##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;\
5-Chloromethyl-N-methyl-4-[(4-phenyl-1,2,3-triazol-1-\
yl)methyl]isoxazolidine-3-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H18 Cl N5 O2'
_chemical_formula_sum     'C15 H18 Cl N5 O2'
_chemical_formula_iupac     'C15 H18 Cl N5 O2'
_chemical_formula_weight     335.79
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.8355(2)
_cell_length_b     10.8865(2)
_cell_length_c     14.5653(2)
_cell_angle_alpha     90
_cell_angle_beta     106.481(2)
_cell_angle_gamma     90
_cell_volume     1647.54(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     16111
_cell_measurement_theta_min     4.0570
_cell_measurement_theta_max     66.7160
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.354
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     2.203
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
(CrysAlis Pro; Agilent, 2013)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.518
_exptl_absorpt_correction_T_max     0.721
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Agilent Xcalibur (Atlas, Gemini ultra)'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4678
_diffrn_reflns_number     33842
_diffrn_reflns_av_R_equivalents     0.0504
_diffrn_reflns_theta_min     3.164
_diffrn_reflns_theta_max     66.709
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details     ?
_reflns_number_total     5824
_reflns_number_gt     5486
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0392
_refine_ls_R_factor_gt     0.0364
_refine_ls_wR_factor_gt     0.0940
_refine_ls_wR_factor_ref     0.0977
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_restrained_S_all     1.025
_refine_ls_number_reflns     5824
_refine_ls_number_parameters     431
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0615P)²+0.2009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.174
_refine_diff_density_min     -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 2460 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     -0.012(6)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_structure_solution
;
SIR2004 (Burla et al.,  2005)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.13936(13) 0.47609(9) 0.24767(6) 0.0825(3) Uani d 1 . .
    Cl Cl2 0.73439(12) 0.41058(9) 0.36164(7) 0.0820(3) Uani d 1 . .
    O O1 0.2546(2) 0.3689(2) 0.45141(15) 0.0517(5) Uani d 1 . .
    O O2 0.0503(3) 0.2666(3) 0.6455(2) 0.0865(9) Uani d 1 . .
    O O3 0.6733(2) 0.28927(18) 0.53585(18) 0.0581(5) Uani d 1 . .
    O O4 0.5087(3) 0.3654(3) 0.7570(2) 0.0739(7) Uani d 1 . .
    N N1 0.2650(3) 0.2979(3) 0.53684(19) 0.0517(6) Uani d 1 . .
    H H1N 0.205(4) 0.247(4) 0.514(3) 0.055(11) Uiso d 1 . .
    N N2 0.0602(2) 0.6113(2) 0.63212(17) 0.0419(5) Uani d 1 . .
    N N3 -0.0647(3) 0.5920(3) 0.6239(2) 0.0570(7) Uani d 1 . .
    N N4 -0.0824(2) 0.6133(3) 0.7076(2) 0.0562(7) Uani d 1 . .
    N N5 0.2516(3) 0.2708(3) 0.7437(2) 0.0620(7) Uani d 1 . .
    H H5N 0.334(4) 0.295(4) 0.751(3) 0.064(11) Uiso d 1 . .
    N N6 0.7486(3) 0.3170(3) 0.6325(2) 0.0555(6) Uani d 1 . .
    H H6N 0.818(4) 0.364(4) 0.628(3) 0.068(11) Uiso d 1 . .
    N N7 0.5466(2) 0.6450(2) 0.67354(17) 0.0437(5) Uani d 1 . .
    N N8 0.4305(2) 0.6292(2) 0.68824(19) 0.0511(6) Uani d 1 . .
    N N9 0.4348(2) 0.6829(3) 0.76918(19) 0.0517(6) Uani d 1 . .
    N N10 0.6278(4) 0.2017(3) 0.7438(3) 0.0762(10) Uani d 1 . .
    H H10N 0.685(4) 0.183(4) 0.724(3) 0.060(12) Uiso d 1 . .
    C C1 0.1254(4) 0.5279(3) 0.3610(2) 0.0621(9) Uani d 1 . .
    H H1A 0.1957 0.5835 0.3897 0.075 Uiso calc 1 . .
    H H1B 0.0453 0.5727 0.3514 0.075 Uiso calc 1 . .
    C C2 0.1281(3) 0.4226(3) 0.4275(2) 0.0432(6) Uani d 1 . .
    H H2 0.0650 0.3611 0.3947 0.052 Uiso calc 1 . .
    C C3 0.2096(3) 0.3809(2) 0.5948(2) 0.0431(6) Uani d 1 . .
    H H3 0.2765 0.4371 0.6309 0.052 Uiso calc 1 . .
    C C4 0.1038(3) 0.4550(2) 0.52417(19) 0.0406(6) Uani d 1 . .
    H H4 0.0199 0.4219 0.5246 0.049 Uiso calc 1 . .
    C C5 0.1076(3) 0.5915(3) 0.5481(2) 0.0428(6) Uani d 1 . .
    H H5A 0.1952 0.6217 0.5614 0.051 Uiso calc 1 . .
    H H5B 0.0545 0.6367 0.4938 0.051 Uiso calc 1 . .
    C C6 0.1227(3) 0.6479(3) 0.7208(2) 0.0423(6) Uani d 1 . .
    H H6 0.2093 0.6685 0.7443 0.051 Uiso calc 1 . .
    C C7 0.0312(3) 0.6486(3) 0.7694(2) 0.0452(6) Uani d 1 . .
    C C8 0.0431(3) 0.6797(3) 0.8698(2) 0.0544(8) Uani d 1 . .
    C C9 -0.0314(4) 0.6204(5) 0.9194(3) 0.0740(11) Uani d 1 . .
    H H9 -0.0916 0.5621 0.8883 0.089 Uiso calc 1 . .
    C C10 -0.0172(5) 0.6469(6) 1.0144(3) 0.0953(16) Uani d 1 . .
    H H10 -0.0682 0.6065 1.0465 0.114 Uiso calc 1 . .
    C C11 0.0695(6) 0.7304(6) 1.0614(3) 0.0981(17) Uani d 1 . .
    H H11 0.0791 0.7470 1.1257 0.118 Uiso calc 1 . .
    C C12 0.1425(5) 0.7898(6) 1.0141(3) 0.1006(16) Uani d 1 . .
    H H12 0.2021 0.8478 1.0464 0.121 Uiso calc 1 . .
    C C13 0.1303(4) 0.7658(5) 0.9179(3) 0.0772(11) Uani d 1 . .
    H H13 0.1809 0.8079 0.8865 0.093 Uiso calc 1 . .
    C C14 0.1629(3) 0.3015(3) 0.6648(2) 0.0510(7) Uani d 1 . .
    C C15 0.2257(5) 0.1867(4) 0.8142(3) 0.0798(12) Uani d 1 . .
    H H15A 0.3024 0.1763 0.8663 0.120 Uiso calc 1 . .
    H H15B 0.1586 0.2200 0.8380 0.120 Uiso calc 1 . .
    H H15C 0.1990 0.1086 0.7847 0.120 Uiso calc 1 . .
    C C16 0.6835(3) 0.4838(3) 0.4541(2) 0.0504(7) Uani d 1 . .
    H H16A 0.7586 0.5112 0.5038 0.060 Uiso calc 1 . .
    H H16B 0.6328 0.5557 0.4280 0.060 Uiso calc 1 . .
    C C17 0.6038(3) 0.3994(3) 0.4983(2) 0.0475(6) Uani d 1 . .
    H H17 0.5246 0.3770 0.4492 0.057 Uiso calc 1 . .
    C C18 0.6645(3) 0.3930(3) 0.6704(2) 0.0460(6) Uani d 1 . .
    H H18 0.7162 0.4560 0.7121 0.055 Uiso calc 1 . .
    C C19 0.5684(3) 0.4565(2) 0.5844(2) 0.0412(6) Uani d 1 . .
    H H19 0.4811 0.4305 0.5823 0.049 Uiso calc 1 . .
    C C20 0.5741(3) 0.5967(3) 0.5880(2) 0.0465(6) Uani d 1 . .
    H H20A 0.6591 0.6235 0.5869 0.056 Uiso calc 1 . .
    H H20B 0.5121 0.6297 0.5316 0.056 Uiso calc 1 . .
    C C21 0.6248(3) 0.7090(3) 0.7458(2) 0.0465(6) Uani d 1 . .
    H H21 0.7097 0.7316 0.7526 0.056 Uiso calc 1 . .
    C C22 0.5530(3) 0.7341(3) 0.8071(2) 0.0460(6) Uani d 1 . .
    C C23 0.5844(3) 0.8079(3) 0.8951(2) 0.0516(7) Uani d 1 . .
    C C24 0.7070(4) 0.8516(3) 0.9358(2) 0.0605(8) Uani d 1 . .
    H H24 0.7733 0.8293 0.9104 0.073 Uiso calc 1 . .
    C C25 0.7319(5) 0.9290(4) 1.0149(3) 0.0801(12) Uani d 1 . .
    H H25 0.8147 0.9595 1.0407 0.096 Uiso calc 1 . .
    C C26 0.6387(6) 0.9607(5) 1.0550(3) 0.0882(13) Uani d 1 . .
    H H26 0.6572 1.0113 1.1086 0.106 Uiso calc 1 . .
    C C27 0.5183(6) 0.9182(7) 1.0163(4) 0.1109(19) Uani d 1 . .
    H H27 0.4532 0.9412 1.0429 0.133 Uiso calc 1 . .
    C C28 0.4899(5) 0.8403(6) 0.9372(3) 0.0947(16) Uani d 1 . .
    H H28 0.4069 0.8100 0.9126 0.114 Uiso calc 1 . .
    C C29 0.5929(3) 0.3181(3) 0.7277(2) 0.0535(7) Uani d 1 . .
    C C30 0.5727(6) 0.1189(5) 0.7996(5) 0.112(2) Uani d 1 . .
    H H30A 0.6119 0.0394 0.8020 0.168 Uiso calc 1 . .
    H H30B 0.5879 0.1505 0.8633 0.168 Uiso calc 1 . .
    H H30C 0.4817 0.1119 0.7701 0.168 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C1 . 1.791(3) ?
    Cl2 C16 . 1.782(3) ?
    O1 C2 . 1.439(3) ?
    O1 N1 . 1.442(3) ?
    O2 C14 . 1.231(4) ?
    O3 C17 . 1.439(4) ?
    O3 N6 . 1.445(4) ?
    O4 C29 . 1.226(4) ?
    N1 C3 . 1.476(4) ?
    N1 H1N . 0.85(4) ?
    N2 C6 . 1.338(4) ?
    N2 N3 . 1.340(4) ?
    N2 C5 . 1.471(3) ?
    N3 N4 . 1.307(4) ?
    N4 C7 . 1.359(4) ?
    N5 C14 . 1.316(5) ?
    N5 C15 . 1.461(5) ?
    N5 H5N . 0.91(4) ?
    N6 C18 . 1.452(4) ?
    N6 H6N . 0.93(5) ?
    N7 C21 . 1.343(4) ?
    N7 N8 . 1.346(3) ?
    N7 C20 . 1.459(4) ?
    N8 N9 . 1.305(4) ?
    N9 C22 . 1.362(4) ?
    N10 C29 . 1.324(5) ?
    N10 C30 . 1.451(5) ?
    N10 H10N . 0.78(4) ?
    C1 C2 . 1.495(4) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C4 . 1.544(4) ?
    C2 H2 . 0.9800 ?
    C3 C14 . 1.528(4) ?
    C3 C4 . 1.534(4) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.525(4) ?
    C4 H4 . 0.9800 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.372(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.471(4) ?
    C8 C13 . 1.374(6) ?
    C8 C9 . 1.386(5) ?
    C9 C10 . 1.378(7) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.347(9) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.352(8) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.393(6) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 C17 . 1.523(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C19 . 1.542(4) ?
    C17 H17 . 0.9800 ?
    C18 C29 . 1.525(4) ?
    C18 C19 . 1.546(4) ?
    C18 H18 . 0.9800 ?
    C19 C20 . 1.528(4) ?
    C19 H19 . 0.9800 ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 C22 . 1.368(4) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.468(4) ?
    C23 C24 . 1.377(5) ?
    C23 C28 . 1.380(5) ?
    C24 C25 . 1.391(5) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.346(7) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.348(8) ?
    C26 H26 . 0.9300 ?
    C27 C28 . 1.393(7) ?
    C27 H27 . 0.9300 ?
    C28 H28 . 0.9300 ?
    C30 H30A . 0.9600 ?
    C30 H30B . 0.9600 ?
    C30 H30C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 N1 . . 105.2(2) ?
    C17 O3 N6 . . 106.7(2) ?
    O1 N1 C3 . . 102.7(2) ?
    O1 N1 H1N . . 98(3) ?
    C3 N1 H1N . . 104(3) ?
    C6 N2 N3 . . 110.8(2) ?
    C6 N2 C5 . . 130.2(2) ?
    N3 N2 C5 . . 119.0(2) ?
    N4 N3 N2 . . 107.5(2) ?
    N3 N4 C7 . . 108.8(2) ?
    C14 N5 C15 . . 122.3(3) ?
    C14 N5 H5N . . 118(3) ?
    C15 N5 H5N . . 119(3) ?
    O3 N6 C18 . . 104.3(2) ?
    O3 N6 H6N . . 107(2) ?
    C18 N6 H6N . . 109(3) ?
    C21 N7 N8 . . 110.6(2) ?
    C21 N7 C20 . . 128.3(2) ?
    N8 N7 C20 . . 121.1(2) ?
    N9 N8 N7 . . 107.0(2) ?
    N8 N9 C22 . . 109.7(2) ?
    C29 N10 C30 . . 123.5(4) ?
    C29 N10 H10N . . 113(3) ?
    C30 N10 H10N . . 123(3) ?
    C2 C1 Cl1 . . 111.4(2) ?
    C2 C1 H1A . . 109.3 ?
    Cl1 C1 H1A . . 109.3 ?
    C2 C1 H1B . . 109.3 ?
    Cl1 C1 H1B . . 109.3 ?
    H1A C1 H1B . . 108.0 ?
    O1 C2 C1 . . 108.1(3) ?
    O1 C2 C4 . . 105.6(2) ?
    C1 C2 C4 . . 116.0(2) ?
    O1 C2 H2 . . 109.0 ?
    C1 C2 H2 . . 109.0 ?
    C4 C2 H2 . . 109.0 ?
    N1 C3 C14 . . 107.5(2) ?
    N1 C3 C4 . . 106.6(2) ?
    C14 C3 C4 . . 114.8(2) ?
    N1 C3 H3 . . 109.3 ?
    C14 C3 H3 . . 109.3 ?
    C4 C3 H3 . . 109.3 ?
    C5 C4 C3 . . 113.1(2) ?
    C5 C4 C2 . . 115.5(2) ?
    C3 C4 C2 . . 101.7(2) ?
    C5 C4 H4 . . 108.7 ?
    C3 C4 H4 . . 108.7 ?
    C2 C4 H4 . . 108.7 ?
    N2 C5 C4 . . 109.9(2) ?
    N2 C5 H5A . . 109.7 ?
    C4 C5 H5A . . 109.7 ?
    N2 C5 H5B . . 109.7 ?
    C4 C5 H5B . . 109.7 ?
    H5A C5 H5B . . 108.2 ?
    N2 C6 C7 . . 104.9(2) ?
    N2 C6 H6 . . 127.5 ?
    C7 C6 H6 . . 127.5 ?
    N4 C7 C6 . . 107.9(3) ?
    N4 C7 C8 . . 122.1(3) ?
    C6 C7 C8 . . 130.0(3) ?
    C13 C8 C9 . . 118.0(4) ?
    C13 C8 C7 . . 121.2(3) ?
    C9 C8 C7 . . 120.8(4) ?
    C10 C9 C8 . . 120.6(5) ?
    C10 C9 H9 . . 119.7 ?
    C8 C9 H9 . . 119.7 ?
    C11 C10 C9 . . 121.1(5) ?
    C11 C10 H10 . . 119.5 ?
    C9 C10 H10 . . 119.5 ?
    C10 C11 C12 . . 119.2(4) ?
    C10 C11 H11 . . 120.4 ?
    C12 C11 H11 . . 120.4 ?
    C11 C12 C13 . . 121.4(5) ?
    C11 C12 H12 . . 119.3 ?
    C13 C12 H12 . . 119.3 ?
    C8 C13 C12 . . 119.8(5) ?
    C8 C13 H13 . . 120.1 ?
    C12 C13 H13 . . 120.1 ?
    O2 C14 N5 . . 123.5(3) ?
    O2 C14 C3 . . 121.1(3) ?
    N5 C14 C3 . . 115.4(3) ?
    N5 C15 H15A . . 109.5 ?
    N5 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    N5 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C17 C16 Cl2 . . 112.6(2) ?
    C17 C16 H16A . . 109.1 ?
    Cl2 C16 H16A . . 109.1 ?
    C17 C16 H16B . . 109.1 ?
    Cl2 C16 H16B . . 109.1 ?
    H16A C16 H16B . . 107.8 ?
    O3 C17 C16 . . 111.4(2) ?
    O3 C17 C19 . . 104.5(2) ?
    C16 C17 C19 . . 113.7(2) ?
    O3 C17 H17 . . 109.0 ?
    C16 C17 H17 . . 109.0 ?
    C19 C17 H17 . . 109.0 ?
    N6 C18 C29 . . 112.0(3) ?
    N6 C18 C19 . . 107.3(2) ?
    C29 C18 C19 . . 110.6(2) ?
    N6 C18 H18 . . 109.0 ?
    C29 C18 H18 . . 109.0 ?
    C19 C18 H18 . . 109.0 ?
    C20 C19 C17 . . 114.4(2) ?
    C20 C19 C18 . . 114.1(2) ?
    C17 C19 C18 . . 102.3(2) ?
    C20 C19 H19 . . 108.6 ?
    C17 C19 H19 . . 108.6 ?
    C18 C19 H19 . . 108.6 ?
    N7 C20 C19 . . 111.9(2) ?
    N7 C20 H20A . . 109.2 ?
    C19 C20 H20A . . 109.2 ?
    N7 C20 H20B . . 109.2 ?
    C19 C20 H20B . . 109.2 ?
    H20A C20 H20B . . 107.9 ?
    N7 C21 C22 . . 105.4(3) ?
    N7 C21 H21 . . 127.3 ?
    C22 C21 H21 . . 127.3 ?
    N9 C22 C21 . . 107.3(3) ?
    N9 C22 C23 . . 122.4(3) ?
    C21 C22 C23 . . 130.1(3) ?
    C24 C23 C28 . . 117.8(3) ?
    C24 C23 C22 . . 121.5(3) ?
    C28 C23 C22 . . 120.7(3) ?
    C23 C24 C25 . . 120.2(4) ?
    C23 C24 H24 . . 119.9 ?
    C25 C24 H24 . . 119.9 ?
    C26 C25 C24 . . 121.4(4) ?
    C26 C25 H25 . . 119.3 ?
    C24 C25 H25 . . 119.3 ?
    C25 C26 C27 . . 119.2(4) ?
    C25 C26 H26 . . 120.4 ?
    C27 C26 H26 . . 120.4 ?
    C26 C27 C28 . . 121.0(5) ?
    C26 C27 H27 . . 119.5 ?
    C28 C27 H27 . . 119.5 ?
    C23 C28 C27 . . 120.4(5) ?
    C23 C28 H28 . . 119.8 ?
    C27 C28 H28 . . 119.8 ?
    O4 C29 N10 . . 122.9(3) ?
    O4 C29 C18 . . 120.7(3) ?
    N10 C29 C18 . . 116.4(3) ?
    N10 C30 H30A . . 109.5 ?
    N10 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    N10 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 O1 N1 C3 . . . . -43.5(3) ?
    C6 N2 N3 N4 . . . . -1.5(4) ?
    C5 N2 N3 N4 . . . . 178.8(3) ?
    N2 N3 N4 C7 . . . . 1.1(4) ?
    C17 O3 N6 C18 . . . . 39.2(3) ?
    C21 N7 N8 N9 . . . . 0.0(3) ?
    C20 N7 N8 N9 . . . . -179.4(2) ?
    N7 N8 N9 C22 . . . . 0.3(3) ?
    N1 O1 C2 C1 . . . . 161.7(2) ?
    N1 O1 C2 C4 . . . . 36.9(3) ?
    Cl1 C1 C2 O1 . . . . 67.3(3) ?
    Cl1 C1 C2 C4 . . . . -174.4(2) ?
    O1 N1 C3 C14 . . . . 156.5(2) ?
    O1 N1 C3 C4 . . . . 32.9(3) ?
    N1 C3 C4 C5 . . . . -135.3(2) ?
    C14 C3 C4 C5 . . . . 105.8(3) ?
    N1 C3 C4 C2 . . . . -10.8(3) ?
    C14 C3 C4 C2 . . . . -129.7(2) ?
    O1 C2 C4 C5 . . . . 107.6(3) ?
    C1 C2 C4 C5 . . . . -12.1(4) ?
    O1 C2 C4 C3 . . . . -15.3(3) ?
    C1 C2 C4 C3 . . . . -135.0(3) ?
    C6 N2 C5 C4 . . . . 111.7(3) ?
    N3 N2 C5 C4 . . . . -68.7(3) ?
    C3 C4 C5 N2 . . . . -73.6(3) ?
    C2 C4 C5 N2 . . . . 169.7(2) ?
    N3 N2 C6 C7 . . . . 1.2(3) ?
    C5 N2 C6 C7 . . . . -179.2(3) ?
    N3 N4 C7 C6 . . . . -0.4(4) ?
    N3 N4 C7 C8 . . . . 179.8(3) ?
    N2 C6 C7 N4 . . . . -0.5(3) ?
    N2 C6 C7 C8 . . . . 179.3(3) ?
    N4 C7 C8 C13 . . . . -148.7(4) ?
    C6 C7 C8 C13 . . . . 31.5(5) ?
    N4 C7 C8 C9 . . . . 33.0(5) ?
    C6 C7 C8 C9 . . . . -146.8(4) ?
    C13 C8 C9 C10 . . . . -0.5(6) ?
    C7 C8 C9 C10 . . . . 177.9(4) ?
    C8 C9 C10 C11 . . . . -0.3(8) ?
    C9 C10 C11 C12 . . . . 0.7(8) ?
    C10 C11 C12 C13 . . . . -0.4(9) ?
    C9 C8 C13 C12 . . . . 0.8(6) ?
    C7 C8 C13 C12 . . . . -177.5(4) ?
    C11 C12 C13 C8 . . . . -0.4(8) ?
    C15 N5 C14 O2 . . . . 3.2(6) ?
    C15 N5 C14 C3 . . . . -174.6(3) ?
    N1 C3 C14 O2 . . . . -94.4(4) ?
    C4 C3 C14 O2 . . . . 24.0(4) ?
    N1 C3 C14 N5 . . . . 83.4(3) ?
    C4 C3 C14 N5 . . . . -158.2(3) ?
    N6 O3 C17 C16 . . . . 86.8(3) ?
    N6 O3 C17 C19 . . . . -36.4(3) ?
    Cl2 C16 C17 O3 . . . . 57.2(3) ?
    Cl2 C16 C17 C19 . . . . 175.0(2) ?
    O3 N6 C18 C29 . . . . 96.0(3) ?
    O3 N6 C18 C19 . . . . -25.6(3) ?
    O3 C17 C19 C20 . . . . 143.0(2) ?
    C16 C17 C19 C20 . . . . 21.3(4) ?
    O3 C17 C19 C18 . . . . 19.1(3) ?
    C16 C17 C19 C18 . . . . -102.6(3) ?
    N6 C18 C19 C20 . . . . -120.2(3) ?
    C29 C18 C19 C20 . . . . 117.4(3) ?
    N6 C18 C19 C17 . . . . 4.0(3) ?
    C29 C18 C19 C17 . . . . -118.5(3) ?
    C21 N7 C20 C19 . . . . 116.5(3) ?
    N8 N7 C20 C19 . . . . -64.3(4) ?
    C17 C19 C20 N7 . . . . -176.9(2) ?
    C18 C19 C20 N7 . . . . -59.5(3) ?
    N8 N7 C21 C22 . . . . -0.3(3) ?
    C20 N7 C21 C22 . . . . 179.0(3) ?
    N8 N9 C22 C21 . . . . -0.5(4) ?
    N8 N9 C22 C23 . . . . 175.9(3) ?
    N7 C21 C22 N9 . . . . 0.5(3) ?
    N7 C21 C22 C23 . . . . -175.6(3) ?
    N9 C22 C23 C24 . . . . 175.4(3) ?
    C21 C22 C23 C24 . . . . -9.0(5) ?
    N9 C22 C23 C28 . . . . -7.6(5) ?
    C21 C22 C23 C28 . . . . 168.0(4) ?
    C28 C23 C24 C25 . . . . -2.0(6) ?
    C22 C23 C24 C25 . . . . 175.1(3) ?
    C23 C24 C25 C26 . . . . 1.6(6) ?
    C24 C25 C26 C27 . . . . -1.2(8) ?
    C25 C26 C27 C28 . . . . 1.3(10) ?
    C24 C23 C28 C27 . . . . 2.1(8) ?
    C22 C23 C28 C27 . . . . -175.0(5) ?
    C26 C27 C28 C23 . . . . -1.8(10) ?
    C30 N10 C29 O4 . . . . -1.5(7) ?
    C30 N10 C29 C18 . . . . 177.9(5) ?
    N6 C18 C29 O4 . . . . -172.9(3) ?
    C19 C18 C29 O4 . . . . -53.2(4) ?
    N6 C18 C29 N10 . . . . 7.6(4) ?
    C19 C18 C29 N10 . . . . 127.3(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N10 H10N N6 . 0.78(4) 2.21(4) 2.668(4) 118(4)
    N5 H5N O4 . 0.91(4) 2.02(4) 2.925(4) 173(4)
    C6 H6 N9 . 0.93 2.37 3.275(4) 164
    C1 H1B O2 2_556 0.97 2.36 3.208(4) 146
    C5 H5B O2 2_556 0.97 2.47 3.432(4) 171
    C16 H16A N3 1_655 0.97 2.37 3.335(4) 176
    C2 H2 Cg2 2_546 0.95 2.90 3.806(3) 154
_shelxl_version_number     2014/6
data_global
_journal_date_recd_electronic     2016-02-10
_journal_date_accepted     2016-02-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue      3
_journal_page_first     378
_journal_page_last     381
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016002784
_journal_coeditor_code     SU5281
_publ_contact_author_name     'Brahmi Jihed '
_publ_contact_author_address
;
Université de Monastir, Laboratoire de Synthèse Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
_publ_contact_author_email     'jihedbrahmi85@live.fr'
_publ_contact_author_fax     '0021673500278'
_publ_contact_author_phone     '0021694799167'
_publ_section_title
;\
Crystal structure of
5-chloromethyl-N-methyl-4-[(4-phenyl-1,2,3-triazol-1-yl)methyl]\
isoxazolidine-3-carboxamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Brahmi, Jihed ' .
;
Université de Monastir, Laboratoire de Synthèse Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
    'Nasri, Soumaya ' .
;
Laboratoire de Physico-chimie des Matériaux
Faculté des Sciences de Monastir
Avenue de l'Environnement
5019 Monastir
University of Monastir
Tunisia
;
    'Aouadi, Kaïss ' .
;
Université de Monastir, Laboratoire de Synthèse Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
    'Jeanneau, Erwann' .
;\
Université Lyon 1, Centre de Diffractométrie Henri Longchambon Bâtiment \
305, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France
;
    'Vidal, Sébastien' .
;\
Université de Lyon, Institut de Chimie et Biochimie Moléculaires et \
Supramoléculaires, UMR CNRS 5246, Laboratoire de Chimie Organique \
2-Glycochimie, Bâtiment Curien, 43 boulevard du 11 Novembre 1918,
F-69622 Villeurbanne, France
;
    'Msaddek, Moncef ' .
;
Université de Monastir, Laboratoire de Synthèse Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
_publ_section_synopsis
;
The title compound crystallized with two independent molecules in the
asymmetric unit. Each molecule has three stereogenic centres with
configurations 2(S), 3(S) and 4(R), confirmed by resonant
scattering.
;
