# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2505171'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2025-11-24 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2023-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
miquel.barcelo@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 N O5 S, H2 O'
_chemical_formula_sum            'C8 H13 N O6 S'
_chemical_formula_weight         251.25
_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'
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'
S S 0.3331 0.5567 '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                   6.8391(3)
_cell_length_b                   11.2218(5)
_cell_length_c                   13.7253(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1053.38(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9130
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.22
_shelx_estimated_absorpt_T_max   0.636
_shelx_estimated_absorpt_T_min   0.329
_exptl_absorpt_coefficient_mu    2.922
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1561 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.5508.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24647
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.285
_diffrn_reflns_theta_min         5.091
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                1890
_reflns_number_total             1890
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker Apex4, 2021'
_computing_data_collection       'Bruker Apex4, 2021'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2-1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2-1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.123
_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)+(0.0354P)²+0.4518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.83(2)
 0.17(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C5C(H5C), C6C(H6C)
3.d Idealised Me refined as rotating group:
 C21C(H21A,H21B,H21C)
3.e Idealised tetrahedral OH refined as rotating group:
 O31C(H31C), O41C(H41C)
;
_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
S1 S 0.63397(8) 0.19102(4) 0.18685(4) 0.00994(18) Uani 1 1 d . . . . .
C2 C 0.4692(4) 0.0755(2) 0.22061(17) 0.0118(5) Uani 1 1 d . . . . .
H2A H 0.485439 0.008316 0.174514 0.014 Uiso 1 1 calc R U . . .
H2B H 0.505900 0.046279 0.286181 0.014 Uiso 1 1 calc R U . . .
C3 C 0.2531(4) 0.1113(2) 0.22229(17) 0.0132(5) Uani 1 1 d . . . . .
H3A H 0.223496 0.159027 0.163455 0.016 Uiso 1 1 calc R U . . .
H3B H 0.171456 0.038516 0.220146 0.016 Uiso 1 1 calc R U . . .
O11 O 0.8277(2) 0.14052(14) 0.19505(13) 0.0158(4) Uani 1 1 d . . . . .
O12 O 0.5822(2) 0.22075(15) 0.08571(12) 0.0150(4) Uani 1 1 d . . . . .
O13 O 0.5977(2) 0.29204(14) 0.25152(11) 0.0135(4) Uani 1 1 d . . . . .
N1C N 0.2015(3) 0.18126(18) 0.30994(14) 0.0121(4) Uani 1 1 d . . . . .
C2C C 0.1834(3) 0.1261(2) 0.39835(18) 0.0134(5) Uani 1 1 d . . . . .
C3C C 0.1633(3) 0.1952(2) 0.48128(16) 0.0125(4) Uani 1 1 d . . . . .
C4C C 0.1567(3) 0.3199(2) 0.47411(17) 0.0127(5) Uani 1 1 d . . . . .
C5C C 0.1598(4) 0.3716(2) 0.38190(18) 0.0136(5) Uani 1 1 d . . . . .
H5C H 0.144560 0.455296 0.374590 0.016 Uiso 1 1 calc R U . . .
C6C C 0.1849(3) 0.3005(2) 0.30200(17) 0.0137(5) Uani 1 1 d . . . . .
H6C H 0.190730 0.336100 0.239265 0.016 Uiso 1 1 calc R U . . .
C21C C 0.1819(4) -0.0068(2) 0.40525(19) 0.0188(5) Uani 1 1 d . . . . .
H21A H 0.058807 -0.037504 0.378658 0.028 Uiso 1 1 calc R U . . .
H21B H 0.194023 -0.030704 0.473656 0.028 Uiso 1 1 calc R U . . .
H21C H 0.291798 -0.039325 0.367960 0.028 Uiso 1 1 calc R U . . .
O31C O 0.1533(3) 0.13840(15) 0.56769(12) 0.0165(4) Uani 1 1 d . . . . .
H31C H 0.134530 0.188349 0.612306 0.025 Uiso 1 1 calc R U . . .
O41C O 0.1462(3) 0.38060(14) 0.55752(12) 0.0167(4) Uani 1 1 d . . . . .
H41C H 0.164682 0.453361 0.546505 0.025 Uiso 1 1 calc R U . . .
O1W O 0.1979(3) 0.60765(15) 0.55523(13) 0.0162(4) Uani 1 1 d G . . . .
H1WA H 0.100995 0.656517 0.564673 0.024 Uiso 1 1 d G U . . .
H1WB H 0.264515 0.639528 0.507993 0.024 Uiso 1 1 d G 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
S1 C2 1.779(2) . ?
S1 O11 1.4452(17) . ?
S1 O12 1.4710(17) . ?
S1 O13 1.4610(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 N1C 1.479(3) . ?
N1C C2C 1.368(3) . ?
N1C C6C 1.348(3) . ?
C2C C3C 1.384(3) . ?
C2C C21C 1.494(4) . ?
C3C C4C 1.404(4) . ?
C3C O31C 1.348(3) . ?
C4C C5C 1.392(3) . ?
C4C O41C 1.334(3) . ?
C5C H5C 0.9500 . ?
C5C C6C 1.367(3) . ?
C6C H6C 0.9500 . ?
C21C H21A 0.9800 . ?
C21C H21B 0.9800 . ?
C21C H21C 0.9800 . ?
O31C H31C 0.8400 . ?
O41C H41C 0.8400 . ?
O1W H1WA 0.8700 . ?
O1W H1WB 0.8694 . ?

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
O11 S1 C2 105.92(11) . . ?
O11 S1 O12 112.52(10) . . ?
O11 S1 O13 114.37(10) . . ?
O12 S1 C2 104.99(10) . . ?
O13 S1 C2 107.45(10) . . ?
O13 S1 O12 110.88(9) . . ?
S1 C2 H2A 108.5 . . ?
S1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 S1 115.05(17) . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1C C3 C2 112.45(19) . . ?
N1C C3 H3A 109.1 . . ?
N1C C3 H3B 109.1 . . ?
C2C N1C C3 120.2(2) . . ?
C6C N1C C3 118.8(2) . . ?
C6C N1C C2C 120.9(2) . . ?
N1C C2C C3C 119.0(2) . . ?
N1C C2C C21C 120.6(2) . . ?
C3C C2C C21C 120.4(2) . . ?
C2C C3C C4C 120.3(2) . . ?
O31C C3C C2C 117.6(2) . . ?
O31C C3C C4C 122.1(2) . . ?
C5C C4C C3C 118.6(2) . . ?
O41C C4C C3C 116.8(2) . . ?
O41C C4C C5C 124.6(2) . . ?
C4C C5C H5C 120.4 . . ?
C6C C5C C4C 119.2(2) . . ?
C6C C5C H5C 120.4 . . ?
N1C C6C C5C 121.7(2) . . ?
N1C C6C H6C 119.2 . . ?
C5C C6C H6C 119.2 . . ?
C2C C21C H21A 109.5 . . ?
C2C C21C H21B 109.5 . . ?
C2C C21C H21C 109.5 . . ?
H21A C21C H21B 109.5 . . ?
H21A C21C H21C 109.5 . . ?
H21B C21C H21C 109.5 . . ?
C3C O31C H31C 109.5 . . ?
C4C O41C H41C 109.5 . . ?
H1WA O1W H1WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5C H5C O11 0.95 2.30 3.198(3) 158.4 3_655 yes
O31C H31C O13 0.84 1.90 2.629(2) 144.6 4_456 yes
O41C H41C O1W 0.84 1.75 2.573(2) 165.6 . yes
O1W H1WA O12 0.87 1.88 2.748(2) 172.0 2_565 yes
O1W H1WB O12 0.87 1.89 2.759(2) 174.2 3_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 N1C -77.2(2) . . . . ?
C2 C3 N1C C2C -74.8(3) . . . . ?
C2 C3 N1C C6C 101.2(2) . . . . ?
C3 N1C C2C C3C 170.7(2) . . . . ?
C3 N1C C2C C21C -10.3(3) . . . . ?
C3 N1C C6C C5C -172.4(2) . . . . ?
O11 S1 C2 C3 176.99(16) . . . . ?
O12 S1 C2 C3 -63.75(19) . . . . ?
O13 S1 C2 C3 54.35(19) . . . . ?
N1C C2C C3C C4C 1.6(3) . . . . ?
N1C C2C C3C O31C -177.5(2) . . . . ?
C2C N1C C6C C5C 3.5(3) . . . . ?
C2C C3C C4C C5C 3.6(3) . . . . ?
C2C C3C C4C O41C -177.0(2) . . . . ?
C3C C4C C5C C6C -5.2(3) . . . . ?
C4C C5C C6C N1C 1.8(3) . . . . ?
C6C N1C C2C C3C -5.2(3) . . . . ?
C6C N1C C2C C21C 173.8(2) . . . . ?
C21C C2C C3C C4C -177.4(2) . . . . ?
C21C C2C C3C O31C 3.5(3) . . . . ?
O31C C3C C4C C5C -177.4(2) . . . . ?
O31C C3C C4C O41C 2.1(3) . . . . ?
O41C C4C C5C C6C 175.4(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.83(2)
2 0.17(2)

####################################################################### 
# 
# 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_32108202_0m
_database_code_depnum_ccdc_archive 'CCDC 2505174'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2025-11-24 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 Cu N6 O4, 2(Cl), 4(H2 O)'
_chemical_formula_sum            'C22 H34 Cl2 Cu N6 O8'
_chemical_formula_weight         644.99
_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'
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'
Cu Cu 0.3201 1.2651 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1875(5)
_cell_length_b                   8.7569(5)
_cell_length_c                   9.8704(6)
_cell_angle_alpha                94.856(2)
_cell_angle_beta                 103.393(2)
_cell_angle_gamma                103.024(2)
_cell_volume                     663.69(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  0.4920
_exptl_absorpt_correction_T_min  0.4033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1357 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.8197.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             335
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.123
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31377
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3273
_reflns_number_total             3289
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.087
_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)+(0.0267P)²+0.3749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Me refined with riding coordinates:
 C21(H21A,H21B,H21C)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C12(H12)
;
_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
Cu1 Cu 0.000000 0.500000 0.000000 0.00780(6) Uani 1 2 d S . P . .
Cl1 Cl 0.79650(4) 0.94914(3) 0.73579(3) 0.01408(7) Uani 1 1 d . . . . .
O41 O -0.16659(10) 0.50818(9) 0.11251(8) 0.00977(15) Uani 1 1 d . . . . .
O31 O 0.17704(10) 0.57644(9) 0.17584(8) 0.00956(15) Uani 1 1 d . . . . .
O1W O -0.03592(13) 0.19672(11) 0.02943(11) 0.01948(19) Uani 1 1 d . . . . .
H1WA H 0.030(3) 0.155(3) 0.092(2) 0.040(6) Uiso 1 1 d . . . . .
H1WB H -0.079(3) 0.125(3) -0.050(3) 0.048(6) Uiso 1 1 d . . . . .
O2W O 0.40333(11) 0.39420(11) 0.22339(9) 0.01402(17) Uani 1 1 d . . . . .
H2WA H 0.349(3) 0.315(2) 0.243(2) 0.026(5) Uiso 1 1 d . . . . .
H2WB H 0.333(3) 0.448(3) 0.206(2) 0.038(6) Uiso 1 1 d . . . . .
N1 N 0.10935(12) 0.71257(11) 0.51039(9) 0.00926(17) Uani 1 1 d . . . . .
C2 C 0.19700(14) 0.68026(12) 0.41206(11) 0.00892(19) Uani 1 1 d . . . . .
C21 C 0.39103(14) 0.71841(14) 0.45346(12) 0.0129(2) Uani 1 1 d . . . . .
H21A H 0.432644 0.688406 0.372156 0.019 Uiso 1 1 calc R U . . .
H21B H 0.437800 0.832307 0.485716 0.019 Uiso 1 1 calc R U . . .
H21C H 0.429723 0.659505 0.529610 0.019 Uiso 1 1 calc R U . . .
C3 C 0.10247(14) 0.61016(12) 0.27715(11) 0.00813(19) Uani 1 1 d . . . . .
C4 C -0.08369(14) 0.57158(12) 0.24059(11) 0.00841(19) Uani 1 1 d . . . . .
C5 C -0.16581(14) 0.60589(13) 0.34588(11) 0.0102(2) Uani 1 1 d . . . . .
H5 H -0.288848 0.579984 0.325931 0.012 Uiso 1 1 calc R U . . .
C6 C -0.06646(15) 0.67711(13) 0.47760(11) 0.0105(2) Uani 1 1 d . . . . .
H6 H -0.122392 0.702216 0.547659 0.013 Uiso 1 1 calc R U . . .
C7 C 0.20489(15) 0.79830(13) 0.65190(11) 0.0110(2) Uani 1 1 d . . . . .
H7A H 0.317798 0.771333 0.681228 0.013 Uiso 1 1 calc R U . . .
H7B H 0.137449 0.766207 0.720633 0.013 Uiso 1 1 calc R U . . .
C8 C 0.23500(15) 0.97734(13) 0.64969(11) 0.0114(2) Uani 1 1 d . . . . .
H8A H 0.294605 1.006416 0.575515 0.014 Uiso 1 1 calc R U . . .
H8B H 0.121120 1.003246 0.624598 0.014 Uiso 1 1 calc R U . . .
N13 N 0.51829(13) 1.09657(11) 0.83708(10) 0.01116(18) Uani 1 1 d . . . . .
C9 C 0.34009(14) 1.07431(12) 0.78627(11) 0.0095(2) Uani 1 1 d . . . . .
C10 C 0.29209(15) 1.16434(13) 0.88140(12) 0.0119(2) Uani 1 1 d . . . . .
H10 H 0.177558 1.173270 0.877120 0.014 Uiso 1 1 calc R U . . .
N11 N 0.43921(13) 1.24037(11) 0.98516(10) 0.01274(19) Uani 1 1 d . . . . .
C12 C 0.57431(15) 1.19829(13) 0.95661(12) 0.0130(2) Uani 1 1 d . . . . .
H12 H 0.691039 1.234230 1.011642 0.016 Uiso 1 1 calc R U . . .
H13 H 0.587(2) 1.057(2) 0.8021(19) 0.022(4) Uiso 1 1 d . . . . .
H11 H 0.442(2) 1.302(2) 1.059(2) 0.026(4) Uiso 1 1 d . . . . .


_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
Cu1 O41 1.9573(8) 2_565 ?
Cu1 O41 1.9573(8) . ?
Cu1 O31 1.9396(8) . ?
Cu1 O31 1.9396(8) 2_565 ?
O41 C4 1.2965(13) . ?
O31 C3 1.3320(13) . ?
O1W H1WA 0.89(2) . ?
O1W H1WB 0.91(2) . ?
O2W H2WA 0.79(2) . ?
O2W H2WB 0.82(2) . ?
N1 C2 1.3801(14) . ?
N1 C6 1.3561(15) . ?
N1 C7 1.4758(13) . ?
C2 C21 1.4964(15) . ?
C2 C3 1.3853(14) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C3 C4 1.4353(15) . ?
C4 C5 1.4087(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3730(15) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5340(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.4894(15) . ?
N13 C9 1.3909(14) . ?
N13 C12 1.3353(14) . ?
N13 H13 0.849(19) . ?
C9 C10 1.3575(15) . ?
C10 H10 0.9500 . ?
C10 N11 1.3765(15) . ?
N11 C12 1.3225(16) . ?
N11 H11 0.862(19) . ?
C12 H12 0.9500 . ?

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
O41 Cu1 O41 180.0 2_565 . ?
O31 Cu1 O41 85.73(3) . . ?
O31 Cu1 O41 85.73(3) 2_565 2_565 ?
O31 Cu1 O41 94.27(3) 2_565 . ?
O31 Cu1 O41 94.27(3) . 2_565 ?
O31 Cu1 O31 180.0 . 2_565 ?
C4 O41 Cu1 109.40(7) . . ?
C3 O31 Cu1 109.29(6) . . ?
H1WA O1W H1WB 107(2) . . ?
H2WA O2W H2WB 104(2) . . ?
C2 N1 C7 120.68(9) . . ?
C6 N1 C2 121.42(9) . . ?
C6 N1 C7 117.73(9) . . ?
N1 C2 C21 119.68(9) . . ?
N1 C2 C3 118.95(10) . . ?
C3 C2 C21 121.35(10) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O31 C3 C2 122.71(10) . . ?
O31 C3 C4 116.89(9) . . ?
C2 C3 C4 120.40(10) . . ?
O41 C4 C3 118.21(10) . . ?
O41 C4 C5 123.77(10) . . ?
C5 C4 C3 118.02(10) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.41(10) . . ?
C6 C5 H5 120.3 . . ?
N1 C6 C5 121.77(10) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.65(9) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.55(9) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C9 N13 H13 129.2(12) . . ?
C12 N13 C9 109.24(10) . . ?
C12 N13 H13 121.6(12) . . ?
N13 C9 C8 124.25(10) . . ?
C10 C9 C8 129.93(10) . . ?
C10 C9 N13 105.72(10) . . ?
C9 C10 H10 126.2 . . ?
C9 C10 N11 107.70(10) . . ?
N11 C10 H10 126.2 . . ?
C10 N11 H11 125.1(13) . . ?
C12 N11 C10 109.13(10) . . ?
C12 N11 H11 125.7(13) . . ?
N13 C12 H12 125.9 . . ?
N11 C12 N13 108.20(10) . . ?
N11 C12 H12 125.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA Cl1 0.89(2) 2.33(2) 3.2202(10) 177.9(19) 2_666 yes
O1W H1WB Cl1 0.91(2) 2.37(2) 3.2767(10) 176(2) 1_444 yes
O2W H2WA Cl1 0.79(2) 2.41(2) 3.1894(10) 168.5(18) 2_666 yes
O2W H2WB O31 0.82(2) 1.88(2) 2.6937(12) 177(2) . yes
C21 H21C O2W 0.98 2.64 3.5740(15) 159.3 2_666 yes
C5 H5 O2W 0.95 2.59 3.4698(14) 153.9 1_455 yes
C10 H10 O1W 0.95 2.59 3.3939(15) 143.2 1_566 yes
C12 H12 O41 0.95 2.43 3.0689(14) 124.5 1_666 yes
C12 H12 O1W 0.95 2.30 3.1081(15) 142.4 1_666 yes
N13 H13 Cl1 0.849(19) 2.322(19) 3.1650(10) 172.6(16) . yes
N11 H11 O2W 0.862(19) 1.88(2) 2.7189(13) 165.6(18) 1_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O41 C4 C3 -4.54(11) . . . . ?
Cu1 O41 C4 C5 175.00(8) . . . . ?
Cu1 O31 C3 C2 -174.23(8) . . . . ?
Cu1 O31 C3 C4 5.29(11) . . . . ?
O41 C4 C5 C6 -178.25(10) . . . . ?
O31 C3 C4 O41 -0.50(14) . . . . ?
O31 C3 C4 C5 179.94(9) . . . . ?
N1 C2 C3 O31 179.37(9) . . . . ?
N1 C2 C3 C4 -0.13(15) . . . . ?
N1 C7 C8 C9 -176.54(9) . . . . ?
C2 N1 C6 C5 0.75(16) . . . . ?
C2 N1 C7 C8 87.75(12) . . . . ?
C2 C3 C4 O41 179.03(9) . . . . ?
C2 C3 C4 C5 -0.53(15) . . . . ?
C21 C2 C3 O31 -1.80(16) . . . . ?
C21 C2 C3 C4 178.69(10) . . . . ?
C3 C4 C5 C6 1.28(15) . . . . ?
C4 C5 C6 N1 -1.42(16) . . . . ?
C6 N1 C2 C21 -178.80(10) . . . . ?
C6 N1 C2 C3 0.05(15) . . . . ?
C6 N1 C7 C8 -87.67(11) . . . . ?
C7 N1 C2 C21 5.94(15) . . . . ?
C7 N1 C2 C3 -175.21(9) . . . . ?
C7 N1 C6 C5 176.14(10) . . . . ?
C7 C8 C9 N13 74.23(14) . . . . ?
C7 C8 C9 C10 -110.01(13) . . . . ?
C8 C9 C10 N11 -175.40(11) . . . . ?
N13 C9 C10 N11 0.96(12) . . . . ?
C9 N13 C12 N11 0.76(13) . . . . ?
C9 C10 N11 C12 -0.53(13) . . . . ?
C10 N11 C12 N13 -0.15(13) . . . . ?
C12 N13 C9 C8 175.55(10) . . . . ?
C12 N13 C9 C10 -1.07(12) . . . . ?

_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_32108201_0m
_database_code_depnum_ccdc_archive 'CCDC 2505172'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2025-11-24 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.667(Cl), H2 O, 0.667(C11 H14 N3 O2)'
_chemical_formula_sum            'C7.33 H11.33 Cl0.67 N2 O2.33'
_chemical_formula_weight         188.48
_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'
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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   51.723(3)
_cell_length_b                   7.3982(4)
_cell_length_c                   13.4262(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.297(2)
_cell_angle_gamma                90
_cell_volume                     5096.1(5)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    9672
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.7491.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.062
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       68
_diffrn_reflns_limit_h_min       -68
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            53532
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         2.382
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5887
_reflns_number_total             6331
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+8.4208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C8A(H8AA,H8AB), C7B(H7BA,H7BB), C8B(H8BA,H8BB)
2.b Me refined with riding coordinates:
 C21A(H21A,H21B,H21C), C21B(H21D,H21E,H21F)
2.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C10A(H10A), C12A(H12A), C5B(H5B), C6B(H6B), C10B(H10B),
 C12B(H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.67092(2) 1.18834(5) 0.17442(3) 0.01577(9) Uani 1 1 d . . . . .
Cl2 Cl 0.70095(2) 1.23993(5) 0.57377(3) 0.01441(9) Uani 1 1 d . . . . .
O1W O 0.71466(2) 1.16276(16) 0.35669(9) 0.0185(2) Uani 1 1 d . . . . .
H1WA H 0.7096(5) 1.182(3) 0.410(2) 0.035(6) Uiso 1 1 d . . . . .
H1WB H 0.7027(5) 1.172(4) 0.316(2) 0.038(7) Uiso 1 1 d . . . . .
O2W O 0.41729(2) 0.25253(16) 0.39229(10) 0.0202(2) Uani 1 1 d . . . . .
H2WA H 0.4222(5) 0.227(3) 0.337(2) 0.037(7) Uiso 1 1 d . . . . .
H2WB H 0.4265(5) 0.216(4) 0.439(2) 0.038(7) Uiso 1 1 d . . . . .
O3W O 0.56327(2) 0.19314(17) 0.28949(9) 0.0188(2) Uani 1 1 d . . . . .
H3WA H 0.5672(4) 0.280(3) 0.3161(17) 0.024(6) Uiso 1 1 d . . . . .
H3WB H 0.5629(5) 0.114(4) 0.330(2) 0.048(8) Uiso 1 1 d . . . . .
O31A O 0.59851(2) 0.86591(15) 0.38522(8) 0.0158(2) Uani 1 1 d . . . . .
H31A H 0.5832(4) 0.840(3) 0.3958(16) 0.024(5) Uiso 1 1 d . . . . .
O41A O 0.57941(2) 0.51842(14) 0.36711(8) 0.0147(2) Uani 1 1 d . . . . .
N1A N 0.65800(2) 0.60858(17) 0.40119(9) 0.0123(2) Uani 1 1 d . . . . .
C2A C 0.64134(3) 0.75378(19) 0.39846(10) 0.0120(3) Uani 1 1 d . . . . .
C21A C 0.65204(3) 0.9417(2) 0.40757(12) 0.0163(3) Uani 1 1 d . . . . .
H21A H 0.637626 1.028442 0.404193 0.024 Uiso 1 1 calc R U . . .
H21B H 0.663142 0.954831 0.471954 0.024 Uiso 1 1 calc R U . . .
H21C H 0.662350 0.965094 0.352545 0.024 Uiso 1 1 calc R U . . .
C3A C 0.61484(3) 0.72154(19) 0.38668(10) 0.0113(3) Uani 1 1 d . . . . .
C4A C 0.60409(3) 0.54303(19) 0.37504(10) 0.0113(3) Uani 1 1 d . . . . .
C5A C 0.62251(3) 0.4017(2) 0.37252(11) 0.0139(3) Uani 1 1 d . . . . .
H5A H 0.616642 0.281051 0.360525 0.017 Uiso 1 1 calc R U . . .
C6A C 0.64867(3) 0.4377(2) 0.38722(11) 0.0138(3) Uani 1 1 d . . . . .
H6A H 0.660649 0.340302 0.387658 0.017 Uiso 1 1 calc R U . . .
C7A C 0.68659(3) 0.6335(2) 0.42100(11) 0.0135(3) Uani 1 1 d . . . . .
H7AA H 0.694465 0.527679 0.458511 0.016 Uiso 1 1 calc R U . . .
H7AB H 0.690490 0.742008 0.463383 0.016 Uiso 1 1 calc R U . . .
C8A C 0.69874(3) 0.6551(2) 0.32365(11) 0.0159(3) Uani 1 1 d . . . . .
H8AA H 0.694543 0.547863 0.280544 0.019 Uiso 1 1 calc R U . . .
H8AB H 0.691208 0.762676 0.286858 0.019 Uiso 1 1 calc R U . . .
C9A C 0.72772(3) 0.6760(2) 0.34454(11) 0.0139(3) Uani 1 1 d . . . . .
C10A C 0.74717(3) 0.5504(2) 0.35664(11) 0.0159(3) Uani 1 1 d . . . . .
H10A H 0.745151 0.422767 0.354922 0.019 Uiso 1 1 calc R U . . .
C12A C 0.76550(3) 0.8211(2) 0.36988(11) 0.0166(3) Uani 1 1 d . . . . .
H12A H 0.778175 0.914647 0.377680 0.020 Uiso 1 1 calc R U . . .
N13A N 0.73970(2) 0.84384(18) 0.35500(9) 0.0152(2) Uani 1 1 d . . . . .
H13A H 0.7318(4) 0.955(3) 0.3578(17) 0.033(6) Uiso 1 1 d . . . . .
N11A N 0.77036(2) 0.64489(19) 0.37188(9) 0.0160(3) Uani 1 1 d . . . . .
H11A H 0.7857(5) 0.596(3) 0.3798(16) 0.031(6) Uiso 1 1 d . . . . .
O31B O 0.53060(2) 0.53761(16) 0.40452(10) 0.0227(3) Uani 1 1 d . . . . .
H31B H 0.5446(5) 0.559(3) 0.3944(17) 0.030(6) Uiso 1 1 d . . . . .
O41B O 0.55032(2) 0.88295(16) 0.42573(9) 0.0196(2) Uani 1 1 d . . . . .
N1B N 0.47183(2) 0.80124(17) 0.35419(9) 0.0123(2) Uani 1 1 d . . . . .
C2B C 0.48818(3) 0.6547(2) 0.36884(11) 0.0133(3) Uani 1 1 d . . . . .
C21B C 0.47725(3) 0.4679(2) 0.35566(15) 0.0236(4) Uani 1 1 d . . . . .
H21D H 0.491376 0.379505 0.368775 0.035 Uiso 1 1 calc R U . . .
H21E H 0.464522 0.448620 0.402828 0.035 Uiso 1 1 calc R U . . .
H21F H 0.468670 0.453236 0.286749 0.035 Uiso 1 1 calc R U . . .
C3B C 0.51462(3) 0.6840(2) 0.39142(11) 0.0132(3) Uani 1 1 d . . . . .
C4B C 0.52575(3) 0.8610(2) 0.40209(10) 0.0129(3) Uani 1 1 d . . . . .
C5B C 0.50774(3) 1.0046(2) 0.38337(13) 0.0198(3) Uani 1 1 d . . . . .
H5B H 0.513864 1.125728 0.386520 0.024 Uiso 1 1 calc R U . . .
C6B C 0.48164(3) 0.9717(2) 0.36083(12) 0.0176(3) Uani 1 1 d . . . . .
H6B H 0.470014 1.071093 0.349451 0.021 Uiso 1 1 calc R U . . .
C7B C 0.44320(3) 0.7774(2) 0.33056(11) 0.0138(3) Uani 1 1 d . . . . .
H7BA H 0.439578 0.667241 0.289274 0.017 Uiso 1 1 calc R U . . .
H7BB H 0.435782 0.881998 0.290724 0.017 Uiso 1 1 calc R U . . .
C8B C 0.42997(3) 0.7610(2) 0.42613(10) 0.0119(3) Uani 1 1 d . . . . .
H8BA H 0.437317 0.655771 0.465626 0.014 Uiso 1 1 calc R U . . .
H8BB H 0.433770 0.870634 0.467674 0.014 Uiso 1 1 calc R U . . .
N13B N 0.38929(2) 0.57093(18) 0.38584(9) 0.0133(2) Uani 1 1 d . . . . .
H13B H 0.3971(4) 0.464(3) 0.3877(15) 0.019(5) Uiso 1 1 d . . . . .
N11B N 0.35832(2) 0.7668(2) 0.37644(10) 0.0170(3) Uani 1 1 d . . . . .
H11B H 0.3434(5) 0.809(4) 0.3744(19) 0.042(7) Uiso 1 1 d . . . . .
C9B C 0.40106(3) 0.73854(19) 0.40308(10) 0.0112(3) Uani 1 1 d . . . . .
C10B C 0.38130(3) 0.8621(2) 0.39604(11) 0.0146(3) Uani 1 1 d . . . . .
H10B H 0.383050 0.989459 0.403258 0.018 Uiso 1 1 calc R U . . .
C12B C 0.36344(3) 0.5912(2) 0.37125(11) 0.0165(3) Uani 1 1 d . . . . .
H12B H 0.350942 0.496998 0.359306 0.020 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
O1W H1WA 0.81(3) . ?
O1W H1WB 0.77(3) . ?
O2W H2WA 0.84(3) . ?
O2W H2WB 0.79(3) . ?
O3W H3WA 0.75(2) . ?
O3W H3WB 0.80(3) . ?
O31A H31A 0.85(2) . ?
O31A C3A 1.3602(17) . ?
O41A C4A 1.2803(17) . ?
N1A C2A 1.3747(18) . ?
N1A C6A 1.3575(19) . ?
N1A C7A 1.4804(17) . ?
C2A C21A 1.496(2) . ?
C2A C3A 1.3804(19) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C3A C4A 1.4338(19) . ?
C4A C5A 1.4178(19) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.369(2) . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.529(2) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.4974(19) . ?
C9A C10A 1.364(2) . ?
C9A N13A 1.387(2) . ?
C10A H10A 0.9500 . ?
C10A N11A 1.3812(19) . ?
C12A H12A 0.9500 . ?
C12A N13A 1.3350(19) . ?
C12A N11A 1.327(2) . ?
N13A H13A 0.92(2) . ?
N11A H11A 0.86(2) . ?
O31B H31B 0.77(2) . ?
O31B C3B 1.3600(18) . ?
O41B C4B 1.2806(17) . ?
N1B C2B 1.3739(19) . ?
N1B C6B 1.358(2) . ?
N1B C7B 1.4850(17) . ?
C2B C21B 1.495(2) . ?
C2B C3B 1.3799(19) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C3B C4B 1.430(2) . ?
C4B C5B 1.414(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.367(2) . ?
C6B H6B 0.9500 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.5338(19) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.4974(18) . ?
N13B H13B 0.88(2) . ?
N13B C9B 1.3877(18) . ?
N13B C12B 1.3351(19) . ?
N11B H11B 0.83(3) . ?
N11B C10B 1.3783(19) . ?
N11B C12B 1.330(2) . ?
C9B C10B 1.366(2) . ?
C10B H10B 0.9500 . ?
C12B H12B 0.9500 . ?

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
H1WA O1W H1WB 107(2) . . ?
H2WA O2W H2WB 115(3) . . ?
H3WA O3W H3WB 109(3) . . ?
C3A O31A H31A 114.4(15) . . ?
C2A N1A C7A 121.07(12) . . ?
C6A N1A C2A 120.89(12) . . ?
C6A N1A C7A 118.04(12) . . ?
N1A C2A C21A 120.00(12) . . ?
N1A C2A C3A 118.55(13) . . ?
C3A C2A C21A 121.44(13) . . ?
C2A C21A H21A 109.5 . . ?
C2A C21A H21B 109.5 . . ?
C2A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
O31A C3A C2A 118.14(13) . . ?
O31A C3A C4A 119.35(12) . . ?
C2A C3A C4A 122.50(13) . . ?
O41A C4A C3A 120.58(13) . . ?
O41A C4A C5A 123.99(13) . . ?
C5A C4A C3A 115.42(12) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A C4A 120.54(13) . . ?
C6A C5A H5A 119.7 . . ?
N1A C6A C5A 121.92(13) . . ?
N1A C6A H6A 119.0 . . ?
C5A C6A H6A 119.0 . . ?
N1A C7A H7AA 109.3 . . ?
N1A C7A H7AB 109.3 . . ?
N1A C7A C8A 111.67(11) . . ?
H7AA C7A H7AB 107.9 . . ?
C8A C7A H7AA 109.3 . . ?
C8A C7A H7AB 109.3 . . ?
C7A C8A H8AA 109.4 . . ?
C7A C8A H8AB 109.4 . . ?
H8AA C8A H8AB 108.0 . . ?
C9A C8A C7A 111.18(12) . . ?
C9A C8A H8AA 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
C10A C9A C8A 131.14(15) . . ?
C10A C9A N13A 106.55(13) . . ?
N13A C9A C8A 122.31(13) . . ?
C9A C10A H10A 126.7 . . ?
C9A C10A N11A 106.65(14) . . ?
N11A C10A H10A 126.7 . . ?
N13A C12A H12A 126.0 . . ?
N11A C12A H12A 126.0 . . ?
N11A C12A N13A 108.08(14) . . ?
C9A N13A H13A 127.5(15) . . ?
C12A N13A C9A 109.10(13) . . ?
C12A N13A H13A 123.1(15) . . ?
C10A N11A H11A 124.8(16) . . ?
C12A N11A C10A 109.59(13) . . ?
C12A N11A H11A 125.6(16) . . ?
C3B O31B H31B 112.4(18) . . ?
C2B N1B C7B 121.04(12) . . ?
C6B N1B C2B 120.37(12) . . ?
C6B N1B C7B 118.58(12) . . ?
N1B C2B C21B 119.73(13) . . ?
N1B C2B C3B 118.83(13) . . ?
C3B C2B C21B 121.39(13) . . ?
C2B C21B H21D 109.5 . . ?
C2B C21B H21E 109.5 . . ?
C2B C21B H21F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
O31B C3B C2B 118.18(13) . . ?
O31B C3B C4B 119.07(12) . . ?
C2B C3B C4B 122.75(13) . . ?
O41B C4B C3B 121.00(13) . . ?
O41B C4B C5B 124.02(14) . . ?
C5B C4B C3B 114.97(13) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B C4B 121.03(14) . . ?
C6B C5B H5B 119.5 . . ?
N1B C6B C5B 122.00(14) . . ?
N1B C6B H6B 119.0 . . ?
C5B C6B H6B 119.0 . . ?
N1B C7B H7BA 109.3 . . ?
N1B C7B H7BB 109.3 . . ?
N1B C7B C8B 111.68(11) . . ?
H7BA C7B H7BB 107.9 . . ?
C8B C7B H7BA 109.3 . . ?
C8B C7B H7BB 109.3 . . ?
C7B C8B H8BA 109.2 . . ?
C7B C8B H8BB 109.2 . . ?
H8BA C8B H8BB 107.9 . . ?
C9B C8B C7B 112.08(11) . . ?
C9B C8B H8BA 109.2 . . ?
C9B C8B H8BB 109.2 . . ?
C9B N13B H13B 127.0(13) . . ?
C12B N13B H13B 123.4(13) . . ?
C12B N13B C9B 109.52(13) . . ?
C10B N11B H11B 126.3(19) . . ?
C12B N11B H11B 123.6(19) . . ?
C12B N11B C10B 109.74(13) . . ?
N13B C9B C8B 122.61(13) . . ?
C10B C9B C8B 131.23(13) . . ?
C10B C9B N13B 106.15(12) . . ?
N11B C10B H10B 126.6 . . ?
C9B C10B N11B 106.86(13) . . ?
C9B C10B H10B 126.6 . . ?
N13B C12B H12B 126.1 . . ?
N11B C12B N13B 107.71(13) . . ?
N11B C12B H12B 126.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA Cl2 0.81(3) 2.34(3) 3.1384(13) 172(2) . yes
O1W H1WB Cl1 0.77(3) 2.36(3) 3.1205(13) 171(2) . yes
O2W H2WA O3W 0.84(3) 1.95(3) 2.7900(18) 173(3) 2_655 yes
O2W H2WB O41B 0.79(3) 2.17(3) 2.9565(18) 176(3) 5_666 yes
O3W H3WA O41A 0.75(2) 1.96(3) 2.7117(16) 172(2) . yes
O3W H3WB O31A 0.80(3) 2.64(3) 3.2000(16) 128(2) 1_545 yes
O3W H3WB O41B 0.80(3) 2.28(3) 3.0613(18) 164(3) 1_545 yes
O31A H31A O41B 0.85(2) 1.82(2) 2.6207(15) 157(2) . yes
C21A H21B Cl1 0.98 2.90 3.7185(16) 141.9 6_576 yes
C21A H21C Cl1 0.98 2.99 3.8545(16) 148.4 . yes
C7A H7AA Cl2 0.99 2.63 3.5845(15) 162.4 1_545 yes
C8A H8AB Cl2 0.99 2.97 3.4596(15) 111.8 6_575 yes
C10A H10A O1W 0.95 2.49 3.324(2) 146.7 1_545 yes
C12A H12A Cl2 0.95 2.82 3.7147(16) 157.7 7_676 yes
N13A H13A O1W 0.92(2) 1.77(3) 2.6928(18) 176(2) . yes
N11A H11A Cl1 0.86(2) 2.54(2) 3.1928(13) 133(2) 4_645 yes
N11A H11A Cl2 0.86(2) 2.63(2) 3.2504(14) 129.4(19) 7_666 yes
O31B H31B O41A 0.77(2) 1.91(2) 2.6396(16) 159(2) . yes
C21B H21E O31B 0.98 2.57 3.296(2) 131.1 5_666 yes
C21B H21F O3W 0.98 2.66 3.359(2) 129.0 2_655 yes
C21B H21F O31B 0.98 2.65 3.503(2) 146.0 2_655 yes
C6B H6B O3W 0.95 2.54 3.3109(19) 138.6 2_665 yes
C7B H7BA O41A 0.99 2.46 3.3606(18) 150.7 2_655 yes
C7B H7BB O3W 0.99 2.54 3.469(2) 155.3 2_665 yes
C8B H8BB O41B 0.99 2.40 3.3793(18) 171.1 5_676 yes
N13B H13B O2W 0.88(2) 1.88(2) 2.7607(18) 173.5(19) . yes
N11B H11B Cl1 0.83(3) 2.96(3) 3.4953(15) 125(2) 2_655 yes
N11B H11B Cl2 0.83(3) 2.51(3) 3.2199(13) 145(2) 5_676 yes
C10B H10B O2W 0.95 2.65 3.440(2) 141.2 1_565 yes
C12B H12B Cl1 0.95 2.56 3.4840(16) 163.5 2_645 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O31A C3A C4A O41A -2.6(2) . . . . ?
O31A C3A C4A C5A 176.99(12) . . . . ?
O41A C4A C5A C6A -176.25(13) . . . . ?
N1A C2A C3A O31A 179.26(12) . . . . ?
N1A C2A C3A C4A -1.4(2) . . . . ?
N1A C7A C8A C9A -178.70(12) . . . . ?
C2A N1A C6A C5A -1.7(2) . . . . ?
C2A N1A C7A C8A -92.10(16) . . . . ?
C2A C3A C4A O41A 178.04(13) . . . . ?
C2A C3A C4A C5A -2.3(2) . . . . ?
C21A C2A C3A O31A -1.1(2) . . . . ?
C21A C2A C3A C4A 178.26(13) . . . . ?
C3A C4A C5A C6A 4.1(2) . . . . ?
C4A C5A C6A N1A -2.3(2) . . . . ?
C6A N1A C2A C21A -176.15(13) . . . . ?
C6A N1A C2A C3A 3.5(2) . . . . ?
C6A N1A C7A C8A 88.84(16) . . . . ?
C7A N1A C2A C21A 4.8(2) . . . . ?
C7A N1A C2A C3A -175.52(12) . . . . ?
C7A N1A C6A C5A 177.33(13) . . . . ?
C7A C8A C9A C10A 87.2(2) . . . . ?
C7A C8A C9A N13A -92.98(17) . . . . ?
C8A C9A C10A N11A 178.52(14) . . . . ?
C8A C9A N13A C12A -178.03(13) . . . . ?
C9A C10A N11A C12A 0.34(17) . . . . ?
C10A C9A N13A C12A 1.80(16) . . . . ?
N13A C9A C10A N11A -1.28(16) . . . . ?
N13A C12A N11A C10A 0.78(17) . . . . ?
N11A C12A N13A C9A -1.60(17) . . . . ?
O31B C3B C4B O41B -1.5(2) . . . . ?
O31B C3B C4B C5B 177.71(14) . . . . ?
O41B C4B C5B C6B -178.39(15) . . . . ?
N1B C2B C3B O31B -179.22(13) . . . . ?
N1B C2B C3B C4B 1.2(2) . . . . ?
N1B C7B C8B C9B 179.49(12) . . . . ?
C2B N1B C6B C5B -0.9(2) . . . . ?
C2B N1B C7B C8B 87.06(16) . . . . ?
C2B C3B C4B O41B 178.12(14) . . . . ?
C2B C3B C4B C5B -2.7(2) . . . . ?
C21B C2B C3B O31B -2.0(2) . . . . ?
C21B C2B C3B C4B 178.44(14) . . . . ?
C3B C4B C5B C6B 2.4(2) . . . . ?
C4B C5B C6B N1B -0.8(3) . . . . ?
C6B N1B C2B C21B -176.60(15) . . . . ?
C6B N1B C2B C3B 0.7(2) . . . . ?
C6B N1B C7B C8B -93.14(16) . . . . ?
C7B N1B C2B C21B 3.2(2) . . . . ?
C7B N1B C2B C3B -179.49(12) . . . . ?
C7B N1B C6B C5B 179.27(14) . . . . ?
C7B C8B C9B N13B 87.17(16) . . . . ?
C7B C8B C9B C10B -94.18(18) . . . . ?
C8B C9B C10B N11B -177.93(14) . . . . ?
N13B C9B C10B N11B 0.88(16) . . . . ?
C9B N13B C12B N11B 1.33(17) . . . . ?
C10B N11B C12B N13B -0.77(17) . . . . ?
C12B N13B C9B C8B 177.55(12) . . . . ?
C12B N13B C9B C10B -1.38(16) . . . . ?
C12B N11B C10B C9B -0.10(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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2505173'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2025-11-24 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
miquel.barcelo@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N3 O4, 2(H2 O)'
_chemical_formula_sum            'C12 H17 N3 O6'
_chemical_formula_weight         299.28
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0597(9)
_cell_length_b                   8.8765(11)
_cell_length_c                   11.2263(14)
_cell_angle_alpha                89.195(4)
_cell_angle_beta                 88.506(4)
_cell_angle_gamma                68.574(4)
_cell_volume                     654.65(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      6.64
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1704 before and 0.0887 after correction.
The Ratio of minimum to maximum transmission is 0.7279.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from water by slow evaporation'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23230
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.453
_diffrn_reflns_theta_min         5.353
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2353
_reflns_number_total             2386
_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       'Bruker Apex4, 2021'
_computing_data_collection       'Bruker Apex4, 2021'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.137
_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)+(0.0831P)²+0.4008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1405
_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) 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:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 N13(H13), C12(H12), N11(H11), C10(H10), C5(H5), C6(H6)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O31(H31)
;
_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
C71 C 0.4837(3) 0.8564(2) 0.72744(15) 0.0142(4) Uani 1 1 d . . . . .
C7 C 0.7060(3) 0.7923(2) 0.67936(15) 0.0144(4) Uani 1 1 d . . . . .
H7 H 0.795379 0.727913 0.744014 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7696(3) 0.9365(2) 0.64836(15) 0.0153(4) Uani 1 1 d . . . . .
H8A H 0.895162 0.898346 0.598033 0.018 Uiso 1 1 calc R U . . .
H8B H 0.661306 1.016512 0.601416 0.018 Uiso 1 1 calc R U . . .
C9 C 0.8068(3) 1.0175(2) 0.75654(15) 0.0149(4) Uani 1 1 d . . . . .
N13 N 0.9975(2) 1.02101(18) 0.77603(13) 0.0151(4) Uani 1 1 d . . . . .
H13 H 1.106751 0.973607 0.731151 0.018 Uiso 1 1 calc R U . . .
C12 C 0.9904(3) 1.1065(2) 0.87247(15) 0.0168(4) Uani 1 1 d . . . . .
H12 H 1.101338 1.128110 0.904128 0.020 Uiso 1 1 calc R U . . .
N11 N 0.8020(2) 1.15721(18) 0.91775(13) 0.0167(4) Uani 1 1 d . . . . .
H11 H 0.759620 1.215868 0.982497 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6837(3) 1.1032(2) 0.84709(16) 0.0173(4) Uani 1 1 d . . . . .
H10 H 0.543171 1.122000 0.859105 0.021 Uiso 1 1 calc R U . . .
O73 O 0.45446(19) 0.86195(16) 0.83730(11) 0.0187(3) Uani 1 1 d . . . . .
O72 O 0.34720(18) 0.90770(14) 0.64964(11) 0.0157(3) Uani 1 1 d . . . . .
N1 N 0.7283(2) 0.68452(17) 0.57645(13) 0.0140(4) Uani 1 1 d . . . . .
C2 C 0.7372(2) 0.5279(2) 0.59833(15) 0.0145(4) Uani 1 1 d . . . . .
C3 C 0.7522(2) 0.4286(2) 0.50379(16) 0.0145(4) Uani 1 1 d . . . . .
C4 C 0.7606(3) 0.4787(2) 0.38219(15) 0.0155(4) Uani 1 1 d . . . . .
C5 C 0.7420(3) 0.6425(2) 0.36703(15) 0.0159(4) Uani 1 1 d . . . . .
H5 H 0.740167 0.685515 0.288915 0.019 Uiso 1 1 calc R U . . .
C6 C 0.7266(3) 0.7390(2) 0.46301(15) 0.0149(4) Uani 1 1 d . . . . .
H6 H 0.714359 0.848090 0.449905 0.018 Uiso 1 1 calc R U . . .
C21 C 0.7313(3) 0.4700(2) 0.72396(15) 0.0177(4) Uani 1 1 d . . . . .
H21A H 0.855569 0.463939 0.764043 0.027 Uiso 1 1 calc R U . . .
H21B H 0.722041 0.362529 0.723396 0.027 Uiso 1 1 calc R U . . .
H21C H 0.612466 0.545724 0.766559 0.027 Uiso 1 1 calc R U . . .
O31 O 0.76259(19) 0.27392(15) 0.52326(11) 0.0176(3) Uani 1 1 d . . . . .
H31 H 0.737046 0.236318 0.460000 0.026 Uiso 1 1 calc R U . . .
O41 O 0.7818(2) 0.37680(16) 0.30040(11) 0.0199(3) Uani 1 1 d . . . . .
O1W O 0.7561(2) 0.70880(16) 0.99640(11) 0.0216(3) Uani 1 1 d G . . . .
H1WA H 0.759033 0.612525 1.015124 0.032 Uiso 1 1 d G U . . .
H1WB H 0.666940 0.750180 0.941490 0.032 Uiso 1 1 d G U . . .
O2W O 1.1724(2) 0.60934(16) 0.93149(11) 0.0211(3) Uani 1 1 d G . . . .
H2WA H 1.041328 0.637991 0.941851 0.032 Uiso 1 1 d G U . . .
H2WB H 1.190916 0.606257 0.854520 0.032 Uiso 1 1 d G 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
C71 C7 1.546(2) . ?
C71 O73 1.244(2) . ?
C71 O72 1.269(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.536(2) . ?
C7 N1 1.478(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.497(2) . ?
C9 N13 1.381(2) . ?
C9 C10 1.364(3) . ?
N13 H13 0.8800 . ?
N13 C12 1.320(2) . ?
C12 H12 0.9500 . ?
C12 N11 1.328(2) . ?
N11 H11 0.8800 . ?
N11 C10 1.376(2) . ?
C10 H10 0.9500 . ?
N1 C2 1.387(2) . ?
N1 C6 1.355(2) . ?
C2 C3 1.366(3) . ?
C2 C21 1.499(2) . ?
C3 C4 1.436(2) . ?
C3 O31 1.363(2) . ?
C4 C5 1.420(3) . ?
C4 O41 1.265(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.363(2) . ?
C6 H6 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O31 H31 0.8400 . ?
O1W H1WA 0.8702 . ?
O1W H1WB 0.8697 . ?
O2W H2WA 0.8704 . ?
O2W H2WB 0.8699 . ?

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
O73 C71 C7 118.01(15) . . ?
O73 C71 O72 125.95(16) . . ?
O72 C71 C7 115.90(14) . . ?
C71 C7 H7 108.2 . . ?
C8 C7 C71 109.08(13) . . ?
C8 C7 H7 108.2 . . ?
N1 C7 C71 110.49(13) . . ?
N1 C7 H7 108.2 . . ?
N1 C7 C8 112.42(13) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.69(14) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N13 C9 C8 120.37(15) . . ?
C10 C9 C8 133.32(16) . . ?
C10 C9 N13 106.23(15) . . ?
C9 N13 H13 125.3 . . ?
C12 N13 C9 109.41(15) . . ?
C12 N13 H13 125.3 . . ?
N13 C12 H12 125.8 . . ?
N13 C12 N11 108.47(15) . . ?
N11 C12 H12 125.8 . . ?
C12 N11 H11 125.5 . . ?
C12 N11 C10 109.02(15) . . ?
C10 N11 H11 125.5 . . ?
C9 C10 N11 106.85(16) . . ?
C9 C10 H10 126.6 . . ?
N11 C10 H10 126.6 . . ?
C2 N1 C7 118.30(14) . . ?
C6 N1 C7 121.39(14) . . ?
C6 N1 C2 120.17(15) . . ?
N1 C2 C21 120.02(15) . . ?
C3 C2 N1 118.83(15) . . ?
C3 C2 C21 121.15(16) . . ?
C2 C3 C4 122.90(16) . . ?
O31 C3 C2 119.81(15) . . ?
O31 C3 C4 117.28(16) . . ?
C5 C4 C3 114.86(16) . . ?
O41 C4 C3 118.59(16) . . ?
O41 C4 C5 126.56(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.91(16) . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C5 122.22(16) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 O31 H31 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N13 H13 O72 0.88 1.81 2.6764(19) 168.6 1_655 yes
N11 H11 O2W 0.88 2.04 2.753(2) 136.8 2_777 yes
O31 H31 O72 0.84 2.03 2.8366(17) 159.4 2_666 yes
O1W H1WA O2W 0.87 1.94 2.7930(19) 166.9 2_767 yes
O1W H1WB O73 0.87 1.89 2.7548(18) 172.3 . yes
O2W H2WA O1W 0.87 1.96 2.821(2) 169.2 . yes
O2W H2WB O41 0.87 1.76 2.6216(18) 173.7 2_766 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C71 C7 C8 C9 74.02(17) . . . . ?
C71 C7 N1 C2 -77.22(17) . . . . ?
C71 C7 N1 C6 98.45(17) . . . . ?
C7 C8 C9 N13 117.59(16) . . . . ?
C7 C8 C9 C10 -66.0(2) . . . . ?
C7 N1 C2 C3 178.27(14) . . . . ?
C7 N1 C2 C21 -2.0(2) . . . . ?
C7 N1 C6 C5 -178.37(15) . . . . ?
C8 C7 N1 C2 160.66(14) . . . . ?
C8 C7 N1 C6 -23.7(2) . . . . ?
C8 C9 N13 C12 176.36(15) . . . . ?
C8 C9 C10 N11 -176.18(17) . . . . ?
C9 N13 C12 N11 0.88(19) . . . . ?
N13 C9 C10 N11 0.60(19) . . . . ?
N13 C12 N11 C10 -0.49(19) . . . . ?
C12 N11 C10 C9 -0.1(2) . . . . ?
C10 C9 N13 C12 -0.92(19) . . . . ?
O73 C71 C7 C8 -97.76(17) . . . . ?
O73 C71 C7 N1 138.18(15) . . . . ?
O72 C71 C7 C8 78.24(17) . . . . ?
O72 C71 C7 N1 -45.83(19) . . . . ?
N1 C7 C8 C9 -163.06(14) . . . . ?
N1 C2 C3 C4 0.4(3) . . . . ?
N1 C2 C3 O31 179.54(14) . . . . ?
C2 N1 C6 C5 -2.8(2) . . . . ?
C2 C3 C4 C5 -2.9(2) . . . . ?
C2 C3 C4 O41 177.51(15) . . . . ?
C3 C4 C5 C6 2.7(2) . . . . ?
C4 C5 C6 N1 0.0(3) . . . . ?
C6 N1 C2 C3 2.5(2) . . . . ?
C6 N1 C2 C21 -177.77(15) . . . . ?
C21 C2 C3 C4 -179.29(15) . . . . ?
C21 C2 C3 O31 -0.1(2) . . . . ?
O31 C3 C4 C5 177.89(14) . . . . ?
O31 C3 C4 O41 -1.7(2) . . . . ?
O41 C4 C5 C6 -177.76(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
