# 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_fc118-2
_database_code_depnum_ccdc_archive 'CCDC 2116439'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2020-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H38 O2'
_chemical_formula_sum            'C30 H38 O2'
_chemical_formula_weight         430.60
_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           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                   8.8651(4)
_cell_length_b                   21.4359(10)
_cell_length_c                   13.5074(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.681(5)
_cell_angle_gamma                90
_cell_volume                     2431.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2697
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.7790
_cell_measurement_theta_min      3.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81418
_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    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10631
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.430
_diffrn_reflns_theta_min         4.024
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  63.00   1.00    1.09    --   40.98-125.00-180.00   27
  2  ω     58.00 170.00   1.00    1.00    --  106.95  15.00-180.00  112
  3  ω     84.00 110.00   1.00    1.00    --  106.95  30.00 -30.00   26
  4  ω     26.00 100.00   1.00    1.00    --  106.95 -95.00  60.00   74
  5  ω     71.00 124.00   1.00    1.00    --  106.95 -30.00 150.00   53
  6  ω    -99.00  24.00   1.00    1.09    --  -40.98   0.00   0.00  123
  7  ω     22.00  50.00   1.00    1.09    --   41.23 -99.00   0.00   28
  8  ω     28.00  96.00   1.00    1.09    --   41.23-125.00 -90.00   68
  9  ω     34.00 118.00   1.00    1.00    --  106.95-125.00 -90.00   84
 10  ω    105.00 130.00   1.00    1.00    --  106.95 -61.00  60.00   25
 11  ω     96.00 121.00   1.00    1.00    --  106.95-125.00  90.00   25
 12  ω     34.00  60.00   1.00    1.00    --  106.95-125.00  90.00   26
 13  ω     35.00  75.00   1.00    1.00    --  106.95 -61.00  60.00   40
 14  ω     66.00  91.00   1.00    1.00    --  106.95 -61.00-150.00   25
;
_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      0.0168182000
_diffrn_orient_matrix_UB_12      -0.0653376000
_diffrn_orient_matrix_UB_13      -0.0429346000
_diffrn_orient_matrix_UB_21      -0.0421223000
_diffrn_orient_matrix_UB_22      -0.0299607000
_diffrn_orient_matrix_UB_23      0.0914182000
_diffrn_orient_matrix_UB_31      -0.1776911000
_diffrn_orient_matrix_UB_32      0.0009063000
_diffrn_orient_matrix_UB_33      -0.0655722000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3561
_reflns_number_total             4768
_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 1.171.38.43f (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 (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         0.306
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00048(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.036
_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)+(0.0555P)²+0.4153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1334
_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
2.a Ternary CH refined with riding coordinates:
 C16(H16), C2(H2), C1(H1), C5(H5), C17(H17), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B), C9(H9A,H9B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C30(H30A,H30B,
 H30C), C13(H13A,H13B,H13C), C28(H28A,H28B,H28C)
;
_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 0.80434(15) 0.91514(6) 0.80616(11) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.66645(16) 0.42827(7) 0.60693(12) 0.0345(4) Uani 1 1 d . . . . .
C7 C 0.73515(19) 0.82461(8) 0.68890(14) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.42811(19) 0.73084(8) 0.58876(14) 0.0194(4) Uani 1 1 d . . . . .
C16 C 0.76796(19) 0.58304(8) 0.66892(14) 0.0174(4) Uani 1 1 d . . . . .
H16 H 0.683348 0.588678 0.601978 0.021 Uiso 1 1 calc R . . . .
C2 C 0.71675(19) 0.70203(8) 0.67043(13) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.785706 0.710176 0.627843 0.020 Uiso 1 1 calc R . . . .
C8 C 0.7309(2) 0.86691(9) 0.77857(14) 0.0201(4) Uani 1 1 d . . . . .
C10 C 0.5681(2) 0.77610(8) 0.76437(14) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.72332(19) 0.75991(8) 0.73952(13) 0.0166(4) Uani 1 1 d . . . . .
H1 H 0.811667 0.755529 0.804972 0.020 Uiso 1 1 calc R . . . .
C6 C 0.56431(19) 0.83443(8) 0.61053(14) 0.0194(4) Uani 1 1 d . . . . .
H6A H 0.530978 0.877538 0.610453 0.023 Uiso 1 1 calc R . . . .
H6B H 0.559516 0.822819 0.540181 0.023 Uiso 1 1 calc R . . . .
C25 C 0.92291(19) 0.56188(8) 0.64920(14) 0.0194(4) Uani 1 1 d . . . . .
C5 C 0.45927(19) 0.79066(8) 0.65235(14) 0.0188(4) Uani 1 1 d . . . . .
H5 H 0.360088 0.810972 0.652039 0.023 Uiso 1 1 calc R . . . .
C11 C 0.8740(2) 0.83607(9) 0.65016(15) 0.0231(4) Uani 1 1 d . . . . .
C17 C 0.78078(19) 0.64192(8) 0.73677(13) 0.0170(4) Uani 1 1 d . . . . .
H17 H 0.711976 0.634883 0.779834 0.020 Uiso 1 1 calc R . . . .
C18 C 0.9494(2) 0.64922(8) 0.81186(14) 0.0209(4) Uani 1 1 d . . . . .
H18 H 0.974888 0.685667 0.851031 0.025 Uiso 1 1 calc R . . . .
C3 C 0.54925(19) 0.69257(8) 0.59664(13) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.529802 0.657517 0.553831 0.022 Uiso 1 1 calc R . . . .
C19 C 1.0621(2) 0.60625(9) 0.82443(14) 0.0204(4) Uani 1 1 d . . . . .
C22 C 0.7412(2) 0.52060(8) 0.72045(14) 0.0205(4) Uani 1 1 d . . . . .
C24 C 0.8693(2) 0.50056(9) 0.58923(15) 0.0242(4) Uani 1 1 d . . . . .
H24A H 0.823693 0.508164 0.514782 0.029 Uiso 1 1 calc R . . . .
H24B H 0.957849 0.471813 0.601174 0.029 Uiso 1 1 calc R . . . .
C20 C 1.02352(19) 0.54651(8) 0.76257(14) 0.0203(4) Uani 1 1 d . . . . .
H20 H 1.119694 0.522920 0.765855 0.024 Uiso 1 1 calc R . . . .
C9 C 0.6152(2) 0.83718(9) 0.82589(14) 0.0228(4) Uani 1 1 d . . . . .
H9A H 0.523021 0.863645 0.816944 0.027 Uiso 1 1 calc R . . . .
H9B H 0.665649 0.829023 0.899789 0.027 Uiso 1 1 calc R . . . .
C29 C 0.9990(2) 0.60694(9) 0.59237(15) 0.0245(4) Uani 1 1 d . . . . .
H29A H 0.926706 0.614747 0.523528 0.037 Uiso 1 1 calc GR . . . .
H29B H 1.095521 0.589083 0.587212 0.037 Uiso 1 1 calc GR . . . .
H29C H 1.022876 0.645466 0.630452 0.037 Uiso 1 1 calc GR . . . .
C26 C 0.5965(2) 0.51633(9) 0.75457(16) 0.0258(4) Uani 1 1 d . . . . .
C23 C 0.7452(2) 0.47522(9) 0.63385(15) 0.0246(4) Uani 1 1 d . . . . .
C21 C 0.9075(2) 0.50782(9) 0.80316(15) 0.0236(4) Uani 1 1 d . . . . .
H21A H 0.910113 0.521739 0.872021 0.028 Uiso 1 1 calc R . . . .
H21B H 0.933633 0.463767 0.806258 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2629(2) 0.71827(9) 0.51691(17) 0.0281(4) Uani 1 1 d . . . . .
H15A H 0.189408 0.719622 0.555872 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.259349 0.677765 0.485919 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.234113 0.749367 0.462950 0.042 Uiso 1 1 calc GR . . . .
C14 C 0.5030(2) 0.72798(9) 0.82288(15) 0.0275(4) Uani 1 1 d . . . . .
H14A H 0.471486 0.691263 0.780578 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.412527 0.745000 0.837852 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.583969 0.717296 0.887124 0.041 Uiso 1 1 calc GR . . . .
C30 C 1.2267(2) 0.61147(10) 0.90136(17) 0.0317(5) Uani 1 1 d . . . . .
H30A H 1.235064 0.649193 0.941058 0.048 Uiso 1 1 calc GR . . . .
H30B H 1.303087 0.612275 0.864534 0.048 Uiso 1 1 calc GR . . . .
H30C H 1.247403 0.576265 0.947725 0.048 Uiso 1 1 calc GR . . . .
C13 C 1.0346(2) 0.81907(10) 0.72583(19) 0.0342(5) Uani 1 1 d . . . . .
H13A H 1.048351 0.839007 0.791785 0.051 Uiso 1 1 calc GR . . . .
H13B H 1.116637 0.832733 0.698584 0.051 Uiso 1 1 calc GR . . . .
H13C H 1.041070 0.774654 0.735303 0.051 Uiso 1 1 calc GR . . . .
C12 C 0.8592(3) 0.86153(11) 0.55866(17) 0.0356(5) Uani 1 1 d . . . . .
C28 C 0.4420(2) 0.53222(11) 0.67244(18) 0.0355(5) Uani 1 1 d . . . . .
H28A H 0.437320 0.576341 0.659660 0.053 Uiso 1 1 calc GR . . . .
H28B H 0.355010 0.520094 0.696055 0.053 Uiso 1 1 calc GR . . . .
H28C H 0.434775 0.510378 0.609031 0.053 Uiso 1 1 calc GR . . . .
C27 C 0.6011(3) 0.50046(12) 0.8499(2) 0.0404(6) Uani 1 1 d . . . . .
H12A H 0.955(3) 0.8690(12) 0.540(2) 0.051(7) Uiso 1 1 d . . . . .
H12B H 0.752(3) 0.8751(11) 0.5092(18) 0.039(6) Uiso 1 1 d . . . . .
H27A H 0.505(3) 0.4980(13) 0.868(2) 0.053(8) Uiso 1 1 d . . . . .
H27B H 0.705(3) 0.4903(12) 0.905(2) 0.044(7) 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 C8 1.215(2) . ?
O2 C23 1.213(2) . ?
C7 C8 1.523(2) . ?
C7 C1 1.565(2) . ?
C7 C6 1.559(2) . ?
C7 C11 1.504(2) . ?
C4 C5 1.519(2) . ?
C4 C3 1.328(2) . ?
C4 C15 1.500(2) . ?
C16 C25 1.549(2) . ?
C16 C17 1.542(2) . ?
C16 C22 1.561(2) . ?
C2 C1 1.542(2) . ?
C2 C17 1.568(2) . ?
C2 C3 1.514(2) . ?
C8 C9 1.512(3) . ?
C10 C1 1.556(2) . ?
C10 C5 1.543(2) . ?
C10 C9 1.535(3) . ?
C10 C14 1.521(2) . ?
C6 C5 1.550(2) . ?
C25 C24 1.537(3) . ?
C25 C20 1.541(2) . ?
C25 C29 1.520(2) . ?
C11 C13 1.507(3) . ?
C11 C12 1.318(3) . ?
C17 C18 1.522(2) . ?
C18 C19 1.329(2) . ?
C19 C20 1.507(3) . ?
C19 C30 1.500(2) . ?
C22 C26 1.498(2) . ?
C22 C23 1.530(3) . ?
C22 C21 1.562(2) . ?
C24 C23 1.514(3) . ?
C20 C21 1.552(2) . ?
C26 C28 1.500(3) . ?
C26 C27 1.320(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
C8 C7 C1 99.09(14) . . ?
C8 C7 C6 101.15(13) . . ?
C6 C7 C1 103.29(13) . . ?
C11 C7 C8 114.26(15) . . ?
C11 C7 C1 118.28(14) . . ?
C11 C7 C6 117.83(15) . . ?
C3 C4 C5 118.70(15) . . ?
C3 C4 C15 122.54(17) . . ?
C15 C4 C5 118.73(15) . . ?
C25 C16 C22 95.46(13) . . ?
C17 C16 C25 116.19(14) . . ?
C17 C16 C22 115.43(14) . . ?
C1 C2 C17 112.25(14) . . ?
C3 C2 C1 110.19(13) . . ?
C3 C2 C17 111.43(14) . . ?
O1 C8 C7 127.11(17) . . ?
O1 C8 C9 126.74(17) . . ?
C9 C8 C7 106.15(14) . . ?
C5 C10 C1 98.73(13) . . ?
C9 C10 C1 101.59(13) . . ?
C9 C10 C5 109.54(15) . . ?
C14 C10 C1 118.00(15) . . ?
C14 C10 C5 115.12(15) . . ?
C14 C10 C9 112.32(15) . . ?
C2 C1 C7 116.33(14) . . ?
C2 C1 C10 116.43(14) . . ?
C10 C1 C7 94.83(13) . . ?
C5 C6 C7 103.71(13) . . ?
C24 C25 C16 101.51(13) . . ?
C24 C25 C20 108.89(15) . . ?
C20 C25 C16 98.90(13) . . ?
C29 C25 C16 117.55(15) . . ?
C29 C25 C24 112.94(15) . . ?
C29 C25 C20 115.38(14) . . ?
C4 C5 C10 109.09(14) . . ?
C4 C5 C6 109.06(14) . . ?
C10 C5 C6 102.70(13) . . ?
C7 C11 C13 115.15(16) . . ?
C12 C11 C7 123.14(18) . . ?
C12 C11 C13 121.65(18) . . ?
C16 C17 C2 112.86(14) . . ?
C18 C17 C16 110.48(14) . . ?
C18 C17 C2 113.25(14) . . ?
C19 C18 C17 123.47(17) . . ?
C4 C3 C2 124.57(16) . . ?
C18 C19 C20 119.34(16) . . ?
C18 C19 C30 124.17(17) . . ?
C30 C19 C20 116.42(15) . . ?
C16 C22 C21 103.06(13) . . ?
C26 C22 C16 117.16(15) . . ?
C26 C22 C23 115.34(15) . . ?
C26 C22 C21 118.28(16) . . ?
C23 C22 C16 99.22(14) . . ?
C23 C22 C21 100.82(14) . . ?
C23 C24 C25 103.79(14) . . ?
C25 C20 C21 103.13(13) . . ?
C19 C20 C25 109.01(15) . . ?
C19 C20 C21 108.46(15) . . ?
C8 C9 C10 103.55(14) . . ?
C22 C26 C28 115.32(17) . . ?
C27 C26 C22 123.65(19) . . ?
C27 C26 C28 121.03(19) . . ?
O2 C23 C22 127.20(18) . . ?
O2 C23 C24 126.90(18) . . ?
C24 C23 C22 105.90(15) . . ?
C20 C21 C22 103.53(14) . . ?

_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.554
####################################################################### 
# 
# 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_56h-50
_database_code_depnum_ccdc_archive 'CCDC 2116451'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-01-22
_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 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0318(7)
_cell_length_b                   7.2894(8)
_cell_length_c                   14.1595(17)
_cell_angle_alpha                86.853(9)
_cell_angle_beta                 77.465(9)
_cell_angle_gamma                64.902(10)
_cell_volume                     641.02(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3200
_cell_measurement_theta_min      6.7150
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48784
_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    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.13
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4001
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.713
_diffrn_reflns_theta_min         3.200
_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 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -10.00   1.00    1.00    --  -40.73 125.00-180.00   46
  2  ω     92.00 119.00   1.00    1.00    --   40.73 167.00-118.00   27
  3  ω     94.00 138.00   1.00    1.20    --  107.58  77.00 -30.00   44
  4  ω    147.00 174.00   1.00    1.20    --  107.58 125.00  30.00   27
  5  ω     99.00 177.00   1.00    1.20    --  107.58 125.00 150.00   78
  6  ω    100.00 177.00   1.00    1.20    --  107.58 116.00  96.00   77
  7  ω     98.00 147.00   1.00    1.20    --  107.58  45.00 -90.00   49
  8  ω     83.00 178.00   1.00    1.20    --  107.58  45.00-150.00   95
  9  ω     90.00 117.00   1.00    1.20    --  107.58-125.00 -30.00   27
 10  ω     46.00 124.00   1.00    1.20    --  107.58 -30.00  30.00   78
 11  ω     36.00 110.00   1.00    1.20    --  107.58 -95.00  90.00   74
 12  ω     27.00  97.00   1.00    1.00    --   40.73-125.00   0.00   70
 13  ω     35.00 106.00   1.00    1.20    --  107.58 -95.00-180.00   71
 14  ω     37.00 132.00   1.00    1.20    --  107.58 -45.00-180.00   95
 15  ω   -114.00  -5.00   1.00    1.00    --  -40.73 -19.00  90.00  109
 16  ω   -114.00 -39.00   1.00    1.00    --  -40.73 -38.00  30.00   75
;
_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      -0.1193132000
_diffrn_orient_matrix_UB_12      -0.1064323000
_diffrn_orient_matrix_UB_13      0.0689926000
_diffrn_orient_matrix_UB_21      -0.0184610000
_diffrn_orient_matrix_UB_22      0.1320704000
_diffrn_orient_matrix_UB_23      0.0857929000
_diffrn_orient_matrix_UB_31      -0.2162603000
_diffrn_orient_matrix_UB_32      0.1605935000
_diffrn_orient_matrix_UB_33      -0.0180108000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2169
_reflns_number_total             2495
_reflns_odcompleteness_completeness 99.78
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.183
_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)+(0.0790P)²+2.9594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2685
_refine_ls_wR_factor_ref         0.2715
_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:
 C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.0304(5) 0.7911(5) 0.4945(2) 0.0279(8) Uani 1 1 d . . . . .
O3 O 0.2717(5) 0.8316(5) 0.4419(2) 0.0288(8) Uani 1 1 d . . . . .
H3 H 0.190488 0.950146 0.458273 0.043 Uiso 1 1 calc R U . . .
O1 O 0.9376(5) 0.0723(5) 0.3045(3) 0.0357(9) Uani 1 1 d . . . . .
C14 C 0.1616(7) 0.7225(7) 0.4544(3) 0.0231(9) Uani 1 1 d . . . . .
C1 C 0.3685(7) 0.5884(6) 0.2385(3) 0.0219(9) Uani 1 1 d . . . . .
H1 H 0.308369 0.731611 0.259170 0.026 Uiso 1 1 calc R U . . .
C10 C 0.2686(7) 0.4712(6) 0.3130(3) 0.0207(9) Uani 1 1 d . . . . .
C13 C 0.2884(7) 0.5068(6) 0.4172(3) 0.0223(9) Uani 1 1 d . . . . .
H13A H 0.239427 0.420685 0.460728 0.027 Uiso 1 1 calc R U . . .
H13B H 0.438598 0.466859 0.417410 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6140(7) 0.4905(6) 0.2257(3) 0.0234(9) Uani 1 1 d . . . . .
H2A H 0.651051 0.502818 0.286398 0.028 Uiso 1 1 calc R U . . .
H2B H 0.675108 0.561607 0.177546 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5691(7) 0.1106(6) 0.3340(3) 0.0250(10) Uani 1 1 d . . . . .
H5A H 0.529710 0.157868 0.401214 0.030 Uiso 1 1 calc R U . . .
H5B H 0.594631 -0.030867 0.331728 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7656(7) 0.1380(6) 0.2813(3) 0.0248(10) Uani 1 1 d . . . . .
C15 C 0.0309(7) 0.5398(7) 0.3125(3) 0.0248(10) Uani 1 1 d . . . . .
H15A H -0.044077 0.683776 0.324983 0.037 Uiso 1 1 calc R U . . .
H15B H -0.030068 0.472568 0.361826 0.037 Uiso 1 1 calc R U . . .
H15C H 0.017597 0.505956 0.250417 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7121(7) 0.2612(7) 0.1931(3) 0.0243(10) Uani 1 1 d . . . . .
C7 C 0.5245(7) 0.2170(6) 0.1731(3) 0.0237(10) Uani 1 1 d . . . . .
C9 C 0.3226(7) 0.5669(7) 0.1420(3) 0.0266(10) Uani 1 1 d . . . . .
H9 H 0.245600 0.676739 0.108275 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4026(7) 0.3761(7) 0.1096(3) 0.0270(10) Uani 1 1 d . . . . .
H8 H 0.384321 0.342320 0.050849 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3926(7) 0.2388(6) 0.2802(3) 0.0219(9) Uani 1 1 d . . . . .
H6 H 0.289943 0.178943 0.284317 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6024(8) 0.0039(7) 0.1287(4) 0.0310(11) Uani 1 1 d . . . . .
H12A H 0.667739 0.000194 0.061396 0.047 Uiso 1 1 calc R U . . .
H12B H 0.482498 -0.029936 0.134915 0.047 Uiso 1 1 calc R U . . .
H12C H 0.705982 -0.092223 0.161878 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9086(8) 0.2078(8) 0.1102(4) 0.0318(11) Uani 1 1 d . . . . .
H11A H 0.867557 0.288329 0.055938 0.048 Uiso 1 1 calc R U . . .
H11B H 0.966005 0.066695 0.091595 0.048 Uiso 1 1 calc R U . . .
H11C H 1.015757 0.234757 0.130986 0.048 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
O2 C14 1.233(5) . ?
O3 H3 0.8200 . ?
O3 C14 1.308(5) . ?
O1 C4 1.210(6) . ?
C14 C13 1.498(6) . ?
C1 H1 0.9800 . ?
C1 C10 1.558(6) . ?
C1 C2 1.535(6) . ?
C1 C9 1.500(6) . ?
C10 C13 1.557(6) . ?
C10 C15 1.530(6) . ?
C10 C6 1.582(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.566(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.509(6) . ?
C5 C6 1.531(6) . ?
C4 C3 1.517(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 C7 1.567(6) . ?
C3 C11 1.526(6) . ?
C7 C8 1.505(6) . ?
C7 C6 1.574(6) . ?
C7 C12 1.531(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.325(7) . ?
C8 H8 0.9300 . ?
C6 H6 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C14 O3 H3 109.5 . . ?
O2 C14 O3 122.7(4) . . ?
O2 C14 C13 122.7(4) . . ?
O3 C14 C13 114.5(4) . . ?
C10 C1 H1 110.6 . . ?
C2 C1 H1 110.6 . . ?
C2 C1 C10 110.0(3) . . ?
C9 C1 H1 110.6 . . ?
C9 C1 C10 108.2(3) . . ?
C9 C1 C2 106.6(4) . . ?
C1 C10 C6 107.1(3) . . ?
C13 C10 C1 110.9(3) . . ?
C13 C10 C6 111.1(3) . . ?
C15 C10 C1 110.7(3) . . ?
C15 C10 C13 108.7(3) . . ?
C15 C10 C6 108.3(3) . . ?
C14 C13 C10 113.2(3) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C10 C13 H13A 108.9 . . ?
C10 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.2(3) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H5A C5 H5B 108.9 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
C4 C5 C6 104.8(3) . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
O1 C4 C5 126.2(4) . . ?
O1 C4 C3 125.5(4) . . ?
C5 C4 C3 108.4(4) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 C7 107.2(3) . . ?
C4 C3 C2 107.4(3) . . ?
C4 C3 C7 102.1(3) . . ?
C4 C3 C11 112.2(4) . . ?
C11 C3 C2 111.0(4) . . ?
C11 C3 C7 116.3(4) . . ?
C3 C7 C6 98.7(3) . . ?
C8 C7 C3 109.5(4) . . ?
C8 C7 C6 112.6(4) . . ?
C8 C7 C12 111.0(4) . . ?
C12 C7 C3 112.8(4) . . ?
C12 C7 C6 111.6(4) . . ?
C1 C9 H9 123.3 . . ?
C8 C9 C1 113.4(4) . . ?
C8 C9 H9 123.3 . . ?
C7 C8 H8 121.8 . . ?
C9 C8 C7 116.4(4) . . ?
C9 C8 H8 121.8 . . ?
C10 C6 H6 110.0 . . ?
C5 C6 C10 115.5(3) . . ?
C5 C6 C7 101.8(3) . . ?
C5 C6 H6 110.0 . . ?
C7 C6 C10 109.3(3) . . ?
C7 C6 H6 110.0 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C14 C13 C10 85.5(5) . . . . ?
O3 C14 C13 C10 -95.3(4) . . . . ?
O1 C4 C3 C2 -92.6(5) . . . . ?
O1 C4 C3 C7 154.8(4) . . . . ?
O1 C4 C3 C11 29.6(6) . . . . ?
C1 C10 C13 C14 64.8(5) . . . . ?
C1 C10 C6 C5 99.4(4) . . . . ?
C1 C10 C6 C7 -14.6(4) . . . . ?
C1 C2 C3 C4 -102.7(4) . . . . ?
C1 C2 C3 C7 6.4(5) . . . . ?
C1 C2 C3 C11 134.4(4) . . . . ?
C1 C9 C8 C7 -0.5(6) . . . . ?
C10 C1 C2 C3 57.2(5) . . . . ?
C10 C1 C9 C8 -59.4(5) . . . . ?
C13 C10 C6 C5 -21.8(5) . . . . ?
C13 C10 C6 C7 -135.9(4) . . . . ?
C2 C1 C10 C13 70.1(4) . . . . ?
C2 C1 C10 C15 -169.2(3) . . . . ?
C2 C1 C10 C6 -51.3(4) . . . . ?
C2 C1 C9 C8 58.8(5) . . . . ?
C2 C3 C7 C8 48.9(5) . . . . ?
C2 C3 C7 C6 -69.0(4) . . . . ?
C2 C3 C7 C12 173.0(4) . . . . ?
C5 C4 C3 C2 87.9(4) . . . . ?
C5 C4 C3 C7 -24.7(4) . . . . ?
C5 C4 C3 C11 -149.9(4) . . . . ?
C4 C5 C6 C10 -84.9(4) . . . . ?
C4 C5 C6 C7 33.4(4) . . . . ?
C4 C3 C7 C8 161.6(3) . . . . ?
C4 C3 C7 C6 43.8(4) . . . . ?
C4 C3 C7 C12 -74.2(4) . . . . ?
C15 C10 C13 C14 -57.1(5) . . . . ?
C15 C10 C6 C5 -141.1(4) . . . . ?
C15 C10 C6 C7 104.8(4) . . . . ?
C3 C7 C8 C9 -56.3(5) . . . . ?
C3 C7 C6 C10 75.1(4) . . . . ?
C3 C7 C6 C5 -47.5(4) . . . . ?
C9 C1 C10 C13 -173.8(3) . . . . ?
C9 C1 C10 C15 -53.1(5) . . . . ?
C9 C1 C10 C6 64.8(4) . . . . ?
C9 C1 C2 C3 -59.9(4) . . . . ?
C8 C7 C6 C10 -40.4(5) . . . . ?
C8 C7 C6 C5 -163.0(4) . . . . ?
C6 C10 C13 C14 -176.2(3) . . . . ?
C6 C5 C4 O1 175.0(4) . . . . ?
C6 C5 C4 C3 -5.5(5) . . . . ?
C6 C7 C8 C9 52.4(5) . . . . ?
C12 C7 C8 C9 178.4(4) . . . . ?
C12 C7 C6 C10 -166.0(4) . . . . ?
C12 C7 C6 C5 71.3(4) . . . . ?
C11 C3 C7 C8 -75.9(5) . . . . ?
C11 C3 C7 C6 166.3(4) . . . . ?
C11 C3 C7 C12 48.3(5) . . . . ?

_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 1.840
_oxdiff_exptl_absorpt_empirical_full_min 0.536
####################################################################### 
# 
# 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_euf-c2
_database_code_depnum_ccdc_archive 'CCDC 2116457'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2020-10-24
_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 H18 O2'
_chemical_formula_sum            'C15 H18 O2'
_chemical_formula_weight         230.29
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   15.7599(4)
_cell_length_b                   11.9783(3)
_cell_length_c                   6.5394(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1234.49(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4329
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4050
_cell_measurement_theta_min      4.6170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75329
_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    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5875
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.569
_diffrn_reflns_theta_min         4.637
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00 150.00   98
  2  ω     23.00  97.00   1.00    1.00    --   41.11-125.00-120.00   74
  3  ω    -47.00 129.00   1.00    1.00    --   41.11   0.00  30.00  176
  4  ω     34.00 121.00   1.00    1.49    --  106.95-125.00-150.00   87
  5  ω     94.00 178.00   1.00    1.49    --  106.95 125.00-120.00   84
  6  ω     81.00 178.00   1.00    1.49    --  106.95  45.00 -30.00   97
  7  ω     81.00 178.00   1.00    1.49    --  106.95  45.00-150.00   97
  8  ω     25.00 109.00   1.00    1.49    --  106.95 -95.00   0.00   84
  9  ω   -115.00 -50.00   1.00    1.00    --  -41.11 -38.00  60.00   65
;
_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      -0.0942463000
_diffrn_orient_matrix_UB_12      -0.0337221000
_diffrn_orient_matrix_UB_13      -0.0027015000
_diffrn_orient_matrix_UB_21      -0.0249884000
_diffrn_orient_matrix_UB_22      0.1192220000
_diffrn_orient_matrix_UB_23      0.0655348000
_diffrn_orient_matrix_UB_31      -0.0061676000
_diffrn_orient_matrix_UB_32      0.0348903000
_diffrn_orient_matrix_UB_33      -0.2262047000
_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         0.580
_reflns_Friedel_fraction_full    0.712
_reflns_Friedel_fraction_max     0.683
_reflns_number_gt                2043
_reflns_number_total             2100
_reflns_odcompleteness_completeness 100.00
_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         0.192
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_coef       0.0042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0304
_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)+(0.0446P)²+0.2453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H3 of C3, H1 of C1, H5 of C5
 At 1.5 times of:
  All C(H,H,H) groups, H12A of C12
2.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 C12(H12A)
;
_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
O2 O 0.47157(8) 0.44036(12) 0.4167(3) 0.0272(3) Uani 1 1 d . . . . .
O1 O 0.75152(9) 0.18952(12) 0.1848(3) 0.0308(4) Uani 1 1 d . . . . .
C7 C 0.59901(11) 0.32290(15) 0.4491(3) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.74588(11) 0.26310(15) 0.3153(3) 0.0203(4) Uani 1 1 d . . . . .
C5 C 0.71504(11) 0.42108(16) 0.6229(3) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.718237 0.483421 0.719692 0.023 Uiso 1 1 calc R . . . .
C4 C 0.79356(11) 0.34838(16) 0.6316(3) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.55096(11) 0.21641(15) 0.4106(4) 0.0218(4) Uani 1 1 d . . . . .
C6 C 0.63662(11) 0.34421(15) 0.6661(3) 0.0190(4) Uani 1 1 d . . . . .
H6A H 0.653921 0.274809 0.730106 0.023 Uiso 1 1 calc R . . . .
H6B H 0.595753 0.381458 0.753525 0.023 Uiso 1 1 calc R . . . .
C8 C 0.54807(11) 0.43106(15) 0.4182(4) 0.0210(4) Uani 1 1 d . . . . .
C10 C 0.69885(11) 0.46159(15) 0.4025(3) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.67561(11) 0.34882(15) 0.3038(3) 0.0186(4) Uani 1 1 d . . . . .
H1 H 0.656389 0.359082 0.162572 0.022 Uiso 1 1 calc R . . . .
C9 C 0.61309(11) 0.52364(16) 0.3960(4) 0.0225(4) Uani 1 1 d . . . . .
H9A H 0.608641 0.576754 0.507481 0.027 Uiso 1 1 calc R . . . .
H9B H 0.605952 0.562847 0.267388 0.027 Uiso 1 1 calc R . . . .
C3 C 0.80581(11) 0.27265(16) 0.4845(3) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.852783 0.225762 0.489994 0.026 Uiso 1 1 calc R . . . .
C14 C 0.77040(13) 0.52611(16) 0.2998(3) 0.0237(4) Uani 1 1 d . . . . .
H14A H 0.780700 0.594042 0.373624 0.036 Uiso 1 1 calc GR . . . .
H14B H 0.754617 0.543501 0.161616 0.036 Uiso 1 1 calc GR . . . .
H14C H 0.820985 0.481458 0.299352 0.036 Uiso 1 1 calc GR . . . .
C12 C 0.53673(13) 0.14042(19) 0.5541(4) 0.0276(5) Uani 1 1 d . . . . .
H12A H 0.557972 0.161078 0.662145 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.51992(15) 0.19981(19) 0.1952(4) 0.0333(5) Uani 1 1 d . . . . .
H13A H 0.489223 0.264856 0.151809 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.483210 0.135910 0.190180 0.050 Uiso 1 1 calc GR . . . .
H13C H 0.567515 0.188070 0.106152 0.050 Uiso 1 1 calc GR . . . .
C15 C 0.84952(13) 0.36042(19) 0.8140(4) 0.0293(5) Uani 1 1 d . . . . .
H15A H 0.870928 0.435369 0.820365 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.896105 0.309091 0.803446 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.817587 0.344538 0.935530 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.5034(15) 0.071(2) 0.524(5) 0.036(7) 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
O2 C8 1.211(2) . ?
O1 C2 1.230(2) . ?
C7 C11 1.505(2) . ?
C7 C6 1.559(3) . ?
C7 C8 1.537(2) . ?
C7 C1 1.567(3) . ?
C2 C1 1.512(3) . ?
C2 C3 1.459(3) . ?
C5 C4 1.514(3) . ?
C5 C6 1.567(2) . ?
C5 C10 1.542(3) . ?
C4 C3 1.336(3) . ?
C4 C15 1.490(3) . ?
C11 C12 1.326(3) . ?
C11 C13 1.505(3) . ?
C8 C9 1.517(2) . ?
C10 C1 1.541(3) . ?
C10 C9 1.543(2) . ?
C10 C14 1.523(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 C7 C6 118.85(17) . . ?
C11 C7 C8 115.44(15) . . ?
C11 C7 C1 117.02(16) . . ?
C6 C7 C1 103.08(14) . . ?
C8 C7 C6 100.38(15) . . ?
C8 C7 C1 98.95(14) . . ?
O1 C2 C1 120.35(18) . . ?
O1 C2 C3 122.38(17) . . ?
C3 C2 C1 117.27(16) . . ?
C4 C5 C6 107.46(15) . . ?
C4 C5 C10 110.55(16) . . ?
C10 C5 C6 102.86(15) . . ?
C3 C4 C5 118.79(18) . . ?
C3 C4 C15 123.80(18) . . ?
C15 C4 C5 117.25(18) . . ?
C12 C11 C7 123.3(2) . . ?
C12 C11 C13 121.11(19) . . ?
C13 C11 C7 115.61(18) . . ?
C7 C6 C5 103.44(16) . . ?
O2 C8 C7 126.76(17) . . ?
O2 C8 C9 127.20(17) . . ?
C9 C8 C7 106.02(14) . . ?
C5 C10 C9 108.79(16) . . ?
C1 C10 C5 98.91(15) . . ?
C1 C10 C9 101.68(14) . . ?
C14 C10 C5 116.71(16) . . ?
C14 C10 C1 115.85(17) . . ?
C14 C10 C9 113.08(16) . . ?
C2 C1 C7 113.55(15) . . ?
C2 C1 C10 113.61(15) . . ?
C10 C1 C7 95.91(15) . . ?
C8 C9 C10 103.71(14) . . ?
C4 C3 C2 120.37(17) . . ?

_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 1.469
_oxdiff_exptl_absorpt_empirical_full_min 0.579
####################################################################### 
# 
# 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_4-6-3
_database_code_depnum_ccdc_archive 'CCDC 2116454'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-01-22
_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_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1773(4)
_cell_length_b                   8.4293(3)
_cell_length_c                   10.2788(4)
_cell_angle_alpha                105.855(3)
_cell_angle_beta                 112.987(4)
_cell_angle_gamma                94.197(3)
_cell_volume                     614.35(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7319
_cell_measurement_temperature    172(30)
_cell_measurement_theta_max      73.8020
_cell_measurement_theta_min      5.9140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59087
_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    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.12
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9918
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.675
_diffrn_reflns_theta_min         4.949
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172(30)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_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     -6.00  22.00   1.00    1.00    --   34.00  97.00  88.88   28
  2  ω     16.00 115.00   1.00    1.00    --   40.73  38.00-150.00   99
  3  ω     13.00 114.00   1.00    1.00    --   40.73  57.00 -60.00  101
  4  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00 150.00   81
  5  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00  30.00   81
  6  ω     23.00  97.00   1.00    1.00    --   40.73-125.00 -90.00   74
  7  ω     13.00 114.00   1.00    1.00    --   40.73  57.00 -60.00  101
  8  ω     12.00  45.00   1.00    1.00    --   46.00  82.00 110.99   33
  9  ω     12.00  46.00   1.00    1.00    --   46.00  81.00 178.98   34
 10  ω     12.00  40.00   1.00    1.00    --   46.00  83.00  17.43   28
 11  ω     21.00  47.00   1.00    1.00    --   54.00  79.00  47.38   26
 12  ω     20.00  46.00   1.00    1.00    --   54.00  81.00-175.27   26
 13  ω     26.00 133.00   1.00    1.00    --   58.00  74.00  86.93  107
 14  ω     26.00 134.00   1.00    1.00    --   58.00  76.00 -39.14  108
 15  ω     25.00 134.00   1.00    1.00    --   58.00  77.00 179.78  109
 16  ω     30.00 137.00   1.00    1.00    --   62.00  75.00 111.70  107
 17  ω     32.00  71.00   1.00    1.00    --   62.00  75.00 135.16   39
 18  ω     30.00  78.00   1.00    1.00    --   62.00  77.00-110.79   48
 19  ω     32.00 136.00   1.00    1.00    --   62.00  75.00  10.21  104
 20  ω     75.00 141.00   1.00    1.00    --   66.00  77.00-138.54   66
 21  ω     35.00  60.00   1.00    1.00    --   66.00  74.00 -19.12   25
 22  ω     33.00  68.00   1.00    1.00    --   66.00  77.00-138.54   35
 23  ω     64.00  98.00   1.00    1.00    --   66.00  74.00 -19.12   34
 24  ω     76.00 171.00   1.00    1.00    --  107.58  77.00 -60.00   95
 25  ω     84.00 178.00   1.00    1.00    --  107.58  61.00 120.00   94
 26  ω    133.00 159.00   1.00    1.00    --  107.58  77.00 150.00   26
 27  ω     77.00 125.00   1.00    1.00    --  107.58  77.00 150.00   48
 28  ω    112.00 140.00   1.00    1.00    --  107.58  45.00  30.00   28
 29  ω    117.00 173.00   1.00    1.00    --  107.58  77.00 -30.00   56
 30  ω     76.00 140.00   1.00    1.00    --  107.58  77.00 -90.00   64
 31  ω     80.00 109.00   1.00    1.00    --  107.58  77.00 -30.00   29
 32  ω     79.00 134.00   1.00    1.00    --  107.58  61.00  30.00   55
 33  ω     76.00 135.00   1.00    1.00    --  107.58  77.00  90.00   59
 34  ω     79.00 106.00   1.00    1.00    --  107.58  61.00 150.00   27
 35  ω     26.00 106.00   1.00    1.00    --  107.58 -95.00-120.00   80
 36  ω     72.00 116.00   1.00    1.00    --  107.58-125.00 120.00   44
 37  ω     78.00 109.00   1.00    1.00    --  107.58  61.00  90.00   31
 38  ω    119.00 177.00   1.00    1.00    --  107.58  77.00-120.00   58
 39  ω     75.00 161.00   1.00    1.00    --  107.58  77.00-180.00   86
 40  ω     79.00 104.00   1.00    1.00    --  107.58  77.00-120.00   25
 41  ω     83.00 111.00   1.00    1.00    --  107.58  61.00 -90.00   28
 42  ω    114.00 168.00   1.00    1.00    --  107.58  77.00-150.00   54
 43  ω     76.00 173.00   1.00    1.00    --  107.58  77.00  30.00   97
 44  ω     75.00 108.00   1.00    1.00    --  107.58  77.00-150.00   33
 45  ω     82.00 108.00   1.00    1.00    --  107.58  45.00  30.00   26
 46  ω     35.00 140.00   1.00    1.00    --  107.58 -77.00 -60.00  105
 47  ω    124.00 178.00   1.00    1.00    --  107.58  77.00  60.00   54
 48  ω     75.00 102.00   1.00    1.00    --  107.58  77.00  60.00   27
 49  ω     28.00 108.00   1.00    1.00    --  107.58 -95.00 150.00   80
;
_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      -0.2063528000
_diffrn_orient_matrix_UB_12      -0.0133905000
_diffrn_orient_matrix_UB_13      -0.0797714000
_diffrn_orient_matrix_UB_21      -0.0331551000
_diffrn_orient_matrix_UB_22      -0.1621152000
_diffrn_orient_matrix_UB_23      0.0357192000
_diffrn_orient_matrix_UB_31      0.0009374000
_diffrn_orient_matrix_UB_32      0.1057811000
_diffrn_orient_matrix_UB_33      0.1485782000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2289
_reflns_number_total             2447
_reflns_odcompleteness_completeness 99.73
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.074
_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)+(0.0477P)²+0.2284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1029
_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:
 C5(H5), C9(H9), C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,
 H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.80628(13) -0.26721(12) -0.70436(10) 0.0327(3) Uani 1 1 d . . . . .
H1 H -0.792343 -0.184647 -0.729370 0.049 Uiso 1 1 calc R U . . .
O2 O -0.24782(12) -0.02368(13) -0.22144(11) 0.0356(3) Uani 1 1 d . . . . .
C5 C -0.73898(15) -0.27592(15) -0.29406(13) 0.0215(3) Uani 1 1 d . . . . .
H5 H -0.851791 -0.307585 -0.286420 0.026 Uiso 1 1 calc R U . . .
C9 C -0.55311(15) -0.01416(14) -0.28292(13) 0.0216(3) Uani 1 1 d . . . . .
H9 H -0.534621 0.108637 -0.242184 0.026 Uiso 1 1 calc R U . . .
C10 C -0.74015(15) -0.10779(14) -0.32306(13) 0.0211(3) Uani 1 1 d . . . . .
C1 C -0.69260(15) -0.09165(14) -0.44640(13) 0.0214(3) Uani 1 1 d . . . . .
H1A H -0.747683 -0.008720 -0.490874 0.026 Uiso 1 1 calc R U . . .
C4 C -0.72668(15) -0.41979(14) -0.41305(13) 0.0226(3) Uani 1 1 d . . . . .
C8 C -0.38828(16) -0.08434(15) -0.22013(13) 0.0224(3) Uani 1 1 d . . . . .
C7 C -0.39959(15) -0.21345(15) -0.14913(13) 0.0214(3) Uani 1 1 d . . . . .
C11 C -0.26027(16) -0.29028(15) -0.09538(13) 0.0236(3) Uani 1 1 d . . . . .
C2 C -0.67094(16) -0.23944(15) -0.55595(13) 0.0240(3) Uani 1 1 d . . . . .
H2 H -0.550556 -0.215144 -0.553555 0.029 Uiso 1 1 calc R U . . .
C3 C -0.69290(16) -0.40073(15) -0.52482(14) 0.0242(3) Uani 1 1 d . . . . .
H3 H -0.681932 -0.496437 -0.589498 0.029 Uiso 1 1 calc R U . . .
C6 C -0.57929(16) -0.24853(15) -0.14062(14) 0.0236(3) Uani 1 1 d . . . . .
H6A H -0.586514 -0.154317 -0.065240 0.028 Uiso 1 1 calc R U . . .
H6B H -0.587157 -0.348124 -0.111682 0.028 Uiso 1 1 calc R U . . .
C12 C -0.08512(17) -0.26631(17) -0.10991(16) 0.0309(3) Uani 1 1 d . . . . .
H12A H 0.001491 -0.175954 -0.024612 0.046 Uiso 1 1 calc R U . . .
H12B H -0.106064 -0.239500 -0.199336 0.046 Uiso 1 1 calc R U . . .
H12C H -0.038831 -0.368170 -0.115065 0.046 Uiso 1 1 calc R U . . .
C14 C -0.87051(17) -0.00787(16) -0.28577(15) 0.0279(3) Uani 1 1 d . . . . .
H14A H -0.846045 0.011705 -0.182808 0.042 Uiso 1 1 calc R U . . .
H14B H -0.992571 -0.069704 -0.348650 0.042 Uiso 1 1 calc R U . . .
H14C H -0.856026 0.098088 -0.302059 0.042 Uiso 1 1 calc R U . . .
C15 C -0.74973(19) -0.59007(16) -0.39472(16) 0.0332(3) Uani 1 1 d . . . . .
H15A H -0.859869 -0.611643 -0.383926 0.050 Uiso 1 1 calc R U . . .
H15B H -0.648551 -0.591989 -0.307284 0.050 Uiso 1 1 calc R U . . .
H15C H -0.755462 -0.675144 -0.481251 0.050 Uiso 1 1 calc R U . . .
C13 C -0.26451(19) -0.41084(17) -0.01219(16) 0.0327(3) Uani 1 1 d . . . . .
H13A H -0.281878 -0.523817 -0.075738 0.049 Uiso 1 1 calc R U . . .
H13B H -0.362531 -0.401549 0.016898 0.049 Uiso 1 1 calc R U . . .
H13C H -0.151819 -0.384178 0.075428 0.049 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 H1 0.8200 . ?
O1 C2 1.4335(14) . ?
O2 C8 1.2292(15) . ?
C5 H5 0.9800 . ?
C5 C10 1.5258(15) . ?
C5 C4 1.5100(17) . ?
C5 C6 1.5474(16) . ?
C9 H9 0.9800 . ?
C9 C10 1.5117(16) . ?
C9 C1 1.5315(16) . ?
C9 C8 1.4930(16) . ?
C10 C1 1.4995(16) . ?
C10 C14 1.5056(16) . ?
C1 H1A 0.9800 . ?
C1 C2 1.5076(17) . ?
C4 C3 1.3283(18) . ?
C4 C15 1.5057(16) . ?
C8 C7 1.4824(16) . ?
C7 C11 1.3545(17) . ?
C7 C6 1.5183(16) . ?
C11 C12 1.5019(17) . ?
C11 C13 1.5026(17) . ?
C2 H2 0.9800 . ?
C2 C3 1.4934(17) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C2 O1 H1 109.5 . . ?
C10 C5 H5 107.8 . . ?
C10 C5 C6 107.87(9) . . ?
C4 C5 H5 107.8 . . ?
C4 C5 C10 115.30(10) . . ?
C4 C5 C6 110.07(9) . . ?
C6 C5 H5 107.8 . . ?
C10 C9 H9 114.5 . . ?
C10 C9 C1 59.04(7) . . ?
C1 C9 H9 114.5 . . ?
C8 C9 H9 114.5 . . ?
C8 C9 C10 121.35(10) . . ?
C8 C9 C1 121.80(10) . . ?
C9 C10 C5 113.16(9) . . ?
C1 C10 C5 117.86(10) . . ?
C1 C10 C9 61.14(7) . . ?
C1 C10 C14 119.38(10) . . ?
C14 C10 C5 115.76(10) . . ?
C14 C10 C9 118.19(10) . . ?
C9 C1 H1A 113.7 . . ?
C10 C1 C9 59.82(7) . . ?
C10 C1 H1A 113.7 . . ?
C10 C1 C2 122.96(10) . . ?
C2 C1 C9 122.78(10) . . ?
C2 C1 H1A 113.7 . . ?
C3 C4 C5 123.65(11) . . ?
C3 C4 C15 121.05(11) . . ?
C15 C4 C5 115.27(11) . . ?
O2 C8 C9 117.99(10) . . ?
O2 C8 C7 123.72(11) . . ?
C7 C8 C9 118.10(10) . . ?
C8 C7 C6 113.83(10) . . ?
C11 C7 C8 122.46(11) . . ?
C11 C7 C6 123.70(10) . . ?
C7 C11 C12 125.11(11) . . ?
C7 C11 C13 122.91(11) . . ?
C12 C11 C13 111.98(11) . . ?
O1 C2 C1 110.11(9) . . ?
O1 C2 H2 109.0 . . ?
O1 C2 C3 106.26(10) . . ?
C1 C2 H2 109.0 . . ?
C3 C2 C1 113.35(10) . . ?
C3 C2 H2 109.0 . . ?
C4 C3 C2 125.86(11) . . ?
C4 C3 H3 117.1 . . ?
C2 C3 H3 117.1 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 C5 110.26(9) . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 . . ?
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 . . ?

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 C4 -121.60(13) . . . . ?
O2 C8 C7 C11 -8.23(19) . . . . ?
O2 C8 C7 C6 170.89(12) . . . . ?
C5 C10 C1 C9 -102.51(11) . . . . ?
C5 C10 C1 C2 9.17(16) . . . . ?
C5 C4 C3 C2 -3.18(19) . . . . ?
C9 C10 C1 C2 111.68(12) . . . . ?
C9 C1 C2 O1 -171.00(10) . . . . ?
C9 C1 C2 C3 70.13(14) . . . . ?
C9 C8 C7 C11 176.81(11) . . . . ?
C9 C8 C7 C6 -4.08(15) . . . . ?
C10 C5 C4 C3 9.43(16) . . . . ?
C10 C5 C4 C15 -172.45(10) . . . . ?
C10 C5 C6 C7 -68.63(12) . . . . ?
C10 C9 C1 C2 -111.96(12) . . . . ?
C10 C9 C8 O2 163.84(11) . . . . ?
C10 C9 C8 C7 -20.91(16) . . . . ?
C10 C1 C2 O1 116.16(11) . . . . ?
C10 C1 C2 C3 -2.71(15) . . . . ?
C1 C9 C10 C5 110.16(11) . . . . ?
C1 C9 C10 C14 -109.89(12) . . . . ?
C1 C9 C8 O2 93.18(14) . . . . ?
C1 C9 C8 C7 -91.57(13) . . . . ?
C1 C2 C3 C4 -0.53(17) . . . . ?
C4 C5 C10 C9 -80.28(12) . . . . ?
C4 C5 C10 C1 -11.85(14) . . . . ?
C4 C5 C10 C14 138.75(11) . . . . ?
C4 C5 C6 C7 57.95(12) . . . . ?
C8 C9 C10 C5 -0.58(16) . . . . ?
C8 C9 C10 C1 -110.74(12) . . . . ?
C8 C9 C10 C14 139.37(12) . . . . ?
C8 C9 C1 C10 109.99(12) . . . . ?
C8 C9 C1 C2 -1.98(17) . . . . ?
C8 C7 C11 C12 -4.78(19) . . . . ?
C8 C7 C11 C13 174.90(11) . . . . ?
C8 C7 C6 C5 48.15(13) . . . . ?
C11 C7 C6 C5 -132.75(12) . . . . ?
C6 C5 C10 C9 43.18(13) . . . . ?
C6 C5 C10 C1 111.60(11) . . . . ?
C6 C5 C10 C14 -97.79(12) . . . . ?
C6 C5 C4 C3 -112.86(12) . . . . ?
C6 C5 C4 C15 65.27(13) . . . . ?
C6 C7 C11 C12 176.19(11) . . . . ?
C6 C7 C11 C13 -4.13(19) . . . . ?
C14 C10 C1 C9 107.98(12) . . . . ?
C14 C10 C1 C2 -140.34(11) . . . . ?
C15 C4 C3 C2 178.80(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 4.053
_oxdiff_exptl_absorpt_empirical_full_min 0.585
####################################################################### 
# 
# 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_22-23-3_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2116453'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2020-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9108(6)
_cell_length_b                   6.8929(4)
_cell_length_c                   26.7108(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.378(7)
_cell_angle_gamma                90
_cell_volume                     1268.67(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3460
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2720
_cell_measurement_theta_min      3.1860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48092
_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    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            3353
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.643
_diffrn_reflns_theta_min         3.319
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  29.00   1.00    1.00    --  -40.98  57.00  30.00   94
  2  ω    -89.00 -63.00   1.00    1.00    --  -40.98 -37.00  30.00   26
  3  ω   -108.00 -19.00   1.00    1.00    --  -40.98 -57.00   0.00   89
  4  ω    -59.00 -17.00   1.00    1.00    --  -40.98 -37.00  30.00   42
  5  ω   -109.00 -14.00   1.00    1.00    --  -40.98 -57.00-120.00   95
  6  ω     59.00  90.00   1.00    1.00    --   40.98-125.00-180.00   31
  7  ω    113.00 177.00   1.00    1.00    --  106.95  77.00  30.00   64
  8  ω     74.00 101.00   1.00    1.00    --  106.95  77.00  30.00   27
  9  ω    106.00 177.00   1.00    1.00    --  106.95  99.00-174.00   71
 10  ω     74.00 100.00   1.00    1.00    --  106.95  77.00  60.00   26
 11  ω    107.00 133.00   1.00    1.00    --  106.95  77.00  60.00   26
 12  ω     83.00 164.00   1.00    1.00    --  106.95  45.00 120.00   81
 13  ω     79.00 110.00   1.00    1.00    --  106.95  61.00  60.00   31
 14  ω     77.00 103.00   1.00    1.00    --  106.95  77.00   0.00   26
 15  ω    134.00 160.00   1.00    1.00    --  106.95  77.00  90.00   26
 16  ω     79.00 104.00   1.00    1.00    --  106.95  61.00  90.00   25
 17  ω     74.00 100.00   1.00    1.00    --  106.95  77.00  90.00   26
 18  ω     25.00 105.00   1.00    1.00    --  106.95 -94.00-120.00   80
 19  ω    118.00 145.00   1.00    1.00    --  106.95  77.00   0.00   27
 20  ω     78.00 104.00   1.00    1.00    --  106.95  61.00  30.00   26
 21  ω    100.00 159.00   1.00    1.00    --  106.95 125.00  60.00   59
 22  ω     96.00 121.00   1.00    1.00    --  106.95  45.00   0.00   25
 23  ω     82.00 108.00   1.00    1.00    --  106.95  45.00  60.00   26
 24  ω     83.00 110.00   1.00    1.00    --  106.95  45.00  90.00   27
 25  ω     37.00  61.00   1.00    1.00    --  106.95 -61.00  60.00   24
;
_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      -0.1547587000
_diffrn_orient_matrix_UB_12      -0.0414989000
_diffrn_orient_matrix_UB_13      0.0372040000
_diffrn_orient_matrix_UB_21      -0.1165572000
_diffrn_orient_matrix_UB_22      -0.1208699000
_diffrn_orient_matrix_UB_23      -0.0403542000
_diffrn_orient_matrix_UB_31      0.1118924000
_diffrn_orient_matrix_UB_32      -0.1833091000
_diffrn_orient_matrix_UB_33      0.0181533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3177
_reflns_number_total             3353
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 (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         0.379
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0865
_refine_ls_restrained_S_all      1.184
_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)+(0.1521P)²+4.2571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2903
_refine_ls_wR_factor_ref         0.2973
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_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
O2 O -0.8966(6) -0.3038(5) -0.31907(13) 0.0219(8) Uani 1 1 d . . . . .
O1 O -0.5381(6) -0.9917(5) -0.30209(13) 0.0232(8) Uani 1 1 d . . . . .
O3 O -0.2940(7) -0.4973(5) -0.45196(13) 0.0261(9) Uani 1 1 d . . . . .
C5 C -0.7174(7) -0.4984(7) -0.37653(16) 0.0151(10) Uani 1 1 d . . . . .
C9 C -0.3627(7) -0.3861(7) -0.37104(17) 0.0162(10) Uani 1 1 d . . . . .
H9A H -0.421435 -0.268753 -0.359056 0.019 Uiso 1 1 calc R . . . .
H9B H -0.244224 -0.410277 -0.350129 0.019 Uiso 1 1 calc R . . . .
C11 C -0.2806(8) -0.1579(7) -0.44505(19) 0.0213(11) Uani 1 1 d . . . . .
C6 C -0.7671(7) -0.4156(7) -0.32509(17) 0.0154(10) Uani 1 1 d . . . . .
C3 C -0.7868(8) -0.8396(7) -0.35268(18) 0.0189(10) Uani 1 1 d . . . . .
H3 H -0.866292 -0.948557 -0.354502 0.023 Uiso 1 1 calc R . . . .
C8 C -0.5020(7) -0.5562(6) -0.36655(16) 0.0139(9) Uani 1 1 d . . . . .
H8 H -0.471205 -0.657507 -0.390425 0.017 Uiso 1 1 calc R . . . .
C7 C -0.6271(8) -0.5048(7) -0.28512(17) 0.0174(10) Uani 1 1 d . . . . .
H7A H -0.697347 -0.573380 -0.260479 0.021 Uiso 1 1 calc R . . . .
H7B H -0.547954 -0.405099 -0.268064 0.021 Uiso 1 1 calc R . . . .
C1 C -0.4992(8) -0.6466(7) -0.31273(16) 0.0157(10) Uani 1 1 d . . . . .
C2 C -0.6031(8) -0.8426(7) -0.32030(17) 0.0171(10) Uani 1 1 d . . . . .
C4 C -0.8390(8) -0.6820(7) -0.37924(17) 0.0186(10) Uani 1 1 d . . . . .
H4 H -0.953213 -0.684519 -0.400029 0.022 Uiso 1 1 calc R . . . .
C14 C -0.3002(8) -0.6762(7) -0.28558(18) 0.0197(11) Uani 1 1 d . . . . .
H14A H -0.235755 -0.553270 -0.281318 0.030 Uiso 1 1 calc GR . . . .
H14B H -0.224731 -0.760725 -0.304985 0.030 Uiso 1 1 calc GR . . . .
H14C H -0.314405 -0.733265 -0.253285 0.030 Uiso 1 1 calc GR . . . .
C13 C -0.2563(11) -0.1486(9) -0.5005(2) 0.0324(14) Uani 1 1 d . . . . .
H13A H -0.143028 -0.220635 -0.507842 0.049 Uiso 1 1 calc GR . . . .
H13B H -0.241955 -0.015842 -0.510396 0.049 Uiso 1 1 calc GR . . . .
H13C H -0.368566 -0.203502 -0.518609 0.049 Uiso 1 1 calc GR . . . .
C12 C -0.2671(8) -0.0035(8) -0.4154(2) 0.0245(11) Uani 1 1 d . . . . .
C15 C -0.7695(8) -0.3601(7) -0.42032(18) 0.0192(10) Uani 1 1 d . . . . .
H15A H -0.696598 -0.242179 -0.415433 0.029 Uiso 1 1 calc GR . . . .
H15B H -0.905712 -0.331342 -0.421809 0.029 Uiso 1 1 calc GR . . . .
H15C H -0.738819 -0.420086 -0.451170 0.029 Uiso 1 1 calc GR . . . .
C10 C -0.3142(7) -0.3571(7) -0.42524(18) 0.0176(10) Uani 1 1 d . . . . .
H12A H -0.236(11) 0.117(10) -0.430(2) 0.031(17) Uiso 1 1 d . . . . .
H12B H -0.280(11) -0.014(9) -0.378(2) 0.030(17) 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
O2 C6 1.201(6) . ?
O1 C2 1.209(6) . ?
O3 C10 1.216(6) . ?
C5 C6 1.551(6) . ?
C5 C8 1.544(7) . ?
C5 C4 1.518(7) . ?
C5 C15 1.530(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.528(6) . ?
C9 C10 1.524(7) . ?
C11 C13 1.504(7) . ?
C11 C12 1.326(8) . ?
C11 C10 1.496(7) . ?
C6 C7 1.515(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.480(7) . ?
C3 C4 1.332(7) . ?
C8 H8 0.9800 . ?
C8 C1 1.565(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C1 1.543(7) . ?
C1 C2 1.536(7) . ?
C1 C14 1.519(7) . ?
C4 H4 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.94(7) . ?
C12 H12B 1.02(6) . ?
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
C8 C5 C6 102.6(4) . . ?
C4 C5 C6 100.9(4) . . ?
C4 C5 C8 108.4(4) . . ?
C4 C5 C15 112.7(4) . . ?
C15 C5 C6 113.1(4) . . ?
C15 C5 C8 117.4(4) . . ?
H9A C9 H9B 108.0 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C10 C9 C8 111.2(4) . . ?
C12 C11 C13 123.1(5) . . ?
C12 C11 C10 122.1(5) . . ?
C10 C11 C13 114.8(4) . . ?
O2 C6 C5 124.9(4) . . ?
O2 C6 C7 127.5(4) . . ?
C7 C6 C5 107.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.5(5) . . ?
C5 C8 H8 109.0 . . ?
C5 C8 C1 101.9(4) . . ?
C9 C8 C5 113.2(4) . . ?
C9 C8 H8 109.0 . . ?
C9 C8 C1 114.4(4) . . ?
C1 C8 H8 109.0 . . ?
C6 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
C6 C7 C1 106.2(4) . . ?
H7A C7 H7B 108.7 . . ?
C1 C7 H7A 110.5 . . ?
C1 C7 H7B 110.5 . . ?
C7 C1 C8 102.7(4) . . ?
C2 C1 C8 104.8(3) . . ?
C2 C1 C7 109.9(4) . . ?
C14 C1 C8 116.1(4) . . ?
C14 C1 C7 112.8(4) . . ?
C14 C1 C2 110.0(4) . . ?
O1 C2 C3 121.5(5) . . ?
O1 C2 C1 122.6(5) . . ?
C3 C2 C1 115.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.1 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 . . ?
C11 C12 H12A 118(4) . . ?
C11 C12 H12B 122(4) . . ?
H12A C12 H12B 120(5) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C10 C9 119.8(4) . . ?
O3 C10 C11 119.6(4) . . ?
C11 C10 C9 120.5(4) . . ?

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 C6 C7 C1 176.6(5) . . . . ?
C5 C6 C7 C1 -2.1(5) . . . . ?
C5 C8 C1 C7 -42.3(4) . . . . ?
C5 C8 C1 C2 72.6(4) . . . . ?
C5 C8 C1 C14 -165.9(4) . . . . ?
C9 C8 C1 C7 80.1(5) . . . . ?
C9 C8 C1 C2 -165.0(4) . . . . ?
C9 C8 C1 C14 -43.4(6) . . . . ?
C6 C5 C8 C9 -82.6(4) . . . . ?
C6 C5 C8 C1 40.7(4) . . . . ?
C6 C5 C4 C3 -75.9(5) . . . . ?
C6 C7 C1 C8 27.4(5) . . . . ?
C6 C7 C1 C2 -83.8(4) . . . . ?
C6 C7 C1 C14 153.0(4) . . . . ?
C8 C5 C6 O2 156.9(4) . . . . ?
C8 C5 C6 C7 -24.4(5) . . . . ?
C8 C5 C4 C3 31.4(6) . . . . ?
C8 C9 C10 O3 -37.5(7) . . . . ?
C8 C9 C10 C11 145.8(5) . . . . ?
C8 C1 C2 O1 132.3(5) . . . . ?
C8 C1 C2 C3 -46.0(5) . . . . ?
C7 C1 C2 O1 -118.0(5) . . . . ?
C7 C1 C2 C3 63.7(5) . . . . ?
C2 C3 C4 C5 -1.7(7) . . . . ?
C4 C5 C6 O2 -91.2(5) . . . . ?
C4 C5 C6 C7 87.5(4) . . . . ?
C4 C5 C8 C9 171.1(4) . . . . ?
C4 C5 C8 C1 -65.5(4) . . . . ?
C4 C3 C2 O1 -168.4(5) . . . . ?
C4 C3 C2 C1 9.9(7) . . . . ?
C14 C1 C2 O1 6.8(6) . . . . ?
C14 C1 C2 C3 -171.5(4) . . . . ?
C13 C11 C10 O3 9.9(8) . . . . ?
C13 C11 C10 C9 -173.4(5) . . . . ?
C12 C11 C10 O3 -168.0(6) . . . . ?
C12 C11 C10 C9 8.7(8) . . . . ?
C15 C5 C6 O2 29.5(7) . . . . ?
C15 C5 C6 C7 -151.8(4) . . . . ?
C15 C5 C8 C9 42.0(6) . . . . ?
C15 C5 C8 C1 165.4(4) . . . . ?
C15 C5 C4 C3 163.1(5) . . . . ?
C10 C9 C8 C5 -85.9(5) . . . . ?
C10 C9 C8 C1 157.9(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 1.811
_oxdiff_exptl_absorpt_empirical_full_min 0.568
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5423 1101 6557 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.4577 1094 6557 nmt 0.9994 -0.0003 0.0005 -0.0003 -0.9999 -0.0001 -0.5813
0.0023 -0.9999

_twin_special_details            
;
Component 2 rotated by 179.9837° 
 around [0.96 -0.00 -0.28] (reciprocal) or [1.00 0.00 0.00] (direct)
;
####################################################################### 
# 
# 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_14-17-3
_database_code_depnum_ccdc_archive 'CCDC 2116456'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-10-19
_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_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           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                   7.7470(3)
_cell_length_b                   11.9790(4)
_cell_length_c                   13.6765(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.716(3)
_cell_angle_gamma                90
_cell_volume                     1250.99(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5448
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3170
_cell_measurement_theta_min      4.9230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55476
_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    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10185
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.713
_diffrn_reflns_theta_min         4.939
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    1.00    --  -40.98 -57.00 150.00  100
  2  ω   -113.00 -62.00   1.00    1.00    --  -40.98-143.00 -53.00   51
  3  ω   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00-120.00  100
  4  ω   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 -30.00  100
  5  ω   -105.00 -12.00   1.00    1.00    --  -40.98 143.00   1.00   93
  6  ω     81.00 178.00   1.00    1.00    --  106.95  45.00   0.00   97
  7  ω     94.00 178.00   1.00    1.00    --  106.95 125.00 120.00   84
  8  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00  60.00   99
  9  ω     34.00 121.00   1.00    1.00    --  106.95-125.00  90.00   87
 10  ω     31.00 135.00   1.00    1.00    --  106.95 -30.00-180.00  104
 11  ω     31.00 135.00   1.00    1.00    --  106.95 -30.00 150.00  104
 12  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-150.00   84
 13  ω     24.00 109.00   1.00    1.00    --  106.95 -94.00-120.00   85
 14  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-120.00   84
 15  ω     30.00 114.00   1.00    1.00    --  106.95-108.00-163.00   84
 16  ω     98.00 168.00   1.00    1.00    --  106.95 125.00  60.00   70
;
_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      -0.0163049000
_diffrn_orient_matrix_UB_12      0.1157873000
_diffrn_orient_matrix_UB_13      0.0466223000
_diffrn_orient_matrix_UB_21      -0.0080008000
_diffrn_orient_matrix_UB_22      -0.0554159000
_diffrn_orient_matrix_UB_23      0.1007276000
_diffrn_orient_matrix_UB_31      0.2010103000
_diffrn_orient_matrix_UB_32      0.0071952000
_diffrn_orient_matrix_UB_33      0.0272351000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2259
_reflns_number_total             2510
_reflns_odcompleteness_completeness 99.96
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.046
_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)+(0.1058P)²+0.2654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1612
_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(H2), C1(H1A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 -0.39378(14) -0.15845(9) -0.59473(8) 0.0331(3) Uani 1 1 d . . . . .
H1 H -0.299265 -0.161564 -0.557362 0.050 Uiso 1 1 calc R U . . .
O2 O -1.06711(13) -0.12661(10) -0.46081(8) 0.0348(3) Uani 1 1 d . . . . .
C4 C -0.46046(19) -0.35736(12) -0.41214(11) 0.0270(3) Uani 1 1 d . . . . .
C10 C -0.60471(18) -0.17389(12) -0.39454(10) 0.0255(3) Uani 1 1 d . . . . .
C9 C -0.76962(18) -0.11748(12) -0.36849(11) 0.0276(4) Uani 1 1 d . . . . .
H9A H -0.792610 -0.142755 -0.304539 0.033 Uiso 1 1 calc R U . . .
H9B H -0.757092 -0.036904 -0.367027 0.033 Uiso 1 1 calc R U . . .
C2 C -0.51413(17) -0.23554(12) -0.56175(10) 0.0265(3) Uani 1 1 d . . . . .
H2 H -0.580387 -0.271240 -0.620885 0.032 Uiso 1 1 calc R U . . .
C8 C -0.91442(19) -0.15341(12) -0.45094(11) 0.0279(4) Uani 1 1 d . . . . .
C1 C -0.64637(17) -0.17301(12) -0.50953(10) 0.0253(3) Uani 1 1 d . . . . .
H1A H -0.661025 -0.096153 -0.534080 0.030 Uiso 1 1 calc R U . . .
C3 C -0.41789(19) -0.32612(12) -0.49869(11) 0.0270(3) Uani 1 1 d . . . . .
H3 H -0.325067 -0.361774 -0.520841 0.032 Uiso 1 1 calc R U . . .
C14 C -0.43640(19) -0.11882(13) -0.34339(11) 0.0296(4) Uani 1 1 d . . . . .
H14A H -0.417995 -0.136252 -0.273889 0.044 Uiso 1 1 calc R U . . .
H14B H -0.445529 -0.039386 -0.352049 0.044 Uiso 1 1 calc R U . . .
H14C H -0.339523 -0.146082 -0.371959 0.044 Uiso 1 1 calc R U . . .
C7 C -0.82892(18) -0.23144(12) -0.51717(11) 0.0276(4) Uani 1 1 d . . . . .
C5 C -0.61466(18) -0.30100(12) -0.37789(10) 0.0267(3) Uani 1 1 d . . . . .
H5 H -0.619794 -0.318646 -0.308471 0.032 Uiso 1 1 calc R U . . .
C6 C -0.78640(19) -0.33483(13) -0.44751(11) 0.0299(4) Uani 1 1 d . . . . .
H6A H -0.879855 -0.348655 -0.409951 0.036 Uiso 1 1 calc R U . . .
H6B H -0.768982 -0.401200 -0.485296 0.036 Uiso 1 1 calc R U . . .
C15 C -0.3675(2) -0.44603(13) -0.34687(12) 0.0333(4) Uani 1 1 d . . . . .
H15A H -0.265452 -0.469487 -0.372588 0.050 Uiso 1 1 calc R U . . .
H15B H -0.444271 -0.508616 -0.344998 0.050 Uiso 1 1 calc R U . . .
H15C H -0.333000 -0.417020 -0.281040 0.050 Uiso 1 1 calc R U . . .
C11 C -0.93444(19) -0.25016(15) -0.61839(12) 0.0363(4) Uani 1 1 d . . . . .
C12 C -1.0172(2) -0.34606(18) -0.64458(14) 0.0453(5) Uani 1 1 d . . . . .
C13 C -0.9460(2) -0.15195(18) -0.68726(13) 0.0464(5) Uani 1 1 d . . . . .
H13A H -0.831814 -0.135347 -0.701845 0.070 Uiso 1 1 calc R U . . .
H13B H -0.989735 -0.088393 -0.656332 0.070 Uiso 1 1 calc R U . . .
H13C H -1.023904 -0.169255 -0.747682 0.070 Uiso 1 1 calc R U . . .
H12A H -1.007(3) -0.4151(19) -0.5957(17) 0.054(6) Uiso 1 1 d . . . . .
H12B H -1.084(3) -0.3562(19) -0.7100(19) 0.060(7) 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 H1 0.8200 . ?
O1 C2 1.4378(17) . ?
O2 C8 1.2111(19) . ?
C4 C3 1.335(2) . ?
C4 C5 1.5136(19) . ?
C4 C15 1.492(2) . ?
C10 C9 1.5393(18) . ?
C10 C1 1.5512(19) . ?
C10 C14 1.5221(19) . ?
C10 C5 1.543(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.513(2) . ?
C2 H2 0.9800 . ?
C2 C1 1.5387(18) . ?
C2 C3 1.503(2) . ?
C8 C7 1.5281(19) . ?
C1 H1A 0.9800 . ?
C1 C7 1.5656(18) . ?
C3 H3 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C7 C6 1.563(2) . ?
C7 C11 1.501(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.554(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 C12 1.335(3) . ?
C11 C13 1.500(3) . ?
C12 H12A 1.06(2) . ?
C12 H12B 0.96(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C2 O1 H1 109.5 . . ?
C3 C4 C5 118.39(13) . . ?
C3 C4 C15 124.30(14) . . ?
C15 C4 C5 117.30(12) . . ?
C9 C10 C1 101.12(11) . . ?
C9 C10 C5 109.56(11) . . ?
C14 C10 C9 112.55(11) . . ?
C14 C10 C1 118.59(12) . . ?
C14 C10 C5 114.84(12) . . ?
C5 C10 C1 98.58(11) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C8 C9 C10 104.04(11) . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
O1 C2 H2 107.4 . . ?
O1 C2 C1 110.53(11) . . ?
O1 C2 C3 111.01(11) . . ?
C1 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C3 C2 C1 112.93(11) . . ?
O2 C8 C9 126.52(13) . . ?
O2 C8 C7 127.52(14) . . ?
C9 C8 C7 105.95(12) . . ?
C10 C1 H1A 110.2 . . ?
C10 C1 C7 95.49(10) . . ?
C2 C1 C10 115.24(11) . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 C7 114.59(12) . . ?
C7 C1 H1A 110.2 . . ?
C4 C3 C2 122.57(13) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
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 . . ?
C8 C7 C1 99.44(11) . . ?
C8 C7 C6 101.03(11) . . ?
C6 C7 C1 102.62(11) . . ?
C11 C7 C8 114.51(12) . . ?
C11 C7 C1 118.27(12) . . ?
C11 C7 C6 118.01(13) . . ?
C4 C5 C10 109.43(11) . . ?
C4 C5 H5 111.5 . . ?
C4 C5 C6 109.45(11) . . ?
C10 C5 H5 111.5 . . ?
C10 C5 C6 103.05(11) . . ?
C6 C5 H5 111.5 . . ?
C7 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C5 C6 C7 103.73(11) . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
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 . . ?
C12 C11 C7 122.56(17) . . ?
C12 C11 C13 122.10(16) . . ?
C13 C11 C7 115.30(15) . . ?
C11 C12 H12A 121.5(12) . . ?
C11 C12 H12B 121.1(14) . . ?
H12A C12 H12B 117.3(18) . . ?
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 . . ?

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 C1 C10 -99.37(14) . . . . ?
O1 C2 C1 C7 151.24(12) . . . . ?
O1 C2 C3 C4 132.91(14) . . . . ?
O2 C8 C7 C1 145.32(15) . . . . ?
O2 C8 C7 C6 -109.73(17) . . . . ?
O2 C8 C7 C11 18.2(2) . . . . ?
C4 C5 C6 C7 -101.45(13) . . . . ?
C10 C9 C8 O2 -178.79(14) . . . . ?
C10 C9 C8 C7 2.26(15) . . . . ?
C10 C1 C7 C8 54.12(12) . . . . ?
C10 C1 C7 C6 -49.53(12) . . . . ?
C10 C1 C7 C11 178.66(13) . . . . ?
C10 C5 C6 C7 14.91(13) . . . . ?
C9 C10 C1 C2 -173.89(11) . . . . ?
C9 C10 C1 C7 -53.39(12) . . . . ?
C9 C10 C5 C4 175.01(11) . . . . ?
C9 C10 C5 C6 58.64(14) . . . . ?
C9 C8 C7 C1 -35.74(14) . . . . ?
C9 C8 C7 C6 69.21(13) . . . . ?
C9 C8 C7 C11 -162.86(13) . . . . ?
C2 C1 C7 C8 175.11(11) . . . . ?
C2 C1 C7 C6 71.47(14) . . . . ?
C2 C1 C7 C11 -60.35(17) . . . . ?
C8 C7 C6 C5 -80.58(12) . . . . ?
C8 C7 C11 C12 -107.11(17) . . . . ?
C8 C7 C11 C13 70.78(16) . . . . ?
C1 C10 C9 C8 32.61(14) . . . . ?
C1 C10 C5 C4 69.91(13) . . . . ?
C1 C10 C5 C6 -46.47(12) . . . . ?
C1 C2 C3 C4 8.1(2) . . . . ?
C1 C7 C6 C5 21.83(13) . . . . ?
C1 C7 C11 C12 136.15(15) . . . . ?
C1 C7 C11 C13 -45.96(18) . . . . ?
C3 C4 C5 C10 -44.52(17) . . . . ?
C3 C4 C5 C6 67.73(17) . . . . ?
C3 C2 C1 C10 25.67(17) . . . . ?
C3 C2 C1 C7 -83.72(15) . . . . ?
C14 C10 C9 C8 160.17(12) . . . . ?
C14 C10 C1 C2 62.60(17) . . . . ?
C14 C10 C1 C7 -176.90(12) . . . . ?
C14 C10 C5 C4 -57.19(15) . . . . ?
C14 C10 C5 C6 -173.57(11) . . . . ?
C5 C4 C3 C2 1.6(2) . . . . ?
C5 C10 C9 C8 -70.77(14) . . . . ?
C5 C10 C1 C2 -61.87(14) . . . . ?
C5 C10 C1 C7 58.62(11) . . . . ?
C6 C7 C11 C12 11.6(2) . . . . ?
C6 C7 C11 C13 -170.50(13) . . . . ?
C15 C4 C3 C2 -179.42(14) . . . . ?
C15 C4 C5 C10 136.40(13) . . . . ?
C15 C4 C5 C6 -111.36(14) . . . . ?
C11 C7 C6 C5 153.80(12) . . . . ?

_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 2.772
_oxdiff_exptl_absorpt_empirical_full_min 0.395
####################################################################### 
# 
# 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_128-131
_database_code_depnum_ccdc_archive 'CCDC 2116449'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-06-15
_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         'C30 H38 O2'
_chemical_formula_sum            'C30 H38 O2'
_chemical_formula_weight         430.60
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2108(4)
_cell_length_b                   13.0566(5)
_cell_length_c                   21.0242(8)
_cell_angle_alpha                86.742(3)
_cell_angle_beta                 88.969(3)
_cell_angle_gamma                76.493(3)
_cell_volume                     2454.47(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7673
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4000
_cell_measurement_theta_min      3.9620
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85810
_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    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.792
_diffrn_reflns_theta_min         2.105
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  79.00   1.00    1.00    --   40.98 -99.00 -90.00   42
  2  ω     88.00 131.00   1.00    1.20    --  106.95 -61.00 -30.00   43
  3  ω     76.00 107.00   1.00    1.20    --  106.95 -95.00-120.00   31
  4  ω     67.00  95.00   1.00    1.20    --  106.95 -95.00-150.00   28
  5  ω     37.00  77.00   1.00    1.20    --  106.95 -61.00 -30.00   40
  6  ω     56.00 105.00   1.00    1.20    --  106.95 -95.00 -30.00   49
  7  ω     37.00 133.00   1.00    1.20    --  106.95 -45.00-150.00   96
  8  ω    117.00 178.00   1.00    1.20    --  106.95  30.00 -60.00   61
  9  ω    148.00 178.00   1.00    1.20    --  106.95  61.00-180.00   30
 10  ω     41.00 174.00   1.00    1.20    --  106.95   0.00 -90.00  133
 11  ω     74.00 119.00   1.00    1.20    --  106.95-125.00 150.00   45
 12  ω     34.00 134.00   1.00    1.20    --  106.95 -77.00 120.00  100
 13  ω     37.00  62.00   1.00    1.20    --  106.95-125.00 150.00   25
 14  ω     39.00 120.00   1.00    1.20    --  106.95 -45.00 120.00   81
 15  ω    122.00 178.00   1.00    1.20    --  106.95 125.00 150.00   56
 16  ω      6.00  42.00   1.00    1.00    --   40.98 -99.00-150.00   36
 17  ω    -22.00  65.00   1.00    1.00    --   40.98 -38.00-150.00   87
 18  ω    -69.00  29.00   1.00    1.00    --  -40.98  57.00 150.00   98
 19  ω   -112.00 -21.00   1.00    1.00    --  -40.98 -57.00   0.00   91
;
_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      0.0389116000
_diffrn_orient_matrix_UB_12      -0.0207036000
_diffrn_orient_matrix_UB_13      0.0712473000
_diffrn_orient_matrix_UB_21      0.1674802000
_diffrn_orient_matrix_UB_22      -0.0277907000
_diffrn_orient_matrix_UB_23      -0.0170551000
_diffrn_orient_matrix_UB_31      0.0050672000
_diffrn_orient_matrix_UB_32      0.1164798000
_diffrn_orient_matrix_UB_33      0.0044498000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7845
_reflns_number_total             9618
_reflns_odcompleteness_completeness 99.95
_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         0.272
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00037(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         9618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.024
_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)+(0.0529P)²+0.9587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1260
_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
2.a Ternary CH refined with riding coordinates:
 C2D(H2D), C5A(H5A), C2C(H2C), C1C(H1C), C1A(H1A), C1D(H1D), C2B(H2B),
 C1B(H1B), C5C(H5C), C2A(H2A), C5D(H5D), C5B(H5B)
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C9A(H9AA,H9AB), C6C(H6CA,H6CB), C9C(H9CA,H9CB), C9D(H9DA,
 H9DB), C6D(H6DA,H6DB), C6B(H6BA,H6BB), C9B(H9BA,H9BB)
2.c Aromatic/amide H refined with riding coordinates:
 C3C(H3C), C3D(H3D), C3B(H3B), C3A(H3A)
2.d Idealised Me refined as rotating group:
 C14C(H14G,H14H,H14I), C15A(H15A,H15B,H15C), C15C(H15G,H15H,H15I), C14A(H14A,
 H14B,H14C), C13C(H13G,H13H,H13I), C14D(H14J,H14K,H14L), C15D(H15J,H15K,H15L),
 C14B(H14D,H14E,H14F), C13A(H13A,H13B,H13C), C15B(H15D,H15E,H15F), C13B(H13D,
 H13E,H13F), C13D(H13J,H13K,H13L)
;
_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
O1A O 0.84888(14) 0.16693(9) 0.42543(6) 0.0306(3) Uani 1 1 d . . . . .
O1C O 0.63019(15) -0.10284(11) 0.56059(6) 0.0375(3) Uani 1 1 d . . . . .
O1D O 0.42667(15) -0.34710(11) 0.14032(6) 0.0365(3) Uani 1 1 d . . . . .
O1B O 1.06640(16) 0.38385(12) -0.02836(6) 0.0409(3) Uani 1 1 d . . . . .
C2D C 0.72819(17) -0.20924(12) 0.28893(7) 0.0200(3) Uani 1 1 d . . . . .
H2D H 0.635271 -0.156557 0.296086 0.024 Uiso 1 1 calc R U . . .
C3C C 0.93559(18) -0.33015(12) 0.35702(7) 0.0221(3) Uani 1 1 d . . . . .
H3C H 0.967947 -0.370055 0.322019 0.027 Uiso 1 1 calc R U . . .
C5A C 0.52039(18) 0.31660(12) 0.30634(7) 0.0228(3) Uani 1 1 d . . . . .
H5A H 0.434562 0.321664 0.335200 0.027 Uiso 1 1 calc R U . . .
C2C C 0.78066(17) -0.25929(12) 0.35602(7) 0.0195(3) Uani 1 1 d . . . . .
H2C H 0.713444 -0.305320 0.368162 0.023 Uiso 1 1 calc R U . . .
C3D C 0.83316(17) -0.14947(12) 0.25634(8) 0.0223(3) Uani 1 1 d . . . . .
H3D H 0.882782 -0.111849 0.281148 0.027 Uiso 1 1 calc R U . . .
C10A C 0.59692(17) 0.20052(12) 0.29424(7) 0.0221(3) Uani 1 1 d . . . . .
C8A C 0.77577(18) 0.18810(12) 0.37694(7) 0.0239(3) Uani 1 1 d . . . . .
C7A C 0.79100(17) 0.27036(12) 0.32443(7) 0.0211(3) Uani 1 1 d . . . . .
C14C C 1.00745(17) -0.10477(12) 0.39542(8) 0.0234(3) Uani 1 1 d . . . . .
H14G H 0.951834 -0.038404 0.377225 0.035 Uiso 1 1 calc R U . . .
H14H H 1.048896 -0.149921 0.361925 0.035 Uiso 1 1 calc R U . . .
H14I H 1.086675 -0.093256 0.421116 0.035 Uiso 1 1 calc R U . . .
C1C C 0.76033(17) -0.17769(12) 0.40815(7) 0.0194(3) Uani 1 1 d . . . . .
H1C H 0.692626 -0.111274 0.393442 0.023 Uiso 1 1 calc R U . . .
C1A C 0.74481(17) 0.21904(12) 0.26469(7) 0.0200(3) Uani 1 1 d . . . . .
H1A H 0.815046 0.151588 0.257771 0.024 Uiso 1 1 calc R U . . .
C1D C 0.68650(17) -0.28878(12) 0.24462(7) 0.0207(3) Uani 1 1 d . . . . .
H1D H 0.672587 -0.351673 0.269403 0.025 Uiso 1 1 calc R U . . .
C4A C 0.47658(18) 0.37598(12) 0.24303(8) 0.0229(3) Uani 1 1 d . . . . .
C4C C 1.02794(18) -0.33789(12) 0.40602(7) 0.0220(3) Uani 1 1 d . . . . .
C2B C 0.79784(18) 0.23570(12) 0.14359(7) 0.0219(3) Uani 1 1 d . . . . .
H2B H 0.896845 0.193361 0.155856 0.026 Uiso 1 1 calc R U . . .
C6A C 0.64738(18) 0.35807(12) 0.33618(7) 0.0240(3) Uani 1 1 d . . . . .
H6AA H 0.630181 0.367150 0.381385 0.029 Uiso 1 1 calc R U . . .
H6AB H 0.655128 0.424894 0.315454 0.029 Uiso 1 1 calc R U . . .
C3B C 0.71266(19) 0.15824(12) 0.12168(8) 0.0244(3) Uani 1 1 d . . . . .
H3B H 0.667941 0.120957 0.152121 0.029 Uiso 1 1 calc R U . . .
C1B C 0.82508(18) 0.31212(12) 0.08812(7) 0.0228(3) Uani 1 1 d . . . . .
H1B H 0.821770 0.382012 0.103633 0.027 Uiso 1 1 calc R U . . .
C5C C 0.97631(17) -0.27067(12) 0.46196(7) 0.0220(3) Uani 1 1 d . . . . .
H5C H 1.058125 -0.272568 0.491493 0.026 Uiso 1 1 calc R U . . .
C11C C 0.55608(18) -0.25050(13) 0.47332(7) 0.0245(3) Uani 1 1 d . . . . .
C4D C 0.85792(18) -0.14812(12) 0.19387(8) 0.0232(3) Uani 1 1 d . . . . .
C2A C 0.73243(17) 0.29352(12) 0.20394(7) 0.0216(3) Uani 1 1 d . . . . .
H2A H 0.796731 0.341621 0.211673 0.026 Uiso 1 1 calc R U . . .
C3A C 0.57718(18) 0.36291(12) 0.19615(8) 0.0227(3) Uani 1 1 d . . . . .
H3A H 0.550659 0.398084 0.156852 0.027 Uiso 1 1 calc R U . . .
C15A C 0.32477(19) 0.44850(14) 0.23798(9) 0.0297(4) Uani 1 1 d . . . . .
H15A H 0.250117 0.408356 0.244080 0.045 Uiso 1 1 calc R U . . .
H15B H 0.313381 0.484337 0.196577 0.045 Uiso 1 1 calc R U . . .
H15C H 0.313421 0.499343 0.270030 0.045 Uiso 1 1 calc R U . . .
C8C C 0.71086(18) -0.13125(13) 0.51582(8) 0.0251(3) Uani 1 1 d . . . . .
C10B C 0.72505(19) 0.32181(13) 0.02822(7) 0.0252(3) Uani 1 1 d . . . . .
C10D C 0.78940(18) -0.32056(12) 0.18615(7) 0.0233(3) Uani 1 1 d . . . . .
C7C C 0.70366(17) -0.22040(12) 0.47271(7) 0.0219(3) Uani 1 1 d . . . . .
C10C C 0.90456(17) -0.15652(12) 0.43654(7) 0.0208(3) Uani 1 1 d . . . . .
C7B C 0.97545(19) 0.26970(14) 0.05233(8) 0.0270(4) Uani 1 1 d . . . . .
C15C C 1.17867(19) -0.41220(13) 0.41021(8) 0.0279(4) Uani 1 1 d . . . . .
H15G H 1.196340 -0.452276 0.372788 0.042 Uiso 1 1 calc R U . . .
H15H H 1.182443 -0.459237 0.447251 0.042 Uiso 1 1 calc R U . . .
H15I H 1.253874 -0.372730 0.413267 0.042 Uiso 1 1 calc R U . . .
C9A C 0.65018(18) 0.14113(13) 0.35794(8) 0.0247(3) Uani 1 1 d . . . . .
H9AA H 0.570698 0.152417 0.389488 0.030 Uiso 1 1 calc R U . . .
H9AB H 0.684868 0.066028 0.352632 0.030 Uiso 1 1 calc R U . . .
C4B C 0.69936(19) 0.14150(13) 0.06048(8) 0.0264(3) Uani 1 1 d . . . . .
C14A C 0.50251(19) 0.14121(13) 0.25893(8) 0.0267(3) Uani 1 1 d . . . . .
H14A H 0.420124 0.131775 0.285409 0.040 Uiso 1 1 calc R U . . .
H14B H 0.562462 0.073521 0.248696 0.040 Uiso 1 1 calc R U . . .
H14C H 0.465328 0.180863 0.220385 0.040 Uiso 1 1 calc R U . . .
C6C C 0.84363(18) -0.30613(13) 0.49585(7) 0.0244(3) Uani 1 1 d . . . . .
H6CA H 0.853400 -0.307890 0.541787 0.029 Uiso 1 1 calc R U . . .
H6CB H 0.837686 -0.375447 0.483421 0.029 Uiso 1 1 calc R U . . .
C9C C 0.84157(18) -0.08871(13) 0.49272(8) 0.0246(3) Uani 1 1 d . . . . .
H9CA H 0.915531 -0.096261 0.525986 0.030 Uiso 1 1 calc R U . . .
H9CB H 0.809887 -0.014826 0.478803 0.030 Uiso 1 1 calc R U . . .
C13C C 0.42872(19) -0.16962(15) 0.44391(9) 0.0339(4) Uani 1 1 d . . . . .
H13G H 0.444315 -0.163067 0.398735 0.051 Uiso 1 1 calc R U . . .
H13H H 0.423188 -0.102855 0.461904 0.051 Uiso 1 1 calc R U . . .
H13I H 0.337107 -0.191134 0.452253 0.051 Uiso 1 1 calc R U . . .
C14D C 0.94873(19) -0.38424(13) 0.19539(8) 0.0286(4) Uani 1 1 d . . . . .
H14J H 0.948570 -0.447420 0.221060 0.043 Uiso 1 1 calc R U . . .
H14K H 1.005400 -0.343031 0.216307 0.043 Uiso 1 1 calc R U . . .
H14L H 0.992973 -0.402537 0.154666 0.043 Uiso 1 1 calc R U . . .
C7D C 0.54345(18) -0.23747(13) 0.20457(8) 0.0240(3) Uani 1 1 d . . . . .
C5D C 0.77515(18) -0.20903(13) 0.15379(7) 0.0240(3) Uani 1 1 d . . . . .
H5D H 0.811612 -0.212163 0.109699 0.029 Uiso 1 1 calc R U . . .
C5B C 0.76820(19) 0.20471(13) 0.01120(8) 0.0270(4) Uani 1 1 d . . . . .
H5B H 0.737062 0.195582 -0.032038 0.032 Uiso 1 1 calc R U . . .
C11A C 0.93875(19) 0.30025(14) 0.32351(8) 0.0270(4) Uani 1 1 d . . . . .
C9D C 0.6969(2) -0.38109(13) 0.14879(8) 0.0279(4) Uani 1 1 d . . . . .
H9DA H 0.719737 -0.377312 0.103616 0.034 Uiso 1 1 calc R U . . .
H9DB H 0.716809 -0.454598 0.163889 0.034 Uiso 1 1 calc R U . . .
C8B C 0.9646(2) 0.35336(15) -0.00248(8) 0.0315(4) Uani 1 1 d . . . . .
C15D C 0.96475(19) -0.09219(14) 0.16073(8) 0.0296(4) Uani 1 1 d . . . . .
H15J H 1.047697 -0.143079 0.144455 0.044 Uiso 1 1 calc R U . . .
H15K H 1.000210 -0.050356 0.190336 0.044 Uiso 1 1 calc R U . . .
H15L H 0.914874 -0.047246 0.126149 0.044 Uiso 1 1 calc R U . . .
C11B C 1.1172(2) 0.24992(16) 0.08972(9) 0.0336(4) Uani 1 1 d . . . . .
C8D C 0.5374(2) -0.32651(14) 0.16137(8) 0.0279(4) Uani 1 1 d . . . . .
C14B C 0.5580(2) 0.36706(14) 0.03313(8) 0.0297(4) Uani 1 1 d . . . . .
H14D H 0.514684 0.322517 0.061859 0.045 Uiso 1 1 calc R U . . .
H14E H 0.513790 0.370712 -0.008190 0.045 Uiso 1 1 calc R U . . .
H14F H 0.539778 0.436558 0.048839 0.045 Uiso 1 1 calc R U . . .
C6D C 0.60411(18) -0.16049(13) 0.15742(8) 0.0261(3) Uani 1 1 d . . . . .
H6DA H 0.558644 -0.156569 0.115824 0.031 Uiso 1 1 calc R U . . .
H6DB H 0.584187 -0.090239 0.173326 0.031 Uiso 1 1 calc R U . . .
C6B C 0.9411(2) 0.17510(14) 0.01786(8) 0.0295(4) Uani 1 1 d . . . . .
H6BA H 0.989300 0.168211 -0.023575 0.035 Uiso 1 1 calc R U . . .
H6BB H 0.974059 0.109471 0.043115 0.035 Uiso 1 1 calc R U . . .
C9B C 0.8009(2) 0.38782(14) -0.01898(8) 0.0314(4) Uani 1 1 d . . . . .
H9BA H 0.784160 0.373267 -0.062633 0.038 Uiso 1 1 calc R U . . .
H9BB H 0.763435 0.462642 -0.013468 0.038 Uiso 1 1 calc R U . . .
C11D C 0.40220(19) -0.19449(14) 0.24069(8) 0.0295(4) Uani 1 1 d . . . . .
C12C C 0.5360(2) -0.34092(15) 0.49999(9) 0.0332(4) Uani 1 1 d . . . . .
C13A C 1.0709(2) 0.21678(16) 0.30454(10) 0.0376(4) Uani 1 1 d . . . . .
H13A H 1.075406 0.153658 0.330935 0.056 Uiso 1 1 calc R U . . .
H13B H 1.160489 0.240932 0.309771 0.056 Uiso 1 1 calc R U . . .
H13C H 1.061490 0.202198 0.260757 0.056 Uiso 1 1 calc R U . . .
C15B C 0.6173(2) 0.06418(15) 0.03743(9) 0.0366(4) Uani 1 1 d . . . . .
H15D H 0.579606 0.029343 0.073305 0.055 Uiso 1 1 calc R U . . .
H15E H 0.684119 0.012830 0.013250 0.055 Uiso 1 1 calc R U . . .
H15F H 0.535579 0.100899 0.010975 0.055 Uiso 1 1 calc R U . . .
C12A C 0.9534(2) 0.39348(16) 0.34089(9) 0.0360(4) Uani 1 1 d . . . . .
C13B C 1.1422(2) 0.34230(17) 0.12377(10) 0.0404(5) Uani 1 1 d . . . . .
H13D H 1.128217 0.403037 0.094589 0.061 Uiso 1 1 calc R U . . .
H13E H 1.242027 0.326216 0.140132 0.061 Uiso 1 1 calc R U . . .
H13F H 1.072176 0.356739 0.158349 0.061 Uiso 1 1 calc R U . . .
C13D C 0.3491(2) -0.27392(17) 0.28399(11) 0.0439(5) Uani 1 1 d . . . . .
H13J H 0.425554 -0.305010 0.314357 0.066 Uiso 1 1 calc R U . . .
H13K H 0.327276 -0.327975 0.259212 0.066 Uiso 1 1 calc R U . . .
H13L H 0.260514 -0.239537 0.306066 0.066 Uiso 1 1 calc R U . . .
C12D C 0.3278(2) -0.09440(17) 0.23639(11) 0.0414(5) Uani 1 1 d . . . . .
C12B C 1.2158(3) 0.1582(2) 0.09341(13) 0.0558(6) Uani 1 1 d . . . . .
H12A H 0.868(2) 0.4484(17) 0.3559(11) 0.040(6) Uiso 1 1 d . . . . .
H12C H 1.200(3) 0.095(2) 0.0724(13) 0.064(8) Uiso 1 1 d . . . . .
H12G H 0.361(3) -0.0425(18) 0.2053(12) 0.048(6) Uiso 1 1 d . . . . .
H12D H 1.311(3) 0.150(2) 0.1177(15) 0.079(9) Uiso 1 1 d . . . . .
H12H H 0.235(3) -0.0690(18) 0.2614(11) 0.046(6) Uiso 1 1 d . . . . .
H12B H 1.053(3) 0.4080(17) 0.3408(11) 0.041(6) Uiso 1 1 d . . . . .
H12E H 0.440(2) -0.3571(15) 0.5000(10) 0.033(5) Uiso 1 1 d . . . . .
H12F H 0.621(3) -0.3946(18) 0.5191(11) 0.046(6) 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
O1A C8A 1.215(2) . ?
O1C C8C 1.209(2) . ?
O1D C8D 1.211(2) . ?
O1B C8B 1.210(2) . ?
C2D H2D 0.9800 . ?
C2D C2C 1.556(2) . ?
C2D C3D 1.510(2) . ?
C2D C1D 1.550(2) . ?
C3C H3C 0.9300 . ?
C3C C2C 1.508(2) . ?
C3C C4C 1.332(2) . ?
C5A H5A 0.9800 . ?
C5A C10A 1.548(2) . ?
C5A C4A 1.514(2) . ?
C5A C6A 1.554(2) . ?
C2C H2C 0.9800 . ?
C2C C1C 1.550(2) . ?
C3D H3D 0.9300 . ?
C3D C4D 1.329(2) . ?
C10A C1A 1.551(2) . ?
C10A C9A 1.537(2) . ?
C10A C14A 1.520(2) . ?
C8A C7A 1.524(2) . ?
C8A C9A 1.500(2) . ?
C7A C1A 1.567(2) . ?
C7A C6A 1.561(2) . ?
C7A C11A 1.500(2) . ?
C14C H14G 0.9600 . ?
C14C H14H 0.9600 . ?
C14C H14I 0.9600 . ?
C14C C10C 1.518(2) . ?
C1C H1C 0.9800 . ?
C1C C7C 1.565(2) . ?
C1C C10C 1.554(2) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.550(2) . ?
C1D H1D 0.9800 . ?
C1D C10D 1.554(2) . ?
C1D C7D 1.568(2) . ?
C4A C3A 1.331(2) . ?
C4A C15A 1.496(2) . ?
C4C C5C 1.511(2) . ?
C4C C15C 1.497(2) . ?
C2B H2B 0.9800 . ?
C2B C3B 1.512(2) . ?
C2B C1B 1.547(2) . ?
C2B C2A 1.553(2) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C3B H3B 0.9300 . ?
C3B C4B 1.330(2) . ?
C1B H1B 0.9800 . ?
C1B C10B 1.556(2) . ?
C1B C7B 1.563(2) . ?
C5C H5C 0.9800 . ?
C5C C10C 1.551(2) . ?
C5C C6C 1.553(2) . ?
C11C C7C 1.500(2) . ?
C11C C13C 1.499(2) . ?
C11C C12C 1.329(2) . ?
C4D C5D 1.519(2) . ?
C4D C15D 1.497(2) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.510(2) . ?
C3A H3A 0.9300 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C8C C7C 1.529(2) . ?
C8C C9C 1.501(2) . ?
C10B C5B 1.548(2) . ?
C10B C14B 1.518(2) . ?
C10B C9B 1.541(2) . ?
C10D C14D 1.518(2) . ?
C10D C5D 1.550(2) . ?
C10D C9D 1.541(2) . ?
C7C C6C 1.562(2) . ?
C10C C9C 1.540(2) . ?
C7B C8B 1.530(2) . ?
C7B C11B 1.499(2) . ?
C7B C6B 1.563(2) . ?
C15C H15G 0.9600 . ?
C15C H15H 0.9600 . ?
C15C H15I 0.9600 . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C4B C5B 1.510(2) . ?
C4B C15B 1.500(2) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C6C H6CA 0.9700 . ?
C6C H6CB 0.9700 . ?
C9C H9CA 0.9700 . ?
C9C H9CB 0.9700 . ?
C13C H13G 0.9600 . ?
C13C H13H 0.9600 . ?
C13C H13I 0.9600 . ?
C14D H14J 0.9600 . ?
C14D H14K 0.9600 . ?
C14D H14L 0.9600 . ?
C7D C8D 1.527(2) . ?
C7D C6D 1.560(2) . ?
C7D C11D 1.502(2) . ?
C5D H5D 0.9800 . ?
C5D C6D 1.557(2) . ?
C5B H5B 0.9800 . ?
C5B C6B 1.555(2) . ?
C11A C13A 1.497(3) . ?
C11A C12A 1.328(3) . ?
C9D H9DA 0.9700 . ?
C9D H9DB 0.9700 . ?
C9D C8D 1.502(2) . ?
C8B C9B 1.510(3) . ?
C15D H15J 0.9600 . ?
C15D H15K 0.9600 . ?
C15D H15L 0.9600 . ?
C11B C13B 1.501(3) . ?
C11B C12B 1.322(3) . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C6D H6DA 0.9700 . ?
C6D H6DB 0.9700 . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C11D C13D 1.502(3) . ?
C11D C12D 1.325(3) . ?
C12C H12E 0.96(2) . ?
C12C H12F 1.00(2) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C12A H12A 0.99(2) . ?
C12A H12B 0.98(2) . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C13D H13J 0.9600 . ?
C13D H13K 0.9600 . ?
C13D H13L 0.9600 . ?
C12D H12G 1.01(2) . ?
C12D H12H 1.00(2) . ?
C12B H12C 0.99(3) . ?
C12B H12D 1.01(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
C2C C2D H2D 105.7 . . ?
C3D C2D H2D 105.7 . . ?
C3D C2D C2C 114.16(12) . . ?
C3D C2D C1D 111.55(12) . . ?
C1D C2D H2D 105.7 . . ?
C1D C2D C2C 113.09(12) . . ?
C2C C3C H3C 118.7 . . ?
C4C C3C H3C 118.7 . . ?
C4C C3C C2C 122.65(14) . . ?
C10A C5A H5A 111.8 . . ?
C10A C5A C6A 102.97(12) . . ?
C4A C5A H5A 111.8 . . ?
C4A C5A C10A 108.98(12) . . ?
C4A C5A C6A 109.17(13) . . ?
C6A C5A H5A 111.8 . . ?
C2D C2C H2C 105.6 . . ?
C3C C2C C2D 114.22(12) . . ?
C3C C2C H2C 105.6 . . ?
C3C C2C C1C 111.65(12) . . ?
C1C C2C C2D 113.38(12) . . ?
C1C C2C H2C 105.6 . . ?
C2D C3D H3D 118.5 . . ?
C4D C3D C2D 123.08(14) . . ?
C4D C3D H3D 118.5 . . ?
C5A C10A C1A 98.26(12) . . ?
C9A C10A C5A 109.38(13) . . ?
C9A C10A C1A 102.03(12) . . ?
C14A C10A C5A 115.14(13) . . ?
C14A C10A C1A 120.52(13) . . ?
C14A C10A C9A 110.16(13) . . ?
O1A C8A C7A 126.44(15) . . ?
O1A C8A C9A 126.91(15) . . ?
C9A C8A C7A 106.63(13) . . ?
C8A C7A C1A 100.84(12) . . ?
C8A C7A C6A 100.85(12) . . ?
C6A C7A C1A 101.43(12) . . ?
C11A C7A C8A 114.08(13) . . ?
C11A C7A C1A 118.61(13) . . ?
C11A C7A C6A 118.13(13) . . ?
H14G C14C H14H 109.5 . . ?
H14G C14C H14I 109.5 . . ?
H14H C14C H14I 109.5 . . ?
C10C C14C H14G 109.5 . . ?
C10C C14C H14H 109.5 . . ?
C10C C14C H14I 109.5 . . ?
C2C C1C H1C 110.5 . . ?
C2C C1C C7C 112.24(12) . . ?
C2C C1C C10C 117.05(12) . . ?
C7C C1C H1C 110.5 . . ?
C10C C1C H1C 110.5 . . ?
C10C C1C C7C 95.07(11) . . ?
C10A C1A C7A 95.15(11) . . ?
C10A C1A H1A 110.5 . . ?
C7A C1A H1A 110.5 . . ?
C2A C1A C10A 117.08(13) . . ?
C2A C1A C7A 112.11(12) . . ?
C2A C1A H1A 110.5 . . ?
C2D C1D H1D 110.5 . . ?
C2D C1D C10D 117.35(13) . . ?
C2D C1D C7D 111.65(12) . . ?
C10D C1D H1D 110.5 . . ?
C10D C1D C7D 95.37(12) . . ?
C7D C1D H1D 110.5 . . ?
C3A C4A C5A 117.94(14) . . ?
C3A C4A C15A 124.25(15) . . ?
C15A C4A C5A 117.78(14) . . ?
C3C C4C C5C 118.42(14) . . ?
C3C C4C C15C 123.95(15) . . ?
C15C C4C C5C 117.59(14) . . ?
C3B C2B H2B 105.7 . . ?
C3B C2B C1B 111.46(13) . . ?
C3B C2B C2A 114.58(13) . . ?
C1B C2B H2B 105.7 . . ?
C1B C2B C2A 112.86(12) . . ?
C2A C2B H2B 105.7 . . ?
C5A C6A C7A 104.02(12) . . ?
C5A C6A H6AA 111.0 . . ?
C5A C6A H6AB 111.0 . . ?
C7A C6A H6AA 111.0 . . ?
C7A C6A H6AB 111.0 . . ?
H6AA C6A H6AB 109.0 . . ?
C2B C3B H3B 118.8 . . ?
C4B C3B C2B 122.40(15) . . ?
C4B C3B H3B 118.8 . . ?
C2B C1B H1B 110.4 . . ?
C2B C1B C10B 116.94(13) . . ?
C2B C1B C7B 112.47(13) . . ?
C10B C1B H1B 110.4 . . ?
C10B C1B C7B 95.26(12) . . ?
C7B C1B H1B 110.4 . . ?
C4C C5C H5C 111.7 . . ?
C4C C5C C10C 108.83(12) . . ?
C4C C5C C6C 109.59(13) . . ?
C10C C5C H5C 111.7 . . ?
C10C C5C C6C 102.94(12) . . ?
C6C C5C H5C 111.7 . . ?
C13C C11C C7C 115.65(14) . . ?
C12C C11C C7C 123.04(16) . . ?
C12C C11C C13C 121.27(16) . . ?
C3D C4D C5D 117.97(14) . . ?
C3D C4D C15D 124.06(15) . . ?
C15D C4D C5D 117.96(14) . . ?
C1A C2A C2B 113.20(12) . . ?
C1A C2A H2A 105.4 . . ?
C2B C2A H2A 105.4 . . ?
C3A C2A C1A 111.64(13) . . ?
C3A C2A C2B 114.85(13) . . ?
C3A C2A H2A 105.4 . . ?
C4A C3A C2A 122.91(15) . . ?
C4A C3A H3A 118.5 . . ?
C2A C3A H3A 118.5 . . ?
C4A C15A H15A 109.5 . . ?
C4A C15A H15B 109.5 . . ?
C4A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O1C C8C C7C 126.88(15) . . ?
O1C C8C C9C 126.96(15) . . ?
C9C C8C C7C 106.12(13) . . ?
C5B C10B C1B 98.01(13) . . ?
C14B C10B C1B 120.02(13) . . ?
C14B C10B C5B 114.05(14) . . ?
C14B C10B C9B 112.14(14) . . ?
C9B C10B C1B 101.59(13) . . ?
C9B C10B C5B 109.52(13) . . ?
C14D C10D C1D 120.44(13) . . ?
C14D C10D C5D 114.65(14) . . ?
C14D C10D C9D 111.20(13) . . ?
C5D C10D C1D 98.32(12) . . ?
C9D C10D C1D 101.39(12) . . ?
C9D C10D C5D 109.37(13) . . ?
C11C C7C C1C 118.13(13) . . ?
C11C C7C C8C 114.55(13) . . ?
C11C C7C C6C 117.80(13) . . ?
C8C C7C C1C 100.84(12) . . ?
C8C C7C C6C 100.79(12) . . ?
C6C C7C C1C 101.93(12) . . ?
C14C C10C C1C 120.55(13) . . ?
C14C C10C C5C 114.48(13) . . ?
C14C C10C C9C 110.99(12) . . ?
C5C C10C C1C 98.18(12) . . ?
C9C C10C C1C 101.74(12) . . ?
C9C C10C C5C 109.52(13) . . ?
C1B C7B C6B 101.66(13) . . ?
C8B C7B C1B 100.90(14) . . ?
C8B C7B C6B 101.83(13) . . ?
C11B C7B C1B 117.89(14) . . ?
C11B C7B C8B 114.26(15) . . ?
C11B C7B C6B 117.67(15) . . ?
C4C C15C H15G 109.5 . . ?
C4C C15C H15H 109.5 . . ?
C4C C15C H15I 109.5 . . ?
H15G C15C H15H 109.5 . . ?
H15G C15C H15I 109.5 . . ?
H15H C15C H15I 109.5 . . ?
C10A C9A H9AA 111.0 . . ?
C10A C9A H9AB 111.0 . . ?
C8A C9A C10A 103.76(12) . . ?
C8A C9A H9AA 111.0 . . ?
C8A C9A H9AB 111.0 . . ?
H9AA C9A H9AB 109.0 . . ?
C3B C4B C5B 118.53(15) . . ?
C3B C4B C15B 123.55(16) . . ?
C15B C4B C5B 117.91(14) . . ?
C10A C14A H14A 109.5 . . ?
C10A C14A H14B 109.5 . . ?
C10A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C5C C6C C7C 103.91(12) . . ?
C5C C6C H6CA 111.0 . . ?
C5C C6C H6CB 111.0 . . ?
C7C C6C H6CA 111.0 . . ?
C7C C6C H6CB 111.0 . . ?
H6CA C6C H6CB 109.0 . . ?
C8C C9C C10C 104.10(12) . . ?
C8C C9C H9CA 110.9 . . ?
C8C C9C H9CB 110.9 . . ?
C10C C9C H9CA 110.9 . . ?
C10C C9C H9CB 110.9 . . ?
H9CA C9C H9CB 109.0 . . ?
C11C C13C H13G 109.5 . . ?
C11C C13C H13H 109.5 . . ?
C11C C13C H13I 109.5 . . ?
H13G C13C H13H 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C10D C14D H14J 109.5 . . ?
C10D C14D H14K 109.5 . . ?
C10D C14D H14L 109.5 . . ?
H14J C14D H14K 109.5 . . ?
H14J C14D H14L 109.5 . . ?
H14K C14D H14L 109.5 . . ?
C8D C7D C1D 100.89(13) . . ?
C8D C7D C6D 101.10(13) . . ?
C6D C7D C1D 101.29(12) . . ?
C11D C7D C1D 117.26(13) . . ?
C11D C7D C8D 115.35(14) . . ?
C11D C7D C6D 118.14(14) . . ?
C4D C5D C10D 108.51(13) . . ?
C4D C5D H5D 111.9 . . ?
C4D C5D C6D 109.82(13) . . ?
C10D C5D H5D 111.9 . . ?
C10D C5D C6D 102.53(12) . . ?
C6D C5D H5D 111.9 . . ?
C10B C5B H5B 111.7 . . ?
C10B C5B C6B 103.35(13) . . ?
C4B C5B C10B 108.12(13) . . ?
C4B C5B H5B 111.7 . . ?
C4B C5B C6B 109.82(14) . . ?
C6B C5B H5B 111.7 . . ?
C13A C11A C7A 116.02(15) . . ?
C12A C11A C7A 122.37(17) . . ?
C12A C11A C13A 121.55(17) . . ?
C10D C9D H9DA 110.8 . . ?
C10D C9D H9DB 110.8 . . ?
H9DA C9D H9DB 108.9 . . ?
C8D C9D C10D 104.60(13) . . ?
C8D C9D H9DA 110.8 . . ?
C8D C9D H9DB 110.8 . . ?
O1B C8B C7B 127.19(18) . . ?
O1B C8B C9B 127.01(18) . . ?
C9B C8B C7B 105.77(14) . . ?
C4D C15D H15J 109.5 . . ?
C4D C15D H15K 109.5 . . ?
C4D C15D H15L 109.5 . . ?
H15J C15D H15K 109.5 . . ?
H15J C15D H15L 109.5 . . ?
H15K C15D H15L 109.5 . . ?
C7B C11B C13B 115.50(17) . . ?
C12B C11B C7B 123.60(18) . . ?
C12B C11B C13B 120.91(19) . . ?
O1D C8D C7D 126.98(17) . . ?
O1D C8D C9D 127.12(16) . . ?
C9D C8D C7D 105.87(13) . . ?
C10B C14B H14D 109.5 . . ?
C10B C14B H14E 109.5 . . ?
C10B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C7D C6D H6DA 110.8 . . ?
C7D C6D H6DB 110.8 . . ?
C5D C6D C7D 104.51(13) . . ?
C5D C6D H6DA 110.8 . . ?
C5D C6D H6DB 110.8 . . ?
H6DA C6D H6DB 108.9 . . ?
C7B C6B H6BA 111.0 . . ?
C7B C6B H6BB 111.0 . . ?
C5B C6B C7B 103.67(13) . . ?
C5B C6B H6BA 111.0 . . ?
C5B C6B H6BB 111.0 . . ?
H6BA C6B H6BB 109.0 . . ?
C10B C9B H9BA 110.9 . . ?
C10B C9B H9BB 110.9 . . ?
C8B C9B C10B 104.22(14) . . ?
C8B C9B H9BA 110.9 . . ?
C8B C9B H9BB 110.9 . . ?
H9BA C9B H9BB 108.9 . . ?
C7D C11D C13D 114.98(15) . . ?
C12D C11D C7D 124.11(17) . . ?
C12D C11D C13D 120.91(18) . . ?
C11C C12C H12E 120.7(12) . . ?
C11C C12C H12F 120.9(13) . . ?
H12E C12C H12F 118.3(17) . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C4B C15B H15D 109.5 . . ?
C4B C15B H15E 109.5 . . ?
C4B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C11A C12A H12A 122.8(13) . . ?
C11A C12A H12B 119.0(13) . . ?
H12A C12A H12B 118.1(18) . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11D C13D H13J 109.5 . . ?
C11D C13D H13K 109.5 . . ?
C11D C13D H13L 109.5 . . ?
H13J C13D H13K 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?
C11D C12D H12G 120.4(13) . . ?
C11D C12D H12H 121.6(13) . . ?
H12G C12D H12H 117.9(19) . . ?
C11B C12B H12C 122.3(16) . . ?
C11B C12B H12D 120.3(17) . . ?
H12C C12B H12D 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C8A C7A C1A 149.02(16) . . . . ?
O1A C8A C7A C6A -106.96(18) . . . . ?
O1A C8A C7A C11A 20.7(2) . . . . ?
O1A C8A C9A C10A 177.81(16) . . . . ?
O1C C8C C7C C1C 148.56(17) . . . . ?
O1C C8C C7C C11C 20.6(2) . . . . ?
O1C C8C C7C C6C -106.92(19) . . . . ?
O1C C8C C9C C10C 178.04(17) . . . . ?
O1B C8B C9B C10B 178.79(17) . . . . ?
C2D C2C C1C C7C 139.80(13) . . . . ?
C2D C2C C1C C10C -111.79(15) . . . . ?
C2D C3D C4D C5D 0.6(2) . . . . ?
C2D C3D C4D C15D -178.10(15) . . . . ?
C2D C1D C10D C14D 67.01(19) . . . . ?
C2D C1D C10D C5D -58.08(16) . . . . ?
C2D C1D C10D C9D -169.88(13) . . . . ?
C2D C1D C7D C8D 174.38(12) . . . . ?
C2D C1D C7D C6D 70.59(15) . . . . ?
C2D C1D C7D C11D -59.49(18) . . . . ?
C3C C2C C1C C7C -89.47(15) . . . . ?
C3C C2C C1C C10C 18.95(18) . . . . ?
C3C C4C C5C C10C -45.79(19) . . . . ?
C3C C4C C5C C6C 66.08(18) . . . . ?
C5A C10A C1A C7A 59.59(13) . . . . ?
C5A C10A C1A C2A -58.47(15) . . . . ?
C5A C10A C9A C8A -69.34(15) . . . . ?
C5A C4A C3A C2A -1.1(2) . . . . ?
C2C C2D C3D C4D 144.05(15) . . . . ?
C2C C2D C1D C10D -111.83(15) . . . . ?
C2C C2D C1D C7D 139.59(13) . . . . ?
C2C C3C C4C C5C -1.6(2) . . . . ?
C2C C3C C4C C15C 176.15(14) . . . . ?
C2C C1C C7C C11C -60.44(18) . . . . ?
C2C C1C C7C C8C 173.97(12) . . . . ?
C2C C1C C7C C6C 70.36(15) . . . . ?
C2C C1C C10C C14C 66.10(18) . . . . ?
C2C C1C C10C C5C -58.71(15) . . . . ?
C2C C1C C10C C9C -170.71(13) . . . . ?
C3D C2D C2C C3C -54.65(17) . . . . ?
C3D C2D C2C C1C 74.79(16) . . . . ?
C3D C2D C1D C10D 18.47(18) . . . . ?
C3D C2D C1D C7D -90.11(15) . . . . ?
C3D C4D C5D C10D -47.56(19) . . . . ?
C3D C4D C5D C6D 63.77(19) . . . . ?
C10A C5A C4A C3A -46.23(19) . . . . ?
C10A C5A C4A C15A 135.88(14) . . . . ?
C10A C5A C6A C7A 12.01(15) . . . . ?
C10A C1A C2A C2B -112.66(15) . . . . ?
C10A C1A C2A C3A 18.79(18) . . . . ?
C8A C7A C1A C10A 51.34(13) . . . . ?
C8A C7A C1A C2A 173.34(12) . . . . ?
C8A C7A C6A C5A -78.37(14) . . . . ?
C8A C7A C11A C13A 68.70(18) . . . . ?
C8A C7A C11A C12A -108.66(19) . . . . ?
C7A C8A C9A C10A -0.47(16) . . . . ?
C7A C1A C2A C2B 138.89(13) . . . . ?
C7A C1A C2A C3A -89.66(15) . . . . ?
C14C C10C C9C C8C 163.29(13) . . . . ?
C1C C7C C6C C5C 24.24(15) . . . . ?
C1C C10C C9C C8C 33.82(15) . . . . ?
C1A C10A C9A C8A 34.00(15) . . . . ?
C1A C7A C6A C5A 25.17(14) . . . . ?
C1A C7A C11A C13A -49.9(2) . . . . ?
C1A C7A C11A C12A 132.76(17) . . . . ?
C1A C2A C3A C4A 15.1(2) . . . . ?
C1D C2D C2C C3C 74.32(16) . . . . ?
C1D C2D C2C C1C -156.24(12) . . . . ?
C1D C2D C3D C4D 14.3(2) . . . . ?
C1D C10D C5D C4D 70.82(15) . . . . ?
C1D C10D C5D C6D -45.32(14) . . . . ?
C1D C10D C9D C8D 33.38(16) . . . . ?
C1D C7D C8D O1D 148.22(17) . . . . ?
C1D C7D C8D C9D -33.45(15) . . . . ?
C1D C7D C6D C5D 24.47(15) . . . . ?
C1D C7D C11D C13D -59.6(2) . . . . ?
C1D C7D C11D C12D 119.7(2) . . . . ?
C4A C5A C10A C1A 70.75(15) . . . . ?
C4A C5A C10A C9A 176.67(13) . . . . ?
C4A C5A C10A C14A -58.67(17) . . . . ?
C4A C5A C6A C7A -103.67(14) . . . . ?
C4C C3C C2C C2D 145.64(15) . . . . ?
C4C C3C C2C C1C 15.3(2) . . . . ?
C4C C5C C10C C14C -58.50(17) . . . . ?
C4C C5C C10C C1C 70.52(14) . . . . ?
C4C C5C C10C C9C 176.13(12) . . . . ?
C4C C5C C6C C7C -102.64(14) . . . . ?
C2B C3B C4B C5B -1.8(2) . . . . ?
C2B C3B C4B C15B 179.18(16) . . . . ?
C2B C1B C10B C5B -59.10(16) . . . . ?
C2B C1B C10B C14B 64.73(19) . . . . ?
C2B C1B C10B C9B -171.02(13) . . . . ?
C2B C1B C7B C8B 174.45(13) . . . . ?
C2B C1B C7B C11B -60.43(19) . . . . ?
C2B C1B C7B C6B 69.79(16) . . . . ?
C2B C2A C3A C4A 145.71(15) . . . . ?
C6A C5A C10A C1A -45.07(14) . . . . ?
C6A C5A C10A C9A 60.86(15) . . . . ?
C6A C5A C10A C14A -174.48(13) . . . . ?
C6A C5A C4A C3A 65.53(18) . . . . ?
C6A C5A C4A C15A -112.36(15) . . . . ?
C6A C7A C1A C10A -52.21(13) . . . . ?
C6A C7A C1A C2A 69.79(15) . . . . ?
C6A C7A C11A C13A -173.08(14) . . . . ?
C6A C7A C11A C12A 9.6(2) . . . . ?
C3B C2B C1B C10B 18.24(19) . . . . ?
C3B C2B C1B C7B -90.51(16) . . . . ?
C3B C2B C2A C1A 66.73(17) . . . . ?
C3B C2B C2A C3A -63.11(18) . . . . ?
C3B C4B C5B C10B -46.5(2) . . . . ?
C3B C4B C5B C6B 65.6(2) . . . . ?
C1B C2B C3B C4B 16.3(2) . . . . ?
C1B C2B C2A C1A -164.27(13) . . . . ?
C1B C2B C2A C3A 65.89(17) . . . . ?
C1B C10B C5B C4B 71.43(15) . . . . ?
C1B C10B C5B C6B -44.95(14) . . . . ?
C1B C10B C9B C8B 33.39(16) . . . . ?
C1B C7B C8B O1B 147.84(17) . . . . ?
C1B C7B C8B C9B -33.79(16) . . . . ?
C1B C7B C11B C13B -55.5(2) . . . . ?
C1B C7B C11B C12B 124.5(2) . . . . ?
C1B C7B C6B C5B 25.19(16) . . . . ?
C5C C10C C9C C8C -69.35(16) . . . . ?
C11C C7C C6C C5C 155.24(13) . . . . ?
C4D C5D C6D C7D -102.57(14) . . . . ?
C2A C2B C3B C4B 145.97(16) . . . . ?
C2A C2B C1B C10B -112.35(15) . . . . ?
C2A C2B C1B C7B 138.89(13) . . . . ?
C15A C4A C3A C2A 176.60(14) . . . . ?
C8C C7C C6C C5C -79.41(14) . . . . ?
C10B C1B C7B C8B 52.41(14) . . . . ?
C10B C1B C7B C11B 177.54(15) . . . . ?
C10B C1B C7B C6B -52.24(14) . . . . ?
C10B C5B C6B C7B 12.10(16) . . . . ?
C10D C1D C7D C8D 52.12(13) . . . . ?
C10D C1D C7D C6D -51.67(13) . . . . ?
C10D C1D C7D C11D 178.25(14) . . . . ?
C10D C5D C6D C7D 12.63(15) . . . . ?
C10D C9D C8D O1D 178.61(17) . . . . ?
C10D C9D C8D C7D 0.29(17) . . . . ?
C7C C1C C10C C14C -175.74(13) . . . . ?
C7C C1C C10C C5C 59.45(12) . . . . ?
C7C C1C C10C C9C -52.55(13) . . . . ?
C7C C8C C9C C10C -0.05(16) . . . . ?
C10C C1C C7C C11C 177.59(13) . . . . ?
C10C C1C C7C C8C 52.00(13) . . . . ?
C10C C1C C7C C6C -51.61(13) . . . . ?
C10C C5C C6C C7C 13.04(15) . . . . ?
C7B C1B C10B C5B 59.42(13) . . . . ?
C7B C1B C10B C14B -176.75(14) . . . . ?
C7B C1B C10B C9B -52.50(14) . . . . ?
C7B C8B C9B C10B 0.40(17) . . . . ?
C15C C4C C5C C10C 136.28(14) . . . . ?
C15C C4C C5C C6C -111.85(15) . . . . ?
C9A C10A C1A C7A -52.36(13) . . . . ?
C9A C10A C1A C2A -170.42(12) . . . . ?
C9A C8A C7A C1A -32.69(15) . . . . ?
C9A C8A C7A C6A 71.33(14) . . . . ?
C9A C8A C7A C11A -160.98(13) . . . . ?
C4B C5B C6B C7B -103.07(15) . . . . ?
C14A C10A C1A C7A -174.69(14) . . . . ?
C14A C10A C1A C2A 67.25(19) . . . . ?
C14A C10A C9A C8A 163.16(13) . . . . ?
C6C C5C C10C C14C -174.72(13) . . . . ?
C6C C5C C10C C1C -45.70(13) . . . . ?
C6C C5C C10C C9C 59.91(15) . . . . ?
C9C C8C C7C C1C -33.35(15) . . . . ?
C9C C8C C7C C11C -161.31(14) . . . . ?
C9C C8C C7C C6C 71.17(15) . . . . ?
C13C C11C C7C C1C -50.3(2) . . . . ?
C13C C11C C7C C8C 68.33(19) . . . . ?
C13C C11C C7C C6C -173.41(14) . . . . ?
C14D C10D C5D C4D -58.26(17) . . . . ?
C14D C10D C5D C6D -174.41(13) . . . . ?
C14D C10D C9D C8D 162.61(13) . . . . ?
C7D C1D C10D C14D -175.23(14) . . . . ?
C7D C1D C10D C5D 59.68(13) . . . . ?
C7D C1D C10D C9D -52.12(14) . . . . ?
C5D C10D C9D C8D -69.76(16) . . . . ?
C5B C10B C9B C8B -69.54(16) . . . . ?
C11A C7A C1A C10A 176.63(14) . . . . ?
C11A C7A C1A C2A -61.37(18) . . . . ?
C11A C7A C6A C5A 156.63(13) . . . . ?
C9D C10D C5D C4D 176.07(13) . . . . ?
C9D C10D C5D C6D 59.92(15) . . . . ?
C8B C7B C11B C13B 62.7(2) . . . . ?
C8B C7B C11B C12B -117.3(2) . . . . ?
C8B C7B C6B C5B -78.72(15) . . . . ?
C15D C4D C5D C10D 131.17(15) . . . . ?
C15D C4D C5D C6D -117.50(16) . . . . ?
C11B C7B C8B O1B 20.3(2) . . . . ?
C11B C7B C8B C9B -161.33(14) . . . . ?
C11B C7B C6B C5B 155.55(14) . . . . ?
C8D C7D C6D C5D -79.15(14) . . . . ?
C8D C7D C11D C13D 59.0(2) . . . . ?
C8D C7D C11D C12D -121.63(19) . . . . ?
C14B C10B C5B C4B -56.60(18) . . . . ?
C14B C10B C5B C6B -172.98(13) . . . . ?
C14B C10B C9B C8B 162.79(14) . . . . ?
C6D C7D C8D O1D -107.84(19) . . . . ?
C6D C7D C8D C9D 70.49(15) . . . . ?
C6D C7D C11D C13D 178.67(15) . . . . ?
C6D C7D C11D C12D -2.0(3) . . . . ?
C6B C7B C8B O1B -107.65(19) . . . . ?
C6B C7B C8B C9B 70.73(16) . . . . ?
C6B C7B C11B C13B -177.90(15) . . . . ?
C6B C7B C11B C12B 2.1(3) . . . . ?
C9B C10B C5B C4B 176.80(14) . . . . ?
C9B C10B C5B C6B 60.43(16) . . . . ?
C11D C7D C8D O1D 20.8(2) . . . . ?
C11D C7D C8D C9D -160.84(14) . . . . ?
C11D C7D C6D C5D 154.00(14) . . . . ?
C12C C11C C7C C1C 132.09(17) . . . . ?
C12C C11C C7C C8C -109.32(19) . . . . ?
C12C C11C C7C C6C 8.9(2) . . . . ?
C15B C4B C5B C10B 132.52(16) . . . . ?
C15B C4B C5B C6B -115.38(17) . . . . ?

_olex2_date_sample_data_collection 2019-07-05
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_20-21-2
_database_code_depnum_ccdc_archive 'CCDC 2116455'
loop_
_audit_author_name
_audit_author_address
'Mu Chen'
;JNU
China
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-07-07
_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 H18 O2'
_chemical_formula_sum            'C15 H18 O2'
_chemical_formula_weight         230.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8307(15)
_cell_length_b                   8.8487(13)
_cell_length_c                   9.8739(17)
_cell_angle_alpha                68.029(15)
_cell_angle_beta                 70.418(18)
_cell_angle_gamma                82.359(14)
_cell_volume                     597.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4620
_cell_measurement_theta_min      5.3770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42682
_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    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3915
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.880
_diffrn_reflns_theta_min         5.081
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00 111.00   1.00    1.00    --   40.98  57.00   0.00   98
  2  ω     82.00 115.00   1.00    1.00    --  106.95  77.00 -60.00   33
  3  ω    118.00 172.00   1.00    1.00    --  106.95  77.00 -60.00   54
  4  ω     96.00 168.00   1.00    1.00    --  106.95 125.00-180.00   72
  5  ω     85.00 163.00   1.00    1.00    --  106.95  61.00-120.00   78
  6  ω     85.00 178.00   1.00    1.00    --  106.95  45.00   0.00   93
  7  ω    113.00 159.00   1.00    1.00    --  106.95 125.00 150.00   46
  8  ω     81.00 173.00   1.00    1.00    --  106.95  77.00 -90.00   92
  9  ω     75.00 100.00   1.00    1.00    --  106.95 -94.00  90.00   25
 10  ω     43.00  76.00   1.00    1.00    --   40.98 -99.00 120.00   33
 11  ω     37.00 121.00   1.00    1.00    --  106.95-125.00  30.00   84
 12  ω     35.00 106.00   1.00    1.00    --  106.95 -94.00 120.00   71
 13  ω     39.00  66.00   1.00    1.00    --   40.98  37.00-150.00   27
 14  ω     40.00 134.00   1.00    1.00    --  106.95 -77.00-180.00   94
 15  ω    -34.00  53.00   1.00    1.00    --   40.98 -77.00-120.00   87
 16  ω    -65.00  32.00   1.00    1.00    --  -40.98  57.00 120.00   97
 17  ω     91.00 116.00   1.00    3.00    --  106.95-111.00-120.00   25
 18  ω     87.00 100.00   1.00    3.00    --  106.95  61.00  90.00   13
;
_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      -0.0792241000
_diffrn_orient_matrix_UB_12      -0.1725709000
_diffrn_orient_matrix_UB_13      0.0899998000
_diffrn_orient_matrix_UB_21      -0.0397557000
_diffrn_orient_matrix_UB_22      0.0008212000
_diffrn_orient_matrix_UB_23      -0.1428775000
_diffrn_orient_matrix_UB_31      0.1890728000
_diffrn_orient_matrix_UB_32      -0.0739314000
_diffrn_orient_matrix_UB_33      -0.0530315000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1575
_reflns_number_total             2320
_reflns_odcompleteness_completeness 98.97
_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         0.756
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.1180
_refine_ls_restrained_S_all      1.132
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3018
_refine_ls_wR_factor_ref         0.3357
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4903(3) 0.6903(3) 0.7109(3) 0.0336(7) Uani 1 1 d . . . . .
O2 O 0.4219(3) 0.8567(3) 0.2989(3) 0.0320(7) Uani 1 1 d . . . . .
C2 C 0.6078(4) 0.7050(4) 0.5877(4) 0.0251(8) Uani 1 1 d . . . . .
C9 C 0.6859(4) 0.9386(4) 0.3191(4) 0.0258(8) Uani 1 1 d . . . . .
H9 H 0.677401 1.057797 0.279982 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6941(4) 0.8629(4) 0.4845(4) 0.0259(8) Uani 1 1 d . . . . .
H1 H 0.690540 0.940968 0.534389 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6715(4) 0.5620(4) 0.5422(4) 0.0261(8) Uani 1 1 d . . . . .
H3 H 0.610427 0.464254 0.602154 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8129(5) 0.5655(4) 0.4187(4) 0.0261(8) Uani 1 1 d . . . . .
C6 C 0.9046(5) 0.7544(4) 0.1468(4) 0.0273(8) Uani 1 1 d . . . . .
H6A H 0.971089 0.852804 0.075429 0.033 Uiso 1 1 calc R U . . .
H6B H 0.958544 0.665404 0.111319 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5877(4) 0.8550(4) 0.2600(4) 0.0266(8) Uani 1 1 d . . . . .
C5 C 0.9194(4) 0.7179(4) 0.3077(4) 0.0251(8) Uani 1 1 d . . . . .
H5 H 1.047129 0.696369 0.302282 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6410(5) 0.7292(4) 0.0618(4) 0.0269(8) Uani 1 1 d . . . . .
C7 C 0.7071(4) 0.7765(4) 0.1500(4) 0.0249(8) Uani 1 1 d . . . . .
C10 C 0.8599(5) 0.8723(4) 0.3474(4) 0.0254(8) Uani 1 1 d . . . . .
C14 C 1.0086(5) 0.9878(4) 0.3058(4) 0.0308(9) Uani 1 1 d . . . . .
H14A H 1.077399 1.013617 0.199268 0.046 Uiso 1 1 calc R U . . .
H14B H 1.086724 0.937762 0.367799 0.046 Uiso 1 1 calc R U . . .
H14C H 0.956806 1.085850 0.323628 0.046 Uiso 1 1 calc R U . . .
C15 C 0.8686(5) 0.4146(4) 0.3790(4) 0.0301(9) Uani 1 1 d . . . . .
H15A H 0.814323 0.321202 0.466397 0.045 Uiso 1 1 calc R U . . .
H15B H 0.998158 0.403182 0.350864 0.045 Uiso 1 1 calc R U . . .
H15C H 0.828926 0.422713 0.294482 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4483(5) 0.7578(5) 0.0550(5) 0.0346(9) Uani 1 1 d . . . . .
H13A H 0.373791 0.668719 0.133047 0.052 Uiso 1 1 calc R U . . .
H13B H 0.446981 0.765181 -0.044105 0.052 Uiso 1 1 calc R U . . .
H13C H 0.402212 0.857456 0.071956 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7540(5) 0.6405(5) -0.0416(4) 0.0346(9) Uani 1 1 d . . . . .
H12A H 0.878348 0.638846 -0.045375 0.052 Uiso 1 1 calc R U . . .
H12B H 0.744433 0.695028 -0.143056 0.052 Uiso 1 1 calc R U . . .
H12C H 0.711597 0.530725 -0.002416 0.052 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 1.228(4) . ?
O2 C8 1.225(4) . ?
C2 C1 1.474(5) . ?
C2 C3 1.469(4) . ?
C9 H9 0.9800 . ?
C9 C1 1.536(5) . ?
C9 C8 1.501(4) . ?
C9 C10 1.483(4) . ?
C1 H1 0.9800 . ?
C1 C10 1.514(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.338(5) . ?
C4 C5 1.515(5) . ?
C4 C15 1.500(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.539(5) . ?
C6 C7 1.524(4) . ?
C8 C7 1.500(4) . ?
C5 H5 0.9800 . ?
C5 C10 1.532(4) . ?
C11 C7 1.354(5) . ?
C11 C13 1.516(5) . ?
C11 C12 1.500(5) . ?
C10 C14 1.500(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
O1 C2 C1 121.7(3) . . ?
O1 C2 C3 120.2(3) . . ?
C3 C2 C1 118.1(3) . . ?
C1 C9 H9 114.7 . . ?
C8 C9 H9 114.7 . . ?
C8 C9 C1 120.9(3) . . ?
C10 C9 H9 114.7 . . ?
C10 C9 C1 60.2(2) . . ?
C10 C9 C8 120.8(3) . . ?
C2 C1 C9 120.5(3) . . ?
C2 C1 H1 115.3 . . ?
C2 C1 C10 120.5(3) . . ?
C9 C1 H1 115.3 . . ?
C10 C1 C9 58.2(2) . . ?
C10 C1 H1 115.3 . . ?
C2 C3 H3 118.4 . . ?
C4 C3 C2 123.3(3) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 123.8(3) . . ?
C3 C4 C15 120.1(3) . . ?
C15 C4 C5 116.0(3) . . ?
H6A C6 H6B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 C5 110.8(3) . . ?
O2 C8 C9 120.6(3) . . ?
O2 C8 C7 124.2(3) . . ?
C7 C8 C9 115.2(3) . . ?
C4 C5 C6 109.0(3) . . ?
C4 C5 H5 108.2 . . ?
C4 C5 C10 115.8(3) . . ?
C6 C5 H5 108.2 . . ?
C10 C5 C6 107.3(3) . . ?
C10 C5 H5 108.2 . . ?
C7 C11 C13 125.1(3) . . ?
C7 C11 C12 122.7(3) . . ?
C12 C11 C13 112.2(3) . . ?
C8 C7 C6 114.9(3) . . ?
C11 C7 C6 123.6(3) . . ?
C11 C7 C8 121.5(3) . . ?
C9 C10 C1 61.6(2) . . ?
C9 C10 C5 112.0(3) . . ?
C9 C10 C14 119.2(3) . . ?
C1 C10 C5 118.0(3) . . ?
C14 C10 C1 119.1(3) . . ?
C14 C10 C5 115.7(3) . . ?
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 . . ?
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 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 C1 C9 -122.0(3) . . . . ?
O1 C2 C1 C10 169.4(3) . . . . ?
O1 C2 C3 C4 -172.0(3) . . . . ?
O2 C8 C7 C6 -166.4(3) . . . . ?
O2 C8 C7 C11 13.4(5) . . . . ?
C2 C1 C10 C9 109.1(3) . . . . ?
C2 C1 C10 C5 7.9(5) . . . . ?
C2 C1 C10 C14 -141.4(3) . . . . ?
C2 C3 C4 C5 -2.6(5) . . . . ?
C2 C3 C4 C15 -179.5(3) . . . . ?
C9 C1 C10 C5 -101.2(3) . . . . ?
C9 C1 C10 C14 109.5(3) . . . . ?
C9 C8 C7 C6 15.2(4) . . . . ?
C9 C8 C7 C11 -165.0(3) . . . . ?
C1 C2 C3 C4 5.6(5) . . . . ?
C1 C9 C8 O2 75.4(4) . . . . ?
C1 C9 C8 C7 -106.2(3) . . . . ?
C1 C9 C10 C5 110.9(3) . . . . ?
C1 C9 C10 C14 -109.4(3) . . . . ?
C3 C2 C1 C9 60.4(4) . . . . ?
C3 C2 C1 C10 -8.2(5) . . . . ?
C3 C4 C5 C6 -119.0(3) . . . . ?
C3 C4 C5 C10 2.0(5) . . . . ?
C4 C5 C10 C9 -73.1(4) . . . . ?
C4 C5 C10 C1 -4.6(4) . . . . ?
C4 C5 C10 C14 145.7(3) . . . . ?
C6 C5 C10 C9 48.8(4) . . . . ?
C6 C5 C10 C1 117.4(3) . . . . ?
C6 C5 C10 C14 -92.3(3) . . . . ?
C8 C9 C1 C2 1.0(4) . . . . ?
C8 C9 C1 C10 110.1(3) . . . . ?
C8 C9 C10 C1 -110.3(3) . . . . ?
C8 C9 C10 C5 0.6(5) . . . . ?
C8 C9 C10 C14 140.3(3) . . . . ?
C5 C6 C7 C8 34.4(4) . . . . ?
C5 C6 C7 C11 -145.4(3) . . . . ?
C7 C6 C5 C4 58.3(3) . . . . ?
C7 C6 C5 C10 -67.8(3) . . . . ?
C10 C9 C1 C2 -109.1(3) . . . . ?
C10 C9 C8 O2 146.8(3) . . . . ?
C10 C9 C8 C7 -34.7(5) . . . . ?
C15 C4 C5 C6 58.0(4) . . . . ?
C15 C4 C5 C10 179.1(3) . . . . ?
C13 C11 C7 C6 -176.3(3) . . . . ?
C13 C11 C7 C8 3.9(6) . . . . ?
C12 C11 C7 C6 3.9(6) . . . . ?
C12 C11 C7 C8 -175.8(3) . . . . ?

_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 3.348
_oxdiff_exptl_absorpt_empirical_full_min 0.185
