# 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_p21c_2
_database_code_depnum_ccdc_archive 'CCDC 2003840'
loop_
_audit_author_name
_audit_author_address
'toyoharu kobayashi'
;Tokyo University of Pharmacy and Life Sciences
Japan
;
#Added by publCIF
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-03-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_publcif_datablock.id            {bfd269a6-aa82-4fe0-8157-bb85ba00bbfc}
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H28 O4'
_chemical_formula_sum            'C17 H28 O4'
_chemical_formula_weight         296.39
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2304(14)
_cell_length_b                   9.1246(8)
_cell_length_c                   22.238(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.6270(10)
_cell_angle_gamma                90
_cell_volume                     3075.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.9303.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.1420
1.00 0.00 -1.00 0.1010
1.00 1.00 2.00 0.1060
-3.00 -2.00 -3.00 0.1110
1.00 -1.00 2.00 0.1330
-1.00 1.00 -2.00 0.0870
-1.00 0.00 -2.00 0.0580
1.00 0.00 2.00 0.0490
-1.00 0.00 -4.00 0.0610
1.00 -1.00 -4.00 0.1250
-4.00 -4.00 -3.00 0.1180
-2.00 1.00 4.00 0.1580
3.00 2.00 -2.00 0.1400
1.00 0.00 -3.00 0.0890
2.00 -2.00 -3.00 0.1560
-4.00 -4.00 3.00 0.1600
-2.00 2.00 1.00 0.1240
0.00 3.00 -2.00 0.1220
-4.00 0.00 1.00 0.1280
2.00 -1.00 -4.00 0.1210

_exptl_crystal_recrystallization_method 
'slow crystallization from a  hexane solution at room temperature'
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.117
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.468
_diffrn_reflns_theta_min         1.343
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5308
_reflns_number_total             6332
_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_data_collection       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Platon (A.L.Spek, 2003)
Olex2 1.3-alpha (Dolomanov et al., 2009)
;
_computing_publication_material  
;
Olex2 1.3-alpha (Dolomanov et al., 2009)
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6332
_refine_ls_number_restraints     528
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.030
_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)+(0.0839P)²+1.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1432
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.002 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.5 and sigma
for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C4S(H4S), C7S(H7S)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,
 H13B), C16(H16A,H16B), C2S(H2SA,H2SB), C5S(H5SA,H5SB), C6S(H6SA,H6SB),
 C9S(H9SA,H9SB), C10S(H10C,H10D), C13S(H13C,H13D), C16S(H16C,H16D)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C14S(H14S)
3.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C15S(H15C,H15D)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C12S(H12D,H12E,H12F), C17S(H17D,
 H17E,H17F)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4A), O2S(H2S), O3S(H3S), O4S(H4SA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.68725(9) 0.74528(15) 0.76622(6) 0.0105(3) Uani 1 1 d . U . . .
C2 C 0.59702(9) 0.80644(16) 0.73930(6) 0.0111(3) Uani 1 1 d . U . . .
H2A H 0.591332 0.911289 0.749680 0.013 Uiso 1 1 calc R U . . .
H2B H 0.548021 0.751444 0.754909 0.013 Uiso 1 1 calc R U . . .
C3 C 0.59574(9) 0.78641(16) 0.66982(6) 0.0101(3) Uani 1 1 d . U . . .
C4 C 0.57169(9) 0.92432(16) 0.63177(6) 0.0119(3) Uani 1 1 d . U . . .
H4 H 0.509299 0.950078 0.637696 0.014 Uiso 1 1 calc R U . . .
C5 C 0.57524(10) 0.89312(17) 0.56405(6) 0.0145(3) Uani 1 1 d . U . . .
H5A H 0.554912 0.981125 0.540640 0.017 Uiso 1 1 calc R U . . .
H5B H 0.637185 0.874216 0.556425 0.017 Uiso 1 1 calc R U . . .
C6 C 0.51848(10) 0.76200(17) 0.54163(7) 0.0160(3) Uani 1 1 d . U . . .
H6A H 0.455479 0.785257 0.544246 0.019 Uiso 1 1 calc R U . . .
H6B H 0.526700 0.742572 0.498747 0.019 Uiso 1 1 calc R U . . .
C7 C 0.54344(9) 0.62519(17) 0.57929(7) 0.0133(3) Uani 1 1 d . U . . .
H7 H 0.500436 0.546081 0.565950 0.016 Uiso 1 1 calc R U . . .
C8 C 0.53807(9) 0.65138(16) 0.64776(6) 0.0115(3) Uani 1 1 d . U . . .
C9 C 0.57152(9) 0.51645(16) 0.68591(6) 0.0127(3) Uani 1 1 d . U . . .
H9A H 0.544068 0.518309 0.724451 0.015 Uiso 1 1 calc R U . . .
H9B H 0.550800 0.426586 0.663949 0.015 Uiso 1 1 calc R U . . .
C10 C 0.67210(9) 0.50611(15) 0.70044(6) 0.0113(3) Uani 1 1 d . U . . .
H10A H 0.685263 0.443301 0.736499 0.014 Uiso 1 1 calc R U . . .
H10B H 0.697670 0.458338 0.666186 0.014 Uiso 1 1 calc R U . . .
C11 C 0.71635(9) 0.65511(15) 0.71230(6) 0.0103(3) Uani 1 1 d . U . . .
C12 C 0.75255(10) 0.87219(16) 0.78002(7) 0.0143(3) Uani 1 1 d . U . . .
H12A H 0.758256 0.928115 0.742984 0.021 Uiso 1 1 calc R U . . .
H12B H 0.810280 0.832714 0.795357 0.021 Uiso 1 1 calc R U . . .
H12C H 0.730722 0.936625 0.810520 0.021 Uiso 1 1 calc R U . . .
C13 C 0.68149(10) 0.65227(16) 0.82351(6) 0.0140(3) Uani 1 1 d . U . . .
H13A H 0.643660 0.565938 0.813081 0.017 Uiso 1 1 calc R U . . .
H13B H 0.741197 0.616030 0.837757 0.017 Uiso 1 1 calc R U . . .
C14 C 0.64476(10) 0.73521(17) 0.87428(7) 0.0156(3) Uani 1 1 d . U . . .
H14 H 0.583307 0.755705 0.870247 0.019 Uiso 1 1 calc R U . . .
C15 C 0.69168(11) 0.78154(19) 0.92399(7) 0.0198(3) Uani 1 1 d . U . . .
H15A H 0.753331 0.763170 0.929683 0.024 Uiso 1 1 calc R U . . .
H15B H 0.663661 0.833117 0.953923 0.024 Uiso 1 1 calc R U . . .
C16 C 0.62865(10) 1.05816(16) 0.65038(7) 0.0153(3) Uani 1 1 d . U . . .
H16A H 0.630681 1.072364 0.694625 0.018 Uiso 1 1 calc R U . . .
H16B H 0.689658 1.041452 0.640118 0.018 Uiso 1 1 calc R U . . .
C17 C 0.44001(9) 0.67306(17) 0.65713(7) 0.0147(3) Uani 1 1 d . U . . .
H17A H 0.434117 0.688647 0.700151 0.022 Uiso 1 1 calc R U . . .
H17B H 0.406553 0.585720 0.643144 0.022 Uiso 1 1 calc R U . . .
H17C H 0.416976 0.758611 0.634053 0.022 Uiso 1 1 calc R U . . .
O1 O 0.68722(6) 0.74801(11) 0.66127(4) 0.0093(2) Uani 1 1 d . U . . .
O2 O 0.59345(8) 1.18664(12) 0.62008(5) 0.0207(3) Uani 1 1 d . U . . .
H2 H 0.626549 1.212428 0.593915 0.031 Uiso 1 1 calc R U . . .
O3 O 0.63018(7) 0.57710(12) 0.56635(5) 0.0140(2) Uani 1 1 d . U . . .
H3 H 0.668719 0.630326 0.585058 0.021 Uiso 1 1 calc R U . . .
O4 O 0.80825(6) 0.64421(11) 0.71504(5) 0.0120(2) Uani 1 1 d . U . . .
H4A H 0.822147 0.561626 0.702231 0.018 Uiso 1 1 calc R U . . .
C1S C 0.81541(9) 0.22171(16) 0.48028(6) 0.0103(3) Uani 1 1 d . U . . .
C2S C 0.90497(9) 0.15702(16) 0.50718(6) 0.0110(3) Uani 1 1 d . U . . .
H2SA H 0.954744 0.212198 0.492676 0.013 Uiso 1 1 calc R U . . .
H2SB H 0.910036 0.052811 0.495612 0.013 Uiso 1 1 calc R U . . .
C3S C 0.90494(9) 0.17246(15) 0.57686(6) 0.0092(3) Uani 1 1 d . U . . .
C4S C 0.92889(9) 0.03319(16) 0.61386(6) 0.0111(3) Uani 1 1 d . U . . .
H4S H 0.990864 0.006563 0.607131 0.013 Uiso 1 1 calc R U . . .
C5S C 0.92672(10) 0.06048(17) 0.68194(6) 0.0146(3) Uani 1 1 d . U . . .
H5SA H 0.864885 0.077277 0.690360 0.018 Uiso 1 1 calc R U . . .
H5SB H 0.948145 -0.028423 0.704301 0.018 Uiso 1 1 calc R U . . .
C6S C 0.98275(10) 0.19147(17) 0.70532(6) 0.0149(3) Uani 1 1 d . U . . .
H6SA H 1.045842 0.169855 0.702221 0.018 Uiso 1 1 calc R U . . .
H6SB H 0.974804 0.208325 0.748433 0.018 Uiso 1 1 calc R U . . .
C7S C 0.95636(9) 0.32957(16) 0.66893(6) 0.0122(3) Uani 1 1 d . U . . .
H7S H 0.998748 0.409078 0.682881 0.015 Uiso 1 1 calc R U . . .
C8S C 0.96189(9) 0.30720(16) 0.60042(6) 0.0103(3) Uani 1 1 d . U . . .
C9S C 0.92779(9) 0.44431(16) 0.56400(6) 0.0115(3) Uani 1 1 d . U . . .
H9SA H 0.948163 0.532799 0.587064 0.014 Uiso 1 1 calc R U . . .
H9SB H 0.955242 0.445841 0.525448 0.014 Uiso 1 1 calc R U . . .
C10S C 0.82730(9) 0.45429(15) 0.54957(6) 0.0102(3) Uani 1 1 d . U . . .
H10C H 0.801371 0.497732 0.584598 0.012 Uiso 1 1 calc R U . . .
H10D H 0.813833 0.520501 0.514615 0.012 Uiso 1 1 calc R U . . .
C11S C 0.78423(9) 0.30505(15) 0.53508(6) 0.0098(3) Uani 1 1 d . U . . .
C12S C 0.75105(10) 0.09636(16) 0.46198(7) 0.0147(3) Uani 1 1 d . U . . .
H12D H 0.775713 0.034468 0.431788 0.022 Uiso 1 1 calc R U . . .
H12E H 0.694554 0.137198 0.444834 0.022 Uiso 1 1 calc R U . . .
H12F H 0.741801 0.037386 0.497650 0.022 Uiso 1 1 calc R U . . .
C13S C 0.82312(10) 0.32492(16) 0.42600(6) 0.0137(3) Uani 1 1 d . U . . .
H13C H 0.764374 0.367765 0.413715 0.016 Uiso 1 1 calc R U . . .
H13D H 0.863465 0.406407 0.439096 0.016 Uiso 1 1 calc R U . . .
C14S C 0.85628(10) 0.25184(17) 0.37212(7) 0.0168(3) Uani 1 1 d . U . . .
H14S H 0.915540 0.217974 0.375662 0.020 Uiso 1 1 calc R U . . .
C15S C 0.80815(11) 0.2318(2) 0.32016(7) 0.0228(4) Uani 1 1 d . U . . .
H15C H 0.748656 0.264450 0.315205 0.027 Uiso 1 1 calc R U . . .
H15D H 0.832992 0.184714 0.287698 0.027 Uiso 1 1 calc R U . . .
C16S C 0.87043(10) -0.09850(16) 0.59450(7) 0.0153(3) Uani 1 1 d . U . . .
H16C H 0.809589 -0.080355 0.604795 0.018 Uiso 1 1 calc R U . . .
H16D H 0.868357 -0.111582 0.550192 0.018 Uiso 1 1 calc R U . . .
C17S C 1.05986(9) 0.28749(17) 0.59075(7) 0.0139(3) Uani 1 1 d . U . . .
H17D H 1.082100 0.196967 0.610480 0.021 Uiso 1 1 calc R U . . .
H17E H 1.093722 0.371132 0.608236 0.021 Uiso 1 1 calc R U . . .
H17F H 1.066141 0.281816 0.547373 0.021 Uiso 1 1 calc R U . . .
O1S O 0.81303(6) 0.20829(11) 0.58514(4) 0.0089(2) Uani 1 1 d . U . . .
O2S O 0.90427(8) -0.22833(12) 0.62421(5) 0.0212(3) Uani 1 1 d . U . . .
H2S H 0.873806 -0.249082 0.652547 0.032 Uiso 1 1 calc R U . . .
O3S O 0.86925(7) 0.37535(12) 0.68192(4) 0.0132(2) Uani 1 1 d . U . . .
H3S H 0.831086 0.323830 0.661945 0.020 Uiso 1 1 calc R U . . .
O4S O 0.69229(6) 0.31354(11) 0.53120(5) 0.0123(2) Uani 1 1 d . U . . .
H4SA H 0.677235 0.396539 0.542902 0.018 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 C2 1.5483(19) . ?
C1 C11 1.5542(19) . ?
C1 C12 1.538(2) . ?
C1 C13 1.5404(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5540(19) . ?
C3 C4 1.5405(19) . ?
C3 C8 1.5638(19) . ?
C3 O1 1.4670(16) . ?
C4 H4 1.0000 . ?
C4 C5 1.539(2) . ?
C4 C16 1.531(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.531(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.530(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.5514(19) . ?
C7 O3 1.4474(17) . ?
C8 C9 1.5525(19) . ?
C8 C17 1.5410(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5373(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5288(19) . ?
C11 O1 1.4506(16) . ?
C11 O4 1.3986(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.511(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.325(2) . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 O2 1.4300(18) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O2 H2 0.8400 . ?
O3 H3 0.8400 . ?
O4 H4A 0.8400 . ?
C1S C2S 1.5513(19) . ?
C1S C11S 1.5500(19) . ?
C1S C12S 1.535(2) . ?
C1S C13S 1.5445(19) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C3S 1.5560(18) . ?
C3S C4S 1.5383(19) . ?
C3S C8S 1.5650(19) . ?
C3S O1S 1.4667(16) . ?
C4S H4S 1.0000 . ?
C4S C5S 1.5378(19) . ?
C4S C16S 1.532(2) . ?
C5S H5SA 0.9900 . ?
C5S H5SB 0.9900 . ?
C5S C6S 1.530(2) . ?
C6S H6SA 0.9900 . ?
C6S H6SB 0.9900 . ?
C6S C7S 1.530(2) . ?
C7S H7S 1.0000 . ?
C7S C8S 1.5477(19) . ?
C7S O3S 1.4469(17) . ?
C8S C9S 1.5519(19) . ?
C8S C17S 1.5388(19) . ?
C9S H9SA 0.9900 . ?
C9S H9SB 0.9900 . ?
C9S C10S 1.5354(19) . ?
C10S H10C 0.9900 . ?
C10S H10D 0.9900 . ?
C10S C11S 1.5320(19) . ?
C11S O1S 1.4544(16) . ?
C11S O4S 1.3966(16) . ?
C12S H12D 0.9800 . ?
C12S H12E 0.9800 . ?
C12S H12F 0.9800 . ?
C13S H13C 0.9900 . ?
C13S H13D 0.9900 . ?
C13S C14S 1.501(2) . ?
C14S H14S 0.9500 . ?
C14S C15S 1.319(2) . ?
C15S H15C 0.9500 . ?
C15S H15D 0.9500 . ?
C16S H16C 0.9900 . ?
C16S H16D 0.9900 . ?
C16S O2S 1.4278(18) . ?
C17S H17D 0.9800 . ?
C17S H17E 0.9800 . ?
C17S H17F 0.9800 . ?
O2S H2S 0.8400 . ?
O3S H3S 0.8400 . ?
O4S H4SA 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 101.65(11) . . ?
C12 C1 C2 109.75(12) . . ?
C12 C1 C11 108.96(11) . . ?
C12 C1 C13 109.76(12) . . ?
C13 C1 C2 113.46(12) . . ?
C13 C1 C11 112.96(11) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C1 C2 C3 105.44(11) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C2 C3 C8 110.88(11) . . ?
C4 C3 C2 115.41(11) . . ?
C4 C3 C8 112.04(11) . . ?
O1 C3 C2 103.74(10) . . ?
O1 C3 C4 107.56(11) . . ?
O1 C3 C8 106.41(11) . . ?
C3 C4 H4 107.3 . . ?
C5 C4 C3 110.92(12) . . ?
C5 C4 H4 107.3 . . ?
C16 C4 C3 113.90(11) . . ?
C16 C4 H4 107.3 . . ?
C16 C4 C5 109.80(12) . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.98(12) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 110.94(12) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7 107.8 . . ?
C6 C7 C8 112.16(12) . . ?
C8 C7 H7 107.8 . . ?
O3 C7 C6 108.73(12) . . ?
O3 C7 H7 107.8 . . ?
O3 C7 C8 112.26(11) . . ?
C7 C8 C3 110.32(11) . . ?
C7 C8 C9 111.60(12) . . ?
C9 C8 C3 108.02(11) . . ?
C17 C8 C3 112.24(12) . . ?
C17 C8 C7 107.31(11) . . ?
C17 C8 C9 107.36(11) . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 115.49(11) . . ?
C10 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.27(11) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 C1 116.72(12) . . ?
O1 C11 C1 101.87(10) . . ?
O1 C11 C10 106.79(11) . . ?
O4 C11 C1 111.34(11) . . ?
O4 C11 C10 111.51(11) . . ?
O4 C11 O1 107.67(11) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13A 108.9 . . ?
C1 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C1 113.40(12) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14 117.5 . . ?
C15 C14 C13 125.03(15) . . ?
C15 C14 H14 117.5 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C4 C16 H16A 109.6 . . ?
C4 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
O2 C16 C4 110.50(12) . . ?
O2 C16 H16A 109.6 . . ?
O2 C16 H16B 109.6 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 O1 C3 105.05(10) . . ?
C16 O2 H2 109.5 . . ?
C7 O3 H3 109.5 . . ?
C11 O4 H4A 109.5 . . ?
C11S C1S C2S 102.08(11) . . ?
C12S C1S C2S 109.46(11) . . ?
C12S C1S C11S 109.70(11) . . ?
C12S C1S C13S 110.04(11) . . ?
C13S C1S C2S 113.70(12) . . ?
C13S C1S C11S 111.59(11) . . ?
C1S C2S H2SA 110.7 . . ?
C1S C2S H2SB 110.7 . . ?
C1S C2S C3S 105.27(11) . . ?
H2SA C2S H2SB 108.8 . . ?
C3S C2S H2SA 110.7 . . ?
C3S C2S H2SB 110.7 . . ?
C2S C3S C8S 110.51(11) . . ?
C4S C3S C2S 115.77(11) . . ?
C4S C3S C8S 112.04(11) . . ?
O1S C3S C2S 103.81(10) . . ?
O1S C3S C4S 107.23(11) . . ?
O1S C3S C8S 106.70(10) . . ?
C3S C4S H4S 107.4 . . ?
C5S C4S C3S 111.47(12) . . ?
C5S C4S H4S 107.4 . . ?
C16S C4S C3S 113.38(11) . . ?
C16S C4S H4S 107.4 . . ?
C16S C4S C5S 109.61(12) . . ?
C4S C5S H5SA 108.9 . . ?
C4S C5S H5SB 108.9 . . ?
H5SA C5S H5SB 107.7 . . ?
C6S C5S C4S 113.33(12) . . ?
C6S C5S H5SA 108.9 . . ?
C6S C5S H5SB 108.9 . . ?
C5S C6S H6SA 109.5 . . ?
C5S C6S H6SB 109.5 . . ?
C5S C6S C7S 110.78(12) . . ?
H6SA C6S H6SB 108.1 . . ?
C7S C6S H6SA 109.5 . . ?
C7S C6S H6SB 109.5 . . ?
C6S C7S H7S 107.8 . . ?
C6S C7S C8S 112.05(12) . . ?
C8S C7S H7S 107.8 . . ?
O3S C7S C6S 109.30(12) . . ?
O3S C7S H7S 107.8 . . ?
O3S C7S C8S 111.97(11) . . ?
C7S C8S C3S 110.57(11) . . ?
C7S C8S C9S 111.09(11) . . ?
C9S C8S C3S 108.21(11) . . ?
C17S C8S C3S 111.99(11) . . ?
C17S C8S C7S 107.46(11) . . ?
C17S C8S C9S 107.50(11) . . ?
C8S C9S H9SA 108.4 . . ?
C8S C9S H9SB 108.4 . . ?
H9SA C9S H9SB 107.4 . . ?
C10S C9S C8S 115.63(11) . . ?
C10S C9S H9SA 108.4 . . ?
C10S C9S H9SB 108.4 . . ?
C9S C10S H10C 109.0 . . ?
C9S C10S H10D 109.0 . . ?
H10C C10S H10D 107.8 . . ?
C11S C10S C9S 112.88(11) . . ?
C11S C10S H10C 109.0 . . ?
C11S C10S H10D 109.0 . . ?
C10S C11S C1S 116.33(11) . . ?
O1S C11S C1S 102.20(11) . . ?
O1S C11S C10S 106.73(10) . . ?
O4S C11S C1S 111.18(11) . . ?
O4S C11S C10S 111.70(11) . . ?
O4S C11S O1S 107.83(11) . . ?
C1S C12S H12D 109.5 . . ?
C1S C12S H12E 109.5 . . ?
C1S C12S H12F 109.5 . . ?
H12D C12S H12E 109.5 . . ?
H12D C12S H12F 109.5 . . ?
H12E C12S H12F 109.5 . . ?
C1S C13S H13C 108.7 . . ?
C1S C13S H13D 108.7 . . ?
H13C C13S H13D 107.6 . . ?
C14S C13S C1S 114.22(12) . . ?
C14S C13S H13C 108.7 . . ?
C14S C13S H13D 108.7 . . ?
C13S C14S H14S 118.0 . . ?
C15S C14S C13S 124.01(15) . . ?
C15S C14S H14S 118.0 . . ?
C14S C15S H15C 120.0 . . ?
C14S C15S H15D 120.0 . . ?
H15C C15S H15D 120.0 . . ?
C4S C16S H16C 109.6 . . ?
C4S C16S H16D 109.6 . . ?
H16C C16S H16D 108.1 . . ?
O2S C16S C4S 110.32(12) . . ?
O2S C16S H16C 109.6 . . ?
O2S C16S H16D 109.6 . . ?
C8S C17S H17D 109.5 . . ?
C8S C17S H17E 109.5 . . ?
C8S C17S H17F 109.5 . . ?
H17D C17S H17E 109.5 . . ?
H17D C17S H17F 109.5 . . ?
H17E C17S H17F 109.5 . . ?
C11S O1S C3S 105.02(10) . . ?
C16S O2S H2S 109.5 . . ?
C7S O3S H3S 109.5 . . ?
C11S O4S H4SA 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
C1 C2 C3 C4 -128.91(12) . . . . ?
C1 C2 C3 C8 102.34(13) . . . . ?
C1 C2 C3 O1 -11.53(14) . . . . ?
C1 C11 O1 C3 -48.51(12) . . . . ?
C1 C13 C14 C15 -106.73(18) . . . . ?
C2 C1 C11 C10 -77.02(14) . . . . ?
C2 C1 C11 O1 38.85(13) . . . . ?
C2 C1 C11 O4 153.39(11) . . . . ?
C2 C1 C13 C14 -59.35(16) . . . . ?
C2 C3 C4 C5 178.26(11) . . . . ?
C2 C3 C4 C16 53.79(16) . . . . ?
C2 C3 C8 C7 -175.47(11) . . . . ?
C2 C3 C8 C9 -53.24(14) . . . . ?
C2 C3 C8 C17 64.92(15) . . . . ?
C2 C3 O1 C11 37.55(13) . . . . ?
C3 C4 C5 C6 54.22(16) . . . . ?
C3 C4 C16 O2 -170.50(11) . . . . ?
C3 C8 C9 C10 -38.88(16) . . . . ?
C4 C3 C8 C7 53.99(15) . . . . ?
C4 C3 C8 C9 176.22(11) . . . . ?
C4 C3 C8 C17 -65.62(15) . . . . ?
C4 C3 O1 C11 160.28(11) . . . . ?
C4 C5 C6 C7 -54.98(16) . . . . ?
C5 C4 C16 O2 64.43(15) . . . . ?
C5 C6 C7 C8 55.29(16) . . . . ?
C5 C6 C7 O3 -69.46(15) . . . . ?
C6 C7 C8 C3 -54.83(15) . . . . ?
C6 C7 C8 C9 -174.92(11) . . . . ?
C6 C7 C8 C17 67.73(15) . . . . ?
C7 C8 C9 C10 82.55(15) . . . . ?
C8 C3 C4 C5 -53.56(15) . . . . ?
C8 C3 C4 C16 -178.03(12) . . . . ?
C8 C3 O1 C11 -79.48(12) . . . . ?
C8 C9 C10 C11 36.62(17) . . . . ?
C9 C10 C11 C1 60.70(16) . . . . ?
C9 C10 C11 O1 -52.41(15) . . . . ?
C9 C10 C11 O4 -169.79(11) . . . . ?
C10 C11 O1 C3 74.41(12) . . . . ?
C11 C1 C2 C3 -16.25(14) . . . . ?
C11 C1 C13 C14 -174.36(12) . . . . ?
C12 C1 C2 C3 99.00(13) . . . . ?
C12 C1 C11 C10 167.15(11) . . . . ?
C12 C1 C11 O1 -76.97(13) . . . . ?
C12 C1 C11 O4 37.56(15) . . . . ?
C12 C1 C13 C14 63.83(16) . . . . ?
C13 C1 C2 C3 -137.82(12) . . . . ?
C13 C1 C11 C10 44.90(16) . . . . ?
C13 C1 C11 O1 160.77(11) . . . . ?
C13 C1 C11 O4 -84.70(14) . . . . ?
C16 C4 C5 C6 -179.02(12) . . . . ?
C17 C8 C9 C10 -160.12(12) . . . . ?
O1 C3 C4 C5 63.04(14) . . . . ?
O1 C3 C4 C16 -61.43(15) . . . . ?
O1 C3 C8 C7 -63.30(13) . . . . ?
O1 C3 C8 C9 58.92(13) . . . . ?
O1 C3 C8 C17 177.08(11) . . . . ?
O3 C7 C8 C3 67.95(15) . . . . ?
O3 C7 C8 C9 -52.14(16) . . . . ?
O3 C7 C8 C17 -169.49(12) . . . . ?
O4 C11 O1 C3 -165.71(10) . . . . ?
C1S C2S C3S C4S 130.09(12) . . . . ?
C1S C2S C3S C8S -101.19(12) . . . . ?
C1S C2S C3S O1S 12.88(13) . . . . ?
C1S C11S O1S C3S 47.92(12) . . . . ?
C1S C13S C14S C15S 112.75(18) . . . . ?
C2S C1S C11S C10S 78.29(14) . . . . ?
C2S C1S C11S O1S -37.53(13) . . . . ?
C2S C1S C11S O4S -152.34(11) . . . . ?
C2S C1S C13S C14S 63.08(16) . . . . ?
C2S C3S C4S C5S -179.90(11) . . . . ?
C2S C3S C4S C16S -55.64(16) . . . . ?
C2S C3S C8S C7S 175.83(11) . . . . ?
C2S C3S C8S C9S 53.96(14) . . . . ?
C2S C3S C8S C17S -64.36(14) . . . . ?
C2S C3S O1S C11S -37.95(13) . . . . ?
C3S C4S C5S C6S -53.07(16) . . . . ?
C3S C4S C16S O2S 171.37(11) . . . . ?
C3S C8S C9S C10S 38.87(16) . . . . ?
C4S C3S C8S C7S -53.46(15) . . . . ?
C4S C3S C8S C9S -175.33(11) . . . . ?
C4S C3S C8S C17S 66.36(15) . . . . ?
C4S C3S O1S C11S -160.97(10) . . . . ?
C4S C5S C6S C7S 54.54(16) . . . . ?
C5S C4S C16S O2S -63.36(15) . . . . ?
C5S C6S C7S C8S -55.68(16) . . . . ?
C5S C6S C7S O3S 69.03(15) . . . . ?
C6S C7S C8S C3S 55.33(15) . . . . ?
C6S C7S C8S C9S 175.49(11) . . . . ?
C6S C7S C8S C17S -67.18(15) . . . . ?
C7S C8S C9S C10S -82.69(14) . . . . ?
C8S C3S C4S C5S 52.13(15) . . . . ?
C8S C3S C4S C16S 176.40(11) . . . . ?
C8S C3S O1S C11S 78.81(12) . . . . ?
C8S C9S C10S C11S -37.34(16) . . . . ?
C9S C10S C11S C1S -59.96(15) . . . . ?
C9S C10S C11S O1S 53.29(14) . . . . ?
C9S C10S C11S O4S 170.92(11) . . . . ?
C10S C11S O1S C3S -74.68(12) . . . . ?
C11S C1S C2S C3S 14.69(14) . . . . ?
C11S C1S C13S C14S 177.88(12) . . . . ?
C12S C1S C2S C3S -101.49(13) . . . . ?
C12S C1S C11S C10S -165.70(11) . . . . ?
C12S C1S C11S O1S 78.48(13) . . . . ?
C12S C1S C11S O4S -36.34(15) . . . . ?
C12S C1S C13S C14S -60.10(16) . . . . ?
C13S C1S C2S C3S 135.01(12) . . . . ?
C13S C1S C11S C10S -43.49(16) . . . . ?
C13S C1S C11S O1S -159.31(11) . . . . ?
C13S C1S C11S O4S 85.87(14) . . . . ?
C16S C4S C5S C6S -179.43(12) . . . . ?
C17S C8S C9S C10S 160.01(12) . . . . ?
O1S C3S C4S C5S -64.61(14) . . . . ?
O1S C3S C4S C16S 59.65(14) . . . . ?
O1S C3S C8S C7S 63.60(13) . . . . ?
O1S C3S C8S C9S -58.27(13) . . . . ?
O1S C3S C8S C17S -176.58(11) . . . . ?
O3S C7S C8S C3S -67.90(15) . . . . ?
O3S C7S C8S C9S 52.27(15) . . . . ?
O3S C7S C8S C17S 169.60(11) . . . . ?
O4S C11S O1S C3S 165.17(10) . . . . ?





_olex2_submission_special_instructions 'No special instructions were received'
loop_
_publcif_info_exptl_table_extra_item

sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item

?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_p21c_a
_database_code_depnum_ccdc_archive 'CCDC 2003841'
loop_
_audit_author_name
_audit_author_address
'toyoharu kobayashi'
;Tokyo University of Pharmacy and Life Sciences
Japan
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-03-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_publcif_datablock.id            {97f93579-9cbe-4926-8be2-e96004bc8ee7}
_publcif_funding_html            
;
;

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 O4'
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.559(2)
_cell_length_b                   8.9149(17)
_cell_length_c                   19.341(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.146(2)
_cell_angle_gamma                90
_cell_volume                     1819.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1016 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.9601.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method 
'slow crystallization from a ethyl acetate solution at room temperature'
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16603
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.930
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2730
_reflns_number_total             3228
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     300
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.030
_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)+(0.0437P)²+0.8708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0955
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.05 and sigma
for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C2(H2A,H2B),
 C5(H5A,H5B), C6(H6A,H6B)
3.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.13343(9) 0.25980(10) 0.46809(5) 0.0143(2) Uani 1 1 d . U . . .
O3 O 0.10603(9) 0.10556(11) 0.37235(5) 0.0173(2) Uani 1 1 d . U . . .
H3 H 0.059281 0.040001 0.389351 0.026 Uiso 1 1 calc R U . . .
O2 O 0.06698(9) 0.10740(11) 0.58050(5) 0.0193(2) Uani 1 1 d . U . . .
H2 H 0.051404 0.142128 0.540712 0.029 Uiso 1 1 calc R U . . .
O4 O 0.60592(10) 0.04526(11) 0.28842(6) 0.0238(3) Uani 1 1 d . U . . .
C11 C 0.19447(13) 0.15357(16) 0.42220(7) 0.0147(2) Uani 1 1 d . U . . .
C1 C 0.29467(13) 0.25565(15) 0.38922(7) 0.0147(2) Uani 1 1 d . U . . .
C12 C 0.40081(13) 0.16774(16) 0.35549(7) 0.0157(3) Uani 1 1 d . U . . .
H12A H 0.437258 0.095298 0.389546 0.019 Uiso 1 1 calc R U . . .
H12B H 0.363908 0.109656 0.316027 0.019 Uiso 1 1 calc R U . . .
C14 C 0.61171(13) 0.18042(16) 0.29673(7) 0.0166(3) Uani 1 1 d . U . . .
C8 C 0.28034(13) 0.22017(16) 0.56543(7) 0.0154(2) Uani 1 1 d . U . . .
C4 C 0.18785(13) 0.47522(16) 0.53777(7) 0.0167(3) Uani 1 1 d . U . . .
C9 C 0.32332(13) 0.07296(16) 0.53134(7) 0.0161(3) Uani 1 1 d . U . . .
H9A H 0.412324 0.085007 0.517944 0.019 Uiso 1 1 calc R U . . .
H9B H 0.321500 -0.008194 0.566228 0.019 Uiso 1 1 calc R U . . .
C10 C 0.24348(13) 0.02346(16) 0.46712(7) 0.0156(3) Uani 1 1 d . U . . .
H10A H 0.295535 -0.043093 0.438645 0.019 Uiso 1 1 calc R U . . .
H10B H 0.170228 -0.035619 0.482401 0.019 Uiso 1 1 calc R U . . .
C13 C 0.50718(13) 0.26666(16) 0.32961(7) 0.0165(3) Uani 1 1 d . U . . .
H13A H 0.470768 0.338836 0.295416 0.020 Uiso 1 1 calc R U . . .
H13B H 0.543833 0.325049 0.369036 0.020 Uiso 1 1 calc R U . . .
C18 C 0.22705(13) 0.35614(16) 0.33519(7) 0.0180(3) Uani 1 1 d . U . . .
H18A H 0.193582 0.294305 0.296798 0.027 Uiso 1 1 calc R U . . .
H18B H 0.287227 0.429376 0.317696 0.027 Uiso 1 1 calc R U . . .
H18C H 0.157115 0.409014 0.356510 0.027 Uiso 1 1 calc R U . . .
C7 C 0.16829(13) 0.19243(16) 0.61395(7) 0.0173(3) Uani 1 1 d . U . . .
H7 H 0.201770 0.131972 0.654175 0.021 Uiso 1 1 calc R U . . .
C3 C 0.23882(13) 0.33196(16) 0.50683(7) 0.0148(2) Uani 1 1 d . U . . .
C15 C 0.72500(13) 0.27036(16) 0.27350(7) 0.0177(3) Uani 1 1 d . U . . .
H15 H 0.723284 0.371236 0.296055 0.021 Uiso 1 1 calc R U . . .
C2 C 0.34111(13) 0.35043(16) 0.45199(7) 0.0154(3) Uani 1 1 d . U . . .
H2A H 0.349671 0.457121 0.438745 0.018 Uiso 1 1 calc R U . . .
H2B H 0.424286 0.313776 0.470281 0.018 Uiso 1 1 calc R U . . .
C5 C 0.07860(14) 0.44915(17) 0.58471(7) 0.0193(3) Uani 1 1 d . U . . .
H5A H 0.005114 0.409464 0.557163 0.023 Uiso 1 1 calc R U . . .
H5B H 0.053241 0.545741 0.605319 0.023 Uiso 1 1 calc R U . . .
C20 C 0.39144(13) 0.28238(17) 0.61028(7) 0.0187(3) Uani 1 1 d . U . . .
H20A H 0.465579 0.294961 0.581831 0.028 Uiso 1 1 calc R U . . .
H20B H 0.411920 0.212231 0.648080 0.028 Uiso 1 1 calc R U . . .
H20C H 0.367704 0.379635 0.629551 0.028 Uiso 1 1 calc R U . . .
C19 C 0.23537(14) 0.61081(17) 0.52837(8) 0.0216(3) Uani 1 1 d . U . . .
H19A H 0.200800 0.694672 0.551387 0.026 Uiso 1 1 calc R U . . .
H19B H 0.304027 0.624246 0.498608 0.026 Uiso 1 1 calc R U . . .
C16 C 0.84926(14) 0.19349(18) 0.29453(8) 0.0225(3) Uani 1 1 d . U . . .
H16A H 0.855744 0.098344 0.269534 0.034 Uiso 1 1 calc R U . . .
H16B H 0.851695 0.174086 0.344437 0.034 Uiso 1 1 calc R U . . .
H16C H 0.920338 0.258553 0.283164 0.034 Uiso 1 1 calc R U . . .
C6 C 0.11500(14) 0.33801(16) 0.64262(7) 0.0191(3) Uani 1 1 d . U . . .
H6A H 0.179142 0.384651 0.674482 0.023 Uiso 1 1 calc R U . . .
H6B H 0.039282 0.315089 0.669391 0.023 Uiso 1 1 calc R U . . .
C17 C 0.71399(15) 0.29191(18) 0.19512(8) 0.0232(3) Uani 1 1 d . U . . .
H17A H 0.632193 0.338261 0.182520 0.035 Uiso 1 1 calc R U . . .
H17B H 0.719996 0.194266 0.172200 0.035 Uiso 1 1 calc R U . . .
H17C H 0.782733 0.357014 0.180388 0.035 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 1.4639(16) . ?
O1 C3 1.4666(17) . ?
O3 H3 0.8400 . ?
O3 C11 1.3846(17) . ?
O2 H2 0.8400 . ?
O2 C7 1.4441(17) . ?
O4 C14 1.2169(18) . ?
C11 C1 1.5508(19) . ?
C11 C10 1.5278(19) . ?
C1 C12 1.5332(19) . ?
C1 C18 1.5324(19) . ?
C1 C2 1.5439(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5270(19) . ?
C14 C13 1.5054(19) . ?
C14 C15 1.5217(19) . ?
C8 C9 1.544(2) . ?
C8 C7 1.5572(19) . ?
C8 C3 1.5596(19) . ?
C8 C20 1.5363(19) . ?
C4 C3 1.5175(19) . ?
C4 C5 1.5124(19) . ?
C4 C19 1.324(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.539(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C7 H7 1.0000 . ?
C7 C6 1.527(2) . ?
C3 C2 1.5507(18) . ?
C15 H15 1.0000 . ?
C15 C16 1.522(2) . ?
C15 C17 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.534(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C3 104.52(9) . . ?
C11 O3 H3 109.5 . . ?
C7 O2 H2 109.5 . . ?
O1 C11 C1 101.09(10) . . ?
O1 C11 C10 107.08(10) . . ?
O3 C11 O1 108.75(10) . . ?
O3 C11 C1 110.34(11) . . ?
O3 C11 C10 111.50(11) . . ?
C10 C11 C1 117.24(11) . . ?
C12 C1 C11 113.32(11) . . ?
C12 C1 C2 113.49(11) . . ?
C18 C1 C11 108.42(11) . . ?
C18 C1 C12 109.76(11) . . ?
C18 C1 C2 110.02(12) . . ?
C2 C1 C11 101.49(11) . . ?
C1 C12 H12A 108.8 . . ?
C1 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C1 113.74(11) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O4 C14 C13 121.83(13) . . ?
O4 C14 C15 121.26(13) . . ?
C13 C14 C15 116.90(12) . . ?
C9 C8 C7 111.37(12) . . ?
C9 C8 C3 108.17(11) . . ?
C7 C8 C3 109.89(11) . . ?
C20 C8 C9 108.51(11) . . ?
C20 C8 C7 107.36(11) . . ?
C20 C8 C3 111.57(11) . . ?
C5 C4 C3 113.39(12) . . ?
C19 C4 C3 124.93(13) . . ?
C19 C4 C5 121.61(13) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 115.29(11) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C11 C10 C9 113.88(11) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 C12 113.79(12) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C7 C8 112.34(11) . . ?
O2 C7 H7 107.5 . . ?
O2 C7 C6 109.39(11) . . ?
C8 C7 H7 107.5 . . ?
C6 C7 C8 112.48(12) . . ?
C6 C7 H7 107.5 . . ?
O1 C3 C8 106.15(11) . . ?
O1 C3 C4 107.28(11) . . ?
O1 C3 C2 103.39(10) . . ?
C4 C3 C8 110.21(11) . . ?
C4 C3 C2 116.53(11) . . ?
C2 C3 C8 112.39(11) . . ?
C14 C15 H15 108.5 . . ?
C14 C15 C16 111.29(12) . . ?
C14 C15 C17 109.13(12) . . ?
C16 C15 H15 108.5 . . ?
C16 C15 C17 110.76(12) . . ?
C17 C15 H15 108.5 . . ?
C1 C2 C3 105.72(11) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.21(12) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C19 H19A 120.0 . . ?
C4 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C6 C5 111.69(12) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C11 C1 C12 162.19(11) . . . . ?
O1 C11 C1 C18 -75.70(12) . . . . ?
O1 C11 C1 C2 40.14(12) . . . . ?
O1 C11 C10 C9 -50.72(14) . . . . ?
O1 C3 C2 C1 -11.66(13) . . . . ?
O3 C11 C1 C12 -82.85(14) . . . . ?
O3 C11 C1 C18 39.26(15) . . . . ?
O3 C11 C1 C2 155.11(11) . . . . ?
O3 C11 C10 C9 -169.57(11) . . . . ?
O2 C7 C6 C5 -71.92(14) . . . . ?
O4 C14 C13 C12 4.2(2) . . . . ?
O4 C14 C15 C16 -45.28(19) . . . . ?
O4 C14 C15 C17 77.26(17) . . . . ?
C11 O1 C3 C8 -80.05(12) . . . . ?
C11 O1 C3 C4 162.12(10) . . . . ?
C11 O1 C3 C2 38.42(12) . . . . ?
C11 C1 C12 C13 -173.90(11) . . . . ?
C11 C1 C2 C3 -17.22(13) . . . . ?
C1 C11 C10 C9 61.89(16) . . . . ?
C1 C12 C13 C14 179.78(12) . . . . ?
C12 C1 C2 C3 -139.14(12) . . . . ?
C8 C9 C10 C11 35.40(16) . . . . ?
C8 C7 C6 C5 53.65(16) . . . . ?
C8 C3 C2 C1 102.38(13) . . . . ?
C4 C3 C2 C1 -129.06(12) . . . . ?
C4 C5 C6 C7 -53.05(16) . . . . ?
C9 C8 C7 O2 -50.21(15) . . . . ?
C9 C8 C7 C6 -174.17(12) . . . . ?
C9 C8 C3 O1 60.59(13) . . . . ?
C9 C8 C3 C4 176.46(11) . . . . ?
C9 C8 C3 C2 -51.75(15) . . . . ?
C10 C11 C1 C12 46.24(16) . . . . ?
C10 C11 C1 C18 168.35(12) . . . . ?
C10 C11 C1 C2 -75.80(14) . . . . ?
C13 C14 C15 C16 135.34(13) . . . . ?
C13 C14 C15 C17 -102.12(14) . . . . ?
C18 C1 C12 C13 64.74(15) . . . . ?
C18 C1 C2 C3 97.45(13) . . . . ?
C7 C8 C9 C10 81.78(14) . . . . ?
C7 C8 C3 O1 -61.18(14) . . . . ?
C7 C8 C3 C4 54.69(15) . . . . ?
C7 C8 C3 C2 -173.52(11) . . . . ?
C3 O1 C11 O3 -166.06(10) . . . . ?
C3 O1 C11 C1 -49.91(12) . . . . ?
C3 O1 C11 C10 73.32(12) . . . . ?
C3 C8 C9 C10 -39.07(15) . . . . ?
C3 C8 C7 O2 69.63(15) . . . . ?
C3 C8 C7 C6 -54.32(15) . . . . ?
C3 C4 C5 C6 55.68(16) . . . . ?
C15 C14 C13 C12 -176.46(12) . . . . ?
C2 C1 C12 C13 -58.82(16) . . . . ?
C5 C4 C3 O1 58.35(14) . . . . ?
C5 C4 C3 C8 -56.80(15) . . . . ?
C5 C4 C3 C2 173.59(12) . . . . ?
C20 C8 C9 C10 -160.26(11) . . . . ?
C20 C8 C7 O2 -168.86(11) . . . . ?
C20 C8 C7 C6 67.18(15) . . . . ?
C20 C8 C3 O1 179.87(10) . . . . ?
C20 C8 C3 C4 -64.27(14) . . . . ?
C20 C8 C3 C2 67.52(15) . . . . ?
C19 C4 C3 O1 -124.59(15) . . . . ?
C19 C4 C3 C8 120.26(16) . . . . ?
C19 C4 C3 C2 -9.3(2) . . . . ?
C19 C4 C5 C6 -121.49(16) . . . . ?


_olex2_exptl_crystal_mounting_method 
'The  crystals were picked, soaked in perfluoropolyether oil and mounted on MiTeGen MicroMounts.'
_olex2_submission_special_instructions 'No special instructions were received'
