# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_srt-(l)-tart
_database_code_depnum_ccdc_archive 'CCDC 2208609'
loop_
_audit_author_name
_audit_author_address
'Paulo Carvalho Jr'
;Federal University of Mato Grosso do Sul
Brazil
;
_audit_update_record             
;
2023-01-27 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 Cl2 N, C4 H5 O6'
_chemical_formula_sum            'C21 H23 Cl2 N O6'
_chemical_formula_weight         456.30
_chemical_absolute_configuration ad
_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           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                   17.628(2)
_cell_length_b                   5.4719(7)
_cell_length_c                   21.601(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.194(2)
_cell_angle_gamma                90
_cell_volume                     2071.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.94
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0800
0.00 1.00 0.00 0.0700
1.00 0.00 0.00 0.0300
-1.00 0.00 0.00 0.0200
0.00 0.00 1.00 0.0150
0.00 0.00 -1.00 0.0150

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41429
_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         27.101
_diffrn_reflns_theta_min         2.846
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4250
_reflns_number_total             4549
_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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.063
_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)+(0.0253P)²+3.8121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C12B-C5 \\sim C12-C5
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15B) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C17B) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 C12B, C17B, C16B, C15B, C14B, C13B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C12(0.75) C17(0.75) H17(0.75) C16(0.75) C13(0.75) H13(0.75)
 C15(0.75) C14(0.75) H14(0.75) Cl1(0.75) Cl2(0.75) Cl2A(0.25) Cl1A(0.25)
 C12B(0.25) C17B(0.25) H17B(0.25) C13B(0.25) H13B(0.25) C16B(0.25) C14B(0.25)
 H14B(0.25) C15B(0.25) H5A(0.75) H5B(0.25)
6.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20), C2(H2), C5(H5A), C5(H5B)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), N1(H1A,H1B), C4(H4A,H4B)
6.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C9(H9), C8(H8), C17(H17), C13(H13), C14(H14), C17B(H17B),
 C13B(H13B), C14B(H14B)
6.d Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_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
O3 O 0.84230(10) 0.8609(4) 0.06660(9) 0.0153(4) Uani 1 1 d . . . . .
H3 H 0.8086 0.8979 0.0376 0.023 Uiso 1 1 calc R U . . .
O4 O 0.75243(10) 0.3825(4) 0.04837(9) 0.0145(4) Uani 1 1 d . . . . .
H4 H 0.7344 0.2446 0.0556 0.022 Uiso 1 1 calc R U . . .
O5 O 0.94404(11) 0.3709(4) 0.11776(9) 0.0188(4) Uani 1 1 d . . . . .
O2 O 0.69549(11) 0.9498(3) 0.08326(9) 0.0144(4) Uani 1 1 d . . . . .
C18 C 0.72720(15) 0.7895(5) 0.11951(12) 0.0122(5) Uani 1 1 d . . . . .
O6 O 0.89927(11) 0.3517(4) 0.01885(9) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.8576 0.3768 -0.0030 0.025 Uiso 1 1 calc R U . . .
C21 C 0.89016(15) 0.3820(5) 0.07782(13) 0.0139(5) Uani 1 1 d . . . . .
C19 C 0.80971(15) 0.7178(5) 0.11105(13) 0.0122(5) Uani 1 1 d . . . . .
H19 H 0.8411 0.7427 0.1520 0.015 Uiso 1 1 calc R U . . .
C3 C 0.58771(18) 0.1173(5) 0.20622(14) 0.0192(6) Uani 1 1 d . . . . .
H3A H 0.6014 0.0520 0.1661 0.023 Uiso 1 1 calc R U . . .
H3B H 0.5646 -0.0170 0.2285 0.023 Uiso 1 1 calc R U . . .
O1 O 0.69807(11) 0.6791(4) 0.16126(9) 0.0167(4) Uani 1 1 d . . . . .
N1 N 0.55244(13) 0.4932(4) 0.14336(11) 0.0139(5) Uani 1 1 d . . . . .
H1A H 0.5215 0.6266 0.1419 0.017 Uiso 1 1 calc R U . . .
H1B H 0.6011 0.5453 0.1543 0.017 Uiso 1 1 calc R U . . .
C4 C 0.65963(17) 0.2056(6) 0.24509(14) 0.0208(6) Uani 1 1 d . . . . .
H4A H 0.6824 0.3422 0.2234 0.025 Uiso 1 1 calc R U . . .
H4B H 0.6974 0.0712 0.2501 0.025 Uiso 1 1 calc R U . . .
C20 C 0.81098(15) 0.4421(5) 0.09602(13) 0.0125(5) Uani 1 1 d . . . . .
H20 H 0.8026 0.3478 0.1344 0.015 Uiso 1 1 calc R U . . .
C1 C 0.54806(17) 0.3831(6) 0.07976(13) 0.0189(6) Uani 1 1 d . . . . .
H1C H 0.5617 0.5065 0.0500 0.028 Uiso 1 1 calc R U . . .
H1D H 0.4960 0.3252 0.0675 0.028 Uiso 1 1 calc R U . . .
H1E H 0.5837 0.2454 0.0801 0.028 Uiso 1 1 calc R U . . .
C2 C 0.52990(16) 0.3215(5) 0.19355(13) 0.0157(6) Uani 1 1 d . . . . .
H2 H 0.4796 0.2462 0.1783 0.019 Uiso 1 1 calc R U . . .
C11 C 0.51955(17) 0.4696(6) 0.25092(14) 0.0187(6) Uani 1 1 d . . . . .
C10 C 0.45446(19) 0.6168(6) 0.25048(16) 0.0252(7) Uani 1 1 d . . . . .
H10 H 0.4178 0.6173 0.2149 0.030 Uiso 1 1 calc R U . . .
C6 C 0.57240(18) 0.4641(6) 0.30405(14) 0.0235(7) Uani 1 1 d . . . . .
C7 C 0.5592(2) 0.6089(8) 0.35490(16) 0.0343(8) Uani 1 1 d . . . . .
H7 H 0.5945 0.6052 0.3914 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4428(2) 0.7616(8) 0.30119(17) 0.0364(9) Uani 1 1 d . . . . .
H9 H 0.3989 0.8626 0.3001 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4956(2) 0.7579(9) 0.35330(18) 0.0442(10) Uani 1 1 d . . . . .
H8 H 0.4883 0.8579 0.3881 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7125(4) 0.4137(14) 0.3430(3) 0.0216(15) Uani 0.75 1 d D . P A 1
C17 C 0.7446(3) 0.3214(10) 0.3999(2) 0.0300(10) Uani 0.75 1 d . . P A 1
H17 H 0.7230 0.1795 0.4164 0.036 Uiso 0.75 1 calc R U P A 1
C16 C 0.8084(8) 0.433(2) 0.4339(6) 0.037(3) Uani 0.75 1 d . . P A 1
C13 C 0.7468(3) 0.6208(10) 0.3201(3) 0.0251(11) Uani 0.75 1 d . U P A 1
H13 H 0.7269 0.6859 0.2809 0.030 Uiso 0.75 1 calc R U P A 1
C15 C 0.8393(3) 0.6356(11) 0.4098(3) 0.0325(12) Uani 0.75 1 d . U P A 1
C14 C 0.8086(3) 0.7327(9) 0.3529(2) 0.0302(10) Uani 0.75 1 d . . P A 1
H14 H 0.8302 0.8752 0.3368 0.036 Uiso 0.75 1 calc R U P A 1
Cl1 Cl 0.91757(8) 0.7775(3) 0.44991(7) 0.0567(4) Uani 0.75 1 d . . P A 1
Cl2 Cl 0.84288(12) 0.3126(4) 0.50363(7) 0.0806(7) Uani 0.75 1 d . . P A 1
Cl2A Cl 0.8688(2) 0.8317(7) 0.36248(19) 0.0385(8) Uani 0.25 1 d . . P A 2
Cl1A Cl 0.9045(3) 0.5515(9) 0.4904(2) 0.0510(11) Uani 0.25 1 d . . P A 2
C12B C 0.7029(13) 0.360(5) 0.3583(8) 0.024(5) Uani 0.25 1 d D U P A 2
C17B C 0.7438(10) 0.540(4) 0.3412(8) 0.023(3) Uani 0.25 1 d . U P A 2
H17B H 0.7313 0.6229 0.3028 0.028 Uiso 0.25 1 calc R U P A 2
C13B C 0.7158(10) 0.229(4) 0.4143(7) 0.035(3) Uani 0.25 1 d . U P A 2
H13B H 0.6828 0.1021 0.4248 0.042 Uiso 0.25 1 calc R U P A 2
C16B C 0.8091(10) 0.608(3) 0.3833(9) 0.032(3) Uani 0.25 1 d . U P A 2
C14B C 0.7802(10) 0.299(4) 0.4535(7) 0.037(3) Uani 0.25 1 d . U P A 2
H14B H 0.7931 0.2274 0.4933 0.044 Uiso 0.25 1 calc R U P A 2
C15B C 0.824(3) 0.479(10) 0.431(2) 0.044(7) Uani 0.25 1 d . U P A 2
C5 C 0.64103(19) 0.2913(6) 0.30925(14) 0.0261(7) Uani 1 1 d D . . . .
H5A H 0.6284 0.1446 0.3338 0.031 Uiso 0.75 1 calc R U P A 1
H5B H 0.6199 0.1400 0.3268 0.031 Uiso 0.25 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3 0.8400 . ?
O3 C19 1.408(3) . ?
O4 H4 0.8400 . ?
O4 C20 1.415(3) . ?
O5 C21 1.214(3) . ?
O2 C18 1.265(3) . ?
C18 C19 1.536(4) . ?
C18 O1 1.242(3) . ?
O6 H6 0.8400 . ?
O6 C21 1.311(3) . ?
C21 C20 1.526(4) . ?
C19 H19 1.0000 . ?
C19 C20 1.544(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.522(4) . ?
C3 C2 1.517(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.495(3) . ?
N1 C2 1.520(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.532(4) . ?
C20 H20 1.0000 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 H2 1.0000 . ?
C2 C11 1.508(4) . ?
C11 C10 1.401(4) . ?
C11 C6 1.398(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.385(5) . ?
C6 C7 1.394(4) . ?
C6 C5 1.530(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(6) . ?
C9 H9 0.9500 . ?
C9 C8 1.381(5) . ?
C8 H8 0.9500 . ?
C12 C17 1.391(7) . ?
C12 C13 1.400(8) . ?
C12 C5 1.539(7) . ?
C17 H17 0.9500 . ?
C17 C16 1.413(14) . ?
C16 C15 1.364(11) . ?
C16 Cl2 1.696(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(7) . ?
C15 C14 1.394(8) . ?
C15 Cl1 1.732(6) . ?
C14 H14 0.9500 . ?
Cl2A C16B 1.707(19) . ?
Cl1A C15B 1.86(5) . ?
C12B C17B 1.30(3) . ?
C12B C13B 1.40(2) . ?
C12B C5 1.485(18) . ?
C17B H17B 0.9500 . ?
C17B C16B 1.44(3) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.40(2) . ?
C16B C15B 1.24(5) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.37(4) . ?
C5 H5A 1.0000 . ?
C5 H5B 1.0000 . ?

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
C19 O3 H3 109.5 . . ?
C20 O4 H4 109.5 . . ?
O2 C18 C19 117.7(2) . . ?
O1 C18 O2 126.7(3) . . ?
O1 C18 C19 115.7(2) . . ?
C21 O6 H6 109.5 . . ?
O5 C21 O6 121.0(2) . . ?
O5 C21 C20 119.7(2) . . ?
O6 C21 C20 119.3(2) . . ?
O3 C19 C18 113.6(2) . . ?
O3 C19 H19 107.4 . . ?
O3 C19 C20 112.6(2) . . ?
C18 C19 H19 107.4 . . ?
C18 C19 C20 108.1(2) . . ?
C20 C19 H19 107.4 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.7(2) . . ?
H1A N1 H1B 107.6 . . ?
C1 N1 H1A 108.6 . . ?
C1 N1 H1B 108.6 . . ?
C1 N1 C2 114.5(2) . . ?
C2 N1 H1A 108.6 . . ?
C2 N1 H1B 108.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.5(3) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
O4 C20 C21 112.3(2) . . ?
O4 C20 C19 110.6(2) . . ?
O4 C20 H20 108.8 . . ?
C21 C20 C19 107.4(2) . . ?
C21 C20 H20 108.8 . . ?
C19 C20 H20 108.8 . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C3 C2 N1 111.2(2) . . ?
C3 C2 H2 108.1 . . ?
N1 C2 H2 108.1 . . ?
C11 C2 C3 112.7(2) . . ?
C11 C2 N1 108.5(2) . . ?
C11 C2 H2 108.1 . . ?
C10 C11 C2 118.4(3) . . ?
C6 C11 C2 122.3(3) . . ?
C6 C11 C10 119.4(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C6 C5 121.7(3) . . ?
C7 C6 C11 118.8(3) . . ?
C7 C6 C5 119.4(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.3 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C17 C12 C13 117.2(6) . . ?
C17 C12 C5 119.6(6) . . ?
C13 C12 C5 123.1(5) . . ?
C12 C17 H17 119.1 . . ?
C12 C17 C16 121.7(7) . . ?
C16 C17 H17 119.1 . . ?
C17 C16 Cl2 118.8(6) . . ?
C15 C16 C17 118.8(9) . . ?
C15 C16 Cl2 122.4(9) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 H13 119.2 . . ?
C16 C15 C14 120.9(7) . . ?
C16 C15 Cl1 120.2(7) . . ?
C14 C15 Cl1 118.9(5) . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C17B C12B C13B 126.1(17) . . ?
C17B C12B C5 112.2(15) . . ?
C13B C12B C5 121.6(17) . . ?
C12B C17B H17B 121.7 . . ?
C12B C17B C16B 116.5(18) . . ?
C16B C17B H17B 121.7 . . ?
C12B C13B H13B 122.3 . . ?
C14B C13B C12B 115.4(18) . . ?
C14B C13B H13B 122.3 . . ?
C17B C16B Cl2A 119.5(15) . . ?
C15B C16B Cl2A 123(3) . . ?
C15B C16B C17B 117(3) . . ?
C13B C14B H14B 122.4 . . ?
C15B C14B C13B 115(3) . . ?
C15B C14B H14B 122.4 . . ?
C16B C15B Cl1A 122(3) . . ?
C16B C15B C14B 129(4) . . ?
C14B C15B Cl1A 108(3) . . ?
C4 C5 C12 108.5(4) . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 102.4 . . ?
C6 C5 C4 111.6(2) . . ?
C6 C5 C12 111.5(4) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 102.4 . . ?
C12 C5 H5A 108.4 . . ?
C12B C5 C4 120.7(10) . . ?
C12B C5 C6 114.2(11) . . ?
C12B C5 H5B 102.4 . . ?

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
O3 C19 C20 O4 -77.7(3) . . . . ?
O3 C19 C20 C21 45.1(3) . . . . ?
O5 C21 C20 O4 -163.6(3) . . . . ?
O5 C21 C20 C19 74.6(3) . . . . ?
O2 C18 C19 O3 5.8(3) . . . . ?
O2 C18 C19 C20 -119.8(3) . . . . ?
C18 C19 C20 O4 48.5(3) . . . . ?
C18 C19 C20 C21 171.3(2) . . . . ?
O6 C21 C20 O4 18.8(4) . . . . ?
O6 C21 C20 C19 -103.0(3) . . . . ?
C3 C4 C5 C6 -48.5(4) . . . . ?
C3 C4 C5 C12 -171.7(4) . . . . ?
C3 C4 C5 C12B 173.2(11) . . . . ?
C3 C2 C11 C10 -162.7(3) . . . . ?
C3 C2 C11 C6 17.2(4) . . . . ?
O1 C18 C19 O3 -175.3(2) . . . . ?
O1 C18 C19 C20 59.1(3) . . . . ?
N1 C2 C11 C10 73.7(3) . . . . ?
N1 C2 C11 C6 -106.4(3) . . . . ?
C4 C3 C2 N1 76.5(3) . . . . ?
C4 C3 C2 C11 -45.7(3) . . . . ?
C1 N1 C2 C3 68.3(3) . . . . ?
C1 N1 C2 C11 -167.2(2) . . . . ?
C2 C3 C4 C5 62.9(3) . . . . ?
C2 C11 C10 C9 -178.3(3) . . . . ?
C2 C11 C6 C7 179.2(3) . . . . ?
C2 C11 C6 C5 -5.0(4) . . . . ?
C11 C10 C9 C8 -1.0(6) . . . . ?
C11 C6 C7 C8 -0.6(6) . . . . ?
C11 C6 C5 C4 20.7(4) . . . . ?
C11 C6 C5 C12 142.3(4) . . . . ?
C11 C6 C5 C12B 161.9(9) . . . . ?
C10 C11 C6 C7 -0.9(5) . . . . ?
C10 C11 C6 C5 174.9(3) . . . . ?
C10 C9 C8 C7 -0.6(7) . . . . ?
C6 C11 C10 C9 1.7(5) . . . . ?
C6 C7 C8 C9 1.4(7) . . . . ?
C7 C6 C5 C4 -163.5(3) . . . . ?
C7 C6 C5 C12 -42.0(5) . . . . ?
C7 C6 C5 C12B -22.3(10) . . . . ?
C12 C17 C16 C15 -0.4(15) . . . . ?
C12 C17 C16 Cl2 178.7(7) . . . . ?
C12 C13 C14 C15 1.4(8) . . . . ?
C17 C12 C13 C14 -1.4(9) . . . . ?
C17 C12 C5 C4 -121.0(6) . . . . ?
C17 C12 C5 C6 115.7(6) . . . . ?
C17 C16 C15 C14 0.4(15) . . . . ?
C17 C16 C15 Cl1 -179.9(7) . . . . ?
C16 C15 C14 C13 -0.9(10) . . . . ?
C13 C12 C17 C16 0.9(11) . . . . ?
C13 C12 C5 C4 60.7(7) . . . . ?
C13 C12 C5 C6 -62.6(7) . . . . ?
Cl1 C15 C14 C13 179.4(4) . . . . ?
Cl2 C16 C15 C14 -178.7(7) . . . . ?
Cl2 C16 C15 Cl1 1.0(14) . . . . ?
Cl2A C16B C15B Cl1A 10(6) . . . . ?
Cl2A C16B C15B C14B 178(4) . . . . ?
C12B C17B C16B Cl2A 176.6(17) . . . . ?
C12B C17B C16B C15B 4(4) . . . . ?
C12B C13B C14B C15B -3(4) . . . . ?
C17B C12B C13B C14B -2(4) . . . . ?
C17B C12B C5 C4 60(2) . . . . ?
C17B C12B C5 C6 -77(2) . . . . ?
C17B C16B C15B Cl1A -178(3) . . . . ?
C17B C16B C15B C14B -10(7) . . . . ?
C13B C12B C17B C16B 1(4) . . . . ?
C13B C12B C5 C4 -116.5(18) . . . . ?
C13B C12B C5 C6 106(2) . . . . ?
C13B C14B C15B Cl1A 178.3(19) . . . . ?
C13B C14B C15B C16B 9(7) . . . . ?
C5 C6 C7 C8 -176.5(4) . . . . ?
C5 C12 C17 C16 -177.5(8) . . . . ?
C5 C12 C13 C14 176.9(5) . . . . ?
C5 C12B C17B C16B -175.0(14) . . . . ?
C5 C12B C13B C14B 174.1(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_srt_(d)-tart
_database_code_depnum_ccdc_archive 'CCDC 2208611'
loop_
_audit_author_name
_audit_author_address
'Paulo Carvalho Jr'
;Federal University of Mato Grosso do Sul
Brazil
;
_audit_update_record             
;
2023-01-27 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_audit_creation_date             2023-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 Cl2 N, C4 H5 O6, 2(H2 O)'
_chemical_formula_sum            'C21 H27 Cl2 N O8'
_chemical_formula_weight         492.33
_chemical_absolute_configuration ad
_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      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                   7.1781(3)
_cell_length_b                   7.8320(3)
_cell_length_c                   41.7968(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2349.77(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      71.44
_cell_measurement_theta_min      4.23
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.569
_exptl_absorpt_coefficient_mu    2.892
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1655 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.6775.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            36659
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.113
_diffrn_reflns_theta_min         4.231
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3746
_reflns_number_total             4616
_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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.111(13)
_refine_ls_extinction_coef       0.0036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.039
_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)+(0.0963P)²+0.5790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 OW2(HW2A,HW2B), OW1(HW1A,HW1B)
2.b Ternary CH refined with riding coordinates:
 C20(H20), C19(H19), C2(H2), C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C17(H17), C7(H7), C13(H13), C9(H9), C8(H8)
2.e Tetrahedral OH refined with riding coordinates:
 O6(H6)
2.f Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
2.g Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.1001(3) -0.0559(3) 0.26757(5) 0.1098(7) Uani 1 1 d . . . . .
Cl2 Cl 1.4104(3) 0.2262(3) 0.27583(5) 0.1121(7) Uani 1 1 d . . . . .
O6 O 0.6353(4) 0.2222(4) 0.46272(9) 0.0629(8) Uani 1 1 d . . . . .
H6 H 0.5219 0.2097 0.4621 0.094 Uiso 1 1 calc R U . . .
O3 O 0.9090(5) 0.1005(5) 0.41219(8) 0.0631(8) Uani 1 1 d . . . . .
H3 H 0.9896 0.0831 0.3987 0.095 Uiso 1 1 calc R U . . .
O4 O 0.9913(5) -0.0854(4) 0.47205(9) 0.0644(9) Uani 1 1 d . . . . .
H4 H 1.0969 -0.0851 0.4795 0.097 Uiso 1 1 calc R U . . .
OW2 O 0.7939(5) 0.6121(5) 0.48860(9) 0.0657(9) Uani 1 1 d G . . . .
HW2A H 0.8879 0.5756 0.4989 0.099 Uiso 1 1 d G U . . .
HW2B H 0.8154 0.7178 0.4858 0.099 Uiso 1 1 d G U . . .
O2 O 1.2912(4) 0.2240(5) 0.46118(9) 0.0671(9) Uani 1 1 d . . . . .
O5 O 0.6278(5) -0.0458(5) 0.47995(12) 0.0783(11) Uani 1 1 d . . . . .
O1 O 1.2693(5) 0.1102(6) 0.41213(11) 0.0788(11) Uani 1 1 d . . . . .
OW1 O 0.5862(5) 0.2787(5) 0.38928(10) 0.0728(10) Uani 1 1 d G . . . .
HW1A H 0.4857 0.2238 0.3924 0.109 Uiso 1 1 d G U . . .
HW1B H 0.6720 0.2070 0.3932 0.109 Uiso 1 1 d G U . . .
N1 N 0.6507(6) 0.5730(6) 0.42497(10) 0.0626(10) Uani 1 1 d . . . . .
H1A H 0.6463 0.4782 0.4133 0.075 Uiso 1 1 calc R U . . .
H1B H 0.7130 0.5486 0.4428 0.075 Uiso 1 1 calc R U . . .
C20 C 0.9240(6) 0.0852(6) 0.47001(11) 0.0531(10) Uani 1 1 d . . . . .
H20 H 0.9700 0.1491 0.4886 0.064 Uiso 1 1 calc R U . . .
C18 C 1.2031(6) 0.1665(6) 0.43726(13) 0.0583(11) Uani 1 1 d . . . . .
C19 C 0.9920(6) 0.1723(6) 0.44007(11) 0.0535(10) Uani 1 1 d . . . . .
H19 H 0.9547 0.2925 0.4412 0.064 Uiso 1 1 calc R U . . .
C21 C 0.7121(6) 0.0817(7) 0.47132(12) 0.0577(11) Uani 1 1 d . . . . .
C2 C 0.7600(7) 0.7072(7) 0.40646(13) 0.0614(11) Uani 1 1 d . . . . .
H2 H 0.7463 0.8165 0.4177 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7715(8) 0.6571(7) 0.34627(13) 0.0650(12) Uani 1 1 d . . . . .
C12 C 0.9887(7) 0.4163(7) 0.32728(12) 0.0628(11) Uani 1 1 d . . . . .
C10 C 0.5252(9) 0.8293(8) 0.36825(15) 0.0745(14) Uani 1 1 d . . . . .
H10 H 0.4698 0.8825 0.3857 0.089 Uiso 1 1 calc R U . . .
C11 C 0.6858(7) 0.7290(7) 0.37308(12) 0.0626(12) Uani 1 1 d . . . . .
C4 C 1.0054(7) 0.5162(7) 0.38343(13) 0.0656(12) Uani 1 1 d . . . . .
H4A H 0.9304 0.4176 0.3890 0.079 Uiso 1 1 calc R U . . .
H4B H 1.1354 0.4834 0.3850 0.079 Uiso 1 1 calc R U . . .
C5 C 0.9620(7) 0.5688(7) 0.34894(13) 0.0646(12) Uani 1 1 d . . . . .
H5 H 1.0560 0.6534 0.3428 0.078 Uiso 1 1 calc R U . . .
C14 C 0.8918(9) 0.1447(9) 0.30549(15) 0.0805(15) Uani 1 1 d . . . . .
H14 H 0.8006 0.0612 0.3034 0.097 Uiso 1 1 calc R U . . .
C17 C 1.1588(7) 0.3941(8) 0.31223(13) 0.0687(13) Uani 1 1 d . . . . .
H17 H 1.2509 0.4769 0.3143 0.082 Uiso 1 1 calc R U . . .
C7 C 0.6904(9) 0.6779(8) 0.31652(14) 0.0766(15) Uani 1 1 d . . . . .
H7 H 0.7450 0.6264 0.2988 0.092 Uiso 1 1 calc R U . . .
C3 C 0.9667(7) 0.6587(7) 0.40686(14) 0.0662(12) Uani 1 1 d . . . . .
H3A H 1.0413 0.7576 0.4013 0.079 Uiso 1 1 calc R U . . .
H3B H 1.0018 0.6226 0.4282 0.079 Uiso 1 1 calc R U . . .
C16 C 1.1933(8) 0.2474(9) 0.29384(14) 0.0754(15) Uani 1 1 d . . . . .
C15 C 1.0600(9) 0.1240(8) 0.29070(14) 0.0743(14) Uani 1 1 d . . . . .
C13 C 0.8557(8) 0.2897(8) 0.32372(14) 0.0737(14) Uani 1 1 d . . . . .
H13 H 0.7405 0.3018 0.3337 0.088 Uiso 1 1 calc R U . . .
C1 C 0.4586(8) 0.6204(8) 0.43378(15) 0.0733(14) Uani 1 1 d . . . . .
H1C H 0.3853 0.6340 0.4147 0.110 Uiso 1 1 calc R U . . .
H1D H 0.4602 0.7259 0.4455 0.110 Uiso 1 1 calc R U . . .
H1E H 0.4054 0.5323 0.4469 0.110 Uiso 1 1 calc R U . . .
C9 C 0.4485(10) 0.8506(8) 0.33854(17) 0.0854(17) Uani 1 1 d . . . . .
H9 H 0.3419 0.9166 0.3359 0.103 Uiso 1 1 calc R U . . .
C8 C 0.5315(11) 0.7726(10) 0.31247(17) 0.0892(18) Uani 1 1 d . . . . .
H8 H 0.4796 0.7845 0.2922 0.107 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 C15 1.733(6) . ?
Cl2 C16 1.739(6) . ?
O6 H6 0.8200 . ?
O6 C21 1.283(6) . ?
O3 H3 0.8200 . ?
O3 C19 1.425(6) . ?
O4 H4 0.8200 . ?
O4 C20 1.424(6) . ?
OW2 HW2A 0.8494 . ?
OW2 HW2B 0.8500 . ?
O2 C18 1.266(6) . ?
O5 C21 1.222(6) . ?
O1 C18 1.234(6) . ?
OW1 HW1A 0.8501 . ?
OW1 HW1B 0.8500 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C2 1.523(7) . ?
N1 C1 1.474(7) . ?
C20 H20 0.9800 . ?
C20 C19 1.506(7) . ?
C20 C21 1.522(6) . ?
C18 C19 1.520(6) . ?
C19 H19 0.9800 . ?
C2 H2 0.9800 . ?
C2 C11 1.503(8) . ?
C2 C3 1.532(7) . ?
C6 C11 1.397(8) . ?
C6 C5 1.537(8) . ?
C6 C7 1.382(9) . ?
C12 C5 1.511(7) . ?
C12 C17 1.385(8) . ?
C12 C13 1.384(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.410(8) . ?
C10 C9 1.369(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.531(8) . ?
C4 C3 1.511(7) . ?
C5 H5 0.9800 . ?
C14 H14 0.9300 . ?
C14 C15 1.366(9) . ?
C14 C13 1.392(9) . ?
C17 H17 0.9300 . ?
C17 C16 1.404(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16 C15 1.366(9) . ?
C13 H13 0.9300 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C9 H9 0.9300 . ?
C9 C8 1.384(10) . ?
C8 H8 0.9300 . ?

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
C21 O6 H6 109.5 . . ?
C19 O3 H3 109.5 . . ?
C20 O4 H4 109.5 . . ?
HW2A OW2 HW2B 104.6 . . ?
HW1A OW1 HW1B 104.5 . . ?
H1A N1 H1B 107.4 . . ?
C2 N1 H1A 108.3 . . ?
C2 N1 H1B 108.3 . . ?
C1 N1 H1A 108.3 . . ?
C1 N1 H1B 108.3 . . ?
C1 N1 C2 115.8(4) . . ?
O4 C20 H20 108.5 . . ?
O4 C20 C19 111.4(4) . . ?
O4 C20 C21 108.6(4) . . ?
C19 C20 H20 108.5 . . ?
C19 C20 C21 111.2(4) . . ?
C21 C20 H20 108.5 . . ?
O2 C18 C19 115.2(4) . . ?
O1 C18 O2 127.4(4) . . ?
O1 C18 C19 117.4(5) . . ?
O3 C19 C20 111.4(4) . . ?
O3 C19 C18 110.0(4) . . ?
O3 C19 H19 107.8 . . ?
C20 C19 C18 112.0(4) . . ?
C20 C19 H19 107.8 . . ?
C18 C19 H19 107.8 . . ?
O6 C21 C20 113.8(4) . . ?
O5 C21 O6 124.8(4) . . ?
O5 C21 C20 121.4(5) . . ?
N1 C2 H2 108.0 . . ?
N1 C2 C3 108.8(4) . . ?
C11 C2 N1 111.5(4) . . ?
C11 C2 H2 108.0 . . ?
C11 C2 C3 112.4(4) . . ?
C3 C2 H2 108.0 . . ?
C11 C6 C5 121.0(5) . . ?
C7 C6 C11 119.3(5) . . ?
C7 C6 C5 119.5(5) . . ?
C17 C12 C5 118.9(5) . . ?
C17 C12 C13 118.0(5) . . ?
C13 C12 C5 122.9(5) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(6) . . ?
C6 C11 C2 122.9(5) . . ?
C6 C11 C10 118.0(5) . . ?
C10 C11 C2 119.1(5) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C3 C4 C5 112.0(5) . . ?
C6 C5 H5 106.8 . . ?
C12 C5 C6 115.1(4) . . ?
C12 C5 C4 109.0(4) . . ?
C12 C5 H5 106.8 . . ?
C4 C5 C6 111.7(4) . . ?
C4 C5 H5 106.8 . . ?
C15 C14 H14 119.7 . . ?
C15 C14 C13 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C12 C17 H17 119.8 . . ?
C12 C17 C16 120.5(5) . . ?
C16 C17 H17 119.8 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.7(6) . . ?
C8 C7 H7 119.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 C2 110.7(4) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C17 C16 Cl2 118.2(5) . . ?
C15 C16 Cl2 121.2(5) . . ?
C15 C16 C17 120.5(5) . . ?
C14 C15 Cl1 119.7(5) . . ?
C14 C15 C16 119.4(5) . . ?
C16 C15 Cl1 120.9(5) . . ?
C12 C13 C14 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.2(6) . . ?
C8 C9 H9 120.4 . . ?
C7 C8 C9 120.0(6) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?

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
Cl2 C16 C15 Cl1 -2.0(7) . . . . ?
Cl2 C16 C15 C14 179.4(5) . . . . ?
O4 C20 C19 O3 68.8(4) . . . . ?
O4 C20 C19 C18 -54.8(5) . . . . ?
O4 C20 C21 O6 -165.5(4) . . . . ?
O4 C20 C21 O5 14.5(7) . . . . ?
O2 C18 C19 O3 -178.5(4) . . . . ?
O2 C18 C19 C20 -54.0(6) . . . . ?
O1 C18 C19 O3 2.8(7) . . . . ?
O1 C18 C19 C20 127.2(5) . . . . ?
N1 C2 C11 C6 -101.6(6) . . . . ?
N1 C2 C11 C10 79.9(6) . . . . ?
N1 C2 C3 C4 76.9(6) . . . . ?
C19 C20 C21 O6 -42.5(6) . . . . ?
C19 C20 C21 O5 137.5(5) . . . . ?
C21 C20 C19 O3 -52.5(5) . . . . ?
C21 C20 C19 C18 -176.2(4) . . . . ?
C6 C7 C8 C9 0.1(10) . . . . ?
C12 C17 C16 Cl2 -179.5(4) . . . . ?
C12 C17 C16 C15 -0.4(9) . . . . ?
C10 C9 C8 C7 -1.1(11) . . . . ?
C11 C2 C3 C4 -47.1(6) . . . . ?
C11 C6 C5 C12 145.1(5) . . . . ?
C11 C6 C5 C4 20.0(7) . . . . ?
C11 C6 C7 C8 2.4(9) . . . . ?
C11 C10 C9 C8 -0.5(10) . . . . ?
C5 C6 C11 C2 -7.6(8) . . . . ?
C5 C6 C11 C10 170.9(5) . . . . ?
C5 C6 C7 C8 -172.4(6) . . . . ?
C5 C12 C17 C16 175.2(5) . . . . ?
C5 C12 C13 C14 -174.9(6) . . . . ?
C5 C4 C3 C2 62.1(6) . . . . ?
C17 C12 C5 C6 139.6(5) . . . . ?
C17 C12 C5 C4 -94.0(6) . . . . ?
C17 C12 C13 C14 -0.2(9) . . . . ?
C17 C16 C15 Cl1 179.0(5) . . . . ?
C17 C16 C15 C14 0.4(9) . . . . ?
C7 C6 C11 C2 177.6(5) . . . . ?
C7 C6 C11 C10 -3.9(8) . . . . ?
C7 C6 C5 C12 -40.1(7) . . . . ?
C7 C6 C5 C4 -165.2(5) . . . . ?
C3 C2 C11 C6 20.9(7) . . . . ?
C3 C2 C11 C10 -157.5(5) . . . . ?
C3 C4 C5 C6 -47.0(6) . . . . ?
C3 C4 C5 C12 -175.4(4) . . . . ?
C15 C14 C13 C12 0.1(10) . . . . ?
C13 C12 C5 C6 -45.8(7) . . . . ?
C13 C12 C5 C4 80.7(6) . . . . ?
C13 C12 C17 C16 0.3(8) . . . . ?
C13 C14 C15 Cl1 -178.9(5) . . . . ?
C13 C14 C15 C16 -0.2(10) . . . . ?
C1 N1 C2 C11 -69.9(5) . . . . ?
C1 N1 C2 C3 165.5(4) . . . . ?
C9 C10 C11 C2 -178.4(6) . . . . ?
C9 C10 C11 C6 3.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
