# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_caopeng
_database_code_depnum_ccdc_archive 'CCDC 2047490'
loop_
_audit_author_name
_audit_author_address
'Feijie Song'
;Sichuan Normal University
China
;
_audit_update_record             
;
2020-12-01 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_audit_creation_date             2020-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.7772(3)
_cell_length_b                   7.78040(10)
_cell_length_c                   15.2918(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.3770(10)
_cell_angle_gamma                90
_cell_volume                     2763.17(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14401
_cell_measurement_temperature    293.26(10)
_cell_measurement_theta_max      76.1390
_cell_measurement_theta_min      3.1230
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25147
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.056
_diffrn_reflns_theta_min         5.715
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.26(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  16.00   0.50    0.05    --  -45.87 102.00 150.00  196
  2  ω    -12.00  82.00   0.50    0.05    --   45.87-102.00  46.00  188
  3  ω   -175.00 -83.00   0.50    0.05    -- -102.00-102.00  46.00  184
  4  ω   -110.00 -29.00   0.50    0.05    -- -102.00 102.00 150.00  162
  5  ω     33.00 110.00   0.50    0.05    --  106.06-102.00  46.00  154
  6  ω     87.00 178.00   0.50    0.05    --  106.06 102.00 150.00  182
  7  ω   -119.00 -71.00   0.50    0.05    --  -45.87-125.00-150.00   96
  8  ω   -121.00 -30.00   0.50    0.05    --  -45.87 -19.00 -30.00  182
  9  ω   -119.00 -71.00   0.50    0.05    --  -45.87-125.00-180.00   96
 10  ω    -24.00  30.00   0.50    0.05    --  -45.87  19.00 -90.00  108
 11  ω    -29.00  28.00   0.50    0.05    --   45.87 -19.00 -30.00  114
 12  ω   -174.00 -87.00   0.50    0.05    -- -102.00 -45.00  90.00  174
 13  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00-120.00   80
 14  ω   -117.00 -29.00   0.50    0.05    -- -102.00 125.00-180.00  176
 15  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -30.00   80
 16  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -60.00   80
 17  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -90.00   80
 18  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  90.00   80
 19  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00   0.00   80
 20  ω     33.00 108.00   0.50    0.05    --  106.06 -77.00  30.00  150
 21  ω     33.00  73.00   0.50    0.05    --  106.06 -61.00  90.00   80
 22  ω     33.00  73.00   0.50    0.05    --  106.06 -61.00  30.00   80
 23  ω     33.00  64.00   0.50    0.05    --  106.06 -77.00-150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0648334000
_diffrn_orient_matrix_UB_12      0.0274873000
_diffrn_orient_matrix_UB_13      0.0056754000
_diffrn_orient_matrix_UB_21      0.0055454000
_diffrn_orient_matrix_UB_22      -0.1873866000
_diffrn_orient_matrix_UB_23      -0.0296465000
_diffrn_orient_matrix_UB_31      -0.0128463000
_diffrn_orient_matrix_UB_32      0.0579154000
_diffrn_orient_matrix_UB_33      -0.0986278000
_diffrn_oxdiff_digest_frames     
;
0137d966191114d8d731a025f39baeb97c0011485a8
;
_diffrn_oxdiff_digest_hkl        
;
013d3148dccb1636dc2d62d350fde07602dd01
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4947
_reflns_number_total             5500
_reflns_odcompleteness_completeness 99.51
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5500
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.020
_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)+(0.0694P)²+0.4602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1311
_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. Rigid bond restraints
 C10, C12
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C12: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(H12E)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C9(H9A,H9B), C17(H17A,H17B), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C6(H6), C26(H26), C2(H2), C1(H1), C27(H27)
5.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B), C12(H12A,H12B), C11A(H11D,H11E)
5.e Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C4(H4A,H4B,H4C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C), C16(H16A,H16B,H16C), C11(H11A,H11B,H11C), C12A(H12C,H12D,H12E)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O4 O 0.17378(4) 0.07642(16) 0.43545(6) 0.0708(3) Uani 1 1 d . U . . .
H4 H 0.2068 0.1006 0.4321 0.106 Uiso 1 1 calc GR . . . .
O3 O 0.28190(4) 0.19105(14) 0.42713(7) 0.0657(3) Uani 1 1 d . U . . .
O2 O 0.34538(4) 0.07673(15) 0.11119(6) 0.0671(3) Uani 1 1 d . U . . .
H2A H 0.3118 0.0990 0.1122 0.101 Uiso 1 1 calc GR . . . .
O1 O 0.23475(4) 0.19011(14) 0.12186(6) 0.0655(3) Uani 1 1 d . U . . .
C24 C 0.39497(5) 0.24704(15) 0.33904(7) 0.0433(3) Uani 1 1 d . U . . .
C5 C 0.11710(5) 0.20258(15) 0.20092(7) 0.0442(3) Uani 1 1 d . U . . .
C29 C 0.35903(5) 0.20397(15) 0.25795(8) 0.0455(3) Uani 1 1 d . U . . .
H29 H 0.3200 0.2301 0.2484 0.055 Uiso 1 1 calc R . . . .
C6 C 0.15554(5) 0.17459(16) 0.28200(8) 0.0472(3) Uani 1 1 d . U . . .
H6 H 0.1942 0.2021 0.2872 0.057 Uiso 1 1 calc R . . . .
C19 C 0.36750(5) 0.33259(15) 0.40976(7) 0.0444(3) Uani 1 1 d . U . . .
H19 H 0.3983 0.3748 0.4582 0.053 Uiso 1 1 calc R . . . .
C25 C 0.45384(5) 0.20685(17) 0.35462(9) 0.0523(3) Uani 1 1 d . U . . .
C20 C 0.32767(5) 0.48283(16) 0.37459(8) 0.0495(3) Uani 1 1 d . U . . .
H20A H 0.2965 0.4385 0.3286 0.059 Uiso 1 1 calc R . . . .
H20B H 0.3108 0.5230 0.4233 0.059 Uiso 1 1 calc R . . . .
C13 C 0.18342(5) 0.16585(16) 0.09716(7) 0.0487(3) Uani 1 1 d . U . . .
C18 C 0.33395(5) 0.19343(16) 0.44781(7) 0.0472(3) Uani 1 1 d . U . . .
C9 C 0.16688(5) 0.46417(16) 0.15179(8) 0.0512(3) Uani 1 1 d . U . . .
H9A H 0.1985 0.4510 0.2032 0.061 Uiso 1 1 calc R . . . .
H9B H 0.1825 0.5087 0.1027 0.061 Uiso 1 1 calc R . . . .
C8 C 0.14026(5) 0.28673(16) 0.12538(7) 0.0457(3) Uani 1 1 d . U . . .
H8 H 0.1080 0.3021 0.0741 0.055 Uiso 1 1 calc R . . . .
C3 C 0.05917(5) 0.15640(17) 0.19150(9) 0.0525(3) Uani 1 1 d . U . . .
C28 C 0.38015(6) 0.12271(17) 0.19095(8) 0.0520(3) Uani 1 1 d . U . . .
C7 C 0.13751(5) 0.10661(17) 0.35509(8) 0.0523(3) Uani 1 1 d . U . . .
C21 C 0.35232(6) 0.63580(17) 0.33650(9) 0.0550(3) Uani 1 1 d . U . . .
C10 C 0.12493(6) 0.59256(18) 0.17428(10) 0.0584(3) Uani 1 1 d . U . . .
C17 C 0.36744(6) 0.06005(19) 0.50773(10) 0.0627(3) Uani 1 1 d . U . . .
H17A H 0.3948 0.1178 0.5547 0.075 Uiso 1 1 calc R . . . .
H17B H 0.3893 -0.0071 0.4732 0.075 Uiso 1 1 calc R . . . .
C26 C 0.47387(6) 0.1269(2) 0.28564(11) 0.0647(4) Uani 1 1 d . U . . .
H26 H 0.5128 0.1007 0.2944 0.078 Uiso 1 1 calc R . . . .
C2 C 0.04222(6) 0.0894(2) 0.26650(10) 0.0634(4) Uani 1 1 d . U . . .
H2 H 0.0038 0.0591 0.2616 0.076 Uiso 1 1 calc R . . . .
C30 C 0.49560(6) 0.2460(2) 0.44133(10) 0.0688(4) Uani 1 1 d . U . . .
H30A H 0.4931 0.3655 0.4555 0.103 Uiso 1 1 calc GR . . . .
H30B H 0.5340 0.2199 0.4352 0.103 Uiso 1 1 calc GR . . . .
H30C H 0.4863 0.1774 0.4885 0.103 Uiso 1 1 calc GR . . . .
C1 C 0.07988(6) 0.0666(2) 0.34695(9) 0.0626(4) Uani 1 1 d . U . . .
H1 H 0.0668 0.0245 0.3959 0.075 Uiso 1 1 calc R . . . .
C27 C 0.43826(6) 0.0852(2) 0.20510(10) 0.0656(4) Uani 1 1 d . U . . .
H27 H 0.4532 0.0321 0.1605 0.079 Uiso 1 1 calc R . . . .
C14 C 0.15903(7) 0.0182(2) 0.03821(11) 0.0706(4) Uani 1 1 d . U . . .
H14A H 0.1381 0.0638 -0.0185 0.085 Uiso 1 1 calc R . . . .
H14B H 0.1315 -0.0415 0.0658 0.085 Uiso 1 1 calc R . . . .
C4 C 0.01495(6) 0.1744(3) 0.10488(11) 0.0764(4) Uani 1 1 d . U . . .
H4A H 0.0123 0.2927 0.0867 0.115 Uiso 1 1 calc GR . . . .
H4B H -0.0218 0.1360 0.1136 0.115 Uiso 1 1 calc GR . . . .
H4C H 0.0263 0.1059 0.0594 0.115 Uiso 1 1 calc GR . . . .
C23 C 0.40756(7) 0.6664(2) 0.34454(13) 0.0781(5) Uani 1 1 d . U . . .
H23A H 0.4346 0.5899 0.3758 0.094 Uiso 1 1 calc R . . . .
H23B H 0.4196 0.7644 0.3189 0.094 Uiso 1 1 calc R . . . .
C12 C 0.0861(10) 0.657(3) 0.1196(15) 0.083(4) Uani 0.34(2) 1 d . U P A 1
H12A H 0.0809 0.6280 0.0594 0.099 Uiso 0.34(2) 1 calc R . P A 1
H12B H 0.0615 0.7361 0.1379 0.099 Uiso 0.34(2) 1 calc R . P A 1
C15 C 0.20220(8) -0.1097(2) 0.01995(13) 0.0854(5) Uani 1 1 d . U . . .
H15A H 0.2272 -0.0554 -0.0133 0.128 Uiso 1 1 calc GR . . . .
H15B H 0.1825 -0.2037 -0.0142 0.128 Uiso 1 1 calc GR . . . .
H15C H 0.2245 -0.1521 0.0756 0.128 Uiso 1 1 calc GR . . . .
C22 C 0.30751(9) 0.7590(2) 0.28909(15) 0.0953(6) Uani 1 1 d . U . . .
H22A H 0.2844 0.7038 0.2376 0.143 Uiso 1 1 calc GR . . . .
H22B H 0.3260 0.8580 0.2705 0.143 Uiso 1 1 calc GR . . . .
H22C H 0.2834 0.7940 0.3289 0.143 Uiso 1 1 calc GR . . . .
C16 C 0.33177(9) -0.0612(3) 0.55064(14) 0.0926(6) Uani 1 1 d . U . . .
H16A H 0.3046 -0.1198 0.5049 0.139 Uiso 1 1 calc GR . . . .
H16B H 0.3115 0.0029 0.5878 0.139 Uiso 1 1 calc GR . . . .
H16C H 0.3565 -0.1437 0.5865 0.139 Uiso 1 1 calc GR . . . .
C11 C 0.1387(11) 0.632(3) 0.2742(13) 0.114(6) Uani 0.34(2) 1 d . U P A 1
H11A H 0.1405 0.5266 0.3074 0.171 Uiso 0.34(2) 1 calc GR . P A 1
H11B H 0.1091 0.7043 0.2883 0.171 Uiso 0.34(2) 1 calc GR . P A 1
H11C H 0.1751 0.6899 0.2899 0.171 Uiso 0.34(2) 1 calc GR . P A 1
C11A C 0.1304(4) 0.6638(15) 0.2544(7) 0.097(2) Uani 0.66(2) 1 d . U P A 2
H11D H 0.1037 0.7448 0.2644 0.116 Uiso 0.66(2) 1 calc R . P A 2
H11E H 0.1609 0.6326 0.3007 0.116 Uiso 0.66(2) 1 calc R . P A 2
C12A C 0.0755(5) 0.6442(15) 0.1005(7) 0.0745(16) Uani 0.66(2) 1 d . U P A 2
H12C H 0.0899 0.6805 0.0494 0.112 Uiso 0.66(2) 1 calc GR . P A 2
H12D H 0.0549 0.7372 0.1205 0.112 Uiso 0.66(2) 1 calc GR . P A 2
H12E H 0.0501 0.5481 0.0843 0.112 Uiso 0.66(2) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 H4 0.8200 . ?
O4 C7 1.3619(15) . ?
O3 C18 1.2102(15) . ?
O2 H2A 0.8200 . ?
O2 C28 1.3663(16) . ?
O1 C13 1.2126(15) . ?
C24 C29 1.3877(16) . ?
C24 C19 1.5304(15) . ?
C24 C25 1.4039(16) . ?
C5 C6 1.3907(16) . ?
C5 C8 1.5294(16) . ?
C5 C3 1.4006(16) . ?
C29 H29 0.9300 . ?
C29 C28 1.3863(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.3850(16) . ?
C19 H19 0.9800 . ?
C19 C20 1.5278(17) . ?
C19 C18 1.5317(16) . ?
C25 C26 1.393(2) . ?
C25 C30 1.5075(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.4986(17) . ?
C13 C8 1.5209(16) . ?
C13 C14 1.4979(19) . ?
C18 C17 1.4959(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.5362(17) . ?
C9 C10 1.5026(18) . ?
C8 H8 0.9800 . ?
C3 C2 1.395(2) . ?
C3 C4 1.5108(19) . ?
C28 C27 1.3832(19) . ?
C7 C1 1.3845(18) . ?
C21 C23 1.314(2) . ?
C21 C22 1.499(2) . ?
C10 C12 1.21(2) . ?
C10 C11 1.524(19) . ?
C10 C11A 1.326(9) . ?
C10 C12A 1.499(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.509(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.376(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.369(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C1 H1 0.9300 . ?
C27 H27 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.498(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11A H11D 0.9300 . ?
C11A H11E 0.9300 . ?
C12A H12C 0.9600 . ?
C12A H12D 0.9600 . ?
C12A H12E 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
C7 O4 H4 109.5 . . ?
C28 O2 H2A 109.5 . . ?
C29 C24 C19 117.53(9) . . ?
C29 C24 C25 119.90(10) . . ?
C25 C24 C19 122.54(10) . . ?
C6 C5 C8 117.78(10) . . ?
C6 C5 C3 119.70(11) . . ?
C3 C5 C8 122.52(11) . . ?
C24 C29 H29 119.4 . . ?
C28 C29 C24 121.29(11) . . ?
C28 C29 H29 119.4 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.41(11) . . ?
C7 C6 H6 119.3 . . ?
C24 C19 H19 108.4 . . ?
C24 C19 C18 107.27(9) . . ?
C20 C19 C24 114.22(9) . . ?
C20 C19 H19 108.4 . . ?
C20 C19 C18 109.91(9) . . ?
C18 C19 H19 108.4 . . ?
C24 C25 C30 123.32(12) . . ?
C26 C25 C24 117.46(12) . . ?
C26 C25 C30 119.23(12) . . ?
C19 C20 H20A 107.6 . . ?
C19 C20 H20B 107.6 . . ?
H20A C20 H20B 107.1 . . ?
C21 C20 C19 118.67(10) . . ?
C21 C20 H20A 107.6 . . ?
C21 C20 H20B 107.6 . . ?
O1 C13 C8 120.70(11) . . ?
O1 C13 C14 122.73(12) . . ?
C14 C13 C8 116.57(11) . . ?
O3 C18 C19 119.88(11) . . ?
O3 C18 C17 121.99(11) . . ?
C17 C18 C19 118.10(10) . . ?
H9A C9 H9B 107.7 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C10 C9 C8 113.67(10) . . ?
C5 C8 C9 112.39(9) . . ?
C5 C8 H8 108.0 . . ?
C13 C8 C5 108.89(9) . . ?
C13 C8 C9 111.43(10) . . ?
C13 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C5 C3 C4 123.41(12) . . ?
C2 C3 C5 117.52(12) . . ?
C2 C3 C4 119.07(12) . . ?
O2 C28 C29 122.25(11) . . ?
O2 C28 C27 118.51(11) . . ?
C27 C28 C29 119.24(12) . . ?
O4 C7 C6 123.25(11) . . ?
O4 C7 C1 117.74(11) . . ?
C1 C7 C6 119.00(12) . . ?
C20 C21 C22 113.51(13) . . ?
C23 C21 C20 125.01(13) . . ?
C23 C21 C22 121.46(14) . . ?
C9 C10 C11 110.7(9) . . ?
C12 C10 C9 124.2(12) . . ?
C12 C10 C11 125.1(14) . . ?
C11A C10 C9 123.4(5) . . ?
C11A C10 C12A 119.3(6) . . ?
C12A C10 C9 117.2(5) . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C18 C17 C16 115.14(13) . . ?
H17A C17 H17B 107.5 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C25 C26 H26 118.7 . . ?
C27 C26 C25 122.58(12) . . ?
C27 C26 H26 118.7 . . ?
C3 C2 H2 118.7 . . ?
C1 C2 C3 122.58(12) . . ?
C1 C2 H2 118.7 . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 C1 H1 120.1 . . ?
C2 C1 C7 119.71(12) . . ?
C2 C1 H1 120.1 . . ?
C28 C27 H27 120.2 . . ?
C26 C27 C28 119.52(12) . . ?
C26 C27 H27 120.2 . . ?
C13 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
C13 C14 C15 115.42(14) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C21 C23 H23A 120.0 . . ?
C21 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C10 C12 H12A 120.0 . . ?
C10 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C10 C11A H11D 120.0 . . ?
C10 C11A H11E 120.0 . . ?
H11D C11A H11E 120.0 . . ?
C10 C12A H12C 109.5 . . ?
C10 C12A H12D 109.5 . . ?
C10 C12A H12E 109.5 . . ?
H12C C12A H12D 109.5 . . ?
H12C C12A H12E 109.5 . . ?
H12D C12A H12E 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
O4 C7 C1 C2 -177.80(14) . . . . ?
O3 C18 C17 C16 -8.4(2) . . . . ?
O2 C28 C27 C26 -178.60(14) . . . . ?
O1 C13 C8 C5 -101.88(13) . . . . ?
O1 C13 C8 C9 22.64(15) . . . . ?
O1 C13 C14 C15 6.7(2) . . . . ?
C24 C29 C28 O2 178.94(12) . . . . ?
C24 C29 C28 C27 -0.51(19) . . . . ?
C24 C19 C20 C21 -61.00(14) . . . . ?
C24 C19 C18 O3 -106.00(13) . . . . ?
C24 C19 C18 C17 71.99(13) . . . . ?
C24 C25 C26 C27 -0.9(2) . . . . ?
C5 C6 C7 O4 179.65(12) . . . . ?
C5 C6 C7 C1 -0.3(2) . . . . ?
C5 C3 C2 C1 -0.6(2) . . . . ?
C29 C24 C19 C20 -48.50(14) . . . . ?
C29 C24 C19 C18 73.57(13) . . . . ?
C29 C24 C25 C26 1.25(18) . . . . ?
C29 C24 C25 C30 -178.80(12) . . . . ?
C29 C28 C27 C26 0.9(2) . . . . ?
C6 C5 C8 C13 65.35(13) . . . . ?
C6 C5 C8 C9 -58.61(14) . . . . ?
C6 C5 C3 C2 2.45(18) . . . . ?
C6 C5 C3 C4 -177.10(13) . . . . ?
C6 C7 C1 C2 2.1(2) . . . . ?
C19 C24 C29 C28 -178.57(11) . . . . ?
C19 C24 C25 C26 179.14(12) . . . . ?
C19 C24 C25 C30 -0.91(19) . . . . ?
C19 C20 C21 C23 -12.6(2) . . . . ?
C19 C20 C21 C22 169.27(14) . . . . ?
C19 C18 C17 C16 173.67(13) . . . . ?
C25 C24 C29 C28 -0.57(18) . . . . ?
C25 C24 C19 C20 133.56(12) . . . . ?
C25 C24 C19 C18 -104.37(12) . . . . ?
C25 C26 C27 C28 -0.2(2) . . . . ?
C20 C19 C18 O3 18.72(15) . . . . ?
C20 C19 C18 C17 -163.29(11) . . . . ?
C18 C19 C20 C21 178.38(10) . . . . ?
C8 C5 C6 C7 176.89(11) . . . . ?
C8 C5 C3 C2 -176.44(12) . . . . ?
C8 C5 C3 C4 4.0(2) . . . . ?
C8 C13 C14 C15 -173.34(13) . . . . ?
C8 C9 C10 C12 -71.2(15) . . . . ?
C8 C9 C10 C11 109.8(11) . . . . ?
C8 C9 C10 C11A 117.3(6) . . . . ?
C8 C9 C10 C12A -64.3(6) . . . . ?
C3 C5 C6 C7 -2.05(19) . . . . ?
C3 C5 C8 C13 -115.74(12) . . . . ?
C3 C5 C8 C9 120.30(12) . . . . ?
C3 C2 C1 C7 -1.7(2) . . . . ?
C10 C9 C8 C5 -61.40(13) . . . . ?
C10 C9 C8 C13 176.06(10) . . . . ?
C30 C25 C26 C27 179.15(14) . . . . ?
C14 C13 C8 C5 78.13(13) . . . . ?
C14 C13 C8 C9 -157.34(11) . . . . ?
C4 C3 C2 C1 178.96(15) . . . . ?

_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 7.383
_oxdiff_exptl_absorpt_empirical_full_min 0.622
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_128
_database_code_depnum_ccdc_archive 'CCDC 2047491'
loop_
_audit_author_name
_audit_author_address
'Feijie Song'
;Sichuan Normal University
China
;
_audit_update_record             
;
2020-12-01 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_audit_creation_date             2020-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.5707(3)
_cell_length_b                   7.84870(10)
_cell_length_c                   15.3888(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.1310(10)
_cell_angle_gamma                90
_cell_volume                     2850.86(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20101
_cell_measurement_temperature    294.09(10)
_cell_measurement_theta_max      76.3060
_cell_measurement_theta_min      2.9660
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.770
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26256
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.103
_diffrn_reflns_theta_min         5.987
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.09(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00   5.00   0.50    0.05    --  -46.37 105.00 126.00  178
  2  ω     -1.00  84.00   0.50    0.05    --   46.37-105.00  25.00  170
  3  ω   -175.00 -81.00   0.50    0.10    -- -102.00-105.00  25.00  188
  4  ω   -111.00 -29.00   0.50    0.10    -- -102.00 105.00 126.00  164
  5  ω     33.00 111.00   0.50    0.10    --  106.06-105.00  25.00  156
  6  ω     86.00 178.00   0.50    0.10    --  106.06 105.00 126.00  184
  7  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00  90.00   94
  8  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00-180.00   94
  9  ω    -27.00  44.00   0.50    0.05    --   46.37 -37.00 -90.00  142
 10  ω   -175.00 -81.00   0.50    0.10    -- -102.00 -94.00 150.00  188
 11  ω    -69.00 -29.00   0.50    0.10    -- -102.00  61.00-150.00   80
 12  ω    -69.00 -29.00   0.50    0.10    -- -102.00  61.00 -30.00   80
 13  ω    -69.00 -29.00   0.50    0.10    -- -102.00  61.00 120.00   80
 14  ω    -69.00 -29.00   0.50    0.10    -- -102.00  61.00 -60.00   80
 15  ω    -69.00 -29.00   0.50    0.10    -- -102.00  61.00 -90.00   80
 16  ω     33.00 108.00   0.50    0.10    --  106.06 -77.00-180.00  150
 17  ω     33.00 117.00   0.50    0.10    --  106.06-125.00   0.00  168
 18  ω     33.00  73.00   0.50    0.10    --  106.06 -61.00  30.00   80
 19  ω     33.00  73.00   0.50    0.10    --  106.06 -61.00 -90.00   80
 20  ω     92.00 178.00   0.50    0.10    --  106.06  45.00  90.00  172
 21  ω     23.00 118.00   0.50    0.05    --   46.37  77.00  30.00  190
 22  ω     30.00 118.00   0.50    0.05    --   46.37  57.00 120.00  176
 23  ω     23.00 118.00   0.50    0.05    --   46.37  77.00-180.00  190
 24  ω     23.00 118.00   0.50    0.05    --   46.37  77.00 -90.00  190
 25  ω   -174.00 -87.00   0.50    0.10    -- -102.00 -45.00 120.00  174
 26  ω   -174.00 -87.00   0.50    0.10    -- -102.00 -45.00 -60.00  174
 27  ω   -175.00 -86.00   0.50    0.10    -- -102.00 -30.00-120.00  178
 28  ω   -174.00 -87.00   0.50    0.10    -- -102.00 -45.00-150.00  174
 29  ω   -174.00 -87.00   0.50    0.10    -- -102.00 -45.00  60.00  174
 30  ω   -175.00 -86.00   0.50    0.10    -- -102.00 -30.00 150.00  178
 31  ω    -69.00 -29.00   0.50    0.10    -- -102.00  61.00 150.00   80
 32  ω   -175.00 -86.00   0.50    0.10    -- -102.00 -30.00 -30.00  178
 33  ω   -174.00 -87.00   0.50    0.10    -- -102.00 -45.00  30.00  174
 34  ω   -175.00 -78.00   0.50    0.10    -- -102.00 -77.00 -90.00  194
 35  ω     33.00  73.00   0.50    0.10    --  106.06 -61.00   0.00   80
 36  ω     91.00 178.00   0.50    0.10    --  106.06  30.00  30.00  174
 37  ω     23.00 118.00   0.50    0.05    --   46.37  77.00-150.00  190
 38  ω     23.00  76.50   0.50    0.05    --   46.37  77.00 120.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0392639000
_diffrn_orient_matrix_UB_12      -0.0377319000
_diffrn_orient_matrix_UB_13      0.0950535000
_diffrn_orient_matrix_UB_21      0.0060506000
_diffrn_orient_matrix_UB_22      -0.1859067000
_diffrn_orient_matrix_UB_23      -0.0280246000
_diffrn_orient_matrix_UB_31      0.0517653000
_diffrn_orient_matrix_UB_32      0.0503679000
_diffrn_orient_matrix_UB_33      -0.0323329000
_diffrn_oxdiff_digest_frames     
;
011e2e32ab0458dddad1632bead4fb2a5300110db3b
;
_diffrn_oxdiff_digest_hkl        
;
01381adf5da53d0035aaec35b948cad55a9bea
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2715
_reflns_number_total             2893
_reflns_odcompleteness_completeness 99.24
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.8140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1406
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C12(H12)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.52087(4) 0.45928(13) 0.40508(6) 0.0625(3) Uani 1 1 d . . . . .
O2 O 0.58626(4) 0.33744(15) 0.10168(6) 0.0660(3) Uani 1 1 d . . . . .
H2 H 0.5533 0.3610 0.0988 0.099 Uiso 1 1 calc GR . . . .
C9 C 0.63549(5) 0.48510(14) 0.33654(7) 0.0437(3) Uani 1 1 d . . . . .
C10 C 0.59937(5) 0.45258(15) 0.25134(8) 0.0467(3) Uani 1 1 d . . . . .
H10 H 0.5613 0.4820 0.2382 0.056 Uiso 1 1 calc R . . . .
C4 C 0.61225(5) 0.56489(15) 0.40935(7) 0.0461(3) Uani 1 1 d . . . . .
H4 H 0.6440 0.5824 0.4634 0.055 Uiso 1 1 calc R . . . .
C11 C 0.62007(5) 0.37611(16) 0.18569(8) 0.0481(3) Uani 1 1 d . . . . .
C3 C 0.57153(5) 0.43911(15) 0.43318(7) 0.0465(3) Uani 1 1 d . . . . .
C14 C 0.69215(5) 0.44023(16) 0.35485(9) 0.0523(3) Uani 1 1 d . . . . .
H14 H 0.7164 0.4607 0.4121 0.063 Uiso 1 1 calc R . . . .
C12 C 0.67700(5) 0.33406(16) 0.20458(9) 0.0537(3) Uani 1 1 d . . . . .
H12 H 0.6908 0.2846 0.1600 0.064 Uiso 1 1 calc R . . . .
C5 C 0.58341(6) 0.73715(16) 0.38204(9) 0.0545(3) Uani 1 1 d . . . . .
H5A H 0.5508 0.7200 0.3303 0.065 Uiso 1 1 calc R . . . .
H5B H 0.5696 0.7786 0.4314 0.065 Uiso 1 1 calc R . . . .
C13 C 0.71339(5) 0.36518(17) 0.28915(10) 0.0562(3) Uani 1 1 d . . . . .
C2 C 0.59711(7) 0.29120(19) 0.49170(11) 0.0691(4) Uani 1 1 d . . . . .
H2A H 0.6216 0.2304 0.4625 0.083 Uiso 1 1 calc R . . . .
H2B H 0.6208 0.3352 0.5486 0.083 Uiso 1 1 calc R . . . .
C6 C 0.62032(7) 0.87185(18) 0.35864(12) 0.0698(4) Uani 1 1 d . . . . .
C15 C 0.77535(6) 0.3182(3) 0.31044(15) 0.0918(6) Uani 1 1 d . . . . .
H15A H 0.7978 0.4056 0.3472 0.138 Uiso 1 1 calc GR . . . .
H15B H 0.7859 0.3072 0.2551 0.138 Uiso 1 1 calc GR . . . .
H15C H 0.7817 0.2119 0.3425 0.138 Uiso 1 1 calc GR . . . .
C1 C 0.55644(9) 0.1672(3) 0.51198(16) 0.0973(6) Uani 1 1 d . . . . .
H1A H 0.5324 0.1228 0.4564 0.146 Uiso 1 1 calc GR . . . .
H1B H 0.5337 0.2234 0.5449 0.146 Uiso 1 1 calc GR . . . .
H1C H 0.5770 0.0754 0.5477 0.146 Uiso 1 1 calc GR . . . .
C7 C 0.67543(9) 0.9060(3) 0.42203(19) 0.1075(7) Uani 1 1 d . . . . .
H7A H 0.6709 0.9254 0.4812 0.161 Uiso 1 1 calc GR . . . .
H7B H 0.6918 1.0052 0.4028 0.161 Uiso 1 1 calc GR . . . .
H7C H 0.6999 0.8099 0.4239 0.161 Uiso 1 1 calc GR . . . .
C8 C 0.60133(16) 0.9590(3) 0.2817(2) 0.1177(9) Uani 1 1 d . . . . .
H8A H 0.6236(13) 1.042(4) 0.272(2) 0.155(11) Uiso 1 1 d . . . . .
H8B H 0.5617(14) 0.959(4) 0.248(2) 0.155(13) Uiso 1 1 d . . . . .


_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 1.2092(14) . ?
O2 H2 0.8200 . ?
O2 C11 1.3626(14) . ?
C9 C10 1.3877(16) . ?
C9 C4 1.5262(15) . ?
C9 C14 1.3869(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.3875(16) . ?
C4 H4 0.9800 . ?
C4 C3 1.5213(16) . ?
C4 C5 1.5301(17) . ?
C11 C12 1.3872(17) . ?
C3 C2 1.4964(18) . ?
C14 H14 0.9300 . ?
C14 C13 1.3909(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.3807(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5005(19) . ?
C13 C15 1.5112(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.489(2) . ?
C6 C7 1.457(3) . ?
C6 C8 1.334(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.89(3) . ?
C8 H8B 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2 109.5 . . ?
C10 C9 C4 119.84(10) . . ?
C14 C9 C10 119.19(11) . . ?
C14 C9 C4 120.95(10) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.99(10) . . ?
C11 C10 H10 120.0 . . ?
C9 C4 H4 108.0 . . ?
C9 C4 C5 113.59(9) . . ?
C3 C4 C9 108.42(9) . . ?
C3 C4 H4 108.0 . . ?
C3 C4 C5 110.74(10) . . ?
C5 C4 H4 108.0 . . ?
O2 C11 C10 122.47(11) . . ?
O2 C11 C12 117.34(10) . . ?
C12 C11 C10 120.18(11) . . ?
O1 C3 C4 120.63(11) . . ?
O1 C3 C2 122.36(12) . . ?
C2 C3 C4 117.01(11) . . ?
C9 C14 H14 119.4 . . ?
C9 C14 C13 121.20(11) . . ?
C13 C14 H14 119.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.44(11) . . ?
C13 C12 H12 119.8 . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 115.08(11) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C14 C13 C15 120.31(13) . . ?
C12 C13 C14 118.98(11) . . ?
C12 C13 C15 120.71(13) . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C1 C2 C3 116.05(14) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C7 C6 C5 118.70(15) . . ?
C8 C6 C5 119.2(2) . . ?
C8 C6 C7 122.0(2) . . ?
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 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 117(2) . . ?
C6 C8 H8B 122(2) . . ?
H8A C8 H8B 119(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 C3 C2 C1 1.3(2) . . . . ?
O2 C11 C12 C13 -178.17(12) . . . . ?
C9 C10 C11 O2 178.34(11) . . . . ?
C9 C10 C11 C12 -0.86(18) . . . . ?
C9 C4 C3 O1 -103.33(12) . . . . ?
C9 C4 C3 C2 76.29(13) . . . . ?
C9 C4 C5 C6 -58.72(15) . . . . ?
C9 C14 C13 C12 -0.5(2) . . . . ?
C9 C14 C13 C15 179.67(15) . . . . ?
C10 C9 C4 C3 65.62(13) . . . . ?
C10 C9 C4 C5 -57.93(14) . . . . ?
C10 C9 C14 C13 0.71(19) . . . . ?
C10 C11 C12 C13 1.07(19) . . . . ?
C4 C9 C10 C11 -178.38(10) . . . . ?
C4 C9 C14 C13 179.05(11) . . . . ?
C4 C3 C2 C1 -178.33(14) . . . . ?
C4 C5 C6 C7 -51.16(19) . . . . ?
C4 C5 C6 C8 130.29(19) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C11 C12 C13 C15 179.43(14) . . . . ?
C3 C4 C5 C6 179.00(11) . . . . ?
C14 C9 C10 C11 -0.02(18) . . . . ?
C14 C9 C4 C3 -112.71(12) . . . . ?
C14 C9 C4 C5 123.74(12) . . . . ?
C5 C4 C3 O1 21.92(15) . . . . ?
C5 C4 C3 C2 -158.46(11) . . . . ?

_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 1.979
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_127
_database_code_depnum_ccdc_archive 'CCDC 2047493'
loop_
_audit_author_name
_audit_author_address
'Feijie Song'
;Sichuan Normal University
China
;
_audit_update_record             
;
2020-12-01 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_audit_creation_date             2020-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1'
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                   7.35280(10)
_cell_length_b                   7.36750(10)
_cell_length_c                   24.5337(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1329.03(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9746
_cell_measurement_temperature    293.74(10)
_cell_measurement_theta_max      76.1280
_cell_measurement_theta_min      3.6140
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12440
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_min         3.603
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.74(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  81.00   0.50    0.05    --   46.37-100.00 116.00  202
  2  ω     33.00 109.00   0.50    0.05    --  106.06-100.00 116.00  152
  3  ω     92.00 178.00   0.50    0.05    --  106.06  41.00 123.00  172
  4  ω    -24.00  29.00   0.50    0.05    --  -46.37  19.00-120.00  106
  5  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -30.00   80
  6  ω     33.00 109.00   0.50    0.05    --  106.06 -94.00   0.00  152
  7  ω     33.00 108.00   0.50    0.05    --  106.06 -77.00-150.00  150
  8  ω     33.00  73.00   0.50    0.05    --  106.06 -61.00-180.00   80
  9  ω     30.00 118.00   0.50    0.05    --   46.37  57.00  90.00  176
 10  ω     23.00 118.00   0.50    0.05    --   46.37  77.00-150.00  190
 11  ω   -175.00 -84.00   0.50    0.05    -- -102.00 -15.00 -30.00  182
 12  ω   -175.00 -84.00   0.50    0.05    -- -102.00 -15.00-120.00  182
 13  ω   -175.00 -77.00   0.50    0.05    -- -102.00 -90.00-149.00  196
 14  ω     91.00 178.00   0.50    0.05    --  106.06  30.00  60.00  174
 15  ω     23.00 118.00   0.50    0.05    --   46.37  77.00 -30.00  190
 16  ω     30.00 118.00   0.50    0.05    --   46.37  57.00 150.00  176
 17  ω   -175.00-150.00   0.50    0.05    -- -102.00 -77.00  60.00   50
 18  ω   -174.00 -87.00   0.50    0.05    -- -102.00 -45.00 -60.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1944867000
_diffrn_orient_matrix_UB_12      -0.0109136000
_diffrn_orient_matrix_UB_13      0.0231630000
_diffrn_orient_matrix_UB_21      -0.0413971000
_diffrn_orient_matrix_UB_22      -0.1898748000
_diffrn_orient_matrix_UB_23      0.0231702000
_diffrn_orient_matrix_UB_31      0.0662472000
_diffrn_orient_matrix_UB_32      -0.0868707000
_diffrn_orient_matrix_UB_33      -0.0535505000
_diffrn_oxdiff_digest_frames     
;
0102d9e23d7451df37b77dcc289eda6d8700102090c
;
_diffrn_oxdiff_digest_hkl        
;
01678c9e945d05bb2572b1cedb8fbb3fe81f9c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                2418
_reflns_number_total             2657
_reflns_odcompleteness_completeness 99.37
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+0.0760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C4(H4), C3(H3), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O2 O 0.5039(2) 0.2769(3) 0.29224(8) 0.0822(6) Uani 1 1 d . . . . .
H2 H 0.5284 0.2239 0.2638 0.123 Uiso 1 1 calc GR . . . .
O1 O 0.4290(4) 0.6795(3) 0.31190(7) 0.1024(8) Uani 1 1 d . . . . .
C8 C 0.4104(3) 0.4322(3) 0.43609(8) 0.0502(4) Uani 1 1 d . . . . .
H8 H 0.3532 0.3308 0.4213 0.060 Uiso 1 1 calc R . . . .
C10 C 0.2474(3) 0.4217(3) 0.32880(7) 0.0491(5) Uani 1 1 d . . . . .
C7 C 0.4345(3) 0.5838(3) 0.40328(8) 0.0496(5) Uani 1 1 d . . . . .
C15 C 0.3201(3) 0.2776(3) 0.29972(8) 0.0570(5) Uani 1 1 d . . . . .
C9 C 0.3737(3) 0.5724(3) 0.34558(8) 0.0579(5) Uani 1 1 d . . . . .
C11 C 0.0613(3) 0.4301(3) 0.33936(8) 0.0553(5) Uani 1 1 d . . . . .
C5 C 0.5203(3) 0.7397(3) 0.42481(11) 0.0615(6) Uani 1 1 d . . . . .
C2 C 0.4678(3) 0.4253(3) 0.48987(9) 0.0579(5) Uani 1 1 d . . . . .
C14 C 0.2099(4) 0.1388(4) 0.28156(10) 0.0713(7) Uani 1 1 d . . . . .
H14 H 0.2589 0.0417 0.2623 0.086 Uiso 1 1 calc R . . . .
C4 C 0.5761(4) 0.7302(4) 0.47889(11) 0.0721(7) Uani 1 1 d . . . . .
H4 H 0.6322 0.8310 0.4943 0.086 Uiso 1 1 calc R . . . .
C3 C 0.5521(4) 0.5793(4) 0.51036(10) 0.0703(7) Uani 1 1 d . . . . .
H3 H 0.5931 0.5798 0.5462 0.084 Uiso 1 1 calc R . . . .
C12 C -0.0481(3) 0.2899(4) 0.32084(10) 0.0704(7) Uani 1 1 d . . . . .
H12 H -0.1725 0.2926 0.3276 0.084 Uiso 1 1 calc R . . . .
C13 C 0.0265(4) 0.1458(4) 0.29228(11) 0.0761(7) Uani 1 1 d . . . . .
H13 H -0.0485 0.0525 0.2802 0.091 Uiso 1 1 calc R . . . .
C1 C 0.4392(4) 0.2595(4) 0.52444(10) 0.0773(7) Uani 1 1 d . . . . .
H1A H 0.3128 0.2492 0.5337 0.116 Uiso 1 1 calc GR . . . .
H1B H 0.5100 0.2697 0.5572 0.116 Uiso 1 1 calc GR . . . .
H1C H 0.4766 0.1537 0.5046 0.116 Uiso 1 1 calc GR . . . .
C6 C 0.5500(5) 0.9122(4) 0.39311(14) 0.0890(9) Uani 1 1 d . . . . .
H6A H 0.6324 0.8893 0.3635 0.134 Uiso 1 1 calc GR . . . .
H6B H 0.6005 1.0031 0.4167 0.134 Uiso 1 1 calc GR . . . .
H6C H 0.4359 0.9542 0.3789 0.134 Uiso 1 1 calc GR . . . .
C16 C -0.0205(4) 0.5911(4) 0.36797(12) 0.0828(8) Uani 1 1 d . . . . .
H16A H 0.0466 0.6156 0.4007 0.124 Uiso 1 1 calc GR . . . .
H16B H -0.1449 0.5654 0.3770 0.124 Uiso 1 1 calc GR . . . .
H16C H -0.0154 0.6951 0.3444 0.124 Uiso 1 1 calc GR . . . .


_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
O2 H2 0.8200 . ?
O2 C15 1.364(3) . ?
O1 C9 1.213(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.388(3) . ?
C8 C2 1.386(3) . ?
C10 C15 1.386(3) . ?
C10 C9 1.505(3) . ?
C10 C11 1.394(3) . ?
C7 C9 1.487(3) . ?
C7 C5 1.413(3) . ?
C15 C14 1.379(4) . ?
C11 C12 1.386(4) . ?
C11 C16 1.504(4) . ?
C5 C4 1.391(4) . ?
C5 C6 1.506(4) . ?
C2 C3 1.387(4) . ?
C2 C1 1.502(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.365(4) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C15 O2 H2 109.5 . . ?
C7 C8 H8 118.6 . . ?
C2 C8 H8 118.6 . . ?
C2 C8 C7 122.8(2) . . ?
C15 C10 C9 117.91(18) . . ?
C15 C10 C11 120.5(2) . . ?
C11 C10 C9 121.5(2) . . ?
C8 C7 C9 117.91(18) . . ?
C8 C7 C5 119.64(19) . . ?
C5 C7 C9 122.41(19) . . ?
O2 C15 C10 117.0(2) . . ?
O2 C15 C14 122.4(2) . . ?
C14 C15 C10 120.5(2) . . ?
O1 C9 C10 120.0(2) . . ?
O1 C9 C7 120.7(2) . . ?
C7 C9 C10 119.18(17) . . ?
C10 C11 C16 121.0(2) . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 C16 120.6(2) . . ?
C7 C5 C6 123.9(2) . . ?
C4 C5 C7 116.6(2) . . ?
C4 C5 C6 119.5(2) . . ?
C8 C2 C3 116.8(2) . . ?
C8 C2 C1 121.7(2) . . ?
C3 C2 C1 121.5(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H14 120.4 . . ?
C5 C4 H4 118.6 . . ?
C3 C4 C5 122.9(2) . . ?
C3 C4 H4 118.6 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O2 C15 C14 C13 177.7(3) . . . . ?
C8 C7 C9 O1 -162.0(2) . . . . ?
C8 C7 C9 C10 15.8(3) . . . . ?
C8 C7 C5 C4 0.0(3) . . . . ?
C8 C7 C5 C6 -178.8(2) . . . . ?
C8 C2 C3 C4 0.3(4) . . . . ?
C10 C15 C14 C13 0.5(4) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C7 C8 C2 C3 0.1(3) . . . . ?
C7 C8 C2 C1 179.8(2) . . . . ?
C7 C5 C4 C3 0.5(4) . . . . ?
C15 C10 C9 O1 73.6(3) . . . . ?
C15 C10 C9 C7 -104.2(2) . . . . ?
C15 C10 C11 C12 1.0(3) . . . . ?
C15 C10 C11 C16 -176.3(2) . . . . ?
C15 C14 C13 C12 0.1(4) . . . . ?
C9 C10 C15 O2 5.0(3) . . . . ?
C9 C10 C15 C14 -177.7(2) . . . . ?
C9 C10 C11 C12 177.44(19) . . . . ?
C9 C10 C11 C16 0.1(3) . . . . ?
C9 C7 C5 C4 -177.8(2) . . . . ?
C9 C7 C5 C6 3.4(3) . . . . ?
C11 C10 C15 O2 -178.4(2) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C11 C10 C9 O1 -103.0(3) . . . . ?
C11 C10 C9 C7 79.3(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C5 C7 C9 O1 15.9(4) . . . . ?
C5 C7 C9 C10 -166.37(19) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C2 C8 C7 C9 177.6(2) . . . . ?
C2 C8 C7 C5 -0.3(3) . . . . ?
C1 C2 C3 C4 -179.4(3) . . . . ?
C6 C5 C4 C3 179.3(3) . . . . ?
C16 C11 C12 C13 177.0(2) . . . . ?

_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 1.927
_oxdiff_exptl_absorpt_empirical_full_min 0.532
