# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1907870'
loop_
_audit_author_name
_audit_author_address
'Yandong Zhang'
;Xiamen University
China
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-03-22
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4465)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H18 O'
_chemical_formula_sum            'C16 H18 O'
_chemical_formula_weight         226.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   20.961(8)
_cell_length_b                   20.961(8)
_cell_length_c                   7.086(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2696.0(18)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    1221
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.24
_cell_measurement_theta_min      3.09
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.657438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0769 before and 0.0314 after correction.
The Ratio of minimum to maximum transmission is 0.6574.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1098
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5824
_diffrn_reflns_theta_full        29.10
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         1.94
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1930
_reflns_number_total             2880
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1846
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H15 of C15, H10 of C10, H12 of C12, H14 of C14, H13 of C13, {H9A,H9B} of C9,
   H4 of C4, {H7A,H7B} of C7, H6 of C6
 At 1.5 times of:
  {H17A,H17B,H17C} of C17, {H16A,H16B,H16C} of C16, H1 of O1
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33702(15) 0.37316(12) 0.2551(3) 0.0358(6) Uani 1 1 d . . .
H1 H 0.3329 0.3556 0.3609 0.054 Uiso 1 1 calc R . .
C2 C 0.39760(19) 0.56127(19) 0.3240(5) 0.0325(8) Uani 1 1 d . . .
C3 C 0.5288(2) 0.69969(19) 0.1789(6) 0.0383(9) Uani 1 1 d . . .
C4 C 0.5673(2) 0.6945(2) 0.4872(6) 0.0443(10) Uani 1 1 d . . .
H4 H 0.5563 0.6776 0.6108 0.053 Uiso 1 1 calc R . .
C5 C 0.5112(2) 0.67603(19) 0.3620(5) 0.0348(8) Uani 1 1 d . . .
C6 C 0.4131(2) 0.6148(2) 0.0141(5) 0.0404(9) Uani 1 1 d . . .
H6 H 0.3837 0.6083 -0.0906 0.048 Uiso 1 1 calc R . .
C7 C 0.4341(2) 0.63358(19) 0.4178(5) 0.0360(8) Uani 1 1 d . . .
H7A H 0.4092 0.6605 0.3843 0.043 Uiso 1 1 calc R . .
H7B H 0.4308 0.6267 0.5536 0.043 Uiso 1 1 calc R . .
C8 C 0.38876(18) 0.55519(19) 0.1414(5) 0.0340(8) Uani 1 1 d . . .
C9 C 0.3542(2) 0.47714(18) 0.0817(4) 0.0335(8) Uani 1 1 d . . .
H9A H 0.3894 0.4676 0.0170 0.040 Uiso 1 1 calc R . .
H9B H 0.3125 0.4639 -0.0006 0.040 Uiso 1 1 calc R . .
C10 C 0.3301(2) 0.4356(2) 0.2662(5) 0.0395(9) Uani 1 1 d . . .
H10 H 0.2779 0.4196 0.2850 0.047 Uiso 1 1 calc R . .
C11 C 0.37373(19) 0.49019(18) 0.4198(5) 0.0315(8) Uani 1 1 d . . .
C12 C 0.6014(2) 0.7435(2) 0.1308(7) 0.0508(11) Uani 1 1 d . . .
H12 H 0.6136 0.7609 0.0078 0.061 Uiso 1 1 calc R . .
C13 C 0.4735(2) 0.6782(2) 0.0314(5) 0.0405(9) Uani 1 1 d . . .
H13 H 0.4822 0.7134 -0.0602 0.049 Uiso 1 1 calc R . .
C14 C 0.6381(2) 0.7367(2) 0.4351(8) 0.0560(12) Uani 1 1 d . . .
H14 H 0.6755 0.7485 0.5225 0.067 Uiso 1 1 calc R . .
C15 C 0.6549(2) 0.7617(2) 0.2578(7) 0.0565(12) Uani 1 1 d . . .
H15 H 0.7039 0.7918 0.2230 0.068 Uiso 1 1 calc R . .
C16 C 0.4380(2) 0.4864(2) 0.4911(7) 0.0609(14) Uani 1 1 d . . .
H16A H 0.4683 0.4885 0.3868 0.091 Uiso 1 1 calc R . .
H16B H 0.4214 0.4410 0.5583 0.091 Uiso 1 1 calc R . .
H16C H 0.4662 0.5271 0.5743 0.091 Uiso 1 1 calc R . .
C17 C 0.3223(3) 0.4779(2) 0.5828(7) 0.0596(12) Uani 1 1 d . . .
H17A H 0.3482 0.5139 0.6791 0.089 Uiso 1 1 calc R . .
H17B H 0.3045 0.4294 0.6336 0.089 Uiso 1 1 calc R . .
H17C H 0.2814 0.4825 0.5391 0.089 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.390(4) . ?
C2 C7 1.472(5) . ?
C2 C8 1.304(4) . ?
C2 C11 1.478(5) . ?
C3 C5 1.372(5) . ?
C3 C12 1.369(5) . ?
C3 C13 1.455(5) . ?
C4 C5 1.365(5) . ?
C4 C14 1.345(6) . ?
C5 C7 1.457(5) . ?
C6 C8 1.414(5) . ?
C6 C13 1.304(5) . ?
C8 C9 1.482(5) . ?
C9 C10 1.510(5) . ?
C10 C11 1.511(5) . ?
C11 C16 1.478(5) . ?
C11 C17 1.511(6) . ?
C12 C15 1.337(6) . ?
C14 C15 1.339(6) . ?

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 C2 C11 124.8(3) . . ?
C8 C2 C7 121.6(3) . . ?
C8 C2 C11 113.4(3) . . ?
C5 C3 C13 122.6(3) . . ?
C12 C3 C5 119.0(4) . . ?
C12 C3 C13 118.3(4) . . ?
C14 C4 C5 121.3(4) . . ?
C3 C5 C7 119.6(3) . . ?
C4 C5 C3 118.3(4) . . ?
C4 C5 C7 122.1(3) . . ?
C13 C6 C8 125.3(4) . . ?
C5 C7 C2 110.7(3) . . ?
C2 C8 C6 125.2(3) . . ?
C2 C8 C9 111.0(3) . . ?
C6 C8 C9 123.7(3) . . ?
C8 C9 C10 103.1(3) . . ?
O1 C10 C9 109.4(3) . . ?
O1 C10 C11 116.4(3) . . ?
C9 C10 C11 106.6(3) . . ?
C2 C11 C10 101.7(3) . . ?
C2 C11 C17 112.1(3) . . ?
C10 C11 C17 108.1(3) . . ?
C16 C11 C2 110.7(3) . . ?
C16 C11 C10 115.3(3) . . ?
C16 C11 C17 108.8(4) . . ?
C15 C12 C3 121.1(4) . . ?
C6 C13 C3 126.9(3) . . ?
C15 C14 C4 120.2(4) . . ?
C12 C15 C14 120.1(4) . . ?

####################################################################### 
# 
# 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_mon
_database_code_depnum_ccdc_archive 'CCDC 1907871'
loop_
_audit_author_name
_audit_author_address
'Yandong Zhang'
;Xiamen University
China
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H33.99 O3 Si'
_chemical_formula_sum            'C27 H34 O3 Si'
_chemical_formula_weight         434.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   42.742(3)
_cell_length_b                   10.4771(9)
_cell_length_c                   10.9037(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.609(6)
_cell_angle_gamma                90
_cell_volume                     4873.1(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8614
_exptl_crystal_size_rad          0.0100
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10004
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.000
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3713
_reflns_number_total             4772
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0697
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0632P)²+3.5563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1574
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(C41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=1-FVAR(1)
 Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=
 Sof(H35)=Sof(C36)=Sof(H36)=FVAR(1)
 Fixed Sof: C21(0.4) H21A(0.4) H21B(0.4) H21C(0.4) C23(0.4) H23A(0.4)
 H23B(0.4) H23C(0.4) C1A(0.6) H1AA(0.6) H1AB(0.6) H1AC(0.6) C2A(0.6) H2AA(0.6)
 H2AB(0.6) H2AC(0.6) H43(0.5)
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C18(H18A,H18B)
3.c Me refined with riding coordinates:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C1A(H1AA,H1AB,
 H1AC), C2A(H2AA,H2AB,H2AC)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C7(H7), C9(H9), C14(H14), C17(H17), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C42(H42), C44(H44), C45(H45), C46(H46)
3.e Fitted hexagon refined as free rotating group:
 C31(C32,C33,C34,C35,C36), C41(C42,C43,C44,C45,C46)
3.f Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.08650(2) 0.76628(7) 0.09891(6) 0.0273(2) Uani 1 1 d . . . . .
O1 O 0.20557(4) 0.86517(19) 0.05625(15) 0.0385(5) Uani 1 1 d . . . . .
H1 H 0.1945 0.8954 0.1077 0.058 Uiso 1 1 calc R . . . .
O2 O 0.28797(4) 0.9096(2) -0.06432(19) 0.0510(6) Uani 1 1 d . . . . .
O3 O 0.10747(4) 0.7812(2) -0.02058(17) 0.0490(6) Uani 1 1 d . . . . .
C1 C 0.10758(6) 0.7601(3) 0.3561(2) 0.0357(6) Uani 1 1 d . . . . .
H1A H 0.0901 0.8101 0.3696 0.043 Uiso 1 1 calc R . . . .
C2 C 0.11352(6) 0.7264(3) 0.2362(2) 0.0324(6) Uani 1 1 d . . . . .
C3 C 0.26028(6) 0.9355(3) -0.0880(2) 0.0339(6) Uani 1 1 d . . . . .
C4 C 0.21040(6) 0.8324(3) -0.1645(2) 0.0332(6) Uani 1 1 d . . . . .
C5 C 0.24100(6) 0.8527(3) -0.1708(2) 0.0343(6) Uani 1 1 d . . . . .
H5 H 0.2510 0.8109 -0.2327 0.041 Uiso 1 1 calc R . . . .
C6 C 0.19110(5) 0.8861(3) -0.0640(2) 0.0318(6) Uani 1 1 d . . . . .
C7 C 0.12694(7) 0.7213(3) 0.4559(2) 0.0437(7) Uani 1 1 d . . . . .
H7 H 0.1225 0.7461 0.5348 0.052 Uiso 1 1 calc R . . . .
C8 C 0.05878(6) 0.6319(3) 0.0620(3) 0.0386(7) Uani 1 1 d . . . . .
C9 C 0.14023(6) 0.6531(3) 0.2209(3) 0.0439(7) Uani 1 1 d . . . . .
H9 H 0.1452 0.6305 0.1421 0.053 Uiso 1 1 calc R . . . .
C10 C 0.24677(6) 1.0567(3) -0.0389(3) 0.0393(7) Uani 1 1 d . . . . .
H10A H 0.2624 1.1235 -0.0417 0.047 Uiso 1 1 calc R . . . .
H10B H 0.2427 1.0434 0.0466 0.047 Uiso 1 1 calc R . . . .
C11 C 0.18695(6) 1.0312(3) -0.0785(3) 0.0362(6) Uani 1 1 d . . . . .
H11A H 0.1710 1.0473 -0.1441 0.043 Uiso 1 1 calc R . . . .
H11B H 0.1793 1.0653 -0.0033 0.043 Uiso 1 1 calc R . . . .
C12 C 0.15995(6) 0.8108(3) -0.0816(3) 0.0402(7) Uani 1 1 d . . . . .
H12 H 0.1636 0.7280 -0.0413 0.048 Uiso 1 1 calc R . . . .
C13 C 0.21671(6) 1.1032(3) -0.1070(3) 0.0383(7) Uani 1 1 d . . . . .
H13A H 0.2193 1.0972 -0.1946 0.046 Uiso 1 1 calc R . . . .
H13B H 0.2139 1.1926 -0.0876 0.046 Uiso 1 1 calc R . . . .
C14 C 0.15267(7) 0.6462(3) 0.4384(3) 0.0467(8) Uani 1 1 d . . . . .
H14 H 0.1653 0.6180 0.5055 0.056 Uiso 1 1 calc R . . . .
C15 C 0.15646(7) 0.7847(3) -0.2188(3) 0.0520(9) Uani 1 1 d . . . . .
H15A H 0.1489 0.8596 -0.2638 0.062 Uiso 1 1 calc R . . . .
H15B H 0.1422 0.7142 -0.2371 0.062 Uiso 1 1 calc R . . . .
C16 C 0.13275(6) 0.8701(3) -0.0236(3) 0.0468(8) Uani 1 1 d . . . . .
H16A H 0.1391 0.8968 0.0595 0.056 Uiso 1 1 calc R . . . .
H16B H 0.1259 0.9451 -0.0699 0.056 Uiso 1 1 calc R . . . .
C17 C 0.15954(7) 0.6132(3) 0.3211(3) 0.0504(8) Uani 1 1 d . . . . .
H17 H 0.1772 0.5640 0.3086 0.060 Uiso 1 1 calc R . . . .
C18 C 0.18984(7) 0.7507(3) -0.2497(3) 0.0489(8) Uani 1 1 d . . . . .
H18A H 0.1940 0.6608 -0.2352 0.059 Uiso 1 1 calc R . . . .
H18B H 0.1931 0.7702 -0.3349 0.059 Uiso 1 1 calc R . . . .
C19 C 0.04001(9) 0.6556(4) -0.0600(3) 0.0740(11) Uani 1 1 d . . . . .
H19A H 0.0538 0.6849 -0.1200 0.111 Uiso 1 1 calc R . . . .
H19B H 0.0301 0.5777 -0.0878 0.111 Uiso 1 1 calc R . . . .
H19C H 0.0243 0.7192 -0.0485 0.111 Uiso 1 1 calc R . . . .
C21 C 0.0335(2) 0.6594(9) 0.1732(10) 0.052(3) Uani 0.4 1 d . . P A 1
H21A H 0.0229 0.7390 0.1574 0.078 Uiso 0.4 1 calc R . P A 1
H21B H 0.0184 0.5915 0.1734 0.078 Uiso 0.4 1 calc R . P A 1
H21C H 0.0449 0.6631 0.2518 0.078 Uiso 0.4 1 calc R . P A 1
C23 C 0.0729(2) 0.5073(9) 0.1000(11) 0.061(3) Uani 0.4 1 d . . P A 1
H23A H 0.0835 0.5157 0.1799 0.091 Uiso 0.4 1 calc R . P A 1
H23B H 0.0567 0.4441 0.1029 0.091 Uiso 0.4 1 calc R . P A 1
H23C H 0.0877 0.4817 0.0418 0.091 Uiso 0.4 1 calc R . P A 1
C1A C 0.03774(16) 0.5885(8) 0.1499(7) 0.0662(19) Uani 0.6 1 d . . P A 2
H1AA H 0.0492 0.5731 0.2271 0.099 Uiso 0.6 1 calc R . P A 2
H1AB H 0.0220 0.6523 0.1605 0.099 Uiso 0.6 1 calc R . P A 2
H1AC H 0.0279 0.5108 0.1212 0.099 Uiso 0.6 1 calc R . P A 2
C2A C 0.08003(14) 0.5128(5) 0.0205(6) 0.0487(14) Uani 0.6 1 d . . P A 2
H2AA H 0.0942 0.5416 -0.0386 0.073 Uiso 0.6 1 calc R . P A 2
H2AB H 0.0918 0.4791 0.0911 0.073 Uiso 0.6 1 calc R . P A 2
H2AC H 0.0667 0.4475 -0.0156 0.073 Uiso 0.6 1 calc R . P A 2
C31 C 0.06986(7) 0.9370(2) 0.0943(3) 0.0212(11) Uani 0.492(3) 1 d . . P B 1
C32 C 0.07992(7) 1.0241(3) 0.1845(3) 0.0328(13) Uani 0.492(3) 1 d G . P B 1
H32 H 0.0948 1.0000 0.2462 0.039 Uiso 0.492(3) 1 calc R . P B 1
C33 C 0.06781(8) 1.1473(3) 0.1824(3) 0.0375(14) Uani 0.492(3) 1 d G . P B 1
H33 H 0.0745 1.2056 0.2428 0.045 Uiso 0.492(3) 1 calc R . P B 1
C34 C 0.04564(9) 1.1833(3) 0.0902(3) 0.0397(17) Uani 0.492(3) 1 d G . P B 1
H34 H 0.0375 1.2657 0.0888 0.048 Uiso 0.492(3) 1 calc R . P B 1
C35 C 0.03558(7) 1.0962(3) 0.0000(3) 0.0370(14) Uani 0.492(3) 1 d G . P B 1
H35 H 0.0207 1.1203 -0.0617 0.044 Uiso 0.492(3) 1 calc R . P B 1
C36 C 0.04768(7) 0.9730(3) 0.0021(3) 0.0306(12) Uani 0.492(3) 1 d G . P B 1
H36 H 0.0409 0.9147 -0.0582 0.037 Uiso 0.492(3) 1 calc R . P B 1
C41 C 0.06023(8) 0.9046(3) 0.1481(3) 0.0295(12) Uani 0.508(3) 1 d . . P B 2
C42 C 0.04017(8) 0.8993(3) 0.2434(3) 0.0386(14) Uani 0.508(3) 1 d G . P B 2
H42 H 0.0393 0.8260 0.2912 0.046 Uiso 0.508(3) 1 calc R . P B 2
C43 C 0.02140(8) 1.0036(4) 0.2674(3) 0.0467(16) Uani 0.508(3) 1 d G . P B 2
C44 C 0.02270(9) 1.1132(3) 0.1960(4) 0.0484(17) Uani 0.508(3) 1 d G . P B 2
H44 H 0.0101 1.1829 0.2121 0.058 Uiso 0.508(3) 1 calc R . P B 2
C45 C 0.04276(10) 1.1184(3) 0.1007(4) 0.053(2) Uani 0.508(3) 1 d G . P B 2
H45 H 0.0436 1.1918 0.0529 0.064 Uiso 0.508(3) 1 calc R . P B 2
C46 C 0.06153(9) 1.0142(4) 0.0767(3) 0.0435(16) Uani 0.508(3) 1 d G . P B 2
H46 H 0.0750 1.0177 0.0129 0.052 Uiso 0.508(3) 1 calc R . P B 2
H43 H 0.0073(14) 1.004(7) 0.328(5) 0.057(18) Uiso 0.5 1 d . . P C 2


_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
Si1 O3 1.635(2) . ?
Si1 C2 1.879(3) . ?
Si1 C8 1.868(3) . ?
Si1 C31 1.924(3) . ?
Si1 C41 1.930(3) . ?
O1 C6 1.431(3) . ?
O2 C3 1.225(3) . ?
O3 C16 1.428(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.385(4) . ?
C2 C9 1.394(4) . ?
C3 C5 1.468(4) . ?
C3 C10 1.507(4) . ?
C4 C5 1.331(4) . ?
C4 C6 1.521(4) . ?
C4 C18 1.506(4) . ?
C6 C11 1.538(4) . ?
C6 C12 1.549(3) . ?
C7 C14 1.375(4) . ?
C8 C19 1.529(4) . ?
C8 C21 1.699(9) . ?
C8 C23 1.487(10) . ?
C8 C1A 1.430(7) . ?
C8 C2A 1.624(6) . ?
C9 C17 1.391(4) . ?
C10 C13 1.523(4) . ?
C11 C13 1.527(3) . ?
C12 C15 1.519(4) . ?
C12 C16 1.494(4) . ?
C14 C17 1.375(4) . ?
C15 C18 1.528(4) . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
C35 C36 1.3900 . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C42 C43 1.3900 . ?
C43 C43 1.845(7) 2 ?
C43 C44 1.3900 . ?
C44 C45 1.3900 . ?
C45 C46 1.3900 . ?

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
O3 Si1 C2 108.41(10) . . ?
O3 Si1 C8 105.82(12) . . ?
O3 Si1 C31 96.35(14) . . ?
O3 Si1 C41 120.48(14) . . ?
C2 Si1 C31 115.80(12) . . ?
C2 Si1 C41 106.56(13) . . ?
C8 Si1 C2 110.72(12) . . ?
C8 Si1 C31 117.80(13) . . ?
C8 Si1 C41 104.69(14) . . ?
C16 O3 Si1 122.28(19) . . ?
C7 C1 C2 121.8(3) . . ?
C1 C2 Si1 123.5(2) . . ?
C1 C2 C9 116.8(2) . . ?
C9 C2 Si1 119.63(19) . . ?
O2 C3 C5 119.7(3) . . ?
O2 C3 C10 119.9(2) . . ?
C5 C3 C10 120.2(2) . . ?
C5 C4 C6 123.9(2) . . ?
C5 C4 C18 126.6(3) . . ?
C18 C4 C6 109.5(2) . . ?
C4 C5 C3 125.3(2) . . ?
O1 C6 C4 112.37(19) . . ?
O1 C6 C11 106.7(2) . . ?
O1 C6 C12 110.7(2) . . ?
C4 C6 C11 110.8(2) . . ?
C4 C6 C12 102.9(2) . . ?
C11 C6 C12 113.5(2) . . ?
C14 C7 C1 120.2(3) . . ?
C19 C8 Si1 110.9(2) . . ?
C19 C8 C21 105.7(4) . . ?
C19 C8 C2A 98.9(3) . . ?
C21 C8 Si1 98.1(3) . . ?
C23 C8 Si1 111.1(4) . . ?
C23 C8 C19 124.6(5) . . ?
C23 C8 C21 102.4(6) . . ?
C1A C8 Si1 120.8(4) . . ?
C1A C8 C19 108.5(4) . . ?
C1A C8 C2A 109.2(4) . . ?
C2A C8 Si1 106.3(3) . . ?
C17 C9 C2 121.5(3) . . ?
C3 C10 C13 115.3(2) . . ?
C13 C11 C6 114.6(2) . . ?
C15 C12 C6 104.1(2) . . ?
C16 C12 C6 114.9(2) . . ?
C16 C12 C15 117.5(2) . . ?
C10 C13 C11 115.5(2) . . ?
C17 C14 C7 119.5(3) . . ?
C12 C15 C18 102.9(2) . . ?
O3 C16 C12 110.4(3) . . ?
C14 C17 C9 120.3(3) . . ?
C4 C18 C15 104.4(2) . . ?
C32 C31 Si1 119.65(17) . . ?
C32 C31 C36 120.0 . . ?
C36 C31 Si1 120.35(17) . . ?
C31 C32 C33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C33 C34 C35 120.0 . . ?
C36 C35 C34 120.0 . . ?
C35 C36 C31 120.0 . . ?
C42 C41 Si1 125.1(2) . . ?
C42 C41 C46 120.0 . . ?
C46 C41 Si1 114.85(19) . . ?
C41 C42 C43 120.0 . . ?
C42 C43 C43 122.53(14) . 2 ?
C44 C43 C42 120.0 . . ?
C44 C43 C43 87.6(2) . 2 ?
C43 C44 C45 120.0 . . ?
C46 C45 C44 120.0 . . ?
C45 C46 C41 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lmg
_database_code_depnum_ccdc_archive 'CCDC 1907872'
loop_
_audit_author_name
_audit_author_address
'Yandong Zhang'
;Xiamen University
China
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 O5'
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_weight         266.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3423(10)
_cell_length_b                   8.4321(9)
_cell_length_c                   10.4623(11)
_cell_angle_alpha                85.681(8)
_cell_angle_beta                 85.985(10)
_cell_angle_gamma                78.332(10)
_cell_volume                     631.54(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    185.1(6)
_cell_measurement_theta_max      29.1980
_cell_measurement_theta_min      3.8970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.054
_diffrn_ambient_temperature      185.1(6)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00    1.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060  -57.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega  -93.00    8.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060  -77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   48.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   57.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   46.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   38.0000  150.0000 63

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00   65.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -       24.2560  -99.0000   90.0000 69
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0335180000
_diffrn_orient_matrix_UB_12      -0.0126857000
_diffrn_orient_matrix_UB_13      0.0626563000
_diffrn_orient_matrix_UB_21      0.0897893000
_diffrn_orient_matrix_UB_22      0.0086136000
_diffrn_orient_matrix_UB_23      -0.0255477000
_diffrn_orient_matrix_UB_31      -0.0239938000
_diffrn_orient_matrix_UB_32      0.0846859000
_diffrn_orient_matrix_UB_33      0.0076529000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2463
_reflns_number_total             2890
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.2299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00D(H00F,H00G), C00E(H00H,H00I), C00F(H00J,H00K), C00G(H00L,
 H00M), C00H(H00N,H00O), C00J(H00P,H00Q)
2.c Idealised Me refined as rotating group:
 C00C(H00C,H00D,H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O -0.43717(13) -0.14286(11) -0.20772(8) 0.0204(2) Uani 1 1 d . . . . .
O002 O 0.04685(14) -0.37572(12) -0.41206(10) 0.0269(2) Uani 1 1 d . . . . .
O003 O -0.59848(16) 0.02813(14) -0.35512(10) 0.0369(3) Uani 1 1 d . . . . .
O004 O 0.05947(15) -0.58140(13) -0.26979(11) 0.0336(3) Uani 1 1 d . . . . .
O005 O -0.3054(2) -0.70582(17) -0.05948(15) 0.0597(4) Uani 1 1 d . . . . .
C006 C -0.30675(18) -0.23203(15) -0.30212(12) 0.0175(3) Uani 1 1 d . . . . .
C007 C -0.16189(18) -0.34141(15) -0.21681(12) 0.0188(3) Uani 1 1 d . . . . .
C008 C -0.57175(19) -0.01716(16) -0.24524(13) 0.0214(3) Uani 1 1 d . . . . .
C009 C -0.18380(19) -0.12137(16) -0.37133(13) 0.0213(3) Uani 1 1 d . . . . .
H009 H -0.2599 -0.0263 -0.4148 0.026 Uiso 1 1 calc R . . . .
C00A C -0.01421(19) -0.44465(17) -0.30123(13) 0.0225(3) Uani 1 1 d . . . . .
C00B C -0.40778(19) -0.32021(17) -0.38780(13) 0.0226(3) Uani 1 1 d . . . . .
H00A H -0.3168 -0.3793 -0.4477 0.027 Uiso 1 1 calc R . . . .
H00B H -0.4931 -0.2400 -0.4375 0.027 Uiso 1 1 calc R . . . .
C00C C -0.6797(2) 0.05727(17) -0.13076(14) 0.0266(3) Uani 1 1 d . . . . .
H00C H -0.6001 0.1056 -0.0832 0.040 Uiso 1 1 calc GR . . . .
H00D H -0.7256 -0.0251 -0.0770 0.040 Uiso 1 1 calc GR . . . .
H00E H -0.7827 0.1391 -0.1586 0.040 Uiso 1 1 calc GR . . . .
C00D C -0.2394(2) -0.44548(17) -0.10822(14) 0.0259(3) Uani 1 1 d . . . . .
H00F H -0.1422 -0.4815 -0.0483 0.031 Uiso 1 1 calc R . . . .
H00G H -0.3406 -0.3753 -0.0631 0.031 Uiso 1 1 calc R . . . .
C00E C -0.0819(2) -0.07115(18) -0.26222(14) 0.0279(3) Uani 1 1 d . . . . .
H00H H -0.1538 0.0260 -0.2255 0.033 Uiso 1 1 calc R . . . .
H00I H 0.0394 -0.0508 -0.2932 0.033 Uiso 1 1 calc R . . . .
C00F C -0.0621(2) -0.21657(17) -0.16239(13) 0.0243(3) Uani 1 1 d . . . . .
H00J H -0.1204 -0.1831 -0.0801 0.029 Uiso 1 1 calc R . . . .
H00K H 0.0683 -0.2635 -0.1514 0.029 Uiso 1 1 calc R . . . .
C00G C -0.5170(2) -0.43870(19) -0.31644(16) 0.0299(3) Uani 1 1 d . . . . .
H00L H -0.6042 -0.4637 -0.3738 0.036 Uiso 1 1 calc R . . . .
H00M H -0.5891 -0.3858 -0.2447 0.036 Uiso 1 1 calc R . . . .
C00H C -0.0500(2) -0.21924(18) -0.46630(14) 0.0264(3) Uani 1 1 d . . . . .
H00N H -0.1185 -0.2376 -0.5379 0.032 Uiso 1 1 calc R . . . .
H00O H 0.0418 -0.1562 -0.4995 0.032 Uiso 1 1 calc R . . . .
C00I C -0.3106(2) -0.59336(19) -0.13968(17) 0.0336(4) Uani 1 1 d . . . . .
C00J C -0.3963(3) -0.59836(19) -0.26543(18) 0.0382(4) Uani 1 1 d . . . . .
H00P H -0.4723 -0.6806 -0.2559 0.046 Uiso 1 1 calc R . . . .
H00Q H -0.2968 -0.6323 -0.3295 0.046 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.4649(15) . ?
O001 C008 1.3498(16) . ?
O002 C00A 1.3469(17) . ?
O002 C00H 1.4604(17) . ?
O003 C008 1.2005(17) . ?
O004 C00A 1.2024(17) . ?
O005 C00I 1.2143(19) . ?
C006 C007 1.5462(17) . ?
C006 C009 1.5353(18) . ?
C006 C00B 1.5242(18) . ?
C007 C00A 1.5211(19) . ?
C007 C00D 1.5318(18) . ?
C007 C00F 1.5590(19) . ?
C008 C00C 1.4952(19) . ?
C009 H009 0.9800 . ?
C009 C00E 1.5370(19) . ?
C009 C00H 1.514(2) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00B C00G 1.526(2) . ?
C00C H00C 0.9600 . ?
C00C H00D 0.9600 . ?
C00C H00E 0.9600 . ?
C00D H00F 0.9700 . ?
C00D H00G 0.9700 . ?
C00D C00I 1.512(2) . ?
C00E H00H 0.9700 . ?
C00E H00I 0.9700 . ?
C00E C00F 1.540(2) . ?
C00F H00J 0.9700 . ?
C00F H00K 0.9700 . ?
C00G H00L 0.9700 . ?
C00G H00M 0.9700 . ?
C00G C00J 1.536(2) . ?
C00H H00N 0.9700 . ?
C00H H00O 0.9700 . ?
C00I C00J 1.504(2) . ?
C00J H00P 0.9700 . ?
C00J H00Q 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
C008 O001 C006 120.87(10) . . ?
C00A O002 C00H 121.99(11) . . ?
O001 C006 C007 102.61(10) . . ?
O001 C006 C009 110.35(10) . . ?
O001 C006 C00B 110.99(10) . . ?
C009 C006 C007 99.67(10) . . ?
C00B C006 C007 115.80(11) . . ?
C00B C006 C009 116.16(11) . . ?
C006 C007 C00F 102.61(10) . . ?
C00A C007 C006 109.45(10) . . ?
C00A C007 C00D 111.23(11) . . ?
C00A C007 C00F 105.46(11) . . ?
C00D C007 C006 116.22(11) . . ?
C00D C007 C00F 111.04(11) . . ?
O001 C008 C00C 110.27(11) . . ?
O003 C008 O001 124.31(13) . . ?
O003 C008 C00C 125.42(13) . . ?
C006 C009 H009 110.9 . . ?
C006 C009 C00E 103.57(11) . . ?
C00E C009 H009 110.9 . . ?
C00H C009 C006 108.40(11) . . ?
C00H C009 H009 110.9 . . ?
C00H C009 C00E 111.84(12) . . ?
O002 C00A C007 118.40(11) . . ?
O004 C00A O002 118.33(13) . . ?
O004 C00A C007 123.08(13) . . ?
C006 C00B H00A 108.6 . . ?
C006 C00B H00B 108.6 . . ?
C006 C00B C00G 114.83(12) . . ?
H00A C00B H00B 107.5 . . ?
C00G C00B H00A 108.6 . . ?
C00G C00B H00B 108.6 . . ?
C008 C00C H00C 109.5 . . ?
C008 C00C H00D 109.5 . . ?
C008 C00C H00E 109.5 . . ?
H00C C00C H00D 109.5 . . ?
H00C C00C H00E 109.5 . . ?
H00D C00C H00E 109.5 . . ?
C007 C00D H00F 107.4 . . ?
C007 C00D H00G 107.4 . . ?
H00F C00D H00G 107.0 . . ?
C00I C00D C007 119.51(13) . . ?
C00I C00D H00F 107.4 . . ?
C00I C00D H00G 107.4 . . ?
C009 C00E H00H 110.8 . . ?
C009 C00E H00I 110.8 . . ?
C009 C00E C00F 104.77(11) . . ?
H00H C00E H00I 108.9 . . ?
C00F C00E H00H 110.8 . . ?
C00F C00E H00I 110.8 . . ?
C007 C00F H00J 110.6 . . ?
C007 C00F H00K 110.6 . . ?
C00E C00F C007 105.72(11) . . ?
C00E C00F H00J 110.6 . . ?
C00E C00F H00K 110.6 . . ?
H00J C00F H00K 108.7 . . ?
C00B C00G H00L 108.6 . . ?
C00B C00G H00M 108.6 . . ?
C00B C00G C00J 114.52(13) . . ?
H00L C00G H00M 107.6 . . ?
C00J C00G H00L 108.6 . . ?
C00J C00G H00M 108.6 . . ?
O002 C00H C009 113.90(11) . . ?
O002 C00H H00N 108.8 . . ?
O002 C00H H00O 108.8 . . ?
C009 C00H H00N 108.8 . . ?
C009 C00H H00O 108.8 . . ?
H00N C00H H00O 107.7 . . ?
O005 C00I C00D 118.98(16) . . ?
O005 C00I C00J 120.14(16) . . ?
C00J C00I C00D 120.80(12) . . ?
C00G C00J H00P 108.3 . . ?
C00G C00J H00Q 108.3 . . ?
C00I C00J C00G 116.00(14) . . ?
C00I C00J H00P 108.3 . . ?
C00I C00J H00Q 108.3 . . ?
H00P C00J H00Q 107.4 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
