# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ic21663
_database_code_depnum_ccdc_archive 'CCDC 2208811'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2022-09-22 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        'Chlorofurancembranoid B'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H35 Cl O4'
_chemical_formula_weight         374.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   10.1046(4)
_cell_length_b                   10.4180(3)
_cell_length_c                   10.9661(4)
_cell_angle_alpha                97.3100(13)
_cell_angle_beta                 99.4725(13)
_cell_angle_gamma                107.4541(12)
_cell_volume                     1066.93(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.08

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38323
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12414
_reflns_number_gt                8865
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.5664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3412 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         12414
_refine_ls_number_parameters     468
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.15071(13) 0.16896(13) 0.82375(13) 0.0615(4) Uani 1 1 d . . . . .
O1 O 0.8346(3) 0.5980(3) 0.5570(3) 0.0470(7) Uani 1 1 d . . . . .
H1 H 0.749925 0.583111 0.520999 0.070 Uiso 1 1 calc R U . . .
O2 O 1.0534(3) 0.5169(4) 0.5638(3) 0.0508(8) Uani 1 1 d . . . . .
H2 H 1.009363 0.550108 0.511564 0.076 Uiso 1 1 calc R U . . .
O3 O 0.7659(3) 0.0151(3) 0.5912(3) 0.0382(6) Uani 1 1 d . . . . .
O4 O 0.4954(3) 0.0373(3) 0.5168(3) 0.0466(7) Uani 1 1 d . . . . .
H4 H 0.560345 0.045782 0.476403 0.070 Uiso 1 1 calc R U . . .
C1 C 0.6452(4) 0.4343(4) 0.7611(4) 0.0362(8) Uani 1 1 d . . . . .
C2 C 0.7664(4) 0.5189(4) 0.7424(4) 0.0385(8) Uani 1 1 d . . . . .
H2A H 0.810783 0.600760 0.803375 0.046 Uiso 1 1 calc R U . . .
C3 C 0.8401(4) 0.4998(4) 0.6371(4) 0.0369(8) Uani 1 1 d . . . . .
H3 H 0.792158 0.405378 0.586183 0.044 Uiso 1 1 calc R U . . .
C4 C 1.0010(4) 0.5234(4) 0.6779(4) 0.0381(9) Uani 1 1 d . . . . .
C5 C 1.0303(4) 0.4108(4) 0.7430(4) 0.0382(8) Uani 1 1 d . . . . .
H5A H 1.132037 0.442505 0.784946 0.046 Uiso 1 1 calc R U . . .
H5B H 0.974709 0.398301 0.809523 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9962(4) 0.2722(4) 0.6592(4) 0.0385(9) Uani 1 1 d . . . . .
H6A H 1.073813 0.274228 0.614185 0.046 Uiso 1 1 calc R U . . .
H6B H 0.907719 0.253559 0.595547 0.046 Uiso 1 1 calc R U . . .
C7 C 0.9778(4) 0.1577(4) 0.7346(4) 0.0393(9) Uani 1 1 d . . . . .
H7 H 0.920783 0.175442 0.797225 0.047 Uiso 1 1 calc R U . . .
C8 C 0.9003(5) 0.0113(4) 0.6602(4) 0.0403(9) Uani 1 1 d . . . . .
C9 C 0.8556(5) -0.0881(5) 0.7488(5) 0.0489(11) Uani 1 1 d . . . . .
H9A H 0.837648 -0.183766 0.707688 0.059 Uiso 1 1 calc R U . . .
H9B H 0.929270 -0.065284 0.827106 0.059 Uiso 1 1 calc R U . . .
C10 C 0.7194(5) -0.0673(4) 0.7759(4) 0.0448(10) Uani 1 1 d . . . . .
H10A H 0.658889 -0.148544 0.801909 0.054 Uiso 1 1 calc R U . . .
H10B H 0.740044 0.014529 0.841833 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6501(5) -0.0475(4) 0.6487(4) 0.0397(9) Uani 1 1 d . . . . .
H11 H 0.595484 -0.140170 0.596462 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5512(4) 0.0384(4) 0.6460(4) 0.0373(8) Uani 1 1 d . . . . .
C13 C 0.6296(4) 0.1864(4) 0.7176(4) 0.0378(8) Uani 1 1 d . . . . .
H13A H 0.633544 0.187490 0.808548 0.045 Uiso 1 1 calc R U . . .
H13B H 0.728573 0.213346 0.705671 0.045 Uiso 1 1 calc R U . . .
C14 C 0.5649(4) 0.2951(4) 0.6793(4) 0.0361(8) Uani 1 1 d . . . . .
H14A H 0.567268 0.300601 0.590183 0.043 Uiso 1 1 calc R U . . .
H14B H 0.464422 0.267546 0.686943 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5833(4) 0.4802(4) 0.8697(4) 0.0412(9) Uani 1 1 d . . . . .
H15 H 0.659049 0.560351 0.926655 0.049 Uiso 1 1 calc R U . . .
C16 C 0.4590(5) 0.5283(5) 0.8210(5) 0.0526(11) Uani 1 1 d . . . . .
H16A H 0.492653 0.606608 0.779976 0.079 Uiso 1 1 calc R U . . .
H16B H 0.419117 0.555754 0.891653 0.079 Uiso 1 1 calc R U . . .
H16C H 0.385719 0.453449 0.760197 0.079 Uiso 1 1 calc R U . . .
C17 C 0.5358(5) 0.3704(5) 0.9477(4) 0.0501(11) Uani 1 1 d . . . . .
H17A H 0.456791 0.293067 0.895651 0.075 Uiso 1 1 calc R U . . .
H17B H 0.504924 0.408892 1.019923 0.075 Uiso 1 1 calc R U . . .
H17C H 0.615277 0.338859 0.977787 0.075 Uiso 1 1 calc R U . . .
C18 C 1.0809(5) 0.6627(5) 0.7620(6) 0.0557(13) Uani 1 1 d . . . . .
H18A H 1.183364 0.680275 0.772482 0.084 Uiso 1 1 calc R U . . .
H18B H 1.055348 0.663348 0.844415 0.084 Uiso 1 1 calc R U . . .
H18C H 1.055362 0.734043 0.723118 0.084 Uiso 1 1 calc R U . . .
C19 C 0.9784(6) -0.0345(5) 0.5653(5) 0.0542(12) Uani 1 1 d . . . . .
H19A H 0.920301 -0.125236 0.516443 0.081 Uiso 1 1 calc R U . . .
H19B H 1.068965 -0.038829 0.609660 0.081 Uiso 1 1 calc R U . . .
H19C H 0.996381 0.031169 0.508423 0.081 Uiso 1 1 calc R U . . .
C20 C 0.4219(5) -0.0307(5) 0.6966(5) 0.0498(11) Uani 1 1 d . . . . .
H20A H 0.353434 0.018641 0.684300 0.075 Uiso 1 1 calc R U . . .
H20B H 0.451119 -0.029534 0.786618 0.075 Uiso 1 1 calc R U . . .
H20C H 0.377691 -0.125647 0.651591 0.075 Uiso 1 1 calc R U . . .
Cl2 Cl 0.72895(13) 0.80729(13) 0.11155(12) 0.0599(3) Uani 1 1 d . . . . .
O5 O 0.3174(4) 0.5509(5) 0.5239(3) 0.0670(11) Uani 1 1 d . . . . .
H5 H 0.241569 0.556370 0.542369 0.100 Uiso 1 1 calc R U . . .
O6 O 0.5705(3) 0.6116(3) 0.4872(3) 0.0426(7) Uani 1 1 d . . . . .
H6 H 0.536730 0.588404 0.549199 0.064 Uiso 1 1 calc R U . . .
O7 O 0.5126(3) 1.0253(3) 0.2677(3) 0.0420(7) Uani 1 1 d . . . . .
O8 O 0.2575(4) 1.0352(3) 0.3401(3) 0.0493(8) Uani 1 1 d . . . . .
H8 H 0.326723 1.029321 0.390526 0.074 Uiso 1 1 calc R U . . .
C21 C 0.1100(4) 0.5956(4) 0.2587(4) 0.0395(9) Uani 1 1 d . . . . .
C22 C 0.1967(4) 0.5328(4) 0.3104(4) 0.0418(9) Uani 1 1 d . . . . .
H22 H 0.169578 0.436760 0.281840 0.050 Uiso 1 1 calc R U . . .
C23 C 0.3314(4) 0.5965(5) 0.4080(4) 0.0397(9) Uani 1 1 d . . . . .
H23 H 0.355057 0.698355 0.422640 0.048 Uiso 1 1 calc R U . . .
C24 C 0.4600(4) 0.5599(4) 0.3741(4) 0.0366(8) Uani 1 1 d . . . . .
C25 C 0.5149(4) 0.6290(4) 0.2702(4) 0.0391(9) Uani 1 1 d . . . . .
H25A H 0.434362 0.606847 0.197353 0.047 Uiso 1 1 calc R U . . .
H25B H 0.584473 0.588057 0.243012 0.047 Uiso 1 1 calc R U . . .
C26 C 0.5852(5) 0.7842(4) 0.3018(4) 0.0375(8) Uani 1 1 d . . . . .
H26A H 0.530317 0.824958 0.352542 0.045 Uiso 1 1 calc R U . . .
H26B H 0.682228 0.806791 0.353114 0.045 Uiso 1 1 calc R U . . .
C27 C 0.5935(5) 0.8462(4) 0.1841(4) 0.0390(8) Uani 1 1 d . . . . .
H27 H 0.500462 0.799847 0.123367 0.047 Uiso 1 1 calc R U . . .
C28 C 0.6193(5) 1.0020(4) 0.2017(4) 0.0417(9) Uani 1 1 d . . . . .
C29 C 0.5821(6) 1.0443(5) 0.0756(5) 0.0542(12) Uani 1 1 d . . . . .
H29A H 0.609027 0.991358 0.007965 0.065 Uiso 1 1 calc R U . . .
H29B H 0.630549 1.143254 0.080381 0.065 Uiso 1 1 calc R U . . .
C30 C 0.4213(6) 1.0110(5) 0.0527(4) 0.0524(11) Uani 1 1 d . . . . .
H30A H 0.388726 1.066437 -0.004996 0.063 Uiso 1 1 calc R U . . .
H30B H 0.371196 0.912633 0.017467 0.063 Uiso 1 1 calc R U . . .
C31 C 0.3984(5) 1.0490(4) 0.1832(4) 0.0442(10) Uani 1 1 d . . . . .
H31 H 0.413459 1.149549 0.199439 0.053 Uiso 1 1 calc R U . . .
C32 C 0.2573(5) 0.9760(4) 0.2158(4) 0.0429(9) Uani 1 1 d . . . . .
C33 C 0.2302(5) 0.8203(4) 0.2020(4) 0.0442(10) Uani 1 1 d . . . . .
H33A H 0.182809 0.776449 0.113701 0.053 Uiso 1 1 calc R U . . .
H33B H 0.323043 0.805054 0.218909 0.053 Uiso 1 1 calc R U . . .
C34 C 0.1398(4) 0.7488(4) 0.2884(4) 0.0413(9) Uani 1 1 d . . . . .
H34A H 0.190374 0.784783 0.377237 0.050 Uiso 1 1 calc R U . . .
H34B H 0.048921 0.768291 0.276945 0.050 Uiso 1 1 calc R U . . .
C35 C -0.0296(5) 0.5160(5) 0.1657(5) 0.0488(10) Uani 1 1 d . . . . .
H35 H -0.045153 0.573996 0.102360 0.059 Uiso 1 1 calc R U . . .
C36 C -0.0343(6) 0.3789(6) 0.0944(5) 0.0639(14) Uani 1 1 d . . . . .
H36A H 0.048193 0.392119 0.055361 0.096 Uiso 1 1 calc R U . . .
H36B H -0.121631 0.340693 0.028988 0.096 Uiso 1 1 calc R U . . .
H36C H -0.032371 0.315491 0.153002 0.096 Uiso 1 1 calc R U . . .
C37 C -0.1504(5) 0.4959(6) 0.2369(5) 0.0606(14) Uani 1 1 d . . . . .
H37A H -0.140295 0.435864 0.297234 0.091 Uiso 1 1 calc R U . . .
H37B H -0.241773 0.454094 0.177015 0.091 Uiso 1 1 calc R U . . .
H37C H -0.146360 0.584893 0.282107 0.091 Uiso 1 1 calc R U . . .
C38 C 0.4275(6) 0.4059(5) 0.3391(5) 0.0560(12) Uani 1 1 d . . . . .
H38A H 0.515832 0.386184 0.335601 0.084 Uiso 1 1 calc R U . . .
H38B H 0.362293 0.371331 0.256591 0.084 Uiso 1 1 calc R U . . .
H38C H 0.383320 0.361093 0.402479 0.084 Uiso 1 1 calc R U . . .
C39 C 0.7627(5) 1.0874(5) 0.2825(5) 0.0532(11) Uani 1 1 d . . . . .
H39A H 0.768238 1.183797 0.297964 0.080 Uiso 1 1 calc R U . . .
H39B H 0.837448 1.077598 0.239083 0.080 Uiso 1 1 calc R U . . .
H39C H 0.775342 1.056190 0.362910 0.080 Uiso 1 1 calc R U . . .
C40 C 0.1372(6) 1.0046(6) 0.1313(6) 0.0634(14) Uani 1 1 d . . . . .
H40A H 0.047539 0.963949 0.156584 0.095 Uiso 1 1 calc R U . . .
H40B H 0.129558 0.964546 0.043526 0.095 Uiso 1 1 calc R U . . .
H40C H 0.157661 1.103823 0.139586 0.095 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.818(4) . ?
O1 C3 1.438(5) . ?
O2 C4 1.437(5) . ?
O3 C11 1.443(5) . ?
O3 C8 1.456(5) . ?
O4 C12 1.433(5) . ?
C1 C2 1.341(6) . ?
C1 C14 1.513(6) . ?
C1 C15 1.522(6) . ?
C2 C3 1.497(6) . ?
C3 C4 1.548(5) . ?
C4 C18 1.523(7) . ?
C4 C5 1.525(5) . ?
C5 C6 1.519(6) . ?
C6 C7 1.519(5) . ?
C7 C8 1.537(6) . ?
C8 C19 1.518(6) . ?
C8 C9 1.529(6) . ?
C9 C10 1.526(7) . ?
C10 C11 1.521(6) . ?
C11 C12 1.529(6) . ?
C12 C20 1.520(6) . ?
C12 C13 1.542(6) . ?
C13 C14 1.536(5) . ?
C15 C17 1.525(6) . ?
C15 C16 1.529(6) . ?
Cl2 C27 1.811(4) . ?
O5 C23 1.427(5) . ?
O6 C24 1.445(5) . ?
O7 C28 1.455(5) . ?
O7 C31 1.458(5) . ?
O8 C32 1.423(5) . ?
C21 C22 1.338(6) . ?
C21 C34 1.514(6) . ?
C21 C35 1.526(6) . ?
C22 C23 1.495(6) . ?
C23 C24 1.547(6) . ?
C24 C25 1.517(6) . ?
C24 C38 1.521(6) . ?
C25 C26 1.526(5) . ?
C26 C27 1.519(6) . ?
C27 C28 1.545(6) . ?
C28 C39 1.510(7) . ?
C28 C29 1.526(6) . ?
C29 C30 1.527(8) . ?
C30 C31 1.509(6) . ?
C31 C32 1.525(7) . ?
C32 C40 1.528(7) . ?
C32 C33 1.544(6) . ?
C33 C34 1.530(6) . ?
C35 C36 1.523(7) . ?
C35 C37 1.531(7) . ?

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 O3 C8 111.3(3) . . ?
C2 C1 C14 123.7(4) . . ?
C2 C1 C15 118.7(4) . . ?
C14 C1 C15 117.6(3) . . ?
C1 C2 C3 127.8(4) . . ?
O1 C3 C2 110.8(3) . . ?
O1 C3 C4 103.5(3) . . ?
C2 C3 C4 115.3(4) . . ?
O2 C4 C18 109.0(4) . . ?
O2 C4 C5 107.2(3) . . ?
C18 C4 C5 109.7(4) . . ?
O2 C4 C3 106.1(3) . . ?
C18 C4 C3 112.3(3) . . ?
C5 C4 C3 112.3(3) . . ?
C6 C5 C4 116.2(4) . . ?
C5 C6 C7 111.7(3) . . ?
C6 C7 C8 116.5(3) . . ?
C6 C7 Cl1 109.1(3) . . ?
C8 C7 Cl1 110.0(3) . . ?
O3 C8 C19 108.0(4) . . ?
O3 C8 C9 103.6(3) . . ?
C19 C8 C9 114.9(4) . . ?
O3 C8 C7 105.2(3) . . ?
C19 C8 C7 113.4(4) . . ?
C9 C8 C7 110.8(4) . . ?
C10 C9 C8 103.4(3) . . ?
C11 C10 C9 101.7(4) . . ?
O3 C11 C10 105.5(3) . . ?
O3 C11 C12 108.8(3) . . ?
C10 C11 C12 118.3(3) . . ?
O4 C12 C20 104.6(3) . . ?
O4 C12 C11 107.8(3) . . ?
C20 C12 C11 110.1(4) . . ?
O4 C12 C13 110.6(3) . . ?
C20 C12 C13 111.9(3) . . ?
C11 C12 C13 111.5(3) . . ?
C14 C13 C12 116.0(3) . . ?
C1 C14 C13 111.3(3) . . ?
C1 C15 C17 113.6(4) . . ?
C1 C15 C16 110.4(4) . . ?
C17 C15 C16 109.6(4) . . ?
C28 O7 C31 111.4(3) . . ?
C22 C21 C34 123.5(4) . . ?
C22 C21 C35 121.9(4) . . ?
C34 C21 C35 114.6(4) . . ?
C21 C22 C23 127.5(4) . . ?
O5 C23 C22 111.2(3) . . ?
O5 C23 C24 104.3(3) . . ?
C22 C23 C24 114.3(4) . . ?
O6 C24 C25 108.0(3) . . ?
O6 C24 C38 108.6(3) . . ?
C25 C24 C38 109.9(4) . . ?
O6 C24 C23 105.3(3) . . ?
C25 C24 C23 112.8(3) . . ?
C38 C24 C23 112.0(4) . . ?
C24 C25 C26 116.8(3) . . ?
C27 C26 C25 111.8(3) . . ?
C26 C27 C28 116.1(3) . . ?
C26 C27 Cl2 109.6(3) . . ?
C28 C27 Cl2 109.3(3) . . ?
O7 C28 C39 107.1(4) . . ?
O7 C28 C29 103.5(4) . . ?
C39 C28 C29 115.1(4) . . ?
O7 C28 C27 105.6(3) . . ?
C39 C28 C27 113.5(4) . . ?
C29 C28 C27 111.0(4) . . ?
C28 C29 C30 103.6(4) . . ?
C31 C30 C29 102.5(4) . . ?
O7 C31 C30 105.0(4) . . ?
O7 C31 C32 108.8(3) . . ?
C30 C31 C32 119.3(4) . . ?
O8 C32 C31 108.9(4) . . ?
O8 C32 C40 105.0(4) . . ?
C31 C32 C40 109.4(4) . . ?
O8 C32 C33 111.3(4) . . ?
C31 C32 C33 111.3(4) . . ?
C40 C32 C33 110.7(4) . . ?
C34 C33 C32 115.4(4) . . ?
C21 C34 C33 110.5(4) . . ?
C36 C35 C21 114.8(4) . . ?
C36 C35 C37 110.3(4) . . ?
C21 C35 C37 108.5(4) . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ic21808
_database_code_depnum_ccdc_archive 'CCDC 2226689'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2022-12-15 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        sinulariaone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 O2'
_chemical_formula_weight         304.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.0173(3)
_cell_length_b                   10.8659(3)
_cell_length_c                   18.6542(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1827.76(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8431
_cell_measurement_theta_min      4.1400
_cell_measurement_theta_max      78.3640

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.484
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.02697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            18147
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.710
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3472
_reflns_number_gt                3095
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6436(3) 0.2552(2) 0.53923(14) 0.0303(6) Uani 1 1 d . . . . .
O2 O 0.9634(3) 0.5825(3) 0.26508(16) 0.0417(7) Uani 1 1 d . . . . .
C1 C 0.4973(4) 0.5544(3) 0.34973(19) 0.0249(7) Uani 1 1 d . . . . .
C2 C 0.6269(4) 0.5845(3) 0.31877(19) 0.0273(7) Uani 1 1 d . . . . .
H2A H 0.6248 0.6053 0.2693 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7757(4) 0.5881(3) 0.35611(19) 0.0252(7) Uani 1 1 d . . . . .
H3A H 0.7681 0.5392 0.4014 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8224(4) 0.7198(3) 0.3756(2) 0.0307(8) Uani 1 1 d . . . . .
H4A H 0.7340 0.7671 0.3909 0.037 Uiso 1 1 calc R U . . .
H4B H 0.8646 0.7607 0.3328 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9376(4) 0.7204(3) 0.4361(2) 0.0296(8) Uani 1 1 d . . . . .
H5A H 1.0215 0.6661 0.4230 0.036 Uiso 1 1 calc R U . . .
H5B H 0.9766 0.8049 0.4425 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8698(4) 0.6767(3) 0.50527(19) 0.0272(7) Uani 1 1 d . . . . .
H6A H 0.7805 0.7166 0.5191 0.033 Uiso 1 1 calc R U . . .
C7 C 0.9179(4) 0.5896(3) 0.5498(2) 0.0275(7) Uani 1 1 d . . . . .
C8 C 0.8238(4) 0.5509(3) 0.61305(19) 0.0285(7) Uani 1 1 d . . . . .
H8A H 0.7311 0.5998 0.6129 0.034 Uiso 1 1 calc R U . . .
H8B H 0.8779 0.5704 0.6578 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7835(4) 0.4126(3) 0.61314(19) 0.0290(7) Uani 1 1 d . . . . .
H9A H 0.8733 0.3635 0.6237 0.035 Uiso 1 1 calc R U . . .
H9B H 0.7099 0.3963 0.6514 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7203(4) 0.3730(3) 0.5419(2) 0.0264(7) Uani 1 1 d . . . . .
H10A H 0.7863 0.3895 0.4999 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5614(4) 0.3682(3) 0.52456(19) 0.0266(7) Uani 1 1 d . . . . .
C12 C 0.5198(4) 0.3839(3) 0.44637(19) 0.0278(7) Uani 1 1 d . . . . .
H12A H 0.4303 0.3343 0.4358 0.033 Uiso 1 1 calc R U . . .
H12B H 0.6015 0.3531 0.4158 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4888(4) 0.5212(3) 0.42818(18) 0.0267(7) Uani 1 1 d . . . . .
H13A H 0.3885 0.5425 0.4459 0.032 Uiso 1 1 calc R U . . .
H13B H 0.5608 0.5727 0.4547 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3514(4) 0.5551(3) 0.3087(2) 0.0295(8) Uani 1 1 d . . . . .
H14A H 0.2758 0.5944 0.3405 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3540(5) 0.6278(4) 0.2399(2) 0.0415(10) Uani 1 1 d . . . . .
H15A H 0.2564 0.6236 0.2169 0.062 Uiso 1 1 calc R U . . .
H15B H 0.3784 0.7139 0.2504 0.062 Uiso 1 1 calc R U . . .
H15C H 0.4290 0.5933 0.2076 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2994(5) 0.4235(4) 0.2945(3) 0.0467(11) Uani 1 1 d . . . . .
H16A H 0.2983 0.3774 0.3396 0.070 Uiso 1 1 calc R U . . .
H16B H 0.1993 0.4252 0.2740 0.070 Uiso 1 1 calc R U . . .
H16C H 0.3673 0.3837 0.2607 0.070 Uiso 1 1 calc R U . . .
C17 C 0.8882(4) 0.5249(3) 0.30677(19) 0.0282(7) Uani 1 1 d . . . . .
C18 C 0.8970(5) 0.3871(4) 0.3127(3) 0.0492(12) Uani 1 1 d . . . . .
H18A H 0.8274 0.3585 0.3494 0.074 Uiso 1 1 calc R U . . .
H18B H 0.8712 0.3500 0.2664 0.074 Uiso 1 1 calc R U . . .
H18C H 0.9980 0.3630 0.3260 0.074 Uiso 1 1 calc R U . . .
C19 C 1.0632(4) 0.5232(3) 0.5417(2) 0.0347(8) Uani 1 1 d . . . . .
H19A H 1.0744 0.4634 0.5806 0.052 Uiso 1 1 calc R U . . .
H19B H 1.0652 0.4801 0.4955 0.052 Uiso 1 1 calc R U . . .
H19C H 1.1447 0.5828 0.5435 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4423(4) 0.3978(3) 0.5779(2) 0.0312(8) Uani 1 1 d . . . . .
H20A H 0.3930 0.4746 0.5641 0.047 Uiso 1 1 calc R U . . .
H20B H 0.3695 0.3308 0.5789 0.047 Uiso 1 1 calc R U . . .
H20C H 0.4865 0.4072 0.6256 0.047 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 1.460(4) . ?
O1 C10 1.456(4) . ?
O2 C17 1.207(5) . ?
C1 C2 1.343(5) . ?
C1 C13 1.509(5) . ?
C1 C14 1.522(5) . ?
C2 C3 1.513(5) . ?
C3 C4 1.536(4) . ?
C3 C17 1.533(5) . ?
C4 C5 1.533(5) . ?
C5 C6 1.505(5) . ?
C6 C7 1.331(5) . ?
C7 C8 1.513(5) . ?
C7 C19 1.504(5) . ?
C8 C9 1.547(4) . ?
C9 C10 1.508(5) . ?
C10 C11 1.470(5) . ?
C11 C20 1.499(5) . ?
C11 C12 1.516(5) . ?
C12 C13 1.556(4) . ?
C14 C15 1.507(5) . ?
C14 C16 1.528(5) . ?
C17 C18 1.503(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 60.5(2) . . ?
C2 C1 C13 121.3(3) . . ?
C2 C1 C14 122.3(3) . . ?
C13 C1 C14 116.4(3) . . ?
C1 C2 C3 125.4(3) . . ?
C2 C3 C4 112.1(3) . . ?
C2 C3 C17 107.4(3) . . ?
C4 C3 C17 112.3(3) . . ?
C3 C4 C5 111.4(3) . . ?
C6 C5 C4 110.7(3) . . ?
C7 C6 C5 128.8(3) . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 C19 124.2(4) . . ?
C8 C7 C19 115.7(3) . . ?
C7 C8 C9 113.7(3) . . ?
C10 C9 C8 111.4(3) . . ?
O1 C10 C11 59.9(2) . . ?
O1 C10 C9 117.4(3) . . ?
C11 C10 C9 124.9(3) . . ?
O1 C11 C10 59.6(2) . . ?
O1 C11 C20 114.8(3) . . ?
C10 C11 C20 123.0(3) . . ?
O1 C11 C12 113.6(3) . . ?
C10 C11 C12 116.7(3) . . ?
C20 C11 C12 115.9(3) . . ?
C11 C12 C13 111.2(3) . . ?
C1 C13 C12 115.6(3) . . ?
C15 C14 C1 114.7(3) . . ?
C15 C14 C16 110.3(3) . . ?
C1 C14 C16 110.3(3) . . ?
O2 C17 C18 122.3(4) . . ?
O2 C17 C3 121.8(3) . . ?
C18 C17 C3 115.9(3) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.061



