095(2) 0.2173(4) 0.65473(15) 0.0364(7) Uani 1 1 d . . . . .
H1AA H 0.580222 0.175008 0.671562 0.044 Uiso 1 1 calc R U . . .
H1AB H 0.507050 0.174761 0.613344 0.044 Uiso 1 1 calc R U . . .
C2A C 0.5075(3) 0.5178(5) 0.72011(14) 0.0404(7) Uani 1 1 d . . . . .
H2AA H 0.442748 0.470003 0.741731 0.048 Uiso 1 1 calc R U . . .
H2AB H 0.502411 0.658225 0.718621 0.048 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 C2 1.790(3) . ?
Cl1A C1A 1.788(3) . ?
Cl3A C3A 1.784(3) . ?
Cl2A C2A 1.781(3) . ?
Cl1 C1 1.784(3) . ?
Cl3 C3 1.784(3) . ?
O1 N1 1.394(3) . ?
O1 C4 1.450(4) . ?
O1A N1A 1.395(3) . ?
O1A C4A 1.451(3) . ?
O3 N1 1.198(3) . ?
O2A N1A 1.207(4) . ?
N1 O2 1.199(3) . ?
O3A N1A 1.201(4) . ?
C5 C4 1.530(4) . ?
C5 C2 1.531(4) . ?
C5 C1 1.540(4) . ?
C5 C3 1.537(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A C5A 1.526(4) . ?
C5A C3A 1.533(4) . ?
C5A C1A 1.539(4) . ?
C5A C2A 1.541(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 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
N1 O1 C4 113.3(2) . . ?
N1A O1A C4A 113.4(2) . . ?
O3 N1 O1 118.5(2) . . ?
O3 N1 O2 128.7(3) . . ?
O2 N1 O1 112.7(2) . . ?
C4 C5 C2 104.1(2) . . ?
C4 C5 C1 111.6(2) . . ?
C4 C5 C3 111.9(2) . . ?
C2 C5 C1 113.3(2) . . ?
C2 C5 C3 112.2(2) . . ?
C3 C5 C1 104.0(2) . . ?
O2A N1A O1A 118.5(3) . . ?
O3A N1A O1A 112.5(3) . . ?
O3A N1A O2A 129.0(3) . . ?
O1 C4 C5 106.2(2) . . ?
O1 C4 H4A 110.5 . . ?
O1 C4 H4B 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
O1A C4A H4AA 110.5 . . ?
O1A C4A H4AB 110.5 . . ?
O1A C4A C5A 106.0(2) . . ?
H4AA C4A H4AB 108.7 . . ?
C5A C4A H4AA 110.5 . . ?
C5A C4A H4AB 110.5 . . ?
C4A C5A C3A 112.1(2) . . ?
C4A C5A C1A 112.2(2) . . ?
C4A C5A C2A 103.7(2) . . ?
C3A C5A C1A 104.6(2) . . ?
C3A C5A C2A 112.1(3) . . ?
C1A C5A C2A 112.4(3) . . ?
Cl2 C2 H2A 108.9 . . ?
Cl2 C2 H2B 108.9 . . ?
C5 C2 Cl2 113.2(2) . . ?
C5 C2 H2A 108.9 . . ?
C5 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
Cl1 C1 H1A 108.9 . . ?
Cl1 C1 H1B 108.9 . . ?
C5 C1 Cl1 113.5(2) . . ?
C5 C1 H1A 108.9 . . ?
C5 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
Cl3A C3A H3AA 109.0 . . ?
Cl3A C3A H3AB 109.0 . . ?
C5A C3A Cl3A 112.8(2) . . ?
C5A C3A H3AA 109.0 . . ?
C5A C3A H3AB 109.0 . . ?
H3AA C3A H3AB 107.8 . . ?
Cl3 C3 H3A 109.0 . . ?
Cl3 C3 H3B 109.0 . . ?
C5 C3 Cl3 113.0(2) . . ?
C5 C3 H3A 109.0 . . ?
C5 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
Cl1A C1A H1AA 108.9 . . ?
Cl1A C1A H1AB 108.9 . . ?
C5A C1A Cl1A 113.5(2) . . ?
C5A C1A H1AA 108.9 . . ?
C5A C1A H1AB 108.9 . . ?
H1AA C1A H1AB 107.7 . . ?
Cl2A C2A H2AA 108.9 . . ?
Cl2A C2A H2AB 108.9 . . ?
C5A C2A Cl2A 113.2(2) . . ?
C5A C2A H2AA 108.9 . . ?
C5A C2A H2AB 108.9 . . ?
H2AA C2A H2AB 107.8 . . ?

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
O1A C4A C5A C3A 55.1(3) . . . . ?
O1A C4A C5A C1A -62.2(3) . . . . ?
O1A C4A C5A C2A 176.3(2) . . . . ?
N1 O1 C4 C5 -177.7(2) . . . . ?
N1A O1A C4A C5A -176.3(2) . . . . ?
C4 O1 N1 O3 -1.4(4) . . . . ?
C4 O1 N1 O2 178.3(3) . . . . ?
C4 C5 C2 Cl2 -177.7(2) . . . . ?
C4 C5 C1 Cl1 60.9(3) . . . . ?
C4 C5 C3 Cl3 -52.5(3) . . . . ?
C4A O1A N1A O2A -1.9(4) . . . . ?
C4A O1A N1A O3A 178.2(3) . . . . ?
C4A C5A C3A Cl3A 56.6(3) . . . . ?
C4A C5A C1A Cl1A -58.0(3) . . . . ?
C4A C5A C2A Cl2A -178.6(2) . . . . ?
C2 C5 C4 O1 -173.7(2) . . . . ?
C2 C5 C1 Cl1 -56.2(3) . . . . ?
C2 C5 C3 Cl3 64.0(3) . . . . ?
C1 C5 C4 O1 63.7(3) . . . . ?
C1 C5 C2 Cl2 -56.3(3) . . . . ?
C1 C5 C3 Cl3 -173.1(2) . . . . ?
C3A C5A C1A Cl1A -179.8(2) . . . . ?
C3A C5A C2A Cl2A -57.5(3) . . . . ?
C3 C5 C4 O1 -52.3(3) . . . . ?
C3 C5 C2 Cl2 61.1(3) . . . . ?
C3 C5 C1 Cl1 -178.3(2) . . . . ?
C1A C5A C3A Cl3A 178.4(2) . . . . ?
C1A C5A C2A Cl2A 60.0(3) . . . . ?
C2A C5A C3A Cl3A -59.6(3) . . . . ?
C2A C5A C1A Cl1A 58.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_mo_petn_br3_c_0m
_database_code_depnum_ccdc_archive 'CCDC 2252058'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H8 Br3 N O3'
_chemical_formula_sum            'C5 H8 Br3 N O3'
_chemical_formula_weight         369.85
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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                   7.0321(3)
_cell_length_b                   11.3862(5)
_cell_length_c                   7.2912(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.747(2)
_cell_angle_gamma                90
_cell_volume                     511.85(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.187
_shelx_estimated_absorpt_T_max   0.590
_shelx_estimated_absorpt_T_min   0.590
_exptl_absorpt_coefficient_mu    11.792
_exptl_absorpt_correction_T_max  0.748
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.105 before and 0.0658 after correction.
The Ratio of minimum to maximum transmission is 0.7829.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.053
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17964
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.505
_diffrn_reflns_theta_min         3.187
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2125
_reflns_number_total             3376
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         -0.395
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         3376
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0672
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C1(H1A,H1B), C2(H2A,H2B)
;
_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
Br1 Br 0.29687(11) 0.63868(6) 0.28233(9) 0.05653(19) Uani 1 1 d . . . . .
Br2 Br 0.78045(11) 0.77123(4) 0.85138(10) 0.0596(2) Uani 1 1 d . . . . .
Br3 Br 0.73303(11) 0.46337(6) 1.14301(11) 0.0613(2) Uani 1 1 d . . . . .
O1 O 0.2939(6) 0.3875(3) 0.6399(7) 0.0477(10) Uani 1 1 d . . . . .
O2 O -0.0322(7) 0.3888(4) 0.6218(7) 0.0545(11) Uani 1 1 d . . . . .
O3 O 0.0979(8) 0.2301(4) 0.5595(9) 0.0704(14) Uani 1 1 d . . . . .
C5 C 0.5163(9) 0.5581(4) 0.7194(9) 0.0350(10) Uani 1 1 d . . . . .
N1 N 0.1037(8) 0.3317(4) 0.6047(7) 0.0466(11) Uani 1 1 d . . . . .
C3 C 0.7102(9) 0.4848(5) 0.8687(9) 0.0415(13) Uani 1 1 d . . . . .
H3A H 0.841636 0.522298 0.885708 0.050 Uiso 1 1 calc R U . . .
H3B H 0.700612 0.408261 0.806401 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2994(9) 0.5101(4) 0.6932(9) 0.0398(12) Uani 1 1 d . . . . .
H4A H 0.292499 0.518724 0.822234 0.048 Uiso 1 1 calc R U . . .
H4B H 0.178073 0.551838 0.582816 0.048 Uiso 1 1 calc R U . . .
C1 C 0.5279(9) 0.5529(5) 0.5136(9) 0.0419(12) Uani 1 1 d . . . . .
H1A H 0.522294 0.471327 0.472955 0.050 Uiso 1 1 calc R U . . .
H1B H 0.666468 0.584526 0.538709 0.050 Uiso 1 1 calc R U . . .
C2 C 0.5228(10) 0.6827(4) 0.7974(9) 0.0456(14) Uani 1 1 d . . . . .
H2A H 0.512712 0.679183 0.925331 0.055 Uiso 1 1 calc R U . . .
H2B H 0.396429 0.724669 0.694295 0.055 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
Br1 C1 1.950(5) . ?
Br2 C2 1.941(6) . ?
Br3 C3 1.944(6) . ?
O1 N1 1.389(6) . ?
O1 C4 1.444(6) . ?
O2 N1 1.211(6) . ?
O3 N1 1.198(6) . ?
C5 C3 1.521(7) . ?
C5 C4 1.544(8) . ?
C5 C1 1.542(8) . ?
C5 C2 1.520(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 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
N1 O1 C4 113.0(4) . . ?
C3 C5 C4 112.8(5) . . ?
C3 C5 C1 103.1(4) . . ?
C1 C5 C4 112.2(4) . . ?
C2 C5 C3 112.9(4) . . ?
C2 C5 C4 103.1(4) . . ?
C2 C5 C1 113.2(5) . . ?
O2 N1 O1 118.2(5) . . ?
O3 N1 O1 113.3(5) . . ?
O3 N1 O2 128.5(5) . . ?
Br3 C3 H3A 108.7 . . ?
Br3 C3 H3B 108.7 . . ?
C5 C3 Br3 114.0(4) . . ?
C5 C3 H3A 108.7 . . ?
C5 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O1 C4 C5 105.8(4) . . ?
O1 C4 H4A 110.6 . . ?
O1 C4 H4B 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
Br1 C1 H1A 108.7 . . ?
Br1 C1 H1B 108.7 . . ?
C5 C1 Br1 114.2(4) . . ?
C5 C1 H1A 108.7 . . ?
C5 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
Br2 C2 H2A 108.6 . . ?
Br2 C2 H2B 108.6 . . ?
C5 C2 Br2 114.7(4) . . ?
C5 C2 H2A 108.6 . . ?
C5 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?

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 O1 C4 C5 -178.2(4) . . . . ?
C3 C5 C4 O1 -52.1(6) . . . . ?
C3 C5 C1 Br1 179.6(4) . . . . ?
C3 C5 C2 Br2 57.4(6) . . . . ?
C4 O1 N1 O2 -0.1(7) . . . . ?
C4 O1 N1 O3 179.7(5) . . . . ?
C4 C5 C3 Br3 -54.6(5) . . . . ?
C4 C5 C1 Br1 58.0(5) . . . . ?
C4 C5 C2 Br2 179.4(4) . . . . ?
C1 C5 C3 Br3 -175.8(3) . . . . ?
C1 C5 C4 O1 63.7(5) . . . . ?
C1 C5 C2 Br2 -59.2(5) . . . . ?
C2 C5 C3 Br3 61.7(6) . . . . ?
C2 C5 C4 O1 -174.2(4) . . . . ?
C2 C5 C1 Br1 -58.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_cu_petn_cl1_a_0m
_database_code_depnum_ccdc_archive 'CCDC 2252056'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H8 Cl N3 O9)'
_chemical_formula_sum            'C10 H16 Cl2 N6 O18'
_chemical_formula_weight         579.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.5956(11)
_cell_length_b                   6.6449(6)
_cell_length_c                   27.335(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.653(5)
_cell_angle_gamma                90
_cell_volume                     2232.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      74.20
_cell_measurement_theta_min      3.314
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    3.566
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1242 before and 0.0754 after correction.
The Ratio of minimum to maximum transmission is 0.8451.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            33897
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.551
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4005
_reflns_number_total             4529
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.811
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.094
_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)+(0.1068P)²+4.9920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2314
_refine_ls_wR_factor_ref         0.2351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C1(H1A,H1B), C2A(H2AA,H2AB), C3(H3A,H3B), C1A(H1AA,H1AB),
 C2(H2A,H2B), C4A(H4AA,H4AB), C4(H4A,H4B)
;
_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 0.51155(13) 0.5559(2) 0.30492(5) 0.0774(5) Uani 1 1 d . . . . .
Cl1A Cl 0.78888(14) 0.0841(3) 0.30324(6) 0.0873(6) Uani 1 1 d . . . . .
O7A O 0.8422(2) 0.6217(4) 0.40983(9) 0.0406(6) Uani 1 1 d . . . . .
O1 O 0.5742(2) 1.1117(4) 0.40924(10) 0.0431(6) Uani 1 1 d . . . . .
O1A O 1.0033(2) 0.0668(5) 0.41388(12) 0.0512(7) Uani 1 1 d . . . . .
O7 O 0.4139(2) 0.5598(5) 0.41666(12) 0.0504(7) Uani 1 1 d . . . . .
O4 O 0.3378(3) 1.1099(5) 0.34247(11) 0.0516(8) Uani 1 1 d . . . . .
O8A O 0.8838(3) 0.6694(5) 0.49237(10) 0.0552(8) Uani 1 1 d . . . . .
O4A O 1.0159(2) 0.6133(5) 0.34086(10) 0.0502(7) Uani 1 1 d . . . . .
O9A O 0.7680(3) 0.8609(5) 0.44442(13) 0.0606(9) Uani 1 1 d . . . . .
O2 O 0.6109(3) 1.1621(5) 0.49177(11) 0.0579(8) Uani 1 1 d . . . . .
O3 O 0.6790(3) 1.3559(5) 0.44313(13) 0.0609(9) Uani 1 1 d . . . . .
N3A N 0.8311(3) 0.7252(5) 0.45306(12) 0.0413(7) Uani 1 1 d . . . . .
N1 N 0.6254(3) 1.2193(5) 0.45225(13) 0.0434(8) Uani 1 1 d . . . . .
O8 O 0.3774(3) 0.3444(6) 0.47024(15) 0.0753(11) Uani 1 1 d . . . . .
O5 O 0.2115(3) 1.3308(6) 0.31701(15) 0.0711(10) Uani 1 1 d . . . . .
O9 O 0.2442(3) 0.5176(6) 0.42688(14) 0.0647(9) Uani 1 1 d . . . . .
O6A O 1.1243(3) 0.8165(6) 0.31359(15) 0.0738(11) Uani 1 1 d . . . . .
O2A O 1.0911(3) -0.1468(6) 0.46745(15) 0.0719(10) Uani 1 1 d . . . . .
O3A O 1.1827(3) 0.0214(6) 0.42356(16) 0.0694(10) Uani 1 1 d . . . . .
N3 N 0.3365(3) 0.4671(5) 0.43926(14) 0.0510(9) Uani 1 1 d . . . . .
N1A N 1.1028(3) -0.0288(5) 0.43676(14) 0.0502(9) Uani 1 1 d . . . . .
N2A N 1.0442(3) 0.7150(6) 0.30114(14) 0.0511(9) Uani 1 1 d . . . . .
O5A O 0.9878(4) 0.6927(8) 0.26019(13) 0.0859(14) Uani 1 1 d . . . . .
C5 C 0.4610(3) 0.8391(6) 0.37077(14) 0.0402(8) Uani 1 1 d . . . . .
O6 O 0.2872(4) 1.1893(7) 0.26197(14) 0.0820(12) Uani 1 1 d . . . . .
N2 N 0.2732(3) 1.2173(6) 0.30322(14) 0.0537(9) Uani 1 1 d . . . . .
C5A C 0.9152(3) 0.3510(6) 0.36978(13) 0.0382(8) Uani 1 1 d . . . . .
C3A C 0.9226(3) 0.4629(6) 0.41946(13) 0.0379(8) Uani 1 1 d . . . . .
H3AA H 0.907772 0.371828 0.444884 0.046 Uiso 1 1 calc R U . . .
H3AB H 0.994830 0.519047 0.431112 0.046 Uiso 1 1 calc R U . . .
C1 C 0.5035(3) 0.9544(6) 0.41963(14) 0.0405(8) Uani 1 1 d . . . . .
H1A H 0.443275 1.011952 0.431749 0.049 Uiso 1 1 calc R U . . .
H1B H 0.543231 0.864437 0.445119 0.049 Uiso 1 1 calc R U . . .
C2A C 0.9172(3) 0.4959(7) 0.32624(14) 0.0441(9) Uani 1 1 d . . . . .
H2AA H 0.917408 0.421270 0.295754 0.053 Uiso 1 1 calc R U . . .
H2AB H 0.853869 0.582918 0.320375 0.053 Uiso 1 1 calc R U . . .
C3 C 0.3668(3) 0.7079(7) 0.37891(16) 0.0457(9) Uani 1 1 d . . . . .
H3A H 0.313063 0.788969 0.390469 0.055 Uiso 1 1 calc R U . . .
H3B H 0.331780 0.641836 0.347927 0.055 Uiso 1 1 calc R U . . .
C1A C 1.0137(4) 0.2129(7) 0.37617(17) 0.0490(10) Uani 1 1 d . . . . .
H1AA H 1.015334 0.146227 0.344765 0.059 Uiso 1 1 calc R U . . .
H1AB H 1.080375 0.289450 0.386747 0.059 Uiso 1 1 calc R U . . .
C2 C 0.4160(3) 0.9789(7) 0.32669(15) 0.0470(9) Uani 1 1 d . . . . .
H2A H 0.474201 1.057505 0.318126 0.056 Uiso 1 1 calc R U . . .
H2B H 0.380999 0.901388 0.297533 0.056 Uiso 1 1 calc R U . . .
C4A C 0.8062(3) 0.2378(7) 0.35805(17) 0.0498(10) Uani 1 1 d . . . . .
H4AA H 0.747354 0.334882 0.353561 0.060 Uiso 1 1 calc R U . . .
H4AB H 0.801452 0.153658 0.386475 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5545(3) 0.7169(7) 0.35826(17) 0.0498(10) Uani 1 1 d . . . . .
H4A H 0.587238 0.635423 0.387073 0.060 Uiso 1 1 calc R U . . .
H4B H 0.609711 0.808584 0.351736 0.060 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 C4 1.794(5) . ?
Cl1A C4A 1.787(5) . ?
O7A N3A 1.401(4) . ?
O7A C3A 1.446(4) . ?
O1 N1 1.406(4) . ?
O1 C1 1.441(5) . ?
O1A N1A 1.422(5) . ?
O1A C1A 1.443(5) . ?
O7 N3 1.405(5) . ?
O7 C3 1.455(5) . ?
O4 N2 1.393(5) . ?
O4 C2 1.449(5) . ?
O8A N3A 1.192(4) . ?
O4A N2A 1.390(4) . ?
O4A C2A 1.448(5) . ?
O9A N3A 1.191(4) . ?
O2 N1 1.196(4) . ?
O3 N1 1.190(5) . ?
O8 N3 1.206(5) . ?
O5 N2 1.201(5) . ?
O9 N3 1.186(5) . ?
O6A N2A 1.199(5) . ?
O2A N1A 1.181(5) . ?
O3A N1A 1.189(5) . ?
N2A O5A 1.197(5) . ?
C5 C1 1.531(5) . ?
C5 C3 1.527(5) . ?
C5 C2 1.529(5) . ?
C5 C4 1.530(6) . ?
O6 N2 1.194(5) . ?
C5A C3A 1.533(5) . ?
C5A C2A 1.535(5) . ?
C5A C1A 1.523(5) . ?
C5A C4A 1.536(5) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 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
N3A O7A C3A 113.6(3) . . ?
N1 O1 C1 113.2(3) . . ?
N1A O1A C1A 113.9(3) . . ?
N3 O7 C3 113.2(3) . . ?
N2 O4 C2 113.5(3) . . ?
N2A O4A C2A 113.5(3) . . ?
O8A N3A O7A 118.0(3) . . ?
O9A N3A O7A 113.0(3) . . ?
O9A N3A O8A 129.0(4) . . ?
O2 N1 O1 117.4(3) . . ?
O3 N1 O1 113.0(3) . . ?
O3 N1 O2 129.6(4) . . ?
O8 N3 O7 112.0(4) . . ?
O9 N3 O7 118.7(4) . . ?
O9 N3 O8 129.2(4) . . ?
O2A N1A O1A 112.0(4) . . ?
O2A N1A O3A 130.4(4) . . ?
O3A N1A O1A 117.6(4) . . ?
O6A N2A O4A 113.3(4) . . ?
O5A N2A O4A 117.9(4) . . ?
O5A N2A O6A 128.7(4) . . ?
C3 C5 C1 107.0(3) . . ?
C3 C5 C2 107.2(3) . . ?
C3 C5 C4 113.0(4) . . ?
C2 C5 C1 112.4(3) . . ?
C2 C5 C4 108.5(3) . . ?
C4 C5 C1 108.7(3) . . ?
O5 N2 O4 112.9(4) . . ?
O6 N2 O4 117.7(4) . . ?
O6 N2 O5 129.4(4) . . ?
C3A C5A C2A 112.0(3) . . ?
C3A C5A C4A 107.5(3) . . ?
C2A C5A C4A 108.1(3) . . ?
C1A C5A C3A 107.5(3) . . ?
C1A C5A C2A 108.4(3) . . ?
C1A C5A C4A 113.4(4) . . ?
O7A C3A C5A 106.7(3) . . ?
O7A C3A H3AA 110.4 . . ?
O7A C3A H3AB 110.4 . . ?
C5A C3A H3AA 110.4 . . ?
C5A C3A H3AB 110.4 . . ?
H3AA C3A H3AB 108.6 . . ?
O1 C1 C5 107.7(3) . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
C5 C1 H1A 110.2 . . ?
C5 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
O4A C2A C5A 106.4(3) . . ?
O4A C2A H2AA 110.4 . . ?
O4A C2A H2AB 110.4 . . ?
C5A C2A H2AA 110.4 . . ?
C5A C2A H2AB 110.4 . . ?
H2AA C2A H2AB 108.6 . . ?
O7 C3 C5 106.3(3) . . ?
O7 C3 H3A 110.5 . . ?
O7 C3 H3B 110.5 . . ?
C5 C3 H3A 110.5 . . ?
C5 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
O1A C1A C5A 106.7(3) . . ?
O1A C1A H1AA 110.4 . . ?
O1A C1A H1AB 110.4 . . ?
C5A C1A H1AA 110.4 . . ?
C5A C1A H1AB 110.4 . . ?
H1AA C1A H1AB 108.6 . . ?
O4 C2 C5 106.8(3) . . ?
O4 C2 H2A 110.4 . . ?
O4 C2 H2B 110.4 . . ?
C5 C2 H2A 110.4 . . ?
C5 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
Cl1A C4A H4AA 108.9 . . ?
Cl1A C4A H4AB 108.9 . . ?
C5A C4A Cl1A 113.2(3) . . ?
C5A C4A H4AA 108.9 . . ?
C5A C4A H4AB 108.9 . . ?
H4AA C4A H4AB 107.7 . . ?
Cl1 C4 H4A 109.0 . . ?
Cl1 C4 H4B 109.0 . . ?
C5 C4 Cl1 112.8(3) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?

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
N3A O7A C3A C5A 173.7(3) . . . . ?
N1 O1 C1 C5 -175.3(3) . . . . ?
N3 O7 C3 C5 162.1(3) . . . . ?
N1A O1A C1A C5A -159.6(3) . . . . ?
N2A O4A C2A C5A 164.6(3) . . . . ?
N2 O4 C2 C5 -167.3(3) . . . . ?
C3A O7A N3A O8A -2.8(5) . . . . ?
C3A O7A N3A O9A 177.0(3) . . . . ?
C3A C5A C2A O4A 56.2(4) . . . . ?
C3A C5A C1A O1A 64.3(4) . . . . ?
C3A C5A C4A Cl1A -175.8(3) . . . . ?
C1 O1 N1 O2 4.7(5) . . . . ?
C1 O1 N1 O3 -176.1(3) . . . . ?
C1 C5 C3 O7 -66.1(4) . . . . ?
C1 C5 C2 O4 -52.4(4) . . . . ?
C1 C5 C4 Cl1 174.3(3) . . . . ?
C2A O4A N2A O6A 178.1(4) . . . . ?
C2A O4A N2A O5A -1.5(6) . . . . ?
C2A C5A C3A O7A 49.5(4) . . . . ?
C2A C5A C1A O1A -174.4(3) . . . . ?
C2A C5A C4A Cl1A 63.1(4) . . . . ?
C3 O7 N3 O8 179.7(4) . . . . ?
C3 O7 N3 O9 -1.3(5) . . . . ?
C3 C5 C1 O1 -166.8(3) . . . . ?
C3 C5 C2 O4 65.0(4) . . . . ?
C3 C5 C4 Cl1 55.6(4) . . . . ?
C1A O1A N1A O2A 179.8(4) . . . . ?
C1A O1A N1A O3A 1.1(5) . . . . ?
C1A C5A C3A O7A 168.5(3) . . . . ?
C1A C5A C2A O4A -62.2(4) . . . . ?
C1A C5A C4A Cl1A -57.1(4) . . . . ?
C2 O4 N2 O5 -177.4(4) . . . . ?
C2 O4 N2 O6 1.1(6) . . . . ?
C2 C5 C1 O1 -49.3(4) . . . . ?
C2 C5 C3 O7 173.1(3) . . . . ?
C2 C5 C4 Cl1 -63.1(4) . . . . ?
C4A C5A C3A O7A -69.1(4) . . . . ?
C4A C5A C2A O4A 174.5(3) . . . . ?
C4A C5A C1A O1A -54.4(4) . . . . ?
C4 C5 C1 O1 70.8(4) . . . . ?
C4 C5 C3 O7 53.6(4) . . . . ?
C4 C5 C2 O4 -172.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    Heat-sensitive,Energetic
####################################################################### 
# 
# 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_cu_petn_ethyl_b_0m
_database_code_depnum_ccdc_archive 'CCDC 2252057'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H11 N3 O9'
_chemical_formula_sum            'C6 H11 N3 O9'
_chemical_formula_weight         269.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.5161(2)
_cell_length_b                   11.0417(3)
_cell_length_c                   14.1414(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.476(2)
_cell_angle_gamma                90
_cell_volume                     1172.51(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6463
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      73.55
_cell_measurement_theta_min      6.265
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1098 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.8248.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28483
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         6.265
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1603
_reflns_number_total             2102
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.235
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.026
_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)+(0.0582P)²+0.4030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1297
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C1(H1A,H1B), C5(H5A,H5B)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
O7 O 0.13513(18) 0.25104(11) 0.53580(9) 0.0536(4) Uani 1 1 d . . . . .
O4 O 0.37659(18) 0.42950(13) 0.37949(11) 0.0647(5) Uani 1 1 d . . . . .
O1 O 0.1802(2) 0.30333(14) 0.20363(9) 0.0646(5) Uani 1 1 d . . . . .
O8 O 0.1348(2) 0.24106(16) 0.68835(10) 0.0756(5) Uani 1 1 d . . . . .
O9 O -0.0138(2) 0.38536(15) 0.61874(11) 0.0747(5) Uani 1 1 d . . . . .
N3 N 0.0794(2) 0.29808(16) 0.62109(11) 0.0550(5) Uani 1 1 d . . . . .
O6 O 0.5553(3) 0.5833(2) 0.39211(15) 0.0981(7) Uani 1 1 d . . . . .
O2 O 0.2029(3) 0.3245(2) 0.05253(12) 0.1027(7) Uani 1 1 d . . . . .
O5 O 0.6665(2) 0.4025(2) 0.38413(17) 0.1062(7) Uani 1 1 d . . . . .
O3 O -0.0179(3) 0.4081(2) 0.11829(12) 0.0983(7) Uani 1 1 d . . . . .
N2 N 0.5488(3) 0.4744(2) 0.38595(13) 0.0701(6) Uani 1 1 d . . . . .
C6 C 0.1644(2) 0.26842(16) 0.36882(12) 0.0476(5) Uani 1 1 d . . . . .
N1 N 0.1137(3) 0.34982(19) 0.11780(13) 0.0691(5) Uani 1 1 d . . . . .
C2 C 0.3632(3) 0.29842(19) 0.37849(14) 0.0552(5) Uani 1 1 d . . . . .
H2A H 0.415204 0.264726 0.436688 0.066 Uiso 1 1 calc R U . . .
H2B H 0.425178 0.265212 0.325616 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0685(3) 0.31796(17) 0.45402(12) 0.0496(5) Uani 1 1 d . . . . .
H3A H 0.092848 0.403695 0.462081 0.060 Uiso 1 1 calc R U . . .
H3B H -0.059173 0.306923 0.444995 0.060 Uiso 1 1 calc R U . . .
C1 C 0.0756(3) 0.33302(19) 0.28359(13) 0.0514(5) Uani 1 1 d . . . . .
H1A H -0.046103 0.305310 0.273073 0.062 Uiso 1 1 calc R U . . .
H1B H 0.074453 0.419880 0.293812 0.062 Uiso 1 1 calc R U . . .
C5 C 0.1491(3) 0.12940(19) 0.35999(16) 0.0657(6) Uani 1 1 d . . . . .
H5A H 0.201134 0.105010 0.301359 0.079 Uiso 1 1 calc R U . . .
H5B H 0.219872 0.093079 0.411507 0.079 Uiso 1 1 calc R U . . .
C4 C -0.0363(4) 0.0782(2) 0.3613(2) 0.0898(9) Uani 1 1 d . . . . .
H4A H -0.110216 0.116582 0.312964 0.135 Uiso 1 1 calc R U . . .
H4B H -0.084556 0.092823 0.421994 0.135 Uiso 1 1 calc R U . . .
H4C H -0.032553 -0.007384 0.349670 0.135 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
O7 N3 1.394(2) . ?
O7 C3 1.444(2) . ?
O4 N2 1.386(2) . ?
O4 C2 1.451(3) . ?
O1 N1 1.391(2) . ?
O1 C1 1.442(2) . ?
O8 N3 1.200(2) . ?
O9 N3 1.191(2) . ?
O6 N2 1.206(3) . ?
O2 N1 1.197(3) . ?
O5 N2 1.190(3) . ?
O3 N1 1.180(3) . ?
C6 C2 1.531(3) . ?
C6 C3 1.531(2) . ?
C6 C1 1.529(3) . ?
C6 C5 1.544(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.505(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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 O7 C3 113.30(14) . . ?
N2 O4 C2 114.98(17) . . ?
N1 O1 C1 114.40(16) . . ?
O8 N3 O7 112.54(17) . . ?
O9 N3 O7 118.40(16) . . ?
O9 N3 O8 129.06(18) . . ?
O6 N2 O4 113.4(2) . . ?
O5 N2 O4 116.9(2) . . ?
O5 N2 O6 129.7(2) . . ?
C2 C6 C3 110.07(15) . . ?
C2 C6 C5 106.93(17) . . ?
C3 C6 C5 112.51(16) . . ?
C1 C6 C2 111.13(16) . . ?
C1 C6 C3 104.44(14) . . ?
C1 C6 C5 111.82(16) . . ?
O2 N1 O1 113.3(2) . . ?
O3 N1 O1 117.75(19) . . ?
O3 N1 O2 129.0(2) . . ?
O4 C2 C6 106.50(15) . . ?
O4 C2 H2A 110.4 . . ?
O4 C2 H2B 110.4 . . ?
C6 C2 H2A 110.4 . . ?
C6 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O7 C3 C6 106.77(14) . . ?
O7 C3 H3A 110.4 . . ?
O7 C3 H3B 110.4 . . ?
C6 C3 H3A 110.4 . . ?
C6 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O1 C1 C6 106.14(15) . . ?
O1 C1 H1A 110.5 . . ?
O1 C1 H1B 110.5 . . ?
C6 C1 H1A 110.5 . . ?
C6 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C4 C5 C6 116.0(2) . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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 O7 C3 C6 171.08(14) . . . . ?
N2 O4 C2 C6 -178.73(16) . . . . ?
N1 O1 C1 C6 176.98(15) . . . . ?
C2 O4 N2 O6 -175.97(18) . . . . ?
C2 O4 N2 O5 4.5(3) . . . . ?
C2 C6 C3 O7 -66.17(19) . . . . ?
C2 C6 C1 O1 52.6(2) . . . . ?
C2 C6 C5 C4 173.0(2) . . . . ?
C3 O7 N3 O8 179.52(16) . . . . ?
C3 O7 N3 O9 0.0(2) . . . . ?
C3 C6 C2 O4 -61.73(19) . . . . ?
C3 C6 C1 O1 171.29(15) . . . . ?
C3 C6 C5 C4 52.0(3) . . . . ?
C1 O1 N1 O2 179.73(19) . . . . ?
C1 O1 N1 O3 0.3(3) . . . . ?
C1 C6 C2 O4 53.47(19) . . . . ?
C1 C6 C3 O7 174.47(15) . . . . ?
C1 C6 C5 C4 -65.1(2) . . . . ?
C5 C6 C2 O4 175.76(15) . . . . ?
C5 C6 C3 O7 53.0(2) . . . . ?
C5 C6 C1 O1 -66.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    Heat-sensitive,Energetic
####################################################################### 
# 
# 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_cu_lea_23_001d_0m
_database_code_depnum_ccdc_archive 'CCDC 2252054'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H8 Br N3 O9)'
_chemical_formula_sum            'C10 H16 Br2 N6 O18'
_chemical_formula_weight         668.11
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.6728(9)
_cell_length_b                   12.5692(19)
_cell_length_c                   27.033(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2267.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      69.45
_cell_measurement_theta_min      3.269
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    5.472
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1564 before and 0.0917 after correction.
The Ratio of minimum to maximum transmission is 0.7958.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            60346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.464
_diffrn_reflns_theta_min         3.269
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3664
_reflns_number_total             4620
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.546
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.6298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0854
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B), C4A(H4AA,H4AB),
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1(H1A,H1B)
;
_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
Br1A Br 0.70535(10) 0.76243(5) 0.55309(2) 0.0678(2) Uani 1 1 d . . . . .
Br1 Br 1.18239(9) 0.49272(6) 0.55213(2) 0.0726(2) Uani 1 1 d . . . . .
O1 O 0.6268(5) 0.4844(3) 0.65986(11) 0.0424(8) Uani 1 1 d . . . . .
O7A O 0.1393(5) 0.7547(3) 0.66084(11) 0.0414(8) Uani 1 1 d . . . . .
O4 O 0.6378(5) 0.2777(3) 0.59123(11) 0.0483(8) Uani 1 1 d . . . . .
O1A O 0.6914(5) 0.9178(3) 0.66839(12) 0.0456(8) Uani 1 1 d . . . . .
O9 O 1.1819(6) 0.3262(3) 0.66506(13) 0.0509(9) Uani 1 1 d . . . . .
O4A O 0.1435(5) 0.9587(3) 0.59518(11) 0.0484(8) Uani 1 1 d . . . . .
O8A O 0.0864(5) 0.7570(3) 0.74225(12) 0.0564(10) Uani 1 1 d . . . . .
O9A O -0.1066(6) 0.6659(3) 0.69381(14) 0.0592(10) Uani 1 1 d . . . . .
O2 O 0.5829(5) 0.4837(3) 0.74149(12) 0.0564(10) Uani 1 1 d . . . . .
N3A N 0.0320(6) 0.7240(3) 0.70311(14) 0.0425(9) Uani 1 1 d . . . . .
O3A O 0.7358(6) 1.0927(3) 0.67836(15) 0.0649(11) Uani 1 1 d . . . . .
O3 O 0.3892(6) 0.5759(3) 0.69381(14) 0.0607(10) Uani 1 1 d . . . . .
O8 O 1.3934(6) 0.2645(4) 0.71861(16) 0.0737(12) Uani 1 1 d . . . . .
O5A O -0.0767(6) 1.0730(3) 0.56983(15) 0.0662(11) Uani 1 1 d . . . . .
N1 N 0.5257(6) 0.5169(3) 0.70266(13) 0.0420(9) Uani 1 1 d . . . . .
O7 O 1.2293(7) 0.1514(3) 0.67377(17) 0.0696(12) Uani 1 1 d . . . . .
N2A N 0.0404(6) 1.0066(4) 0.55601(16) 0.0487(9) Uani 1 1 d . . . . .
N3 N 1.2766(6) 0.2383(4) 0.68730(16) 0.0520(10) Uani 1 1 d . . . . .
O6A O 0.0743(7) 0.9759(4) 0.51555(14) 0.0748(13) Uani 1 1 d . . . . .
O5 O 0.4349(6) 0.1569(3) 0.56394(16) 0.0736(12) Uani 1 1 d . . . . .
N1A N 0.7868(6) 1.0060(4) 0.69101(15) 0.0493(10) Uani 1 1 d . . . . .
N2 N 0.5386(6) 0.2300(4) 0.55132(17) 0.0512(10) Uani 1 1 d . . . . .
O6 O 0.5621(7) 0.2669(4) 0.51135(14) 0.0780(13) Uani 1 1 d . . . . .
O2A O 0.9086(6) 0.9795(4) 0.72088(16) 0.0739(12) Uani 1 1 d . . . . .
C5A C 0.4125(7) 0.8488(4) 0.62314(16) 0.0379(10) Uani 1 1 d . . . . .
C3A C 0.2973(8) 0.8299(4) 0.67160(16) 0.0401(11) Uani 1 1 d . . . . .
H3AA H 0.386329 0.801426 0.696695 0.048 Uiso 1 1 calc R U . . .
H3AB H 0.241090 0.896131 0.683666 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8971(7) 0.3934(4) 0.62061(15) 0.0357(10) Uani 1 1 d . . . . .
C2 C 0.7841(7) 0.4080(4) 0.66938(15) 0.0385(10) Uani 1 1 d . . . . .
H2A H 0.727440 0.340849 0.680248 0.046 Uiso 1 1 calc R U . . .
H2B H 0.873779 0.434078 0.694872 0.046 Uiso 1 1 calc R U . . .
C4 C 1.0370(7) 0.2981(4) 0.62711(18) 0.0444(11) Uani 1 1 d . . . . .
H4A H 0.961369 0.235824 0.637087 0.053 Uiso 1 1 calc R U . . .
H4B H 1.104935 0.282391 0.596242 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7584(7) 0.3694(4) 0.57703(16) 0.0416(11) Uani 1 1 d . . . . .
H3A H 0.673007 0.430100 0.570148 0.050 Uiso 1 1 calc R U . . .
H3B H 0.836128 0.353511 0.547627 0.050 Uiso 1 1 calc R U . . .
C4A C 0.2732(7) 0.8737(4) 0.57968(16) 0.0455(12) Uani 1 1 d . . . . .
H4AA H 0.350633 0.895144 0.550999 0.055 Uiso 1 1 calc R U . . .
H4AB H 0.195043 0.811337 0.571021 0.055 Uiso 1 1 calc R U . . .
C1A C 0.5322(7) 0.7487(4) 0.61133(17) 0.0451(11) Uani 1 1 d . . . . .
H1AA H 0.439583 0.690340 0.605971 0.054 Uiso 1 1 calc R U . . .
H1AB H 0.614456 0.730829 0.639718 0.054 Uiso 1 1 calc R U . . .
C2A C 0.5464(7) 0.9472(4) 0.63116(18) 0.0446(11) Uani 1 1 d . . . . .
H2AA H 0.613265 0.966677 0.600612 0.054 Uiso 1 1 calc R U . . .
H2AB H 0.466744 1.007170 0.642278 0.054 Uiso 1 1 calc R U . . .
C1 C 1.0101(8) 0.4972(4) 0.61011(17) 0.0468(11) Uani 1 1 d . . . . .
H1A H 1.091349 0.514637 0.638745 0.056 Uiso 1 1 calc R U . . .
H1B H 0.913129 0.553942 0.605828 0.056 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
Br1A C1A 1.961(5) . ?
Br1 C1 1.945(5) . ?
O1 N1 1.400(5) . ?
O1 C2 1.446(5) . ?
O7A N3A 1.403(5) . ?
O7A C3A 1.445(5) . ?
O4 N2 1.400(5) . ?
O4 C3 1.457(5) . ?
O1A N1A 1.417(5) . ?
O1A C2A 1.444(5) . ?
O9 N3 1.407(5) . ?
O9 C4 1.453(6) . ?
O4A N2A 1.399(5) . ?
O4A C4A 1.438(6) . ?
O8A N3A 1.193(5) . ?
O9A N3A 1.205(5) . ?
O2 N1 1.192(5) . ?
O3A N1A 1.192(6) . ?
O3 N1 1.199(5) . ?
O8 N3 1.197(6) . ?
O5A N2A 1.203(5) . ?
O7 N3 1.195(6) . ?
N2A O6A 1.182(5) . ?
O5 N2 1.200(6) . ?
N1A O2A 1.193(6) . ?
N2 O6 1.186(6) . ?
C5A C3A 1.537(6) . ?
C5A C4A 1.530(6) . ?
C5A C1A 1.524(6) . ?
C5A C2A 1.541(6) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C5 C2 1.530(6) . ?
C5 C4 1.529(6) . ?
C5 C3 1.528(6) . ?
C5 C1 1.534(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 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
N1 O1 C2 113.4(3) . . ?
N3A O7A C3A 112.9(3) . . ?
N2 O4 C3 113.4(3) . . ?
N1A O1A C2A 113.7(4) . . ?
N3 O9 C4 114.2(4) . . ?
N2A O4A C4A 113.3(3) . . ?
O8A N3A O7A 118.1(4) . . ?
O8A N3A O9A 129.0(4) . . ?
O9A N3A O7A 112.9(4) . . ?
O2 N1 O1 118.1(4) . . ?
O2 N1 O3 129.4(4) . . ?
O3 N1 O1 112.4(4) . . ?
O5A N2A O4A 112.5(4) . . ?
O6A N2A O4A 117.8(4) . . ?
O6A N2A O5A 129.7(4) . . ?
O8 N3 O9 112.2(5) . . ?
O7 N3 O9 117.9(4) . . ?
O7 N3 O8 129.8(5) . . ?
O3A N1A O1A 117.6(4) . . ?
O3A N1A O2A 130.1(5) . . ?
O2A N1A O1A 112.3(5) . . ?
O5 N2 O4 112.4(4) . . ?
O6 N2 O4 118.2(4) . . ?
O6 N2 O5 129.4(5) . . ?
C3A C5A C2A 107.1(4) . . ?
C4A C5A C3A 112.5(4) . . ?
C4A C5A C2A 107.2(4) . . ?
C1A C5A C3A 108.2(4) . . ?
C1A C5A C4A 109.0(4) . . ?
C1A C5A C2A 112.9(4) . . ?
O7A C3A C5A 107.1(3) . . ?
O7A C3A H3AA 110.3 . . ?
O7A C3A H3AB 110.3 . . ?
C5A C3A H3AA 110.3 . . ?
C5A C3A H3AB 110.3 . . ?
H3AA C3A H3AB 108.5 . . ?
C2 C5 C1 107.4(4) . . ?
C4 C5 C2 107.2(4) . . ?
C4 C5 C1 112.8(4) . . ?
C3 C5 C2 112.9(4) . . ?
C3 C5 C4 107.7(4) . . ?
C3 C5 C1 108.8(4) . . ?
O1 C2 C5 106.5(3) . . ?
O1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C5 C2 H2A 110.4 . . ?
C5 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O9 C4 C5 107.3(4) . . ?
O9 C4 H4A 110.3 . . ?
O9 C4 H4B 110.3 . . ?
C5 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
O4 C3 C5 106.7(3) . . ?
O4 C3 H3A 110.4 . . ?
O4 C3 H3B 110.4 . . ?
C5 C3 H3A 110.4 . . ?
C5 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O4A C4A C5A 107.1(4) . . ?
O4A C4A H4AA 110.3 . . ?
O4A C4A H4AB 110.3 . . ?
C5A C4A H4AA 110.3 . . ?
C5A C4A H4AB 110.3 . . ?
H4AA C4A H4AB 108.6 . . ?
Br1A C1A H1AA 108.8 . . ?
Br1A C1A H1AB 108.8 . . ?
C5A C1A Br1A 113.9(3) . . ?
C5A C1A H1AA 108.8 . . ?
C5A C1A H1AB 108.8 . . ?
H1AA C1A H1AB 107.7 . . ?
O1A C2A C5A 106.3(4) . . ?
O1A C2A H2AA 110.5 . . ?
O1A C2A H2AB 110.5 . . ?
C5A C2A H2AA 110.5 . . ?
C5A C2A H2AB 110.5 . . ?
H2AA C2A H2AB 108.7 . . ?
Br1 C1 H1A 108.6 . . ?
Br1 C1 H1B 108.6 . . ?
C5 C1 Br1 114.5(3) . . ?
C5 C1 H1A 108.6 . . ?
C5 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?

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
N3A O7A C3A C5A 175.3(3) . . . . ?
N1 O1 C2 C5 -172.2(4) . . . . ?
N2A O4A C4A C5A 165.9(4) . . . . ?
N3 O9 C4 C5 159.6(4) . . . . ?
N1A O1A C2A C5A -162.0(4) . . . . ?
N2 O4 C3 C5 -165.3(4) . . . . ?
C3A O7A N3A O8A -3.9(6) . . . . ?
C3A O7A N3A O9A 176.2(4) . . . . ?
C3A C5A C4A O4A 51.8(5) . . . . ?
C3A C5A C1A Br1A -175.6(3) . . . . ?
C3A C5A C2A O1A 65.4(5) . . . . ?
C2 O1 N1 O2 3.5(6) . . . . ?
C2 O1 N1 O3 -176.3(4) . . . . ?
C2 C5 C4 O9 -64.1(5) . . . . ?
C2 C5 C3 O4 -54.2(5) . . . . ?
C2 C5 C1 Br1 175.3(3) . . . . ?
C4 O9 N3 O8 -179.4(4) . . . . ?
C4 O9 N3 O7 -0.7(6) . . . . ?
C4 C5 C2 O1 -169.5(4) . . . . ?
C4 C5 C3 O4 64.0(4) . . . . ?
C4 C5 C1 Br1 57.4(5) . . . . ?
C3 O4 N2 O5 -177.7(4) . . . . ?
C3 O4 N2 O6 0.4(6) . . . . ?
C3 C5 C2 O1 -51.0(5) . . . . ?
C3 C5 C4 O9 174.0(4) . . . . ?
C3 C5 C1 Br1 -62.1(4) . . . . ?
C4A O4A N2A O5A 175.7(4) . . . . ?
C4A O4A N2A O6A -2.4(6) . . . . ?
C4A C5A C3A O7A 49.2(5) . . . . ?
C4A C5A C1A Br1A 61.8(4) . . . . ?
C4A C5A C2A O1A -173.6(4) . . . . ?
C1A C5A C3A O7A -71.3(4) . . . . ?
C1A C5A C4A O4A 171.8(4) . . . . ?
C1A C5A C2A O1A -53.6(5) . . . . ?
C2A O1A N1A O3A 1.8(6) . . . . ?
C2A O1A N1A O2A -178.6(4) . . . . ?
C2A C5A C3A O7A 166.8(3) . . . . ?
C2A C5A C4A O4A -65.7(5) . . . . ?
C2A C5A C1A Br1A -57.2(5) . . . . ?
C1 C5 C2 O1 69.1(5) . . . . ?
C1 C5 C4 O9 53.9(5) . . . . ?
C1 C5 C3 O4 -173.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF/Water'
_chemical_properties_physical    Heat-sensitive,Energetic
####################################################################### 
# 
# 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_121
_database_code_depnum_ccdc_archive 'CCDC 2252059'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled Apr  3 2018 11:26:26 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H8 I2 N2 O6'
_chemical_formula_sum            'C5 H8 I2 N2 O6'
_chemical_formula_weight         445.93
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.1616(8)
_cell_length_b                   13.0126(8)
_cell_length_c                   6.7544(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.802(5)
_cell_angle_gamma                90
_cell_volume                     1143.18(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3028
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      28.4610
_cell_measurement_theta_min      3.1030
_shelx_estimated_absorpt_T_max   0.405
_shelx_estimated_absorpt_T_min   0.248
_exptl_absorpt_coefficient_mu    5.513
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8699
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.214
_diffrn_ambient_temperature      293.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 107.00   0.50    2.00    --   20.00  54.00 120.00  358
  2  ω    -71.00 107.00   0.50    2.00    --   20.00  54.00 -90.00  356
  3  ω    -71.00 105.00   0.50    2.00    --   20.00  54.00   0.00  352
;
_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      0.0542663000
_diffrn_orient_matrix_UB_12      0.0052541000
_diffrn_orient_matrix_UB_13      0.0169636000
_diffrn_orient_matrix_UB_21      -0.0044142000
_diffrn_orient_matrix_UB_22      0.0477672000
_diffrn_orient_matrix_UB_23      -0.0511413000
_diffrn_orient_matrix_UB_31      -0.0028220000
_diffrn_orient_matrix_UB_32      0.0256447000
_diffrn_orient_matrix_UB_33      0.0917131000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1855
_reflns_number_total             2337
_reflns_odcompleteness_completeness 99.63
_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 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.207
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       0.0076(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D), C00E(H00E,H00F), C00F(H00G,H00H)
;
_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
I001 I 0.90678(2) 0.35742(2) 1.08271(4) 0.04446(14) Uani 1 1 d . . . . .
I002 I 0.86417(3) 0.62292(3) 0.46355(5) 0.04834(14) Uani 1 1 d . . . . .
O003 O 0.6705(2) 0.5373(2) 0.9852(4) 0.0380(8) Uani 1 1 d . . . . .
O004 O 0.6790(2) 0.3841(2) 0.4386(4) 0.0380(8) Uani 1 1 d . . . . .
O005 O 0.6059(2) 0.2965(3) 0.1846(5) 0.0526(9) Uani 1 1 d . . . . .
O006 O 0.5093(2) 0.3882(3) 0.3486(5) 0.0518(9) Uani 1 1 d . . . . .
O007 O 0.5626(3) 0.5993(3) 1.1643(5) 0.0641(11) Uani 1 1 d . . . . .
O008 O 0.6584(3) 0.7052(3) 1.0326(5) 0.0584(10) Uani 1 1 d . . . . .
N009 N 0.5896(3) 0.3543(3) 0.3139(6) 0.0385(9) Uani 1 1 d . . . . .
C00A C 0.8572(3) 0.4839(3) 0.6314(6) 0.0353(10) Uani 1 1 d . . . . .
H00A H 0.860467 0.426311 0.541372 0.042 Uiso 1 1 calc R . . . .
H00B H 0.917961 0.480720 0.732508 0.042 Uiso 1 1 calc R . . . .
C00B C 0.7512(3) 0.5621(3) 0.8682(6) 0.0364(10) Uani 1 1 d . . . . .
H00C H 0.815299 0.575637 0.955854 0.044 Uiso 1 1 calc R . . . .
H00D H 0.732681 0.622598 0.786662 0.044 Uiso 1 1 calc R . . . .
N00C N 0.6270(3) 0.6231(3) 1.0656(5) 0.0416(10) Uani 1 1 d . . . . .
C00D C 0.7626(3) 0.4695(3) 0.7358(6) 0.0302(10) Uani 1 1 d . . . . .
C00E C 0.6635(3) 0.4613(3) 0.5859(6) 0.0351(11) Uani 1 1 d . . . . .
H00E H 0.606788 0.441730 0.654350 0.042 Uiso 1 1 calc R . . . .
H00F H 0.647349 0.527039 0.520900 0.042 Uiso 1 1 calc R . . . .
C00F C 0.7755(4) 0.3692(3) 0.8531(6) 0.0356(11) Uani 1 1 d . . . . .
H00G H 0.778735 0.313548 0.758768 0.043 Uiso 1 1 calc R . . . .
H00H H 0.714347 0.358606 0.914498 0.043 Uiso 1 1 calc R . . . .


_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
I001 C00F 2.143(4) . ?
I002 C00A 2.144(4) . ?
O003 C00B 1.454(4) . ?
O003 N00C 1.401(4) . ?
O004 N009 1.393(4) . ?
O004 C00E 1.450(4) . ?
O005 N009 1.196(4) . ?
O006 N009 1.201(5) . ?
O007 N00C 1.196(4) . ?
O008 N00C 1.180(5) . ?
C00A C00D 1.533(5) . ?
C00B C00D 1.521(5) . ?
C00D C00E 1.527(5) . ?
C00D C00F 1.523(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N00C O003 C00B 114.2(3) . . ?
N009 O004 C00E 114.5(3) . . ?
O005 N009 O004 112.9(4) . . ?
O005 N009 O006 129.4(4) . . ?
O006 N009 O004 117.8(4) . . ?
C00D C00A I002 116.7(3) . . ?
O003 C00B C00D 106.9(3) . . ?
O007 N00C O003 112.1(4) . . ?
O008 N00C O003 118.2(4) . . ?
O008 N00C O007 129.7(4) . . ?
C00B C00D C00A 109.5(3) . . ?
C00B C00D C00E 107.1(3) . . ?
C00B C00D C00F 112.7(3) . . ?
C00E C00D C00A 112.0(3) . . ?
C00F C00D C00A 108.1(3) . . ?
C00F C00D C00E 107.5(3) . . ?
O004 C00E C00D 107.9(3) . . ?
C00D C00F I001 116.8(3) . . ?

_olex2_exptl_crystal_mounting_method 'N-Paratone on a nylon loop'
_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 3.505
_oxdiff_exptl_absorpt_empirical_full_min 0.679
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_cu_petn_cl2_c_0ma
_database_code_depnum_ccdc_archive 'CCDC 2252060'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2.5 H4 Cl N O3)'
_chemical_formula_sum            'C5 H8 Cl2 N2 O6'
_chemical_formula_weight         263.03
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.7924(15)
_cell_length_b                   6.6138(6)
_cell_length_c                   12.570(2)
_cell_angle_alpha                90
_cell_angle_beta                 121.680(4)
_cell_angle_gamma                90
_cell_volume                     1046.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7718
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      73.80
_cell_measurement_theta_min      4.13
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    5.773
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1284 before and 0.081 after correction.
The Ratio of minimum to maximum transmission is 0.73985.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13281
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.054
_diffrn_reflns_theta_min         4.133
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                1916
_reflns_number_total             2021
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.151
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.061(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2021
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.064
_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)+(0.0289P)²+0.1870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0632
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3(H3A,H3B), C1A(H1AA,H1AB), C1(H1A,H1B)
;
_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 0.41281(6) 0.72385(11) 0.82079(7) 0.0573(2) Uani 1 1 d . . . . .
Cl1A Cl 0.63160(6) 1.06402(12) 0.65481(7) 0.0649(2) Uani 1 1 d . . . . .
O1A O 0.43317(14) 0.5017(3) 0.57308(17) 0.0458(5) Uani 1 1 d . . . . .
O1 O 0.39410(13) 0.1595(3) 1.00951(16) 0.0422(4) Uani 1 1 d . . . . .
O2 O 0.23783(16) 0.0654(4) 0.8472(2) 0.0617(5) Uani 1 1 d . . . . .
O3A O 0.3779(2) 0.2739(4) 0.6487(2) 0.0724(7) Uani 1 1 d . . . . .
O2A O 0.26548(17) 0.3950(4) 0.4649(2) 0.0657(6) Uani 1 1 d . . . . .
N1 N 0.30157(17) 0.0452(4) 0.9560(2) 0.0454(5) Uani 1 1 d . . . . .
O3 O 0.29826(19) -0.0643(4) 1.0303(2) 0.0699(7) Uani 1 1 d . . . . .
N1A N 0.35073(19) 0.3817(4) 0.5600(2) 0.0476(5) Uani 1 1 d . . . . .
C2A C 0.500000 0.7594(5) 0.500000 0.0346(7) Uani 1 2 d S T P . .
C3A C 0.40323(19) 0.6289(4) 0.4657(2) 0.0388(5) Uani 1 1 d . . . . .
H3AA H 0.343052 0.713234 0.447380 0.047 Uiso 1 1 calc R U . . .
H3AB H 0.383993 0.546823 0.392878 0.047 Uiso 1 1 calc R U . . .
C3 C 0.40081(18) 0.2901(4) 0.9215(2) 0.0368(5) Uani 1 1 d . . . . .
H3A H 0.337833 0.373917 0.876928 0.044 Uiso 1 1 calc R U . . .
H3B H 0.407640 0.210693 0.861155 0.044 Uiso 1 1 calc R U . . .
C2 C 0.500000 0.4213(5) 1.000000 0.0337(7) Uani 1 2 d S T P . .
C1A C 0.5267(2) 0.8871(5) 0.6144(2) 0.0450(6) Uani 1 1 d . . . . .
H1AA H 0.547421 0.798172 0.684983 0.054 Uiso 1 1 calc R U . . .
H1AB H 0.463716 0.960159 0.597699 0.054 Uiso 1 1 calc R U . . .
C1 C 0.51857(19) 0.5498(4) 0.9118(2) 0.0412(5) Uani 1 1 d . . . . .
H1A H 0.526657 0.460999 0.855942 0.049 Uiso 1 1 calc R U . . .
H1B H 0.584281 0.624740 0.960786 0.049 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 C1 1.789(3) . ?
Cl1A C1A 1.791(3) . ?
O1A N1A 1.390(3) . ?
O1A C3A 1.448(3) . ?
O1 N1 1.389(3) . ?
O1 C3 1.448(3) . ?
O2 N1 1.193(3) . ?
O3A N1A 1.201(3) . ?
O2A N1A 1.201(3) . ?
N1 O3 1.203(3) . ?
C2A C3A 1.527(3) . ?
C2A C3A 1.527(3) 2_656 ?
C2A C1A 1.530(3) 2_656 ?
C2A C1A 1.530(3) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.536(3) . ?
C2 C1 1.532(3) 2_657 ?
C2 C1 1.532(3) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 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
N1A O1A C3A 113.65(19) . . ?
N1 O1 C3 113.59(17) . . ?
O2 N1 O1 118.6(2) . . ?
O2 N1 O3 128.9(2) . . ?
O3 N1 O1 112.5(2) . . ?
O3A N1A O1A 112.6(2) . . ?
O3A N1A O2A 129.2(3) . . ?
O2A N1A O1A 118.2(2) . . ?
C3A C2A C3A 111.2(3) . 2_656 ?
C3A C2A C1A 108.55(14) 2_656 2_656 ?
C3A C2A C1A 107.80(14) . 2_656 ?
C3A C2A C1A 107.80(14) 2_656 . ?
C3A C2A C1A 108.55(14) . . ?
C1A C2A C1A 113.0(3) . 2_656 ?
O1A C3A C2A 106.44(17) . . ?
O1A C3A H3AA 110.4 . . ?
O1A C3A H3AB 110.4 . . ?
C2A C3A H3AA 110.4 . . ?
C2A C3A H3AB 110.4 . . ?
H3AA C3A H3AB 108.6 . . ?
O1 C3 H3A 110.6 . . ?
O1 C3 H3B 110.6 . . ?
O1 C3 C2 105.76(16) . . ?
H3A C3 H3B 108.7 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C3 C2 C3 111.2(3) 2_657 . ?
C1 C2 C3 107.75(13) 2_657 . ?
C1 C2 C3 108.80(13) . . ?
C1 C2 C3 107.74(13) . 2_657 ?
C1 C2 C3 108.80(13) 2_657 2_657 ?
C1 C2 C1 112.6(3) . 2_657 ?
Cl1A C1A H1AA 109.1 . . ?
Cl1A C1A H1AB 109.1 . . ?
C2A C1A Cl1A 112.64(17) . . ?
C2A C1A H1AA 109.1 . . ?
C2A C1A H1AB 109.1 . . ?
H1AA C1A H1AB 107.8 . . ?
Cl1 C1 H1A 109.0 . . ?
Cl1 C1 H1B 109.0 . . ?
C2 C1 Cl1 113.01(15) . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C2 C3 56.08(13) . . . 2_657 ?
O1 C3 C2 C1 174.6(2) . . . . ?
O1 C3 C2 C1 -63.1(2) . . . 2_657 ?
N1 O1 C3 C2 173.07(19) . . . . ?
N1A O1A C3A C2A 176.05(19) . . . . ?
C3A O1A N1A O3A 178.3(2) . . . . ?
C3A O1A N1A O2A -0.4(3) . . . . ?
C3A C2A C3A O1A 57.85(14) 2_656 . . . ?
C3A C2A C1A Cl1A 64.9(3) 2_656 . . . ?
C3A C2A C1A Cl1A -174.56(18) . . . . ?
C3 O1 N1 O2 -0.8(3) . . . . ?
C3 O1 N1 O3 179.0(2) . . . . ?
C3 C2 C1 Cl1 63.2(2) . . . . ?
C3 C2 C1 Cl1 -176.14(17) 2_657 . . . ?
C1A C2A C3A O1A -60.6(2) . . . . ?
C1A C2A C3A O1A 176.7(2) 2_656 . . . ?
C1A C2A C1A Cl1A -55.03(14) 2_656 . . . ?
C1 C2 C1 Cl1 -56.16(13) 2_657 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_mo_petn_i3_j_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2252061'
loop_
_audit_author_name
_audit_author_address
'Kyle D. Spielvogel'
;Los Alamos National Laboratory 
United States of America
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H8 I3 N O3'
_chemical_formula_sum            'C5 H8 I3 N O3'
_chemical_formula_weight         510.82
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.9671(2)
_cell_length_b                   12.3623(5)
_cell_length_c                   26.6682(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2296.92(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8569
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.247
_shelx_estimated_absorpt_T_max   0.686
_shelx_estimated_absorpt_T_min   0.686
_exptl_absorpt_coefficient_mu    8.139
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.122 before and 0.071 after correction.
The Ratio of minimum to maximum transmission is 0.8250.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.954
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            71630
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.571
_diffrn_reflns_theta_min         2.247
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4808
_reflns_number_total             6434
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         2.062
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details 
;
 Flack x determined using 1727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.5757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H00A,H00B), C1A(H00I,H00J), C4A(H00K,H00L), C4(H00C,H00D), C2(H00E,H00F),
 C3A(H00M,H00N), C2A(H00O,H00P), C1(H00G,H00H)
;
_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
I2 I 0.12897(9) 0.76489(5) 0.31192(3) 0.05039(17) Uani 1 1 d . . . . .
I3 I 0.74004(9) 0.49850(5) 0.30714(2) 0.05106(17) Uani 1 1 d . . . . .
I3A I 0.11705(9) 0.51049(5) 0.69365(3) 0.05308(17) Uani 1 1 d . . . . .
I1A I 0.72061(10) 0.23734(6) 0.69586(3) 0.05791(19) Uani 1 1 d . . . . .
I1 I 0.14069(11) 0.51046(7) 0.43550(3) 0.0636(2) Uani 1 1 d . . . . .
I2A I 0.11993(11) 0.26007(6) 0.56840(3) 0.0674(2) Uani 1 1 d . . . . .
O3A O 0.9279(10) 0.5512(6) 0.5584(3) 0.0614(19) Uani 1 1 d . . . . .
O1A O 0.6958(9) 0.4648(5) 0.5939(2) 0.0502(16) Uani 1 1 d . . . . .
O1 O 0.7034(10) 0.7271(6) 0.4109(3) 0.0584(18) Uani 1 1 d . . . . .
N1A N 0.7972(13) 0.4902(7) 0.5509(3) 0.054(2) Uani 1 1 d . . . . .
O2A O 0.7477(15) 0.4480(7) 0.5130(3) 0.088(3) Uani 1 1 d . . . . .
O3 O 0.7644(14) 0.7122(6) 0.4919(3) 0.075(2) Uani 1 1 d . . . . .
N1 N 0.7932(11) 0.7590(7) 0.4549(3) 0.0490(18) Uani 1 1 d . . . . .
O2 O 0.9056(12) 0.8327(7) 0.4475(3) 0.075(2) Uani 1 1 d . . . . .
C3 C 0.5612(12) 0.6377(6) 0.3219(3) 0.0361(18) Uani 1 1 d . . . . .
H00A H 0.642255 0.701494 0.322359 0.043 Uiso 1 1 calc R U . . .
H00B H 0.471921 0.645850 0.294221 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4463(12) 0.6347(7) 0.3706(3) 0.0379(19) Uani 1 1 d . . . . .
C5A C 0.4287(13) 0.3785(7) 0.6340(3) 0.041(2) Uani 1 1 d . . . . .
C1A C 0.5459(12) 0.3781(6) 0.6821(3) 0.041(2) Uani 1 1 d . . . . .
H00I H 0.458379 0.386531 0.710073 0.049 Uiso 1 1 calc R U . . .
H00J H 0.629232 0.440947 0.681715 0.049 Uiso 1 1 calc R U . . .
C4A C 0.5562(15) 0.3776(8) 0.5871(4) 0.053(2) Uani 1 1 d . . . . .
H00K H 0.621018 0.308527 0.583848 0.063 Uiso 1 1 calc R U . . .
H00L H 0.479721 0.389955 0.557288 0.063 Uiso 1 1 calc R U . . .
C4 C 0.5768(13) 0.6352(8) 0.4168(3) 0.047(2) Uani 1 1 d . . . . .
H00C H 0.501350 0.642262 0.447154 0.056 Uiso 1 1 calc R U . . .
H00D H 0.650189 0.568640 0.418581 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3278(12) 0.7391(7) 0.3732(3) 0.044(2) Uani 1 1 d . . . . .
H00E H 0.415575 0.799977 0.374467 0.053 Uiso 1 1 calc R U . . .
H00F H 0.255677 0.738928 0.404345 0.053 Uiso 1 1 calc R U . . .
C3A C 0.3139(13) 0.4842(7) 0.6324(3) 0.044(2) Uani 1 1 d . . . . .
H00M H 0.241734 0.486017 0.601346 0.053 Uiso 1 1 calc R U . . .
H00N H 0.403979 0.544060 0.631615 0.053 Uiso 1 1 calc R U . . .
C2A C 0.3001(14) 0.2784(7) 0.6333(4) 0.051(2) Uani 1 1 d . . . . .
H00O H 0.218634 0.280226 0.662777 0.061 Uiso 1 1 calc R U . . .
H00P H 0.381046 0.214854 0.635975 0.061 Uiso 1 1 calc R U . . .
C1 C 0.3213(13) 0.5330(7) 0.3711(3) 0.043(2) Uani 1 1 d . . . . .
H00G H 0.404854 0.470553 0.368191 0.052 Uiso 1 1 calc R U . . .
H00H H 0.240277 0.534292 0.341495 0.052 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
I2 C2 2.166(9) . ?
I3 C3 2.161(8) . ?
I3A C3A 2.157(9) . ?
I1A C1A 2.155(8) . ?
I1 C1 2.148(9) . ?
I2A C2A 2.149(10) . ?
O3A N1A 1.199(11) . ?
O1A N1A 1.383(10) . ?
O1A C4A 1.463(11) . ?
O1 N1 1.388(10) . ?
O1 C4 1.447(11) . ?
N1A O2A 1.187(11) . ?
O3 N1 1.162(10) . ?
N1 O2 1.217(10) . ?
C3 H00A 0.9700 . ?
C3 H00B 0.9700 . ?
C3 C5 1.528(11) . ?
C5 C4 1.529(12) . ?
C5 C2 1.534(11) . ?
C5 C1 1.529(11) . ?
C5A C1A 1.519(12) . ?
C5A C4A 1.534(13) . ?
C5A C3A 1.533(12) . ?
C5A C2A 1.528(12) . ?
C1A H00I 0.9700 . ?
C1A H00J 0.9700 . ?
C4A H00K 0.9700 . ?
C4A H00L 0.9700 . ?
C4 H00C 0.9700 . ?
C4 H00D 0.9700 . ?
C2 H00E 0.9700 . ?
C2 H00F 0.9700 . ?
C3A H00M 0.9700 . ?
C3A H00N 0.9700 . ?
C2A H00O 0.9700 . ?
C2A H00P 0.9700 . ?
C1 H00G 0.9700 . ?
C1 H00H 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
N1A O1A C4A 113.9(7) . . ?
N1 O1 C4 114.0(7) . . ?
O3A N1A O1A 113.1(8) . . ?
O2A N1A O3A 129.7(9) . . ?
O2A N1A O1A 117.2(8) . . ?
O3 N1 O1 120.0(8) . . ?
O3 N1 O2 128.5(9) . . ?
O2 N1 O1 111.4(7) . . ?
I3 C3 H00A 108.3 . . ?
I3 C3 H00B 108.3 . . ?
H00A C3 H00B 107.4 . . ?
C5 C3 I3 115.9(5) . . ?
C5 C3 H00A 108.3 . . ?
C5 C3 H00B 108.3 . . ?
C3 C5 C4 111.9(7) . . ?
C3 C5 C2 107.4(7) . . ?
C3 C5 C1 109.0(7) . . ?
C4 C5 C2 106.3(7) . . ?
C1 C5 C4 109.6(7) . . ?
C1 C5 C2 112.7(7) . . ?
C1A C5A C4A 112.1(8) . . ?
C1A C5A C3A 107.9(7) . . ?
C1A C5A C2A 108.9(7) . . ?
C3A C5A C4A 106.6(7) . . ?
C2A C5A C4A 108.9(8) . . ?
C2A C5A C3A 112.6(8) . . ?
I1A C1A H00I 108.1 . . ?
I1A C1A H00J 108.1 . . ?
C5A C1A I1A 116.8(6) . . ?
C5A C1A H00I 108.1 . . ?
C5A C1A H00J 108.1 . . ?
H00I C1A H00J 107.3 . . ?
O1A C4A C5A 106.2(7) . . ?
O1A C4A H00K 110.5 . . ?
O1A C4A H00L 110.5 . . ?
C5A C4A H00K 110.5 . . ?
C5A C4A H00L 110.5 . . ?
H00K C4A H00L 108.7 . . ?
O1 C4 C5 106.2(7) . . ?
O1 C4 H00C 110.5 . . ?
O1 C4 H00D 110.5 . . ?
C5 C4 H00C 110.5 . . ?
C5 C4 H00D 110.5 . . ?
H00C C4 H00D 108.7 . . ?
I2 C2 H00E 108.4 . . ?
I2 C2 H00F 108.4 . . ?
C5 C2 I2 115.7(6) . . ?
C5 C2 H00E 108.4 . . ?
C5 C2 H00F 108.4 . . ?
H00E C2 H00F 107.4 . . ?
I3A C3A H00M 108.3 . . ?
I3A C3A H00N 108.3 . . ?
C5A C3A I3A 116.0(6) . . ?
C5A C3A H00M 108.3 . . ?
C5A C3A H00N 108.3 . . ?
H00M C3A H00N 107.4 . . ?
I2A C2A H00O 108.3 . . ?
I2A C2A H00P 108.3 . . ?
C5A C2A I2A 116.0(6) . . ?
C5A C2A H00O 108.3 . . ?
C5A C2A H00P 108.3 . . ?
H00O C2A H00P 107.4 . . ?
I1 C1 H00G 108.2 . . ?
I1 C1 H00H 108.2 . . ?
C5 C1 I1 116.5(6) . . ?
C5 C1 H00G 108.2 . . ?
C5 C1 H00H 108.2 . . ?
H00G C1 H00H 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I3 C3 C5 C4 64.7(8) . . . . ?
I3 C3 C5 C2 -179.0(5) . . . . ?
I3 C3 C5 C1 -56.7(8) . . . . ?
N1A O1A C4A C5A -167.5(7) . . . . ?
N1 O1 C4 C5 162.4(7) . . . . ?
C3 C5 C4 O1 53.1(9) . . . . ?
C3 C5 C2 I2 59.1(8) . . . . ?
C3 C5 C1 I1 -179.0(5) . . . . ?
C1A C5A C4A O1A -50.7(10) . . . . ?
C1A C5A C3A I3A -59.8(8) . . . . ?
C1A C5A C2A I2A -179.7(6) . . . . ?
C4A O1A N1A O3A -170.7(8) . . . . ?
C4A O1A N1A O2A 7.6(13) . . . . ?
C4A C5A C1A I1A -64.0(9) . . . . ?
C4A C5A C3A I3A 179.7(6) . . . . ?
C4A C5A C2A I2A -57.2(9) . . . . ?
C4 O1 N1 O3 0.5(13) . . . . ?
C4 O1 N1 O2 176.3(8) . . . . ?
C4 C5 C2 I2 179.1(5) . . . . ?
C4 C5 C1 I1 58.2(8) . . . . ?
C2 C5 C4 O1 -63.9(9) . . . . ?
C2 C5 C1 I1 -59.9(9) . . . . ?
C3A C5A C1A I1A 179.0(6) . . . . ?
C3A C5A C4A O1A 67.1(9) . . . . ?
C3A C5A C2A I2A 60.8(9) . . . . ?
C2A C5A C1A I1A 56.5(9) . . . . ?
C2A C5A C4A O1A -171.2(7) . . . . ?
C2A C5A C3A I3A 60.4(9) . . . . ?
C1 C5 C4 O1 174.1(7) . . . . ?
C1 C5 C2 I2 -60.9(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
