# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_114a
_database_code_depnum_ccdc_archive 'CCDC 1503377'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Cl N3 O2'
_chemical_formula_sum            'C16 H20 Cl N3 O2'
_chemical_formula_weight         321.80

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'
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'
O O 0.0106 0.0060 '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                   9.9885(4)
_cell_length_b                   8.6548(4)
_cell_length_c                   18.3874(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.256(4)
_cell_angle_gamma                90
_cell_volume                     1547.21(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1670
_cell_measurement_theta_min      2.7700
_cell_measurement_theta_max      27.4510

_exptl_crystal_description       plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            5413
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.614
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3074
_reflns_number_gt                2522
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0310P)²+0.5932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0050(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.70334(14) 0.44754(16) 0.37910(7) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.73846(17) 0.37593(19) 0.32258(9) 0.0208(4) Uani 1 1 d . . . . .
C3 C 0.85379(17) 0.2754(2) 0.33303(9) 0.0224(4) Uani 1 1 d . . . . .
H3A H 0.8788 0.2276 0.2915 0.027 Uiso 1 1 calc R U . . .
C4 C 0.92725(17) 0.24935(19) 0.40363(9) 0.0216(4) Uani 1 1 d . . . . .
Cl4 Cl 1.06738(4) 0.12520(5) 0.41685(2) 0.03163(15) Uani 1 1 d . . . . .
C5 C 0.89245(17) 0.31829(19) 0.46667(9) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.96318(17) 0.2949(2) 0.54208(9) 0.0229(4) Uani 1 1 d . . . . .
H6A H 1.0410 0.2287 0.5534 0.027 Uiso 1 1 calc R U . . .
C7 C 0.91974(17) 0.3674(2) 0.59833(9) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.80320(17) 0.4672(2) 0.58176(9) 0.0224(4) Uani 1 1 d . . . . .
C9 C 0.73492(18) 0.4917(2) 0.50925(9) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.6579 0.5592 0.4986 0.027 Uiso 1 1 calc R U . . .
C10 C 0.77780(17) 0.41768(19) 0.44993(9) 0.0205(4) Uani 1 1 d . . . . .
N11 N 0.65306(15) 0.39788(17) 0.25249(7) 0.0233(3) Uani 1 1 d . . . . .
C12 C 0.55685(18) 0.5266(2) 0.24228(9) 0.0262(4) Uani 1 1 d . . . . .
H12A H 0.6047 0.6226 0.2335 0.031 Uiso 1 1 calc R U . . .
H12B H 0.5224 0.5409 0.2882 0.031 Uiso 1 1 calc R U . . .
C13 C 0.43757(18) 0.4974(2) 0.17704(9) 0.0289(4) Uani 1 1 d . . . . .
H13A H 0.3847 0.4071 0.1881 0.035 Uiso 1 1 calc R U . . .
H13B H 0.3757 0.5882 0.1697 0.035 Uiso 1 1 calc R U . . .
N14 N 0.48383(15) 0.46835(17) 0.10885(7) 0.0247(3) Uani 1 1 d . . . . .
C15 C 0.5735(2) 0.3341(2) 0.12055(9) 0.0292(4) Uani 1 1 d . . . . .
H15A H 0.6049 0.3122 0.0743 0.035 Uiso 1 1 calc R U . . .
H15B H 0.5214 0.2431 0.1316 0.035 Uiso 1 1 calc R U . . .
C16 C 0.69724(19) 0.3594(2) 0.18431(9) 0.0318(4) Uani 1 1 d . . . . .
H16A H 0.7542 0.2646 0.1924 0.038 Uiso 1 1 calc R U . . .
H16B H 0.7541 0.4445 0.1716 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3652(2) 0.4417(2) 0.04703(10) 0.0366(5) Uani 1 1 d . . . . .
H17A H 0.3144 0.3511 0.0579 0.055 Uiso 1 1 calc R U . . .
H17B H 0.3967 0.4237 0.0010 0.055 Uiso 1 1 calc R U . . .
H17C H 0.3050 0.5325 0.0406 0.055 Uiso 1 1 calc R U . . .
O18 O 0.97869(12) 0.35314(15) 0.67293(6) 0.0292(3) Uani 1 1 d . . . . .
C19 C 1.0939(2) 0.2521(2) 0.69295(10) 0.0358(5) Uani 1 1 d . . . . .
H19B H 1.0671 0.1480 0.6741 0.054 Uiso 1 1 calc R U . . .
H19C H 1.1255 0.2489 0.7475 0.054 Uiso 1 1 calc R U . . .
H19A H 1.1684 0.2899 0.6710 0.054 Uiso 1 1 calc R U . . .
O20 O 0.76754(13) 0.53031(15) 0.64241(6) 0.0287(3) Uani 1 1 d . . . . .
C21 C 0.6482(2) 0.6264(2) 0.62779(10) 0.0330(4) Uani 1 1 d . . . . .
H21C H 0.6294 0.6612 0.6752 0.049 Uiso 1 1 calc R U . . .
H21B H 0.5692 0.5677 0.5997 0.049 Uiso 1 1 calc R U . . .
H21A H 0.6640 0.7164 0.5985 0.049 Uiso 1 1 calc R 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
N1 C2 1.325(2) . ?
N1 C10 1.368(2) . ?
C2 N11 1.386(2) . ?
C2 C3 1.421(2) . ?
C3 C4 1.356(2) . ?
C4 C5 1.416(2) . ?
C4 Cl4 1.7368(17) . ?
C5 C10 1.409(2) . ?
C5 C6 1.419(2) . ?
C6 C7 1.363(2) . ?
C7 O18 1.3685(19) . ?
C7 C8 1.425(2) . ?
C8 O20 1.360(2) . ?
C8 C9 1.368(2) . ?
C9 C10 1.413(2) . ?
N11 C12 1.455(2) . ?
N11 C16 1.460(2) . ?
C12 C13 1.506(2) . ?
C13 N14 1.454(2) . ?
N14 C15 1.453(2) . ?
N14 C17 1.460(2) . ?
C15 C16 1.512(2) . ?
O18 C19 1.425(2) . ?
O20 C21 1.428(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
C2 N1 C10 118.33(15) . . ?
N1 C2 N11 116.63(15) . . ?
N1 C2 C3 122.20(15) . . ?
N11 C2 C3 121.10(15) . . ?
C4 C3 C2 118.37(15) . . ?
C3 C4 C5 122.23(16) . . ?
C3 C4 Cl4 118.60(13) . . ?
C5 C4 Cl4 119.16(12) . . ?
C10 C5 C4 114.73(14) . . ?
C10 C5 C6 119.88(15) . . ?
C4 C5 C6 125.39(16) . . ?
C7 C6 C5 120.16(16) . . ?
C6 C7 O18 125.50(16) . . ?
C6 C7 C8 120.21(15) . . ?
O18 C7 C8 114.29(15) . . ?
O20 C8 C9 124.82(16) . . ?
O20 C8 C7 115.00(14) . . ?
C9 C8 C7 120.17(15) . . ?
C8 C9 C10 120.69(16) . . ?
N1 C10 C5 124.10(15) . . ?
N1 C10 C9 117.01(15) . . ?
C5 C10 C9 118.89(15) . . ?
C2 N11 C12 118.19(13) . . ?
C2 N11 C16 121.64(14) . . ?
C12 N11 C16 112.62(13) . . ?
N11 C12 C13 110.66(14) . . ?
N14 C13 C12 111.48(15) . . ?
C15 N14 C13 108.52(13) . . ?
C15 N14 C17 110.60(14) . . ?
C13 N14 C17 109.70(14) . . ?
N14 C15 C16 111.44(15) . . ?
N11 C16 C15 110.17(15) . . ?
C7 O18 C19 116.79(14) . . ?
C8 O20 C21 116.35(13) . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046

