# 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_wl72
_database_code_depnum_ccdc_archive 'CCDC 1528178'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2017-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15.50 H20 Cl N O2'
_chemical_formula_weight         287.77

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.8393(9)
_cell_length_b                   10.8367(12)
_cell_length_c                   17.382(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.666(5)
_cell_angle_gamma                90
_cell_volume                     1471.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12831
_cell_measurement_theta_min      2.217
_cell_measurement_theta_max      27.465

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'Phi scan and Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12831
_diffrn_reflns_av_unetI/netI     0.1108
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3347
_reflns_number_gt                1698
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0545P)²+1.1201P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3347
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1588
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O1 O 0.1652(3) 0.4127(2) 0.98087(12) 0.0312(6) Uani 1 1 d . . . . .
O2 O -0.0875(3) 0.4304(2) 0.91188(14) 0.0359(7) Uani 1 1 d . . . . .
H2 H -0.104(5) 0.479(4) 0.947(2) 0.040(12) Uiso 1 1 d . . . . .
N1 N 0.0413(3) 0.1418(2) 0.67549(14) 0.0248(6) Uani 1 1 d . . . . .
C1 C 0.0687(4) 0.3823(3) 0.92333(17) 0.0222(7) Uani 1 1 d . . . . .
C2 C 0.1137(4) 0.2982(3) 0.86568(16) 0.0200(7) Uani 1 1 d . . . . .
C3 C 0.0119(4) 0.2676(3) 0.79664(17) 0.0211(7) Uani 1 1 d . . . . .
H3 H -0.100(4) 0.293(3) 0.7828(16) 0.020(8) Uiso 1 1 d . . . . .
C4 C 0.1023(4) 0.1899(3) 0.75296(16) 0.0205(7) Uani 1 1 d . . . . .
C5 C 0.2683(4) 0.1655(3) 0.79166(17) 0.0202(7) Uani 1 1 d . . . . .
C6 C 0.4121(4) 0.0954(3) 0.77494(19) 0.0263(8) Uani 1 1 d . . . . .
H6 H 0.415(4) 0.055(3) 0.7291(19) 0.029(9) Uiso 1 1 d . . . . .
C7 C 0.5545(5) 0.0942(3) 0.8271(2) 0.0318(9) Uani 1 1 d . . . . .
H7 H 0.650(4) 0.048(3) 0.8131(19) 0.030(9) Uiso 1 1 d . . . . .
C8 C 0.5586(5) 0.1596(4) 0.8963(2) 0.0343(9) Uani 1 1 d . . . . .
H8 H 0.658(4) 0.160(3) 0.9286(19) 0.033(10) Uiso 1 1 d . . . . .
C9 C 0.4196(4) 0.2280(3) 0.91429(19) 0.0259(8) Uani 1 1 d . . . . .
H9 H 0.416(4) 0.271(3) 0.958(2) 0.042(11) Uiso 1 1 d . . . . .
C10 C 0.2728(4) 0.2336(3) 0.86276(16) 0.0194(7) Uani 1 1 d . . . . .
C11 C -0.1360(5) 0.1865(4) 0.6517(2) 0.0317(9) Uani 1 1 d . . . . .
H11C H -0.139(4) 0.276(3) 0.6506(16) 0.022(9) Uiso 1 1 d . . . . .
H11B H -0.168(4) 0.151(3) 0.605(2) 0.041(10) Uiso 1 1 d . . . . .
H11A H -0.215(4) 0.155(3) 0.6881(17) 0.011(8) Uiso 1 1 d . . . . .
C12 C 0.1615(5) 0.1832(4) 0.6152(2) 0.0344(9) Uani 1 1 d . . . . .
H12B H 0.274(4) 0.139(3) 0.6296(17) 0.022(9) Uiso 1 1 d . . . . .
H12A H 0.119(4) 0.148(3) 0.567(2) 0.044(10) Uiso 1 1 d . . . . .
C13 C 0.1782(7) 0.3207(4) 0.6083(3) 0.0505(12) Uani 1 1 d . . . . .
H13C H 0.272(5) 0.333(4) 0.574(2) 0.054(12) Uiso 1 1 d . . . . .
H13B H 0.207(5) 0.356(4) 0.662(3) 0.067(14) Uiso 1 1 d . . . . .
H13A H 0.079(5) 0.364(4) 0.590(2) 0.047(13) Uiso 1 1 d . . . . .
C14 C 0.0410(5) 0.0004(3) 0.6744(2) 0.0316(9) Uani 1 1 d . . . . .
H14B H -0.004(4) -0.021(3) 0.622(2) 0.045(11) Uiso 1 1 d . . . . .
H14A H 0.157(4) -0.024(3) 0.6790(18) 0.027(9) Uiso 1 1 d . . . . .
C15 C -0.0632(5) -0.0572(4) 0.7328(2) 0.0336(9) Uani 1 1 d . . . . .
H15C H -0.176(5) -0.047(3) 0.722(2) 0.038(11) Uiso 1 1 d . . . . .
H15B H -0.029(4) -0.027(3) 0.785(2) 0.040(11) Uiso 1 1 d . . . . .
H15A H -0.043(5) -0.150(4) 0.734(2) 0.054(12) Uiso 1 1 d . . . . .
C16 C 0.4757(12) 0.5466(8) 0.5429(5) 0.038(2) Uani 0.5 1 d . . P . .
H16A H 0.549(10) 0.600(8) 0.559(4) 0.05(3) Uiso 0.5 1 d . . P . .
H16B H 0.401(9) 0.527(6) 0.572(4) 0.02(2) Uiso 0.5 1 d . . P . .
CL1 Cl 0.60905(16) 0.40953(12) 0.53981(7) 0.0701(4) 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
O1 C1 1.248(4) . ?
O2 C1 1.331(4) . ?
O2 H2 0.82(4) . ?
N1 C4 1.486(4) . ?
N1 C11 1.497(4) . ?
N1 C14 1.533(4) . ?
N1 C12 1.533(4) . ?
C1 C2 1.420(4) . ?
C2 C3 1.425(4) . ?
C2 C10 1.435(4) . ?
C3 C4 1.369(4) . ?
C3 H3 0.93(3) . ?
C4 C5 1.440(4) . ?
C5 C6 1.409(4) . ?
C5 C10 1.437(4) . ?
C6 C7 1.379(5) . ?
C6 H6 0.91(3) . ?
C7 C8 1.395(5) . ?
C7 H7 0.95(3) . ?
C8 C9 1.374(5) . ?
C8 H8 0.92(3) . ?
C9 C10 1.401(4) . ?
C9 H9 0.89(3) . ?
C11 H11C 0.97(3) . ?
C11 H11B 0.92(4) . ?
C11 H11A 0.98(3) . ?
C12 C13 1.501(6) . ?
C12 H12B 1.02(3) . ?
C12 H12A 0.96(4) . ?
C13 H13C 0.99(4) . ?
C13 H13B 1.02(4) . ?
C13 H13A 0.94(4) . ?
C14 C15 1.492(5) . ?
C14 H14B 0.98(4) . ?
C14 H14A 0.94(3) . ?
C15 H15C 0.90(4) . ?
C15 H15B 0.97(4) . ?
C15 H15A 1.02(4) . ?
C16 CL1 1.606(9) 3_666 ?
C16 CL1 1.819(8) . ?
C16 H16A 0.85(8) . ?
C16 H16B 0.83(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
C1 O2 H2 110(3) . . ?
C4 N1 C11 111.1(2) . . ?
C4 N1 C14 111.2(2) . . ?
C11 N1 C14 108.7(3) . . ?
C4 N1 C12 110.3(3) . . ?
C11 N1 C12 108.9(3) . . ?
C14 N1 C12 106.5(3) . . ?
O1 C1 O2 120.5(3) . . ?
O1 C1 C2 124.4(3) . . ?
O2 C1 C2 115.1(3) . . ?
C1 C2 C3 126.1(3) . . ?
C1 C2 C10 127.2(3) . . ?
C3 C2 C10 106.6(3) . . ?
C4 C3 C2 109.3(3) . . ?
C4 C3 H3 123.9(19) . . ?
C2 C3 H3 126.7(18) . . ?
C3 C4 C5 110.0(3) . . ?
C3 C4 N1 125.1(3) . . ?
C5 C4 N1 124.8(3) . . ?
C6 C5 C10 119.3(3) . . ?
C6 C5 C4 135.3(3) . . ?
C10 C5 C4 105.4(3) . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120(2) . . ?
C5 C6 H6 121(2) . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 117(2) . . ?
C8 C7 H7 122(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 120(2) . . ?
C7 C8 H8 119(2) . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 124(2) . . ?
C10 C9 H9 116(2) . . ?
C9 C10 C2 132.1(3) . . ?
C9 C10 C5 119.3(3) . . ?
C2 C10 C5 108.7(3) . . ?
N1 C11 H11C 110.5(19) . . ?
N1 C11 H11B 107(2) . . ?
H11C C11 H11B 113(3) . . ?
N1 C11 H11A 109.5(16) . . ?
H11C C11 H11A 110(2) . . ?
H11B C11 H11A 107(3) . . ?
C13 C12 N1 114.0(3) . . ?
C13 C12 H12B 114.0(18) . . ?
N1 C12 H12B 105.3(17) . . ?
C13 C12 H12A 111(2) . . ?
N1 C12 H12A 107(2) . . ?
H12B C12 H12A 105(3) . . ?
C12 C13 H13C 105(2) . . ?
C12 C13 H13B 108(2) . . ?
H13C C13 H13B 112(3) . . ?
C12 C13 H13A 116(2) . . ?
H13C C13 H13A 111(3) . . ?
H13B C13 H13A 104(3) . . ?
C15 C14 N1 114.2(3) . . ?
C15 C14 H14B 111(2) . . ?
N1 C14 H14B 104(2) . . ?
C15 C14 H14A 114(2) . . ?
N1 C14 H14A 106(2) . . ?
H14B C14 H14A 106(3) . . ?
C14 C15 H15C 113(2) . . ?
C14 C15 H15B 111(2) . . ?
H15C C15 H15B 110(3) . . ?
C14 C15 H15A 109(2) . . ?
H15C C15 H15A 106(3) . . ?
H15B C15 H15A 107(3) . . ?
CL1 C16 CL1 114.4(4) 3_666 . ?
CL1 C16 H16A 108(6) 3_666 . ?
CL1 C16 H16A 101(6) . . ?
CL1 C16 H16B 111(5) 3_666 . ?
CL1 C16 H16B 104(5) . . ?
H16A C16 H16B 118(7) . . ?


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
O1 C1 C2 C3 -175.5(3) . . . . ?
O2 C1 C2 C3 3.7(5) . . . . ?
O1 C1 C2 C10 0.4(5) . . . . ?
O2 C1 C2 C10 179.5(3) . . . . ?
C1 C2 C3 C4 175.9(3) . . . . ?
C10 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 N1 -177.5(3) . . . . ?
C11 N1 C4 C3 -1.6(4) . . . . ?
C14 N1 C4 C3 -122.8(3) . . . . ?
C12 N1 C4 C3 119.3(3) . . . . ?
C11 N1 C4 C5 -179.0(3) . . . . ?
C14 N1 C4 C5 59.8(4) . . . . ?
C12 N1 C4 C5 -58.1(4) . . . . ?
C3 C4 C5 C6 -179.5(4) . . . . ?
N1 C4 C5 C6 -1.8(6) . . . . ?
C3 C4 C5 C10 0.3(3) . . . . ?
N1 C4 C5 C10 178.0(3) . . . . ?
C10 C5 C6 C7 -0.3(5) . . . . ?
C4 C5 C6 C7 179.5(4) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C10 -0.6(6) . . . . ?
C8 C9 C10 C2 -178.6(3) . . . . ?
C8 C9 C10 C5 1.0(5) . . . . ?
C1 C2 C10 C9 4.0(6) . . . . ?
C3 C2 C10 C9 -179.5(3) . . . . ?
C1 C2 C10 C5 -175.7(3) . . . . ?
C3 C2 C10 C5 0.9(3) . . . . ?
C6 C5 C10 C9 -0.5(5) . . . . ?
C4 C5 C10 C9 179.6(3) . . . . ?
C6 C5 C10 C2 179.2(3) . . . . ?
C4 C5 C10 C2 -0.7(3) . . . . ?
C4 N1 C12 C13 -59.0(4) . . . . ?
C11 N1 C12 C13 63.1(4) . . . . ?
C14 N1 C12 C13 -179.8(4) . . . . ?
C4 N1 C14 C15 56.8(4) . . . . ?
C11 N1 C14 C15 -65.7(4) . . . . ?
C12 N1 C14 C15 177.0(3) . . . . ?
CL1 C16 CL1 C16 0.003(1) 3_666 . . 3_666 ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.066

