# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1571324'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Ethyl 2-[5-(2,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl]-2-hydroxyacetate'
_chemical_name_common            triazole
_chemical_melting_point          158(2)
_chemical_formula_moiety         'C12 H11 Cl2 N3 O3'
_chemical_formula_sum            'C12 H11 Cl2 N3 O3'
_chemical_formula_weight         316.14

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4912(9)
_cell_length_b                   7.2015(5)
_cell_length_c                   16.5491(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.277(2)
_cell_angle_gamma                90
_cell_volume                     1347.53(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      26.36

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.492
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22992
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2369
_reflns_number_gt                2136
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+1.2330P] 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_number_reflns         2369
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.52734(5) 0.77068(9) 0.35923(4) 0.0445(2) Uani 1 1 d . . . . .
Cl2 Cl 0.41164(6) 0.74581(12) 0.03225(4) 0.0589(3) Uani 1 1 d . . . . .
O3 O 0.84237(15) 0.4690(2) 0.27064(10) 0.0437(4) Uani 1 1 d . . . . .
O1 O 0.85145(19) 0.4888(3) 0.48457(11) 0.0508(5) Uani 1 1 d . . . . .
O2 O 0.99141(16) 0.3925(3) 0.37205(12) 0.0503(5) Uani 1 1 d . . . . .
N3 N 0.90572(17) 0.8585(3) 0.44969(11) 0.0346(4) Uani 1 1 d . . . . .
N2 N 0.89253(19) 1.0301(3) 0.42061(12) 0.0387(5) Uani 1 1 d . . . . .
N1 N 0.81541(17) 1.0527(3) 0.35171(12) 0.0365(5) Uani 1 1 d . . . . .
C8 C 0.82960(19) 0.7604(3) 0.39563(13) 0.0286(5) Uani 1 1 d . . . . .
C1 C 0.68443(18) 0.8447(3) 0.25980(13) 0.0291(5) Uani 1 1 d . . . . .
C7 C 0.77349(18) 0.8816(3) 0.33425(13) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.56908(19) 0.7930(3) 0.26464(13) 0.0301(5) Uani 1 1 d . . . . .
C3 C 0.4851(2) 0.7615(3) 0.19501(14) 0.0345(5) Uani 1 1 d . . . . .
H3 H 0.4082 0.7280 0.1992 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8960(2) 0.4612(3) 0.34836(14) 0.0358(5) Uani 1 1 d . . . . .
C6 C 0.7138(2) 0.8630(3) 0.18197(13) 0.0364(5) Uani 1 1 d . . . . .
H6 H 0.7904 0.8968 0.1773 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8203(2) 0.5532(3) 0.40370(13) 0.0335(5) Uani 1 1 d . . . . .
C5 C 0.6313(2) 0.8317(4) 0.11164(14) 0.0413(6) Uani 1 1 d . . . . .
H5 H 0.6519 0.8447 0.0601 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5179(2) 0.7810(3) 0.11913(14) 0.0366(5) Uani 1 1 d . . . . .
C11 C 0.9010(3) 0.3786(5) 0.21016(17) 0.0551(7) Uani 1 1 d . . . . .
H11A H 0.9269 0.2551 0.2288 0.066 Uiso 1 1 calc R U . . .
H11B H 0.9698 0.4498 0.2022 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8154(3) 0.3673(5) 0.13258(18) 0.0694(9) Uani 1 1 d . . . . .
H12A H 0.7457 0.3032 0.1419 0.104 Uiso 1 1 calc R U . . .
H12B H 0.8502 0.3009 0.0925 0.104 Uiso 1 1 calc R U . . .
H12C H 0.7946 0.4903 0.1128 0.104 Uiso 1 1 calc R U . . .
H2A H 0.930(3) 1.118(4) 0.4426(17) 0.045(8) Uiso 1 1 d . . . . .
H1A H 0.898(3) 0.547(5) 0.505(2) 0.053(10) Uiso 1 1 d . . . . .
H9 H 0.740(2) 0.513(3) 0.3860(14) 0.028(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.725(2) . ?
Cl2 C4 1.731(2) . ?
O3 C10 1.324(3) . ?
O3 C11 1.456(3) . ?
O1 C9 1.401(3) . ?
O1 H1A 0.71(3) . ?
O2 C10 1.203(3) . ?
N3 N2 1.325(3) . ?
N3 C8 1.336(3) . ?
N2 N1 1.323(3) . ?
N2 H2A 0.81(3) . ?
N1 C7 1.336(3) . ?
C8 C7 1.405(3) . ?
C8 C9 1.504(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.395(3) . ?
C1 C7 1.479(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C10 C9 1.523(4) . ?
C6 C5 1.382(3) . ?
C6 H6 0.9300 . ?
C9 H9 0.96(2) . ?
C5 C4 1.380(4) . ?
C5 H5 0.9300 . ?
C11 C12 1.474(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C10 O3 C11 117.1(2) . . ?
C9 O1 H1A 108(3) . . ?
N2 N3 C8 103.34(17) . . ?
N1 N2 N3 116.32(18) . . ?
N1 N2 H2A 121(2) . . ?
N3 N2 H2A 123(2) . . ?
N2 N1 C7 103.48(18) . . ?
N3 C8 C7 108.49(19) . . ?
N3 C8 C9 120.90(19) . . ?
C7 C8 C9 130.50(19) . . ?
C2 C1 C6 117.90(19) . . ?
C2 C1 C7 121.63(19) . . ?
C6 C1 C7 120.47(19) . . ?
N1 C7 C8 108.37(18) . . ?
N1 C7 C1 121.01(19) . . ?
C8 C7 C1 130.61(19) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 Cl1 118.37(17) . . ?
C1 C2 Cl1 119.92(16) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
O2 C10 O3 125.0(2) . . ?
O2 C10 C9 124.6(2) . . ?
O3 C10 C9 110.39(19) . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C9 C8 113.75(19) . . ?
O1 C9 C10 110.7(2) . . ?
C8 C9 C10 108.71(19) . . ?
O1 C9 H9 105.1(14) . . ?
C8 C9 H9 110.6(14) . . ?
C10 C9 H9 107.8(14) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 Cl2 120.11(19) . . ?
C3 C4 Cl2 118.27(18) . . ?
O3 C11 C12 107.7(2) . . ?
O3 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.833
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053

