# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3659
_database_code_depnum_ccdc_archive 'CCDC 1412881'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-06-10
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            '[3+2] + DA product'
_chemical_name_systematic        'compound 18'
_chemical_formula_moiety         'C26 H33 Cl O4'
_chemical_formula_sum            'C26 H33 Cl O4'
_chemical_formula_weight         444.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H18Cl1O4
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'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.8200(5)
_cell_length_b                   14.6670(7)
_cell_length_c                   12.6709(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.774(5)
_cell_angle_gamma                90
_cell_volume                     2332.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      28.2520
_cell_measurement_theta_min      3.2260
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12808
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.085
_diffrn_reflns_theta_min         2.889
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8497
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   40.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  150.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0382228000
_diffrn_orient_matrix_UB_12      0.0353701000
_diffrn_orient_matrix_UB_13      -0.0129835000
_diffrn_orient_matrix_UB_21      -0.0037933000
_diffrn_orient_matrix_UB_22      -0.0088875000
_diffrn_orient_matrix_UB_23      -0.0556737000
_diffrn_orient_matrix_UB_31      -0.0414408000
_diffrn_orient_matrix_UB_32      -0.0317852000
_diffrn_orient_matrix_UB_33      0.0011373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3699
_reflns_number_total             5308
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+1.3452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1114
_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 Ternary CH refined with riding coordinates:
 C4(H4), C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C19(H19)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.08478(14) 0.63628(13) 0.40172(15) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.06819(14) 0.71489(14) 0.45055(16) 0.0233(4) Uani 1 1 d . . . . .
C3 C 0.15570(15) 0.77507(14) 0.49739(15) 0.0230(4) Uani 1 1 d . . . . .
C4 C 0.26871(14) 0.74156(13) 0.49299(14) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.2944 0.7033 0.5585 0.024 Uiso 1 1 calc R U . . .
C5 C 0.34367(15) 0.82059(13) 0.49763(15) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.36825(15) 0.85826(14) 0.40972(15) 0.0238(4) Uani 1 1 d . . . . .
H6 H 0.4179 0.9071 0.4175 0.029 Uiso 1 1 calc R U . . .
C7 C 0.32030(15) 0.82577(13) 0.30244(15) 0.0240(4) Uani 1 1 d . . . . .
C8 C 0.25085(15) 0.74181(13) 0.29214(15) 0.0220(4) Uani 1 1 d . . . . .
H8A H 0.2636 0.7050 0.2305 0.026 Uiso 1 1 calc R U . . .
H8B H 0.1752 0.7609 0.2761 0.026 Uiso 1 1 calc R U . . .
C9 C 0.27098(14) 0.68196(13) 0.39366(15) 0.0193(4) Uani 1 1 d . . . . .
H9 H 0.3441 0.6555 0.4022 0.023 Uiso 1 1 calc R U . . .
C10 C 0.19241(14) 0.60259(13) 0.39179(15) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.23670(15) 0.53051(13) 0.47985(15) 0.0229(4) Uani 1 1 d . . . . .
H11A H 0.2842 0.5593 0.5424 0.028 Uiso 1 1 calc R U . . .
H11B H 0.1780 0.4989 0.5050 0.028 Uiso 1 1 calc R U . . .
C12 C 0.29787(15) 0.46521(13) 0.42279(16) 0.0231(4) Uani 1 1 d . . . . .
C13 C 0.25253(15) 0.47080(14) 0.30200(16) 0.0246(4) Uani 1 1 d . . . . .
H13A H 0.2219 0.4114 0.2743 0.030 Uiso 1 1 calc R U . . .
H13B H 0.3089 0.4878 0.2627 0.030 Uiso 1 1 calc R U . . .
C14 C 0.16553(14) 0.54449(13) 0.28770(15) 0.0206(4) Uani 1 1 d . . . . .
H14 H 0.1697 0.5832 0.2237 0.025 Uiso 1 1 calc R U . . .
C15 C 0.04845(15) 0.51334(13) 0.28182(16) 0.0236(4) Uani 1 1 d . . . . .
C16 C 0.45351(17) 0.92430(15) 0.61521(18) 0.0339(5) Uani 1 1 d . . . . .
H16A H 0.5172 0.9096 0.5869 0.051 Uiso 1 1 calc R U . . .
H16B H 0.4743 0.9383 0.6923 0.051 Uiso 1 1 calc R U . . .
H16C H 0.4177 0.9773 0.5767 0.051 Uiso 1 1 calc R U . . .
C17 C -0.01929(15) 0.53005(14) 0.17001(16) 0.0270(5) Uani 1 1 d . . . . .
H17A H 0.0096 0.4931 0.1172 0.032 Uiso 1 1 calc R U . . .
H17B H -0.0127 0.5950 0.1511 0.032 Uiso 1 1 calc R U . . .
C18 C -0.13803(15) 0.50727(15) 0.15887(18) 0.0311(5) Uani 1 1 d . . . . .
H18A H -0.1476 0.4403 0.1552 0.037 Uiso 1 1 calc R U . . .
H18B H -0.1628 0.5295 0.2233 0.037 Uiso 1 1 calc R U . . .
C19 C -0.20435(16) 0.54997(15) 0.05966(18) 0.0311(5) Uani 1 1 d . . . . .
H19 H -0.2140 0.5161 -0.0055 0.037 Uiso 1 1 calc R U . . .
C20 C -0.25035(16) 0.63103(15) 0.05579(18) 0.0324(5) Uani 1 1 d . . . . .
C21 C -0.31298(17) 0.66952(17) -0.0484(2) 0.0394(6) Uani 1 1 d . . . . .
H21A H -0.3092 0.6274 -0.1076 0.059 Uiso 1 1 calc R U . . .
H21B H -0.2829 0.7286 -0.0627 0.059 Uiso 1 1 calc R U . . .
H21C H -0.3875 0.6776 -0.0427 0.059 Uiso 1 1 calc R U . . .
C22 C -0.2419(2) 0.69202(19) 0.1521(2) 0.0548(7) Uani 1 1 d . . . . .
H22A H -0.3086 0.6897 0.1785 0.082 Uiso 1 1 calc R U . . .
H22B H -0.2286 0.7548 0.1317 0.082 Uiso 1 1 calc R U . . .
H22C H -0.1829 0.6715 0.2091 0.082 Uiso 1 1 calc R U . . .
C23 C 0.38261(16) 0.41601(14) 0.46922(17) 0.0280(5) Uani 1 1 d . . . . .
C24 C 0.42403(17) 0.41482(15) 0.58935(18) 0.0347(5) Uani 1 1 d . . . . .
H24A H 0.3770 0.4513 0.6248 0.052 Uiso 1 1 calc R U . . .
H24B H 0.4961 0.4405 0.6058 0.052 Uiso 1 1 calc R U . . .
H24C H 0.4259 0.3519 0.6156 0.052 Uiso 1 1 calc R U . . .
C25 C 0.44637(17) 0.36042(15) 0.40527(19) 0.0355(5) Uani 1 1 d . . . . .
H25A H 0.4100 0.3597 0.3293 0.053 Uiso 1 1 calc R U . . .
H25B H 0.4533 0.2979 0.4331 0.053 Uiso 1 1 calc R U . . .
H25C H 0.5173 0.3874 0.4117 0.053 Uiso 1 1 calc R U . . .
C31 C 0.03242(17) 0.41855(14) 0.32370(18) 0.0311(5) Uani 1 1 d . . . . .
H31A H 0.0834 0.4084 0.3916 0.047 Uiso 1 1 calc R U . . .
H31B H 0.0439 0.3731 0.2705 0.047 Uiso 1 1 calc R U . . .
H31C H -0.0404 0.4130 0.3360 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl -0.05950(4) 0.75186(4) 0.45367(5) 0.03463(15) Uani 1 1 d . . . . .
O1 O 0.00774(10) 0.57977(9) 0.35467(11) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.14251(11) 0.84768(10) 0.53927(12) 0.0314(3) Uani 1 1 d . . . . .
O3 O 0.38222(11) 0.84764(10) 0.60006(10) 0.0282(3) Uani 1 1 d . . . . .
O4 O 0.33506(13) 0.86625(10) 0.22253(11) 0.0379(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
C1 C2 1.346(3) . ?
C1 C10 1.495(3) . ?
C1 O1 1.333(2) . ?
C2 C3 1.455(3) . ?
C2 Cl1 1.7325(19) . ?
C3 C4 1.542(3) . ?
C3 O2 1.217(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.499(3) . ?
C4 C9 1.538(3) . ?
C5 C6 1.337(3) . ?
C5 O3 1.351(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.453(3) . ?
C7 C8 1.510(3) . ?
C7 O4 1.221(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.535(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.536(3) . ?
C10 C11 1.558(3) . ?
C10 C14 1.549(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.512(3) . ?
C12 C13 1.525(3) . ?
C12 C23 1.336(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.537(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.556(3) . ?
C15 C17 1.523(3) . ?
C15 C31 1.517(3) . ?
C15 O1 1.507(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 O3 1.437(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.537(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.503(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.324(3) . ?
C20 C21 1.508(3) . ?
C20 C22 1.499(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.506(3) . ?
C23 C25 1.503(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
C2 C1 C10 123.86(17) . . ?
O1 C1 C2 124.47(17) . . ?
O1 C1 C10 111.66(16) . . ?
C1 C2 C3 121.73(17) . . ?
C1 C2 Cl1 121.16(15) . . ?
C3 C2 Cl1 117.02(15) . . ?
C2 C3 C4 116.35(17) . . ?
O2 C3 C2 122.98(18) . . ?
O2 C3 C4 120.67(18) . . ?
C3 C4 H4 107.6 . . ?
C5 C4 C3 110.59(16) . . ?
C5 C4 H4 107.6 . . ?
C5 C4 C9 110.65(15) . . ?
C9 C4 C3 112.69(15) . . ?
C9 C4 H4 107.6 . . ?
C6 C5 C4 123.01(17) . . ?
C6 C5 O3 125.23(18) . . ?
O3 C5 C4 111.76(16) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.14(18) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 118.54(17) . . ?
O4 C7 C6 120.57(18) . . ?
O4 C7 C8 120.88(17) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.50(15) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C4 C9 H9 107.8 . . ?
C8 C9 C4 109.43(15) . . ?
C8 C9 H9 107.8 . . ?
C8 C9 C10 115.01(15) . . ?
C10 C9 C4 108.76(15) . . ?
C10 C9 H9 107.8 . . ?
C1 C10 C9 111.21(16) . . ?
C1 C10 C11 111.82(16) . . ?
C1 C10 C14 101.81(14) . . ?
C9 C10 C11 111.17(15) . . ?
C9 C10 C14 117.47(15) . . ?
C14 C10 C11 102.81(15) . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 C10 103.67(15) . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C11 C12 C13 108.50(15) . . ?
C23 C12 C11 125.86(18) . . ?
C23 C12 C13 125.45(18) . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
C12 C13 C14 105.96(15) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C10 C14 H14 109.8 . . ?
C10 C14 C15 104.31(15) . . ?
C13 C14 C10 104.86(14) . . ?
C13 C14 H14 109.8 . . ?
C13 C14 C15 117.96(16) . . ?
C15 C14 H14 109.8 . . ?
C17 C15 C14 111.02(16) . . ?
C31 C15 C14 116.78(16) . . ?
C31 C15 C17 112.38(16) . . ?
O1 C15 C14 103.42(14) . . ?
O1 C15 C17 105.23(15) . . ?
O1 C15 C31 106.84(16) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
C15 C17 H17A 108.6 . . ?
C15 C17 H17B 108.6 . . ?
C15 C17 C18 114.62(17) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.52(17) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19 117.4 . . ?
C20 C19 C18 125.2(2) . . ?
C20 C19 H19 117.4 . . ?
C19 C20 C21 121.5(2) . . ?
C19 C20 C22 123.2(2) . . ?
C22 C20 C21 115.3(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C23 C24 122.57(19) . . ?
C12 C23 C25 122.6(2) . . ?
C25 C23 C24 114.84(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 C31 H31A 109.5 . . ?
C15 C31 H31B 109.5 . . ?
C15 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 O1 C15 111.00(14) . . ?
C5 O3 C16 117.14(16) . . ?

_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.962
_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.
;
_shelxl_version_number           2013-3
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pet/EtOAc'
####################################################################### 
# 
# 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_mx2752
_database_code_depnum_ccdc_archive 'CCDC 1412934'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'compound 8'
_chemical_name_common            '[3+2] product'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 Cl O2'
_chemical_formula_sum            'C21 H27 Cl O2'
_chemical_formula_weight         346.88

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.418(2)
_cell_length_b                   10.301(3)
_cell_length_c                   10.919(3)
_cell_angle_alpha                75.398(15)
_cell_angle_beta                 77.071(16)
_cell_angle_gamma                72.538(15)
_cell_volume                     965.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3396
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12563
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4412
_reflns_number_gt                3880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_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)+(0.0514P)²+0.4389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4412
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_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 0.27040(6) 0.30348(6) 0.88915(6) 0.04045(18) Uani 1 1 d . . .
O1 O 0.57924(15) 0.33933(16) 0.89396(14) 0.0325(3) Uani 1 1 d . . .
O2 O 0.23308(17) 0.07341(18) 1.11327(17) 0.0430(4) Uani 1 1 d . . .
C1 C 0.7458(2) 0.3101(2) 0.8922(2) 0.0299(5) Uani 1 1 d . . .
C2 C 0.7800(2) 0.1921(2) 1.01075(19) 0.0284(4) Uani 1 1 d . . .
H2 H 0.8290 0.1013 0.9831 0.034 Uiso 1 1 calc R . .
C3 C 0.6215(2) 0.1908(2) 1.0899(2) 0.0284(4) Uani 1 1 d . . .
C4 C 0.5217(2) 0.2512(2) 0.99098(19) 0.0281(4) Uani 1 1 d . . .
C5 C 0.3900(2) 0.2209(2) 1.0002(2) 0.0305(5) Uani 1 1 d . . .
C6 C 0.3529(2) 0.1044(2) 1.0985(2) 0.0327(5) Uani 1 1 d . . .
C7 C 0.4719(2) 0.0199(2) 1.1753(2) 0.0332(5) Uani 1 1 d . . .
H7 H 0.4579 -0.0640 1.2311 0.040 Uiso 1 1 calc R . .
C8 C 0.5983(2) 0.0563(2) 1.1696(2) 0.0321(5) Uani 1 1 d . . .
H8 H 0.6741 -0.0043 1.2170 0.039 Uiso 1 1 calc R . .
C9 C 0.5974(2) 0.2953(3) 1.1800(2) 0.0333(5) Uani 1 1 d . . .
H9A H 0.5486 0.3909 1.1388 0.040 Uiso 1 1 calc R . .
H9B H 0.5336 0.2687 1.2624 0.040 Uiso 1 1 calc R . .
C10 C 0.7540(2) 0.2863(2) 1.2009(2) 0.0317(5) Uani 1 1 d . . .
C11 C 0.8697(2) 0.2130(3) 1.1028(2) 0.0335(5) Uani 1 1 d . . .
H11A H 0.9287 0.1224 1.1452 0.040 Uiso 1 1 calc R . .
H11B H 0.9400 0.2702 1.0556 0.040 Uiso 1 1 calc R . .
C12 C 0.7830(3) 0.3357(3) 1.2917(2) 0.0367(5) Uani 1 1 d . . .
C13 C 0.9410(3) 0.3273(3) 1.3059(3) 0.0519(7) Uani 1 1 d . . .
H13A H 0.9600 0.2755 1.3917 0.078 Uiso 1 1 calc R . .
H13B H 0.9527 0.4213 1.2941 0.078 Uiso 1 1 calc R . .
H13C H 1.0131 0.2798 1.2413 0.078 Uiso 1 1 calc R . .
C14 C 0.6596(3) 0.4058(3) 1.3862(2) 0.0502(7) Uani 1 1 d . . .
H14A H 0.5615 0.4194 1.3615 0.075 Uiso 1 1 calc R . .
H14B H 0.6741 0.4961 1.3863 0.075 Uiso 1 1 calc R . .
H14C H 0.6630 0.3475 1.4721 0.075 Uiso 1 1 calc R . .
C15 C 0.7749(3) 0.4469(2) 0.8925(2) 0.0376(5) Uani 1 1 d . . .
H15A H 0.7389 0.5165 0.8189 0.056 Uiso 1 1 calc R . .
H15B H 0.8833 0.4345 0.8868 0.056 Uiso 1 1 calc R . .
H15C H 0.7213 0.4783 0.9720 0.056 Uiso 1 1 calc R . .
C16 C 0.8185(2) 0.2593(2) 0.7672(2) 0.0329(5) Uani 1 1 d . . .
H16A H 0.7837 0.3330 0.6943 0.039 Uiso 1 1 calc R . .
H16B H 0.7849 0.1771 0.7669 0.039 Uiso 1 1 calc R . .
C17 C 0.9916(2) 0.2205(3) 0.7482(2) 0.0368(5) Uani 1 1 d . . .
H17A H 1.0268 0.3063 0.7171 0.044 Uiso 1 1 calc R . .
H17B H 1.0254 0.1742 0.8317 0.044 Uiso 1 1 calc R . .
C18 C 1.0610(3) 0.1259(3) 0.6543(2) 0.0397(5) Uani 1 1 d . . .
H18 H 1.0169 0.0514 0.6644 0.048 Uiso 1 1 calc R . .
C19 C 1.1760(3) 0.1323(3) 0.5590(2) 0.0484(7) Uani 1 1 d . . .
C20 C 1.2339(4) 0.0221(4) 0.4789(3) 0.0735(10) Uani 1 1 d . . .
H20A H 1.3384 -0.0270 0.4894 0.110 Uiso 1 1 calc R . .
H20B H 1.2297 0.0655 0.3885 0.110 Uiso 1 1 calc R . .
H20C H 1.1712 -0.0440 0.5066 0.110 Uiso 1 1 calc R . .
C21 C 1.2576(4) 0.2437(4) 0.5244(3) 0.0793(11) Uani 1 1 d . . .
H21A H 1.1967 0.3225 0.5639 0.119 Uiso 1 1 calc R . .
H21B H 1.2750 0.2743 0.4310 0.119 Uiso 1 1 calc R . .
H21C H 1.3546 0.2074 0.5556 0.119 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 C5 1.726(2) . ?
O1 C4 1.339(2) . ?
O1 C1 1.502(2) . ?
O2 C6 1.229(3) . ?
C1 C15 1.516(3) . ?
C1 C16 1.527(3) . ?
C1 C2 1.554(3) . ?
C2 C11 1.539(3) . ?
C2 C3 1.551(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.484(3) . ?
C3 C8 1.488(3) . ?
C3 C9 1.570(3) . ?
C4 C5 1.344(3) . ?
C5 C6 1.466(3) . ?
C6 C7 1.478(3) . ?
C7 C8 1.336(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C12 1.333(3) . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.505(3) . ?
C12 C14 1.507(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.536(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.500(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.328(3) . ?
C18 H18 0.9500 . ?
C19 C21 1.493(5) . ?
C19 C20 1.506(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C4 O1 C1 109.67(15) . . ?
O1 C1 C15 106.24(17) . . ?
O1 C1 C16 104.50(15) . . ?
C15 C1 C16 112.27(18) . . ?
O1 C1 C2 105.03(15) . . ?
C15 C1 C2 116.35(18) . . ?
C16 C1 C2 111.31(17) . . ?
C11 C2 C3 105.17(16) . . ?
C11 C2 C1 117.48(18) . . ?
C3 C2 C1 103.38(16) . . ?
C11 C2 H2 110.1 . . ?
C3 C2 H2 110.1 . . ?
C1 C2 H2 110.1 . . ?
C4 C3 C8 113.01(17) . . ?
C4 C3 C2 102.67(17) . . ?
C8 C3 C2 117.93(18) . . ?
C4 C3 C9 110.53(17) . . ?
C8 C3 C9 109.04(18) . . ?
C2 C3 C9 103.09(16) . . ?
O1 C4 C5 125.2(2) . . ?
O1 C4 C3 111.34(17) . . ?
C5 C4 C3 123.4(2) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 Cl1 121.92(18) . . ?
C6 C5 Cl1 118.07(15) . . ?
O2 C6 C5 122.7(2) . . ?
O2 C6 C7 121.1(2) . . ?
C5 C6 C7 116.16(18) . . ?
C8 C7 C6 122.9(2) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C3 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 C3 105.25(16) . . ?
C10 C9 H9A 110.7 . . ?
C3 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C3 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C12 C10 C9 124.6(2) . . ?
C12 C10 C11 126.3(2) . . ?
C9 C10 C11 109.09(17) . . ?
C10 C11 C2 106.11(17) . . ?
C10 C11 H11A 110.5 . . ?
C2 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
C2 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C10 C12 C13 122.4(2) . . ?
C10 C12 C14 122.3(2) . . ?
C13 C12 C14 115.3(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 C17 112.69(17) . . ?
C1 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C1 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 111.98(18) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 128.7(3) . . ?
C19 C18 H18 115.6 . . ?
C17 C18 H18 115.6 . . ?
C18 C19 C21 124.1(3) . . ?
C18 C19 C20 120.4(3) . . ?
C21 C19 C20 115.5(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C4 O1 C1 C15 -126.73(18) . . . . ?
C4 O1 C1 C16 114.38(18) . . . . ?
C4 O1 C1 C2 -2.9(2) . . . . ?
O1 C1 C2 C11 -129.53(17) . . . . ?
C15 C1 C2 C11 -12.4(3) . . . . ?
C16 C1 C2 C11 117.95(19) . . . . ?
O1 C1 C2 C3 -14.26(19) . . . . ?
C15 C1 C2 C3 102.89(19) . . . . ?
C16 C1 C2 C3 -126.78(17) . . . . ?
C11 C2 C3 C4 148.55(18) . . . . ?
C1 C2 C3 C4 24.78(19) . . . . ?
C11 C2 C3 C8 -86.5(2) . . . . ?
C1 C2 C3 C8 149.70(18) . . . . ?
C11 C2 C3 C9 33.6(2) . . . . ?
C1 C2 C3 C9 -90.14(19) . . . . ?
C1 O1 C4 C5 -160.25(19) . . . . ?
C1 O1 C4 C3 20.5(2) . . . . ?
C8 C3 C4 O1 -157.08(17) . . . . ?
C2 C3 C4 O1 -29.0(2) . . . . ?
C9 C3 C4 O1 80.4(2) . . . . ?
C8 C3 C4 C5 23.6(3) . . . . ?
C2 C3 C4 C5 151.7(2) . . . . ?
C9 C3 C4 C5 -98.9(2) . . . . ?
O1 C4 C5 C6 168.80(18) . . . . ?
C3 C4 C5 C6 -12.0(3) . . . . ?
O1 C4 C5 Cl1 -4.3(3) . . . . ?
C3 C4 C5 Cl1 174.88(15) . . . . ?
C4 C5 C6 O2 178.6(2) . . . . ?
Cl1 C5 C6 O2 -8.0(3) . . . . ?
C4 C5 C6 C7 -4.9(3) . . . . ?
Cl1 C5 C6 C7 168.50(14) . . . . ?
O2 C6 C7 C8 -174.4(2) . . . . ?
C5 C6 C7 C8 9.0(3) . . . . ?
C6 C7 C8 C3 3.8(3) . . . . ?
C4 C3 C8 C7 -18.9(3) . . . . ?
C2 C3 C8 C7 -138.6(2) . . . . ?
C9 C3 C8 C7 104.4(2) . . . . ?
C4 C3 C9 C10 -138.73(18) . . . . ?
C8 C3 C9 C10 96.5(2) . . . . ?
C2 C3 C9 C10 -29.6(2) . . . . ?
C3 C9 C10 C12 -165.4(2) . . . . ?
C3 C9 C10 C11 14.7(2) . . . . ?
C12 C10 C11 C2 -173.5(2) . . . . ?
C9 C10 C11 C2 6.4(2) . . . . ?
C3 C2 C11 C10 -25.2(2) . . . . ?
C1 C2 C11 C10 89.1(2) . . . . ?
C9 C10 C12 C13 -178.3(2) . . . . ?
C11 C10 C12 C13 1.6(4) . . . . ?
C9 C10 C12 C14 0.9(4) . . . . ?
C11 C10 C12 C14 -179.3(2) . . . . ?
O1 C1 C16 C17 -178.86(18) . . . . ?
C15 C1 C16 C17 66.4(2) . . . . ?
C2 C1 C16 C17 -66.0(2) . . . . ?
C1 C16 C17 C18 159.6(2) . . . . ?
C16 C17 C18 C19 135.4(3) . . . . ?
C17 C18 C19 C21 -2.1(5) . . . . ?
C17 C18 C19 C20 177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pet/EtOAc'
