####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1855250'
loop_
_audit_author_name
_audit_author_address
'St?phane MASSIP'
;UMS 3033 IECB
France
;
_audit_update_record             
;
2018-07-11 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT250_shelx               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.2 Note
RESPONSE: The described molecule of solvent is strongly disordered but doesn't need to be squeezed.
;
# Added during the CSD deposition process: Wednesday 11 July 2018 03:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 Cl3 N2 O6'
_chemical_formula_weight         403.63

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.6577(3)
_cell_length_b                   9.0916(2)
_cell_length_c                   11.5007(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.302(2)
_cell_angle_gamma                90
_cell_volume                     1701.73(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    12802
_cell_measurement_theta_min      3.9210
_cell_measurement_theta_max      75.6060

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.188
_shelx_estimated_absorpt_T_min   0.575
_shelx_estimated_absorpt_T_max   0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43'
_exptl_absorpt_special_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            12488
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.485
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             2865
_reflns_number_gt                2824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.822
_reflns_Friedel_fraction_full    0.824

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+1.8944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2865
_refine_ls_number_parameters     259
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.13686(16) 0.1897(4) 0.4547(2) 0.0309(6) Uani 1 1 d . . . . .
C2 C 0.11495(18) 0.0660(4) 0.3900(3) 0.0300(7) Uani 1 1 d . . . . .
N3 N 0.09779(16) -0.0585(3) 0.4499(2) 0.0320(6) Uani 1 1 d . . . . .
H3 H 0.0796 -0.1360 0.4064 0.038 Uiso 1 1 calc R U . . .
C4 C 0.10653(19) -0.0720(4) 0.5710(3) 0.0332(8) Uani 1 1 d . . . . .
C5 C 0.1121(2) 0.0693(5) 0.6370(3) 0.0414(9) Uani 1 1 d . . . . .
H5A H 0.1455 0.0523 0.7180 0.050 Uiso 1 1 calc R U . . .
H5B H 0.0560 0.0960 0.6458 0.050 Uiso 1 1 calc R U . . .
C6 C 0.14813(19) 0.2012(4) 0.5842(3) 0.0311(7) Uani 1 1 d . . . . .
H6 H 0.2080 0.2099 0.6210 0.037 Uiso 1 1 calc R U . . .
O7 O 0.10607(13) 0.3276(3) 0.6127(2) 0.0325(5) Uani 1 1 d . . . . .
C8 C 0.1547(2) 0.4582(4) 0.6306(3) 0.0344(8) Uani 1 1 d . . . . .
H8A H 0.2068 0.4374 0.6879 0.041 Uiso 1 1 calc R U . . .
H8B H 0.1250 0.5349 0.6657 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1738(2) 0.5156(4) 0.5161(3) 0.0308(7) Uani 1 1 d . . . . .
H9 H 0.2086 0.6058 0.5338 0.037 Uiso 1 1 calc R U . . .
O10 O 0.21853(12) 0.4048(3) 0.4646(2) 0.0312(5) Uani 1 1 d . . . . .
C11 C 0.16114(19) 0.3154(4) 0.3884(3) 0.0314(7) Uani 1 1 d . . . . .
H11 H 0.1863 0.2778 0.3226 0.038 Uiso 1 1 calc R U . . .
O12 O 0.10964(17) 0.0611(3) 0.28237(19) 0.0425(6) Uani 1 1 d . . . . .
O13 O 0.10403(17) -0.1906(3) 0.6177(2) 0.0454(7) Uani 1 1 d . . . . .
C14 C 0.09979(19) 0.5497(4) 0.4173(3) 0.0309(7) Uani 1 1 d . . . . .
H14 H 0.0496 0.5744 0.4481 0.037 Uiso 1 1 calc R U . . .
O15 O 0.12249(15) 0.6639(3) 0.3445(2) 0.0349(6) Uani 1 1 d . . . . .
C16 C 0.0929(2) 0.6231(4) 0.2227(3) 0.0328(8) Uani 1 1 d . . . . .
O17 O 0.09759(17) 0.4678(3) 0.2228(2) 0.0420(7) Uani 1 1 d . . . . .
C18 C 0.0880(2) 0.4145(4) 0.3360(3) 0.0325(8) Uani 1 1 d . . . . .
H18 H 0.0339 0.3649 0.3321 0.039 Uiso 1 1 calc R U . . .
C19 C 0.0062(2) 0.6780(6) 0.1789(4) 0.0557(12) Uani 1 1 d . . . . .
H19A H -0.0156 0.6401 0.0986 0.084 Uiso 1 1 calc R U . . .
H19B H 0.0062 0.7858 0.1772 0.084 Uiso 1 1 calc R U . . .
H19C H -0.0284 0.6438 0.2327 0.084 Uiso 1 1 calc R U . . .
C20 C 0.1518(2) 0.6824(5) 0.1518(3) 0.0420(9) Uani 1 1 d . . . . .
H20A H 0.2065 0.6408 0.1822 0.063 Uiso 1 1 calc R U . . .
H20B H 0.1543 0.7898 0.1590 0.063 Uiso 1 1 calc R U . . .
H20C H 0.1329 0.6552 0.0679 0.063 Uiso 1 1 calc R U . . .
C21 C 0.1395(4) 0.2019(6) 1.0386(4) 0.0765(16) Uani 1 1 d D . . . .
H21A H 0.1054 0.2250 1.0981 0.092 Uiso 0.5 1 calc R U P A 1
H21B H 0.1071 0.1879 1.1017 0.092 Uiso 0.3 1 calc R U P B 2
H21C H 0.1124 0.2437 1.1010 0.092 Uiso 0.2 1 calc R U P C 3
Cl22 Cl 0.1258(6) 0.3352(9) 0.9277(6) 0.0797(18) Uani 0.5 1 d D . P D 1
Cl23 Cl 0.2359(4) 0.1888(13) 1.1035(7) 0.196(5) Uani 0.5 1 d D . P D 1
Cl24 Cl 0.1150(9) 0.0285(7) 0.9770(5) 0.170(5) Uani 0.5 1 d D . P D 1
Cl32 Cl 0.0884(9) 0.3296(14) 0.9364(9) 0.088(3) Uani 0.3 1 d D . P D 2
Cl33 Cl 0.2534(5) 0.2511(9) 1.1170(7) 0.071(2) Uani 0.3 1 d D . P D 2
Cl34 Cl 0.1605(6) 0.0296(11) 0.9867(9) 0.075(2) Uani 0.3 1 d D . P D 2
Cl42 Cl 0.0584(8) 0.0761(19) 0.9574(14) 0.125(5) Uiso 0.2 1 d D . P D 3
Cl43 Cl 0.2379(12) 0.245(4) 1.092(2) 0.165(11) Uiso 0.2 1 d D . P D 3
Cl44 Cl 0.121(3) 0.344(3) 0.927(3) 0.206(16) Uiso 0.2 1 d D . P D 3


_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
N1 C2 1.355(5) . ?
N1 C6 1.465(4) . ?
N1 C11 1.478(4) . ?
C2 O12 1.223(4) . ?
C2 N3 1.385(4) . ?
N3 C4 1.374(4) . ?
C4 O13 1.210(5) . ?
C4 C5 1.485(6) . ?
C5 C6 1.525(5) . ?
C6 O7 1.419(4) . ?
O7 C8 1.427(5) . ?
C8 C9 1.512(4) . ?
C9 O10 1.452(4) . ?
C9 C14 1.520(4) . ?
O10 C11 1.409(4) . ?
C11 C18 1.532(5) . ?
C14 O15 1.435(4) . ?
C14 C18 1.532(5) . ?
O15 C16 1.432(4) . ?
C16 O17 1.414(4) . ?
C16 C20 1.503(5) . ?
C16 C19 1.510(5) . ?
O17 C18 1.430(4) . ?
C21 Cl23 1.625(10) . ?
C21 Cl43 1.67(2) . ?
C21 Cl24 1.741(8) . ?
C21 Cl22 1.739(8) . ?
C21 Cl32 1.740(11) . ?
C21 Cl34 1.738(11) . ?
C21 Cl44 1.80(2) . ?
C21 Cl42 1.862(15) . ?
C21 Cl33 1.971(10) . ?
Cl42 Cl42 2.36(3) 2_557 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 125.3(3) . . ?
C2 N1 C11 115.5(3) . . ?
C6 N1 C11 118.6(3) . . ?
O12 C2 N1 122.6(3) . . ?
O12 C2 N3 119.7(3) . . ?
N1 C2 N3 117.7(3) . . ?
C4 N3 C2 126.0(3) . . ?
O13 C4 N3 121.5(3) . . ?
O13 C4 C5 123.3(3) . . ?
N3 C4 C5 115.0(3) . . ?
C4 C5 C6 117.6(3) . . ?
O7 C6 N1 109.3(3) . . ?
O7 C6 C5 106.8(2) . . ?
N1 C6 C5 111.9(3) . . ?
C6 O7 C8 114.4(2) . . ?
O7 C8 C9 112.3(3) . . ?
O10 C9 C8 109.7(3) . . ?
O10 C9 C14 103.9(2) . . ?
C8 C9 C14 115.7(3) . . ?
C11 O10 C9 108.4(2) . . ?
O10 C11 N1 110.4(2) . . ?
O10 C11 C18 106.4(3) . . ?
N1 C11 C18 112.0(3) . . ?
O15 C14 C9 108.1(3) . . ?
O15 C14 C18 103.9(2) . . ?
C9 C14 C18 105.7(3) . . ?
C14 O15 C16 107.7(3) . . ?
O17 C16 O15 104.5(3) . . ?
O17 C16 C20 108.4(3) . . ?
O15 C16 C20 108.0(3) . . ?
O17 C16 C19 112.3(3) . . ?
O15 C16 C19 110.2(3) . . ?
C20 C16 C19 112.9(3) . . ?
C16 O17 C18 108.8(3) . . ?
O17 C18 C11 108.9(3) . . ?
O17 C18 C14 105.0(3) . . ?
C11 C18 C14 104.1(2) . . ?
Cl23 C21 Cl24 104.1(7) . . ?
Cl23 C21 Cl22 110.5(6) . . ?
Cl24 C21 Cl22 110.5(4) . . ?
Cl32 C21 Cl34 118.3(6) . . ?
Cl43 C21 Cl44 95.7(16) . . ?
Cl43 C21 Cl42 151.5(12) . . ?
Cl44 C21 Cl42 95.0(12) . . ?
Cl32 C21 Cl33 116.2(7) . . ?
Cl34 C21 Cl33 96.7(5) . . ?
C21 Cl42 Cl42 111.5(9) . 2_557 ?

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
C6 N1 C2 O12 -177.0(3) . . . . ?
C11 N1 C2 O12 -5.2(4) . . . . ?
C6 N1 C2 N3 3.3(4) . . . . ?
C11 N1 C2 N3 175.1(3) . . . . ?
O12 C2 N3 C4 175.3(3) . . . . ?
N1 C2 N3 C4 -5.0(5) . . . . ?
C2 N3 C4 O13 -166.9(3) . . . . ?
C2 N3 C4 C5 18.0(5) . . . . ?
O13 C4 C5 C6 156.2(3) . . . . ?
N3 C4 C5 C6 -28.7(5) . . . . ?
C2 N1 C6 O7 -132.4(3) . . . . ?
C11 N1 C6 O7 56.1(3) . . . . ?
C2 N1 C6 C5 -14.3(4) . . . . ?
C11 N1 C6 C5 174.1(3) . . . . ?
C4 C5 C6 O7 146.1(3) . . . . ?
C4 C5 C6 N1 26.6(4) . . . . ?
N1 C6 O7 C8 -91.1(3) . . . . ?
C5 C6 O7 C8 147.7(3) . . . . ?
C6 O7 C8 C9 70.3(3) . . . . ?
O7 C8 C9 O10 -59.7(3) . . . . ?
O7 C8 C9 C14 57.5(4) . . . . ?
C8 C9 O10 C11 89.7(3) . . . . ?
C14 C9 O10 C11 -34.6(3) . . . . ?
C9 O10 C11 N1 -89.7(3) . . . . ?
C9 O10 C11 C18 32.2(3) . . . . ?
C2 N1 C11 O10 -150.7(3) . . . . ?
C6 N1 C11 O10 21.7(4) . . . . ?
C2 N1 C11 C18 90.8(3) . . . . ?
C6 N1 C11 C18 -96.8(3) . . . . ?
O10 C9 C14 O15 -87.9(3) . . . . ?
C8 C9 C14 O15 151.7(3) . . . . ?
O10 C9 C14 C18 22.8(3) . . . . ?
C8 C9 C14 C18 -97.5(3) . . . . ?
C9 C14 O15 C16 134.9(3) . . . . ?
C18 C14 O15 C16 22.9(3) . . . . ?
C14 O15 C16 O17 -32.4(3) . . . . ?
C14 O15 C16 C20 -147.7(3) . . . . ?
C14 O15 C16 C19 88.5(4) . . . . ?
O15 C16 O17 C18 28.9(3) . . . . ?
C20 C16 O17 C18 144.0(3) . . . . ?
C19 C16 O17 C18 -90.6(3) . . . . ?
C16 O17 C18 C11 -125.7(3) . . . . ?
C16 O17 C18 C14 -14.7(3) . . . . ?
O10 C11 C18 O17 95.5(3) . . . . ?
N1 C11 C18 O17 -143.7(3) . . . . ?
O10 C11 C18 C14 -16.1(3) . . . . ?
N1 C11 C18 C14 104.7(3) . . . . ?
O15 C14 C18 O17 -5.1(3) . . . . ?
C9 C14 C18 O17 -118.9(3) . . . . ?
O15 C14 C18 C11 109.2(3) . . . . ?
C9 C14 C18 C11 -4.5(3) . . . . ?
Cl43 C21 Cl42 Cl42 144(2) . . . 2_557 ?
Cl44 C21 Cl42 Cl42 -104.5(17) . . . 2_557 ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.050



