# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1586619'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H29 Cl O'
_chemical_formula_sum            'C20 H29 Cl O'
_chemical_formula_weight         320.88

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5588(6)
_cell_length_b                   6.9137(5)
_cell_length_c                   15.0132(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.591(2)
_cell_angle_gamma                90
_cell_volume                     875.96(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8308
_cell_measurement_theta_min      2.418
_cell_measurement_theta_max      33.104

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω- and \-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27999
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         35.084
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7622
_reflns_number_gt                6536
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXLS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.0087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2651 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7622
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_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 1.18927(4) 0.02818(5) 1.07414(2) 0.02161(8) Uani 1 1 d . . . . .
C8 C 0.93868(16) 0.0191(2) 0.82783(8) 0.0174(2) Uani 1 1 d . . . . .
H8A H 0.899137 0.095729 0.875146 0.021 Uiso 1 1 calc R U . . .
H8B H 0.860338 -0.083919 0.807794 0.021 Uiso 1 1 calc R U . . .
C10 C 1.08105(16) 0.3068(2) 0.77625(8) 0.0151(2) Uani 1 1 d . . . . .
H10 H 1.044819 0.384416 0.825177 0.018 Uiso 1 1 calc R U . . .
C1 C 1.19340(17) 0.18975(18) 0.98119(8) 0.0146(2) Uani 1 1 d . . . . .
H1 H 1.086578 0.251358 0.965970 0.018 Uiso 1 1 calc R U . . .
C6 C 1.22578(16) 0.07819(19) 0.89694(8) 0.0155(2) Uani 1 1 d . . . . .
H6 H 1.328397 0.007685 0.914096 0.019 Uiso 1 1 calc R U . . .
C5 C 1.24400(17) 0.2174(2) 0.81740(9) 0.0192(3) Uani 1 1 d . . . . .
C11 C 1.08693(19) 0.4450(2) 0.69718(10) 0.0209(3) Uani 1 1 d . . . . .
H11A H 1.170706 0.543016 0.714791 0.025 Uiso 1 1 calc R U . . .
H11B H 1.113191 0.371810 0.644951 0.025 Uiso 1 1 calc R U . . .
C12 C 0.92742(17) 0.5453(2) 0.67049(9) 0.0212(3) Uani 1 1 d . . . . .
H12A H 0.934221 0.636338 0.620383 0.025 Uiso 1 1 calc R U . . .
H12B H 0.903989 0.621629 0.722480 0.025 Uiso 1 1 calc R U . . .
C2 C 1.31428(17) 0.34943(19) 1.00933(9) 0.0177(2) Uani 1 1 d . . . . .
C7 C 1.09653(19) -0.07313(19) 0.86761(9) 0.0201(3) Uani 1 1 d . . . . .
H7A H 1.130866 -0.159788 0.822053 0.024 Uiso 1 1 calc R U . . .
H7B H 1.082379 -0.152833 0.920473 0.024 Uiso 1 1 calc R U . . .
C9 C 0.95363(16) 0.15063(19) 0.74765(8) 0.0151(2) Uani 1 1 d . . . . .
H9 H 0.990090 0.069015 0.700088 0.018 Uiso 1 1 calc R U . . .
C13 C 0.79134(17) 0.4035(2) 0.64097(9) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.78898(16) 0.23274(19) 0.70771(9) 0.0155(2) Uani 1 1 d . . . . .
H14 H 0.732139 0.272650 0.757789 0.019 Uiso 1 1 calc R U . . .
C17 C 0.79803(19) 0.3025(2) 0.55121(9) 0.0230(3) Uani 1 1 d . . . . .
C15 C 0.69124(18) 0.0779(2) 0.64894(10) 0.0218(3) Uani 1 1 d . . . . .
H15A H 0.713025 -0.052699 0.675090 0.026 Uiso 1 1 calc R U . . .
H15B H 0.576343 0.104725 0.642968 0.026 Uiso 1 1 calc R U . . .
C19 C 0.63357(17) 0.5154(3) 0.63204(10) 0.0249(3) Uani 1 1 d . . . . .
H19A H 0.634288 0.622040 0.589135 0.037 Uiso 1 1 calc R U . . .
H19B H 0.620771 0.567264 0.691139 0.037 Uiso 1 1 calc R U . . .
H19C H 0.545429 0.427838 0.610184 0.037 Uiso 1 1 calc R U . . .
C4 C 1.36738(19) 0.3728(3) 0.85329(11) 0.0283(4) Uani 1 1 d . . . . .
H4A H 1.471575 0.309636 0.871610 0.034 Uiso 1 1 calc R U . . .
H4B H 1.377368 0.464254 0.803794 0.034 Uiso 1 1 calc R U . . .
C3 C 1.3263(2) 0.4871(2) 0.93379(11) 0.0277(4) Uani 1 1 d . . . . .
H3A H 1.409533 0.584510 0.953701 0.033 Uiso 1 1 calc R U . . .
H3B H 1.224282 0.555524 0.915918 0.033 Uiso 1 1 calc R U . . .
C20 C 0.8382(3) 0.3854(3) 0.47822(11) 0.0376(4) Uani 1 1 d . . . . .
H20A H 0.836140 0.312394 0.424433 0.045 Uiso 1 1 calc R U . . .
H20B H 0.868963 0.517574 0.479934 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7473(2) 0.0947(3) 0.55704(10) 0.0263(3) Uani 1 1 d . . . . .
H16A H 0.837078 0.005993 0.554078 0.032 Uiso 1 1 calc R U . . .
H16B H 0.660053 0.063126 0.507118 0.032 Uiso 1 1 calc R U . . .
O1 O 1.39455(14) 0.35994(17) 1.08368(7) 0.0250(2) Uani 1 1 d . . . . .
C18 C 1.3158(2) 0.1008(3) 0.74641(10) 0.0340(4) Uani 1 1 d . . . . .
H18A H 1.240235 0.001556 0.720029 0.051 Uiso 1 1 calc R U . . .
H18B H 1.414163 0.038801 0.775406 0.051 Uiso 1 1 calc R U . . .
H18C H 1.338474 0.188033 0.698721 0.051 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 C1 1.7925(12) . ?
C8 C7 1.523(2) . ?
C8 C9 1.5309(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.5314(18) . ?
C10 C9 1.5436(19) . ?
C10 C5 1.5559(19) . ?
C10 H10 1.0000 . ?
C1 C2 1.5238(19) . ?
C1 C6 1.5453(17) . ?
C1 H1 1.0000 . ?
C6 C7 1.533(2) . ?
C6 C5 1.5618(18) . ?
C6 H6 1.0000 . ?
C5 C4 1.540(2) . ?
C5 C18 1.543(2) . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.531(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C2 O1 1.2114(17) . ?
C2 C3 1.497(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C14 1.5447(19) . ?
C9 H9 1.0000 . ?
C13 C17 1.527(2) . ?
C13 C19 1.543(2) . ?
C13 C14 1.5506(19) . ?
C14 C15 1.5420(19) . ?
C14 H14 1.0000 . ?
C17 C20 1.332(2) . ?
C17 C16 1.508(2) . ?
C15 C16 1.539(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 C3 1.533(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C7 C8 C9 111.85(11) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C11 C10 C9 109.50(10) . . ?
C11 C10 C5 114.36(11) . . ?
C9 C10 C5 112.20(11) . . ?
C11 C10 H10 106.8 . . ?
C9 C10 H10 106.8 . . ?
C5 C10 H10 106.8 . . ?
C2 C1 C6 112.49(11) . . ?
C2 C1 Cl1 109.64(9) . . ?
C6 C1 Cl1 110.84(9) . . ?
C2 C1 H1 107.9 . . ?
C6 C1 H1 107.9 . . ?
Cl1 C1 H1 107.9 . . ?
C7 C6 C1 110.89(11) . . ?
C7 C6 C5 111.11(11) . . ?
C1 C6 C5 111.87(11) . . ?
C7 C6 H6 107.6 . . ?
C1 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C4 C5 C18 106.12(14) . . ?
C4 C5 C10 112.28(13) . . ?
C18 C5 C10 111.51(11) . . ?
C4 C5 C6 108.21(11) . . ?
C18 C5 C6 107.94(13) . . ?
C10 C5 C6 110.56(11) . . ?
C12 C11 C10 110.13(12) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 112.94(13) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O1 C2 C3 124.05(14) . . ?
O1 C2 C1 123.61(13) . . ?
C3 C2 C1 112.30(11) . . ?
C8 C7 C6 112.17(11) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C9 C10 110.15(10) . . ?
C8 C9 C14 109.46(11) . . ?
C10 C9 C14 114.05(11) . . ?
C8 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
C14 C9 H9 107.6 . . ?
C17 C13 C12 114.19(12) . . ?
C17 C13 C19 108.27(12) . . ?
C12 C13 C19 108.46(12) . . ?
C17 C13 C14 103.23(11) . . ?
C12 C13 C14 113.06(11) . . ?
C19 C13 C14 109.42(12) . . ?
C15 C14 C9 109.87(11) . . ?
C15 C14 C13 102.87(11) . . ?
C9 C14 C13 114.92(11) . . ?
C15 C14 H14 109.6 . . ?
C9 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
C20 C17 C16 125.05(16) . . ?
C20 C17 C13 125.62(17) . . ?
C16 C17 C13 109.31(12) . . ?
C16 C15 C14 103.92(12) . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 C5 113.66(13) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C2 C3 C4 108.88(13) . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C17 C20 H20A 120.0 . . ?
C17 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C17 C16 C15 105.04(12) . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: H2O/CH2Cl2'
####################################################################### 
# 
# 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_25
_database_code_depnum_ccdc_archive 'CCDC 1586622'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H29 Cl O2'
_chemical_formula_sum            'C19 H29 Cl O2'
_chemical_formula_weight         324.87

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5312(3)
_cell_length_b                   20.9084(8)
_cell_length_c                   21.2244(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3342.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      31.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31190
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         31.065
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10688
_reflns_number_gt                10281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.0505P] 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_abs_structure_details 
;
 Flack x determined using 4448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10688
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1B Cl 1.08447(4) 0.67352(2) 0.53500(2) 0.01827(7) Uani 1 1 d . . . . .
Cl1A Cl 0.35359(5) 0.70948(2) 0.72265(2) 0.02239(8) Uani 1 1 d . . . . .
O1B O 0.79813(14) 0.69310(5) 0.63356(4) 0.01607(18) Uani 1 1 d . . . . .
O2A O -0.04502(13) 0.29802(5) 0.85865(5) 0.01871(19) Uani 1 1 d . . . . .
O2B O 0.30015(15) 0.33204(5) 0.48009(5) 0.0219(2) Uani 1 1 d . . . . .
O1A O 0.68158(13) 0.62228(5) 0.73907(5) 0.01749(19) Uani 1 1 d . . . . .
C17A C -0.06221(16) 0.33289(6) 0.81327(6) 0.0133(2) Uani 1 1 d . . . . .
C14B C 0.70756(17) 0.37697(6) 0.55123(6) 0.0127(2) Uani 1 1 d . . . . .
H14B H 0.778627 0.373097 0.590848 0.015 Uiso 1 1 calc R U . . .
C6A C 0.30492(16) 0.58415(6) 0.75947(6) 0.0120(2) Uani 1 1 d . . . . .
H6A H 0.371946 0.570416 0.721113 0.014 Uiso 1 1 calc R U . . .
C9A C 0.07447(16) 0.46898(6) 0.76002(6) 0.0117(2) Uani 1 1 d . . . . .
H9A H -0.000825 0.476430 0.798132 0.014 Uiso 1 1 calc R U . . .
C2B C 0.74366(17) 0.69797(6) 0.56909(6) 0.0132(2) Uani 1 1 d . . . . .
H2B H 0.759941 0.742984 0.554249 0.016 Uiso 1 1 calc R U . . .
C12B C 0.39403(18) 0.40431(6) 0.59336(6) 0.0154(2) Uani 1 1 d . . . . .
H12A H 0.269534 0.389346 0.590752 0.019 Uiso 1 1 calc R U . . .
H12B H 0.424791 0.408890 0.638486 0.019 Uiso 1 1 calc R U . . .
C5B C 0.62223(15) 0.56375(5) 0.53780(5) 0.01028(19) Uani 1 1 d . . . . .
C13B C 0.51523(17) 0.35431(6) 0.56360(6) 0.0128(2) Uani 1 1 d . . . . .
C10A C 0.26973(15) 0.46680(5) 0.78175(5) 0.01050(19) Uani 1 1 d . . . . .
H10A H 0.343335 0.458930 0.743314 0.013 Uiso 1 1 calc R U . . .
C6B C 0.82262(15) 0.58215(5) 0.54315(5) 0.0101(2) Uani 1 1 d . . . . .
H6B H 0.856847 0.576549 0.588338 0.012 Uiso 1 1 calc R U . . .
C11B C 0.40897(17) 0.46943(6) 0.56137(6) 0.0137(2) Uani 1 1 d . . . . .
H11A H 0.332328 0.500590 0.583592 0.016 Uiso 1 1 calc R U . . .
H11B H 0.366632 0.466026 0.517337 0.016 Uiso 1 1 calc R U . . .
C13A C 0.07725(17) 0.34370(6) 0.76179(6) 0.0129(2) Uani 1 1 d . . . . .
C16A C -0.22695(16) 0.37194(6) 0.79885(6) 0.0143(2) Uani 1 1 d . . . . .
H16A H -0.242893 0.406447 0.830290 0.017 Uiso 1 1 calc R U . . .
H16B H -0.334138 0.344533 0.798800 0.017 Uiso 1 1 calc R U . . .
C9B C 0.72092(16) 0.44608(5) 0.52587(5) 0.0114(2) Uani 1 1 d . . . . .
H9B H 0.681546 0.445646 0.480872 0.014 Uiso 1 1 calc R U . . .
C15B C 0.77612(19) 0.32796(6) 0.50209(7) 0.0180(2) Uani 1 1 d . . . . .
H15A H 0.874964 0.346229 0.477163 0.022 Uiso 1 1 calc R U . . .
H15B H 0.817942 0.288446 0.523077 0.022 Uiso 1 1 calc R U . . .
C15A C -0.19287(17) 0.39992(6) 0.73304(6) 0.0152(2) Uani 1 1 d . . . . .
H15C H -0.249951 0.442325 0.728504 0.018 Uiso 1 1 calc R U . . .
H15D H -0.238834 0.371077 0.699836 0.018 Uiso 1 1 calc R U . . .
C4B C 0.51644(17) 0.60940(6) 0.58081(6) 0.0134(2) Uani 1 1 d . . . . .
H4B1 H 0.388254 0.599737 0.576808 0.016 Uiso 1 1 calc R U . . .
H4B2 H 0.551133 0.601759 0.625168 0.016 Uiso 1 1 calc R U . . .
C4A C 0.53530(17) 0.52726(6) 0.82387(6) 0.0140(2) Uani 1 1 d . . . . .
H41A H 0.555787 0.495606 0.857786 0.017 Uiso 1 1 calc R U . . .
H4A2 H 0.596526 0.511670 0.785560 0.017 Uiso 1 1 calc R U . . .
C19B C 0.51303(19) 0.29232(6) 0.60335(6) 0.0169(2) Uani 1 1 d . . . . .
H19A H 0.561549 0.301171 0.645298 0.025 Uiso 1 1 calc R U . . .
H19B H 0.585471 0.259600 0.582559 0.025 Uiso 1 1 calc R U . . .
H19C H 0.390665 0.276906 0.607388 0.025 Uiso 1 1 calc R U . . .
C17B C 0.45339(19) 0.33360(6) 0.49783(6) 0.0155(2) Uani 1 1 d . . . . .
C8B C 0.91599(17) 0.46795(6) 0.52732(6) 0.0144(2) Uani 1 1 d . . . . .
H8B1 H 0.961575 0.464227 0.570921 0.017 Uiso 1 1 calc R U . . .
H8B2 H 0.987395 0.439206 0.500271 0.017 Uiso 1 1 calc R U . . .
C1A C 0.38646(18) 0.64755(6) 0.78113(6) 0.0153(2) Uani 1 1 d . . . . .
H4AO H 0.326880 0.661022 0.821093 0.018 Uiso 1 1 calc R U . . .
C5A C 0.33393(16) 0.53133(6) 0.81045(5) 0.0112(2) Uani 1 1 d . . . . .
C1B C 0.85137(17) 0.65274(6) 0.52710(6) 0.0123(2) Uani 1 1 d . . . . .
H1B H 0.815080 0.659857 0.482326 0.015 Uiso 1 1 calc R U . . .
C11A C 0.29626(17) 0.40892(6) 0.82534(6) 0.0136(2) Uani 1 1 d . . . . .
H11C H 0.418490 0.409281 0.842502 0.016 Uiso 1 1 calc R U . . .
H11D H 0.212230 0.411465 0.861124 0.016 Uiso 1 1 calc R U . . .
C10B C 0.60188(16) 0.49361(5) 0.56171(5) 0.01037(19) Uani 1 1 d . . . . .
H10B H 0.642193 0.493187 0.606595 0.012 Uiso 1 1 calc R U . . .
C8A C 0.04351(17) 0.52507(6) 0.71451(6) 0.0159(2) Uani 1 1 d . . . . .
H8A1 H 0.105289 0.516052 0.674306 0.019 Uiso 1 1 calc R U . . .
H8A2 H -0.085082 0.528429 0.705410 0.019 Uiso 1 1 calc R U . . .
C14A C 0.01195(17) 0.40572(6) 0.72906(6) 0.0126(2) Uani 1 1 d . . . . .
H14A H 0.049267 0.405173 0.683847 0.015 Uiso 1 1 calc R U . . .
C2A C 0.58663(18) 0.64227(6) 0.79330(6) 0.0160(2) Uani 1 1 d . . . . .
H2A H 0.633706 0.684317 0.808314 0.019 Uiso 1 1 calc R U . . .
C7B C 0.93976(17) 0.53684(6) 0.50474(6) 0.0154(2) Uani 1 1 d . . . . .
H7B1 H 0.907599 0.539865 0.459613 0.018 Uiso 1 1 calc R U . . .
H7B2 H 1.065748 0.549551 0.509250 0.018 Uiso 1 1 calc R U . . .
C3B C 0.54749(17) 0.67988(6) 0.56479(6) 0.0159(2) Uani 1 1 d . . . . .
H3B1 H 0.478363 0.706920 0.594186 0.019 Uiso 1 1 calc R U . . .
H3B2 H 0.504164 0.688427 0.521561 0.019 Uiso 1 1 calc R U . . .
C12A C 0.26502(17) 0.34700(6) 0.78882(6) 0.0153(2) Uani 1 1 d . . . . .
H12C H 0.284425 0.310073 0.817188 0.018 Uiso 1 1 calc R U . . .
H12D H 0.352069 0.344058 0.753990 0.018 Uiso 1 1 calc R U . . .
C3A C 0.61716(19) 0.59123(6) 0.84349(6) 0.0176(2) Uani 1 1 d . . . . .
H3A1 H 0.563664 0.605388 0.883751 0.021 Uiso 1 1 calc R U . . .
H3A2 H 0.746281 0.585646 0.850283 0.021 Uiso 1 1 calc R U . . .
C7A C 0.10923(17) 0.58903(6) 0.74046(7) 0.0165(2) Uani 1 1 d . . . . .
H7A1 H 0.037183 0.601264 0.777564 0.020 Uiso 1 1 calc R U . . .
H7A2 H 0.094987 0.622642 0.707992 0.020 Uiso 1 1 calc R U . . .
C19A C 0.06122(19) 0.28594(6) 0.71646(7) 0.0196(3) Uani 1 1 d . . . . .
H19D H 0.091972 0.246567 0.739004 0.029 Uiso 1 1 calc R U . . .
H19E H 0.142498 0.291773 0.680861 0.029 Uiso 1 1 calc R U . . .
H19F H -0.060936 0.282945 0.700832 0.029 Uiso 1 1 calc R U . . .
C18A C 0.23527(19) 0.54595(6) 0.87250(6) 0.0172(2) Uani 1 1 d . . . . .
H18A H 0.266995 0.513871 0.904222 0.026 Uiso 1 1 calc R U . . .
H18B H 0.106866 0.544762 0.865098 0.026 Uiso 1 1 calc R U . . .
H18C H 0.269263 0.588523 0.887597 0.026 Uiso 1 1 calc R U . . .
C16B C 0.6153(2) 0.31398(7) 0.45987(6) 0.0217(3) Uani 1 1 d . . . . .
H16C H 0.622477 0.338948 0.420320 0.026 Uiso 1 1 calc R U . . .
H16D H 0.609872 0.267928 0.449185 0.026 Uiso 1 1 calc R U . . .
C18B C 0.55221(18) 0.57005(6) 0.46950(6) 0.0173(2) Uani 1 1 d . . . . .
H18D H 0.422313 0.567305 0.469583 0.026 Uiso 1 1 calc R U . . .
H18E H 0.601177 0.535456 0.443645 0.026 Uiso 1 1 calc R U . . .
H18F H 0.588832 0.611391 0.452037 0.026 Uiso 1 1 calc R U . . .
H1BO H 0.876(3) 0.7188(10) 0.6375(10) 0.030(5) Uiso 1 1 d . . . . .
H1AO H 0.692(3) 0.6513(11) 0.7123(10) 0.033(6) Uiso 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
Cl1B C1B 1.8162(13) . ?
Cl1A C1A 1.8108(13) . ?
O1B C2B 1.4322(15) . ?
O1B H1BO 0.80(2) . ?
O2A C17A 1.2149(16) . ?
O2B C17B 1.2144(18) . ?
O1A C2A 1.4180(16) . ?
O1A H1AO 0.84(2) . ?
C17A C16A 1.5164(17) . ?
C17A C13A 1.5323(17) . ?
C14B C9B 1.5452(16) . ?
C14B C13B 1.5464(17) . ?
C14B C15B 1.5506(17) . ?
C14B H14B 1.0000 . ?
C6A C1A 1.5316(17) . ?
C6A C7A 1.5314(18) . ?
C6A C5A 1.5614(17) . ?
C6A H6A 1.0000 . ?
C9A C8A 1.5372(17) . ?
C9A C10A 1.5418(17) . ?
C9A C14A 1.5503(17) . ?
C9A H9A 1.0000 . ?
C2B C3B 1.5277(18) . ?
C2B C1B 1.5318(17) . ?
C2B H2B 1.0000 . ?
C12B C11B 1.5256(17) . ?
C12B C13B 1.5249(18) . ?
C12B H12A 0.9900 . ?
C12B H12B 0.9900 . ?
C5B C4B 1.5424(16) . ?
C5B C10B 1.5595(16) . ?
C5B C18B 1.5482(16) . ?
C5B C6B 1.5616(16) . ?
C13B C17B 1.5339(17) . ?
C13B C19B 1.5467(17) . ?
C10A C11A 1.5364(16) . ?
C10A C5A 1.5572(17) . ?
C10A H10A 1.0000 . ?
C6B C1B 1.5302(16) . ?
C6B C7B 1.5298(17) . ?
C6B H6B 1.0000 . ?
C11B C10B 1.5383(17) . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C13A C12A 1.5277(18) . ?
C13A C19A 1.5486(17) . ?
C13A C14A 1.5511(17) . ?
C16A C15A 1.5360(18) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C9B C8B 1.5389(17) . ?
C9B C10B 1.5395(16) . ?
C9B H9B 1.0000 . ?
C15B C16B 1.535(2) . ?
C15B H15A 0.9900 . ?
C15B H15B 0.9900 . ?
C15A C14A 1.5496(18) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C4B C3B 1.5302(17) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C4A C3A 1.5304(18) . ?
C4A C5A 1.5454(18) . ?
C4A H41A 0.9900 . ?
C4A H4A2 0.9900 . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
C17B C16B 1.518(2) . ?
C8B C7B 1.5286(18) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C1A C2A 1.5335(19) . ?
C1A H4AO 1.0000 . ?
C5A C18A 1.5428(17) . ?
C1B H1B 1.0000 . ?
C11A C12A 1.5271(18) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C10B H10B 1.0000 . ?
C8A C7A 1.5287(18) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C14A H14A 1.0000 . ?
C2A C3A 1.5254(19) . ?
C2A H2A 1.0000 . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 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
C2B O1B H1BO 105.2(15) . . ?
C2A O1A H1AO 112.7(16) . . ?
O2A C17A C16A 124.77(11) . . ?
O2A C17A C13A 125.50(11) . . ?
C16A C17A C13A 109.73(10) . . ?
C9B C14B C13B 113.99(10) . . ?
C9B C14B C15B 111.22(10) . . ?
C13B C14B C15B 102.92(10) . . ?
C9B C14B H14B 109.5 . . ?
C13B C14B H14B 109.5 . . ?
C15B C14B H14B 109.5 . . ?
C1A C6A C7A 114.03(10) . . ?
C1A C6A C5A 110.37(10) . . ?
C7A C6A C5A 111.38(10) . . ?
C1A C6A H6A 106.9 . . ?
C7A C6A H6A 106.9 . . ?
C5A C6A H6A 106.9 . . ?
C8A C9A C10A 110.81(10) . . ?
C8A C9A C14A 109.79(10) . . ?
C10A C9A C14A 113.03(10) . . ?
C8A C9A H9A 107.7 . . ?
C10A C9A H9A 107.7 . . ?
C14A C9A H9A 107.7 . . ?
O1B C2B C3B 108.45(10) . . ?
O1B C2B C1B 111.11(10) . . ?
C3B C2B C1B 108.93(10) . . ?
O1B C2B H2B 109.4 . . ?
C3B C2B H2B 109.4 . . ?
C1B C2B H2B 109.4 . . ?
C11B C12B C13B 112.54(10) . . ?
C11B C12B H12A 109.1 . . ?
C13B C12B H12A 109.1 . . ?
C11B C12B H12B 109.1 . . ?
C13B C12B H12B 109.1 . . ?
H12A C12B H12B 107.8 . . ?
C4B C5B C10B 109.80(9) . . ?
C4B C5B C18B 109.00(10) . . ?
C10B C5B C18B 110.56(9) . . ?
C4B C5B C6B 107.68(9) . . ?
C10B C5B C6B 107.64(9) . . ?
C18B C5B C6B 112.10(10) . . ?
C12B C13B C17B 112.88(11) . . ?
C12B C13B C19B 110.00(10) . . ?
C17B C13B C19B 104.87(10) . . ?
C12B C13B C14B 114.89(10) . . ?
C17B C13B C14B 102.50(10) . . ?
C19B C13B C14B 111.06(10) . . ?
C11A C10A C9A 109.12(10) . . ?
C11A C10A C5A 113.99(10) . . ?
C9A C10A C5A 112.80(10) . . ?
C11A C10A H10A 106.8 . . ?
C9A C10A H10A 106.8 . . ?
C5A C10A H10A 106.8 . . ?
C1B C6B C7B 113.40(10) . . ?
C1B C6B C5B 110.99(9) . . ?
C7B C6B C5B 111.47(9) . . ?
C1B C6B H6B 106.9 . . ?
C7B C6B H6B 106.9 . . ?
C5B C6B H6B 106.9 . . ?
C12B C11B C10B 111.15(10) . . ?
C12B C11B H11A 109.4 . . ?
C10B C11B H11A 109.4 . . ?
C12B C11B H11B 109.4 . . ?
C10B C11B H11B 109.4 . . ?
H11A C11B H11B 108.0 . . ?
C12A C13A C17A 111.92(10) . . ?
C12A C13A C19A 109.92(10) . . ?
C17A C13A C19A 105.94(10) . . ?
C12A C13A C14A 115.08(10) . . ?
C17A C13A C14A 103.02(10) . . ?
C19A C13A C14A 110.42(10) . . ?
C17A C16A C15A 104.59(10) . . ?
C17A C16A H16A 110.8 . . ?
C15A C16A H16A 110.8 . . ?
C17A C16A H16B 110.8 . . ?
C15A C16A H16B 110.8 . . ?
H16A C16A H16B 108.9 . . ?
C14B C9B C8B 109.45(10) . . ?
C14B C9B C10B 113.17(9) . . ?
C8B C9B C10B 110.74(9) . . ?
C14B C9B H9B 107.8 . . ?
C8B C9B H9B 107.8 . . ?
C10B C9B H9B 107.8 . . ?
C16B C15B C14B 104.82(11) . . ?
C16B C15B H15A 110.8 . . ?
C14B C15B H15A 110.8 . . ?
C16B C15B H15B 110.8 . . ?
C14B C15B H15B 110.8 . . ?
H15A C15B H15B 108.9 . . ?
C16A C15A C14A 104.22(10) . . ?
C16A C15A H15C 110.9 . . ?
C14A C15A H15C 110.9 . . ?
C16A C15A H15D 110.9 . . ?
C14A C15A H15D 110.9 . . ?
H15C C15A H15D 108.9 . . ?
C3B C4B C5B 112.67(10) . . ?
C3B C4B H4B1 109.1 . . ?
C5B C4B H4B1 109.1 . . ?
C3B C4B H4B2 109.1 . . ?
C5B C4B H4B2 109.1 . . ?
H4B1 C4B H4B2 107.8 . . ?
C3A C4A C5A 113.42(11) . . ?
C3A C4A H41A 108.9 . . ?
C5A C4A H41A 108.9 . . ?
C3A C4A H4A2 108.9 . . ?
C5A C4A H4A2 108.9 . . ?
H41A C4A H4A2 107.7 . . ?
C13B C19B H19A 109.5 . . ?
C13B C19B H19B 109.5 . . ?
H19A C19B H19B 109.5 . . ?
C13B C19B H19C 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
O2B C17B C16B 126.27(12) . . ?
O2B C17B C13B 125.33(12) . . ?
C16B C17B C13B 108.39(11) . . ?
C7B C8B C9B 112.68(10) . . ?
C7B C8B H8B1 109.1 . . ?
C9B C8B H8B1 109.1 . . ?
C7B C8B H8B2 109.1 . . ?
C9B C8B H8B2 109.1 . . ?
H8B1 C8B H8B2 107.8 . . ?
C6A C1A C2A 112.49(10) . . ?
C6A C1A Cl1A 111.00(9) . . ?
C2A C1A Cl1A 107.53(9) . . ?
C6A C1A H4AO 108.6 . . ?
C2A C1A H4AO 108.6 . . ?
Cl1A C1A H4AO 108.6 . . ?
C18A C5A C4A 109.03(10) . . ?
C18A C5A C10A 110.86(10) . . ?
C4A C5A C10A 109.22(10) . . ?
C18A C5A C6A 112.58(10) . . ?
C4A C5A C6A 107.69(10) . . ?
C10A C5A C6A 107.36(9) . . ?
C6B C1B C2B 113.02(10) . . ?
C6B C1B Cl1B 110.30(8) . . ?
C2B C1B Cl1B 108.09(8) . . ?
C6B C1B H1B 108.4 . . ?
C2B C1B H1B 108.4 . . ?
Cl1B C1B H1B 108.4 . . ?
C12A C11A C10A 110.00(10) . . ?
C12A C11A H11C 109.7 . . ?
C10A C11A H11C 109.7 . . ?
C12A C11A H11D 109.7 . . ?
C10A C11A H11D 109.7 . . ?
H11C C11A H11D 108.2 . . ?
C11B C10B C9B 109.61(9) . . ?
C11B C10B C5B 113.60(10) . . ?
C9B C10B C5B 112.90(9) . . ?
C11B C10B H10B 106.8 . . ?
C9B C10B H10B 106.8 . . ?
C5B C10B H10B 106.8 . . ?
C7A C8A C9A 113.07(10) . . ?
C7A C8A H8A1 109.0 . . ?
C9A C8A H8A1 109.0 . . ?
C7A C8A H8A2 109.0 . . ?
C9A C8A H8A2 109.0 . . ?
H8A1 C8A H8A2 107.8 . . ?
C9A C14A C15A 110.24(10) . . ?
C9A C14A C13A 115.29(10) . . ?
C15A C14A C13A 103.05(10) . . ?
C9A C14A H14A 109.3 . . ?
C15A C14A H14A 109.3 . . ?
C13A C14A H14A 109.3 . . ?
O1A C2A C3A 106.53(11) . . ?
O1A C2A C1A 112.35(11) . . ?
C3A C2A C1A 108.42(11) . . ?
O1A C2A H2A 109.8 . . ?
C3A C2A H2A 109.8 . . ?
C1A C2A H2A 109.8 . . ?
C8B C7B C6B 110.42(10) . . ?
C8B C7B H7B1 109.6 . . ?
C6B C7B H7B1 109.6 . . ?
C8B C7B H7B2 109.6 . . ?
C6B C7B H7B2 109.6 . . ?
H7B1 C7B H7B2 108.1 . . ?
C4B C3B C2B 111.90(10) . . ?
C4B C3B H3B1 109.2 . . ?
C2B C3B H3B1 109.2 . . ?
C4B C3B H3B2 109.2 . . ?
C2B C3B H3B2 109.2 . . ?
H3B1 C3B H3B2 107.9 . . ?
C11A C12A C13A 111.82(10) . . ?
C11A C12A H12C 109.3 . . ?
C13A C12A H12C 109.3 . . ?
C11A C12A H12D 109.3 . . ?
C13A C12A H12D 109.3 . . ?
H12C C12A H12D 107.9 . . ?
C2A C3A C4A 111.14(10) . . ?
C2A C3A H3A1 109.4 . . ?
C4A C3A H3A1 109.4 . . ?
C2A C3A H3A2 109.4 . . ?
C4A C3A H3A2 109.4 . . ?
H3A1 C3A H3A2 108.0 . . ?
C8A C7A C6A 110.37(10) . . ?
C8A C7A H7A1 109.6 . . ?
C6A C7A H7A1 109.6 . . ?
C8A C7A H7A2 109.6 . . ?
C6A C7A H7A2 109.6 . . ?
H7A1 C7A H7A2 108.1 . . ?
C13A C19A H19D 109.5 . . ?
C13A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C13A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C5A C18A H18A 109.5 . . ?
C5A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C5A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17B C16B C15B 105.81(10) . . ?
C17B C16B H16C 110.6 . . ?
C15B C16B H16C 110.6 . . ?
C17B C16B H16D 110.6 . . ?
C15B C16B H16D 110.6 . . ?
H16C C16B H16D 108.7 . . ?
C5B C18B H18D 109.5 . . ?
C5B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C5B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 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
_geom_hbond_publ_flag
C2B H2B Cl1B 1.00 2.90 3.6794(12) 135.9 4_466 yes
C16A H16B Cl1A 0.99 2.86 3.5575(13) 127.8 3_546 yes
C3B H3B1 Cl1A 0.99 2.88 3.7070(14) 141.1 . yes
O1B H1BO O2A 0.80(2) 2.09(2) 2.8805(14) 169(2) 3_656 yes
O1A H1AO O1B 0.84(2) 2.05(2) 2.8245(14) 155(2) . yes

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_sad_a
_database_code_depnum_ccdc_archive 'CCDC 1825768'
_audit_update_record             
;
2018-02-26 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H45 Cl O2 Si'
_chemical_formula_sum            'C26 H45 Cl O2 Si'
_chemical_formula_weight         453.16

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   13.2696(16)
_cell_length_b                   7.0208(8)
_cell_length_c                   28.171(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.170(2)
_cell_angle_gamma                90
_cell_volume                     2604.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      3.095
_cell_measurement_theta_max      32.106

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .5500
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2015)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24646
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.089
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6247
_reflns_number_gt                6013
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+6.2520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6247
_refine_ls_number_parameters     278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_restrained_S_all      1.275
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.51636(9) 0.08841(17) 0.21072(4) 0.0285(3) Uani 1 1 d . . . . .
Si1 Si 0.60629(8) 0.60481(17) 0.09645(3) 0.0154(2) Uani 1 1 d . . . . .
O2 O 0.6200(2) 0.5528(4) 0.15407(10) 0.0201(7) Uani 1 1 d . . . . .
O1 O 0.8220(2) 0.5534(5) 0.49515(10) 0.0256(7) Uani 1 1 d . . . . .
C2 C 0.5477(3) 0.4426(6) 0.17606(14) 0.0162(8) Uani 1 1 d . . . . .
H2 H 0.492995 0.396118 0.151124 0.019 Uiso 1 1 calc R U . . .
C14 C 0.8882(3) 0.4468(6) 0.37264(14) 0.0183(8) Uani 1 1 d . . . . .
H14 H 0.938056 0.501786 0.352583 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6065(3) 0.2736(6) 0.19967(14) 0.0173(8) Uani 1 1 d . . . . .
H1 H 0.648691 0.221312 0.175654 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7419(3) 0.1631(6) 0.26652(15) 0.0200(8) Uani 1 1 d . . . . .
H7A H 0.768566 0.086209 0.241406 0.024 Uiso 1 1 calc R U . . .
H7B H 0.698193 0.080214 0.283728 0.024 Uiso 1 1 calc R U . . .
C20 C 0.5594(3) 0.3502(6) 0.30876(14) 0.0180(8) Uani 1 1 d . . . . .
H20A H 0.592890 0.239677 0.325085 0.027 Uiso 1 1 calc R U . . .
H20B H 0.501458 0.307415 0.286300 0.027 Uiso 1 1 calc R U . . .
H20C H 0.535497 0.435945 0.332438 0.027 Uiso 1 1 calc R U . . .
C25 C 0.7101(4) 0.8436(7) 0.03856(17) 0.0291(10) Uani 1 1 d . . . . .
H25A H 0.771820 0.915258 0.034499 0.044 Uiso 1 1 calc R U . . .
H25B H 0.651667 0.930064 0.035196 0.044 Uiso 1 1 calc R U . . .
H25C H 0.699563 0.743737 0.014143 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7272(3) 0.5314(6) 0.31645(13) 0.0158(8) Uani 1 1 d . . . . .
H10 H 0.770233 0.609879 0.297247 0.019 Uiso 1 1 calc R U . . .
C13 C 0.8622(3) 0.5974(8) 0.40937(13) 0.0205(8) Uani 1 1 d . . . . .
C12 C 0.7861(3) 0.7458(6) 0.38698(14) 0.0205(8) Uani 1 1 d . . . . .
H12A H 0.761334 0.820924 0.412930 0.025 Uiso 1 1 calc R U . . .
H12B H 0.821748 0.834428 0.367395 0.025 Uiso 1 1 calc R U . . .
C17 C 0.9404(3) 0.2879(7) 0.40510(14) 0.0205(9) Uani 1 1 d . . . . .
H17A H 0.939652 0.165191 0.387742 0.025 Uiso 1 1 calc R U . . .
H17B H 1.011518 0.322148 0.416802 0.025 Uiso 1 1 calc R U . . .
C24 C 0.8162(3) 0.6256(8) 0.09422(18) 0.0293(11) Uani 1 1 d . . . . .
H24A H 0.876397 0.703687 0.091410 0.044 Uiso 1 1 calc R U . . .
H24B H 0.809686 0.527833 0.069204 0.044 Uiso 1 1 calc R U . . .
H24C H 0.823130 0.564349 0.125716 0.044 Uiso 1 1 calc R U . . .
C16 C 0.8753(3) 0.2765(7) 0.44685(14) 0.0225(9) Uani 1 1 d . . . . .
H16A H 0.823878 0.174249 0.441152 0.027 Uiso 1 1 calc R U . . .
H16B H 0.918581 0.250833 0.477425 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5817(3) 0.6250(6) 0.25374(13) 0.0171(8) Uani 1 1 d . . . . .
H4A H 0.548377 0.703840 0.276408 0.020 Uiso 1 1 calc R U . . .
H4B H 0.633174 0.705221 0.240770 0.020 Uiso 1 1 calc R U . . .
C18 C 0.7275(4) 0.4945(7) 0.46749(15) 0.0253(10) Uani 1 1 d . . . . .
H18A H 0.680670 0.595307 0.453594 0.030 Uiso 1 1 calc R U . . .
H18B H 0.694019 0.378335 0.477813 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7951(3) 0.3708(6) 0.33987(14) 0.0157(8) Uani 1 1 d . . . . .
H9 H 0.753504 0.293230 0.359970 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6356(3) 0.4568(6) 0.28113(13) 0.0144(7) Uani 1 1 d . . . . .
C6 C 0.6797(3) 0.3292(6) 0.24363(14) 0.0162(8) Uani 1 1 d . . . . .
H6 H 0.730986 0.412235 0.230598 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8298(3) 0.2392(6) 0.30140(14) 0.0192(8) Uani 1 1 d . . . . .
H8A H 0.876911 0.310254 0.283252 0.023 Uiso 1 1 calc R U . . .
H8B H 0.867679 0.130370 0.317284 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5017(3) 0.5640(6) 0.21243(14) 0.0170(8) Uani 1 1 d . . . . .
H3A H 0.447493 0.490828 0.225414 0.020 Uiso 1 1 calc R U . . .
H3B H 0.470358 0.678781 0.196384 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6946(3) 0.6614(6) 0.35555(14) 0.0203(8) Uani 1 1 d . . . . .
H11A H 0.652031 0.766042 0.340447 0.024 Uiso 1 1 calc R U . . .
H11B H 0.652917 0.587367 0.375817 0.024 Uiso 1 1 calc R U . . .
C23 C 0.7215(3) 0.7523(7) 0.08849(15) 0.0193(8) Uani 1 1 d . . . . .
C21 C 0.6005(4) 0.3827(7) 0.05990(17) 0.0289(10) Uani 1 1 d . . . . .
H21A H 0.662640 0.308393 0.068486 0.043 Uiso 1 1 calc R U . . .
H21B H 0.594324 0.415930 0.025876 0.043 Uiso 1 1 calc R U . . .
H21C H 0.541520 0.306961 0.066138 0.043 Uiso 1 1 calc R U . . .
C15 C 0.8241(3) 0.4718(7) 0.44810(14) 0.0204(9) Uani 1 1 d . . . . .
C19 C 0.9587(4) 0.7023(7) 0.43189(16) 0.0277(10) Uani 1 1 d . . . . .
H19A H 0.991178 0.764847 0.406657 0.042 Uiso 1 1 calc R U . . .
H19B H 1.005936 0.610514 0.448758 0.042 Uiso 1 1 calc R U . . .
H19C H 0.940177 0.798263 0.454547 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4872(4) 0.7434(9) 0.08080(19) 0.0339(12) Uani 1 1 d . . . . .
H22A H 0.429281 0.668860 0.088886 0.051 Uiso 1 1 calc R U . . .
H22B H 0.478213 0.771195 0.046445 0.051 Uiso 1 1 calc R U . . .
H22C H 0.491461 0.863080 0.098842 0.051 Uiso 1 1 calc R U . . .
C26 C 0.7332(4) 0.9087(8) 0.12672(18) 0.0336(12) Uani 1 1 d . . . . .
H26A H 0.748067 0.850568 0.158441 0.050 Uiso 1 1 calc R U . . .
H26B H 0.670082 0.982100 0.125147 0.050 Uiso 1 1 calc R U . . .
H26C H 0.789115 0.993621 0.121004 0.050 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 C1 1.820(4) . ?
Si1 O2 1.652(3) . ?
Si1 C22 1.861(5) . ?
Si1 C21 1.865(5) . ?
Si1 C23 1.882(4) . ?
O2 C2 1.432(5) . ?
O1 C15 1.447(5) . ?
O1 C18 1.450(6) . ?
C2 C3 1.518(5) . ?
C2 C1 1.526(6) . ?
C2 H2 1.0000 . ?
C14 C9 1.542(6) . ?
C14 C13 1.548(6) . ?
C14 C17 1.550(6) . ?
C14 H14 1.0000 . ?
C1 C6 1.526(6) . ?
C1 H1 1.0000 . ?
C7 C6 1.524(6) . ?
C7 C8 1.526(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C20 C5 1.544(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C25 C23 1.536(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C10 C11 1.534(5) . ?
C10 C9 1.539(5) . ?
C10 C5 1.562(5) . ?
C10 H10 1.0000 . ?
C13 C12 1.531(6) . ?
C13 C15 1.537(6) . ?
C13 C19 1.543(6) . ?
C12 C11 1.530(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C17 C16 1.545(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C24 C23 1.532(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C16 C15 1.533(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C4 C3 1.535(5) . ?
C4 C5 1.537(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C18 C15 1.463(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C9 C8 1.538(5) . ?
C9 H9 1.0000 . ?
C5 C6 1.555(5) . ?
C6 H6 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C23 C26 1.533(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
O2 Si1 C22 109.53(19) . . ?
O2 Si1 C21 110.5(2) . . ?
C22 Si1 C21 109.3(3) . . ?
O2 Si1 C23 104.33(17) . . ?
C22 Si1 C23 111.2(2) . . ?
C21 Si1 C23 111.9(2) . . ?
C2 O2 Si1 123.2(3) . . ?
C15 O1 C18 60.6(3) . . ?
O2 C2 C3 109.6(3) . . ?
O2 C2 C1 106.0(3) . . ?
C3 C2 C1 111.7(3) . . ?
O2 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C9 C14 C13 114.1(3) . . ?
C9 C14 C17 111.7(3) . . ?
C13 C14 C17 102.6(3) . . ?
C9 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C17 C14 H14 109.4 . . ?
C2 C1 C6 113.2(3) . . ?
C2 C1 Cl1 108.6(3) . . ?
C6 C1 Cl1 114.2(3) . . ?
C2 C1 H1 106.8 . . ?
C6 C1 H1 106.8 . . ?
Cl1 C1 H1 106.8 . . ?
C6 C7 C8 109.6(3) . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C5 C20 H20A 109.5 . . ?
C5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C11 C10 C9 109.3(3) . . ?
C11 C10 C5 113.0(3) . . ?
C9 C10 C5 113.3(3) . . ?
C11 C10 H10 107.0 . . ?
C9 C10 H10 107.0 . . ?
C5 C10 H10 107.0 . . ?
C12 C13 C15 115.1(3) . . ?
C12 C13 C19 108.4(4) . . ?
C15 C13 C19 108.2(3) . . ?
C12 C13 C14 112.3(3) . . ?
C15 C13 C14 101.7(4) . . ?
C19 C13 C14 111.0(4) . . ?
C11 C12 C13 114.2(4) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C16 C17 C14 103.6(3) . . ?
C16 C17 H17A 111.0 . . ?
C14 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C14 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C16 C17 105.2(3) . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C3 C4 C5 113.6(3) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O1 C18 C15 59.6(3) . . ?
O1 C18 H18A 117.8 . . ?
C15 C18 H18A 117.8 . . ?
O1 C18 H18B 117.8 . . ?
C15 C18 H18B 117.8 . . ?
H18A C18 H18B 115.0 . . ?
C8 C9 C10 110.4(3) . . ?
C8 C9 C14 110.0(3) . . ?
C10 C9 C14 112.7(3) . . ?
C8 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
C14 C9 H9 107.9 . . ?
C4 C5 C20 109.4(3) . . ?
C4 C5 C6 107.0(3) . . ?
C20 C5 C6 112.9(3) . . ?
C4 C5 C10 109.8(3) . . ?
C20 C5 C10 110.3(3) . . ?
C6 C5 C10 107.3(3) . . ?
C7 C6 C1 113.8(3) . . ?
C7 C6 C5 112.6(3) . . ?
C1 C6 C5 116.3(3) . . ?
C7 C6 H6 104.2 . . ?
C1 C6 H6 104.2 . . ?
C5 C6 H6 104.2 . . ?
C7 C8 C9 113.1(3) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C2 C3 C4 111.7(3) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C12 C11 C10 111.8(3) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C24 C23 C26 109.4(4) . . ?
C24 C23 C25 108.9(4) . . ?
C26 C23 C25 109.5(4) . . ?
C24 C23 Si1 109.6(3) . . ?
C26 C23 Si1 108.9(3) . . ?
C25 C23 Si1 110.5(3) . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C15 C18 59.8(3) . . ?
O1 C15 C16 115.7(3) . . ?
C18 C15 C16 121.2(4) . . ?
O1 C15 C13 118.0(4) . . ?
C18 C15 C13 125.7(4) . . ?
C16 C15 C13 108.1(4) . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1586620'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H29 Cl O2'
_chemical_formula_sum            'C19 H29 Cl O2'
_chemical_formula_weight         324.87

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1254(5)
_cell_length_b                   11.6665(8)
_cell_length_c                   10.8645(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.497(2)
_cell_angle_gamma                90
_cell_volume                     878.21(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8737
_cell_measurement_theta_min      2.601
_cell_measurement_theta_max      32.330

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .6455
_exptl_absorpt_correction_T_max  .7465
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22481
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         33.232
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6706
_reflns_number_gt                5767
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.3261P] 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_abs_structure_details 
;
 Flack x determined using 2340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6706
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.49093(7) 0.64907(4) 0.32842(5) 0.02033(11) Uani 1 1 d . . . . .
O1 O 0.0388(3) 0.51192(18) 0.09026(16) 0.0276(4) Uani 1 1 d . . . . .
O2 O 0.3217(3) 0.44333(17) 0.95594(16) 0.0288(4) Uani 1 1 d . . . . .
C5 C 0.1670(3) 0.45282(17) 0.42161(18) 0.0135(3) Uani 1 1 d . . . . .
C9 C 0.4606(3) 0.46004(17) 0.61376(17) 0.0115(3) Uani 1 1 d . . . . .
H9 H 0.426074 0.385591 0.648419 0.014 Uiso 1 1 calc R U . . .
C10 C 0.2702(3) 0.51862(17) 0.54411(17) 0.0121(3) Uani 1 1 d . . . . .
H10 H 0.303661 0.596739 0.517914 0.014 Uiso 1 1 calc R U . . .
C1 C 0.3360(3) 0.53337(18) 0.24904(18) 0.0156(4) Uani 1 1 d . . . . .
H1 H 0.398033 0.501911 0.182597 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5948(3) 0.43341(18) 0.52599(18) 0.0153(4) Uani 1 1 d . . . . .
H8A H 0.653691 0.505895 0.506172 0.018 Uiso 1 1 calc R U . . .
H8B H 0.700356 0.383242 0.571602 0.018 Uiso 1 1 calc R U . . .
C14 C 0.5711(3) 0.53262(17) 0.72642(17) 0.0141(3) Uani 1 1 d . . . . .
H14 H 0.629906 0.600877 0.694264 0.017 Uiso 1 1 calc R U . . .
C6 C 0.3069(3) 0.43265(17) 0.33281(18) 0.0134(3) Uani 1 1 d . . . . .
H6 H 0.240850 0.373118 0.271622 0.016 Uiso 1 1 calc R U . . .
C12 C 0.2418(3) 0.61259(19) 0.7484(2) 0.0190(4) Uani 1 1 d . . . . .
H12A H 0.250971 0.690719 0.714727 0.023 Uiso 1 1 calc R U . . .
H12B H 0.160618 0.616972 0.810813 0.023 Uiso 1 1 calc R U . . .
C17 C 0.4446(3) 0.46744(18) 0.89942(18) 0.0189(4) Uani 1 1 d . . . . .
C11 C 0.1439(3) 0.53419(19) 0.64002(19) 0.0167(4) Uani 1 1 d . . . . .
H11A H 0.017965 0.567441 0.596673 0.020 Uiso 1 1 calc R U . . .
H11B H 0.119460 0.458493 0.674416 0.020 Uiso 1 1 calc R U . . .
C13 C 0.4437(3) 0.57204(18) 0.81544(19) 0.0169(4) Uani 1 1 d . . . . .
C16 C 0.6270(3) 0.39910(19) 0.9045(2) 0.0199(4) Uani 1 1 d . . . . .
H16A H 0.595324 0.319354 0.875923 0.024 Uiso 1 1 calc R U . . .
H16B H 0.708583 0.397421 0.991767 0.024 Uiso 1 1 calc R U . . .
C2 C 0.1464(3) 0.5904(2) 0.1798(2) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.174837 0.661122 0.135445 0.024 Uiso 1 1 calc R U . . .
C19 C 0.0986(3) 0.3337(2) 0.4565(2) 0.0197(4) Uani 1 1 d . . . . .
H19A H -0.009566 0.343257 0.497113 0.029 Uiso 1 1 calc R U . . .
H19B H 0.205244 0.294833 0.514935 0.029 Uiso 1 1 calc R U . . .
H19C H 0.057021 0.287607 0.379544 0.029 Uiso 1 1 calc R U . . .
C4 C -0.0139(3) 0.5153(2) 0.3462(2) 0.0191(4) Uani 1 1 d . . . . .
H4A H -0.091219 0.460494 0.285279 0.023 Uiso 1 1 calc R U . . .
H4B H -0.093062 0.538593 0.405657 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7313(3) 0.4610(2) 0.81507(19) 0.0196(4) Uani 1 1 d . . . . .
H15A H 0.788995 0.405297 0.765868 0.024 Uiso 1 1 calc R U . . .
H15B H 0.834581 0.511431 0.863125 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4956(3) 0.37529(19) 0.40208(19) 0.0161(4) Uani 1 1 d . . . . .
H7A H 0.468080 0.294636 0.420087 0.019 Uiso 1 1 calc R U . . .
H7B H 0.585839 0.374537 0.345217 0.019 Uiso 1 1 calc R U . . .
C18 C 0.5457(4) 0.6664(2) 0.9067(2) 0.0291(5) Uani 1 1 d . . . . .
H18A H 0.462540 0.689861 0.962386 0.044 Uiso 1 1 calc R U . . .
H18B H 0.571643 0.732633 0.857651 0.044 Uiso 1 1 calc R U . . .
H18C H 0.667782 0.636599 0.957828 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0249(3) 0.6209(2) 0.2735(2) 0.0214(4) Uani 1 1 d . . . . .
H3A H 0.093440 0.679107 0.333868 0.026 Uiso 1 1 calc R U . . .
H3B H -0.099319 0.654351 0.227338 0.026 Uiso 1 1 calc R U . . .
H1O H 0.108(5) 0.498(3) 0.045(4) 0.037(9) Uiso 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
Cl1 C1 1.828(2) . ?
O1 C2 1.422(3) . ?
O1 H1O 0.79(4) . ?
O2 C17 1.214(3) . ?
C5 C4 1.540(3) . ?
C5 C19 1.549(3) . ?
C5 C6 1.559(3) . ?
C5 C10 1.564(3) . ?
C9 C8 1.531(3) . ?
C9 C10 1.550(3) . ?
C9 C14 1.544(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.538(3) . ?
C10 H10 1.0000 . ?
C1 C6 1.530(3) . ?
C1 C2 1.536(3) . ?
C1 H1 1.0000 . ?
C8 C7 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C14 C13 1.543(3) . ?
C14 C15 1.554(3) . ?
C14 H14 1.0000 . ?
C6 C7 1.533(3) . ?
C6 H6 1.0000 . ?
C12 C13 1.528(3) . ?
C12 C11 1.525(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C17 C16 1.515(3) . ?
C17 C13 1.523(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C18 1.545(3) . ?
C16 C15 1.535(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C2 C3 1.525(3) . ?
C2 H2 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 C3 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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 O1 H1O 104(3) . . ?
C4 C5 C19 106.46(17) . . ?
C4 C5 C6 108.60(15) . . ?
C19 C5 C6 107.41(16) . . ?
C4 C5 C10 112.94(16) . . ?
C19 C5 C10 110.16(16) . . ?
C6 C5 C10 111.04(15) . . ?
C8 C9 C10 112.83(15) . . ?
C8 C9 C14 109.14(15) . . ?
C10 C9 C14 111.81(16) . . ?
C8 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
C14 C9 H9 107.6 . . ?
C11 C10 C9 107.77(15) . . ?
C11 C10 C5 113.64(16) . . ?
C9 C10 C5 112.55(15) . . ?
C11 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C5 C10 H10 107.5 . . ?
C6 C1 C2 113.47(17) . . ?
C6 C1 Cl1 115.93(13) . . ?
C2 C1 Cl1 106.07(15) . . ?
C6 C1 H1 107.0 . . ?
C2 C1 H1 107.0 . . ?
Cl1 C1 H1 107.0 . . ?
C7 C8 C9 114.33(16) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C13 C14 C9 113.24(16) . . ?
C13 C14 C15 103.07(15) . . ?
C9 C14 C15 111.19(17) . . ?
C13 C14 H14 109.7 . . ?
C9 C14 H14 109.7 . . ?
C15 C14 H14 109.7 . . ?
C7 C6 C1 113.73(16) . . ?
C7 C6 C5 112.13(15) . . ?
C1 C6 C5 116.57(17) . . ?
C7 C6 H6 104.2 . . ?
C1 C6 H6 104.2 . . ?
C5 C6 H6 104.2 . . ?
C13 C12 C11 113.11(17) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O2 C17 C16 125.0(2) . . ?
O2 C17 C13 125.9(2) . . ?
C16 C17 C13 109.08(19) . . ?
C12 C11 C10 111.05(17) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C17 C13 C12 113.90(19) . . ?
C17 C13 C18 104.55(17) . . ?
C12 C13 C18 109.57(18) . . ?
C17 C13 C14 102.49(17) . . ?
C12 C13 C14 114.81(16) . . ?
C18 C13 C14 110.92(19) . . ?
C17 C16 C15 105.51(17) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
O1 C2 C3 107.90(18) . . ?
O1 C2 C1 109.19(19) . . ?
C3 C2 C1 110.21(17) . . ?
O1 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 C5 115.37(17) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C16 C15 C14 104.53(17) . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C8 C7 C6 114.30(16) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C3 C2 110.93(19) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?

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
_geom_hbond_publ_flag
O1 H1O O2 0.79(4) 2.08(4) 2.865(3) 169(4) 1_554 yes
C16 H16A Cl1 0.99 2.94 3.824(2) 149.9 2_646 yes
C1 H1 O2 1.00 2.49 3.332(3) 141.6 1_554 yes
O1 H1O O2 0.79(4) 2.08(4) 2.865(3) 169(4) 1_554 yes
C16 H16A Cl1 0.99 2.94 3.824(2) 149.9 2_646 yes
C1 H1 O2 1.00 2.49 3.332(3) 141.6 1_554 yes
C1 H1 O2 1.00 2.49 3.332(3) 141.6 1_554 yes
C16 H16A Cl1 0.99 2.94 3.824(2) 149.9 2_646 yes
O1 H1O O2 0.79(4) 2.08(4) 2.865(3) 169(4) 1_554 yes

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: heptane/diisopropylether'
####################################################################### 
# 
# 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_23
_database_code_depnum_ccdc_archive 'CCDC 1586621'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H27 Cl O2'
_chemical_formula_sum            'C19 H27 Cl O2'
_chemical_formula_weight         322.85

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'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.4333(17)
_cell_length_b                   13.538(3)
_cell_length_c                   16.411(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1651.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8379
_cell_measurement_theta_min      2.982
_cell_measurement_theta_max      34.957

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33711
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.482
_diffrn_reflns_theta_max         34.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7201
_reflns_number_gt                6793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.1722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.038(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7201
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_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 1.09140(3) 0.13019(2) 0.72605(2) 0.01585(6) Uani 1 1 d . . . . .
O2 O 0.36409(12) 0.65926(7) 0.58785(6) 0.01760(17) Uani 1 1 d . . . . .
O1 O 0.78357(13) 0.00190(7) 0.71912(7) 0.02152(19) Uani 1 1 d . . . . .
C10 C 0.62401(13) 0.37020(8) 0.58482(6) 0.00973(16) Uani 1 1 d . . . . .
H10 H 0.658627 0.335445 0.533384 0.012 Uiso 1 1 calc R U . . .
C9 C 0.75520(14) 0.45848(8) 0.59500(6) 0.00988(16) Uani 1 1 d . . . . .
H9 H 0.717931 0.496312 0.644540 0.012 Uiso 1 1 calc R U . . .
C6 C 0.83920(14) 0.25856(8) 0.66191(6) 0.00976(17) Uani 1 1 d . . . . .
H6 H 0.872854 0.230043 0.607809 0.012 Uiso 1 1 calc R U . . .
C8 C 0.94956(14) 0.42242(8) 0.60819(7) 0.01206(18) Uani 1 1 d . . . . .
H8A H 0.994332 0.392425 0.557048 0.014 Uiso 1 1 calc R U . . .
H8B H 1.027013 0.479878 0.620927 0.014 Uiso 1 1 calc R U . . .
C5 C 0.63826(14) 0.29230(8) 0.65574(6) 0.00939(16) Uani 1 1 d . . . . .
C12 C 0.41855(16) 0.47485(8) 0.49595(6) 0.01299(18) Uani 1 1 d . . . . .
H12A H 0.439405 0.433419 0.447146 0.016 Uiso 1 1 calc R U . . .
H12B H 0.295448 0.502353 0.492045 0.016 Uiso 1 1 calc R U . . .
C4 C 0.52605(15) 0.19996(8) 0.63287(7) 0.01336(19) Uani 1 1 d . . . . .
H4A H 0.398102 0.219239 0.627626 0.016 Uiso 1 1 calc R U . . .
H4B H 0.566694 0.175097 0.579207 0.016 Uiso 1 1 calc R U . . .
C17 C 0.51185(15) 0.64083(8) 0.55874(6) 0.01212(18) Uani 1 1 d . . . . .
C13 C 0.55379(14) 0.55978(8) 0.49618(6) 0.01127(17) Uani 1 1 d . . . . .
C19 C 0.56945(16) 0.33658(8) 0.73748(7) 0.01400(19) Uani 1 1 d . . . . .
H19A H 0.439286 0.347356 0.734115 0.021 Uiso 1 1 calc R U . . .
H19B H 0.629982 0.399672 0.747763 0.021 Uiso 1 1 calc R U . . .
H19C H 0.595723 0.290618 0.782053 0.021 Uiso 1 1 calc R U . . .
C2 C 0.73494(15) 0.08755(8) 0.71359(6) 0.01266(18) Uani 1 1 d . . . . .
C7 C 0.96526(15) 0.34627(8) 0.67749(7) 0.01230(18) Uani 1 1 d . . . . .
H7A H 1.090930 0.322485 0.681209 0.015 Uiso 1 1 calc R U . . .
H7B H 0.933669 0.377908 0.729961 0.015 Uiso 1 1 calc R U . . .
C11 C 0.43126(14) 0.40950(8) 0.57259(7) 0.01230(18) Uani 1 1 d . . . . .
H11A H 0.347204 0.353136 0.567276 0.015 Uiso 1 1 calc R U . . .
H11B H 0.395038 0.448424 0.620948 0.015 Uiso 1 1 calc R U . . .
C16 C 0.68654(16) 0.69513(9) 0.57880(8) 0.0156(2) Uani 1 1 d . . . . .
H16A H 0.702599 0.700851 0.638503 0.019 Uiso 1 1 calc R U . . .
H16B H 0.686174 0.762232 0.554811 0.019 Uiso 1 1 calc R U . . .
C14 C 0.74798(14) 0.53000(8) 0.52078(6) 0.01157(17) Uani 1 1 d . . . . .
H14 H 0.810195 0.499093 0.473146 0.014 Uiso 1 1 calc R U . . .
C3 C 0.54186(15) 0.11612(8) 0.69618(7) 0.01476(19) Uani 1 1 d . . . . .
H3A H 0.483934 0.137430 0.747576 0.018 Uiso 1 1 calc R U . . .
H3B H 0.476177 0.057447 0.675894 0.018 Uiso 1 1 calc R U . . .
C15 C 0.83788(15) 0.63148(9) 0.54094(7) 0.01537(19) Uani 1 1 d . . . . .
H15A H 0.938032 0.622708 0.580040 0.018 Uiso 1 1 calc R U . . .
H15B H 0.885253 0.662842 0.490846 0.018 Uiso 1 1 calc R U . . .
C1 C 0.86298(14) 0.17544(8) 0.72605(7) 0.01143(17) Uani 1 1 d . . . . .
H1 H 0.837984 0.204297 0.780992 0.014 Uiso 1 1 calc R U . . .
C18 C 0.55465(17) 0.61182(9) 0.41132(7) 0.0163(2) Uani 1 1 d . . . . .
H18A H 0.430994 0.628059 0.395533 0.024 Uiso 1 1 calc R U . . .
H18B H 0.607537 0.567508 0.370630 0.024 Uiso 1 1 calc R U . . .
H18C H 0.625975 0.672583 0.414523 0.024 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 C1 1.8051(11) . ?
O2 C17 1.2235(14) . ?
O1 C2 1.2179(14) . ?
C10 C11 1.5415(14) . ?
C10 C9 1.5515(15) . ?
C10 C5 1.5742(14) . ?
C10 H10 1.0000 . ?
C9 C8 1.5402(15) . ?
C9 C14 1.5569(15) . ?
C9 H9 1.0000 . ?
C6 C7 1.5340(15) . ?
C6 C1 1.5509(15) . ?
C6 C5 1.5652(15) . ?
C6 H6 1.0000 . ?
C8 C7 1.5393(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 C4 1.5489(16) . ?
C5 C19 1.5558(15) . ?
C12 C13 1.5272(16) . ?
C12 C11 1.5406(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C4 C3 1.5432(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 C16 1.5281(17) . ?
C17 C13 1.5346(15) . ?
C13 C14 1.5521(16) . ?
C13 C18 1.5607(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C2 C3 1.5136(16) . ?
C2 C1 1.5373(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C16 C15 1.5473(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C14 C15 1.5631(16) . ?
C14 H14 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C1 H1 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 C10 C9 109.41(9) . . ?
C11 C10 C5 112.95(8) . . ?
C9 C10 C5 113.21(8) . . ?
C11 C10 H10 107.0 . . ?
C9 C10 H10 107.0 . . ?
C5 C10 H10 107.0 . . ?
C8 C9 C10 111.14(8) . . ?
C8 C9 C14 109.84(8) . . ?
C10 C9 C14 111.90(8) . . ?
C8 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
C14 C9 H9 107.9 . . ?
C7 C6 C1 112.26(9) . . ?
C7 C6 C5 111.58(8) . . ?
C1 C6 C5 111.37(8) . . ?
C7 C6 H6 107.1 . . ?
C1 C6 H6 107.1 . . ?
C5 C6 H6 107.1 . . ?
C7 C8 C9 112.78(8) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C4 C5 C19 110.05(9) . . ?
C4 C5 C6 107.10(8) . . ?
C19 C5 C6 111.74(8) . . ?
C4 C5 C10 108.98(8) . . ?
C19 C5 C10 110.93(9) . . ?
C6 C5 C10 107.91(8) . . ?
C13 C12 C11 112.95(9) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C3 C4 C5 112.92(9) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
O2 C17 C16 125.49(10) . . ?
O2 C17 C13 126.12(10) . . ?
C16 C17 C13 108.39(9) . . ?
C12 C13 C17 113.97(9) . . ?
C12 C13 C14 114.66(9) . . ?
C17 C13 C14 101.58(8) . . ?
C12 C13 C18 109.90(9) . . ?
C17 C13 C18 105.96(9) . . ?
C14 C13 C18 110.21(9) . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C2 C3 122.60(11) . . ?
O1 C2 C1 122.90(10) . . ?
C3 C2 C1 114.48(9) . . ?
C6 C7 C8 110.42(9) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C12 C11 C10 111.19(8) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C17 C16 C15 105.27(9) . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C13 C14 C9 113.40(8) . . ?
C13 C14 C15 102.96(9) . . ?
C9 C14 C15 111.48(9) . . ?
C13 C14 H14 109.6 . . ?
C9 C14 H14 109.6 . . ?
C15 C14 H14 109.6 . . ?
C2 C3 C4 112.78(9) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C16 C15 C14 105.29(9) . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C2 C1 C6 113.62(9) . . ?
C2 C1 Cl1 108.64(7) . . ?
C6 C1 Cl1 110.70(7) . . ?
C2 C1 H1 107.9 . . ?
C6 C1 H1 107.9 . . ?
Cl1 C1 H1 107.9 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.049

