# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1998324'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-11,13-bis(benzyloxy)-4,5,5,9-tetramethyl-4,5,6,7-tetrahydro-2H-benzo[d][1]oxacyclododecine-2,10(1H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H36 O5'
_chemical_formula_sum            'C33 H36 O5'
_chemical_formula_weight         512.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

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

_cell_length_a                   23.1727(9)
_cell_length_b                   29.8856(16)
_cell_length_c                   8.3703(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5796.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    16314
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      65.85

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'Incoatec microSource Cu'
_diffrn_radiation_monochromator  'X-ray mirror'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 521 frames, detector distance = 40 mm
;
_diffrn_reflns_number            24930
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         68.052
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5222
_reflns_number_gt                2975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED32'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1754P)²+12.4961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5222
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.1103
_refine_ls_wR_factor_ref         0.3518
_refine_ls_wR_factor_gt          0.2688
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.6930(2) 0.40935(17) 0.6910(6) 0.0475(12) Uani 1 1 d . . . . .
C2 C 0.6642(2) 0.41955(18) 0.8461(6) 0.0502(13) Uani 1 1 d . . . . .
H2A H 0.6911 0.4357 0.9173 0.060 Uiso 1 1 calc R U . . .
H2AB H 0.6525 0.3914 0.8995 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6114(2) 0.44822(15) 0.8134(6) 0.0433(11) Uani 1 1 d . . . . .
C4 C 0.6205(2) 0.49015(17) 0.7439(6) 0.0493(13) Uani 1 1 d . . . . .
H4 H 0.6586 0.5004 0.7240 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5735(2) 0.51676(16) 0.7041(7) 0.0497(13) Uani 1 1 d . . . . .
C6 C 0.5174(2) 0.50331(17) 0.7358(7) 0.0512(13) Uani 1 1 d . . . . .
H6 H 0.4856 0.5218 0.7089 0.061 Uiso 1 1 calc R U . . .
C7 C 0.5091(2) 0.46190(16) 0.8082(7) 0.0469(12) Uani 1 1 d . . . . .
C8 C 0.5556(2) 0.43330(16) 0.8454(6) 0.0456(12) Uani 1 1 d . . . . .
C9 C 0.5425(2) 0.38961(16) 0.9256(6) 0.0464(12) Uani 1 1 d . . . . .
C10 C 0.5425(2) 0.34801(16) 0.8333(6) 0.0481(12) Uani 1 1 d . . . . .
C11 C 0.5526(2) 0.34990(17) 0.6724(7) 0.0511(13) Uani 1 1 d . . . . .
H11 H 0.5559 0.3788 0.6260 0.061 Uiso 1 1 calc R U . . .
C12 C 0.5587(3) 0.31093(17) 0.5638(7) 0.0565(14) Uani 1 1 d . . . . .
H12A H 0.5201 0.2977 0.5468 0.068 Uiso 1 1 calc R U . . .
H12B H 0.5828 0.2881 0.6179 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5856(2) 0.32094(18) 0.3990(6) 0.0533(13) Uani 1 1 d . . . . .
H13A H 0.5660 0.3478 0.3561 0.064 Uiso 1 1 calc R U . . .
H13B H 0.5755 0.2957 0.3277 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6514(2) 0.32884(18) 0.3827(7) 0.0537(13) Uani 1 1 d . . . . .
C15 C 0.6725(2) 0.37496(17) 0.4353(6) 0.0492(12) Uani 1 1 d . . . . .
H15 H 0.7151 0.3763 0.4158 0.059 Uiso 1 1 calc R U . . .
O16 O 0.66295(16) 0.37868(12) 0.6077(4) 0.0515(9) Uani 1 1 d . . . . .
O17 O 0.73631(16) 0.42730(13) 0.6392(5) 0.0590(10) Uani 1 1 d . . . . .
O18 O 0.58817(16) 0.55682(11) 0.6331(5) 0.0590(11) Uani 1 1 d . . . . .
C19 C 0.5427(2) 0.58789(17) 0.6008(8) 0.0558(14) Uani 1 1 d . . . . .
H19A H 0.5172 0.5907 0.6951 0.067 Uiso 1 1 calc R U . . .
H19B H 0.5193 0.5774 0.5092 0.067 Uiso 1 1 calc R U . . .
C20 C 0.5699(3) 0.63207(17) 0.5627(7) 0.0560(14) Uani 1 1 d . . . . .
C21 C 0.5962(3) 0.63987(19) 0.4162(8) 0.0661(17) Uani 1 1 d . . . . .
H21 H 0.5974 0.6168 0.3384 0.079 Uiso 1 1 calc R U . . .
C22 C 0.6209(4) 0.6812(2) 0.3827(10) 0.088(2) Uani 1 1 d . . . . .
H22 H 0.6386 0.6865 0.2822 0.106 Uiso 1 1 calc R U . . .
C23 C 0.6193(4) 0.7144(2) 0.4975(11) 0.095(3) Uani 1 1 d . . . . .
H23 H 0.6370 0.7425 0.4764 0.114 Uiso 1 1 calc R U . . .
C24 C 0.5922(4) 0.7074(2) 0.6424(10) 0.082(2) Uani 1 1 d . . . . .
H24 H 0.5897 0.7309 0.7184 0.098 Uiso 1 1 calc R U . . .
C25 C 0.5688(3) 0.66613(19) 0.6762(8) 0.0666(17) Uani 1 1 d . . . . .
H25 H 0.5519 0.6608 0.7778 0.080 Uiso 1 1 calc R U . . .
O26 O 0.45570(14) 0.44428(11) 0.8446(5) 0.0540(10) Uani 1 1 d . . . . .
C27 C 0.4065(2) 0.47291(18) 0.8341(7) 0.0521(13) Uani 1 1 d . . . . .
H27A H 0.3975 0.4793 0.7208 0.062 Uiso 1 1 calc R U . . .
H27B H 0.4144 0.5016 0.8891 0.062 Uiso 1 1 calc R U . . .
C28 C 0.3562(2) 0.44926(19) 0.9125(7) 0.0545(14) Uani 1 1 d . . . . .
C29 C 0.3018(3) 0.4688(2) 0.9045(8) 0.0733(19) Uani 1 1 d . . . . .
H29 H 0.2966 0.4959 0.8469 0.088 Uiso 1 1 calc R U . . .
C30 C 0.2555(3) 0.4490(3) 0.9798(10) 0.094(3) Uani 1 1 d . . . . .
H30 H 0.2184 0.4624 0.9734 0.113 Uiso 1 1 calc R U . . .
C31 C 0.2627(3) 0.4099(3) 1.0642(11) 0.100(3) Uani 1 1 d . . . . .
H31 H 0.2306 0.3960 1.1139 0.120 Uiso 1 1 calc R U . . .
C32 C 0.3163(3) 0.3911(3) 1.0763(10) 0.088(2) Uani 1 1 d . . . . .
H32 H 0.3215 0.3643 1.1359 0.106 Uiso 1 1 calc R U . . .
C33 C 0.3628(3) 0.4109(2) 1.0022(8) 0.0700(18) Uani 1 1 d . . . . .
H33 H 0.4000 0.3979 1.0129 0.084 Uiso 1 1 calc R U . . .
O34 O 0.53527(18) 0.38881(12) 1.0713(4) 0.0580(10) Uani 1 1 d . . . . .
C35 C 0.5320(3) 0.30487(18) 0.9194(8) 0.0646(16) Uani 1 1 d . . . . .
H35A H 0.5177 0.2824 0.8437 0.097 Uiso 1 1 calc R U . . .
H35B H 0.5033 0.3096 1.0037 0.097 Uiso 1 1 calc R U . . .
H35C H 0.5682 0.2943 0.9671 0.097 Uiso 1 1 calc R U . . .
C36 C 0.6658(3) 0.3241(2) 0.2056(7) 0.0597(15) Uani 1 1 d . . . . .
H36A H 0.6396 0.3428 0.1427 0.090 Uiso 1 1 calc R U . . .
H36B H 0.6612 0.2927 0.1734 0.090 Uiso 1 1 calc R U . . .
H36C H 0.7057 0.3335 0.1871 0.090 Uiso 1 1 calc R U . . .
C37 C 0.6862(3) 0.29284(19) 0.4744(8) 0.0644(16) Uani 1 1 d . . . . .
H37A H 0.6715 0.2631 0.4470 0.097 Uiso 1 1 calc R U . . .
H37B H 0.6822 0.2978 0.5896 0.097 Uiso 1 1 calc R U . . .
H37C H 0.7270 0.2949 0.4447 0.097 Uiso 1 1 calc R U . . .
C38 C 0.6451(2) 0.41524(17) 0.3546(7) 0.0550(14) Uani 1 1 d . . . . .
H38A H 0.6530 0.4142 0.2396 0.083 Uiso 1 1 calc R U . . .
H38B H 0.6613 0.4428 0.3998 0.083 Uiso 1 1 calc R U . . .
H38C H 0.6033 0.4147 0.3723 0.083 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
C1 O17 1.218(6) . ?
C1 O16 1.346(6) . ?
C1 C2 1.491(7) . ?
C2 C3 1.517(7) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C8 1.394(7) . ?
C3 C4 1.397(7) . ?
C4 C5 1.390(7) . ?
C4 H4 0.9500 . ?
C5 O18 1.379(6) . ?
C5 C6 1.385(7) . ?
C6 C7 1.391(7) . ?
C6 H6 0.9500 . ?
C7 O26 1.379(6) . ?
C7 C8 1.410(7) . ?
C8 C9 1.499(7) . ?
C9 O34 1.232(6) . ?
C9 C10 1.464(7) . ?
C10 C11 1.368(7) . ?
C10 C35 1.497(7) . ?
C11 C12 1.484(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.543(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.547(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C36 1.526(8) . ?
C14 C15 1.528(7) . ?
C14 C37 1.549(8) . ?
C15 O16 1.465(6) . ?
C15 C38 1.520(7) . ?
C15 H15 1.0000 . ?
O18 C19 1.429(6) . ?
C19 C20 1.497(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.389(8) . ?
C20 C25 1.393(8) . ?
C21 C22 1.389(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(8) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O26 C27 1.427(6) . ?
C27 C28 1.513(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C33 1.380(8) . ?
C28 C29 1.392(8) . ?
C29 C30 1.377(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.377(10) . ?
C30 H30 0.9500 . ?
C31 C32 1.367(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.376(9) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
O17 C1 O16 122.8(5) . . ?
O17 C1 C2 126.1(5) . . ?
O16 C1 C2 111.0(4) . . ?
C1 C2 C3 108.6(4) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2AB 110.0 . . ?
C3 C2 H2AB 110.0 . . ?
H2A C2 H2AB 108.3 . . ?
C8 C3 C4 120.4(4) . . ?
C8 C3 C2 122.2(4) . . ?
C4 C3 C2 117.4(4) . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O18 C5 C6 124.5(5) . . ?
O18 C5 C4 114.0(5) . . ?
C6 C5 C4 121.5(5) . . ?
C5 C6 C7 118.1(5) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
O26 C7 C6 124.1(5) . . ?
O26 C7 C8 113.9(4) . . ?
C6 C7 C8 122.0(5) . . ?
C3 C8 C7 118.2(4) . . ?
C3 C8 C9 123.5(4) . . ?
C7 C8 C9 118.2(4) . . ?
O34 C9 C10 120.4(5) . . ?
O34 C9 C8 119.2(5) . . ?
C10 C9 C8 120.2(4) . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 C35 122.5(5) . . ?
C9 C10 C35 118.5(5) . . ?
C10 C11 C12 126.0(5) . . ?
C10 C11 H11 117.0 . . ?
C12 C11 H11 117.0 . . ?
C11 C12 C13 115.7(5) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 H13A 107.2 . . ?
C14 C13 H13A 107.2 . . ?
C12 C13 H13B 107.2 . . ?
C14 C13 H13B 107.2 . . ?
H13A C13 H13B 106.9 . . ?
C36 C14 C15 107.1(5) . . ?
C36 C14 C13 106.6(5) . . ?
C15 C14 C13 115.4(5) . . ?
C36 C14 C37 107.6(5) . . ?
C15 C14 C37 108.4(5) . . ?
C13 C14 C37 111.3(5) . . ?
O16 C15 C38 108.3(4) . . ?
O16 C15 C14 107.6(4) . . ?
C38 C15 C14 116.9(5) . . ?
O16 C15 H15 107.9 . . ?
C38 C15 H15 107.9 . . ?
C14 C15 H15 107.9 . . ?
C1 O16 C15 118.9(4) . . ?
C5 O18 C19 117.6(4) . . ?
O18 C19 C20 107.7(4) . . ?
O18 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O18 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C21 C20 C25 119.2(5) . . ?
C21 C20 C19 121.4(5) . . ?
C25 C20 C19 119.5(5) . . ?
C22 C21 C20 120.5(6) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 119.2(7) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 C22 120.8(6) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.8(7) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 120.5(7) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C7 O26 C27 118.3(4) . . ?
O26 C27 C28 107.9(4) . . ?
O26 C27 H27A 110.1 . . ?
C28 C27 H27A 110.1 . . ?
O26 C27 H27B 110.1 . . ?
C28 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
C33 C28 C29 118.4(6) . . ?
C33 C28 C27 122.6(5) . . ?
C29 C28 C27 118.7(5) . . ?
C30 C29 C28 120.2(6) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.4(7) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 119.9(7) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.0(7) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 121.1(6) . . ?
C32 C33 H33 119.5 . . ?
C28 C33 H33 119.5 . . ?
C10 C35 H35A 109.5 . . ?
C10 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C10 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C14 C36 H36A 109.5 . . ?
C14 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C14 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C14 C37 H37A 109.5 . . ?
C14 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C14 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C15 C38 H38A 109.5 . . ?
C15 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C15 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
O17 C1 C2 C3 102.2(6) . . . . ?
O16 C1 C2 C3 -74.3(5) . . . . ?
C1 C2 C3 C8 115.7(5) . . . . ?
C1 C2 C3 C4 -62.1(6) . . . . ?
C8 C3 C4 C5 -1.1(8) . . . . ?
C2 C3 C4 C5 176.8(5) . . . . ?
C3 C4 C5 O18 -178.5(5) . . . . ?
C3 C4 C5 C6 1.9(8) . . . . ?
O18 C5 C6 C7 180.0(5) . . . . ?
C4 C5 C6 C7 -0.5(8) . . . . ?
C5 C6 C7 O26 -179.3(5) . . . . ?
C5 C6 C7 C8 -1.7(8) . . . . ?
C4 C3 C8 C7 -1.0(8) . . . . ?
C2 C3 C8 C7 -178.8(5) . . . . ?
C4 C3 C8 C9 -177.4(5) . . . . ?
C2 C3 C8 C9 4.8(8) . . . . ?
O26 C7 C8 C3 -179.8(5) . . . . ?
C6 C7 C8 C3 2.4(8) . . . . ?
O26 C7 C8 C9 -3.2(7) . . . . ?
C6 C7 C8 C9 179.1(5) . . . . ?
C3 C8 C9 O34 94.2(6) . . . . ?
C7 C8 C9 O34 -82.2(7) . . . . ?
C3 C8 C9 C10 -81.4(7) . . . . ?
C7 C8 C9 C10 102.2(6) . . . . ?
O34 C9 C10 C11 -177.9(5) . . . . ?
C8 C9 C10 C11 -2.4(8) . . . . ?
O34 C9 C10 C35 1.6(8) . . . . ?
C8 C9 C10 C35 177.1(5) . . . . ?
C9 C10 C11 C12 174.8(5) . . . . ?
C35 C10 C11 C12 -4.7(9) . . . . ?
C10 C11 C12 C13 -164.3(5) . . . . ?
C11 C12 C13 C14 75.8(7) . . . . ?
C12 C13 C14 C36 163.8(5) . . . . ?
C12 C13 C14 C15 -77.5(6) . . . . ?
C12 C13 C14 C37 46.7(7) . . . . ?
C36 C14 C15 O16 -175.8(4) . . . . ?
C13 C14 C15 O16 65.7(6) . . . . ?
C37 C14 C15 O16 -60.0(6) . . . . ?
C36 C14 C15 C38 62.1(6) . . . . ?
C13 C14 C15 C38 -56.4(7) . . . . ?
C37 C14 C15 C38 177.9(5) . . . . ?
O17 C1 O16 C15 -16.6(7) . . . . ?
C2 C1 O16 C15 160.0(4) . . . . ?
C38 C15 O16 C1 -72.9(6) . . . . ?
C14 C15 O16 C1 159.9(4) . . . . ?
C6 C5 O18 C19 4.8(8) . . . . ?
C4 C5 O18 C19 -174.8(5) . . . . ?
C5 O18 C19 C20 166.3(5) . . . . ?
O18 C19 C20 C21 75.4(7) . . . . ?
O18 C19 C20 C25 -104.6(6) . . . . ?
C25 C20 C21 C22 -0.5(10) . . . . ?
C19 C20 C21 C22 179.6(6) . . . . ?
C20 C21 C22 C23 0.5(12) . . . . ?
C21 C22 C23 C24 -1.8(13) . . . . ?
C22 C23 C24 C25 3.0(13) . . . . ?
C23 C24 C25 C20 -3.0(11) . . . . ?
C21 C20 C25 C24 1.7(10) . . . . ?
C19 C20 C25 C24 -178.3(6) . . . . ?
C6 C7 O26 C27 -11.5(8) . . . . ?
C8 C7 O26 C27 170.8(5) . . . . ?
C7 O26 C27 C28 -168.1(5) . . . . ?
O26 C27 C28 C33 10.9(8) . . . . ?
O26 C27 C28 C29 -174.2(5) . . . . ?
C33 C28 C29 C30 -2.5(11) . . . . ?
C27 C28 C29 C30 -177.6(7) . . . . ?
C28 C29 C30 C31 0.4(13) . . . . ?
C29 C30 C31 C32 1.4(14) . . . . ?
C30 C31 C32 C33 -1.0(14) . . . . ?
C31 C32 C33 C28 -1.2(13) . . . . ?
C29 C28 C33 C32 2.9(11) . . . . ?
C27 C28 C33 C32 177.8(7) . . . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.119


####################################################################### 
# 
# 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 1998326'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
(E)-11,13-bis(benzyloxy)-9-ethyl-4,5,5-trimethyl-4,5,6,7-tetrahydro-2H-benzo[d][1]oxacyclododecine-2,10(1H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H38 O5'
_chemical_formula_sum            'C34 H38 O5'
_chemical_formula_weight         526.64

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.2297(6)
_cell_length_b                   15.8502(9)
_cell_length_c                   25.683(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.935(7)
_cell_angle_gamma                90
_cell_volume                     2927.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9699
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      28.27

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 130 frames, detector distance = 80 mm
;
_diffrn_reflns_number            12741
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.048
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6628
_reflns_number_gt                3534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SHELXT-2014
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0002P)²+8.5380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         6628
_refine_ls_number_parameters     362
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1988
_refine_ls_R_factor_gt           0.1002
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.134
_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
C1 C 0.2592(7) 0.3293(3) 0.3757(2) 0.0426(11) Uani 1 1 d D . . . .
C2 C 0.1868(6) 0.3883(3) 0.33160(18) 0.0381(11) Uani 1 1 d . . . . .
H2A H 0.091101 0.359372 0.307638 0.046 Uiso 1 1 calc R U . . .
H2B H 0.129485 0.438710 0.346109 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3485(6) 0.4145(3) 0.30213(17) 0.0319(9) Uani 1 1 d . . . . .
C4 C 0.4909(6) 0.4630(2) 0.32921(17) 0.0319(9) Uani 1 1 d . . . . .
H4 H 0.479702 0.481386 0.363946 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6477(6) 0.4838(2) 0.30493(17) 0.0316(9) Uani 1 1 d . . . . .
C6 C 0.6624(6) 0.4597(3) 0.25296(16) 0.0309(9) Uani 1 1 d . . . . .
H6 H 0.768314 0.475235 0.236111 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5209(6) 0.4131(3) 0.22664(16) 0.0304(9) Uani 1 1 d . . . . .
C8 C 0.3631(6) 0.3895(2) 0.25124(17) 0.0295(9) Uani 1 1 d . . . . .
C9 C 0.2116(5) 0.3397(3) 0.21989(18) 0.0329(10) Uani 1 1 d . . . . .
C10 C 0.1998(6) 0.2477(3) 0.22705(17) 0.0331(10) Uani 1 1 d . . . . .
C11 C 0.3454(6) 0.2079(3) 0.25332(17) 0.0327(9) Uani 1 1 d . . . . .
H11 H 0.447593 0.242249 0.266287 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3634(6) 0.1154(3) 0.26427(18) 0.0376(10) Uani 1 1 d . . . . .
H12A H 0.422038 0.088553 0.235290 0.045 Uiso 1 1 calc R U . . .
H12B H 0.237088 0.091298 0.264246 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4772(6) 0.0918(3) 0.31634(17) 0.0353(10) Uani 1 1 d . . . . .
H13A H 0.598377 0.121139 0.317366 0.042 Uiso 1 1 calc R U . . .
H13B H 0.503179 0.030511 0.315274 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3961(6) 0.1104(3) 0.36880(18) 0.0360(10) Uani 1 1 d . . . . .
C15 C 0.4291(6) 0.1994(3) 0.39030(18) 0.0375(10) Uani 1 1 d . . . . .
H15 H 0.385422 0.202043 0.425955 0.045 Uiso 1 1 calc R U . . .
O16 O 0.3165(4) 0.25759(18) 0.35585(12) 0.0389(7) Uani 1 1 d . . . . .
O17 O 0.307(4) 0.346(3) 0.4225(6) 0.048(5) Uani 0.47 1 d D . P A 1
O17A O 0.251(4) 0.346(3) 0.4229(6) 0.048(5) Uani 0.43 1 d D . P A 2
O17B O 0.136(4) 0.327(2) 0.4067(13) 0.048(5) Uani 0.1 1 d D . P A 3
O18 O 0.7968(4) 0.52740(18) 0.32854(11) 0.0339(7) Uani 1 1 d . . . . .
C19 C 0.7931(6) 0.5484(3) 0.38316(17) 0.0404(11) Uani 1 1 d . . . . .
H19A H 0.764276 0.497590 0.403239 0.049 Uiso 1 1 calc R U . . .
H19B H 0.696257 0.591399 0.387191 0.049 Uiso 1 1 calc R U . . .
C20 C 0.9812(6) 0.5822(3) 0.40311(17) 0.0389(11) Uani 1 1 d . . . . .
C21 C 1.0941(7) 0.5374(4) 0.4395(2) 0.0541(14) Uani 1 1 d . . . . .
H21 H 1.053228 0.484653 0.451576 0.065 Uiso 1 1 calc R U . . .
C22 C 1.2670(9) 0.5684(5) 0.4588(3) 0.079(2) Uani 1 1 d . . . . .
H22 H 1.344385 0.537097 0.484007 0.095 Uiso 1 1 calc R U . . .
C23 C 1.3260(9) 0.6458(6) 0.4410(3) 0.085(2) Uani 1 1 d . . . . .
H23 H 1.444158 0.667663 0.454109 0.102 Uiso 1 1 calc R U . . .
C24 C 1.2130(9) 0.6908(4) 0.4045(2) 0.0708(18) Uani 1 1 d . . . . .
H24 H 1.253207 0.743671 0.392251 0.085 Uiso 1 1 calc R U . . .
C25 C 1.0434(7) 0.6594(3) 0.3858(2) 0.0520(13) Uani 1 1 d . . . . .
H25 H 0.966302 0.690712 0.360567 0.062 Uiso 1 1 calc R U . . .
O26 O 0.5205(4) 0.38505(18) 0.17625(11) 0.0348(7) Uani 1 1 d . . . . .
C27 C 0.6655(6) 0.4155(3) 0.14633(16) 0.0346(10) Uani 1 1 d . . . . .
H27A H 0.789166 0.397839 0.162883 0.042 Uiso 1 1 calc R U . . .
H27B H 0.662525 0.477902 0.144260 0.042 Uiso 1 1 calc R U . . .
C28 C 0.6281(6) 0.3776(3) 0.09265(17) 0.0368(10) Uani 1 1 d . . . . .
C29 C 0.4650(7) 0.3950(4) 0.0621(2) 0.0644(17) Uani 1 1 d . . . . .
H29 H 0.378327 0.433386 0.074373 0.077 Uiso 1 1 calc R U . . .
C30 C 0.4259(9) 0.3571(4) 0.0136(2) 0.081(2) Uani 1 1 d . . . . .
H30 H 0.311439 0.368741 -0.006763 0.097 Uiso 1 1 calc R U . . .
C31 C 0.5516(7) 0.3025(4) -0.0056(2) 0.0543(14) Uani 1 1 d . . . . .
H31 H 0.525399 0.277023 -0.038998 0.065 Uiso 1 1 calc R U . . .
C32 C 0.7134(7) 0.2860(3) 0.02442(18) 0.0487(13) Uani 1 1 d . . . . .
H32 H 0.800535 0.248113 0.011919 0.058 Uiso 1 1 calc R U . . .
C33 C 0.7535(6) 0.3238(3) 0.07315(18) 0.0421(11) Uani 1 1 d . . . . .
H33 H 0.868704 0.312290 0.093187 0.050 Uiso 1 1 calc R U . . .
O34 O 0.0983(4) 0.3770(2) 0.18914(14) 0.0472(9) Uani 1 1 d . . . . .
C35 C 0.0235(6) 0.2054(3) 0.20452(18) 0.0369(10) Uani 1 1 d . . . . .
H35A H 0.047582 0.144445 0.200181 0.044 Uiso 1 1 calc R U . . .
H35B H -0.014904 0.229241 0.169436 0.044 Uiso 1 1 calc R U . . .
C36 C -0.1355(6) 0.2163(3) 0.2390(2) 0.0472(12) Uani 1 1 d . . . . .
H36A H -0.167008 0.276268 0.241068 0.071 Uiso 1 1 calc R U . . .
H36B H -0.096619 0.194805 0.274208 0.071 Uiso 1 1 calc R U . . .
H36C H -0.244652 0.184833 0.223782 0.071 Uiso 1 1 calc R U . . .
C37 C 0.4919(7) 0.0492(3) 0.41006(19) 0.0470(12) Uani 1 1 d . . . . .
H37A H 0.451335 0.062051 0.444442 0.070 Uiso 1 1 calc R U . . .
H37B H 0.627071 0.055834 0.411520 0.070 Uiso 1 1 calc R U . . .
H37C H 0.457846 -0.008960 0.400374 0.070 Uiso 1 1 calc R U . . .
C38 C 0.1865(6) 0.0908(3) 0.3633(2) 0.0458(12) Uani 1 1 d . . . . .
H38A H 0.139985 0.093816 0.397722 0.069 Uiso 1 1 calc R U . . .
H38B H 0.165455 0.033991 0.348779 0.069 Uiso 1 1 calc R U . . .
H38C H 0.120658 0.132096 0.339756 0.069 Uiso 1 1 calc R U . . .
C39 C 0.6263(7) 0.2319(3) 0.3937(2) 0.0555(15) Uani 1 1 d . . . . .
H39A H 0.711145 0.188909 0.409862 0.083 Uiso 1 1 calc R U . . .
H39B H 0.636622 0.283301 0.415029 0.083 Uiso 1 1 calc R U . . .
H39C H 0.659018 0.244616 0.358468 0.083 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
C1 O17 1.246(12) . ?
C1 O17A 1.250(12) . ?
C1 O17B 1.257(17) . ?
C1 O16 1.328(5) . ?
C1 C2 1.519(6) . ?
C2 C3 1.515(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.380(6) . ?
C3 C4 1.410(6) . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 O18 1.368(5) . ?
C5 C6 1.403(6) . ?
C6 C7 1.380(6) . ?
C6 H6 0.9500 . ?
C7 O26 1.369(5) . ?
C7 C8 1.411(6) . ?
C8 C9 1.513(6) . ?
C9 O34 1.229(5) . ?
C9 C10 1.473(6) . ?
C10 C11 1.347(6) . ?
C10 C35 1.503(6) . ?
C11 C12 1.496(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.542(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.552(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(6) . ?
C14 C38 1.539(6) . ?
C14 C37 1.546(6) . ?
C15 O16 1.465(5) . ?
C15 C39 1.510(6) . ?
C15 H15 1.0000 . ?
O18 C19 1.445(5) . ?
C19 C20 1.502(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.373(7) . ?
C20 C25 1.392(7) . ?
C21 C22 1.386(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.364(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O26 C27 1.446(5) . ?
C27 C28 1.503(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.375(6) . ?
C28 C33 1.377(6) . ?
C29 C30 1.387(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.358(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.390(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C35 C36 1.532(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
O17 C1 O16 119.3(19) . . ?
O17A C1 O16 127(2) . . ?
O17B C1 O16 119.3(16) . . ?
O17 C1 C2 129(2) . . ?
O17A C1 C2 123(2) . . ?
O17B C1 C2 106.1(17) . . ?
O16 C1 C2 109.8(4) . . ?
C3 C2 C1 108.5(4) . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C8 C3 C4 120.0(4) . . ?
C8 C3 C2 122.2(4) . . ?
C4 C3 C2 117.7(4) . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O18 C5 C4 124.3(4) . . ?
O18 C5 C6 115.2(4) . . ?
C4 C5 C6 120.6(4) . . ?
C7 C6 C5 119.1(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O26 C7 C6 124.5(4) . . ?
O26 C7 C8 114.5(3) . . ?
C6 C7 C8 121.0(4) . . ?
C3 C8 C7 119.5(4) . . ?
C3 C8 C9 122.1(4) . . ?
C7 C8 C9 118.4(4) . . ?
O34 C9 C10 120.9(4) . . ?
O34 C9 C8 119.3(4) . . ?
C10 C9 C8 119.9(4) . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 C35 124.9(4) . . ?
C9 C10 C35 116.8(4) . . ?
C10 C11 C12 127.0(4) . . ?
C10 C11 H11 116.5 . . ?
C12 C11 H11 116.5 . . ?
C11 C12 C13 115.4(4) . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 H13A 107.5 . . ?
C14 C13 H13A 107.5 . . ?
C12 C13 H13B 107.5 . . ?
C14 C13 H13B 107.5 . . ?
H13A C13 H13B 107.0 . . ?
C15 C14 C38 109.6(4) . . ?
C15 C14 C37 106.9(4) . . ?
C38 C14 C37 107.7(4) . . ?
C15 C14 C13 115.5(4) . . ?
C38 C14 C13 109.7(4) . . ?
C37 C14 C13 107.1(4) . . ?
O16 C15 C39 106.4(4) . . ?
O16 C15 C14 107.9(3) . . ?
C39 C15 C14 116.6(4) . . ?
O16 C15 H15 108.5 . . ?
C39 C15 H15 108.5 . . ?
C14 C15 H15 108.5 . . ?
C1 O16 C15 118.9(4) . . ?
C5 O18 C19 117.0(3) . . ?
O18 C19 C20 107.8(4) . . ?
O18 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O18 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.5 . . ?
C21 C20 C25 118.9(5) . . ?
C21 C20 C19 120.1(5) . . ?
C25 C20 C19 121.0(4) . . ?
C20 C21 C22 120.8(6) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.4(6) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.0(6) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.9(6) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 121.2(6) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
C7 O26 C27 117.6(3) . . ?
O26 C27 C28 106.4(3) . . ?
O26 C27 H27A 110.5 . . ?
C28 C27 H27A 110.5 . . ?
O26 C27 H27B 110.5 . . ?
C28 C27 H27B 110.5 . . ?
H27A C27 H27B 108.6 . . ?
C29 C28 C33 118.4(4) . . ?
C29 C28 C27 120.4(4) . . ?
C33 C28 C27 121.3(4) . . ?
C28 C29 C30 120.6(5) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.7(5) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C30 118.6(5) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C31 C32 C33 121.0(5) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C28 C33 C32 120.7(4) . . ?
C28 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C10 C35 C36 112.6(4) . . ?
C10 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
C10 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C14 C37 H37A 109.5 . . ?
C14 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C14 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C14 C38 H38A 109.5 . . ?
C14 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C14 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C15 C39 H39A 109.5 . . ?
C15 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C15 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
O17 C1 C2 C3 95.7(17) . . . . ?
O17A C1 C2 C3 118(2) . . . . ?
O17B C1 C2 C3 163.1(18) . . . . ?
O16 C1 C2 C3 -66.8(5) . . . . ?
C1 C2 C3 C8 112.4(5) . . . . ?
C1 C2 C3 C4 -64.9(5) . . . . ?
C8 C3 C4 C5 -1.5(6) . . . . ?
C2 C3 C4 C5 175.8(4) . . . . ?
C3 C4 C5 O18 -177.1(4) . . . . ?
C3 C4 C5 C6 2.5(6) . . . . ?
O18 C5 C6 C7 178.0(4) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C5 C6 C7 O26 -179.1(4) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C4 C3 C8 C7 -0.2(6) . . . . ?
C2 C3 C8 C7 -177.5(4) . . . . ?
C4 C3 C8 C9 -178.1(4) . . . . ?
C2 C3 C8 C9 4.7(6) . . . . ?
O26 C7 C8 C3 -179.9(4) . . . . ?
C6 C7 C8 C3 1.1(6) . . . . ?
O26 C7 C8 C9 -2.0(5) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C3 C8 C9 O34 97.7(5) . . . . ?
C7 C8 C9 O34 -80.1(5) . . . . ?
C3 C8 C9 C10 -81.4(5) . . . . ?
C7 C8 C9 C10 100.7(5) . . . . ?
O34 C9 C10 C11 167.7(4) . . . . ?
C8 C9 C10 C11 -13.2(6) . . . . ?
O34 C9 C10 C35 -12.8(7) . . . . ?
C8 C9 C10 C35 166.3(4) . . . . ?
C9 C10 C11 C12 -179.1(4) . . . . ?
C35 C10 C11 C12 1.4(8) . . . . ?
C10 C11 C12 C13 -147.6(5) . . . . ?
C11 C12 C13 C14 70.1(5) . . . . ?
C12 C13 C14 C15 -84.6(5) . . . . ?
C12 C13 C14 C38 39.9(5) . . . . ?
C12 C13 C14 C37 156.5(4) . . . . ?
C38 C14 C15 O16 -55.1(5) . . . . ?
C37 C14 C15 O16 -171.5(4) . . . . ?
C13 C14 C15 O16 69.5(5) . . . . ?
C38 C14 C15 C39 -174.7(4) . . . . ?
C37 C14 C15 C39 68.8(5) . . . . ?
C13 C14 C15 C39 -50.2(5) . . . . ?
O17 C1 O16 C15 2.2(19) . . . . ?
O17A C1 O16 C15 -18(2) . . . . ?
O17B C1 O16 C15 -71(2) . . . . ?
C2 C1 O16 C15 166.5(4) . . . . ?
C39 C15 O16 C1 -81.8(5) . . . . ?
C14 C15 O16 C1 152.4(4) . . . . ?
C4 C5 O18 C19 3.7(6) . . . . ?
C6 C5 O18 C19 -175.9(4) . . . . ?
C5 O18 C19 C20 170.5(4) . . . . ?
O18 C19 C20 C21 -112.8(5) . . . . ?
O18 C19 C20 C25 68.1(6) . . . . ?
C25 C20 C21 C22 0.1(8) . . . . ?
C19 C20 C21 C22 -179.0(5) . . . . ?
C20 C21 C22 C23 0.1(9) . . . . ?
C21 C22 C23 C24 -0.1(10) . . . . ?
C22 C23 C24 C25 0.1(10) . . . . ?
C23 C24 C25 C20 0.1(9) . . . . ?
C21 C20 C25 C24 -0.1(8) . . . . ?
C19 C20 C25 C24 179.0(5) . . . . ?
C6 C7 O26 C27 -8.6(6) . . . . ?
C8 C7 O26 C27 172.4(3) . . . . ?
C7 O26 C27 C28 -178.1(3) . . . . ?
O26 C27 C28 C29 61.2(6) . . . . ?
O26 C27 C28 C33 -117.7(5) . . . . ?
C33 C28 C29 C30 2.0(9) . . . . ?
C27 C28 C29 C30 -177.0(6) . . . . ?
C28 C29 C30 C31 -1.4(11) . . . . ?
C29 C30 C31 C32 0.7(10) . . . . ?
C30 C31 C32 C33 -0.7(9) . . . . ?
C29 C28 C33 C32 -1.9(8) . . . . ?
C27 C28 C33 C32 177.0(4) . . . . ?
C31 C32 C33 C28 1.3(8) . . . . ?
C11 C10 C35 C36 100.5(5) . . . . ?
C9 C10 C35 C36 -79.0(5) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1998325'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
(E)-14-chloro-11,13-dihydroxy-4,5,5,9-tetramethyl-4,5,6,7-tetrahydro-2H-benzo[d][1]oxacyclododecine-2,10(1H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 Cl O5'
_chemical_formula_sum            'C19 H23 Cl O5'
_chemical_formula_weight         366.82

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           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   11.1913(5)
_cell_length_b                   36.617(2)
_cell_length_c                   8.3725(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3431.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    12816
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      28.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 215 frames, detector distance = 70 mm
;
_diffrn_reflns_number            12113
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         28.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             3929
_reflns_number_gt                3343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.816
_reflns_Friedel_fraction_full    0.861

_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0408P)²+8.3592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 -0.06153(8) 0.36069(2) 0.33790(14) 0.0225(2) Uani 1 1 d . . . . .
O1 O 0.2016(3) 0.40492(7) 0.1701(4) 0.0221(6) Uani 1 1 d . . . . .
C1 C 0.2069(3) 0.39926(10) 0.3279(6) 0.0210(8) Uani 1 1 d . . . . .
O2 O 0.2166(4) 0.42311(9) 0.4247(5) 0.0462(11) Uani 1 1 d . . . . .
C2 C 0.2064(4) 0.35950(11) 0.3727(5) 0.0195(9) Uani 1 1 d . . . . .
H2A H 0.169(4) 0.3592(13) 0.473(7) 0.023 Uiso 1 1 d . U . . .
H2B H 0.294(4) 0.3537(13) 0.392(6) 0.023 Uiso 1 1 d . U . . .
O3 O -0.1436(2) 0.30037(8) 0.1463(4) 0.0218(6) Uani 1 1 d . . . . .
H3 H -0.162(6) 0.2808(19) 0.097(9) 0.05(2) Uiso 1 1 d . . . . .
C3 C 0.1535(3) 0.33225(11) 0.2575(5) 0.0169(7) Uani 1 1 d . . . . .
O4 O 0.2472(3) 0.25825(8) -0.0084(4) 0.0185(6) Uani 1 1 d . . . . .
H4 H 0.212(5) 0.2481(16) -0.073(8) 0.036(17) Uiso 1 1 d . . . . .
C4 C 0.0302(3) 0.32961(11) 0.2409(5) 0.0188(8) Uani 1 1 d . . . . .
O5 O 0.3946(2) 0.27812(8) 0.2814(4) 0.0209(6) Uani 1 1 d . . . . .
C5 C -0.0223(3) 0.30230(11) 0.1495(5) 0.0180(8) Uani 1 1 d . . . . .
C6 C 0.0493(4) 0.27847(11) 0.0626(5) 0.0183(8) Uani 1 1 d . . . . .
H6 H 0.010(5) 0.2615(12) -0.005(7) 0.024(12) Uiso 1 1 d . . . . .
C7 C 0.1728(4) 0.28117(11) 0.0756(5) 0.0168(8) Uani 1 1 d . . . . .
C8 C 0.2262(3) 0.30741(10) 0.1750(5) 0.0170(8) Uani 1 1 d . . . . .
C9 C 0.3584(3) 0.30442(10) 0.2032(5) 0.0157(7) Uani 1 1 d . . . . .
C10 C 0.4437(3) 0.33188(11) 0.1438(5) 0.0182(8) Uani 1 1 d . . . . .
C11 C 0.4000(4) 0.36046(11) 0.0601(5) 0.0197(8) Uani 1 1 d . . . . .
H11 H 0.311(5) 0.3605(14) 0.035(7) 0.029(13) Uiso 1 1 d . . . . .
C12 C 0.4701(4) 0.39231(11) -0.0010(6) 0.0237(9) Uani 1 1 d . . . . .
H12A H 0.466(4) 0.3911(13) -0.125(7) 0.025(9) Uiso 1 1 d . U . . .
H12B H 0.561(4) 0.3892(13) 0.034(7) 0.025(9) Uiso 1 1 d . U . . .
C13 C 0.4273(4) 0.43076(11) 0.0539(6) 0.0236(9) Uani 1 1 d . . . . .
H13A H 0.495(5) 0.4480(12) 0.017(7) 0.026(9) Uiso 1 1 d . U . . .
H13B H 0.425(4) 0.4311(13) 0.181(7) 0.026(9) Uiso 1 1 d . U . . .
C14 C 0.3076(4) 0.44668(11) -0.0112(5) 0.0209(8) Uani 1 1 d . . . . .
C15 C 0.2074(4) 0.44283(11) 0.1143(6) 0.0245(9) Uani 1 1 d . . . . .
H15 H 0.227(4) 0.4578(12) 0.211(6) 0.011(10) Uiso 1 1 d . . . . .
C16 C 0.5729(4) 0.32469(13) 0.1817(6) 0.0237(9) Uani 1 1 d . . . . .
H16A H 0.582(4) 0.3137(14) 0.285(7) 0.031(8) Uiso 1 1 d . U . . .
H16B H 0.618(5) 0.3459(16) 0.172(7) 0.031(8) Uiso 1 1 d . U . . .
H16C H 0.606(5) 0.3041(15) 0.110(7) 0.031(8) Uiso 1 1 d . U . . .
C17 C 0.2739(4) 0.43076(12) -0.1728(7) 0.0271(9) Uani 1 1 d . . . . .
H17A H 0.259(4) 0.4046(14) -0.165(7) 0.033(8) Uiso 1 1 d . U . . .
H17B H 0.339(5) 0.4339(15) -0.248(8) 0.033(8) Uiso 1 1 d . U . . .
H17C H 0.201(5) 0.4419(14) -0.224(7) 0.033(8) Uiso 1 1 d . U . . .
C18 C 0.3270(4) 0.48807(12) -0.0314(6) 0.0295(10) Uani 1 1 d . . . . .
H18A H 0.354698 0.498511 0.069806 0.039(8) Uiso 1 1 calc R U . . .
H18B H 0.251486 0.499642 -0.062397 0.039(8) Uiso 1 1 calc R U . . .
H18C H 0.387016 0.492389 -0.114455 0.039(8) Uiso 1 1 calc R U . . .
C19 C 0.0815(4) 0.45241(14) 0.0592(7) 0.0361(12) Uani 1 1 d . . . . .
H19A H 0.081278 0.476989 0.012831 0.051(11) Uiso 1 1 calc R U . . .
H19B H 0.026915 0.451671 0.150652 0.051(11) Uiso 1 1 calc R U . . .
H19C H 0.055259 0.434734 -0.021431 0.051(11) 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 C4 1.734(4) . ?
O1 C1 1.339(5) . ?
O1 C15 1.466(5) . ?
C1 O2 1.196(5) . ?
C1 C2 1.503(6) . ?
C2 C3 1.508(6) . ?
C2 H2A 0.94(6) . ?
C2 H2B 1.01(5) . ?
O3 C5 1.360(4) . ?
O3 H3 0.85(7) . ?
C3 C4 1.391(5) . ?
C3 C8 1.402(5) . ?
O4 C7 1.375(5) . ?
O4 H4 0.77(6) . ?
C4 C5 1.389(6) . ?
O5 C9 1.233(5) . ?
C5 C6 1.390(6) . ?
C6 C7 1.390(6) . ?
C6 H6 0.95(5) . ?
C7 C8 1.405(5) . ?
C8 C9 1.502(5) . ?
C9 C10 1.473(5) . ?
C10 C11 1.352(6) . ?
C10 C16 1.503(6) . ?
C11 C12 1.496(6) . ?
C11 H11 1.02(5) . ?
C12 C13 1.557(6) . ?
C12 H12A 1.04(5) . ?
C12 H12B 1.06(5) . ?
C13 C14 1.559(6) . ?
C13 H13A 1.03(5) . ?
C13 H13B 1.06(6) . ?
C14 C17 1.521(7) . ?
C14 C18 1.540(6) . ?
C14 C15 1.542(6) . ?
C15 C19 1.524(7) . ?
C15 H15 1.00(5) . ?
C16 H16A 0.96(6) . ?
C16 H16B 0.93(6) . ?
C16 H16C 1.03(6) . ?
C17 H17A 0.97(5) . ?
C17 H17B 0.97(6) . ?
C17 H17C 1.01(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 C15 117.3(3) . . ?
O2 C1 O1 124.0(4) . . ?
O2 C1 C2 122.6(4) . . ?
O1 C1 C2 113.3(3) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2A 104(3) . . ?
C3 C2 H2A 113(3) . . ?
C1 C2 H2B 104(3) . . ?
C3 C2 H2B 110(3) . . ?
H2A C2 H2B 107(4) . . ?
C5 O3 H3 107(5) . . ?
C4 C3 C8 118.8(4) . . ?
C4 C3 C2 119.9(4) . . ?
C8 C3 C2 121.1(3) . . ?
C7 O4 H4 110(4) . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 Cl1 118.7(3) . . ?
C3 C4 Cl1 119.7(3) . . ?
O3 C5 C4 118.0(4) . . ?
O3 C5 C6 122.1(4) . . ?
C4 C5 C6 119.8(3) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 117(3) . . ?
C7 C6 H6 124(3) . . ?
O4 C7 C6 121.2(4) . . ?
O4 C7 C8 117.6(3) . . ?
C6 C7 C8 121.2(4) . . ?
C3 C8 C7 119.3(3) . . ?
C3 C8 C9 122.8(4) . . ?
C7 C8 C9 117.5(3) . . ?
O5 C9 C10 119.9(3) . . ?
O5 C9 C8 117.7(3) . . ?
C10 C9 C8 122.4(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 C16 126.4(4) . . ?
C9 C10 C16 115.7(3) . . ?
C10 C11 C12 126.2(4) . . ?
C10 C11 H11 117(3) . . ?
C12 C11 H11 116(3) . . ?
C11 C12 C13 116.3(4) . . ?
C11 C12 H12A 107(3) . . ?
C13 C12 H12A 109(3) . . ?
C11 C12 H12B 109(3) . . ?
C13 C12 H12B 108(3) . . ?
H12A C12 H12B 108(4) . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13A 104(3) . . ?
C14 C13 H13A 107(3) . . ?
C12 C13 H13B 108(3) . . ?
C14 C13 H13B 109(3) . . ?
H13A C13 H13B 108(4) . . ?
C17 C14 C18 108.3(4) . . ?
C17 C14 C15 113.0(4) . . ?
C18 C14 C15 105.5(3) . . ?
C17 C14 C13 112.4(4) . . ?
C18 C14 C13 106.6(3) . . ?
C15 C14 C13 110.6(4) . . ?
O1 C15 C19 105.9(4) . . ?
O1 C15 C14 109.6(3) . . ?
C19 C15 C14 116.4(4) . . ?
O1 C15 H15 106(3) . . ?
C19 C15 H15 109(2) . . ?
C14 C15 H15 110(2) . . ?
C10 C16 H16A 111(3) . . ?
C10 C16 H16B 111(3) . . ?
H16A C16 H16B 112(5) . . ?
C10 C16 H16C 110(3) . . ?
H16A C16 H16C 101(4) . . ?
H16B C16 H16C 111(5) . . ?
C14 C17 H17A 111(4) . . ?
C14 C17 H17B 110(3) . . ?
H17A C17 H17B 107(5) . . ?
C14 C17 H17C 115(3) . . ?
H17A C17 H17C 107(4) . . ?
H17B C17 H17C 106(5) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C15 O1 C1 O2 -0.4(6) . . . . ?
C15 O1 C1 C2 -177.1(3) . . . . ?
O2 C1 C2 C3 159.6(4) . . . . ?
O1 C1 C2 C3 -23.6(5) . . . . ?
C1 C2 C3 C4 -75.1(5) . . . . ?
C1 C2 C3 C8 109.8(5) . . . . ?
C8 C3 C4 C5 2.3(6) . . . . ?
C2 C3 C4 C5 -172.9(4) . . . . ?
C8 C3 C4 Cl1 -178.4(3) . . . . ?
C2 C3 C4 Cl1 6.3(5) . . . . ?
C3 C4 C5 O3 176.5(4) . . . . ?
Cl1 C4 C5 O3 -2.8(5) . . . . ?
C3 C4 C5 C6 -4.8(6) . . . . ?
Cl1 C4 C5 C6 175.9(3) . . . . ?
O3 C5 C6 C7 -177.8(4) . . . . ?
C4 C5 C6 C7 3.5(6) . . . . ?
C5 C6 C7 O4 -179.9(4) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C4 C3 C8 C7 1.4(6) . . . . ?
C2 C3 C8 C7 176.5(4) . . . . ?
C4 C3 C8 C9 -170.8(4) . . . . ?
C2 C3 C8 C9 4.3(6) . . . . ?
O4 C7 C8 C3 177.4(4) . . . . ?
C6 C7 C8 C3 -2.6(6) . . . . ?
O4 C7 C8 C9 -10.0(5) . . . . ?
C6 C7 C8 C9 170.0(4) . . . . ?
C3 C8 C9 O5 104.3(5) . . . . ?
C7 C8 C9 O5 -68.0(5) . . . . ?
C3 C8 C9 C10 -74.5(5) . . . . ?
C7 C8 C9 C10 113.2(4) . . . . ?
O5 C9 C10 C11 -179.3(4) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
O5 C9 C10 C16 1.5(6) . . . . ?
C8 C9 C10 C16 -179.7(4) . . . . ?
C9 C10 C11 C12 175.8(4) . . . . ?
C16 C10 C11 C12 -5.1(7) . . . . ?
C10 C11 C12 C13 -123.3(5) . . . . ?
C11 C12 C13 C14 -70.4(6) . . . . ?
C12 C13 C14 C17 -25.5(6) . . . . ?
C12 C13 C14 C18 -144.0(4) . . . . ?
C12 C13 C14 C15 101.8(5) . . . . ?
C1 O1 C15 C19 -107.0(4) . . . . ?
C1 O1 C15 C14 126.7(4) . . . . ?
C17 C14 C15 O1 75.2(5) . . . . ?
C18 C14 C15 O1 -166.7(4) . . . . ?
C13 C14 C15 O1 -51.8(5) . . . . ?
C17 C14 C15 C19 -44.9(5) . . . . ?
C18 C14 C15 C19 73.3(5) . . . . ?
C13 C14 C15 C19 -171.8(4) . . . . ?

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
C2 H2A O3 0.94(6) 2.61(5) 3.230(5) 124(4) 3 yes
O3 H3 O4 0.85(7) 1.96(7) 2.789(4) 162(7) 8_454 yes
O4 H4 O5 0.77(6) 1.95(6) 2.718(4) 173(6) 6_554 yes
C6 H6 O5 0.95(5) 2.54(5) 3.198(5) 127(4) 6_554 yes
C19 H19C Cl1 0.98 2.96 3.842(6) 150.8 3_554 yes

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.066

