# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_DiBrY
_database_code_depnum_ccdc_archive 'CCDC 1996230'
loop_
_audit_author_name
_audit_author_address
'Nicola Demitri'
;Elettra Synchrotron XRD BLs
Italy
;
_audit_update_record             
;
2021-07-25 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 Br2 N O3, 2 H2 O'
_chemical_formula_sum            'C9 H13 Br2 N O5'
_chemical_formula_weight         375.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2364 2.4089 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   5.692(1)
_cell_length_b                   10.588(2)
_cell_length_c                   10.925(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.14(3)
_cell_angle_gamma                90
_cell_volume                     657.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1181
_cell_measurement_theta_min      1.839
_cell_measurement_theta_max      29.999

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_diffrn_measurement_method       'π scans'

_exptl_crystal_description       'Thin needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.951
_shelx_estimated_absorpt_T_min   0.469
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7037
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_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         1.839
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             3669
_reflns_number_gt                3643
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.858
_reflns_Friedel_fraction_full    0.873

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

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for methyl and hydroxyl groups). 
Anisotropic thermal motion modeling has been applied only to all atoms.
Geometric restrains (DFIX, DANG) have been used to model solvent molecules.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.4072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.98(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3669
_refine_ls_number_parameters     169
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.138
_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
Br2_1 Br -0.08477(8) 0.32486(4) 0.51657(4) 0.0202(2) Uani 1 1 d . . . . .
Br1_1 Br 0.41863(12) 0.66347(5) 0.22461(5) 0.0289(2) Uani 1 1 d . . . . .
N_1 N 0.7277(8) 0.7264(4) 0.8819(4) 0.0209(8) Uani 1 1 d . . . . .
H0A_1 H 0.871882 0.748360 0.856763 0.031 Uiso 1 1 calc DR U . . .
H0B_1 H 0.740516 0.654964 0.928104 0.031 Uiso 1 1 calc DR U . . .
H0C_1 H 0.670221 0.790138 0.927536 0.031 Uiso 1 1 calc DR U . . .
CA_1 C 0.5633(8) 0.7030(5) 0.7720(4) 0.0174(8) Uani 1 1 d . . . . .
HA_1 H 0.559935 0.779249 0.717984 0.021 Uiso 1 1 calc R U . . .
CB_1 C 0.6514(9) 0.5890(5) 0.7005(5) 0.0198(8) Uani 1 1 d . . . . .
HB1_1 H 0.810391 0.607694 0.672734 0.024 Uiso 1 1 calc R U . . .
HB2_1 H 0.664054 0.514854 0.755586 0.024 Uiso 1 1 calc R U . . .
CG_1 C 0.4903(9) 0.5574(5) 0.5909(4) 0.0175(8) Uani 1 1 d . . . . .
CD1_1 C 0.5241(10) 0.6124(5) 0.4772(5) 0.0191(8) Uani 1 1 d . . . . .
HD1_1 H 0.649622 0.670381 0.468738 0.023 Uiso 1 1 calc R U . . .
CE1_1 C 0.3750(10) 0.5830(4) 0.3759(4) 0.0192(8) Uani 1 1 d . . . . .
CZ_1 C 0.1884(9) 0.4972(5) 0.3848(4) 0.0182(8) Uani 1 1 d . . . . .
OH_1 O 0.0495(8) 0.4719(4) 0.2841(4) 0.0242(8) Uani 1 1 d . . . . .
HH_1 H -0.049886 0.416716 0.300781 0.036 Uiso 1 1 calc R U . . .
CE2_1 C 0.1581(9) 0.4433(4) 0.4998(4) 0.0171(8) Uani 1 1 d . . . . .
CD2_1 C 0.3059(9) 0.4722(4) 0.6004(4) 0.0185(8) Uani 1 1 d . . . . .
HD2_1 H 0.281300 0.433500 0.677128 0.022 Uiso 1 1 calc R U . . .
C_1 C 0.3185(9) 0.6823(4) 0.8201(4) 0.0174(8) Uani 1 1 d . . . . .
O_1 O 0.2930(8) 0.5891(4) 0.8876(4) 0.0274(8) Uani 1 1 d . . . . .
OXT_1 O 0.1597(8) 0.7611(4) 0.7888(4) 0.0229(7) Uani 1 1 d . . . . .
O_2 O -0.0683(8) 0.5226(5) 0.0275(4) 0.0305(10) Uani 1 1 d D . . . .
H1_2 H -0.022(9) 0.512(12) 0.1039(19) 0.046 Uiso 1 1 d D U . . .
H2_2 H 0.054(5) 0.529(12) -0.017(4) 0.046 Uiso 1 1 d D U . . .
O_3 O 0.5227(9) 0.3807(4) 0.9747(4) 0.0265(8) Uani 1 1 d D . . . .
H1_3 H 0.616(6) 0.408(4) 1.0348(15) 0.040 Uiso 1 1 d D U . . .
H2_3 H 0.446(10) 0.444(3) 0.941(5) 0.040 Uiso 1 1 d D 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
Br2_1 CE2_1 1.883(5) . ?
Br1_1 CE1_1 1.888(5) . ?
N_1 CA_1 1.502(6) . ?
N_1 H0A_1 0.9100 . ?
N_1 H0B_1 0.9100 . ?
N_1 H0C_1 0.9100 . ?
CA_1 C_1 1.532(7) . ?
CA_1 CB_1 1.537(7) . ?
CA_1 HA_1 1.0000 . ?
CB_1 CG_1 1.505(7) . ?
CB_1 HB1_1 0.9900 . ?
CB_1 HB2_1 0.9900 . ?
CG_1 CD2_1 1.393(7) . ?
CG_1 CD1_1 1.395(7) . ?
CD1_1 CE1_1 1.392(7) . ?
CD1_1 HD1_1 0.9500 . ?
CE1_1 CZ_1 1.405(7) . ?
CZ_1 OH_1 1.346(6) . ?
CZ_1 CE2_1 1.399(7) . ?
OH_1 HH_1 0.8400 . ?
CE2_1 CD2_1 1.381(7) . ?
CD2_1 HD2_1 0.9500 . ?
C_1 O_1 1.245(6) . ?
C_1 OXT_1 1.263(6) . ?
O_2 H1_2 0.870(7) . ?
O_2 H2_2 0.871(7) . ?
O_3 H1_3 0.870(7) . ?
O_3 H2_3 0.870(7) . ?

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
CA_1 N_1 H0A_1 109.5 . . ?
CA_1 N_1 H0B_1 109.5 . . ?
H0A_1 N_1 H0B_1 109.5 . . ?
CA_1 N_1 H0C_1 109.5 . . ?
H0A_1 N_1 H0C_1 109.5 . . ?
H0B_1 N_1 H0C_1 109.5 . . ?
N_1 CA_1 C_1 106.7(4) . . ?
N_1 CA_1 CB_1 109.3(4) . . ?
C_1 CA_1 CB_1 113.0(4) . . ?
N_1 CA_1 HA_1 109.2 . . ?
C_1 CA_1 HA_1 109.2 . . ?
CB_1 CA_1 HA_1 109.2 . . ?
CG_1 CB_1 CA_1 112.2(4) . . ?
CG_1 CB_1 HB1_1 109.2 . . ?
CA_1 CB_1 HB1_1 109.2 . . ?
CG_1 CB_1 HB2_1 109.2 . . ?
CA_1 CB_1 HB2_1 109.2 . . ?
HB1_1 CB_1 HB2_1 107.9 . . ?
CD2_1 CG_1 CD1_1 118.6(4) . . ?
CD2_1 CG_1 CB_1 120.9(4) . . ?
CD1_1 CG_1 CB_1 120.5(5) . . ?
CE1_1 CD1_1 CG_1 120.4(5) . . ?
CE1_1 CD1_1 HD1_1 119.8 . . ?
CG_1 CD1_1 HD1_1 119.8 . . ?
CD1_1 CE1_1 CZ_1 121.3(4) . . ?
CD1_1 CE1_1 Br1_1 119.4(4) . . ?
CZ_1 CE1_1 Br1_1 119.2(4) . . ?
OH_1 CZ_1 CE2_1 123.9(5) . . ?
OH_1 CZ_1 CE1_1 119.0(4) . . ?
CE2_1 CZ_1 CE1_1 117.2(4) . . ?
CZ_1 OH_1 HH_1 109.5 . . ?
CD2_1 CE2_1 CZ_1 121.6(4) . . ?
CD2_1 CE2_1 Br2_1 119.3(4) . . ?
CZ_1 CE2_1 Br2_1 119.1(4) . . ?
CE2_1 CD2_1 CG_1 120.9(4) . . ?
CE2_1 CD2_1 HD2_1 119.6 . . ?
CG_1 CD2_1 HD2_1 119.6 . . ?
O_1 C_1 OXT_1 125.4(5) . . ?
O_1 C_1 CA_1 117.0(4) . . ?
OXT_1 C_1 CA_1 117.6(4) . . ?
H1_2 O_2 H2_2 109.3(9) . . ?
H1_3 O_3 H2_3 109.3(9) . . ?

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
N_1 CA_1 CB_1 CG_1 178.2(4) . . . . ?
C_1 CA_1 CB_1 CG_1 59.5(5) . . . . ?
CA_1 CB_1 CG_1 CD2_1 -90.6(6) . . . . ?
CA_1 CB_1 CG_1 CD1_1 89.9(6) . . . . ?
CD2_1 CG_1 CD1_1 CE1_1 0.4(8) . . . . ?
CB_1 CG_1 CD1_1 CE1_1 180.0(5) . . . . ?
CG_1 CD1_1 CE1_1 CZ_1 -0.4(8) . . . . ?
CG_1 CD1_1 CE1_1 Br1_1 177.8(4) . . . . ?
CD1_1 CE1_1 CZ_1 OH_1 -179.9(5) . . . . ?
Br1_1 CE1_1 CZ_1 OH_1 1.9(7) . . . . ?
CD1_1 CE1_1 CZ_1 CE2_1 0.4(7) . . . . ?
Br1_1 CE1_1 CZ_1 CE2_1 -177.8(4) . . . . ?
OH_1 CZ_1 CE2_1 CD2_1 179.9(5) . . . . ?
CE1_1 CZ_1 CE2_1 CD2_1 -0.4(7) . . . . ?
OH_1 CZ_1 CE2_1 Br2_1 1.7(7) . . . . ?
CE1_1 CZ_1 CE2_1 Br2_1 -178.6(4) . . . . ?
CZ_1 CE2_1 CD2_1 CG_1 0.5(7) . . . . ?
Br2_1 CE2_1 CD2_1 CG_1 178.7(4) . . . . ?
CD1_1 CG_1 CD2_1 CE2_1 -0.4(7) . . . . ?
CB_1 CG_1 CD2_1 CE2_1 180.0(4) . . . . ?
N_1 CA_1 C_1 O_1 -63.2(6) . . . . ?
CB_1 CA_1 C_1 O_1 57.0(6) . . . . ?
N_1 CA_1 C_1 OXT_1 116.5(5) . . . . ?
CB_1 CA_1 C_1 OXT_1 -123.3(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
N_1 H0A_1 OXT_1 0.91 1.84 2.737(6) 168.1 1_655 yes
N_1 H0B_1 O_2 0.91 2.05 2.886(7) 152.5 1_656 yes
N_1 H0C_1 O_3 0.91 1.84 2.720(6) 161.2 2_657 yes
CD1_1 HD1_1 Br2_1 0.95 2.97 3.902(5) 168.9 2_656 yes
OH_1 HH_1 Br2_1 0.84 2.57 3.110(4) 123.3 . yes
OH_1 HH_1 OXT_1 0.84 2.00 2.632(6) 131.5 2_546 yes
O_2 H1_2 OH_1 0.870(7) 2.032(14) 2.897(6) 173(8) . yes
O_2 H2_2 O_1 0.871(7) 1.87(4) 2.721(6) 164(12) 1_554 yes
O_3 H1_3 O_2 0.870(7) 2.175(16) 2.804(7) 128.9(17) 1_656 yes
O_3 H2_3 O_1 0.870(7) 1.845(12) 2.711(6) 173(5) . yes

_refine_diff_density_max         0.927
_refine_diff_density_min         -1.866
_refine_diff_density_rms         0.257

####################################################################### 
# 
# 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_lg216_DiClTr_100k_0m
_database_code_depnum_ccdc_archive 'CCDC 2128970'
loop_
_audit_author_name
_audit_author_address
'Andrea Pizzi'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 Cl2 N O4'
_chemical_formula_weight         268.09

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'

_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'

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

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

_cell_length_a                   7.3436(2)
_cell_length_b                   7.4422(2)
_cell_length_c                   20.8254(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1138.16(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7570
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      31.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.568
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8858
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.914
_diffrn_reflns_theta_max         31.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3618
_reflns_number_gt                3543
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+0.1587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3618
_refine_ls_number_parameters     152
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_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
OW O 0.64269(17) 0.34527(15) 0.45886(7) 0.0310(3) Uani 1 1 d D . . . .
HW1 H 0.7265(19) 0.428(2) 0.4610(13) 0.046 Uiso 1 1 d D U . . .
HW2 H 0.5372(13) 0.394(3) 0.4672(12) 0.046 Uiso 1 1 d D U . . .
Cl1 Cl 0.64592(4) 0.48321(4) 0.23398(2) 0.01444(7) Uani 1 1 d . . . . .
Cl2 Cl 0.79372(5) -0.16060(4) 0.12849(2) 0.01707(7) Uani 1 1 d . . . . .
O3 O 0.66378(13) 0.22540(12) 0.13135(4) 0.01351(17) Uani 1 1 d . . . . .
H9 H 0.671870 0.147954 0.102145 0.020 Uiso 1 1 calc R U . . .
O1 O 0.87332(14) -0.36143(13) 0.48050(5) 0.01614(18) Uani 1 1 d . . . . .
O2 O 0.84182(14) -0.07999(13) 0.51786(4) 0.01586(18) Uani 1 1 d . . . . .
C5 C 0.77347(17) 0.20102(17) 0.30178(6) 0.0114(2) Uani 1 1 d . . . . .
H4 H 0.768534 0.278534 0.337979 0.014 Uiso 1 1 calc R U . . .
N1 N 0.59051(13) -0.01369(14) 0.42346(5) 0.01039(18) Uani 1 1 d . . . . .
H7 H 0.517686 -0.059796 0.454736 0.016 Uiso 1 1 calc R U . . .
H6 H 0.524874 0.000239 0.386729 0.016 Uiso 1 1 calc R U . . .
H8 H 0.634489 0.094854 0.436271 0.016 Uiso 1 1 calc R U . . .
C2 C 0.74589(16) -0.13928(16) 0.41134(5) 0.0098(2) Uani 1 1 d . . . . .
H1 H 0.701869 -0.246224 0.386756 0.012 Uiso 1 1 calc R U . . .
C3 C 0.89708(16) -0.04402(17) 0.37333(6) 0.0124(2) Uani 1 1 d . . . . .
H3 H 0.942981 0.058318 0.399022 0.015 Uiso 1 1 calc R U . . .
H2 H 0.999394 -0.128833 0.367027 0.015 Uiso 1 1 calc R U . . .
C4 C 0.83633(16) 0.02473(17) 0.30864(5) 0.0110(2) Uani 1 1 d . . . . .
C6 C 0.71830(17) 0.26249(15) 0.24193(6) 0.0106(2) Uani 1 1 d . . . . .
C7 C 0.72181(16) 0.15448(17) 0.18710(5) 0.01034(19) Uani 1 1 d . . . . .
C9 C 0.84169(17) -0.08557(16) 0.25458(6) 0.0117(2) Uani 1 1 d . . . . .
H5 H 0.883969 -0.205727 0.258416 0.014 Uiso 1 1 calc R U . . .
C8 C 0.78576(17) -0.02133(16) 0.19513(5) 0.0114(2) Uani 1 1 d . . . . .
C1 C 0.82538(16) -0.20005(16) 0.47585(5) 0.0105(2) Uani 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
OW HW1 0.874(6) . ?
OW HW2 0.871(6) . ?
Cl1 C6 1.7345(12) . ?
Cl2 C8 1.7331(12) . ?
O3 C7 1.3448(13) . ?
O3 H9 0.8400 . ?
O1 C1 1.2553(15) . ?
O2 C1 1.2564(14) . ?
C5 C6 1.3880(16) . ?
C5 C4 1.3981(17) . ?
C5 H4 0.9500 . ?
N1 C2 1.4964(15) . ?
N1 H7 0.9100 . ?
N1 H6 0.9100 . ?
N1 H8 0.9100 . ?
C2 C1 1.5330(16) . ?
C2 C3 1.5369(17) . ?
C2 H1 1.0000 . ?
C3 C4 1.5085(16) . ?
C3 H3 0.9900 . ?
C3 H2 0.9900 . ?
C4 C9 1.3940(17) . ?
C6 C7 1.3967(17) . ?
C7 C8 1.4002(17) . ?
C9 C8 1.3891(16) . ?
C9 H5 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
HW1 OW HW2 108.9(8) . . ?
C7 O3 H9 109.5 . . ?
C6 C5 C4 119.83(11) . . ?
C6 C5 H4 120.1 . . ?
C4 C5 H4 120.1 . . ?
C2 N1 H7 109.5 . . ?
C2 N1 H6 109.5 . . ?
H7 N1 H6 109.5 . . ?
C2 N1 H8 109.5 . . ?
H7 N1 H8 109.5 . . ?
H6 N1 H8 109.5 . . ?
N1 C2 C1 109.08(9) . . ?
N1 C2 C3 110.46(9) . . ?
C1 C2 C3 108.20(9) . . ?
N1 C2 H1 109.7 . . ?
C1 C2 H1 109.7 . . ?
C3 C2 H1 109.7 . . ?
C4 C3 C2 113.75(9) . . ?
C4 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C4 C3 H2 108.8 . . ?
C2 C3 H2 108.8 . . ?
H3 C3 H2 107.7 . . ?
C9 C4 C5 118.64(11) . . ?
C9 C4 C3 120.88(11) . . ?
C5 C4 C3 120.48(11) . . ?
C5 C6 C7 122.62(11) . . ?
C5 C6 Cl1 119.17(9) . . ?
C7 C6 Cl1 118.20(9) . . ?
O3 C7 C6 118.31(11) . . ?
O3 C7 C8 125.19(11) . . ?
C6 C7 C8 116.51(10) . . ?
C8 C9 C4 120.59(11) . . ?
C8 C9 H5 119.7 . . ?
C4 C9 H5 119.7 . . ?
C9 C8 C7 121.82(11) . . ?
C9 C8 Cl2 119.86(9) . . ?
C7 C8 Cl2 118.32(9) . . ?
O1 C1 O2 126.85(11) . . ?
O1 C1 C2 117.17(10) . . ?
O2 C1 C2 115.91(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -60.09(13) . . . . ?
C1 C2 C3 C4 -179.43(10) . . . . ?
C6 C5 C4 C9 -0.06(17) . . . . ?
C6 C5 C4 C3 179.90(11) . . . . ?
C2 C3 C4 C9 -86.94(14) . . . . ?
C2 C3 C4 C5 93.10(13) . . . . ?
C4 C5 C6 C7 0.28(19) . . . . ?
C4 C5 C6 Cl1 -178.46(9) . . . . ?
C5 C6 C7 O3 179.29(11) . . . . ?
Cl1 C6 C7 O3 -1.96(16) . . . . ?
C5 C6 C7 C8 -0.45(18) . . . . ?
Cl1 C6 C7 C8 178.30(9) . . . . ?
C5 C4 C9 C8 0.04(18) . . . . ?
C3 C4 C9 C8 -179.92(11) . . . . ?
C4 C9 C8 C7 -0.23(19) . . . . ?
C4 C9 C8 Cl2 179.94(9) . . . . ?
O3 C7 C8 C9 -179.30(12) . . . . ?
C6 C7 C8 C9 0.42(18) . . . . ?
O3 C7 C8 Cl2 0.54(17) . . . . ?
C6 C7 C8 Cl2 -179.74(9) . . . . ?
N1 C2 C1 O1 140.54(11) . . . . ?
C3 C2 C1 O1 -99.25(13) . . . . ?
N1 C2 C1 O2 -42.05(14) . . . . ?
C3 C2 C1 O2 78.16(13) . . . . ?

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
OW HW1 O1 0.874(6) 1.943(9) 2.7993(15) 166(2) 1_565 yes
OW HW2 O2 0.871(6) 2.020(10) 2.8580(15) 160.9(19) 2_456 yes
O3 H9 Cl2 0.84 2.52 3.0277(10) 119.5 . yes
O3 H9 O2 0.84 1.83 2.5998(13) 151.7 4_654 yes
N1 H7 O1 0.91 1.81 2.7218(13) 176.5 2_446 yes
N1 H6 Cl1 0.91 2.81 3.7100(10) 169.2 3_645 yes
N1 H8 OW 0.91 1.92 2.7977(15) 160.6 . yes
C3 H3 Cl2 0.99 2.91 3.6469(13) 132.4 3_755 yes
C9 H5 Cl1 0.95 2.95 3.5426(13) 122.1 1_545 yes

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046

