# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_ktm
_database_code_depnum_ccdc_archive 'CCDC 1524589'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cl2 N3 O2'
_chemical_formula_sum            'C14 H15 Cl2 N3 O2'
_chemical_formula_weight         328.19

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Triclinic
_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.531(3)
_cell_length_b                   8.903(5)
_cell_length_c                   13.722(7)
_cell_angle_alpha                101.653(9)
_cell_angle_beta                 93.785(10)
_cell_angle_gamma                103.989(10)
_cell_volume                     752.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    667
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      19.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3876
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2662
_reflns_number_gt                2104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1080P)²+0.0095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2593
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.50126(12) 0.27894(10) 0.23996(6) 0.0678(3) Uani 1 1 d . . .
Cl2 Cl 0.00257(13) 0.35271(12) 0.16244(6) 0.0748(4) Uani 1 1 d . . .
N1 N 0.0486(3) 0.5654(3) 0.33764(15) 0.0447(6) Uani 1 1 d . . .
O2 O 0.3087(3) 1.1048(3) 0.77691(14) 0.0555(6) Uani 1 1 d . . .
N2 N -0.2732(4) 0.5215(3) 0.38589(17) 0.0489(6) Uani 1 1 d . . .
N3 N 0.2385(4) 0.7918(3) 0.50580(16) 0.0443(5) Uani 1 1 d . . .
C3 C -0.0759(4) 0.6096(3) 0.40761(19) 0.0433(6) Uani 1 1 d . . .
O1 O -0.0474(4) 1.0602(3) 0.75551(18) 0.0798(8) Uani 1 1 d . . .
C5 C -0.0526(5) 0.8217(4) 0.5711(2) 0.0516(7) Uani 1 1 d . . .
H5 H -0.1944 0.8105 0.5812 0.062 Uiso 1 1 calc R . .
C2 C -0.2758(4) 0.4180(3) 0.2985(2) 0.0483(7) Uani 1 1 d . . .
C4 C 0.0214(4) 0.7375(3) 0.4932(2) 0.0443(6) Uani 1 1 d . . .
C6 C 0.1227(4) 0.9278(4) 0.6329(2) 0.0469(7) Uani 1 1 d . . .
C10 C 0.1160(5) 1.0372(4) 0.7272(2) 0.0528(7) Uani 1 1 d . . .
C7 C 0.3015(4) 0.9056(3) 0.5915(2) 0.0473(7) Uani 1 1 d . . .
H7 H 0.4411 0.9592 0.6176 0.057 Uiso 1 1 calc R . .
C11 C 0.3417(5) 1.1927(3) 0.88189(19) 0.0488(7) Uani 1 1 d . . .
C9 C 0.2712(5) 0.6537(4) 0.3393(2) 0.0563(8) Uani 1 1 d . . .
H9A H 0.2764 0.7427 0.3080 0.068 Uiso 1 1 calc R . .
H9B H 0.3473 0.5848 0.3019 0.068 Uiso 1 1 calc R . .
C1 C -0.0826(4) 0.4418(3) 0.2670(2) 0.0482(7) Uani 1 1 d . . .
C8 C 0.3737(4) 0.7126(4) 0.4449(2) 0.0542(7) Uani 1 1 d . . .
H8A H 0.3962 0.6242 0.4717 0.065 Uiso 1 1 calc R . .
H8B H 0.5110 0.7865 0.4472 0.065 Uiso 1 1 calc R . .
C12 C 0.5782(6) 1.2294(5) 0.9089(3) 0.0748(10) Uani 1 1 d . . .
H12A H 0.6227 1.1329 0.8940 0.112 Uiso 1 1 calc R . .
H12B H 0.6141 1.2774 0.9791 0.112 Uiso 1 1 calc R . .
H12C H 0.6488 1.3014 0.8708 0.112 Uiso 1 1 calc R . .
C13 C 0.2690(8) 1.3412(5) 0.8898(3) 0.0906(13) Uani 1 1 d . . .
H13A H 0.3365 1.4010 0.8445 0.136 Uiso 1 1 calc R . .
H13B H 0.3064 1.4040 0.9572 0.136 Uiso 1 1 calc R . .
H13C H 0.1176 1.3140 0.8730 0.136 Uiso 1 1 calc R . .
C14 C 0.2271(7) 1.0865(5) 0.9450(3) 0.0894(13) Uani 1 1 d . . .
H14A H 0.0764 1.0663 0.9283 0.134 Uiso 1 1 calc R . .
H14B H 0.2655 1.1379 1.0147 0.134 Uiso 1 1 calc R . .
H14C H 0.2665 0.9879 0.9323 0.134 Uiso 1 1 calc R . .


_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 1.705(3) . ?
Cl2 C1 1.690(3) . ?
N1 C3 1.358(3) . ?
N1 C1 1.374(4) . ?
N1 C9 1.473(4) . ?
O2 C10 1.329(4) . ?
O2 C11 1.468(3) . ?
N2 C3 1.315(4) . ?
N2 C2 1.353(4) . ?
N3 C7 1.354(4) . ?
N3 C4 1.370(4) . ?
N3 C8 1.461(4) . ?
C3 C4 1.446(4) . ?
O1 C10 1.208(3) . ?
C5 C4 1.363(4) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C2 C1 1.343(4) . ?
C6 C7 1.371(4) . ?
C6 C10 1.464(4) . ?
C7 H7 0.9300 . ?
C11 C13 1.496(5) . ?
C11 C12 1.504(5) . ?
C11 C14 1.509(4) . ?
C9 C8 1.489(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C3 N1 C1 105.8(2) . . ?
C3 N1 C9 122.7(2) . . ?
C1 N1 C9 131.1(2) . . ?
C10 O2 C11 122.3(2) . . ?
C3 N2 C2 105.1(2) . . ?
C7 N3 C4 109.4(2) . . ?
C7 N3 C8 126.9(2) . . ?
C4 N3 C8 122.7(2) . . ?
N2 C3 N1 111.8(2) . . ?
N2 C3 C4 129.9(2) . . ?
N1 C3 C4 118.3(3) . . ?
C4 C5 C6 107.7(2) . . ?
C4 C5 H5 126.1 . . ?
C6 C5 H5 126.1 . . ?
C1 C2 N2 111.1(3) . . ?
C1 C2 Cl1 126.7(2) . . ?
N2 C2 Cl1 122.2(2) . . ?
C5 C4 N3 107.6(2) . . ?
C5 C4 C3 134.8(3) . . ?
N3 C4 C3 117.6(2) . . ?
C7 C6 C5 107.5(2) . . ?
C7 C6 C10 126.5(3) . . ?
C5 C6 C10 125.9(3) . . ?
O1 C10 O2 125.1(3) . . ?
O1 C10 C6 123.0(3) . . ?
O2 C10 C6 111.9(2) . . ?
N3 C7 C6 107.8(2) . . ?
N3 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
O2 C11 C13 110.0(3) . . ?
O2 C11 C12 103.3(2) . . ?
C13 C11 C12 111.4(3) . . ?
O2 C11 C14 109.4(3) . . ?
C13 C11 C14 112.0(3) . . ?
C12 C11 C14 110.3(3) . . ?
N1 C9 C8 109.6(2) . . ?
N1 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
N1 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C2 C1 N1 106.2(2) . . ?
C2 C1 Cl2 131.2(2) . . ?
N1 C1 Cl2 122.6(2) . . ?
N3 C8 C9 109.9(2) . . ?
N3 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
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 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C3 N1 -0.5(3) . . . . ?
C2 N2 C3 C4 -178.7(3) . . . . ?
C1 N1 C3 N2 0.7(3) . . . . ?
C9 N1 C3 N2 174.4(3) . . . . ?
C1 N1 C3 C4 179.1(2) . . . . ?
C9 N1 C3 C4 -7.2(4) . . . . ?
C3 N2 C2 C1 0.2(3) . . . . ?
C3 N2 C2 Cl1 -179.7(2) . . . . ?
C6 C5 C4 N3 -0.7(3) . . . . ?
C6 C5 C4 C3 177.6(3) . . . . ?
C7 N3 C4 C5 1.5(3) . . . . ?
C8 N3 C4 C5 170.4(3) . . . . ?
C7 N3 C4 C3 -177.2(2) . . . . ?
C8 N3 C4 C3 -8.3(4) . . . . ?
N2 C3 C4 C5 -9.1(5) . . . . ?
N1 C3 C4 C5 172.9(3) . . . . ?
N2 C3 C4 N3 169.2(3) . . . . ?
N1 C3 C4 N3 -8.9(4) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C10 -177.7(3) . . . . ?
C11 O2 C10 O1 12.2(5) . . . . ?
C11 O2 C10 C6 -167.1(2) . . . . ?
C7 C6 C10 O1 173.9(3) . . . . ?
C5 C6 C10 O1 -9.2(5) . . . . ?
C7 C6 C10 O2 -6.8(4) . . . . ?
C5 C6 C10 O2 170.1(3) . . . . ?
C4 N3 C7 C6 -1.6(3) . . . . ?
C8 N3 C7 C6 -170.0(3) . . . . ?
C5 C6 C7 N3 1.1(3) . . . . ?
C10 C6 C7 N3 178.5(3) . . . . ?
C10 O2 C11 C13 -67.4(4) . . . . ?
C10 O2 C11 C12 173.6(3) . . . . ?
C10 O2 C11 C14 56.1(4) . . . . ?
C3 N1 C9 C8 37.2(4) . . . . ?
C1 N1 C9 C8 -150.8(3) . . . . ?
N2 C2 C1 N1 0.2(3) . . . . ?
Cl1 C2 C1 N1 -180.0(2) . . . . ?
N2 C2 C1 Cl2 -177.7(2) . . . . ?
Cl1 C2 C1 Cl2 2.2(4) . . . . ?
C3 N1 C1 C2 -0.5(3) . . . . ?
C9 N1 C1 C2 -173.5(3) . . . . ?
C3 N1 C1 Cl2 177.6(2) . . . . ?
C9 N1 C1 Cl2 4.6(4) . . . . ?
C7 N3 C8 C9 -154.7(3) . . . . ?
C4 N3 C8 C9 38.4(4) . . . . ?
N1 C9 C8 N3 -49.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.093
