# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2016348'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

# Clave Lab.  :  ZA9_c
# Clave IF-UAP:  ZA9_c
# Solicitud: 341
# Firma en la Solicitud: Dra. Martha Sosa R. (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\ZA9_c\40mm_1\
# Nota: hidratos = CARMEN 1 (137, P-1) y ZA9_b (250, C2/c) 

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2020-07-14

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Cl2 O4, 2(C8 H6 N2 O2)'
_chemical_formula_sum            'C22 H14 Cl2 N4 O8'
_chemical_formula_weight         533.27
_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7921(5)
_cell_length_b                   11.1245(12)
_cell_length_c                   11.2988(13)
_cell_angle_alpha                65.883(8)
_cell_angle_beta                 86.445(9)
_cell_angle_gamma                78.351(8)
_cell_volume                     538.29(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    12065
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.85

_exptl_crystal_recrystallization_method 
;
Re-cristallisation from solvent: Acetonitrile
;

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.062
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 -7 0.0430
-4 1 8 0.0190
-4 1 0 0.1350
-2 1 -8 0.1930
3 -1 6 0.2050
1 10 4 0.0760
-1 -11 -4 0.0700

_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1157 frames, 50 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            15290
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.659
_diffrn_reflns_theta_max         22.499
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2879
_reflns_number_gt                1984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.52859(8) 0.37846(5) 0.87525(4) 0.04315(13) Uani 1 1 d . . . . .
O1 O 0.3204(2) 0.41633(10) 0.43342(12) 0.0404(3) Uani 1 1 d . . . . .
O2 O 0.3204(2) 0.17092(11) 0.43399(11) 0.0382(3) Uani 1 1 d . . . . .
N1 N 0.6917(3) 0.32450(12) 0.57831(13) 0.0319(3) Uani 1 1 d . . . . .
N2 N 0.6841(3) 0.07859(13) 0.58278(14) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.4949(3) 0.31902(14) 0.50219(15) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.4932(3) 0.18215(14) 0.50370(15) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.8714(3) 0.08705(15) 0.66750(15) 0.0318(3) Uani 1 1 d . . . . .
C4 C 1.0508(4) -0.02603(16) 0.75312(18) 0.0422(4) Uani 1 1 d . . . . .
H4 H 1.050735 -0.110088 0.754274 0.051 Uiso 1 1 calc R U . . .
C5 C 1.2290(4) -0.01275(18) 0.83635(19) 0.0467(4) Uani 1 1 d . . . . .
H5 H 1.345888 -0.088584 0.895234 0.056 Uiso 1 1 calc R U . . .
C6 C 1.2356(4) 0.11281(18) 0.83317(18) 0.0440(4) Uani 1 1 d . . . . .
H6 H 1.358116 0.120709 0.889151 0.053 Uiso 1 1 calc R U . . .
C7 C 1.0610(3) 0.22567(16) 0.74727(17) 0.0360(3) Uani 1 1 d . . . . .
H7 H 1.066973 0.309761 0.744674 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8762(3) 0.21357(14) 0.66456(15) 0.0299(3) Uani 1 1 d . . . . .
O4 O 0.0737(3) 0.61396(14) 0.73596(12) 0.0476(3) Uani 1 1 d . . . . .
O3 O 0.3739(3) 0.29037(13) 1.15084(13) 0.0556(4) Uani 1 1 d . . . . .
C11 C 0.0478(3) 0.55541(16) 0.86264(15) 0.0336(3) Uani 1 1 d . . . . .
C10 C 0.2385(3) 0.44921(15) 0.93915(16) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.2069(3) 0.38654(16) 1.07880(16) 0.0346(3) Uani 1 1 d . . . . .
H1N H 0.701(4) 0.407(2) 0.5737(18) 0.052 Uiso 1 1 d . U . . .
H2N H 0.679(4) -0.002(2) 0.5824(18) 0.052 Uiso 1 1 d . U . . .
H4O H -0.071(4) 0.665(2) 0.704(2) 0.052 Uiso 1 1 d . U . . .


_geom_special_details            ?

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 C10 1.7237(14) . ?
O1 C1 1.2256(18) . ?
O2 C2 1.2349(18) . ?
N1 C1 1.3415(19) . ?
N1 C8 1.3920(19) . ?
N1 H1N 0.91(2) . ?
N2 C2 1.3405(19) . ?
N2 C3 1.395(2) . ?
N2 H2N 0.90(2) . ?
C1 C2 1.517(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.399(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9300 . ?
O4 C11 1.3180(19) . ?
O4 H4O 0.80(2) . ?
O3 C9 1.2128(18) . ?
C11 C10 1.344(2) . ?
C11 C9 1.508(2) 2_567 ?
C10 C9 1.454(2) . ?

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
C1 N1 C8 124.87(13) . . ?
C1 N1 H1N 116.8(12) . . ?
C8 N1 H1N 118.3(12) . . ?
C2 N2 C3 124.71(13) . . ?
C2 N2 H2N 115.5(12) . . ?
C3 N2 H2N 119.7(12) . . ?
O1 C1 N1 124.18(13) . . ?
O1 C1 C2 119.27(13) . . ?
N1 C1 C2 116.55(13) . . ?
O2 C2 N2 123.48(13) . . ?
O2 C2 C1 119.65(13) . . ?
N2 C2 C1 116.87(13) . . ?
C4 C3 N2 121.70(14) . . ?
C4 C3 C8 120.00(15) . . ?
N2 C3 C8 118.31(13) . . ?
C5 C4 C3 119.52(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.64(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.16(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.85(15) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 N1 121.77(13) . . ?
C7 C8 C3 119.81(14) . . ?
N1 C8 C3 118.42(13) . . ?
C11 O4 H4O 110.0(15) . . ?
O4 C11 C10 122.69(14) . . ?
O4 C11 C9 117.25(14) . 2_567 ?
C10 C11 C9 120.06(14) . 2_567 ?
C11 C10 C9 121.82(13) . . ?
C11 C10 Cl1 121.30(12) . . ?
C9 C10 Cl1 116.87(11) . . ?
O3 C9 C10 123.69(14) . . ?
O3 C9 C11 118.19(15) . 2_567 ?
C10 C9 C11 118.12(13) . 2_567 ?

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
C8 N1 C1 O1 174.64(15) . . . . ?
C8 N1 C1 C2 -5.2(2) . . . . ?
C3 N2 C2 O2 -176.45(15) . . . . ?
C3 N2 C2 C1 3.5(2) . . . . ?
O1 C1 C2 O2 1.4(2) . . . . ?
N1 C1 C2 O2 -178.74(14) . . . . ?
O1 C1 C2 N2 -178.52(14) . . . . ?
N1 C1 C2 N2 1.3(2) . . . . ?
C2 N2 C3 C4 175.59(15) . . . . ?
C2 N2 C3 C8 -4.5(2) . . . . ?
N2 C3 C4 C5 -178.98(16) . . . . ?
C8 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 N1 178.55(15) . . . . ?
C6 C7 C8 C3 -1.0(2) . . . . ?
C1 N1 C8 C7 -175.28(14) . . . . ?
C1 N1 C8 C3 4.3(2) . . . . ?
C4 C3 C8 C7 0.1(2) . . . . ?
N2 C3 C8 C7 -179.74(14) . . . . ?
C4 C3 C8 N1 -179.44(14) . . . . ?
N2 C3 C8 N1 0.7(2) . . . . ?
O4 C11 C10 C9 179.66(15) . . . . ?
C9 C11 C10 C9 0.4(2) 2_567 . . . ?
O4 C11 C10 Cl1 -1.9(2) . . . . ?
C9 C11 C10 Cl1 178.83(11) 2_567 . . . ?
C11 C10 C9 O3 179.72(16) . . . . ?
Cl1 C10 C9 O3 1.2(2) . . . . ?
C11 C10 C9 C11 -0.4(2) . . . 2_567 ?
Cl1 C10 C9 C11 -178.89(11) . . . 2_567 ?

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
N1 H1N O1 0.91(2) 1.91(2) 2.8203(16) 174.1(17) 2_666 yes
N2 H2N O2 0.90(2) 1.96(2) 2.8628(17) 175.0(18) 2_656 yes
O4 H4O O1 0.80(2) 2.54(2) 2.9284(17) 111.6(18) 2_566 yes
O4 H4O O2 0.80(2) 2.05(2) 2.8017(17) 156(2) 2_566 yes
O4 H4O O3 0.80(2) 2.27(2) 2.6867(18) 113.4(18) 2_567 yes
N1 H1N O1 0.91(2) 1.91(2) 2.8203(16) 174.1(17) 2_666 yes
N2 H2N O2 0.90(2) 1.96(2) 2.8628(17) 175.0(18) 2_656 yes
O4 H4O O1 0.80(2) 2.54(2) 2.9284(17) 111.6(18) 2_566 yes
O4 H4O O2 0.80(2) 2.05(2) 2.8017(17) 156(2) 2_566 yes
O4 H4O O3 0.80(2) 2.27(2) 2.6867(18) 113.4(18) 2_567 yes

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_III
_database_code_depnum_ccdc_archive 'CCDC 2016352'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

# Clave Lab.  :  ZA-3
# Clave IF-UAP:  ZA3
# Solicitud: 211
# Firma en la Solicitud: Dr. Martha Sosa (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\ZA3\40mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2018-11-29

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 O4, 2(C7 H6 N2 O)'
_chemical_formula_sum            'C20 H16 N4 O6'
_chemical_formula_weight         408.37
_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       ?

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

_cell_length_a                   5.2947(6)
_cell_length_b                   8.1240(7)
_cell_length_c                   20.880(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.109(9)
_cell_angle_gamma                90
_cell_volume                     898.13(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    11441
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.55

_exptl_crystal_recrystallization_method 
;
Re-cristallisation from solvent: Acetonitrile
;

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3515
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.82 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1140 frames, 120 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            19443
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.507
_diffrn_reflns_theta_max         21.000
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1966
_reflns_number_gt                1410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.82 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.82'
_computing_data_reduction        'X-AREA 1.82'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          
;Refined as a 2-component twin:
TWIN -1 0 0 0 -1 0 0 0 1 2
BASF   0.45196,Twin
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1966
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2703(3) 0.1332(2) 0.01845(8) 0.0573(4) Uani 1 1 d . . . . .
O3 O 0.7055(3) 0.3438(2) 0.08172(8) 0.0575(4) Uani 1 1 d . . . . .
O4 O 0.6165(3) 0.3007(2) -0.04369(9) 0.0581(5) Uani 1 1 d . . . . .
H4O H 0.538(5) 0.252(4) -0.0074(17) 0.087 Uiso 1 1 d . U . . .
N1 N -0.0056(4) -0.0035(3) 0.08634(9) 0.0473(4) Uani 1 1 d . . . . .
H1N H -0.120(5) -0.051(3) 0.0499(13) 0.071 Uiso 1 1 d . U . . .
H2N H 0.440(5) 0.218(4) 0.1317(14) 0.071 Uiso 1 1 d . U . . .
N2 N 0.2990(4) 0.1421(2) 0.13027(9) 0.0485(5) Uani 1 1 d . . . . .
C1 C 0.1970(4) 0.0941(3) 0.07312(11) 0.0461(5) Uani 1 1 d . . . . .
C3 C 0.1599(4) 0.0774(3) 0.18050(11) 0.0440(5) Uani 1 1 d . . . . .
C4 C 0.1815(4) 0.0922(3) 0.24603(11) 0.0499(5) Uani 1 1 d . . . . .
H4 H 0.309863 0.154174 0.264593 0.060 Uiso 1 1 calc R U . . .
C5 C 0.0050(5) 0.0115(3) 0.28296(11) 0.0515(6) Uani 1 1 d . . . . .
H5 H 0.013851 0.020063 0.327321 0.062 Uiso 1 1 calc R U . . .
C6 C -0.1865(5) -0.0829(3) 0.25530(12) 0.0528(6) Uani 1 1 d . . . . .
H6 H -0.301055 -0.137301 0.281549 0.063 Uiso 1 1 calc R U . . .
C7 C -0.2091(5) -0.0969(3) 0.18942(11) 0.0515(6) Uani 1 1 d . . . . .
H7 H -0.337730 -0.158588 0.170836 0.062 Uiso 1 1 calc R U . . .
C8 C -0.0332(4) -0.0157(3) 0.15253(11) 0.0432(5) Uani 1 1 d . . . . .
C9 C 1.0433(4) 0.5267(3) 0.06752(11) 0.0493(5) Uani 1 1 d . . . . .
H9 H 1.067131 0.543079 0.111198 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8444(4) 0.4200(3) 0.04557(11) 0.0438(5) Uani 1 1 d . . . . .
C11 C 0.8058(4) 0.3976(3) -0.02557(10) 0.0441(5) Uani 1 1 d . . . . .


_geom_special_details            ?

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
O1 C1 1.247(3) . ?
O3 C10 1.223(3) . ?
O4 C11 1.329(3) . ?
O4 H4O 0.95(3) . ?
N1 C1 1.363(3) . ?
N1 C8 1.394(3) . ?
N1 H1N 1.05(3) . ?
N2 C1 1.366(3) . ?
N2 C3 1.386(3) . ?
N2 H2N 0.97(3) . ?
C3 C4 1.378(3) . ?
C3 C8 1.399(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C9 C11 1.337(3) 3_765 ?
C9 C10 1.439(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.510(3) . ?

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
C11 O4 H4O 110.5(18) . . ?
C1 N1 C8 109.05(19) . . ?
C1 N1 H1N 121.7(14) . . ?
C8 N1 H1N 129.1(14) . . ?
C1 N2 C3 110.05(19) . . ?
C1 N2 H2N 120.8(18) . . ?
C3 N2 H2N 129.0(18) . . ?
O1 C1 N1 125.4(2) . . ?
O1 C1 N2 127.1(2) . . ?
N1 C1 N2 107.42(19) . . ?
C4 C3 N2 132.4(2) . . ?
C4 C3 C8 121.4(2) . . ?
N2 C3 C8 106.16(19) . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 117.3(2) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 N1 131.4(2) . . ?
C7 C8 C3 121.3(2) . . ?
N1 C8 C3 107.3(2) . . ?
C11 C9 C10 120.5(2) 3_765 . ?
C11 C9 H9 119.8 3_765 . ?
C10 C9 H9 119.8 . . ?
O3 C10 C9 123.3(2) . . ?
O3 C10 C11 117.8(2) . . ?
C9 C10 C11 118.9(2) . . ?
O4 C11 C9 122.5(2) . 3_765 ?
O4 C11 C10 116.86(19) . . ?
C9 C11 C10 120.6(2) 3_765 . ?

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
C8 N1 C1 O1 -178.3(2) . . . . ?
C8 N1 C1 N2 0.6(3) . . . . ?
C3 N2 C1 O1 178.0(2) . . . . ?
C3 N2 C1 N1 -0.8(2) . . . . ?
C1 N2 C3 C4 -178.4(3) . . . . ?
C1 N2 C3 C8 0.8(2) . . . . ?
N2 C3 C4 C5 179.1(2) . . . . ?
C8 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 N1 -179.1(2) . . . . ?
C6 C7 C8 C3 -0.2(4) . . . . ?
C1 N1 C8 C7 178.9(2) . . . . ?
C1 N1 C8 C3 -0.1(3) . . . . ?
C4 C3 C8 C7 -0.2(4) . . . . ?
N2 C3 C8 C7 -179.5(2) . . . . ?
C4 C3 C8 N1 178.9(2) . . . . ?
N2 C3 C8 N1 -0.4(3) . . . . ?
C11 C9 C10 O3 177.8(2) 3_765 . . . ?
C11 C9 C10 C11 -1.1(4) 3_765 . . . ?
O3 C10 C11 O4 2.4(3) . . . . ?
C9 C10 C11 O4 -178.59(19) . . . . ?
O3 C10 C11 C9 -177.8(2) . . . 3_765 ?
C9 C10 C11 C9 1.1(4) . . . 3_765 ?

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
N2 H2N O3 0.97(3) 2.03(3) 2.890(3) 147(2) . yes
O4 H4O O1 0.95(3) 1.80(3) 2.627(2) 144(3) . yes
O4 H4O O3 0.95(3) 2.19(3) 2.683(2) 111(2) . yes
N1 H1N O1 1.05(3) 1.76(3) 2.802(2) 171(2) 3 yes
C5 H5 O3 0.93 2.65 3.331(3) 130.7 2_545 yes

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_IB_2H2O
_database_code_depnum_ccdc_archive 'CCDC 2016350'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

# Clave Lab.  :  ZA9
# Clave IF-UAP:  ZA9_b
# Solicitud: 250
# Firma en la Solicitud: Dra. Martha Sosa (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\ZA9_b\50mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-03-21

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Cl2 O4, 2(C8 H6 N2 O2), 2(H2 O)'
_chemical_formula_sum            'C22 H18 Cl2 N4 O10'
_chemical_formula_weight         569.30
_chemical_absolute_configuration .
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       ?

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                   27.986(3)
_cell_length_b                   4.6150(3)
_cell_length_c                   24.046(2)
_cell_angle_alpha                90
_cell_angle_beta                 132.364(5)
_cell_angle_gamma                90
_cell_volume                     2294.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    7909
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      23.60

_exptl_crystal_recrystallization_method 
;
Re-cristallisation from solvent: Ethanol
;

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3249
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1261 frames, 50-55 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            25780
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.757
_diffrn_reflns_theta_max         20.993
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2487
_reflns_number_gt                1413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0218P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2487
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   0.741
_refine_ls_restrained_S_all      0.741
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58581(7) -0.0595(3) 0.07477(8) 0.0370(4) Uani 1 1 d . . . . .
O2 O 0.68896(7) 0.0821(3) 0.22116(8) 0.0442(4) Uani 1 1 d . . . . .
N1 N 0.52520(8) 0.2825(3) 0.07032(10) 0.0299(4) Uani 1 1 d . . . . .
N2 N 0.62871(9) 0.4353(4) 0.21558(10) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.58053(10) 0.1373(4) 0.10547(11) 0.0292(5) Uani 1 1 d . . . . .
C2 C 0.63806(10) 0.2166(4) 0.18639(11) 0.0320(5) Uani 1 1 d . . . . .
C3 C 0.56964(10) 0.5762(4) 0.17792(11) 0.0301(5) Uani 1 1 d . . . . .
C4 C 0.56212(11) 0.7911(4) 0.21220(12) 0.0379(5) Uani 1 1 d . . . . .
H4 H 0.597043 0.846034 0.261559 0.045 Uiso 1 1 calc R U . . .
C5 C 0.50290(12) 0.9217(5) 0.17284(13) 0.0423(6) Uani 1 1 d . . . . .
H5 H 0.498050 1.064588 0.195991 0.051 Uiso 1 1 calc R U . . .
C6 C 0.45035(11) 0.8434(5) 0.09915(13) 0.0414(6) Uani 1 1 d . . . . .
H6 H 0.410569 0.933479 0.073121 0.050 Uiso 1 1 calc R U . . .
C7 C 0.45726(10) 0.6313(4) 0.06451(12) 0.0357(5) Uani 1 1 d . . . . .
H7 H 0.422210 0.578173 0.015037 0.043 Uiso 1 1 calc R U . . .
C8 C 0.51703(10) 0.4973(4) 0.10408(11) 0.0292(5) Uani 1 1 d . . . . .
Cl1 Cl 0.64189(3) 0.32016(11) 0.37272(3) 0.04056(16) Uani 1 1 d . . . . .
O4 O 0.68769(7) 0.3846(3) 0.52342(8) 0.0387(4) Uani 1 1 d . . . . .
O3 O 0.72340(7) 0.7236(3) 0.37083(8) 0.0398(4) Uani 1 1 d . . . . .
C11 C 0.71543(9) 0.5593(4) 0.50972(11) 0.0280(5) Uani 1 1 d . . . . .
C10 C 0.70089(10) 0.5543(4) 0.44372(11) 0.0291(5) Uani 1 1 d . . . . .
C9 C 0.73368(10) 0.7321(4) 0.42886(11) 0.0294(5) Uani 1 1 d . . . . .
O5W O 0.80616(8) 1.1053(4) 0.36835(9) 0.0501(5) Uani 1 1 d . . . . .
H1 H 0.4904(11) 0.229(5) 0.0233(13) 0.060 Uiso 1 1 d . U . . .
H2 H 0.6610(12) 0.485(5) 0.2612(13) 0.060 Uiso 1 1 d . U . . .
H4O H 0.6962(13) 0.410(6) 0.5635(15) 0.075 Uiso 1 1 d . U . . .
H1W H 0.8280(13) 1.244(6) 0.3726(15) 0.075 Uiso 1 1 d . U . . .
H2W H 0.7687(13) 1.108(6) 0.3235(15) 0.075 Uiso 1 1 d . U . . .


_geom_special_details            ?

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
O1 C1 1.241(2) . ?
O2 C2 1.228(2) . ?
N1 C1 1.341(3) . ?
N1 C8 1.394(2) . ?
N1 H1 0.90(2) . ?
N2 C2 1.352(3) . ?
N2 C3 1.399(3) . ?
N2 H2 0.86(2) . ?
C1 C2 1.513(3) . ?
C3 C8 1.389(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9300 . ?
Cl1 C10 1.735(2) . ?
O4 C11 1.306(2) . ?
O4 H4O 0.83(3) . ?
O3 C9 1.221(2) . ?
C11 C10 1.347(3) . ?
C11 C9 1.517(3) 7_666 ?
C10 C9 1.444(3) . ?
O5W H1W 0.84(3) . ?
O5W H2W 0.86(3) . ?

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
C1 N1 C8 124.13(18) . . ?
C1 N1 H1 117.8(15) . . ?
C8 N1 H1 117.9(15) . . ?
C2 N2 C3 124.65(18) . . ?
C2 N2 H2 117.3(17) . . ?
C3 N2 H2 118.0(17) . . ?
O1 C1 N1 122.74(18) . . ?
O1 C1 C2 119.47(19) . . ?
N1 C1 C2 117.78(18) . . ?
O2 C2 N2 124.44(19) . . ?
O2 C2 C1 119.61(19) . . ?
N2 C2 C1 115.94(19) . . ?
C8 C3 C4 119.4(2) . . ?
C8 C3 N2 118.54(18) . . ?
C4 C3 N2 122.10(18) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 120.47(19) . . ?
C3 C8 N1 118.83(19) . . ?
C7 C8 N1 120.69(18) . . ?
C11 O4 H4O 116.8(19) . . ?
O4 C11 C10 121.85(19) . . ?
O4 C11 C9 118.28(17) . 7_666 ?
C10 C11 C9 119.86(18) . 7_666 ?
C11 C10 C9 122.96(18) . . ?
C11 C10 Cl1 120.11(16) . . ?
C9 C10 Cl1 116.91(15) . . ?
O3 C9 C10 124.41(19) . . ?
O3 C9 C11 118.45(18) . 7_666 ?
C10 C9 C11 117.13(17) . 7_666 ?
H1W O5W H2W 108(2) . . ?

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
C8 N1 C1 O1 177.55(19) . . . . ?
C8 N1 C1 C2 -1.4(3) . . . . ?
C3 N2 C2 O2 -175.5(2) . . . . ?
C3 N2 C2 C1 4.0(3) . . . . ?
O1 C1 C2 O2 -1.2(3) . . . . ?
N1 C1 C2 O2 177.71(19) . . . . ?
O1 C1 C2 N2 179.28(18) . . . . ?
N1 C1 C2 N2 -1.8(3) . . . . ?
C2 N2 C3 C8 -3.0(3) . . . . ?
C2 N2 C3 C4 176.80(19) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
N2 C3 C4 C5 -179.6(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
N2 C3 C8 C7 179.83(18) . . . . ?
C4 C3 C8 N1 179.84(18) . . . . ?
N2 C3 C8 N1 -0.4(3) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C6 C7 C8 N1 179.99(18) . . . . ?
C1 N1 C8 C3 2.5(3) . . . . ?
C1 N1 C8 C7 -177.73(18) . . . . ?
O4 C11 C10 C9 -176.00(18) . . . . ?
C9 C11 C10 C9 2.7(3) 7_666 . . . ?
O4 C11 C10 Cl1 2.2(3) . . . . ?
C9 C11 C10 Cl1 -179.03(14) 7_666 . . . ?
C11 C10 C9 O3 176.8(2) . . . . ?
Cl1 C10 C9 O3 -1.4(3) . . . . ?
C11 C10 C9 C11 -2.7(3) . . . 7_666 ?
Cl1 C10 C9 C11 179.05(13) . . . 7_666 ?

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
N2 H2 O3 0.86(2) 2.24(2) 3.065(2) 162(2) . yes
C4 H4 O3 0.93 2.68 3.438(3) 138.6 . yes
C4 H4 Cl1 0.93 3.18 3.604(2) 110.2 . yes
O5W H2W O3 0.86(3) 2.83(3) 2.942(2) 89.1(18) . yes
N1 H1 O1 0.90(2) 1.99(2) 2.877(2) 172(2) 5_655 yes
O4 H4O O5W 0.83(3) 1.68(3) 2.490(2) 162(3) 7_666 yes
O5W H1W O1 0.84(3) 2.03(3) 2.798(2) 151(3) 4_665 yes
O5W H1W O2 0.84(3) 2.51(3) 3.144(2) 133(2) 4_665 yes
O5W H2W O2 0.86(3) 1.91(3) 2.766(2) 174(3) 1_565 yes
N1 H1 O1 0.90(2) 1.99(2) 2.877(2) 172(2) 5_655 yes
O4 H4O O5W 0.83(3) 1.68(3) 2.490(2) 162(3) 7_666 yes
O5W H1W O1 0.84(3) 2.03(3) 2.798(2) 151(3) 4_665 yes
O5W H1W O2 0.84(3) 2.51(3) 3.144(2) 133(2) 4_665 yes
O5W H2W O2 0.86(3) 1.91(3) 2.766(2) 174(3) 1_565 yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 2016351'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

# Clave Lab.  :  ZA1
# Clave IF-UAP:  ZA1
# Solicitud: 189
# Firma en la Solicitud: Dra. Martha Sosa (FCQ-BUAP)
# Clave datos : ... \BUAP\Sylvain\ZA1\45mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2018-10-17

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Cl2 O4, 2(C7 H6 N2 O)'
_chemical_formula_sum            'C20 H14 Cl2 N4 O6'
_chemical_formula_weight         477.25
_chemical_absolute_configuration .
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       ?

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

_cell_length_a                   8.4521(5)
_cell_length_b                   5.1303(2)
_cell_length_c                   23.1482(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.316(5)
_cell_angle_gamma                90
_cell_volume                     990.51(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    15454
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.44

_exptl_crystal_recrystallization_method 
;
Re-cristallisation from solvent: Acetonitrile
;

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.075
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 9 0.0380
1 2 -9 0.0370
-1 2 9 0.0560
3 -1 -5 0.0630
1 -2 -9 0.0820
-3 -1 -5 0.0910
7 1 4 0.1090

_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4915
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.82 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1168 frames, 50-70 s/frame, 1 deg./frame, detector distance = 45 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            20107
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         20.996
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2160
_reflns_number_gt                1600
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.82 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.82'
_computing_data_reduction        'X-AREA 1.82'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2160
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.54056(7) 0.18828(10) 0.63114(2) 0.05506(19) Uani 1 1 d . . . . .
O1 O 0.14041(19) 0.2726(3) 0.51833(7) 0.0581(4) Uani 1 1 d . . . . .
O3 O 0.34695(18) -0.2487(3) 0.57467(6) 0.0546(4) Uani 1 1 d . . . . .
O4 O 0.69292(19) 0.4192(3) 0.53684(7) 0.0517(4) Uani 1 1 d . . . . .
H4O H 0.734(3) 0.484(5) 0.5108(12) 0.070(8) Uiso 1 1 d . . . . .
N1 N 0.0044(2) 0.0251(3) 0.57829(8) 0.0482(4) Uani 1 1 d . . . . .
H1 H -0.041(3) -0.081(4) 0.5505(10) 0.049(6) Uiso 1 1 d . . . . .
N2 N 0.1411(2) 0.3563(3) 0.61747(9) 0.0524(5) Uani 1 1 d . . . . .
H2 H 0.201(3) 0.472(4) 0.6213(10) 0.048(6) Uiso 1 1 d . . . . .
C1 C 0.0990(2) 0.2241(4) 0.56670(10) 0.0481(5) Uani 1 1 d . . . . .
C3 C 0.0760(2) 0.2379(3) 0.66247(10) 0.0468(5) Uani 1 1 d . . . . .
C4 C 0.0834(3) 0.2950(4) 0.72094(11) 0.0552(5) Uani 1 1 d . . . . .
C5 C -0.0012(3) 0.1356(4) 0.75330(11) 0.0585(6) Uani 1 1 d . . . . .
C6 C -0.0903(3) -0.0723(4) 0.72783(11) 0.0577(6) Uani 1 1 d . . . . .
C7 C -0.0973(3) -0.1319(4) 0.66898(11) 0.0528(5) Uani 1 1 d . . . . .
C8 C -0.0128(2) 0.0276(3) 0.63661(9) 0.0455(5) Uani 1 1 d . . . . .
C9 C 0.4191(2) -0.1305(3) 0.54157(8) 0.0405(4) Uani 1 1 d . . . . .
C10 C 0.5234(2) 0.0901(3) 0.55979(8) 0.0409(4) Uani 1 1 d . . . . .
C11 C 0.6003(2) 0.2152(3) 0.52124(8) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.145(3) 0.425(4) 0.7403(10) 0.060(6) Uiso 1 1 d . . . . .
H5 H -0.004(3) 0.169(5) 0.7903(12) 0.068(7) Uiso 1 1 d . . . . .
H6 H -0.150(3) -0.181(5) 0.7505(12) 0.072(7) Uiso 1 1 d . . . . .
H7 H -0.163(3) -0.268(4) 0.6491(10) 0.055(6) Uiso 1 1 d . . . . .


_geom_special_details            ?
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 C10 1.710(2) . ?
O1 C1 1.251(3) . ?
O3 C9 1.216(2) . ?
O4 C11 1.321(2) . ?
O4 H4O 0.81(3) . ?
N1 C1 1.350(2) . ?
N1 C8 1.381(3) . ?
N1 H1 0.88(2) . ?
N2 C1 1.354(3) . ?
N2 C3 1.394(3) . ?
N2 H2 0.77(2) . ?
C3 C4 1.376(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.92(2) . ?
C5 C6 1.381(3) . ?
C5 H5 0.88(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.96(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.96(2) . ?
C9 C10 1.454(3) . ?
C9 C11 1.501(3) 3_656 ?
C10 C11 1.349(3) . ?

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
C11 O4 H4O 115.3(18) . . ?
C1 N1 C8 110.30(18) . . ?
C1 N1 H1 121.7(14) . . ?
C8 N1 H1 127.9(14) . . ?
C1 N2 C3 110.53(17) . . ?
C1 N2 H2 123.9(17) . . ?
C3 N2 H2 125.3(17) . . ?
O1 C1 N1 126.1(2) . . ?
O1 C1 N2 127.25(18) . . ?
N1 C1 N2 106.69(19) . . ?
C4 C3 C8 121.54(19) . . ?
C4 C3 N2 132.97(19) . . ?
C8 C3 N2 105.47(18) . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 H4 124.5(15) . . ?
C5 C4 H4 117.9(15) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 118.0(17) . . ?
C4 C5 H5 120.7(17) . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 120.8(15) . . ?
C7 C6 H6 117.7(15) . . ?
C8 C7 C6 117.2(2) . . ?
C8 C7 H7 118.7(14) . . ?
C6 C7 H7 123.9(14) . . ?
N1 C8 C7 132.0(2) . . ?
N1 C8 C3 106.99(16) . . ?
C7 C8 C3 121.0(2) . . ?
O3 C9 C10 123.20(18) . . ?
O3 C9 C11 118.60(17) . 3_656 ?
C10 C9 C11 118.20(15) . 3_656 ?
C11 C10 C9 120.85(18) . . ?
C11 C10 Cl1 121.61(15) . . ?
C9 C10 Cl1 117.52(13) . . ?
O4 C11 C10 121.59(18) . . ?
O4 C11 C9 117.45(15) . 3_656 ?
C10 C11 C9 120.95(17) . 3_656 ?

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
C8 N1 C1 O1 178.52(19) . . . . ?
C8 N1 C1 N2 -0.7(2) . . . . ?
C3 N2 C1 O1 -177.8(2) . . . . ?
C3 N2 C1 N1 1.4(2) . . . . ?
C1 N2 C3 C4 179.9(2) . . . . ?
C1 N2 C3 C8 -1.5(2) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
N2 C3 C4 C5 178.3(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C1 N1 C8 C7 179.5(2) . . . . ?
C1 N1 C8 C3 -0.2(2) . . . . ?
C6 C7 C8 N1 -179.4(2) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C4 C3 C8 N1 179.86(19) . . . . ?
N2 C3 C8 N1 1.0(2) . . . . ?
C4 C3 C8 C7 0.1(3) . . . . ?
N2 C3 C8 C7 -178.74(18) . . . . ?
O3 C9 C10 C11 -179.76(18) . . . . ?
C11 C9 C10 C11 0.1(3) 3_656 . . . ?
O3 C9 C10 Cl1 -1.2(3) . . . . ?
C11 C9 C10 Cl1 178.62(13) 3_656 . . . ?
C9 C10 C11 O4 178.65(16) . . . . ?
Cl1 C10 C11 O4 0.2(3) . . . . ?
C9 C10 C11 C9 -0.1(3) . . . 3_656 ?
Cl1 C10 C11 C9 -178.56(13) . . . 3_656 ?

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
N2 H2 O3 0.77(2) 2.28(2) 2.945(2) 145(2) 1_565 yes
N1 H1 O1 0.88(2) 1.94(2) 2.819(2) 171.7(19) 3_556 yes
O4 H4O O1 0.81(3) 1.84(3) 2.588(2) 153(3) 3_666 yes
C6 H6 Cl1 0.96(3) 2.83(3) 3.449(2) 123.1(19) 2_546 yes

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_IA_2H2O
_database_code_depnum_ccdc_archive 'CCDC 2016349'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

# Clave Lab.  :  CARMEN1
# Clave IF-UAP:  CARMEN1
# Solicitud: 137
# Firma en la Solicitud: Dra. Martha Sosa (FCQ-BUAP)
# Clave datos : ... \BUAP\FCQ\CARMEN1\40mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-03-20

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Cl2 O4, 2(C8 H6 N2 O2), 2(H2 O)'
_chemical_formula_sum            'C22 H18 Cl2 N4 O10'
_chemical_formula_weight         569.30
_chemical_absolute_configuration .
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7183(6)
_cell_length_b                   10.9094(12)
_cell_length_c                   11.9445(16)
_cell_angle_alpha                74.120(9)
_cell_angle_beta                 81.304(11)
_cell_angle_gamma                81.681(10)
_cell_volume                     581.11(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    8964
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.20

_exptl_crystal_recrystallization_method 
;
Re-cristallisation from solvent: Water
;

_exptl_crystal_description       irregular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4966
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1142 frames, 80 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            13338
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         21.000
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2515
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_restrained_S_all      0.841
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.49263(13) 0.28174(5) 0.46355(5) 0.04378(17) Uani 1 1 d . . . . .
O1 O 1.0198(3) 0.16813(12) -0.02166(13) 0.0388(4) Uani 1 1 d . . . . .
O2 O 0.7867(3) 0.37102(12) 0.06579(13) 0.0437(4) Uani 1 1 d . . . . .
O3 O 0.1081(3) 0.44417(12) 0.29290(13) 0.0424(4) Uani 1 1 d . . . . .
O4 O 0.3302(4) 0.37365(13) 0.67565(15) 0.0437(4) Uani 1 1 d . . . . .
H4O H 0.283(6) 0.391(2) 0.749(3) 0.095(10) Uiso 1 1 d . . . . .
N1 N 0.6764(4) 0.04952(15) 0.09251(15) 0.0315(4) Uani 1 1 d . . . . .
H1 H 0.760(4) -0.0150(18) 0.0693(18) 0.040(6) Uiso 1 1 d . . . . .
N2 N 0.4372(4) 0.25281(15) 0.17793(16) 0.0336(4) Uani 1 1 d . . . . .
H2 H 0.369(5) 0.317(2) 0.210(2) 0.057(7) Uiso 1 1 d . . . . .
C3 C 0.3167(4) 0.13676(17) 0.22220(17) 0.0301(5) Uani 1 1 d . . . . .
C11 C 0.1773(4) 0.43067(16) 0.59084(18) 0.0289(5) Uani 1 1 d . . . . .
C8 C 0.4386(4) 0.03345(16) 0.17863(17) 0.0286(5) Uani 1 1 d . . . . .
C2 C 0.6724(5) 0.27060(17) 0.09905(18) 0.0314(5) Uani 1 1 d . . . . .
C10 C 0.2242(4) 0.40080(16) 0.48584(18) 0.0299(5) Uani 1 1 d . . . . .
C1 C 0.8029(5) 0.15750(17) 0.05120(18) 0.0298(5) Uani 1 1 d . . . . .
C9 C 0.0640(4) 0.46630(16) 0.38961(19) 0.0297(5) Uani 1 1 d . . . . .
C7 C 0.3253(5) -0.08359(18) 0.22051(19) 0.0374(5) Uani 1 1 d . . . . .
H7 H 0.407167 -0.153304 0.191623 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0808(5) 0.12347(19) 0.30714(19) 0.0384(5) Uani 1 1 d . . . . .
H4 H -0.001719 0.192957 0.336247 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0911(5) -0.09518(19) 0.3051(2) 0.0439(6) Uani 1 1 d . . . . .
H6 H 0.014579 -0.173279 0.333271 0.053 Uiso 1 1 calc R U . . .
C5 C -0.0323(5) 0.0080(2) 0.34870(19) 0.0442(6) Uani 1 1 d . . . . .
H5 H -0.190783 -0.000748 0.405841 0.053 Uiso 1 1 calc R U . . .
O5W O 0.2969(4) 0.39244(14) -0.12033(14) 0.0434(4) Uani 1 1 d . . . . .
H1W H 0.172(6) 0.350(2) -0.077(2) 0.065 Uiso 1 1 d . U . . .
H2W H 0.275(5) 0.464(2) -0.106(2) 0.065 Uiso 1 1 d . U . . .


_geom_special_details            ?

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 C10 1.7243(18) . ?
O1 C1 1.236(2) . ?
O2 C2 1.232(2) . ?
O3 C9 1.225(2) . ?
O4 C11 1.296(2) . ?
O4 H4O 0.93(3) . ?
N1 C1 1.335(2) . ?
N1 C8 1.399(2) . ?
N1 H1 0.85(2) . ?
N2 C2 1.343(3) . ?
N2 C3 1.399(2) . ?
N2 H2 0.89(2) . ?
C3 C4 1.384(3) . ?
C3 C8 1.384(2) . ?
C11 C10 1.359(3) . ?
C11 C9 1.519(3) 2_566 ?
C8 C7 1.390(3) . ?
C2 C1 1.512(3) . ?
C10 C9 1.435(3) . ?
C7 C6 1.375(3) . ?
C7 H7 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.385(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
O5W H1W 0.83(2) . ?
O5W H2W 0.84(2) . ?

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
C11 O4 H4O 120.4(18) . . ?
C1 N1 C8 124.50(17) . . ?
C1 N1 H1 116.0(14) . . ?
C8 N1 H1 119.1(14) . . ?
C2 N2 C3 124.73(17) . . ?
C2 N2 H2 116.4(15) . . ?
C3 N2 H2 118.4(15) . . ?
C4 C3 C8 119.82(18) . . ?
C4 C3 N2 121.82(17) . . ?
C8 C3 N2 118.36(18) . . ?
O4 C11 C10 122.32(18) . . ?
O4 C11 C9 118.56(18) . 2_566 ?
C10 C11 C9 119.12(18) . 2_566 ?
C3 C8 C7 120.11(19) . . ?
C3 C8 N1 118.70(17) . . ?
C7 C8 N1 121.20(17) . . ?
O2 C2 N2 124.20(18) . . ?
O2 C2 C1 119.32(18) . . ?
N2 C2 C1 116.48(17) . . ?
C11 C10 C9 122.98(17) . . ?
C11 C10 Cl1 119.58(16) . . ?
C9 C10 Cl1 117.42(15) . . ?
O1 C1 N1 123.45(17) . . ?
O1 C1 C2 119.41(17) . . ?
N1 C1 C2 117.13(18) . . ?
O3 C9 C10 124.32(18) . . ?
O3 C9 C11 117.84(19) . 2_566 ?
C10 C9 C11 117.83(17) . 2_566 ?
C6 C7 C8 119.32(19) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C5 C4 C3 120.29(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
H1W O5W H2W 107(2) . . ?

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
N1 H1 O1 0.85(2) 2.01(2) 2.856(2) 176(2) 2_755 yes
O4 H4O O5W 0.93(3) 1.58(3) 2.481(2) 162(3) 1_556 yes
N2 H2 O3 0.89(2) 2.07(2) 2.940(2) 165(2) . yes
C4 H4 O3 0.93 2.76 3.476(3) 134.9 . yes
C4 H4 Cl1 0.93 3.35 3.753(2) 108.7 . yes

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042

