# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sl_k3_0002
_database_code_depnum_ccdc_archive 'CCDC 1483699'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-07-26 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Shing Lau'
_cambridge_user_crsid            shl56
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             DNT-182
_cambridge_data_id               SL_K3_0002

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 Cl N O2'
_chemical_formula_sum            'C18 H22 Cl N O2'
_chemical_formula_weight         319.81

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.46790(10)
_cell_length_b                   11.3192(2)
_cell_length_c                   16.4547(3)
_cell_angle_alpha                90.2760(10)
_cell_angle_beta                 105.5300(10)
_cell_angle_gamma                90.5090(10)
_cell_volume                     1698.94(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    26068
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  1.061
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36046
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.600
_diffrn_reflns_theta_max         27.443
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             7442
_reflns_number_gt                6165
_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       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0388P)²+0.6583P] 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         7442
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.042

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_1 Cl 0.42796(4) 0.17763(3) 0.82154(2) 0.03648(10) Uani 1 1 d . . . . .
O1_1 O 0.08611(11) 0.44390(9) 0.71454(6) 0.0297(2) Uani 1 1 d . . . . .
H1_1 H 0.143(2) 0.4940(18) 0.7060(12) 0.053(6) Uiso 1 1 d . . . . .
O2_1 O 0.01941(13) 0.05583(10) 0.33767(6) 0.0424(3) Uani 1 1 d . . . . .
N1_1 N 0.35041(13) 0.10004(10) 0.66804(7) 0.0286(3) Uani 1 1 d . . . . .
C1_1 C 0.31386(15) 0.17620(12) 0.71857(8) 0.0267(3) Uani 1 1 d . . . . .
C2_1 C 0.19634(14) 0.25652(12) 0.69679(8) 0.0250(3) Uani 1 1 d . . . . .
C3_1 C 0.10924(15) 0.24789(12) 0.61543(9) 0.0263(3) Uani 1 1 d . . . . .
H3A_1 H 0.0262 0.2973 0.5979 0.032 Uiso 1 1 calc R U . . .
C4_1 C 0.14095(15) 0.16672(12) 0.55723(8) 0.0260(3) Uani 1 1 d . . . . .
C5_1 C 0.05486(16) 0.15623(13) 0.47241(9) 0.0300(3) Uani 1 1 d . . . . .
H5A_1 H -0.0293 0.2039 0.4525 0.036 Uiso 1 1 calc R U . . .
C6_1 C 0.09422(17) 0.07667(13) 0.41949(9) 0.0330(3) Uani 1 1 d . . . . .
C7_1 C 0.22072(18) 0.00667(14) 0.44807(10) 0.0377(4) Uani 1 1 d . . . . .
H7A_1 H 0.2474 -0.0469 0.4103 0.045 Uiso 1 1 calc R U . . .
C8_1 C 0.30445(17) 0.01543(13) 0.52920(9) 0.0351(3) Uani 1 1 d . . . . .
H8A_1 H 0.3891 -0.0321 0.5477 0.042 Uiso 1 1 calc R U . . .
C9_1 C 0.26584(15) 0.09500(12) 0.58596(9) 0.0277(3) Uani 1 1 d . . . . .
C10_1 C -0.10457(18) 0.12708(16) 0.30249(10) 0.0430(4) Uani 1 1 d . . . . .
H10A_1 H -0.1469 0.1046 0.2433 0.065 Uiso 1 1 calc R U . . .
H10B_1 H -0.0743 0.2104 0.3059 0.065 Uiso 1 1 calc R U . . .
H10C_1 H -0.1779 0.1154 0.3340 0.065 Uiso 1 1 calc R U . . .
C11_1 C 0.17020(15) 0.34870(12) 0.75832(8) 0.0255(3) Uani 1 1 d . . . . .
H11A_1 H 0.2673 0.3806 0.7919 0.031 Uiso 1 1 calc R U . . .
C12_1 C 0.08864(15) 0.29667(12) 0.81969(9) 0.0275(3) Uani 1 1 d . . . . .
H12A_1 H 0.1425 0.2252 0.8465 0.033 Uiso 1 1 calc R U . . .
C13_1 C -0.06533(17) 0.25954(14) 0.77375(10) 0.0356(3) Uani 1 1 d . . . . .
H13A_1 H -0.1292 0.3184 0.7439 0.043 Uiso 1 1 calc R U . . .
C14_1 C -0.1170(2) 0.15182(17) 0.77209(11) 0.0495(4) Uani 1 1 d . . . . .
H14A_1 H -0.0561 0.0907 0.8012 0.059 Uiso 1 1 calc R U . . .
H14B_1 H -0.2155 0.1346 0.7418 0.059 Uiso 1 1 calc R U . . .
C15_1 C 0.08338(16) 0.38508(13) 0.88963(9) 0.0308(3) Uani 1 1 d . . . . .
H15A_1 H 0.0307 0.4561 0.8630 0.037 Uiso 1 1 calc R U . . .
H15B_1 H 0.0248 0.3493 0.9250 0.037 Uiso 1 1 calc R U . . .
C16_1 C 0.23046(16) 0.42459(13) 0.94721(9) 0.0304(3) Uani 1 1 d . . . . .
H16A_1 H 0.2829 0.3550 0.9763 0.036 Uiso 1 1 calc R U . . .
H16B_1 H 0.2909 0.4601 0.9129 0.036 Uiso 1 1 calc R U . . .
C17_1 C 0.21132(18) 0.51399(15) 1.01230(10) 0.0387(4) Uani 1 1 d . . . . .
H17A_1 H 0.1532 0.4770 1.0474 0.046 Uiso 1 1 calc R U . . .
H17B_1 H 0.1547 0.5815 0.9827 0.046 Uiso 1 1 calc R U . . .
C18_1 C 0.3548(2) 0.56026(17) 1.06975(11) 0.0488(4) Uani 1 1 d . . . . .
H18A_1 H 0.3343 0.6185 1.1092 0.073 Uiso 1 1 calc R U . . .
H18B_1 H 0.4130 0.5976 1.0357 0.073 Uiso 1 1 calc R U . . .
H18C_1 H 0.4097 0.4945 1.1014 0.073 Uiso 1 1 calc R U . . .
Cl1_2 Cl 0.34465(4) 0.68609(4) 0.82978(2) 0.03872(10) Uani 1 1 d . . . . .
O1_2 O 0.60522(12) 0.95194(9) 0.73195(7) 0.0315(2) Uani 1 1 d . . . . .
H1_2 H 0.534(2) 0.9953(18) 0.7146(13) 0.055(6) Uiso 1 1 d . . . . .
O2_2 O 0.35157(13) 0.56465(11) 0.35284(7) 0.0435(3) Uani 1 1 d . . . . .
N1_2 N 0.29073(13) 0.60959(10) 0.67589(8) 0.0311(3) Uani 1 1 d . . . . .
C1_2 C 0.37278(15) 0.68480(12) 0.72890(9) 0.0294(3) Uani 1 1 d . . . . .
C2_2 C 0.47672(15) 0.76417(12) 0.71115(9) 0.0270(3) Uani 1 1 d . . . . .
C3_2 C 0.49645(15) 0.75553(12) 0.63187(9) 0.0280(3) Uani 1 1 d . . . . .
H3A_2 H 0.5680 0.8043 0.6173 0.034 Uiso 1 1 calc R U . . .
C4_2 C 0.41281(15) 0.67571(12) 0.57129(9) 0.0277(3) Uani 1 1 d . . . . .
C5_2 C 0.42944(16) 0.66513(13) 0.48842(9) 0.0320(3) Uani 1 1 d . . . . .
H5A_2 H 0.4999 0.7124 0.4715 0.038 Uiso 1 1 calc R U . . .
C6_2 C 0.34307(17) 0.58618(14) 0.43286(9) 0.0340(3) Uani 1 1 d . . . . .
C7_2 C 0.23515(18) 0.51768(14) 0.45686(10) 0.0391(4) Uani 1 1 d . . . . .
H7A_2 H 0.1743 0.4649 0.4172 0.047 Uiso 1 1 calc R U . . .
C8_2 C 0.21774(17) 0.52663(14) 0.53599(10) 0.0369(3) Uani 1 1 d . . . . .
H8A_2 H 0.1451 0.4801 0.5513 0.044 Uiso 1 1 calc R U . . .
C9_2 C 0.30734(15) 0.60497(12) 0.59571(9) 0.0298(3) Uani 1 1 d . . . . .
C10_2 C 0.4524(2) 0.63508(17) 0.32300(11) 0.0470(4) Uani 1 1 d . . . . .
H10A_2 H 0.4496 0.6108 0.2653 0.071 Uiso 1 1 calc R U . . .
H10B_2 H 0.5516 0.6245 0.3597 0.071 Uiso 1 1 calc R U . . .
H10C_2 H 0.4254 0.7184 0.3234 0.071 Uiso 1 1 calc R U . . .
C11_2 C 0.55958(15) 0.85575(12) 0.77442(9) 0.0278(3) Uani 1 1 d . . . . .
H11A_2 H 0.4928 0.8862 0.8074 0.033 Uiso 1 1 calc R U . . .
C12_2 C 0.69679(15) 0.80365(13) 0.83632(9) 0.0307(3) Uani 1 1 d . . . . .
H12A_2 H 0.6655 0.7325 0.8631 0.037 Uiso 1 1 calc R U . . .
C13_2 C 0.80571(17) 0.76491(14) 0.78989(10) 0.0372(3) Uani 1 1 d . . . . .
H13A_2 H 0.8548 0.8248 0.7674 0.045 Uiso 1 1 calc R U . . .
C14_2 C 0.8381(2) 0.65465(17) 0.77811(12) 0.0512(4) Uani 1 1 d . . . . .
H14A_2 H 0.7913 0.5922 0.7997 0.061 Uiso 1 1 calc R U . . .
H14B_2 H 0.9082 0.6373 0.7480 0.061 Uiso 1 1 calc R U . . .
C15_2 C 0.76927(17) 0.89226(14) 0.90677(10) 0.0371(3) Uani 1 1 d . . . . .
H15A_2 H 0.8620 0.8578 0.9407 0.045 Uiso 1 1 calc R U . . .
H15B_2 H 0.7950 0.9647 0.8802 0.045 Uiso 1 1 calc R U . . .
C16_2 C 0.67825(18) 0.92771(15) 0.96636(10) 0.0394(4) Uani 1 1 d . . . . .
H16A_2 H 0.6477 0.8555 0.9912 0.047 Uiso 1 1 calc R U . . .
H16B_2 H 0.5885 0.9676 0.9336 0.047 Uiso 1 1 calc R U . . .
C17_2 C 0.7609(2) 1.01012(16) 1.03772(10) 0.0462(4) Uani 1 1 d . . . . .
H17A_2 H 0.7055 1.0146 1.0808 0.055 Uiso 1 1 calc R U . . .
H17B_2 H 0.8576 0.9755 1.0647 0.055 Uiso 1 1 calc R U . . .
C18_2 C 0.7841(2) 1.13281(17) 1.00979(13) 0.0590(5) Uani 1 1 d . . . . .
H18A_2 H 0.8419 1.1789 1.0580 0.089 Uiso 1 1 calc R U . . .
H18B_2 H 0.6889 1.1704 0.9871 0.089 Uiso 1 1 calc R U . . .
H18C_2 H 0.8366 1.1294 0.9660 0.089 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
Cl1_1 C1_1 1.7486(14) . ?
O1_1 C11_1 1.4246(16) . ?
O1_1 H1_1 0.82(2) . ?
O2_1 C6_1 1.3613(17) . ?
O2_1 C10_1 1.4215(19) . ?
N1_1 C1_1 1.3064(18) . ?
N1_1 C9_1 1.3741(18) . ?
C1_1 C2_1 1.4144(19) . ?
C2_1 C3_1 1.3740(19) . ?
C2_1 C11_1 1.5177(18) . ?
C3_1 C4_1 1.4149(19) . ?
C3_1 H3A_1 0.9500 . ?
C4_1 C9_1 1.4149(19) . ?
C4_1 C5_1 1.4191(19) . ?
C5_1 C6_1 1.371(2) . ?
C5_1 H5A_1 0.9500 . ?
C6_1 C7_1 1.415(2) . ?
C7_1 C8_1 1.360(2) . ?
C7_1 H7A_1 0.9500 . ?
C8_1 C9_1 1.4135(19) . ?
C8_1 H8A_1 0.9500 . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C11_1 C12_1 1.5422(18) . ?
C11_1 H11A_1 1.0000 . ?
C12_1 C13_1 1.506(2) . ?
C12_1 C15_1 1.5326(19) . ?
C12_1 H12A_1 1.0000 . ?
C13_1 C14_1 1.307(2) . ?
C13_1 H13A_1 0.9500 . ?
C14_1 H14A_1 0.9500 . ?
C14_1 H14B_1 0.9500 . ?
C15_1 C16_1 1.522(2) . ?
C15_1 H15A_1 0.9900 . ?
C15_1 H15B_1 0.9900 . ?
C16_1 C17_1 1.517(2) . ?
C16_1 H16A_1 0.9900 . ?
C16_1 H16B_1 0.9900 . ?
C17_1 C18_1 1.519(2) . ?
C17_1 H17A_1 0.9900 . ?
C17_1 H17B_1 0.9900 . ?
C18_1 H18A_1 0.9800 . ?
C18_1 H18B_1 0.9800 . ?
C18_1 H18C_1 0.9800 . ?
Cl1_2 C1_2 1.7503(15) . ?
O1_2 C11_2 1.4217(16) . ?
O1_2 H1_2 0.83(2) . ?
O2_2 C6_2 1.3615(18) . ?
O2_2 C10_2 1.425(2) . ?
N1_2 C1_2 1.3066(19) . ?
N1_2 C9_2 1.3706(19) . ?
C1_2 C2_2 1.4148(19) . ?
C2_2 C3_2 1.370(2) . ?
C2_2 C11_2 1.5204(19) . ?
C3_2 C4_2 1.412(2) . ?
C3_2 H3A_2 0.9500 . ?
C4_2 C9_2 1.4155(19) . ?
C4_2 C5_2 1.419(2) . ?
C5_2 C6_2 1.372(2) . ?
C5_2 H5A_2 0.9500 . ?
C6_2 C7_2 1.416(2) . ?
C7_2 C8_2 1.359(2) . ?
C7_2 H7A_2 0.9500 . ?
C8_2 C9_2 1.415(2) . ?
C8_2 H8A_2 0.9500 . ?
C10_2 H10A_2 0.9800 . ?
C10_2 H10B_2 0.9800 . ?
C10_2 H10C_2 0.9800 . ?
C11_2 C12_2 1.5440(19) . ?
C11_2 H11A_2 1.0000 . ?
C12_2 C13_2 1.505(2) . ?
C12_2 C15_2 1.540(2) . ?
C12_2 H12A_2 1.0000 . ?
C13_2 C14_2 1.313(2) . ?
C13_2 H13A_2 0.9500 . ?
C14_2 H14A_2 0.9500 . ?
C14_2 H14B_2 0.9500 . ?
C15_2 C16_2 1.523(2) . ?
C15_2 H15A_2 0.9900 . ?
C15_2 H15B_2 0.9900 . ?
C16_2 C17_2 1.532(2) . ?
C16_2 H16A_2 0.9900 . ?
C16_2 H16B_2 0.9900 . ?
C17_2 C18_2 1.498(3) . ?
C17_2 H17A_2 0.9900 . ?
C17_2 H17B_2 0.9900 . ?
C18_2 H18A_2 0.9800 . ?
C18_2 H18B_2 0.9800 . ?
C18_2 H18C_2 0.9800 . ?

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
C11_1 O1_1 H1_1 108.0(14) . . ?
C6_1 O2_1 C10_1 117.54(12) . . ?
C1_1 N1_1 C9_1 117.54(12) . . ?
N1_1 C1_1 C2_1 126.32(13) . . ?
N1_1 C1_1 Cl1_1 114.57(10) . . ?
C2_1 C1_1 Cl1_1 119.08(10) . . ?
C3_1 C2_1 C1_1 115.67(12) . . ?
C3_1 C2_1 C11_1 121.96(12) . . ?
C1_1 C2_1 C11_1 122.35(12) . . ?
C2_1 C3_1 C4_1 121.22(13) . . ?
C2_1 C3_1 H3A_1 119.4 . . ?
C4_1 C3_1 H3A_1 119.4 . . ?
C9_1 C4_1 C3_1 117.47(12) . . ?
C9_1 C4_1 C5_1 119.61(12) . . ?
C3_1 C4_1 C5_1 122.92(13) . . ?
C6_1 C5_1 C4_1 119.39(13) . . ?
C6_1 C5_1 H5A_1 120.3 . . ?
C4_1 C5_1 H5A_1 120.3 . . ?
O2_1 C6_1 C5_1 125.28(14) . . ?
O2_1 C6_1 C7_1 113.91(13) . . ?
C5_1 C6_1 C7_1 120.80(13) . . ?
C8_1 C7_1 C6_1 120.61(14) . . ?
C8_1 C7_1 H7A_1 119.7 . . ?
C6_1 C7_1 H7A_1 119.7 . . ?
C7_1 C8_1 C9_1 120.17(14) . . ?
C7_1 C8_1 H8A_1 119.9 . . ?
C9_1 C8_1 H8A_1 119.9 . . ?
N1_1 C9_1 C8_1 118.94(13) . . ?
N1_1 C9_1 C4_1 121.66(12) . . ?
C8_1 C9_1 C4_1 119.40(13) . . ?
O2_1 C10_1 H10A_1 109.5 . . ?
O2_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
O2_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
O1_1 C11_1 C2_1 110.81(11) . . ?
O1_1 C11_1 C12_1 108.17(11) . . ?
C2_1 C11_1 C12_1 112.05(11) . . ?
O1_1 C11_1 H11A_1 108.6 . . ?
C2_1 C11_1 H11A_1 108.6 . . ?
C12_1 C11_1 H11A_1 108.6 . . ?
C13_1 C12_1 C15_1 109.23(11) . . ?
C13_1 C12_1 C11_1 111.12(11) . . ?
C15_1 C12_1 C11_1 111.54(11) . . ?
C13_1 C12_1 H12A_1 108.3 . . ?
C15_1 C12_1 H12A_1 108.3 . . ?
C11_1 C12_1 H12A_1 108.3 . . ?
C14_1 C13_1 C12_1 124.48(16) . . ?
C14_1 C13_1 H13A_1 117.8 . . ?
C12_1 C13_1 H13A_1 117.8 . . ?
C13_1 C14_1 H14A_1 120.0 . . ?
C13_1 C14_1 H14B_1 120.0 . . ?
H14A_1 C14_1 H14B_1 120.0 . . ?
C16_1 C15_1 C12_1 116.29(12) . . ?
C16_1 C15_1 H15A_1 108.2 . . ?
C12_1 C15_1 H15A_1 108.2 . . ?
C16_1 C15_1 H15B_1 108.2 . . ?
C12_1 C15_1 H15B_1 108.2 . . ?
H15A_1 C15_1 H15B_1 107.4 . . ?
C17_1 C16_1 C15_1 111.42(12) . . ?
C17_1 C16_1 H16A_1 109.3 . . ?
C15_1 C16_1 H16A_1 109.3 . . ?
C17_1 C16_1 H16B_1 109.3 . . ?
C15_1 C16_1 H16B_1 109.3 . . ?
H16A_1 C16_1 H16B_1 108.0 . . ?
C16_1 C17_1 C18_1 113.90(14) . . ?
C16_1 C17_1 H17A_1 108.8 . . ?
C18_1 C17_1 H17A_1 108.8 . . ?
C16_1 C17_1 H17B_1 108.8 . . ?
C18_1 C17_1 H17B_1 108.8 . . ?
H17A_1 C17_1 H17B_1 107.7 . . ?
C17_1 C18_1 H18A_1 109.5 . . ?
C17_1 C18_1 H18B_1 109.5 . . ?
H18A_1 C18_1 H18B_1 109.5 . . ?
C17_1 C18_1 H18C_1 109.5 . . ?
H18A_1 C18_1 H18C_1 109.5 . . ?
H18B_1 C18_1 H18C_1 109.5 . . ?
C11_2 O1_2 H1_2 107.7(14) . . ?
C6_2 O2_2 C10_2 117.06(12) . . ?
C1_2 N1_2 C9_2 117.63(12) . . ?
N1_2 C1_2 C2_2 126.11(13) . . ?
N1_2 C1_2 Cl1_2 114.97(10) . . ?
C2_2 C1_2 Cl1_2 118.91(11) . . ?
C3_2 C2_2 C1_2 115.69(13) . . ?
C3_2 C2_2 C11_2 121.40(12) . . ?
C1_2 C2_2 C11_2 122.89(13) . . ?
C2_2 C3_2 C4_2 121.45(13) . . ?
C2_2 C3_2 H3A_2 119.3 . . ?
C4_2 C3_2 H3A_2 119.3 . . ?
C3_2 C4_2 C9_2 117.30(13) . . ?
C3_2 C4_2 C5_2 122.97(13) . . ?
C9_2 C4_2 C5_2 119.73(13) . . ?
C6_2 C5_2 C4_2 119.53(13) . . ?
C6_2 C5_2 H5A_2 120.2 . . ?
C4_2 C5_2 H5A_2 120.2 . . ?
O2_2 C6_2 C5_2 125.30(14) . . ?
O2_2 C6_2 C7_2 114.13(13) . . ?
C5_2 C6_2 C7_2 120.57(14) . . ?
C8_2 C7_2 C6_2 120.69(14) . . ?
C8_2 C7_2 H7A_2 119.7 . . ?
C6_2 C7_2 H7A_2 119.7 . . ?
C7_2 C8_2 C9_2 120.34(14) . . ?
C7_2 C8_2 H8A_2 119.8 . . ?
C9_2 C8_2 H8A_2 119.8 . . ?
N1_2 C9_2 C8_2 119.19(13) . . ?
N1_2 C9_2 C4_2 121.69(13) . . ?
C8_2 C9_2 C4_2 119.11(13) . . ?
O2_2 C10_2 H10A_2 109.5 . . ?
O2_2 C10_2 H10B_2 109.5 . . ?
H10A_2 C10_2 H10B_2 109.5 . . ?
O2_2 C10_2 H10C_2 109.5 . . ?
H10A_2 C10_2 H10C_2 109.5 . . ?
H10B_2 C10_2 H10C_2 109.5 . . ?
O1_2 C11_2 C2_2 110.39(11) . . ?
O1_2 C11_2 C12_2 108.19(11) . . ?
C2_2 C11_2 C12_2 112.07(11) . . ?
O1_2 C11_2 H11A_2 108.7 . . ?
C2_2 C11_2 H11A_2 108.7 . . ?
C12_2 C11_2 H11A_2 108.7 . . ?
C13_2 C12_2 C15_2 110.13(12) . . ?
C13_2 C12_2 C11_2 110.52(12) . . ?
C15_2 C12_2 C11_2 111.74(12) . . ?
C13_2 C12_2 H12A_2 108.1 . . ?
C15_2 C12_2 H12A_2 108.1 . . ?
C11_2 C12_2 H12A_2 108.1 . . ?
C14_2 C13_2 C12_2 125.03(16) . . ?
C14_2 C13_2 H13A_2 117.5 . . ?
C12_2 C13_2 H13A_2 117.5 . . ?
C13_2 C14_2 H14A_2 120.0 . . ?
C13_2 C14_2 H14B_2 120.0 . . ?
H14A_2 C14_2 H14B_2 120.0 . . ?
C16_2 C15_2 C12_2 116.14(13) . . ?
C16_2 C15_2 H15A_2 108.3 . . ?
C12_2 C15_2 H15A_2 108.3 . . ?
C16_2 C15_2 H15B_2 108.3 . . ?
C12_2 C15_2 H15B_2 108.3 . . ?
H15A_2 C15_2 H15B_2 107.4 . . ?
C15_2 C16_2 C17_2 113.09(14) . . ?
C15_2 C16_2 H16A_2 109.0 . . ?
C17_2 C16_2 H16A_2 109.0 . . ?
C15_2 C16_2 H16B_2 109.0 . . ?
C17_2 C16_2 H16B_2 109.0 . . ?
H16A_2 C16_2 H16B_2 107.8 . . ?
C18_2 C17_2 C16_2 114.13(14) . . ?
C18_2 C17_2 H17A_2 108.7 . . ?
C16_2 C17_2 H17A_2 108.7 . . ?
C18_2 C17_2 H17B_2 108.7 . . ?
C16_2 C17_2 H17B_2 108.7 . . ?
H17A_2 C17_2 H17B_2 107.6 . . ?
C17_2 C18_2 H18A_2 109.5 . . ?
C17_2 C18_2 H18B_2 109.5 . . ?
H18A_2 C18_2 H18B_2 109.5 . . ?
C17_2 C18_2 H18C_2 109.5 . . ?
H18A_2 C18_2 H18C_2 109.5 . . ?
H18B_2 C18_2 H18C_2 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1_1 H1_1 N1_2 0.82(2) 2.06(2) 2.8778(16) 174.5(19) .
O1_2 H1_2 N1_1 0.83(2) 2.08(2) 2.9097(16) 178(2) 1_565

