# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_RDP612_20211201
_database_code_depnum_ccdc_archive 'CCDC 2195138'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         250.32
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.9836(2)
_cell_length_b                   12.5695(4)
_cell_length_c                   17.9850(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1352.67(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6271
_cell_measurement_theta_min      4.2913
_cell_measurement_theta_max      68.2827
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            8192
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_full        68.28
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             2458
_reflns_number_gt                2391
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0698
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         2458
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.2212P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.8670(2) 0.20901(9) 0.53210(7) 0.0257(3) Uani d . . . 1 . .
O O3 0.9707(2) 0.57209(10) 0.56388(7) 0.0224(3) Uani d . . . 1 . .
H H22 1.091(4) 0.5433(18) 0.5629(12) 0.028(6) Uiso d . . . 1 . .
O O4 0.39888(18) 0.46948(10) 0.56287(7) 0.0219(3) Uani d . . . 1 . .
H H21 0.417(4) 0.428(2) 0.5279(14) 0.034(6) Uiso d . . . 1 . .
C C1 0.8564(3) 0.30540(14) 0.52241(9) 0.0206(3) Uani d . . . 1 . .
C C2 0.8487(3) 0.36176(14) 0.45120(9) 0.0208(3) Uani d . . . 1 . .
C C3 0.8195(2) 0.46633(13) 0.46337(9) 0.0180(3) Uani d . . . 1 . .
C C4 0.7906(3) 0.54741(14) 0.40335(9) 0.0203(3) Uani d . . . 1 . .
H H6 0.869518 0.524172 0.357775 0.024 Uiso calc U . R 1 . .
H H5 0.854562 0.61633 0.419378 0.024 Uiso calc U . R 1 . .
C C5 0.5379(3) 0.56017(14) 0.38723(9) 0.0213(4) Uani d . . . 1 . .
H H9 0.468582 0.487907 0.390287 0.026 Uiso calc U . R 1 . .
C C6 0.4914(3) 0.60350(16) 0.31005(9) 0.0263(4) Uani d . . . 1 . .
C C7 0.6131(4) 0.70239(17) 0.28719(10) 0.0343(4) Uani d . . . 1 . .
H H7 0.773271 0.687118 0.283123 0.051 Uiso calc U . R 1 . .
H H8 0.58927 0.758041 0.324515 0.051 Uiso calc U . R 1 . .
H H1 0.556466 0.726694 0.238965 0.051 Uiso calc U . R 1 . .
C C8 0.8658(3) 0.30608(15) 0.37785(10) 0.0278(4) Uani d . . . 1 . .
H H4 0.747486 0.331727 0.344688 0.042 Uiso calc U . R 1 . .
H H3 0.848978 0.229254 0.38529 0.042 Uiso calc U . R 1 . .
H H2 1.011948 0.32079 0.355537 0.042 Uiso calc U . R 1 . .
C C9 0.4191(3) 0.63175(15) 0.44516(9) 0.0252(4) Uani d . . . 1 . .
H H18 0.40385 0.703547 0.423104 0.03 Uiso calc U . R 1 . .
H H10 0.266179 0.603507 0.452251 0.03 Uiso calc U . R 1 . .
C C10 0.5241(3) 0.64488(14) 0.52206(9) 0.0212(3) Uani d . . . 1 . .
H H17 0.422729 0.690172 0.551886 0.025 Uiso calc U . R 1 . .
H H11 0.665172 0.685038 0.515673 0.025 Uiso calc U . R 1 . .
C C11 0.5774(3) 0.54564(13) 0.56843(9) 0.0183(3) Uani d . . . 1 . .
C C12 0.8051(2) 0.49423(13) 0.54587(9) 0.0180(3) Uani d . . . 1 . .
C C13 0.8450(3) 0.38648(13) 0.58430(9) 0.0213(3) Uani d . . . 1 . .
H H12 0.98665 0.387631 0.612738 0.026 Uiso calc U . R 1 . .
H H13 0.720948 0.369733 0.618788 0.026 Uiso calc U . R 1 . .
C C14 0.5862(3) 0.57737(14) 0.65055(9) 0.0240(4) Uani d . . . 1 . .
H H14 0.43646 0.598133 0.667217 0.036 Uiso calc U . R 1 . .
H H16 0.688959 0.637395 0.656837 0.036 Uiso calc U . R 1 . .
H H15 0.638664 0.516887 0.680172 0.036 Uiso calc U . R 1 . .
C C15 0.3419(4) 0.5559(2) 0.26697(11) 0.0415(5) Uani d . . . 1 . .
H H20 0.267(5) 0.485(2) 0.2828(15) 0.050(7) Uiso d . . . 1 . .
H H19 0.301(4) 0.585(2) 0.2180(14) 0.045(7) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.226(2) ?
O3 C12 . 1.4299(19) ?
O3 H22 . 0.81(2) ?
O4 C11 . 1.4380(19) ?
O4 H21 . 0.82(3) ?
C1 C2 . 1.464(2) ?
C1 C13 . 1.511(2) ?
C2 C3 . 1.344(2) ?
C2 C8 . 1.497(2) ?
C3 C4 . 1.495(2) ?
C3 C12 . 1.527(2) ?
C4 C5 . 1.548(2) ?
C4 H6 . 0.99 ?
C4 H5 . 0.99 ?
C5 C6 . 1.517(2) ?
C5 C9 . 1.549(2) ?
C5 H9 . 1.0 ?
C6 C15 . 1.326(3) ?
C6 C7 . 1.498(3) ?
C7 H7 . 0.98 ?
C7 H8 . 0.98 ?
C7 H1 . 0.98 ?
C8 H4 . 0.98 ?
C8 H3 . 0.98 ?
C8 H2 . 0.98 ?
C9 C10 . 1.528(2) ?
C9 H18 . 0.99 ?
C9 H10 . 0.99 ?
C10 C11 . 1.534(2) ?
C10 H17 . 0.99 ?
C10 H11 . 0.99 ?
C11 C14 . 1.531(2) ?
C11 C12 . 1.561(2) ?
C12 C13 . 1.539(2) ?
C13 H12 . 0.99 ?
C13 H13 . 0.99 ?
C14 H14 . 0.98 ?
C14 H16 . 0.98 ?
C14 H15 . 0.98 ?
C15 H20 . 1.04(3) ?
C15 H19 . 0.99(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O3 H22 . . 107.9(16) ?
C11 O4 H21 . . 112.0(17) ?
O1 C1 C2 . . 127.17(16) ?
O1 C1 C13 . . 124.36(16) ?
C2 C1 C13 . . 108.46(14) ?
C3 C2 C1 . . 109.56(15) ?
C3 C2 C8 . . 127.57(16) ?
C1 C2 C8 . . 122.85(15) ?
C2 C3 C4 . . 124.36(15) ?
C2 C3 C12 . . 112.97(15) ?
C4 C3 C12 . . 122.59(14) ?
C3 C4 C5 . . 108.60(13) ?
C3 C4 H6 . . 110.0 ?
C5 C4 H6 . . 110.0 ?
C3 C4 H5 . . 110.0 ?
C5 C4 H5 . . 110.0 ?
H6 C4 H5 . . 108.4 ?
C6 C5 C4 . . 112.81(14) ?
C6 C5 C9 . . 108.84(14) ?
C4 C5 C9 . . 112.47(14) ?
C6 C5 H9 . . 107.5 ?
C4 C5 H9 . . 107.5 ?
C9 C5 H9 . . 107.5 ?
C15 C6 C7 . . 122.79(18) ?
C15 C6 C5 . . 119.78(18) ?
C7 C6 C5 . . 117.38(16) ?
C6 C7 H7 . . 109.5 ?
C6 C7 H8 . . 109.5 ?
H7 C7 H8 . . 109.5 ?
C6 C7 H1 . . 109.5 ?
H7 C7 H1 . . 109.5 ?
H8 C7 H1 . . 109.5 ?
C2 C8 H4 . . 109.5 ?
C2 C8 H3 . . 109.5 ?
H4 C8 H3 . . 109.5 ?
C2 C8 H2 . . 109.5 ?
H4 C8 H2 . . 109.5 ?
H3 C8 H2 . . 109.5 ?
C10 C9 C5 . . 118.88(14) ?
C10 C9 H18 . . 107.6 ?
C5 C9 H18 . . 107.6 ?
C10 C9 H10 . . 107.6 ?
C5 C9 H10 . . 107.6 ?
H18 C9 H10 . . 107.0 ?
C9 C10 C11 . . 119.32(14) ?
C9 C10 H17 . . 107.5 ?
C11 C10 H17 . . 107.5 ?
C9 C10 H11 . . 107.5 ?
C11 C10 H11 . . 107.5 ?
H17 C10 H11 . . 107.0 ?
O4 C11 C14 . . 105.42(13) ?
O4 C11 C10 . . 110.43(12) ?
C14 C11 C10 . . 108.65(13) ?
O4 C11 C12 . . 110.77(12) ?
C14 C11 C12 . . 109.20(13) ?
C10 C11 C12 . . 112.13(13) ?
O3 C12 C3 . . 109.76(13) ?
O3 C12 C13 . . 113.14(13) ?
C3 C12 C13 . . 103.03(13) ?
O3 C12 C11 . . 105.21(12) ?
C3 C12 C11 . . 113.38(13) ?
C13 C12 C11 . . 112.52(13) ?
C1 C13 C12 . . 105.65(13) ?
C1 C13 H12 . . 110.6 ?
C12 C13 H12 . . 110.6 ?
C1 C13 H13 . . 110.6 ?
C12 C13 H13 . . 110.6 ?
H12 C13 H13 . . 108.7 ?
C11 C14 H14 . . 109.5 ?
C11 C14 H16 . . 109.5 ?
H14 C14 H16 . . 109.5 ?
C11 C14 H15 . . 109.5 ?
H14 C14 H15 . . 109.5 ?
H16 C14 H15 . . 109.5 ?
C6 C15 H20 . . 121.2(16) ?
C6 C15 H19 . . 121.5(16) ?
H20 C15 H19 . . 117.(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 175.07(17) ?
C13 C1 C2 C3 . . . . -3.98(18) ?
O1 C1 C2 C8 . . . . -3.4(3) ?
C13 C1 C2 C8 . . . . 177.51(15) ?
C1 C2 C3 C4 . . . . -176.29(14) ?
C8 C2 C3 C4 . . . . 2.1(3) ?
C1 C2 C3 C12 . . . . 0.40(18) ?
C8 C2 C3 C12 . . . . 178.82(16) ?
C2 C3 C4 C5 . . . . 91.32(18) ?
C12 C3 C4 C5 . . . . -85.06(18) ?
C3 C4 C5 C6 . . . . -156.86(14) ?
C3 C4 C5 C9 . . . . 79.57(18) ?
C4 C5 C6 C15 . . . . 131.4(2) ?
C9 C5 C6 C15 . . . . -103.0(2) ?
C4 C5 C6 C7 . . . . -50.9(2) ?
C9 C5 C6 C7 . . . . 74.6(2) ?
C6 C5 C9 C10 . . . . -148.82(16) ?
C4 C5 C9 C10 . . . . -23.1(2) ?
C5 C9 C10 C11 . . . . -54.9(2) ?
C9 C10 C11 O4 . . . . -41.57(19) ?
C9 C10 C11 C14 . . . . -156.73(14) ?
C9 C10 C11 C12 . . . . 82.48(18) ?
C2 C3 C12 O3 . . . . 123.97(14) ?
C4 C3 C12 O3 . . . . -59.28(18) ?
C2 C3 C12 C13 . . . . 3.19(17) ?
C4 C3 C12 C13 . . . . 179.94(14) ?
C2 C3 C12 C11 . . . . -118.70(15) ?
C4 C3 C12 C11 . . . . 58.05(19) ?
O4 C11 C12 O3 . . . . -171.88(12) ?
C14 C11 C12 O3 . . . . -56.21(17) ?
C10 C11 C12 O3 . . . . 64.26(16) ?
O4 C11 C12 C3 . . . . 68.17(17) ?
C14 C11 C12 C3 . . . . -176.17(14) ?
C10 C11 C12 C3 . . . . -55.70(18) ?
O4 C11 C12 C13 . . . . -48.26(17) ?
C14 C11 C12 C13 . . . . 67.41(17) ?
C10 C11 C12 C13 . . . . -172.13(13) ?
O1 C1 C13 C12 . . . . -173.29(16) ?
C2 C1 C13 C12 . . . . 5.80(17) ?
O3 C12 C13 C1 . . . . -123.71(14) ?
C3 C12 C13 C1 . . . . -5.26(16) ?
C11 C12 C13 C1 . . . . 117.20(14) ?

####################################################################### 
# 
# 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_RDP88B_20201127
_database_code_depnum_ccdc_archive 'CCDC 2195140'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         236.30
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.1817(2)
_cell_length_b                   9.2698(4)
_cell_length_c                   27.2715(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1309.94(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5488
_cell_measurement_theta_min      3.2410
_cell_measurement_theta_max      53.7423
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            6483
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         53.74
_diffrn_reflns_theta_full        53.74
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             1574
_reflns_number_gt                1530
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0634
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_number_reflns         1574
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.1709P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 592 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5429(3) 0.69390(17) 0.68429(5) 0.0328(4) Uani d . . . 1 . .
O O2 1.0854(3) 0.29707(17) 0.65443(5) 0.0269(4) Uani d . . . 1 . .
H H2A 1.193081 0.298781 0.677459 0.04 Uiso calc U . R 1 . .
O O3 0.4781(3) 0.28810(16) 0.72201(5) 0.0240(4) Uani d . . . 1 . .
H H3A 0.444014 0.262342 0.75082 0.036 Uiso calc U . R 1 . .
C C1 0.8118(5) -0.1332(3) 0.55470(10) 0.0429(6) Uani d . . . 1 . .
H H11 0.751588 -0.196196 0.528218 0.064 Uiso calc U . R 1 . .
H H10 0.7953 -0.183485 0.586148 0.064 Uiso calc U . R 1 . .
H H1 0.993142 -0.107933 0.549122 0.064 Uiso calc U . R 1 . .
C C2 0.6513(4) 0.0022(2) 0.55564(8) 0.0289(5) Uani d . . . 1 . .
C C3 0.7094(4) 0.1025(2) 0.59822(8) 0.0238(5) Uani d . . . 1 . .
H H9 0.900303 0.101505 0.60356 0.029 Uiso calc U . R 1 . .
C C4 0.6301(4) 0.2587(2) 0.58767(7) 0.0247(5) Uani d . . . 1 . .
H H14 0.725155 0.291 0.558162 0.03 Uiso calc U . R 1 . .
H H15 0.444272 0.258726 0.579207 0.03 Uiso calc U . R 1 . .
C C5 0.6710(4) 0.3688(2) 0.62692(7) 0.0193(5) Uani d . . . 1 . .
C C6 0.5592(4) 0.4996(2) 0.62672(7) 0.0214(5) Uani d . . . 1 . .
C C7 0.3704(5) 0.5585(2) 0.59038(8) 0.0299(5) Uani d . . . 1 . .
H H3B 0.442046 0.549851 0.557249 0.045 Uiso calc U . R 1 . .
H H4 0.336798 0.660308 0.597671 0.045 Uiso calc U . R 1 . .
H H2B 0.20876 0.503971 0.5924 0.045 Uiso calc U . R 1 . .
C C8 0.6383(4) 0.5793(2) 0.67020(7) 0.0229(5) Uani d . . . 1 . .
C C9 0.8421(4) 0.3465(2) 0.67181(7) 0.0218(5) Uani d . . . 1 . .
C C10 0.7313(4) 0.2376(2) 0.70881(8) 0.0220(5) Uani d . . . 1 . .
H H5 0.840857 0.242637 0.73895 0.026 Uiso calc U . R 1 . .
C C11 0.7273(4) 0.0807(2) 0.69226(8) 0.0265(5) Uani d . . . 1 . .
H H7 0.651913 0.022407 0.719087 0.032 Uiso calc U . R 1 . .
H H6 0.908178 0.048703 0.688026 0.032 Uiso calc U . R 1 . .
C C12 0.5813(4) 0.0454(2) 0.64532(8) 0.0258(5) Uani d . . . 1 . .
H H16 0.405305 0.086448 0.647702 0.031 Uiso calc U . R 1 . .
H H8 0.563876 -0.060631 0.642672 0.031 Uiso calc U . R 1 . .
C C13 0.4730(5) 0.0265(3) 0.52191(9) 0.0400(6) Uani d . . . 1 . .
H H13 0.444599 -0.042048 0.496577 0.048 Uiso calc U . R 1 . .
H H12 0.37329 0.112434 0.523026 0.048 Uiso calc U . R 1 . .
C C14 0.8515(4) 0.4982(2) 0.69504(7) 0.0250(5) Uani d . . . 1 . .
H H18 0.821953 0.493051 0.730864 0.03 Uiso calc U . R 1 . .
H H17 1.020357 0.544811 0.68892 0.03 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.233(3) ?
O2 C9 . 1.423(3) ?
O2 H2A . 0.84 ?
O3 C10 . 1.439(2) ?
O3 H3A . 0.84 ?
C1 C2 . 1.506(3) ?
C1 H11 . 0.98 ?
C1 H10 . 0.98 ?
C1 H1 . 0.98 ?
C2 C13 . 1.323(4) ?
C2 C3 . 1.518(3) ?
C3 C4 . 1.532(3) ?
C3 C12 . 1.540(3) ?
C3 H9 . 1.0 ?
C4 C5 . 1.494(3) ?
C4 H14 . 0.99 ?
C4 H15 . 0.99 ?
C5 C6 . 1.344(3) ?
C5 C9 . 1.526(3) ?
C6 C8 . 1.456(3) ?
C6 C7 . 1.496(3) ?
C7 H3B . 0.98 ?
C7 H4 . 0.98 ?
C7 H2B . 0.98 ?
C8 C14 . 1.498(3) ?
C9 C10 . 1.539(3) ?
C9 C14 . 1.543(3) ?
C10 C11 . 1.522(3) ?
C10 H5 . 1.0 ?
C11 C12 . 1.523(3) ?
C11 H7 . 0.99 ?
C11 H6 . 0.99 ?
C12 H16 . 0.99 ?
C12 H8 . 0.99 ?
C13 H13 . 0.95 ?
C13 H12 . 0.95 ?
C14 H18 . 0.99 ?
C14 H17 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O2 H2A . . 109.5 ?
C10 O3 H3A . . 109.5 ?
C2 C1 H11 . . 109.5 ?
C2 C1 H10 . . 109.5 ?
H11 C1 H10 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H11 C1 H1 . . 109.5 ?
H10 C1 H1 . . 109.5 ?
C13 C2 C1 . . 121.0(2) ?
C13 C2 C3 . . 124.5(2) ?
C1 C2 C3 . . 114.5(2) ?
C2 C3 C4 . . 112.46(17) ?
C2 C3 C12 . . 110.00(16) ?
C4 C3 C12 . . 111.46(17) ?
C2 C3 H9 . . 107.6 ?
C4 C3 H9 . . 107.6 ?
C12 C3 H9 . . 107.6 ?
C5 C4 C3 . . 118.21(17) ?
C5 C4 H14 . . 107.8 ?
C3 C4 H14 . . 107.8 ?
C5 C4 H15 . . 107.8 ?
C3 C4 H15 . . 107.8 ?
H14 C4 H15 . . 107.1 ?
C6 C5 C4 . . 123.52(18) ?
C6 C5 C9 . . 112.10(18) ?
C4 C5 C9 . . 124.38(17) ?
C5 C6 C8 . . 109.47(18) ?
C5 C6 C7 . . 127.88(19) ?
C8 C6 C7 . . 122.58(19) ?
C6 C7 H3B . . 109.5 ?
C6 C7 H4 . . 109.5 ?
H3B C7 H4 . . 109.5 ?
C6 C7 H2B . . 109.5 ?
H3B C7 H2B . . 109.5 ?
H4 C7 H2B . . 109.5 ?
O1 C8 C6 . . 125.3(2) ?
O1 C8 C14 . . 125.94(19) ?
C6 C8 C14 . . 108.74(18) ?
O2 C9 C5 . . 106.94(16) ?
O2 C9 C10 . . 109.75(16) ?
C5 C9 C10 . . 113.48(16) ?
O2 C9 C14 . . 113.72(16) ?
C5 C9 C14 . . 102.95(16) ?
C10 C9 C14 . . 109.91(16) ?
O3 C10 C11 . . 111.87(17) ?
O3 C10 C9 . . 106.90(16) ?
C11 C10 C9 . . 115.94(17) ?
O3 C10 H5 . . 107.2 ?
C11 C10 H5 . . 107.2 ?
C9 C10 H5 . . 107.2 ?
C10 C11 C12 . . 117.47(17) ?
C10 C11 H7 . . 107.9 ?
C12 C11 H7 . . 107.9 ?
C10 C11 H6 . . 107.9 ?
C12 C11 H6 . . 107.9 ?
H7 C11 H6 . . 107.2 ?
C11 C12 C3 . . 114.41(17) ?
C11 C12 H16 . . 108.7 ?
C3 C12 H16 . . 108.7 ?
C11 C12 H8 . . 108.7 ?
C3 C12 H8 . . 108.7 ?
H16 C12 H8 . . 107.6 ?
C2 C13 H13 . . 120.0 ?
C2 C13 H12 . . 120.0 ?
H13 C13 H12 . . 120.0 ?
C8 C14 C9 . . 104.38(16) ?
C8 C14 H18 . . 110.9 ?
C9 C14 H18 . . 110.9 ?
C8 C14 H17 . . 110.9 ?
C9 C14 H17 . . 110.9 ?
H18 C14 H17 . . 108.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C2 C3 C4 . . . . -24.2(3) ?
C1 C2 C3 C4 . . . . 156.98(19) ?
C13 C2 C3 C12 . . . . 100.7(2) ?
C1 C2 C3 C12 . . . . -78.2(2) ?
C2 C3 C4 C5 . . . . 178.72(18) ?
C12 C3 C4 C5 . . . . 54.7(2) ?
C3 C4 C5 C6 . . . . -164.48(18) ?
C3 C4 C5 C9 . . . . 15.2(3) ?
C4 C5 C6 C8 . . . . 179.63(18) ?
C9 C5 C6 C8 . . . . -0.1(2) ?
C4 C5 C6 C7 . . . . 2.8(3) ?
C9 C5 C6 C7 . . . . -176.95(19) ?
C5 C6 C8 O1 . . . . -169.42(19) ?
C7 C6 C8 O1 . . . . 7.6(3) ?
C5 C6 C8 C14 . . . . 9.9(2) ?
C7 C6 C8 C14 . . . . -173.02(18) ?
C6 C5 C9 O2 . . . . -129.32(17) ?
C4 C5 C9 O2 . . . . 51.0(2) ?
C6 C5 C9 C10 . . . . 109.5(2) ?
C4 C5 C9 C10 . . . . -70.2(2) ?
C6 C5 C9 C14 . . . . -9.2(2) ?
C4 C5 C9 C14 . . . . 171.06(18) ?
O2 C9 C10 O3 . . . . -175.70(14) ?
C5 C9 C10 O3 . . . . -56.1(2) ?
C14 C9 C10 O3 . . . . 58.5(2) ?
O2 C9 C10 C11 . . . . -50.2(2) ?
C5 C9 C10 C11 . . . . 69.4(2) ?
C14 C9 C10 C11 . . . . -175.97(17) ?
O3 C10 C11 C12 . . . . 65.3(2) ?
C9 C10 C11 C12 . . . . -57.7(2) ?
C10 C11 C12 C3 . . . . 69.9(2) ?
C2 C3 C12 C11 . . . . 148.82(18) ?
C4 C3 C12 C11 . . . . -85.7(2) ?
O1 C8 C14 C9 . . . . 164.19(19) ?
C6 C8 C14 C9 . . . . -15.1(2) ?
O2 C9 C14 C8 . . . . 129.53(16) ?
C5 C9 C14 C8 . . . . 14.21(19) ?
C10 C9 C14 C8 . . . . -106.99(18) ?

####################################################################### 
# 
# 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_99b
_database_code_depnum_ccdc_archive 'CCDC 2195147'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_absolute_configuration ad
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1880(3)
_cell_length_b                   23.4706(8)
_cell_length_c                   13.8857(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2668.51(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4116
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.8370
_cell_measurement_theta_min      4.9190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.193
_diffrn_reflns_theta_min         3.767
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    1.50    --  -40.73 -57.00  30.00  100
  2  ω   -113.00 -63.00   1.00    1.50    --  -40.73-142.00-150.00   50
  3  ω      1.00  82.00   1.00    1.50    --   40.73 -99.00-120.00   81
  4  ω      1.00  82.00   1.00    1.50    --   40.73 -99.00  30.00   81
  5  ω     24.00 109.00   1.00    2.00    --  106.95 -94.00 -30.00   85
  6  ω     35.00 136.00   1.00    2.00    --  106.95 -61.00  90.00  101
  7  ω     94.00 178.00   1.00    2.00    --  106.95 125.00   0.00   84
  8  ω     19.00 178.00   1.00    2.00    --  106.95   0.00-150.00  159
  9  ω   -115.00 -16.00   1.00    2.50    --  -40.73 -38.00 -90.00   99
 10  ω    -56.00 -30.00   1.00    2.50    --  -40.98 -38.00 -60.00   26
 11  ω    134.00 177.00   1.00    4.50    --  106.95  45.00 -90.00   43
 12  ω   -117.00 -70.00   1.00    3.00    --  -40.98 -77.00 -90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0682503000
_diffrn_orient_matrix_UB_12      0.0506160000
_diffrn_orient_matrix_UB_13      -0.0581252000
_diffrn_orient_matrix_UB_21      -0.0498565000
_diffrn_orient_matrix_UB_22      -0.0297789000
_diffrn_orient_matrix_UB_23      -0.0944459000
_diffrn_orient_matrix_UB_31      -0.1681007000
_diffrn_orient_matrix_UB_32      0.0292631000
_diffrn_orient_matrix_UB_33      0.0043654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2435
_reflns_number_total             2610
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.032
_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)+(0.0780P)²+0.5982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1332
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.1569(3) 0.36843(8) 0.03488(14) 0.0462(5) Uani 1 1 d . . . . .
O2 O 0.4720(2) 0.22413(9) 0.43545(15) 0.0471(5) Uani 1 1 d . . . . .
H2 H 0.436708 0.194311 0.458113 0.071 Uiso 1 1 calc R U . . .
C1 C 0.2455(3) 0.30754(11) 0.26558(17) 0.0345(5) Uani 1 1 d . . . . .
C2 C 0.1906(3) 0.29849(12) 0.16289(19) 0.0378(6) Uani 1 1 d . . . . .
H2A H 0.076(4) 0.2829(14) 0.158(2) 0.047(8) Uiso 1 1 d . . . . .
H2B H 0.250(5) 0.2691(16) 0.132(2) 0.066(10) Uiso 1 1 d . . . . .
C3 C 0.1870(3) 0.35674(12) 0.11951(18) 0.0381(6) Uani 1 1 d . . . . .
C4 C 0.2242(3) 0.39751(12) 0.19551(18) 0.0388(6) Uani 1 1 d . . . . .
C5 C 0.2556(3) 0.36957(11) 0.27922(17) 0.0361(6) Uani 1 1 d . . . . .
C6 C 0.2885(4) 0.40167(12) 0.37083(18) 0.0428(6) Uani 1 1 d . . . . .
H6A H 0.211902 0.433122 0.374359 0.051 Uiso 1 1 calc R U . . .
H6B H 0.397126 0.417961 0.366392 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2779(3) 0.36856(11) 0.46485(18) 0.0382(6) Uani 1 1 d . . . . .
H7 H 0.168914 0.351416 0.468449 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4035(3) 0.32006(12) 0.4655(2) 0.0448(6) Uani 1 1 d . . . . .
H8A H 0.497544 0.331697 0.427790 0.054 Uiso 1 1 calc R U . . .
H8B H 0.440120 0.314047 0.531113 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3407(3) 0.26454(11) 0.42622(19) 0.0379(6) Uani 1 1 d . . . . .
H9 H 0.251557 0.251847 0.468142 0.046 Uiso 1 1 calc R U . . .
C10 C 0.2787(3) 0.26308(11) 0.32342(17) 0.0360(6) Uani 1 1 d . . . . .
C11 C 0.2499(4) 0.20321(12) 0.2880(2) 0.0457(7) Uani 1 1 d . . . . .
H11A H 0.163268 0.203294 0.241456 0.069 Uiso 1 1 calc R U . . .
H11B H 0.220258 0.179297 0.341314 0.069 Uiso 1 1 calc R U . . .
H11C H 0.347919 0.188912 0.258760 0.069 Uiso 1 1 calc R U . . .
C12 C 0.2228(5) 0.46028(12) 0.1762(2) 0.0539(8) Uani 1 1 d . . . . .
H12A H 0.124214 0.476591 0.201472 0.081 Uiso 1 1 calc R U . . .
H12B H 0.228004 0.466817 0.108051 0.081 Uiso 1 1 calc R U . . .
H12C H 0.315435 0.477662 0.206804 0.081 Uiso 1 1 calc R U . . .
C13 C 0.2965(4) 0.40838(12) 0.5499(2) 0.0469(7) Uani 1 1 d . . . . .
C14 C 0.1567(6) 0.4253(2) 0.5976(4) 0.0921(17) Uani 1 1 d . . . . .
H14A H 0.153(6) 0.451(2) 0.652(4) 0.100(15) Uiso 1 1 d . . . . .
H14B H 0.064(6) 0.401(2) 0.603(3) 0.099(16) Uiso 1 1 d . . . . .
C15 C 0.4498(5) 0.4279(2) 0.5769(4) 0.0935(16) Uani 1 1 d . . . . .
H15A H 0.527273 0.397360 0.572468 0.140 Uiso 1 1 calc R U . . .
H15B H 0.445644 0.441609 0.642003 0.140 Uiso 1 1 calc R U . . .
H15C H 0.482359 0.458362 0.534878 0.140 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 C3 1.232(3) . ?
O2 H2 0.8200 . ?
O2 C9 1.439(3) . ?
C1 C2 1.510(3) . ?
C1 C5 1.470(4) . ?
C1 C10 1.345(4) . ?
C2 H2A 1.01(3) . ?
C2 H2B 0.94(4) . ?
C2 C3 1.494(4) . ?
C3 C4 1.457(4) . ?
C4 C5 1.359(3) . ?
C4 C12 1.497(4) . ?
C5 C6 1.503(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.522(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(4) . ?
C7 C13 1.514(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.503(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.515(3) . ?
C10 C11 1.507(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.381(5) . ?
C13 C15 1.387(5) . ?
C14 H14A 0.96(5) . ?
C14 H14B 0.95(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
C5 C1 C2 106.1(2) . . ?
C10 C1 C2 121.0(2) . . ?
C10 C1 C5 132.9(2) . . ?
C1 C2 H2A 113.4(19) . . ?
C1 C2 H2B 112(2) . . ?
H2A C2 H2B 100(3) . . ?
C3 C2 C1 104.9(2) . . ?
C3 C2 H2A 106.5(18) . . ?
C3 C2 H2B 120(2) . . ?
O1 C3 C2 126.3(3) . . ?
O1 C3 C4 125.9(3) . . ?
C4 C3 C2 107.7(2) . . ?
C3 C4 C12 121.0(2) . . ?
C5 C4 C3 110.0(2) . . ?
C5 C4 C12 129.0(3) . . ?
C1 C5 C6 128.0(2) . . ?
C4 C5 C1 110.9(2) . . ?
C4 C5 C6 121.1(2) . . ?
C5 C6 H6A 108.0 . . ?
C5 C6 H6B 108.0 . . ?
C5 C6 C7 117.4(2) . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C6 C7 H7 107.8 . . ?
C6 C7 C8 110.2(2) . . ?
C8 C7 H7 107.8 . . ?
C13 C7 C6 110.4(2) . . ?
C13 C7 H7 107.8 . . ?
C13 C7 C8 112.7(2) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.3(2) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
O2 C9 C8 106.5(2) . . ?
O2 C9 H9 107.6 . . ?
O2 C9 C10 108.6(2) . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C10 118.4(2) . . ?
C10 C9 H9 107.6 . . ?
C1 C10 C9 127.8(2) . . ?
C1 C10 C11 119.8(2) . . ?
C11 C10 C9 112.4(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C7 117.9(3) . . ?
C14 C13 C15 121.7(3) . . ?
C15 C13 C7 120.4(3) . . ?
C13 C14 H14A 126(3) . . ?
C13 C14 H14B 122(3) . . ?
H14A C14 H14B 106(4) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C3 C4 C5 -178.2(3) . . . . ?
O1 C3 C4 C12 2.3(4) . . . . ?
O2 C9 C10 C1 -134.0(3) . . . . ?
O2 C9 C10 C11 47.7(3) . . . . ?
C1 C2 C3 O1 175.9(3) . . . . ?
C1 C2 C3 C4 -4.6(3) . . . . ?
C1 C5 C6 C7 -13.2(4) . . . . ?
C2 C1 C5 C4 -4.2(3) . . . . ?
C2 C1 C5 C6 173.5(2) . . . . ?
C2 C1 C10 C9 177.5(2) . . . . ?
C2 C1 C10 C11 -4.2(3) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C2 C3 C4 C12 -177.3(3) . . . . ?
C3 C4 C5 C1 1.3(3) . . . . ?
C3 C4 C5 C6 -176.6(2) . . . . ?
C4 C5 C6 C7 164.2(2) . . . . ?
C5 C1 C2 C3 5.2(2) . . . . ?
C5 C1 C10 C9 -0.2(4) . . . . ?
C5 C1 C10 C11 178.0(3) . . . . ?
C5 C6 C7 C8 60.9(3) . . . . ?
C5 C6 C7 C13 -174.0(3) . . . . ?
C6 C7 C8 C9 -90.6(3) . . . . ?
C6 C7 C13 C14 100.4(4) . . . . ?
C6 C7 C13 C15 -78.2(4) . . . . ?
C7 C8 C9 O2 -178.1(2) . . . . ?
C7 C8 C9 C10 59.3(3) . . . . ?
C8 C7 C13 C14 -135.9(4) . . . . ?
C8 C7 C13 C15 45.5(5) . . . . ?
C8 C9 C10 C1 -12.5(4) . . . . ?
C8 C9 C10 C11 169.2(2) . . . . ?
C10 C1 C2 C3 -173.1(2) . . . . ?
C10 C1 C5 C4 173.8(3) . . . . ?
C10 C1 C5 C6 -8.5(4) . . . . ?
C12 C4 C5 C1 -179.3(3) . . . . ?
C12 C4 C5 C6 2.8(5) . . . . ?
C13 C7 C8 C9 145.6(2) . . . . ?

_olex2_date_sample_data_collection 2021-01-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.964
_oxdiff_exptl_absorpt_empirical_full_min 0.388
####################################################################### 
# 
# 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_RDP111_20211202
_database_code_depnum_ccdc_archive 'CCDC 2195143'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         234.32
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.1320(2)
_cell_length_b                   11.3145(2)
_cell_length_c                   14.8559(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.88(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6641
_cell_measurement_theta_min      4.9132
_cell_measurement_theta_max      68.3247
_cell_measurement_temperature    193.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      193.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            8183
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_theta_min         4.91
_diffrn_reflns_theta_max         68.32
_diffrn_reflns_theta_full        68.32
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2492
_reflns_number_gt                2422
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0873
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         2492
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.1204P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 994 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.13928(18) 0.65675(12) 0.28702(10) 0.0455(4) Uani d . . . 1 . .
O O3 0.24448(17) 0.36752(12) 0.12722(8) 0.0373(3) Uani d . . . 1 . .
H H22 0.211(4) 0.304(3) 0.1470(19) 0.056(8) Uiso d . . . 1 . .
C C1 -0.0140(2) 0.59697(15) 0.29503(11) 0.0338(4) Uani d . . . 1 . .
C C2 0.1205(2) 0.61721(15) 0.35828(11) 0.0332(4) Uani d . . . 1 . .
C C3 0.2331(2) 0.53069(14) 0.34974(11) 0.0297(4) Uani d . . . 1 . .
C C4 0.3826(2) 0.52109(17) 0.40835(12) 0.0357(4) Uani d . . . 1 . .
H H19 0.348004 0.531041 0.47179 0.043 Uiso calc U . R 1 . .
H H5 0.457284 0.587437 0.393595 0.043 Uiso calc U . R 1 . .
C C5 0.4804(2) 0.40504(15) 0.40074(11) 0.0336(4) Uani d . . . 1 . .
H H6 0.400426 0.338054 0.404193 0.04 Uiso calc U . R 1 . .
C C6 0.5969(3) 0.39475(19) 0.48053(14) 0.0450(5) Uani d . . . 1 . .
C C7 0.7349(3) 0.4796(3) 0.4859(2) 0.0663(7) Uani d . . . 1 . .
H H1 0.783736 0.476504 0.54616 0.099 Uiso calc U . R 1 . .
H H7 0.694094 0.559657 0.474148 0.099 Uiso calc U . R 1 . .
H H8 0.818274 0.45896 0.440953 0.099 Uiso calc U . R 1 . .
C C8 0.1232(3) 0.71950(18) 0.42228(14) 0.0463(5) Uani d . . . 1 . .
H H3 0.235206 0.730692 0.445106 0.069 Uiso calc U . R 1 . .
H H4 0.04878 0.70351 0.472712 0.069 Uiso calc U . R 1 . .
H H2 0.087461 0.791219 0.390896 0.069 Uiso calc U . R 1 . .
C C9 0.5720(2) 0.39549(17) 0.31060(13) 0.0366(4) Uani d . . . 1 . .
H H17 0.617913 0.474044 0.295398 0.044 Uiso calc U . R 1 . .
H H18 0.665582 0.340382 0.318124 0.044 Uiso calc U . R 1 . .
C C10 0.4669(2) 0.35302(16) 0.23179(12) 0.0357(4) Uani d . . . 1 . .
H H16 0.424121 0.273734 0.247508 0.043 Uiso calc U . R 1 . .
H H15 0.540615 0.342783 0.179345 0.043 Uiso calc U . R 1 . .
C C15 0.5718(4) 0.3113(3) 0.54283(17) 0.0648(7) Uani d . . . 1 . .
H H21 0.652(4) 0.304(3) 0.595(2) 0.076(9) Uiso d . . . 1 . .
C C11 0.3204(2) 0.42835(14) 0.20103(11) 0.0297(4) Uani d . . . 1 . .
C C12 0.3736(3) 0.54754(17) 0.16298(14) 0.0426(4) Uani d . . . 1 . .
H H10 0.443316 0.534961 0.110029 0.064 Uiso calc U . R 1 . .
H H11 0.435578 0.591105 0.208812 0.064 Uiso calc U . R 1 . .
H H9 0.276171 0.593143 0.145662 0.064 Uiso calc U . R 1 . .
C C13 0.18966(19) 0.44273(13) 0.27641(11) 0.0281(3) Uani d . . . 1 . .
H H12 0.171934 0.363819 0.305123 0.034 Uiso calc U . R 1 . .
C C14 0.0235(2) 0.48746(16) 0.24119(12) 0.0351(4) Uani d . . . 1 . .
H H14 0.030521 0.5063 0.176227 0.042 Uiso calc U . R 1 . .
H H13 -0.063068 0.427063 0.250193 0.042 Uiso calc U . R 1 . .
H H20 0.473(5) 0.253(4) 0.540(2) 0.098(12) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.229(2) ?
O3 C11 . 1.434(2) ?
O3 H22 . 0.82(3) ?
C1 C2 . 1.460(2) ?
C1 C14 . 1.506(2) ?
C2 C3 . 1.347(2) ?
C2 C8 . 1.498(2) ?
C3 C4 . 1.500(2) ?
C3 C13 . 1.517(2) ?
C4 C5 . 1.539(2) ?
C4 H19 . 0.99 ?
C4 H5 . 0.99 ?
C5 C6 . 1.522(2) ?
C5 C9 . 1.536(3) ?
C5 H6 . 1.0 ?
C6 C15 . 1.338(4) ?
C6 C7 . 1.479(4) ?
C7 H1 . 0.98 ?
C7 H7 . 0.98 ?
C7 H8 . 0.98 ?
C8 H3 . 0.98 ?
C8 H4 . 0.98 ?
C8 H2 . 0.98 ?
C9 C10 . 1.527(2) ?
C9 H17 . 0.99 ?
C9 H18 . 0.99 ?
C10 C11 . 1.534(2) ?
C10 H16 . 0.99 ?
C10 H15 . 0.99 ?
C15 H21 . 1.01(4) ?
C15 H20 . 1.04(4) ?
C11 C12 . 1.525(2) ?
C11 C13 . 1.552(2) ?
C12 H10 . 0.98 ?
C12 H11 . 0.98 ?
C12 H9 . 0.98 ?
C13 C14 . 1.535(2) ?
C13 H12 . 1.0 ?
C14 H14 . 0.99 ?
C14 H13 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O3 H22 . . 107.(2) ?
O1 C1 C2 . . 126.66(16) ?
O1 C1 C14 . . 124.71(17) ?
C2 C1 C14 . . 108.62(14) ?
C3 C2 C1 . . 109.56(15) ?
C3 C2 C8 . . 127.69(17) ?
C1 C2 C8 . . 122.75(16) ?
C2 C3 C4 . . 123.33(15) ?
C2 C3 C13 . . 112.72(15) ?
C4 C3 C13 . . 123.93(14) ?
C3 C4 C5 . . 115.98(14) ?
C3 C4 H19 . . 108.3 ?
C5 C4 H19 . . 108.3 ?
C3 C4 H5 . . 108.3 ?
C5 C4 H5 . . 108.3 ?
H19 C4 H5 . . 107.4 ?
C6 C5 C9 . . 111.83(15) ?
C6 C5 C4 . . 109.24(14) ?
C9 C5 C4 . . 111.99(15) ?
C6 C5 H6 . . 107.9 ?
C9 C5 H6 . . 107.9 ?
C4 C5 H6 . . 107.9 ?
C15 C6 C7 . . 122.4(2) ?
C15 C6 C5 . . 119.9(2) ?
C7 C6 C5 . . 117.7(2) ?
C6 C7 H1 . . 109.5 ?
C6 C7 H7 . . 109.5 ?
H1 C7 H7 . . 109.5 ?
C6 C7 H8 . . 109.5 ?
H1 C7 H8 . . 109.5 ?
H7 C7 H8 . . 109.5 ?
C2 C8 H3 . . 109.5 ?
C2 C8 H4 . . 109.5 ?
H3 C8 H4 . . 109.5 ?
C2 C8 H2 . . 109.5 ?
H3 C8 H2 . . 109.5 ?
H4 C8 H2 . . 109.5 ?
C10 C9 C5 . . 114.75(14) ?
C10 C9 H17 . . 108.6 ?
C5 C9 H17 . . 108.6 ?
C10 C9 H18 . . 108.6 ?
C5 C9 H18 . . 108.6 ?
H17 C9 H18 . . 107.6 ?
C9 C10 C11 . . 119.22(14) ?
C9 C10 H16 . . 107.5 ?
C11 C10 H16 . . 107.5 ?
C9 C10 H15 . . 107.5 ?
C11 C10 H15 . . 107.5 ?
H16 C10 H15 . . 107.0 ?
C6 C15 H21 . . 119.3(19) ?
C6 C15 H20 . . 123.(2) ?
H21 C15 H20 . . 118.(3) ?
O3 C11 C12 . . 105.26(14) ?
O3 C11 C10 . . 107.17(13) ?
C12 C11 C10 . . 112.40(15) ?
O3 C11 C13 . . 107.89(13) ?
C12 C11 C13 . . 111.65(14) ?
C10 C11 C13 . . 112.02(13) ?
C11 C12 H10 . . 109.5 ?
C11 C12 H11 . . 109.5 ?
H10 C12 H11 . . 109.5 ?
C11 C12 H9 . . 109.5 ?
H10 C12 H9 . . 109.5 ?
H11 C12 H9 . . 109.5 ?
C3 C13 C14 . . 103.50(13) ?
C3 C13 C11 . . 115.30(13) ?
C14 C13 C11 . . 113.05(13) ?
C3 C13 H12 . . 108.2 ?
C14 C13 H12 . . 108.2 ?
C11 C13 H12 . . 108.2 ?
C1 C14 C13 . . 105.57(14) ?
C1 C14 H14 . . 110.6 ?
C13 C14 H14 . . 110.6 ?
C1 C14 H13 . . 110.6 ?
C13 C14 H13 . . 110.6 ?
H14 C14 H13 . . 108.8 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 177.51(18) ?
C14 C1 C2 C3 . . . . -1.2(2) ?
O1 C1 C2 C8 . . . . -1.5(3) ?
C14 C1 C2 C8 . . . . 179.76(18) ?
C1 C2 C3 C4 . . . . -176.55(16) ?
C8 C2 C3 C4 . . . . 2.4(3) ?
C1 C2 C3 C13 . . . . 1.9(2) ?
C8 C2 C3 C13 . . . . -179.16(18) ?
C2 C3 C4 C5 . . . . 169.19(17) ?
C13 C3 C4 C5 . . . . -9.1(2) ?
C3 C4 C5 C6 . . . . -164.58(17) ?
C3 C4 C5 C9 . . . . 71.0(2) ?
C9 C5 C6 C15 . . . . -123.3(2) ?
C4 C5 C6 C15 . . . . 112.1(2) ?
C9 C5 C6 C7 . . . . 57.0(2) ?
C4 C5 C6 C7 . . . . -67.6(2) ?
C6 C5 C9 C10 . . . . 155.28(16) ?
C4 C5 C9 C10 . . . . -81.72(19) ?
C5 C9 C10 C11 . . . . 62.9(2) ?
C9 C10 C11 O3 . . . . -179.69(15) ?
C9 C10 C11 C12 . . . . 65.1(2) ?
C9 C10 C11 C13 . . . . -61.5(2) ?
C2 C3 C13 C14 . . . . -1.74(18) ?
C4 C3 C13 C14 . . . . 176.69(16) ?
C2 C3 C13 C11 . . . . 122.23(16) ?
C4 C3 C13 C11 . . . . -59.3(2) ?
O3 C11 C13 C3 . . . . -165.41(13) ?
C12 C11 C13 C3 . . . . -50.22(19) ?
C10 C11 C13 C3 . . . . 76.86(17) ?
O3 C11 C13 C14 . . . . -46.62(18) ?
C12 C11 C13 C14 . . . . 68.58(19) ?
C10 C11 C13 C14 . . . . -164.34(13) ?
O1 C1 C14 C13 . . . . -178.66(17) ?
C2 C1 C14 C13 . . . . 0.13(19) ?
C3 C13 C14 C1 . . . . 0.88(17) ?
C11 C13 C14 C1 . . . . -124.56(14) ?

####################################################################### 
# 
# 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_rdp-31
_database_code_depnum_ccdc_archive 'CCDC 2195145'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_audit_creation_date             2020-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   8.7052(8)
_cell_length_b                   10.0397(7)
_cell_length_c                   16.0048(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.951(8)
_cell_angle_gamma                90
_cell_volume                     1351.41(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2054
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5880
_cell_measurement_theta_min      5.1840
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3623
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.746
_diffrn_reflns_theta_min         5.253
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  21.00   0.50    0.50    --  -40.98  38.00  60.00  160
  2  ω      7.00  82.00   0.50    0.50    --   40.98 -99.00 150.00  150
  3  ω     26.00 104.00   0.50    1.00    --  106.95 -95.00  60.00  156
  4  ω     80.00 128.00   0.50    1.00    --  106.95 -30.00   0.00   96
  5  ω    121.00 178.00   0.50    1.00    --  106.95  30.00 -60.00  114
  6  ω    124.00 163.00   0.50    1.00    --  106.95 125.00 -90.00   78
  7  ω     98.00 176.00   0.50    1.00    --  106.95  45.00  60.00  156
  8  ω    128.00 170.00   0.50    1.00    --  106.95  45.00 150.00   84
  9  ω     39.00 133.00   0.50    1.00    --  106.95 -45.00-120.00  188
 10  ω    -94.00  -2.00   0.50    0.50    --  -40.98 125.00 -90.00  184
 11  ω    -95.00 -39.00   0.50    0.50    --  -41.23 -38.00 120.00  112
 12  ω     18.00 111.00   0.50    0.50    --   41.23  57.00-120.00  186
 13  ω      5.00  53.00   0.50    0.50    --   41.23 -38.00  30.00   96
 14  ω     59.00 102.00   0.50    1.00    --  106.95 -95.00 -90.00   86
 15  ω     45.00  71.00   0.50    1.00    --  106.95 -45.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640761000
_diffrn_orient_matrix_UB_12      -0.0937323000
_diffrn_orient_matrix_UB_13      0.0773300000
_diffrn_orient_matrix_UB_21      0.1624706000
_diffrn_orient_matrix_UB_22      0.0707592000
_diffrn_orient_matrix_UB_23      0.0188458000
_diffrn_orient_matrix_UB_31      -0.0553045000
_diffrn_orient_matrix_UB_32      0.0987165000
_diffrn_orient_matrix_UB_33      0.0599184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.526
_reflns_Friedel_fraction_full    0.613
_reflns_Friedel_fraction_max     0.567
_reflns_number_gt                2040
_reflns_number_total             2115
_reflns_odcompleteness_completeness 97.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.065
_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)+(0.0867P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1333
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.7601(2) 0.4418(2) 0.97313(12) 0.0364(5) Uani 1 1 d . . . . .
O2 O 1.0046(3) 0.5435(2) 0.89390(13) 0.0390(5) Uani 1 1 d . . . . .
H2 H 1.061777 0.506301 0.936265 0.059 Uiso 1 1 calc R U . . .
C1 C 0.5941(3) 0.4702(3) 0.82932(16) 0.0245(5) Uani 1 1 d . . . . .
C2 C 0.7444(3) 0.4538(3) 0.89535(16) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.8821(3) 0.4567(3) 0.85245(17) 0.0278(6) Uani 1 1 d . . . . .
H3 H 0.925073 0.366564 0.851984 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8041(3) 0.5007(3) 0.75900(18) 0.0293(6) Uani 1 1 d . . . . .
H4 H 0.829789 0.436560 0.718480 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6270(3) 0.4951(3) 0.75318(18) 0.0278(6) Uani 1 1 d . . . . .
C6 C 0.5127(4) 0.5261(4) 0.66742(19) 0.0378(7) Uani 1 1 d . . . . .
H6A H 0.569422 0.518312 0.622855 0.045 Uiso 1 1 calc R U . . .
H6B H 0.479627 0.618225 0.668381 0.045 Uiso 1 1 calc R U . . .
C7 C 0.3625(3) 0.4392(4) 0.64111(17) 0.0364(7) Uani 1 1 d . . . . .
H7 H 0.396263 0.345727 0.646669 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2476(3) 0.4607(3) 0.69896(17) 0.0317(6) Uani 1 1 d . . . . .
H8A H 0.232031 0.555660 0.704291 0.038 Uiso 1 1 calc R U . . .
H8B H 0.145416 0.422214 0.670265 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3023(3) 0.4013(3) 0.78944(17) 0.0273(6) Uani 1 1 d . . . . .
H9A H 0.334199 0.309853 0.783854 0.033 Uiso 1 1 calc R U . . .
H9B H 0.211588 0.398900 0.814125 0.033 Uiso 1 1 calc R U . . .
C10 C 0.4388(3) 0.4719(3) 0.85380(16) 0.0266(6) Uani 1 1 d . . . . .
H10 H 0.455883 0.424312 0.908890 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2778(4) 0.4640(6) 0.5470(2) 0.0600(12) Uani 1 1 d . . . . .
C12 C 0.2537(9) 0.3628(8) 0.4905(3) 0.098(3) Uani 1 1 d . . . . .
H12A H 0.192(8) 0.387(7) 0.431(4) 0.11(2) Uiso 1 1 d . . . . .
H12B H 0.296(10) 0.276(9) 0.507(5) 0.13(3) Uiso 1 1 d . . . . .
C13 C 0.2234(7) 0.6002(7) 0.5212(3) 0.093(2) Uani 1 1 d . . . . .
H13A H 0.157423 0.631187 0.556850 0.140 Uiso 1 1 calc R U . . .
H13B H 0.163529 0.600395 0.461734 0.140 Uiso 1 1 calc R U . . .
H13C H 0.313797 0.657889 0.528186 0.140 Uiso 1 1 calc R U . . .
C14 C 0.3979(4) 0.6167(3) 0.8708(2) 0.0345(7) Uani 1 1 d . . . . .
H14A H 0.481109 0.653350 0.916483 0.052 Uiso 1 1 calc R U . . .
H14B H 0.299452 0.618877 0.887255 0.052 Uiso 1 1 calc R U . . .
H14C H 0.387683 0.668404 0.819142 0.052 Uiso 1 1 calc R U . . .
C15 C 0.8539(4) 0.6400(4) 0.7386(2) 0.0381(7) Uani 1 1 d . . . . .
H15A H 0.835071 0.701776 0.780676 0.057 Uiso 1 1 calc R U . . .
H15B H 0.793054 0.665994 0.682027 0.057 Uiso 1 1 calc R U . . .
H15C H 0.964948 0.639940 0.740320 0.057 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 C2 1.223(3) . ?
O2 H2 0.8200 . ?
O2 C3 1.404(3) . ?
C1 C2 1.463(4) . ?
C1 C5 1.345(4) . ?
C1 C10 1.502(3) . ?
C2 C3 1.528(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.539(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.522(4) . ?
C4 C15 1.524(4) . ?
C5 C6 1.505(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.537(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.544(4) . ?
C7 C11 1.517(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.524(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.531(4) . ?
C10 H10 0.9800 . ?
C10 C14 1.537(4) . ?
C11 C12 1.340(8) . ?
C11 C13 1.471(8) . ?
C12 H12A 0.99(7) . ?
C12 H12B 0.96(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 109.5 . . ?
C2 C1 C10 120.7(2) . . ?
C5 C1 C2 108.4(2) . . ?
C5 C1 C10 130.6(3) . . ?
O1 C2 C1 126.2(2) . . ?
O1 C2 C3 124.4(2) . . ?
C1 C2 C3 109.4(2) . . ?
O2 C3 C2 112.8(2) . . ?
O2 C3 H3 109.4 . . ?
O2 C3 C4 111.8(2) . . ?
C2 C3 H3 109.4 . . ?
C2 C3 C4 104.0(2) . . ?
C4 C3 H3 109.4 . . ?
C3 C4 H4 109.6 . . ?
C5 C4 C3 103.6(2) . . ?
C5 C4 H4 109.6 . . ?
C5 C4 C15 111.1(2) . . ?
C15 C4 C3 113.1(3) . . ?
C15 C4 H4 109.6 . . ?
C1 C5 C4 113.6(3) . . ?
C1 C5 C6 128.3(3) . . ?
C6 C5 C4 118.0(2) . . ?
C5 C6 H6A 108.1 . . ?
C5 C6 H6B 108.1 . . ?
C5 C6 C7 116.6(3) . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 H6A 108.1 . . ?
C7 C6 H6B 108.1 . . ?
C6 C7 H7 107.8 . . ?
C6 C7 C8 113.1(3) . . ?
C8 C7 H7 107.8 . . ?
C11 C7 C6 109.9(3) . . ?
C11 C7 H7 107.8 . . ?
C11 C7 C8 110.4(3) . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 115.0(2) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C8 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
C8 C9 C10 117.1(2) . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C1 C10 C9 114.4(2) . . ?
C1 C10 H10 106.9 . . ?
C1 C10 C14 108.8(2) . . ?
C9 C10 H10 106.9 . . ?
C9 C10 C14 112.5(2) . . ?
C14 C10 H10 106.9 . . ?
C12 C11 C7 119.8(5) . . ?
C12 C11 C13 122.1(5) . . ?
C13 C11 C7 118.1(4) . . ?
C11 C12 H12A 114(4) . . ?
C11 C12 H12B 122(5) . . ?
H12A C12 H12B 124(6) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C2 C3 O2 -47.8(4) . . . . ?
O1 C2 C3 C4 -169.2(3) . . . . ?
O2 C3 C4 C5 -131.6(3) . . . . ?
O2 C3 C4 C15 -11.2(3) . . . . ?
C1 C2 C3 O2 131.1(3) . . . . ?
C1 C2 C3 C4 9.7(3) . . . . ?
C1 C5 C6 C7 -44.7(5) . . . . ?
C2 C1 C5 C4 -0.9(3) . . . . ?
C2 C1 C5 C6 -176.5(3) . . . . ?
C2 C1 C10 C9 -141.9(3) . . . . ?
C2 C1 C10 C14 91.3(3) . . . . ?
C2 C3 C4 C5 -9.5(3) . . . . ?
C2 C3 C4 C15 110.9(3) . . . . ?
C3 C4 C5 C1 7.0(3) . . . . ?
C3 C4 C5 C6 -177.0(3) . . . . ?
C4 C5 C6 C7 139.9(3) . . . . ?
C5 C1 C2 O1 173.1(3) . . . . ?
C5 C1 C2 C3 -5.7(3) . . . . ?
C5 C1 C10 C9 45.7(4) . . . . ?
C5 C1 C10 C14 -81.0(4) . . . . ?
C5 C6 C7 C8 67.4(4) . . . . ?
C5 C6 C7 C11 -168.7(3) . . . . ?
C6 C7 C8 C9 -73.3(4) . . . . ?
C6 C7 C11 C12 121.0(5) . . . . ?
C6 C7 C11 C13 -59.5(5) . . . . ?
C7 C8 C9 C10 73.1(3) . . . . ?
C8 C7 C11 C12 -113.5(5) . . . . ?
C8 C7 C11 C13 65.9(5) . . . . ?
C8 C9 C10 C1 -64.4(3) . . . . ?
C8 C9 C10 C14 60.4(3) . . . . ?
C10 C1 C2 O1 -0.8(5) . . . . ?
C10 C1 C2 C3 -179.6(2) . . . . ?
C10 C1 C5 C4 172.2(3) . . . . ?
C10 C1 C5 C6 -3.4(5) . . . . ?
C11 C7 C8 C9 163.1(3) . . . . ?
C15 C4 C5 C1 -114.8(3) . . . . ?
C15 C4 C5 C6 61.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.914
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_RDP3220200728
_database_code_depnum_ccdc_archive 'CCDC 2195146'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         250.36
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.7124(4)
_cell_length_b                   6.5713(3)
_cell_length_c                   12.0658(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.5330(10)
_cell_angle_gamma                90
_cell_volume                     690.76(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4427
_cell_measurement_theta_min      6.2389
_cell_measurement_theta_max      72.3948
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            3297
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_theta_min         6.24
_diffrn_reflns_theta_max         72.38
_diffrn_reflns_theta_full        72.38
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2024
_reflns_number_gt                2021
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0943
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_number_reflns         2024
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.1056P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.136
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 592 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(6)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.63342(18) 0.4847(3) 0.00097(12) 0.0360(4) Uani d . . . 1.0 . .
O O3 0.38682(17) 0.1346(2) 0.21476(11) 0.0304(3) Uani d . . . 1.0 . .
H H21 0.376(6) 0.087(11) 0.148(5) 0.119(19) Uiso d . . . 1.0 . .
O O4 0.65181(16) 0.3140(3) 0.22270(12) 0.0335(4) Uani d . . . 1.0 . .
H H20 0.605(4) 0.193(8) 0.235(3) 0.065(11) Uiso d . . . 1.0 . .
C C1 0.1552(3) 0.5573(5) 0.54389(19) 0.0459(6) Uani d . . . 1.0 . .
H H12 0.161047 0.627362 0.61551 0.069 Uiso calc U . R 1.0 . .
H H11 0.211497 0.42843 0.548568 0.069 Uiso calc U . R 1.0 . .
H H1 0.047519 0.530095 0.524936 0.069 Uiso calc U . R 1.0 . .
C C2 0.2253(2) 0.6897(4) 0.45568(16) 0.0312(5) Uani d . . . 1.0 . .
C C3 0.2176(2) 0.6104(3) 0.33747(15) 0.0276(4) Uani d . . . 1.0 . .
H H10 0.269158 0.711847 0.288512 0.033 Uiso calc U . R 1.0 . .
C C4 0.0487(2) 0.5887(4) 0.29797(18) 0.0355(5) Uani d . . . 1.0 . .
H H7 0.005616 0.462625 0.330044 0.043 Uiso calc U . R 1.0 . .
H H6 -0.010939 0.704682 0.327451 0.043 Uiso calc U . R 1.0 . .
C C5 0.0268(2) 0.5818(4) 0.17195(19) 0.0382(5) Uani d . . . 1.0 . .
H H4 0.069336 0.708787 0.140523 0.046 Uiso calc U . R 1.0 . .
H H5 -0.084705 0.580961 0.155524 0.046 Uiso calc U . R 1.0 . .
C C6 0.1002(2) 0.4005(4) 0.11123(16) 0.0326(5) Uani d . . . 1.0 . .
H H3 0.069494 0.413412 0.031482 0.039 Uiso calc U . R 1.0 . .
C C7 0.0399(2) 0.1945(4) 0.1504(2) 0.0407(5) Uani d . . . 1.0 . .
H H14 0.084515 0.085939 0.105294 0.061 Uiso calc U . R 1.0 . .
H H2 -0.072167 0.191552 0.142772 0.061 Uiso calc U . R 1.0 . .
H H13 0.06866 0.17391 0.228335 0.061 Uiso calc U . R 1.0 . .
C C8 0.5223(2) 0.4709(3) 0.06177(15) 0.0282(4) Uani d . . . 1.0 . .
C C9 0.5314(2) 0.4460(3) 0.18845(15) 0.0264(4) Uani d . . . 1.0 . .
C C10 0.3699(2) 0.3533(3) 0.21502(15) 0.0246(4) Uani d . . . 1.0 . .
C C11 0.2726(2) 0.4164(3) 0.11530(15) 0.0263(4) Uani d . . . 1.0 . .
C C12 0.3064(2) 0.4077(3) 0.32939(14) 0.0264(4) Uani d . . . 1.0 . .
H H8 0.393327 0.412377 0.382776 0.032 Uiso calc U . R 1.0 . .
H H9 0.237408 0.296472 0.353051 0.032 Uiso calc U . R 1.0 . .
C C13 0.3596(2) 0.4784(4) 0.03145(15) 0.0303(4) Uani d . . . 1.0 . .
H H15 0.320997 0.52154 -0.038585 0.036 Uiso calc U . R 1.0 . .
C C14 0.5648(2) 0.6560(4) 0.23635(17) 0.0319(4) Uani d . . . 1.0 . .
H H16 0.552097 0.652667 0.316945 0.048 Uiso calc U . R 1.0 . .
H H18 0.493422 0.755242 0.203963 0.048 Uiso calc U . R 1.0 . .
H H17 0.670411 0.695179 0.218958 0.048 Uiso calc U . R 1.0 . .
C C15 0.2904(3) 0.8662(4) 0.47904(19) 0.0400(10) Uani d . P . 1.025(15) A 1
H H1 0.295(3) 0.910(5) 0.558(2) 0.040(7) Uiso d . . . 1.0 B 1
H H15 0.327(3) 0.953(6) 0.422(3) 0.042(7) Uiso d . . . 1.0 C 1


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.223(2) ?
O3 C10 . 1.445(2) ?
O3 H21 . 0.87(6) ?
O4 C9 . 1.420(2) ?
O4 H20 . 0.90(5) ?
C1 C2 . 1.508(3) ?
C1 H12 . 0.98 ?
C1 H11 . 0.98 ?
C1 H1 . 0.98 ?
C2 C15 . 1.321(3) ?
C2 C3 . 1.519(3) ?
C3 C12 . 1.544(3) ?
C3 C4 . 1.549(2) ?
C3 H10 . 1.0 ?
C4 C5 . 1.531(3) ?
C4 H7 . 0.99 ?
C4 H6 . 0.99 ?
C5 C6 . 1.541(3) ?
C5 H4 . 0.99 ?
C5 H5 . 0.99 ?
C6 C11 . 1.506(2) ?
C6 C7 . 1.529(4) ?
C6 H3 . 1.0 ?
C7 H14 . 0.98 ?
C7 H2 . 0.98 ?
C7 H13 . 0.98 ?
C8 C13 . 1.462(3) ?
C8 C9 . 1.538(2) ?
C9 C14 . 1.523(3) ?
C9 C10 . 1.569(3) ?
C10 C11 . 1.523(2) ?
C10 C12 . 1.534(2) ?
C11 C13 . 1.333(3) ?
C12 H8 . 0.99 ?
C12 H9 . 0.99 ?
C13 H15 . 0.95 ?
C14 H16 . 0.98 ?
C14 H18 . 0.98 ?
C14 H17 . 0.98 ?
C15 H1 . 0.99(3) ?
C15 H15 . 0.95(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O3 H21 . . 111.(5) ?
C9 O4 H20 . . 104.(2) ?
C2 C1 H12 . . 109.5 ?
C2 C1 H11 . . 109.5 ?
H12 C1 H11 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H12 C1 H1 . . 109.5 ?
H11 C1 H1 . . 109.5 ?
C15 C2 C1 . . 122.1(2) ?
C15 C2 C3 . . 121.1(2) ?
C1 C2 C3 . . 116.8(2) ?
C2 C3 C12 . . 109.72(16) ?
C2 C3 C4 . . 110.69(15) ?
C12 C3 C4 . . 112.12(18) ?
C2 C3 H10 . . 108.1 ?
C12 C3 H10 . . 108.1 ?
C4 C3 H10 . . 108.1 ?
C5 C4 C3 . . 114.65(17) ?
C5 C4 H7 . . 108.6 ?
C3 C4 H7 . . 108.6 ?
C5 C4 H6 . . 108.6 ?
C3 C4 H6 . . 108.6 ?
H7 C4 H6 . . 107.6 ?
C4 C5 C6 . . 116.55(19) ?
C4 C5 H4 . . 108.2 ?
C6 C5 H4 . . 108.2 ?
C4 C5 H5 . . 108.2 ?
C6 C5 H5 . . 108.2 ?
H4 C5 H5 . . 107.3 ?
C11 C6 C7 . . 113.40(18) ?
C11 C6 C5 . . 110.41(17) ?
C7 C6 C5 . . 113.10(17) ?
C11 C6 H3 . . 106.5 ?
C7 C6 H3 . . 106.5 ?
C5 C6 H3 . . 106.5 ?
C6 C7 H14 . . 109.5 ?
C6 C7 H2 . . 109.5 ?
H14 C7 H2 . . 109.5 ?
C6 C7 H13 . . 109.5 ?
H14 C7 H13 . . 109.5 ?
H2 C7 H13 . . 109.5 ?
O1 C8 C13 . . 128.20(17) ?
O1 C8 C9 . . 124.76(17) ?
C13 C8 C9 . . 107.03(15) ?
O4 C9 C14 . . 107.75(16) ?
O4 C9 C8 . . 112.65(15) ?
C14 C9 C8 . . 106.76(17) ?
O4 C9 C10 . . 111.40(16) ?
C14 C9 C10 . . 116.28(15) ?
C8 C9 C10 . . 101.92(14) ?
O3 C10 C11 . . 108.99(16) ?
O3 C10 C12 . . 105.75(16) ?
C11 C10 C12 . . 116.39(15) ?
O3 C10 C9 . . 107.11(15) ?
C11 C10 C9 . . 103.07(15) ?
C12 C10 C9 . . 115.15(16) ?
C13 C11 C6 . . 124.77(17) ?
C13 C11 C10 . . 111.51(16) ?
C6 C11 C10 . . 123.66(17) ?
C10 C12 C3 . . 116.30(16) ?
C10 C12 H8 . . 108.2 ?
C3 C12 H8 . . 108.2 ?
C10 C12 H9 . . 108.2 ?
C3 C12 H9 . . 108.2 ?
H8 C12 H9 . . 107.4 ?
C11 C13 C8 . . 110.89(16) ?
C11 C13 H15 . . 124.6 ?
C8 C13 H15 . . 124.6 ?
C9 C14 H16 . . 109.5 ?
C9 C14 H18 . . 109.5 ?
H16 C14 H18 . . 109.5 ?
C9 C14 H17 . . 109.5 ?
H16 C14 H17 . . 109.5 ?
H18 C14 H17 . . 109.5 ?
C2 C15 H1 . . 118.3(19) ?
C2 C15 H15 . . 121.2(19) ?
H1 C15 H15 . . 120.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 C2 C3 C12 . . . . 118.3(2) ?
C1 C2 C3 C12 . . . . -61.7(2) ?
C15 C2 C3 C4 . . . . -117.4(2) ?
C1 C2 C3 C4 . . . . 62.6(3) ?
C2 C3 C4 C5 . . . . 160.0(2) ?
C12 C3 C4 C5 . . . . -77.1(2) ?
C3 C4 C5 C6 . . . . 63.2(3) ?
C4 C5 C6 C11 . . . . -68.7(2) ?
C4 C5 C6 C7 . . . . 59.6(2) ?
O1 C8 C9 O4 . . . . -39.3(3) ?
C13 C8 C9 O4 . . . . 141.76(18) ?
O1 C8 C9 C14 . . . . 78.7(2) ?
C13 C8 C9 C14 . . . . -100.16(19) ?
O1 C8 C9 C10 . . . . -158.8(2) ?
C13 C8 C9 C10 . . . . 22.3(2) ?
O4 C9 C10 O3 . . . . -27.5(2) ?
C14 C9 C10 O3 . . . . -151.45(16) ?
C8 C9 C10 O3 . . . . 92.89(17) ?
O4 C9 C10 C11 . . . . -142.37(16) ?
C14 C9 C10 C11 . . . . 93.65(19) ?
C8 C9 C10 C11 . . . . -22.01(18) ?
O4 C9 C10 C12 . . . . 89.8(2) ?
C14 C9 C10 C12 . . . . -34.2(2) ?
C8 C9 C10 C12 . . . . -149.83(16) ?
C7 C6 C11 C13 . . . . 129.3(2) ?
C5 C6 C11 C13 . . . . -102.5(2) ?
C7 C6 C11 C10 . . . . -47.6(3) ?
C5 C6 C11 C10 . . . . 80.6(2) ?
O3 C10 C11 C13 . . . . -98.1(2) ?
C12 C10 C11 C13 . . . . 142.47(19) ?
C9 C10 C11 C13 . . . . 15.4(2) ?
O3 C10 C11 C6 . . . . 79.2(2) ?
C12 C10 C11 C6 . . . . -40.3(3) ?
C9 C10 C11 C6 . . . . -167.31(18) ?
O3 C10 C12 C3 . . . . -156.17(16) ?
C11 C10 C12 C3 . . . . -35.0(2) ?
C9 C10 C12 C3 . . . . 85.8(2) ?
C2 C3 C12 C10 . . . . -154.55(16) ?
C4 C3 C12 C10 . . . . 82.0(2) ?
C6 C11 C13 C8 . . . . -178.45(19) ?
C10 C11 C13 C8 . . . . -1.2(3) ?
O1 C8 C13 C11 . . . . 167.1(2) ?
C9 C8 C13 C11 . . . . -14.1(2) ?

####################################################################### 
# 
# 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_TR35_20211022
_database_code_depnum_ccdc_archive 'CCDC 2195142'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         234.32
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.9215(2)
_cell_length_b                   12.7299(3)
_cell_length_c                   15.0170(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1323.15(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3967
_cell_measurement_theta_min      4.5536
_cell_measurement_theta_max      68.0761
_cell_measurement_temperature    155.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      155.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            8405
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2389
_reflns_number_gt                2172
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0823
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.1240P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.127
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(15)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4167(3) 0.25497(14) 0.57906(13) 0.0424(4) Uani d . . . 1 . .
O O3 0.6710(2) 0.38487(12) 0.31505(10) 0.0290(3) Uani d . . . 1 . .
H H22 0.754(5) 0.345(3) 0.341(2) 0.049(9) Uiso d . . . 1 . .
C C1 0.6793(4) 0.81876(18) 0.41490(18) 0.0417(6) Uani d . . . 1 . .
H H1 0.759407 0.882235 0.415275 0.063 Uiso calc U . R 1 . .
H H12 0.656264 0.795733 0.476264 0.063 Uiso calc U . R 1 . .
H H13 0.555494 0.834061 0.386021 0.063 Uiso calc U . R 1 . .
C C2 0.7818(3) 0.73312(16) 0.36445(13) 0.0273(4) Uani d . . . 1 . .
C C3 0.6803(3) 0.62767(16) 0.35646(13) 0.0239(4) Uani d . . . 1 . .
H H9 0.759262 0.582259 0.316106 0.029 Uiso calc U . R 1 . .
C C4 0.4792(3) 0.64079(17) 0.31400(15) 0.0302(4) Uani d . . . 1 . .
H H7 0.385782 0.659986 0.3612 0.036 Uiso calc U . R 1 . .
H H8 0.484167 0.699696 0.271013 0.036 Uiso calc U . R 1 . .
C C5 0.4052(3) 0.54305(19) 0.26592(15) 0.0314(5) Uani d . . . 1 . .
H H6 0.506865 0.519384 0.224122 0.038 Uiso calc U . R 1 . .
H H14 0.291775 0.563683 0.229746 0.038 Uiso calc U . R 1 . .
C C6 0.3465(3) 0.44861(17) 0.32404(15) 0.0285(4) Uani d . . . 1 . .
H H15 0.300585 0.392837 0.282204 0.034 Uiso calc U . R 1 . .
C C15 0.9516(3) 0.74944(19) 0.32607(15) 0.0340(5) Uani d . . . 1 . .
H H21 1.015(4) 0.813(3) 0.3316(19) 0.041(7) Uiso d . . . 1 . .
H H20 1.017(4) 0.695(2) 0.2909(18) 0.039(7) Uiso d . . . 1 . .
C C7 0.1750(3) 0.47534(19) 0.38420(17) 0.0338(5) Uani d . . . 1 . .
H H2 0.211222 0.532238 0.424862 0.051 Uiso calc U . R 1 . .
H H17 0.138383 0.413142 0.418759 0.051 Uiso calc U . R 1 . .
H H16 0.065383 0.497773 0.3475 0.051 Uiso calc U . R 1 . .
C C8 0.4696(3) 0.31470(18) 0.51997(15) 0.0300(5) Uani d . . . 1 . .
C C9 0.5598(3) 0.41736(16) 0.53406(14) 0.0258(4) Uani d . . . 1 . .
C C10 0.6152(4) 0.45435(18) 0.62510(15) 0.0326(5) Uani d . . . 1 . .
H H4 0.711109 0.510684 0.620053 0.049 Uiso calc U . R 1 . .
H H3 0.670452 0.395714 0.658875 0.049 Uiso calc U . R 1 . .
H H5 0.500479 0.480871 0.656015 0.049 Uiso calc U . R 1 . .
C C11 0.5834(3) 0.46698(15) 0.45570(14) 0.0230(4) Uani d . . . 1 . .
C C12 0.5159(3) 0.40019(16) 0.37710(14) 0.0259(4) Uani d . . . 1 . .
C C13 0.6727(3) 0.57419(16) 0.44822(13) 0.0270(4) Uani d . . . 1 . .
H H11 0.806793 0.569246 0.470754 0.032 Uiso calc U . R 1 . .
H H10 0.601628 0.621513 0.489021 0.032 Uiso calc U . R 1 . .
C C14 0.4535(3) 0.29572(16) 0.42140(16) 0.0316(5) Uani d . . . 1 . .
H H19 0.319064 0.277739 0.404876 0.038 Uiso calc U . R 1 . .
H H18 0.539565 0.237587 0.402816 0.038 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.224(3) ?
O3 C12 . 1.434(3) ?
O3 H22 . 0.86(4) ?
C1 C2 . 1.505(3) ?
C1 H1 . 0.98 ?
C1 H12 . 0.98 ?
C1 H13 . 0.98 ?
C2 C15 . 1.325(3) ?
C2 C3 . 1.520(3) ?
C3 C13 . 1.538(3) ?
C3 C4 . 1.540(3) ?
C3 H9 . 1.0 ?
C4 C5 . 1.527(3) ?
C4 H7 . 0.99 ?
C4 H8 . 0.99 ?
C5 C6 . 1.540(3) ?
C5 H6 . 0.99 ?
C5 H14 . 0.99 ?
C6 C7 . 1.530(3) ?
C6 C12 . 1.546(3) ?
C6 H15 . 1.0 ?
C15 H21 . 0.93(3) ?
C15 H20 . 0.98(3) ?
C7 H2 . 0.98 ?
C7 H17 . 0.98 ?
C7 H16 . 0.98 ?
C8 C9 . 1.464(3) ?
C8 C14 . 1.504(3) ?
C9 C11 . 1.345(3) ?
C9 C10 . 1.496(3) ?
C10 H4 . 0.98 ?
C10 H3 . 0.98 ?
C10 H5 . 0.98 ?
C11 C13 . 1.502(3) ?
C11 C12 . 1.528(3) ?
C12 C14 . 1.548(3) ?
C13 H11 . 0.99 ?
C13 H10 . 0.99 ?
C14 H19 . 0.99 ?
C14 H18 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O3 H22 . . 107.(2) ?
C2 C1 H1 . . 109.5 ?
C2 C1 H12 . . 109.5 ?
H1 C1 H12 . . 109.5 ?
C2 C1 H13 . . 109.5 ?
H1 C1 H13 . . 109.5 ?
H12 C1 H13 . . 109.5 ?
C15 C2 C1 . . 121.6(2) ?
C15 C2 C3 . . 120.9(2) ?
C1 C2 C3 . . 117.5(2) ?
C2 C3 C13 . . 109.64(16) ?
C2 C3 C4 . . 110.78(16) ?
C13 C3 C4 . . 112.83(17) ?
C2 C3 H9 . . 107.8 ?
C13 C3 H9 . . 107.8 ?
C4 C3 H9 . . 107.8 ?
C5 C4 C3 . . 114.24(17) ?
C5 C4 H7 . . 108.7 ?
C3 C4 H7 . . 108.7 ?
C5 C4 H8 . . 108.7 ?
C3 C4 H8 . . 108.7 ?
H7 C4 H8 . . 107.6 ?
C4 C5 C6 . . 117.16(18) ?
C4 C5 H6 . . 108.0 ?
C6 C5 H6 . . 108.0 ?
C4 C5 H14 . . 108.0 ?
C6 C5 H14 . . 108.0 ?
H6 C5 H14 . . 107.3 ?
C7 C6 C5 . . 111.44(18) ?
C7 C6 C12 . . 111.90(18) ?
C5 C6 C12 . . 113.80(17) ?
C7 C6 H15 . . 106.4 ?
C5 C6 H15 . . 106.4 ?
C12 C6 H15 . . 106.4 ?
C2 C15 H21 . . 121.4(18) ?
C2 C15 H20 . . 122.0(18) ?
H21 C15 H20 . . 117.(3) ?
C6 C7 H2 . . 109.5 ?
C6 C7 H17 . . 109.5 ?
H2 C7 H17 . . 109.5 ?
C6 C7 H16 . . 109.5 ?
H2 C7 H16 . . 109.5 ?
H17 C7 H16 . . 109.5 ?
O1 C8 C9 . . 125.3(2) ?
O1 C8 C14 . . 126.3(2) ?
C9 C8 C14 . . 108.49(18) ?
C11 C9 C8 . . 110.16(19) ?
C11 C9 C10 . . 128.34(19) ?
C8 C9 C10 . . 121.50(19) ?
C9 C10 H4 . . 109.5 ?
C9 C10 H3 . . 109.5 ?
H4 C10 H3 . . 109.5 ?
C9 C10 H5 . . 109.5 ?
H4 C10 H5 . . 109.5 ?
H3 C10 H5 . . 109.5 ?
C9 C11 C13 . . 122.81(19) ?
C9 C11 C12 . . 112.16(18) ?
C13 C11 C12 . . 125.00(18) ?
O3 C12 C11 . . 110.41(16) ?
O3 C12 C6 . . 106.66(17) ?
C11 C12 C6 . . 114.09(17) ?
O3 C12 C14 . . 111.78(17) ?
C11 C12 C14 . . 103.38(17) ?
C6 C12 C14 . . 110.63(17) ?
C11 C13 C3 . . 118.90(17) ?
C11 C13 H11 . . 107.6 ?
C3 C13 H11 . . 107.6 ?
C11 C13 H10 . . 107.6 ?
C3 C13 H10 . . 107.6 ?
H11 C13 H10 . . 107.0 ?
C8 C14 C12 . . 105.32(18) ?
C8 C14 H19 . . 110.7 ?
C12 C14 H19 . . 110.7 ?
C8 C14 H18 . . 110.7 ?
C12 C14 H18 . . 110.7 ?
H19 C14 H18 . . 108.8 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 C2 C3 C13 . . . . 113.1(2) ?
C1 C2 C3 C13 . . . . -68.8(2) ?
C15 C2 C3 C4 . . . . -121.7(2) ?
C1 C2 C3 C4 . . . . 56.3(3) ?
C2 C3 C4 C5 . . . . 154.03(18) ?
C13 C3 C4 C5 . . . . -82.6(2) ?
C3 C4 C5 C6 . . . . 70.7(2) ?
C4 C5 C6 C7 . . . . 63.7(2) ?
C4 C5 C6 C12 . . . . -64.0(3) ?
O1 C8 C9 C11 . . . . -174.2(2) ?
C14 C8 C9 C11 . . . . 5.8(2) ?
O1 C8 C9 C10 . . . . 6.6(3) ?
C14 C8 C9 C10 . . . . -173.38(19) ?
C8 C9 C11 C13 . . . . -179.93(18) ?
C10 C9 C11 C13 . . . . -0.8(3) ?
C8 C9 C11 C12 . . . . -1.9(2) ?
C10 C9 C11 C12 . . . . 177.2(2) ?
C9 C11 C12 O3 . . . . -122.30(19) ?
C13 C11 C12 O3 . . . . 55.7(2) ?
C9 C11 C12 C6 . . . . 117.6(2) ?
C13 C11 C12 C6 . . . . -64.4(3) ?
C9 C11 C12 C14 . . . . -2.6(2) ?
C13 C11 C12 C14 . . . . 175.39(19) ?
C7 C6 C12 O3 . . . . -176.44(16) ?
C5 C6 C12 O3 . . . . -49.0(2) ?
C7 C6 C12 C11 . . . . -54.3(2) ?
C5 C6 C12 C11 . . . . 73.2(2) ?
C7 C6 C12 C14 . . . . 61.8(2) ?
C5 C6 C12 C14 . . . . -170.78(18) ?
C9 C11 C13 C3 . . . . -175.70(19) ?
C12 C11 C13 C3 . . . . 6.5(3) ?
C2 C3 C13 C11 . . . . -178.20(19) ?
C4 C3 C13 C11 . . . . 57.8(3) ?
O1 C8 C14 C12 . . . . 172.9(2) ?
C9 C8 C14 C12 . . . . -7.2(2) ?
O3 C12 C14 C8 . . . . 124.55(18) ?
C11 C12 C14 C8 . . . . 5.8(2) ?
C6 C12 C14 C8 . . . . -116.74(19) ?

####################################################################### 
# 
# 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_rdp60_2
_database_code_depnum_ccdc_archive 'CCDC 2195144'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-06
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   20.4454(19)
_cell_length_b                   8.2080(6)
_cell_length_c                   8.1965(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1375.50(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3860
_cell_measurement_theta_min      5.7450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5028
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.275
_diffrn_reflns_theta_min         4.325
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  66.00   1.00    2.00    --   40.73 -57.00-150.00   94
  2  ω     62.00  91.00   1.00    2.00    --   40.73-125.00-180.00   29
  3  ω     64.00 135.00   1.00    3.00    --  108.20  15.00  30.00   71
  4  ω     62.00 131.00   1.00    3.00    --  108.20 -45.00 150.00   69
  5  ω    103.00 172.00   1.00    3.00    --  108.20 125.00 -30.00   69
  6  ω     99.00 125.00   1.00    3.00    --  108.20 125.00  60.00   26
  7  ω   -115.00 -36.00   1.00    2.00    --  -40.98 -38.00  30.00   79
  8  ω     27.00  53.00   1.00    2.00    --   40.98-122.00  61.00   26
  9  ω     35.00  81.00   1.00    3.00    --  108.20-125.00-150.00   46
 10  ω     84.00 117.00   1.00    3.00    --  108.20-125.00-150.00   33
 11  ω     37.00  95.00   1.00    3.00    --  108.20 -94.00  90.00   58
 12  ω     78.00 129.00   1.00    3.00    --  108.20 -45.00-150.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0159423000
_diffrn_orient_matrix_UB_12      -0.1823042000
_diffrn_orient_matrix_UB_13      -0.0194469000
_diffrn_orient_matrix_UB_21      -0.0732709000
_diffrn_orient_matrix_UB_22      -0.0374193000
_diffrn_orient_matrix_UB_23      -0.0231901000
_diffrn_orient_matrix_UB_31      0.0075408000
_diffrn_orient_matrix_UB_32      0.0239614000
_diffrn_orient_matrix_UB_33      -0.1855228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                2237
_reflns_number_total             2681
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.062
_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)+(0.1056P)²+0.5200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.1976
_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.a Ternary CH refined with riding coordinates:
 C2(H2A), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.29522(15) -0.6714(4) -0.4240(4) 0.0300(7) Uani 1 1 d . . . . .
O2 O -0.31790(17) -1.0037(4) -0.6422(4) 0.0352(8) Uani 1 1 d . . . . .
H2 H -0.297613 -0.999772 -0.728433 0.053 Uiso 1 1 calc R U . . .
O3 O -0.26078(18) -0.8788(4) -0.9034(4) 0.0403(8) Uani 1 1 d . . . . .
H3 H -0.243559 -0.917573 -0.984942 0.060 Uiso 1 1 calc R U . . .
C1 C -0.3840(2) -0.4931(5) -0.5915(6) 0.0332(10) Uani 1 1 d . . . . .
C2 C -0.4288(3) -0.3587(6) -0.6505(7) 0.0405(11) Uani 1 1 d . . . . .
H2A H -0.403591 -0.257704 -0.660832 0.049 Uiso 1 1 calc R U . . .
C3 C -0.4772(4) -0.3413(9) -0.5073(8) 0.069(2) Uani 1 1 d . . . . .
H3A H -0.509553 -0.262180 -0.497928 0.082 Uiso 1 1 calc R U . . .
C4 C -0.4630(3) -0.4762(7) -0.3832(7) 0.0489(14) Uani 1 1 d . . . . .
H4 H -0.486514 -0.503491 -0.289966 0.059 Uiso 1 1 calc R U . . .
C5 C -0.4014(2) -0.5541(6) -0.4492(6) 0.0347(10) Uani 1 1 d . . . . .
C6 C -0.3621(2) -0.6884(6) -0.3708(6) 0.0335(10) Uani 1 1 d . . . . .
C7 C -0.3809(2) -0.8531(6) -0.4432(6) 0.0359(11) Uani 1 1 d . . . . .
H7A H -0.427980 -0.863324 -0.453827 0.043 Uiso 1 1 calc R U . . .
H7B H -0.364509 -0.942053 -0.376963 0.043 Uiso 1 1 calc R U . . .
C8 C -0.3475(2) -0.8498(5) -0.6114(6) 0.0335(10) Uani 1 1 d . . . . .
H8 H -0.379898 -0.825785 -0.696201 0.040 Uiso 1 1 calc R U . . .
C9 C -0.2972(2) -0.7041(5) -0.5972(5) 0.0281(9) Uani 1 1 d . . . . .
C10 C -0.3249(2) -0.5522(5) -0.6821(5) 0.0320(10) Uani 1 1 d . . . . .
H10A H -0.291926 -0.467169 -0.684680 0.038 Uiso 1 1 calc R U . . .
H10B H -0.336693 -0.578472 -0.793663 0.038 Uiso 1 1 calc R U . . .
C11 C -0.4615(3) -0.3956(8) -0.8127(7) 0.0483(14) Uani 1 1 d . . . . .
H11A H -0.428703 -0.413815 -0.894355 0.072 Uiso 1 1 calc R U . . .
H11B H -0.488409 -0.304940 -0.844219 0.072 Uiso 1 1 calc R U . . .
H11C H -0.488221 -0.491218 -0.801984 0.072 Uiso 1 1 calc R U . . .
C12 C -0.3622(3) -0.6823(7) -0.1842(6) 0.0456(13) Uani 1 1 d . . . . .
H12A H -0.337725 -0.772904 -0.142117 0.068 Uiso 1 1 calc R U . . .
H12B H -0.406370 -0.687861 -0.145075 0.068 Uiso 1 1 calc R U . . .
H12C H -0.342463 -0.582378 -0.148371 0.068 Uiso 1 1 calc R U . . .
C13 C -0.2296(2) -0.7457(5) -0.6541(6) 0.0305(9) Uani 1 1 d . . . . .
C14 C -0.1802(3) -0.7703(6) -0.5521(7) 0.0423(12) Uani 1 1 d . . . . .
H14A H -0.139(3) -0.810(8) -0.576(7) 0.048(17) Uiso 1 1 d . . . . .
H14B H -0.185(3) -0.765(9) -0.435(8) 0.06(2) Uiso 1 1 d . . . . .
C15 C -0.2192(3) -0.7536(6) -0.8366(6) 0.0377(11) Uani 1 1 d . . . . .
H15A H -0.229845 -0.649319 -0.885572 0.045 Uiso 1 1 calc R U . . .
H15B H -0.173815 -0.778116 -0.860235 0.045 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 C6 1.442(5) . ?
O1 C9 1.445(5) . ?
O2 H2 0.8200 . ?
O2 C8 1.424(6) . ?
O3 H3 0.8200 . ?
O3 C15 1.441(6) . ?
C1 C2 1.513(7) . ?
C1 C5 1.318(7) . ?
C1 C10 1.499(6) . ?
C2 H2A 0.9800 . ?
C2 C3 1.541(8) . ?
C2 C11 1.518(8) . ?
C3 H3A 0.9300 . ?
C3 C4 1.532(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.513(7) . ?
C5 C6 1.508(7) . ?
C6 C7 1.526(6) . ?
C6 C12 1.530(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.538(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.581(6) . ?
C9 C10 1.536(6) . ?
C9 C13 1.499(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.326(7) . ?
C13 C15 1.512(6) . ?
C14 H14A 0.92(6) . ?
C14 H14B 0.96(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C9 104.6(3) . . ?
C8 O2 H2 109.5 . . ?
C15 O3 H3 109.5 . . ?
C5 C1 C2 113.3(4) . . ?
C5 C1 C10 122.2(4) . . ?
C10 C1 C2 124.5(4) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 C3 102.3(4) . . ?
C1 C2 C11 113.7(4) . . ?
C3 C2 H2A 109.0 . . ?
C11 C2 H2A 109.0 . . ?
C11 C2 C3 113.7(5) . . ?
C2 C3 H3A 125.7 . . ?
C4 C3 C2 108.5(5) . . ?
C4 C3 H3A 125.7 . . ?
C3 C4 H4 128.5 . . ?
C5 C4 C3 103.0(5) . . ?
C5 C4 H4 128.5 . . ?
C1 C5 C4 112.4(5) . . ?
C1 C5 C6 120.8(4) . . ?
C6 C5 C4 126.9(4) . . ?
O1 C6 C5 107.8(4) . . ?
O1 C6 C7 101.9(4) . . ?
O1 C6 C12 107.5(4) . . ?
C5 C6 C7 110.3(4) . . ?
C5 C6 C12 113.7(4) . . ?
C7 C6 C12 114.7(4) . . ?
C6 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C6 C7 C8 102.8(4) . . ?
H7A C7 H7B 109.1 . . ?
C8 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
O2 C8 C7 109.4(4) . . ?
O2 C8 H8 109.8 . . ?
O2 C8 C9 114.1(4) . . ?
C7 C8 H8 109.8 . . ?
C7 C8 C9 103.6(4) . . ?
C9 C8 H8 109.8 . . ?
O1 C9 C8 103.4(3) . . ?
O1 C9 C10 107.8(3) . . ?
O1 C9 C13 108.8(4) . . ?
C10 C9 C8 110.0(4) . . ?
C13 C9 C8 113.9(4) . . ?
C13 C9 C10 112.5(4) . . ?
C1 C10 C9 109.6(4) . . ?
C1 C10 H10A 109.8 . . ?
C1 C10 H10B 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C15 116.5(4) . . ?
C14 C13 C9 122.7(4) . . ?
C14 C13 C15 120.7(5) . . ?
C13 C14 H14A 128(4) . . ?
C13 C14 H14B 123(4) . . ?
H14A C14 H14B 109(5) . . ?
O3 C15 C13 108.9(4) . . ?
O3 C15 H15A 109.9 . . ?
O3 C15 H15B 109.9 . . ?
C13 C15 H15A 109.9 . . ?
C13 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?

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 C6 C7 C8 -39.2(4) . . . . ?
O1 C9 C10 C1 -45.8(5) . . . . ?
O1 C9 C13 C14 9.1(6) . . . . ?
O1 C9 C13 C15 -169.1(3) . . . . ?
O2 C8 C9 O1 -105.2(4) . . . . ?
O2 C8 C9 C10 140.0(4) . . . . ?
O2 C8 C9 C13 12.6(5) . . . . ?
C1 C2 C3 C4 -6.0(7) . . . . ?
C1 C5 C6 O1 28.9(6) . . . . ?
C1 C5 C6 C7 -81.6(6) . . . . ?
C1 C5 C6 C12 147.9(5) . . . . ?
C2 C1 C5 C4 1.4(6) . . . . ?
C2 C1 C5 C6 -179.6(4) . . . . ?
C2 C1 C10 C9 -172.3(4) . . . . ?
C2 C3 C4 C5 6.8(7) . . . . ?
C3 C4 C5 C1 -5.1(7) . . . . ?
C3 C4 C5 C6 175.9(5) . . . . ?
C4 C5 C6 O1 -152.2(5) . . . . ?
C4 C5 C6 C7 97.3(6) . . . . ?
C4 C5 C6 C12 -33.2(7) . . . . ?
C5 C1 C2 C3 3.0(6) . . . . ?
C5 C1 C2 C11 -120.0(5) . . . . ?
C5 C1 C10 C9 8.5(6) . . . . ?
C5 C6 C7 C8 75.1(5) . . . . ?
C6 O1 C9 C8 -39.6(4) . . . . ?
C6 O1 C9 C10 76.8(4) . . . . ?
C6 O1 C9 C13 -160.9(3) . . . . ?
C6 C7 C8 O2 137.2(4) . . . . ?
C6 C7 C8 C9 15.2(5) . . . . ?
C7 C8 C9 O1 13.7(4) . . . . ?
C7 C8 C9 C10 -101.2(4) . . . . ?
C7 C8 C9 C13 131.5(4) . . . . ?
C8 C9 C10 C1 66.2(5) . . . . ?
C8 C9 C13 C14 -105.6(5) . . . . ?
C8 C9 C13 C15 76.2(5) . . . . ?
C9 O1 C6 C5 -66.0(4) . . . . ?
C9 O1 C6 C7 50.2(4) . . . . ?
C9 O1 C6 C12 171.1(4) . . . . ?
C9 C13 C15 O3 -61.2(5) . . . . ?
C10 C1 C2 C3 -176.3(5) . . . . ?
C10 C1 C2 C11 60.7(7) . . . . ?
C10 C1 C5 C4 -179.3(5) . . . . ?
C10 C1 C5 C6 -0.3(7) . . . . ?
C10 C9 C13 C14 128.4(5) . . . . ?
C10 C9 C13 C15 -49.8(5) . . . . ?
C11 C2 C3 C4 116.9(6) . . . . ?
C12 C6 C7 C8 -155.0(4) . . . . ?
C13 C9 C10 C1 -165.7(4) . . . . ?
C14 C13 C15 O3 120.6(5) . . . . ?

_olex2_date_sample_data_collection 2021-01-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.184
_oxdiff_exptl_absorpt_empirical_full_min 0.462
####################################################################### 
# 
# 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_RDP611_20211201
_database_code_depnum_ccdc_archive 'CCDC 2195139'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2022-08-05 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         250.32
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.3597(3)
_cell_length_b                   8.4494(4)
_cell_length_c                   15.2000(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.757(3)
_cell_angle_gamma                90
_cell_volume                     678.39(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3084
_cell_measurement_theta_min      2.9499
_cell_measurement_theta_max      68.3237
_cell_measurement_temperature    164.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      164.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            3899
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_full        68.40
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2107
_reflns_number_gt                1938
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1962
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_number_reflns         2107
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1474P)²+0.0538P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 667 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5373(7) 0.8173(4) 0.9361(2) 0.0415(8) Uani d . . . 1 . .
O O2 0.3670(5) 0.3241(4) 0.8780(2) 0.0351(7) Uani d . . . 1 . .
H H22 0.388(10) 0.312(8) 0.939(4) 0.031(12) Uiso d . . . 1 . .
O O3 0.9080(5) 0.4485(4) 0.7755(2) 0.0323(7) Uani d . . . 1 . .
H H21 1.040(10) 0.401(6) 0.813(3) 0.021(11) Uiso d . . . 1 . .
C C1 0.2069(9) 0.7992(5) 0.7571(3) 0.0353(9) Uani d . . . 1 . .
H H19 0.254416 0.851998 0.704902 0.053 Uiso calc U . R 1 . .
H H20 0.182589 0.878692 0.801811 0.053 Uiso calc U . R 1 . .
H H1 0.049114 0.740322 0.738906 0.053 Uiso calc U . R 1 . .
C C2 0.4124(8) 0.6875(5) 0.7961(3) 0.0297(9) Uani d . . . 1 . .
C C3 0.4935(8) 0.5576(5) 0.7577(3) 0.0281(9) Uani d . . . 1 . .
C C4 0.3934(9) 0.5164(5) 0.6617(3) 0.0353(10) Uani d . . . 1 . .
H H18 0.466802 0.593069 0.623954 0.042 Uiso calc U . R 1 . .
H H17 0.208349 0.534978 0.651443 0.042 Uiso calc U . R 1 . .
C C5 0.4369(8) 0.3504(5) 0.6265(3) 0.0296(9) Uani d . . . 1 . .
H H3 0.622183 0.337777 0.626088 0.035 Uiso calc U . R 1 . .
C C6 0.2990(9) 0.3401(5) 0.5309(3) 0.0345(10) Uani d . . . 1 . .
C C7 0.0851(11) 0.2589(8) 0.5065(4) 0.0532(14) Uani d . . . 1 . .
H H4 0.006129 0.257033 0.445605 0.064 Uiso calc U . R 1 . .
H H2 0.011648 0.202994 0.549919 0.064 Uiso calc U . R 1 . .
C C8 0.5629(8) 0.7088(5) 0.8848(3) 0.0324(9) Uani d . . . 1 . .
C C9 0.4168(11) 0.4285(7) 0.4637(3) 0.0471(12) Uani d . . . 1 . .
H H5 0.319066 0.410206 0.404034 0.071 Uiso calc U . R 1 . .
H H6 0.590969 0.391632 0.46556 0.071 Uiso calc U . R 1 . .
H H7 0.417931 0.541919 0.477351 0.071 Uiso calc U . R 1 . .
C C10 0.3563(8) 0.2222(5) 0.6872(3) 0.0324(9) Uani d . . . 1 . .
H H16 0.200299 0.257447 0.708274 0.039 Uiso calc U . R 1 . .
H H15 0.314948 0.124538 0.65179 0.039 Uiso calc U . R 1 . .
C C11 0.5573(8) 0.1833(5) 0.7685(3) 0.0342(9) Uani d . . . 1 . .
H H8 0.720367 0.168715 0.747155 0.041 Uiso calc U . R 1 . .
H H14 0.512312 0.079958 0.792256 0.041 Uiso calc U . R 1 . .
C C12 0.6019(7) 0.3003(5) 0.8464(3) 0.0290(9) Uani d . . . 1 . .
C C13 0.7964(8) 0.2217(6) 0.9189(3) 0.0349(10) Uani d . . . 1 . .
H H9 0.816854 0.285655 0.973399 0.052 Uiso calc U . R 1 . .
H H11 0.959322 0.21356 0.898081 0.052 Uiso calc U . R 1 . .
H H10 0.737375 0.115604 0.931413 0.052 Uiso calc U . R 1 . .
C C14 0.6971(7) 0.4663(5) 0.8202(3) 0.0268(8) Uani d . . . 1 . .
C C15 0.7514(8) 0.5759(6) 0.9021(3) 0.0352(10) Uani d . . . 1 . .
H H12 0.730937 0.517841 0.956974 0.042 Uiso calc U . R 1 . .
H H13 0.926396 0.617555 0.909372 0.042 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 . 1.225(6) ?
O2 C12 . 1.435(4) ?
O2 H22 . 0.92(6) ?
O3 C14 . 1.423(5) ?
O3 H21 . 0.92(6) ?
C1 C2 . 1.495(6) ?
C1 H19 . 0.98 ?
C1 H20 . 0.98 ?
C1 H1 . 0.98 ?
C2 C3 . 1.349(6) ?
C2 C8 . 1.461(6) ?
C3 C4 . 1.508(5) ?
C3 C14 . 1.529(6) ?
C4 C5 . 1.532(6) ?
C4 H18 . 0.99 ?
C4 H17 . 0.99 ?
C5 C6 . 1.517(5) ?
C5 C10 . 1.532(6) ?
C5 H3 . 1.0 ?
C6 C7 . 1.334(7) ?
C6 C9 . 1.490(7) ?
C7 H4 . 0.95 ?
C7 H2 . 0.95 ?
C8 C15 . 1.504(6) ?
C9 H5 . 0.98 ?
C9 H6 . 0.98 ?
C9 H7 . 0.98 ?
C10 C11 . 1.530(6) ?
C10 H16 . 0.99 ?
C10 H15 . 0.99 ?
C11 C12 . 1.531(6) ?
C11 H8 . 0.99 ?
C11 H14 . 0.99 ?
C12 C13 . 1.534(5) ?
C12 C14 . 1.567(5) ?
C13 H9 . 0.98 ?
C13 H11 . 0.98 ?
C13 H10 . 0.98 ?
C14 C15 . 1.539(6) ?
C15 H12 . 0.99 ?
C15 H13 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 H22 . . 111.(3) ?
C14 O3 H21 . . 110.(3) ?
C2 C1 H19 . . 109.5 ?
C2 C1 H20 . . 109.5 ?
H19 C1 H20 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H19 C1 H1 . . 109.5 ?
H20 C1 H1 . . 109.5 ?
C3 C2 C8 . . 109.4(4) ?
C3 C2 C1 . . 127.8(4) ?
C8 C2 C1 . . 122.8(4) ?
C2 C3 C4 . . 121.2(4) ?
C2 C3 C14 . . 112.9(4) ?
C4 C3 C14 . . 125.8(4) ?
C3 C4 C5 . . 119.9(4) ?
C3 C4 H18 . . 107.3 ?
C5 C4 H18 . . 107.3 ?
C3 C4 H17 . . 107.3 ?
C5 C4 H17 . . 107.3 ?
H18 C4 H17 . . 106.9 ?
C6 C5 C10 . . 113.3(4) ?
C6 C5 C4 . . 107.9(3) ?
C10 C5 C4 . . 111.2(3) ?
C6 C5 H3 . . 108.1 ?
C10 C5 H3 . . 108.1 ?
C4 C5 H3 . . 108.1 ?
C7 C6 C9 . . 120.7(4) ?
C7 C6 C5 . . 123.5(4) ?
C9 C6 C5 . . 115.7(4) ?
C6 C7 H4 . . 120.0 ?
C6 C7 H2 . . 120.0 ?
H4 C7 H2 . . 120.0 ?
O1 C8 C2 . . 125.2(4) ?
O1 C8 C15 . . 126.3(4) ?
C2 C8 C15 . . 108.6(4) ?
C6 C9 H5 . . 109.5 ?
C6 C9 H6 . . 109.5 ?
H5 C9 H6 . . 109.5 ?
C6 C9 H7 . . 109.5 ?
H5 C9 H7 . . 109.5 ?
H6 C9 H7 . . 109.5 ?
C11 C10 C5 . . 114.0(3) ?
C11 C10 H16 . . 108.8 ?
C5 C10 H16 . . 108.8 ?
C11 C10 H15 . . 108.8 ?
C5 C10 H15 . . 108.8 ?
H16 C10 H15 . . 107.7 ?
C10 C11 C12 . . 118.8(4) ?
C10 C11 H8 . . 107.6 ?
C12 C11 H8 . . 107.6 ?
C10 C11 H14 . . 107.6 ?
C12 C11 H14 . . 107.6 ?
H8 C11 H14 . . 107.1 ?
O2 C12 C11 . . 108.6(3) ?
O2 C12 C13 . . 110.4(3) ?
C11 C12 C13 . . 105.9(4) ?
O2 C12 C14 . . 107.6(3) ?
C11 C12 C14 . . 113.4(3) ?
C13 C12 C14 . . 111.0(3) ?
C12 C13 H9 . . 109.5 ?
C12 C13 H11 . . 109.5 ?
H9 C13 H11 . . 109.5 ?
C12 C13 H10 . . 109.5 ?
H9 C13 H10 . . 109.5 ?
H11 C13 H10 . . 109.5 ?
O3 C14 C3 . . 107.3(3) ?
O3 C14 C15 . . 113.2(3) ?
C3 C14 C15 . . 102.5(3) ?
O3 C14 C12 . . 110.2(3) ?
C3 C14 C12 . . 112.4(3) ?
C15 C14 C12 . . 111.0(3) ?
C8 C15 C14 . . 106.2(3) ?
C8 C15 H12 . . 110.5 ?
C14 C15 H12 . . 110.5 ?
C8 C15 H13 . . 110.5 ?
C14 C15 H13 . . 110.5 ?
H12 C15 H13 . . 108.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C2 C3 C4 . . . . -172.9(4) ?
C1 C2 C3 C4 . . . . 5.7(7) ?
C8 C2 C3 C14 . . . . 5.0(5) ?
C1 C2 C3 C14 . . . . -176.4(4) ?
C2 C3 C4 C5 . . . . -165.0(4) ?
C14 C3 C4 C5 . . . . 17.4(6) ?
C3 C4 C5 C6 . . . . 175.7(4) ?
C3 C4 C5 C10 . . . . 50.9(5) ?
C10 C5 C6 C7 . . . . 17.3(6) ?
C4 C5 C6 C7 . . . . -106.3(6) ?
C10 C5 C6 C9 . . . . -163.1(4) ?
C4 C5 C6 C9 . . . . 73.3(5) ?
C3 C2 C8 O1 . . . . 179.1(4) ?
C1 C2 C8 O1 . . . . 0.4(6) ?
C3 C2 C8 C15 . . . . -1.1(5) ?
C1 C2 C8 C15 . . . . -179.7(4) ?
C6 C5 C10 C11 . . . . 155.2(4) ?
C4 C5 C10 C11 . . . . -83.0(5) ?
C5 C10 C11 C12 . . . . 74.8(5) ?
C10 C11 C12 O2 . . . . 57.1(5) ?
C10 C11 C12 C13 . . . . 175.7(3) ?
C10 C11 C12 C14 . . . . -62.3(5) ?
C2 C3 C14 O3 . . . . -126.1(4) ?
C4 C3 C14 O3 . . . . 51.7(5) ?
C2 C3 C14 C15 . . . . -6.6(4) ?
C4 C3 C14 C15 . . . . 171.1(4) ?
C2 C3 C14 C12 . . . . 112.6(4) ?
C4 C3 C14 C12 . . . . -69.6(5) ?
O2 C12 C14 O3 . . . . -170.9(3) ?
C11 C12 C14 O3 . . . . -50.9(4) ?
C13 C12 C14 O3 . . . . 68.2(4) ?
O2 C12 C14 C3 . . . . -51.3(4) ?
C11 C12 C14 C3 . . . . 68.7(4) ?
C13 C12 C14 C3 . . . . -172.2(3) ?
O2 C12 C14 C15 . . . . 62.9(4) ?
C11 C12 C14 C15 . . . . -177.1(3) ?
C13 C12 C14 C15 . . . . -58.0(4) ?
O1 C8 C15 C14 . . . . 176.7(4) ?
C2 C8 C15 C14 . . . . -3.1(4) ?
O3 C14 C15 C8 . . . . 120.7(4) ?
C3 C14 C15 C8 . . . . 5.5(4) ?
C12 C14 C15 C8 . . . . -114.7(4) ?

