# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ch15_pk249
_database_code_depnum_ccdc_archive 'CCDC 1971573'
loop_
_audit_author_name
_audit_author_address
'Joachim Kusz'
;University of Silesia, Katowice
Poland
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 O4'
_chemical_formula_sum            'C24 H22 O4'
_chemical_formula_weight         374.41

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                   5.7523(2)
_cell_length_b                   19.3159(7)
_cell_length_c                   8.7036(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.524(4)
_cell_angle_gamma                90
_cell_volume                     958.74(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(1)
_cell_measurement_reflns_used    3580
_cell_measurement_theta_min      3.1595
_cell_measurement_theta_max      34.7380

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Xcalibur diffractometer (Oxford Diffraction) with Sapphire3 detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_reflns_number            12273
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.166
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1955
_reflns_number_gt                1702
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0553P)²+0.2970P] 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_number_reflns         1955
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O1 O 0.47313(19) 0.12407(6) 0.48215(12) 0.0441(3) Uani 1 1 d . . . . .
O2 O 0.6753(2) 0.03538(7) 0.40096(15) 0.0590(4) Uani 1 1 d . . . . .
C1 C 0.2052(2) 0.00363(7) -0.06552(15) 0.0311(3) Uani 1 1 d . . . . .
H1 H 0.3427 0.0057 -0.1109 0.037 Uiso 1 1 calc R U . . .
C2 C 0.1487(2) 0.05815(7) 0.02741(15) 0.0292(3) Uani 1 1 d . . . . .
C3 C -0.0611(2) 0.05354(7) 0.09182(16) 0.0315(3) Uani 1 1 d . . . . .
H3 H -0.1043 0.0895 0.1533 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3083(2) 0.11900(7) 0.05423(16) 0.0312(3) Uani 1 1 d . . . . .
C5 C 0.3820(2) 0.14602(7) 0.20255(16) 0.0336(3) Uani 1 1 d . . . . .
C6 C 0.5365(3) 0.20203(8) 0.21784(19) 0.0432(4) Uani 1 1 d . . . . .
H6 H 0.5833 0.2206 0.3156 0.052 Uiso 1 1 calc R U . . .
C7 C 0.6212(3) 0.23047(8) 0.0907(2) 0.0493(4) Uani 1 1 d . . . . .
H7 H 0.7256 0.2674 0.1032 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5506(3) 0.20396(9) -0.0547(2) 0.0491(4) Uani 1 1 d . . . . .
H8 H 0.6068 0.2231 -0.1408 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3958(3) 0.14877(8) -0.07270(18) 0.0412(4) Uani 1 1 d . . . . .
H9 H 0.3492 0.1312 -0.1714 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3023(3) 0.11501(8) 0.34613(17) 0.0400(4) Uani 1 1 d . . . . .
H10A H 0.1559 0.1365 0.3641 0.048 Uiso 1 1 calc R U . . .
H10B H 0.2731 0.0660 0.3293 0.048 Uiso 1 1 calc R U . . .
C11 C 0.6550(3) 0.07952(8) 0.49512(18) 0.0424(4) Uani 1 1 d . . . . .
C12 C 0.8221(3) 0.09217(11) 0.6385(2) 0.0597(5) Uani 1 1 d . . . . .
H12A H 0.7551 0.0755 0.7269 0.089 Uiso 1 1 calc R U . . .
H12B H 0.8520 0.1409 0.6498 0.089 Uiso 1 1 calc R U . . .
H12C H 0.9665 0.0683 0.6311 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.3481(19) . ?
O1 C10 1.4470(17) . ?
O2 C11 1.1989(19) . ?
C1 C3 1.3818(19) 3 ?
C1 C2 1.3920(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.3985(18) . ?
C2 C4 1.4910(18) . ?
C3 C1 1.3817(19) 3 ?
C3 H3 0.9300 . ?
C4 C9 1.397(2) . ?
C4 C5 1.4054(19) . ?
C5 C6 1.396(2) . ?
C5 C10 1.510(2) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.492(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 115.34(12) . . ?
C3 C1 C2 121.35(12) 3 . ?
C3 C1 H1 119.3 3 . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 117.65(12) . . ?
C1 C2 C4 120.10(12) . . ?
C3 C2 C4 122.24(12) . . ?
C1 C3 C2 120.99(12) 3 . ?
C1 C3 H3 119.5 3 . ?
C2 C3 H3 119.5 . . ?
C9 C4 C5 118.50(12) . . ?
C9 C4 C2 118.63(12) . . ?
C5 C4 C2 122.81(12) . . ?
C6 C5 C4 119.15(13) . . ?
C6 C5 C10 119.16(13) . . ?
C4 C5 C10 121.68(12) . . ?
C7 C6 C5 121.29(15) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 119.77(14) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.89(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.38(15) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
O1 C10 C5 112.44(12) . . ?
O1 C10 H10A 109.1 . . ?
C5 C10 H10A 109.1 . . ?
O1 C10 H10B 109.1 . . ?
C5 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O2 C11 O1 122.74(15) . . ?
O2 C11 C12 125.35(16) . . ?
O1 C11 C12 111.91(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C3 C1 C2 C3 -0.9(2) 3 . . . ?
C3 C1 C2 C4 179.70(12) 3 . . . ?
C1 C2 C3 C1 0.9(2) . . . 3 ?
C4 C2 C3 C1 -179.72(12) . . . 3 ?
C1 C2 C4 C9 46.35(18) . . . . ?
C3 C2 C4 C9 -133.07(14) . . . . ?
C1 C2 C4 C5 -131.08(14) . . . . ?
C3 C2 C4 C5 49.51(18) . . . . ?
C9 C4 C5 C6 0.9(2) . . . . ?
C2 C4 C5 C6 178.35(12) . . . . ?
C9 C4 C5 C10 -177.73(13) . . . . ?
C2 C4 C5 C10 -0.3(2) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
C10 C5 C6 C7 177.54(14) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 0.0(2) . . . . ?
C5 C4 C9 C8 -0.4(2) . . . . ?
C2 C4 C9 C8 -177.92(13) . . . . ?
C11 O1 C10 C5 -79.14(16) . . . . ?
C6 C5 C10 O1 -27.83(18) . . . . ?
C4 C5 C10 O1 150.82(12) . . . . ?
C10 O1 C11 O2 0.1(2) . . . . ?
C10 O1 C11 C12 -179.74(13) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_ch15_pk252
_database_code_depnum_ccdc_archive 'CCDC 1971574'
loop_
_audit_author_name
_audit_author_address
'Joachim Kusz'
;University of Silesia, Katowice
Poland
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.9012(7)
_cell_length_b                   17.1124(8)
_cell_length_c                   7.6347(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.574(3)
_cell_angle_gamma                90
_cell_volume                     1551.84(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(1)
_cell_measurement_reflns_used    3739
_cell_measurement_theta_min      3.2585
_cell_measurement_theta_max      34.5939

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79006
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Xcalibur diffractometer (Oxford Diffraction) with Sapphire3 detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_reflns_number            22636
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.307
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3171
_reflns_number_gt                2477
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b 
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0604P)²+0.4077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O1 O 0.69481(14) 0.30626(9) 0.0877(2) 0.0689(5) Uani 1 1 d . . . . .
H1 H 0.711(2) 0.3185(16) -0.038(4) 0.103 Uiso 1 1 d . U . . .
C1 C 0.44197(18) 0.43222(11) 0.5254(2) 0.0530(5) Uani 1 1 d . . . . .
H1A H 0.4028 0.3863 0.5444 0.064 Uiso 1 1 calc R U . . .
C2 C 0.46641(15) 0.45210(10) 0.3559(2) 0.0405(4) Uani 1 1 d . . . . .
C3 C 0.52539(18) 0.52084(11) 0.3335(2) 0.0533(5) Uani 1 1 d . . . . .
H3 H 0.5433 0.5356 0.2214 0.064 Uiso 1 1 calc R U . . .
C4 C 0.42836(15) 0.40165(9) 0.2039(2) 0.0408(4) Uani 1 1 d . . . . .
C5 C 0.50476(16) 0.35981(10) 0.1086(2) 0.0445(4) Uani 1 1 d . . . . .
C6 C 0.46386(19) 0.31264(11) -0.0292(2) 0.0554(5) Uani 1 1 d . . . . .
H6 H 0.5143 0.2845 -0.0929 0.066 Uiso 1 1 calc R U . . .
C7 C 0.3507(2) 0.30666(12) -0.0732(3) 0.0598(6) Uani 1 1 d . . . . .
H7 H 0.3251 0.2750 -0.1663 0.072 Uiso 1 1 calc R U . . .
C8 C 0.27529(19) 0.34749(13) 0.0201(3) 0.0623(6) Uani 1 1 d . . . . .
H8 H 0.1985 0.3435 -0.0093 0.075 Uiso 1 1 calc R U . . .
C9 C 0.31398(17) 0.39464(11) 0.1583(3) 0.0535(5) Uani 1 1 d . . . . .
H9 H 0.2626 0.4221 0.2217 0.064 Uiso 1 1 calc R U . . .
C10 C 0.62940(18) 0.36614(14) 0.1560(3) 0.0684(6) Uani 1 1 d . . . . .
H10A H 0.6559 0.4159 0.1141 0.082 Uiso 1 1 calc R U . . .
H10B H 0.6412 0.3660 0.2829 0.082 Uiso 1 1 calc R U . . .
O11 O 0.73168(14) 0.33090(10) 0.7548(2) 0.0725(5) Uani 1 1 d . . . . .
H11 H 0.722(2) 0.2808(18) 0.679(4) 0.109 Uiso 1 1 d . U . . .
C11 C 1.04899(17) 0.52547(10) 0.8520(2) 0.0487(5) Uani 1 1 d . . . . .
H11A H 1.0828 0.5432 0.7528 0.058 Uiso 1 1 calc R U . . .
C12 C 0.99546(15) 0.45330(10) 0.8480(2) 0.0407(4) Uani 1 1 d . . . . .
C13 C 0.94715(17) 0.42854(11) 0.9986(2) 0.0494(5) Uani 1 1 d . . . . .
H13 H 0.9115 0.3802 0.9995 0.059 Uiso 1 1 calc R U . . .
C14 C 0.99586(15) 0.40264(10) 0.6884(2) 0.0407(4) Uani 1 1 d . . . . .
C15 C 0.89719(16) 0.37177(10) 0.6055(2) 0.0429(4) Uani 1 1 d . . . . .
C16 C 0.90603(19) 0.32159(11) 0.4629(2) 0.0525(5) Uani 1 1 d . . . . .
H16 H 0.8408 0.3008 0.4077 0.063 Uiso 1 1 calc R U . . .
C17 C 1.0082(2) 0.30218(11) 0.4020(3) 0.0601(6) Uani 1 1 d . . . . .
H17 H 1.0123 0.2673 0.3092 0.072 Uiso 1 1 calc R U . . .
C18 C 1.1047(2) 0.33470(12) 0.4790(3) 0.0619(6) Uani 1 1 d . . . . .
H18 H 1.1742 0.3229 0.4365 0.074 Uiso 1 1 calc R U . . .
C19 C 1.09809(18) 0.38504(11) 0.6203(3) 0.0534(5) Uani 1 1 d . . . . .
H19 H 1.1636 0.4075 0.6704 0.064 Uiso 1 1 calc R U . . .
C110 C 0.78134(17) 0.39200(12) 0.6603(3) 0.0541(5) Uani 1 1 d . . . . .
H11B H 0.7861 0.4385 0.7329 0.065 Uiso 1 1 calc R U . . .
H11C H 0.7332 0.4038 0.5565 0.065 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
O1 C10 1.407(2) . ?
O1 H1 1.01(3) . ?
C1 C3 1.380(3) 3_666 ?
C1 C2 1.386(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.386(2) . ?
C2 C4 1.494(2) . ?
C3 C1 1.380(3) 3_666 ?
C3 H3 0.9300 . ?
C4 C9 1.389(3) . ?
C4 C5 1.397(2) . ?
C5 C6 1.390(2) . ?
C5 C10 1.509(3) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O11 C110 1.420(2) . ?
O11 H11 1.03(3) . ?
C11 C13 1.384(2) 3_767 ?
C11 C12 1.389(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.384(2) . ?
C12 C14 1.496(2) . ?
C13 C11 1.384(2) 3_767 ?
C13 H13 0.9300 . ?
C14 C19 1.386(3) . ?
C14 C15 1.402(2) . ?
C15 C16 1.396(2) . ?
C15 C110 1.506(3) . ?
C16 C17 1.370(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C110 H11B 0.9700 . ?
C110 H11C 0.9700 . ?

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
C10 O1 H1 110.1(16) . . ?
C3 C1 C2 121.38(17) 3_666 . ?
C3 C1 H1A 119.3 3_666 . ?
C2 C1 H1A 119.3 . . ?
C1 C2 C3 117.44(16) . . ?
C1 C2 C4 120.82(16) . . ?
C3 C2 C4 121.74(15) . . ?
C1 C3 C2 121.19(17) 3_666 . ?
C1 C3 H3 119.4 3_666 . ?
C2 C3 H3 119.4 . . ?
C9 C4 C5 119.00(17) . . ?
C9 C4 C2 119.30(16) . . ?
C5 C4 C2 121.69(16) . . ?
C6 C5 C4 118.91(18) . . ?
C6 C5 C10 121.08(17) . . ?
C4 C5 C10 120.01(16) . . ?
C7 C6 C5 121.40(19) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.95(18) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.03(19) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
O1 C10 C5 114.66(18) . . ?
O1 C10 H10A 108.6 . . ?
C5 C10 H10A 108.6 . . ?
O1 C10 H10B 108.6 . . ?
C5 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C110 O11 H11 111.3(16) . . ?
C13 C11 C12 121.02(16) 3_767 . ?
C13 C11 H11A 119.5 3_767 . ?
C12 C11 H11A 119.5 . . ?
C13 C12 C11 117.88(16) . . ?
C13 C12 C14 121.48(15) . . ?
C11 C12 C14 120.56(15) . . ?
C11 C13 C12 121.10(16) 3_767 . ?
C11 C13 H13 119.4 3_767 . ?
C12 C13 H13 119.4 . . ?
C19 C14 C15 118.61(16) . . ?
C19 C14 C12 118.63(16) . . ?
C15 C14 C12 122.76(16) . . ?
C16 C15 C14 118.83(18) . . ?
C16 C15 C110 118.24(17) . . ?
C14 C15 C110 122.91(16) . . ?
C17 C16 C15 121.72(19) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 119.47(18) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 121.36(19) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
O11 C110 C15 112.91(16) . . ?
O11 C110 H11B 109.0 . . ?
C15 C110 H11B 109.0 . . ?
O11 C110 H11C 109.0 . . ?
C15 C110 H11C 109.0 . . ?
H11B C110 H11C 107.8 . . ?

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
C3 C1 C2 C3 0.3(3) 3_666 . . . ?
C3 C1 C2 C4 -178.64(18) 3_666 . . . ?
C1 C2 C3 C1 -0.3(3) . . . 3_666 ?
C4 C2 C3 C1 178.63(18) . . . 3_666 ?
C1 C2 C4 C9 66.6(2) . . . . ?
C3 C2 C4 C9 -112.3(2) . . . . ?
C1 C2 C4 C5 -111.9(2) . . . . ?
C3 C2 C4 C5 69.2(2) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C2 C4 C5 C6 178.69(16) . . . . ?
C9 C4 C5 C10 -179.72(19) . . . . ?
C2 C4 C5 C10 -1.2(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C10 C5 C6 C7 -179.9(2) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
C2 C4 C9 C8 -178.96(17) . . . . ?
C6 C5 C10 O1 -17.3(3) . . . . ?
C4 C5 C10 O1 162.63(18) . . . . ?
C13 C11 C12 C13 -0.6(3) 3_767 . . . ?
C13 C11 C12 C14 -177.48(17) 3_767 . . . ?
C11 C12 C13 C11 0.6(3) . . . 3_767 ?
C14 C12 C13 C11 177.45(17) . . . 3_767 ?
C13 C12 C14 C19 -123.7(2) . . . . ?
C11 C12 C14 C19 53.0(2) . . . . ?
C13 C12 C14 C15 55.9(2) . . . . ?
C11 C12 C14 C15 -127.39(19) . . . . ?
C19 C14 C15 C16 3.0(2) . . . . ?
C12 C14 C15 C16 -176.56(16) . . . . ?
C19 C14 C15 C110 -175.30(17) . . . . ?
C12 C14 C15 C110 5.1(2) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C110 C15 C16 C17 178.12(17) . . . . ?
C15 C16 C17 C18 -2.1(3) . . . . ?
C16 C17 C18 C19 1.7(3) . . . . ?
C15 C14 C19 C18 -3.4(3) . . . . ?
C12 C14 C19 C18 176.13(17) . . . . ?
C17 C18 C19 C14 1.1(3) . . . . ?
C16 C15 C110 O11 76.7(2) . . . . ?
C14 C15 C110 O11 -104.97(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O11 1.01(3) 1.63(3) 2.640(2) 175(3) 1_554
O11 H11 O1 1.03(3) 1.67(3) 2.694(2) 170(3) 4_566

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.029

_shelxl_version_number           2014/6

