# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_11738
_database_code_depnum_ccdc_archive 'CCDC 2080924'
loop_
_audit_author_name
_audit_author_address
'bingwen zhang' 'Hebei Uniersity'
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 O3'
_chemical_formula_weight         270.40

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                   6.42709(19)
_cell_length_b                   8.2638(2)
_cell_length_c                   30.7804(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1634.81(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3485
_cell_measurement_theta_min      6.8780
_cell_measurement_theta_max      70.9100

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.580
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_T_min  0.87293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5857
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         5.543
_diffrn_reflns_theta_max         67.227
_diffrn_reflns_theta_full        67.227
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2921
_reflns_number_gt                2784
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+0.2502P] 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 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(11)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2921
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.6561(3) -0.1563(2) 0.09873(6) 0.0492(4) Uani 1 1 d . . . . .
H1 H 0.532901 -0.158858 0.105584 0.074 Uiso 1 1 calc R U . . .
O2 O 0.9339(3) 0.6404(2) 0.13606(8) 0.0667(6) Uani 1 1 d . . . . .
H2 H 0.834883 0.683733 0.123927 0.100 Uiso 1 1 calc R U . . .
O3 O 0.2895(4) 0.8119(4) 0.14105(8) 0.0862(8) Uani 1 1 d . . . . .
H3 H 0.193321 0.747479 0.138458 0.129 Uiso 1 1 calc R U . . .
C1 C 0.8744(4) 0.4822(3) 0.15058(9) 0.0468(6) Uani 1 1 d . . . . .
H1A H 0.740725 0.490647 0.165713 0.056 Uiso 1 1 calc R U . . .
C2 C 1.0384(5) 0.4338(3) 0.18307(9) 0.0559(7) Uani 1 1 d . . . . .
H2A H 1.145616 0.507688 0.187352 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0485(5) 0.3002(3) 0.20610(8) 0.0524(6) Uani 1 1 d . . . . .
C4 C 0.8867(5) 0.1687(4) 0.20338(8) 0.0585(7) Uani 1 1 d . . . . .
H4A H 0.754718 0.212442 0.213143 0.070 Uiso 1 1 calc R U . . .
H4B H 0.925235 0.082671 0.223267 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8563(5) 0.0954(3) 0.15802(7) 0.0467(6) Uani 1 1 d . . . . .
H5A H 0.991516 0.072213 0.145472 0.056 Uiso 1 1 calc R U . . .
H5B H 0.781778 -0.006169 0.160728 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7368(3) 0.2065(3) 0.12754(7) 0.0349(5) Uani 1 1 d . . . . .
H6 H 0.622056 0.246803 0.145502 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6247(4) 0.1343(3) 0.08654(7) 0.0372(5) Uani 1 1 d . . . . .
H7 H 0.478571 0.121973 0.094990 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6278(4) 0.2747(3) 0.05314(8) 0.0467(6) Uani 1 1 d . . . . .
H8A H 0.726624 0.252441 0.030084 0.056 Uiso 1 1 calc R U . . .
H8B H 0.491102 0.289520 0.040377 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6924(4) 0.4253(3) 0.07855(8) 0.0458(6) Uani 1 1 d . . . . .
H9A H 0.573205 0.474355 0.092675 0.055 Uiso 1 1 calc R U . . .
H9B H 0.756407 0.504453 0.059507 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8492(3) 0.3633(3) 0.11226(7) 0.0380(5) Uani 1 1 d . . . . .
C11 C 1.2255(6) 0.2705(4) 0.23725(11) 0.0746(10) Uani 1 1 d . . . . .
H11A H 1.318774 0.361185 0.236749 0.112 Uiso 1 1 calc R U . . .
H11B H 1.299149 0.174453 0.228760 0.112 Uiso 1 1 calc R U . . .
H11C H 1.171342 0.256784 0.266086 0.112 Uiso 1 1 calc R U . . .
C12 C 0.6887(4) -0.0307(3) 0.06710(7) 0.0425(5) Uani 1 1 d . . . . .
C13 C 0.5477(6) -0.0677(4) 0.02811(10) 0.0693(9) Uani 1 1 d . . . . .
H13A H 0.571929 -0.176469 0.018418 0.104 Uiso 1 1 calc R U . . .
H13B H 0.578140 0.006417 0.004949 0.104 Uiso 1 1 calc R U . . .
H13C H 0.404671 -0.056091 0.036577 0.104 Uiso 1 1 calc R U . . .
C14 C 0.9159(5) -0.0478(3) 0.05395(9) 0.0551(7) Uani 1 1 d . . . . .
H14A H 1.003200 -0.024253 0.078453 0.083 Uiso 1 1 calc R U . . .
H14B H 0.946296 0.026521 0.030840 0.083 Uiso 1 1 calc R U . . .
H14C H 0.941412 -0.156426 0.044273 0.083 Uiso 1 1 calc R U . . .
C15 C 1.0618(4) 0.3355(4) 0.09115(9) 0.0526(6) Uani 1 1 d . . . . .
H15A H 1.122619 0.437895 0.083664 0.079 Uiso 1 1 calc R U . . .
H15B H 1.044975 0.271460 0.065375 0.079 Uiso 1 1 calc R U . . .
H15C H 1.151099 0.279799 0.111178 0.079 Uiso 1 1 calc R U . . .
C16 C 0.3357(6) 0.8315(5) 0.18436(12) 0.0863(11) Uani 1 1 d . . . . .
H16A H 0.419416 0.926681 0.188100 0.129 Uiso 1 1 calc R U . . .
H16B H 0.410857 0.738656 0.194621 0.129 Uiso 1 1 calc R U . . .
H16C H 0.209002 0.842793 0.200605 0.129 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 C12 1.438(3) . ?
O2 C1 1.434(3) . ?
O3 C16 1.375(4) . ?
C1 C2 1.507(4) . ?
C1 C10 1.543(3) . ?
C2 C3 1.314(4) . ?
C3 C4 1.506(4) . ?
C3 C11 1.508(4) . ?
C4 C5 1.535(3) . ?
C5 C6 1.521(3) . ?
C6 C10 1.556(3) . ?
C6 C7 1.571(3) . ?
C7 C12 1.545(3) . ?
C7 C8 1.551(3) . ?
C8 C9 1.527(3) . ?
C9 C10 1.534(3) . ?
C10 C15 1.530(3) . ?
C12 C14 1.522(4) . ?
C12 C13 1.535(4) . ?

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
O2 C1 C2 105.2(2) . . ?
O2 C1 C10 111.7(2) . . ?
C2 C1 C10 114.3(2) . . ?
C3 C2 C1 128.0(3) . . ?
C2 C3 C4 122.8(3) . . ?
C2 C3 C11 121.2(3) . . ?
C4 C3 C11 116.0(2) . . ?
C3 C4 C5 115.0(2) . . ?
C6 C5 C4 112.8(2) . . ?
C5 C6 C10 117.04(19) . . ?
C5 C6 C7 119.85(18) . . ?
C10 C6 C7 106.64(17) . . ?
C12 C7 C8 113.60(19) . . ?
C12 C7 C6 121.63(19) . . ?
C8 C7 C6 104.04(17) . . ?
C9 C8 C7 105.86(18) . . ?
C8 C9 C10 104.68(18) . . ?
C15 C10 C9 110.45(19) . . ?
C15 C10 C1 109.0(2) . . ?
C9 C10 C1 111.93(19) . . ?
C15 C10 C6 114.7(2) . . ?
C9 C10 C6 100.20(18) . . ?
C1 C10 C6 110.34(18) . . ?
O1 C12 C14 104.6(2) . . ?
O1 C12 C13 107.5(2) . . ?
C14 C12 C13 109.9(2) . . ?
O1 C12 C7 109.63(18) . . ?
C14 C12 C7 116.1(2) . . ?
C13 C12 C7 108.7(2) . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034

