# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 
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data_cd1352a
_database_code_depnum_ccdc_archive 'CCDC 1417169'
_audit_update_record             
;
2015-08-06 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 Cl O5'
_chemical_formula_sum            'C17 H19 Cl O5'
_chemical_formula_weight         338.77
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.410(6)
_cell_length_b                   9.115(3)
_cell_length_c                   8.678(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.827(4)
_cell_angle_gamma                90
_cell_volume                     1693.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      1.9
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.30
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5190
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         2.347
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 35.0218
	          2theta: -35.0123
scan:
	Number of images: 202
	           Slice: -67.0000 - 34.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 35.0218
	          2theta: -35.0123
scan:
	Number of images: 134
	           Slice: -87.0000 - -20.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0218
	          2theta: -35.0123
scan:
	Number of images: 60
	           Slice: -61.0000 - -31.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 35.0218
	          2theta: -35.0123
scan:
	Number of images: 60
	           Slice: -115.0000 - -85.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 35.0218
	          2theta: -35.0123
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.015950
_diffrn_orient_matrix_UB_12      0.028085
_diffrn_orient_matrix_UB_13      -0.033746
_diffrn_orient_matrix_UB_21      0.102912
_diffrn_orient_matrix_UB_22      0.029157
_diffrn_orient_matrix_UB_23      -0.024375
_diffrn_orient_matrix_UB_31      0.006164
_diffrn_orient_matrix_UB_32      -0.085837
_diffrn_orient_matrix_UB_33      -0.076653
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_full    0.610
_reflns_Friedel_fraction_max     0.610
_reflns_number_gt                2350
_reflns_number_total             2420
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.1160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C17(H17A,H17B), C14(H14A,H14B), C16(H16A,H16B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 Cl 0.42324(3) 0.05813(9) 0.09521(9) 0.0711(3) Uani 1 1 d . . . . .
O1 O 0.42376(7) 0.3671(2) 0.8030(2) 0.0529(4) Uani 1 1 d . . . . .
H1 H 0.4065 0.3038 0.8544 0.079 Uiso 1 1 calc GR . . . .
O4 O 0.37549(10) 0.6944(2) 0.6197(2) 0.0677(5) Uani 1 1 d . . . . .
O5 O 0.31520(10) 0.2913(2) 0.9565(3) 0.0664(5) Uani 1 1 d . . . . .
O2 O 0.27770(8) 0.4233(3) 0.6472(2) 0.0665(6) Uani 1 1 d . . . . .
O3 O 0.47122(10) 0.6094(3) 0.6818(3) 0.0734(6) Uani 1 1 d . . . . .
C7 C 0.33858(11) 0.1333(3) 0.3087(3) 0.0497(6) Uani 1 1 d . . . . .
H7 H 0.3123 0.0651 0.2615 0.060 Uiso 1 1 calc R . . . .
C1 C 0.37955(10) 0.4726(3) 0.7556(3) 0.0444(5) Uani 1 1 d . . . . .
C9 C 0.41594(13) 0.5990(3) 0.6809(3) 0.0533(6) Uani 1 1 d . . . . .
C8 C 0.31867(10) 0.2139(3) 0.4341(3) 0.0469(5) Uani 1 1 d . . . . .
H8 H 0.2783 0.2010 0.4699 0.056 Uiso 1 1 calc R . . . .
C3 C 0.35824(10) 0.3137(3) 0.5074(3) 0.0429(5) Uani 1 1 d . . . . .
C2 C 0.33312(10) 0.4048(3) 0.6358(3) 0.0451(5) Uani 1 1 d . . . . .
C6 C 0.39824(10) 0.1561(3) 0.2548(3) 0.0489(6) Uani 1 1 d . . . . .
C4 C 0.41839(10) 0.3318(3) 0.4518(3) 0.0531(6) Uani 1 1 d . . . . .
H4 H 0.4457 0.3962 0.5014 0.064 Uiso 1 1 calc R . . . .
C12 C 0.34332(11) 0.5376(3) 0.8922(3) 0.0464(5) Uani 1 1 d . . . . .
H12 H 0.3126 0.6071 0.8500 0.056 Uiso 1 1 calc R . . . .
C5 C 0.43814(11) 0.2554(3) 0.3242(3) 0.0556(6) Uani 1 1 d . . . . .
H5 H 0.4779 0.2708 0.2855 0.067 Uiso 1 1 calc R . . . .
C13 C 0.30791(12) 0.4212(3) 0.9797(3) 0.0528(6) Uani 1 1 d . . . . .
C18 C 0.38470(14) 0.6213(4) 1.0084(3) 0.0622(7) Uani 1 1 d . . . . .
H18A H 0.4152 0.5548 1.0537 0.075 Uiso 1 1 calc R . . . .
H18B H 0.4071 0.6985 0.9556 0.075 Uiso 1 1 calc R . . . .
C17 C 0.34524(18) 0.6881(4) 1.1351(3) 0.0730(9) Uani 1 1 d . . . . .
H17A H 0.3724 0.7363 1.2099 0.088 Uiso 1 1 calc R . . . .
H17B H 0.3177 0.7617 1.0907 0.088 Uiso 1 1 calc R . . . .
C14 C 0.26718(16) 0.4798(4) 1.1045(4) 0.0703(8) Uani 1 1 d . . . . .
H14A H 0.2483 0.3991 1.1598 0.084 Uiso 1 1 calc R . . . .
H14B H 0.2340 0.5392 1.0596 0.084 Uiso 1 1 calc R . . . .
C16 C 0.3067(2) 0.5729(5) 1.2158(3) 0.0829(10) Uani 1 1 d . . . . .
H16A H 0.2792 0.6210 1.2881 0.100 Uiso 1 1 calc R . . . .
H16B H 0.3344 0.5089 1.2742 0.100 Uiso 1 1 calc R . . . .
C10 C 0.4015(2) 0.8253(4) 0.5482(4) 0.0882(11) Uani 1 1 d . . . . .
H10A H 0.3717 0.8643 0.4737 0.106 Uiso 1 1 calc R . . . .
H10B H 0.4391 0.7992 0.4937 0.106 Uiso 1 1 calc R . . . .
C11 C 0.4166(3) 0.9400(5) 0.6653(5) 0.1063(15) Uani 1 1 d . . . . .
H11A H 0.4301 1.0277 0.6142 0.159 Uiso 1 1 calc GR . . . .
H11B H 0.4494 0.9054 0.7325 0.159 Uiso 1 1 calc GR . . . .
H11C H 0.3801 0.9609 0.7244 0.159 Uiso 1 1 calc GR . . . .


_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 C6 1.739(2) . ?
O1 H1 0.8200 . ?
O1 C1 1.407(3) . ?
O4 C9 1.332(4) . ?
O4 C10 1.459(4) . ?
O5 C13 1.212(4) . ?
O2 C2 1.204(3) . ?
O3 C9 1.187(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(4) . ?
C7 C6 1.382(3) . ?
C1 C9 1.539(4) . ?
C1 C2 1.556(3) . ?
C1 C12 1.544(3) . ?
C8 H8 0.9300 . ?
C8 C3 1.391(3) . ?
C3 C2 1.496(3) . ?
C3 C4 1.391(3) . ?
C6 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.514(4) . ?
C12 C18 1.536(4) . ?
C5 H5 0.9300 . ?
C13 C14 1.499(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.523(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.514(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C16 1.531(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.490(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C1 O1 H1 109.5 . . ?
C9 O4 C10 116.9(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(2) . . ?
O1 C1 C9 107.01(19) . . ?
O1 C1 C2 110.13(19) . . ?
O1 C1 C12 112.39(19) . . ?
C9 C1 C2 109.79(19) . . ?
C9 C1 C12 107.4(2) . . ?
C12 C1 C2 110.01(18) . . ?
O4 C9 C1 109.0(2) . . ?
O3 C9 O4 126.4(3) . . ?
O3 C9 C1 124.6(3) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C3 120.91(19) . . ?
C3 C8 H8 119.5 . . ?
C8 C3 C2 118.72(18) . . ?
C8 C3 C4 118.7(2) . . ?
C4 C3 C2 122.5(2) . . ?
O2 C2 C1 120.7(2) . . ?
O2 C2 C3 120.3(2) . . ?
C3 C2 C1 119.02(18) . . ?
C7 C6 Cl1 119.2(2) . . ?
C5 C6 Cl1 119.32(18) . . ?
C5 C6 C7 121.4(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C1 C12 H12 107.6 . . ?
C13 C12 C1 112.1(2) . . ?
C13 C12 H12 107.6 . . ?
C13 C12 C18 107.9(2) . . ?
C18 C12 C1 113.8(2) . . ?
C18 C12 H12 107.6 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
O5 C13 C12 122.4(2) . . ?
O5 C13 C14 123.1(3) . . ?
C14 C13 C12 114.4(2) . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C17 C18 C12 110.6(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C16 C17 C18 111.6(3) . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C13 C14 C16 109.4(3) . . ?
H14A C14 H14B 108.2 . . ?
C16 C14 H14A 109.8 . . ?
C16 C14 H14B 109.8 . . ?
C17 C16 C14 113.1(2) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C14 C16 H16A 109.0 . . ?
C14 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O4 C10 H10A 109.4 . . ?
O4 C10 H10B 109.4 . . ?
O4 C10 C11 111.4(3) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Cl1 C6 C5 C4 -179.3(2) . . . . ?
O1 C1 C9 O4 173.48(19) . . . . ?
O1 C1 C9 O3 -7.9(4) . . . . ?
O1 C1 C2 O2 133.5(3) . . . . ?
O1 C1 C2 C3 -45.4(3) . . . . ?
O1 C1 C12 C13 -59.9(3) . . . . ?
O1 C1 C12 C18 62.9(3) . . . . ?
O5 C13 C14 C16 119.9(3) . . . . ?
C7 C8 C3 C2 176.1(2) . . . . ?
C7 C8 C3 C4 0.2(4) . . . . ?
C7 C6 C5 C4 1.1(4) . . . . ?
C1 C12 C13 O5 9.8(4) . . . . ?
C1 C12 C13 C14 -174.6(2) . . . . ?
C1 C12 C18 C17 177.3(2) . . . . ?
C9 O4 C10 C11 -82.2(4) . . . . ?
C9 C1 C2 O2 -109.0(3) . . . . ?
C9 C1 C2 C3 72.2(3) . . . . ?
C9 C1 C12 C13 -177.32(19) . . . . ?
C9 C1 C12 C18 -54.5(3) . . . . ?
C8 C7 C6 Cl1 -178.81(19) . . . . ?
C8 C7 C6 C5 0.8(4) . . . . ?
C8 C3 C2 O2 -20.8(3) . . . . ?
C8 C3 C2 C1 158.0(2) . . . . ?
C8 C3 C4 C5 1.7(4) . . . . ?
C3 C4 C5 C6 -2.4(4) . . . . ?
C2 C1 C9 O4 54.0(3) . . . . ?
C2 C1 C9 O3 -127.4(3) . . . . ?
C2 C1 C12 C13 63.2(2) . . . . ?
C2 C1 C12 C18 -174.0(2) . . . . ?
C2 C3 C4 C5 -174.0(2) . . . . ?
C6 C7 C8 C3 -1.5(4) . . . . ?
C4 C3 C2 O2 154.9(3) . . . . ?
C4 C3 C2 C1 -26.3(3) . . . . ?
C12 C1 C9 O4 -65.6(2) . . . . ?
C12 C1 C9 O3 113.0(3) . . . . ?
C12 C1 C2 O2 9.0(3) . . . . ?
C12 C1 C2 C3 -169.82(19) . . . . ?
C12 C13 C14 C16 -55.6(3) . . . . ?
C12 C18 C17 C16 56.2(4) . . . . ?
C13 C12 C18 C17 -57.6(3) . . . . ?
C13 C14 C16 C17 51.1(4) . . . . ?
C18 C12 C13 O5 -116.2(3) . . . . ?
C18 C12 C13 C14 59.3(3) . . . . ?
C18 C17 C16 C14 -53.0(4) . . . . ?
C10 O4 C9 O3 -0.8(4) . . . . ?
C10 O4 C9 C1 177.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cd1350
_database_code_depnum_ccdc_archive 'CCDC 1417170'
_audit_update_record             
;
2015-08-06 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_date             2015-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 Cl N O3'
_chemical_formula_sum            'C23 H22 Cl N O3'
_chemical_formula_weight         395.86
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.258(2)
_cell_length_b                   9.554(2)
_cell_length_c                   22.789(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2015.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8517
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7560
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         2.312
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
scan:
	Number of images: 270
	           Slice: -125.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 35.0267
	          2theta: -34.8839
scan:
	Number of images: 126
	           Slice: -68.0000 - -5.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 35.0267
	          2theta: -34.8839
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.002650
_diffrn_orient_matrix_UB_12      -0.024454
_diffrn_orient_matrix_UB_13      -0.105177
_diffrn_orient_matrix_UB_21      -0.026935
_diffrn_orient_matrix_UB_22      0.098363
_diffrn_orient_matrix_UB_23      -0.023548
_diffrn_orient_matrix_UB_31      0.042389
_diffrn_orient_matrix_UB_32      0.011238
_diffrn_orient_matrix_UB_33      -0.001545
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3490
_reflns_number_total             3718
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_coef       0.024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3718
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1149
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C17(H17A,H17B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C23(H23), C22(H22), C11(H11), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 Cl 0.31252(12) 0.72251(11) 0.58334(3) 0.0773(3) Uani 1 1 d . . . . .
O2 O 0.5565(2) 0.2747(2) 0.33621(10) 0.0615(6) Uani 1 1 d . . . . .
O3 O 0.3132(2) 0.2687(2) 0.33578(8) 0.0473(5) Uani 1 1 d . . . . .
O1 O 0.4332(2) 0.4071(2) 0.19951(8) 0.0497(5) Uani 1 1 d . . . . .
N1 N 0.3149(2) 0.5591(2) 0.33221(9) 0.0443(5) Uani 1 1 d . . . . .
C6 C 0.2418(3) 0.5551(3) 0.23661(11) 0.0408(5) Uani 1 1 d . . . . .
C5 C 0.1526(3) 0.5951(3) 0.18418(12) 0.0504(6) Uani 1 1 d . . . . .
H5A H 0.0896 0.5181 0.1735 0.061 Uiso 1 1 calc R . . . .
H5B H 0.2154 0.6148 0.1511 0.061 Uiso 1 1 calc R . . . .
C16 C 0.4420(3) 0.3304(3) 0.32696(11) 0.0413(5) Uani 1 1 d . . . . .
C8 C 0.4277(3) 0.4785(2) 0.30273(10) 0.0391(5) Uani 1 1 d . . . . .
C7 C 0.3695(3) 0.4715(2) 0.23813(10) 0.0396(5) Uani 1 1 d . . . . .
C9 C 0.3180(3) 0.5990(3) 0.39305(10) 0.0400(5) Uani 1 1 d . . . . .
C18 C 0.2965(3) 0.1181(3) 0.42249(12) 0.0459(6) Uani 1 1 d . . . . .
C10 C 0.3879(3) 0.7197(3) 0.41080(12) 0.0498(6) Uani 1 1 d . . . . .
H10 H 0.4352 0.7753 0.3834 0.060 Uiso 1 1 calc R . . . .
C1 C 0.2162(3) 0.6037(3) 0.29205(11) 0.0416(5) Uani 1 1 d . . . . .
C17 C 0.3152(4) 0.1237(3) 0.35700(13) 0.0524(7) Uani 1 1 d . . . . .
H17A H 0.4062 0.0802 0.3464 0.063 Uiso 1 1 calc R . . . .
H17B H 0.2381 0.0713 0.3383 0.063 Uiso 1 1 calc R . . . .
C15 C 0.5742(3) 0.5521(3) 0.30282(13) 0.0506(6) Uani 1 1 d . . . . .
H15A H 0.5627 0.6464 0.2890 0.076 Uiso 1 1 calc GR . . . .
H15B H 0.6397 0.5028 0.2775 0.076 Uiso 1 1 calc GR . . . .
H15C H 0.6123 0.5535 0.3420 0.076 Uiso 1 1 calc GR . . . .
C13 C 0.2477(4) 0.5540(3) 0.49276(12) 0.0571(7) Uani 1 1 d . . . . .
H13 H 0.2011 0.4984 0.5204 0.069 Uiso 1 1 calc R . . . .
C14 C 0.2480(3) 0.5159(3) 0.43389(12) 0.0532(7) Uani 1 1 d . . . . .
H14 H 0.2012 0.4346 0.4219 0.064 Uiso 1 1 calc R . . . .
C23 C 0.4023(4) 0.1680(4) 0.45990(13) 0.0594(8) Uani 1 1 d . . . . .
H23 H 0.4869 0.2048 0.4442 0.071 Uiso 1 1 calc R . . . .
C2 C 0.0942(4) 0.6987(4) 0.30769(14) 0.0642(8) Uani 1 1 d . . . . .
H2A H 0.1318 0.7908 0.3170 0.077 Uiso 1 1 calc R . . . .
H2B H 0.0454 0.6629 0.3422 0.077 Uiso 1 1 calc R . . . .
C12 C 0.3169(3) 0.6748(3) 0.50964(11) 0.0488(6) Uani 1 1 d . . . . .
C22 C 0.3847(4) 0.1641(4) 0.52033(15) 0.0679(9) Uani 1 1 d . . . . .
H22 H 0.4561 0.1998 0.5449 0.081 Uiso 1 1 calc R . . . .
C11 C 0.3873(3) 0.7580(3) 0.46950(12) 0.0534(7) Uani 1 1 d . . . . .
H11 H 0.4340 0.8392 0.4816 0.064 Uiso 1 1 calc R . . . .
C19 C 0.1722(3) 0.0602(3) 0.44700(15) 0.0592(7) Uani 1 1 d . . . . .
H19 H 0.0999 0.0252 0.4228 0.071 Uiso 1 1 calc R . . . .
C4 C 0.0621(4) 0.7243(4) 0.19839(15) 0.0634(8) Uani 1 1 d . . . . .
H4A H 0.1242 0.8061 0.1991 0.076 Uiso 1 1 calc R . . . .
H4B H -0.0093 0.7379 0.1678 0.076 Uiso 1 1 calc R . . . .
C3 C -0.0138(4) 0.7103(5) 0.25712(17) 0.0720(9) Uani 1 1 d . . . . .
H3A H -0.0748 0.6277 0.2566 0.086 Uiso 1 1 calc R . . . .
H3B H -0.0752 0.7912 0.2634 0.086 Uiso 1 1 calc R . . . .
C20 C 0.1565(4) 0.0549(4) 0.50728(16) 0.0705(9) Uani 1 1 d . . . . .
H20 H 0.0738 0.0151 0.5233 0.085 Uiso 1 1 calc R . . . .
C21 C 0.2610(4) 0.1073(4) 0.54371(15) 0.0672(9) Uani 1 1 d . . . . .
H21 H 0.2483 0.1044 0.5842 0.081 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 C12 1.741(3) . ?
O2 C16 1.204(3) . ?
O3 C16 1.346(3) . ?
O3 C17 1.468(3) . ?
O1 C7 1.225(3) . ?
N1 C8 1.462(3) . ?
N1 C9 1.438(3) . ?
N1 C1 1.362(3) . ?
C6 C5 1.502(4) . ?
C6 C7 1.427(4) . ?
C6 C1 1.367(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.526(4) . ?
C16 C8 1.524(3) . ?
C8 C7 1.569(3) . ?
C8 C15 1.528(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.385(4) . ?
C18 C17 1.503(4) . ?
C18 C23 1.383(4) . ?
C18 C19 1.393(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(4) . ?
C1 C2 1.491(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.390(4) . ?
C13 C12 1.375(4) . ?
C14 H14 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.387(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.530(5) . ?
C12 C11 1.376(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.375(5) . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.382(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.518(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C21 1.370(6) . ?
C21 H21 0.9300 . ?

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
C16 O3 C17 116.9(2) . . ?
C9 N1 C8 124.6(2) . . ?
C1 N1 C8 109.62(19) . . ?
C1 N1 C9 125.3(2) . . ?
C7 C6 C5 128.1(2) . . ?
C1 C6 C5 123.6(2) . . ?
C1 C6 C7 108.2(2) . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C6 C5 C4 109.8(2) . . ?
H5A C5 H5B 108.2 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
O2 C16 O3 124.0(2) . . ?
O2 C16 C8 123.4(2) . . ?
O3 C16 C8 112.6(2) . . ?
N1 C8 C16 112.6(2) . . ?
N1 C8 C7 102.02(18) . . ?
N1 C8 C15 113.0(2) . . ?
C16 C8 C7 109.28(19) . . ?
C16 C8 C15 110.5(2) . . ?
C15 C8 C7 109.0(2) . . ?
O1 C7 C6 131.5(2) . . ?
O1 C7 C8 122.0(2) . . ?
C6 C7 C8 106.5(2) . . ?
C10 C9 N1 120.8(2) . . ?
C10 C9 C14 120.0(2) . . ?
C14 C9 N1 119.1(2) . . ?
C23 C18 C17 121.2(2) . . ?
C23 C18 C19 118.3(3) . . ?
C19 C18 C17 120.5(3) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
N1 C1 C6 113.5(2) . . ?
N1 C1 C2 122.5(2) . . ?
C6 C1 C2 124.0(2) . . ?
O3 C17 C18 111.0(2) . . ?
O3 C17 H17A 109.4 . . ?
O3 C17 H17B 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(3) . . ?
C9 C14 C13 120.0(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C18 C23 H23 119.3 . . ?
C18 C23 C22 121.3(3) . . ?
C22 C23 H23 119.3 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.0(3) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C13 C12 Cl1 118.6(2) . . ?
C13 C12 C11 121.3(3) . . ?
C11 C12 Cl1 120.0(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 C23 119.5(3) . . ?
C21 C22 H22 120.2 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C3 C4 C5 111.7(3) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 C2 111.6(3) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.9(3) . . ?
C20 C21 H21 120.1 . . ?

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
Cl1 C12 C11 C10 -179.0(2) . . . . ?
O2 C16 C8 N1 -137.6(3) . . . . ?
O2 C16 C8 C7 109.7(3) . . . . ?
O2 C16 C8 C15 -10.2(4) . . . . ?
O3 C16 C8 N1 43.5(3) . . . . ?
O3 C16 C8 C7 -69.2(3) . . . . ?
O3 C16 C8 C15 170.9(2) . . . . ?
N1 C8 C7 O1 -177.6(2) . . . . ?
N1 C8 C7 C6 4.6(2) . . . . ?
N1 C9 C10 C11 178.7(3) . . . . ?
N1 C9 C14 C13 -178.9(3) . . . . ?
N1 C1 C2 C3 -169.9(3) . . . . ?
C6 C5 C4 C3 -47.1(4) . . . . ?
C6 C1 C2 C3 11.3(5) . . . . ?
C5 C6 C7 O1 -4.2(5) . . . . ?
C5 C6 C7 C8 173.3(2) . . . . ?
C5 C6 C1 N1 -176.9(2) . . . . ?
C5 C6 C1 C2 2.0(4) . . . . ?
C5 C4 C3 C2 62.9(4) . . . . ?
C16 O3 C17 C18 97.2(3) . . . . ?
C16 C8 C7 O1 -58.1(3) . . . . ?
C16 C8 C7 C6 124.0(2) . . . . ?
C8 N1 C9 C10 85.9(3) . . . . ?
C8 N1 C9 C14 -95.1(3) . . . . ?
C8 N1 C1 C6 4.1(3) . . . . ?
C8 N1 C1 C2 -174.9(3) . . . . ?
C7 C6 C5 C4 -159.4(3) . . . . ?
C7 C6 C1 N1 -0.8(3) . . . . ?
C7 C6 C1 C2 178.1(3) . . . . ?
C9 N1 C8 C16 64.7(3) . . . . ?
C9 N1 C8 C7 -178.2(2) . . . . ?
C9 N1 C8 C15 -61.4(3) . . . . ?
C9 N1 C1 C6 177.1(2) . . . . ?
C9 N1 C1 C2 -1.8(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C18 C23 C22 C21 1.3(6) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C1 N1 C8 C16 -122.2(2) . . . . ?
C1 N1 C8 C7 -5.1(3) . . . . ?
C1 N1 C8 C15 111.7(3) . . . . ?
C1 N1 C9 C10 -86.2(3) . . . . ?
C1 N1 C9 C14 92.8(3) . . . . ?
C1 C6 C5 C4 15.9(4) . . . . ?
C1 C6 C7 O1 179.9(3) . . . . ?
C1 C6 C7 C8 -2.5(3) . . . . ?
C1 C2 C3 C4 -42.5(4) . . . . ?
C17 O3 C16 O2 -1.1(4) . . . . ?
C17 O3 C16 C8 177.8(2) . . . . ?
C17 C18 C23 C22 179.4(3) . . . . ?
C17 C18 C19 C20 179.6(3) . . . . ?
C15 C8 C7 O1 62.7(3) . . . . ?
C15 C8 C7 C6 -115.1(2) . . . . ?
C13 C12 C11 C10 0.3(5) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C14 C13 C12 Cl1 178.8(2) . . . . ?
C14 C13 C12 C11 -0.5(5) . . . . ?
C23 C18 C17 O3 -68.0(4) . . . . ?
C23 C18 C19 C20 0.6(5) . . . . ?
C23 C22 C21 C20 0.1(6) . . . . ?
C12 C13 C14 C9 0.3(5) . . . . ?
C19 C18 C17 O3 113.0(3) . . . . ?
C19 C18 C23 C22 -1.6(5) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
