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

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

data_cl02036a
_database_code_depnum_ccdc_archive 'CCDC 2124205'
loop_
_audit_author_name
_audit_author_address
'Zhang Qunlong'
;Nankai University
China
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 O3, H O0.5'
_chemical_formula_sum            'C23 H33 O3.50'
_chemical_formula_weight         365.49
_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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   36.4809(3)
_cell_length_b                   14.42217(12)
_cell_length_c                   7.54283(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3968.54(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11500
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7560
_cell_measurement_theta_min      6.3090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18252
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.877
_diffrn_reflns_theta_min         6.601
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.992
_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    -66.00   3.00   0.50    0.50    --    0.00 -38.00 138.00  138
  2  ω    109.00 134.00   0.50    0.50    --  101.30  38.00 -66.00   50
  3  ω     45.00  70.00   0.50    0.50    --  101.30 -38.00 138.00   50
  4  ω    -36.00  39.00   0.50    0.50    --    0.00  82.00 -60.00  150
  5  ω     67.00 127.00   0.50    0.50    --  101.30 -38.00-180.00  120
  6  ω     18.00 128.00   0.50    0.50    --  101.30 -57.00  30.00  220
  7  ω     14.00  62.00   0.50    0.50    --  101.30 -38.00-180.00   96
  8  ω     12.00 138.00   0.50    0.50    --  101.30 -82.00 150.00  252
  9  ω     12.00 127.00   0.50    0.50    --  101.30 -38.00 -30.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0287598000
_diffrn_orient_matrix_UB_12      0.0659441000
_diffrn_orient_matrix_UB_13      -0.0803332000
_diffrn_orient_matrix_UB_21      0.0307607000
_diffrn_orient_matrix_UB_22      0.0667442000
_diffrn_orient_matrix_UB_23      -0.0575318000
_diffrn_orient_matrix_UB_31      0.0030458000
_diffrn_orient_matrix_UB_32      -0.0510771000
_diffrn_orient_matrix_UB_33      -0.1787769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3753
_reflns_number_total             4011
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.316
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+1.7929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1041
_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 Free rotating group:
 O10(H10)
2.b Ternary CH refined with riding coordinates:
 C00I(H00O), C00K(H00R)
2.c Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C008(H00F,H00G), C00G(H00J,H00K), C00J(H00P,H00Q), C00N(H00V,
 H00W)
2.d Aromatic/amide H refined with riding coordinates:
 C00C(H00H), C00D(H00I)
2.e X=CH2 refined with riding coordinates:
 C00Q(H00Z,HA)
2.f Idealised Me refined as rotating group:
 C007(H00C,H00D,H00E), C00H(H00L,H00M,H00N), C00L(H00S,H00T,H00U), C00P(H00X,
 H00Y,H), C00R(H00,HB,HC)
2.g Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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
O001 O 0.47161(2) 0.65341(6) 0.23073(11) 0.02204(19) Uani 1 1 d . . . . .
O10 O 0.2500 0.2500 0.64814(16) 0.0258(3) Uani 1 2 d S T P . .
H10 H 0.2645 0.2800 0.5813 0.039 Uiso 1 1 d G . . . .
O003 O 0.32411(2) 0.62856(6) 0.39446(13) 0.0288(2) Uani 1 1 d . . . . .
O004 O 0.29503(2) 0.32118(6) 0.39860(12) 0.0279(2) Uani 1 1 d . . . . .
H004 H 0.2818 0.3019 0.3189 0.042 Uiso 1 1 calc GR . . . .
C005 C 0.42136(3) 0.57721(8) 0.36151(15) 0.0181(2) Uani 1 1 d . . . . .
C006 C 0.44389(3) 0.49974(8) 0.43572(15) 0.0194(2) Uani 1 1 d . . . . .
H00A H 0.4663 0.5230 0.4889 0.023 Uiso 1 1 calc R . . . .
H00B H 0.4501 0.4551 0.3444 0.023 Uiso 1 1 calc R . . . .
C007 C 0.43125(3) 0.35544(8) 0.60879(16) 0.0225(3) Uani 1 1 d . . . . .
H00C H 0.4239 0.3175 0.5103 0.034 Uiso 1 1 calc GR . . . .
H00D H 0.4203 0.3321 0.7155 0.034 Uiso 1 1 calc GR . . . .
H00E H 0.4575 0.3541 0.6200 0.034 Uiso 1 1 calc GR . . . .
C008 C 0.37191(3) 0.40164(8) 0.33726(15) 0.0197(2) Uani 1 1 d . . . . .
H00F H 0.3919 0.4062 0.2530 0.024 Uiso 1 1 calc R . . . .
H00G H 0.3713 0.3386 0.3821 0.024 Uiso 1 1 calc R . . . .
C009 C 0.43429(3) 0.65111(8) 0.25937(15) 0.0192(2) Uani 1 1 d . . . . .
C00A C 0.38441(3) 0.56650(8) 0.40405(15) 0.0182(2) Uani 1 1 d . . . . .
C00B C 0.36009(3) 0.63519(8) 0.34340(16) 0.0210(2) Uani 1 1 d . . . . .
C00C C 0.40959(3) 0.71512(8) 0.19331(16) 0.0218(2) Uani 1 1 d . . . . .
H00H H 0.4176 0.7631 0.1205 0.026 Uiso 1 1 calc R . . . .
C00D C 0.37273(3) 0.70692(8) 0.23702(16) 0.0227(3) Uani 1 1 d . . . . .
H00I H 0.3562 0.7505 0.1940 0.027 Uiso 1 1 calc R . . . .
C00E C 0.41851(3) 0.45590(8) 0.57749(15) 0.0183(2) Uani 1 1 d . . . . .
C00F C 0.37883(3) 0.46951(7) 0.49298(15) 0.0177(2) Uani 1 1 d . . . . .
C00G C 0.33583(3) 0.42320(9) 0.24363(16) 0.0232(3) Uani 1 1 d . . . . .
H00J H 0.3371 0.4849 0.1930 0.028 Uiso 1 1 calc R . . . .
H00K H 0.3323 0.3795 0.1473 0.028 Uiso 1 1 calc R . . . .
C00H C 0.34626(3) 0.35829(8) 0.71423(17) 0.0234(3) Uani 1 1 d . . . . .
H00L H 0.3440 0.3131 0.6215 0.035 Uiso 1 1 calc GR . . . .
H00M H 0.3258 0.3530 0.7938 0.035 Uiso 1 1 calc GR . . . .
H00N H 0.3686 0.3478 0.7782 0.035 Uiso 1 1 calc GR . . . .
C00I C 0.30314(3) 0.41785(9) 0.36857(17) 0.0246(3) Uani 1 1 d . . . . .
H00O H 0.2820 0.4465 0.3100 0.030 Uiso 1 1 calc R . . . .
C00J C 0.35282(3) 0.52703(8) 0.78264(16) 0.0223(3) Uani 1 1 d . . . . .
H00P H 0.3517 0.5895 0.7352 0.027 Uiso 1 1 calc R . . . .
H00Q H 0.3333 0.5204 0.8691 0.027 Uiso 1 1 calc R . . . .
C00K C 0.42228(3) 0.51687(8) 0.74766(15) 0.0205(2) Uani 1 1 d . . . . .
H00R H 0.4237 0.5812 0.7062 0.025 Uiso 1 1 calc R . . . .
C00L C 0.45759(3) 0.49955(9) 0.85209(17) 0.0272(3) Uani 1 1 d . . . . .
H00S H 0.4565 0.4395 0.9068 0.041 Uiso 1 1 calc GR . . . .
H00T H 0.4602 0.5462 0.9419 0.041 Uiso 1 1 calc GR . . . .
H00U H 0.4782 0.5020 0.7731 0.041 Uiso 1 1 calc GR . . . .
C00M C 0.30899(3) 0.46551(8) 0.54570(17) 0.0222(3) Uani 1 1 d . . . . .
C00N C 0.38957(3) 0.51278(9) 0.87395(16) 0.0243(3) Uani 1 1 d . . . . .
H00V H 0.3895 0.4530 0.9327 0.029 Uiso 1 1 calc R . . . .
H00W H 0.3926 0.5600 0.9643 0.029 Uiso 1 1 calc R . . . .
C00O C 0.34685(3) 0.45730(8) 0.63190(16) 0.0194(2) Uani 1 1 d . . . . .
C00P C 0.48463(4) 0.72550(9) 0.11815(17) 0.0277(3) Uani 1 1 d . . . . .
H00X H 0.4729 0.7210 0.0046 0.042 Uiso 1 1 calc GR . . . .
H00Y H 0.5107 0.7196 0.1036 0.042 Uiso 1 1 calc GR . . . .
H H 0.4791 0.7846 0.1704 0.042 Uiso 1 1 calc GR . . . .
C00Q C 0.28012(3) 0.50367(9) 0.62449(18) 0.0282(3) Uani 1 1 d . . . . .
H00Z H 0.2572 0.5007 0.5710 0.034 Uiso 1 1 calc R . . . .
HA H 0.2829 0.5334 0.7331 0.034 Uiso 1 1 calc R . . . .
C00R C 0.29810(4) 0.68699(11) 0.3130(2) 0.0416(4) Uani 1 1 d . . . . .
H00 H 0.2987 0.6778 0.1870 0.062 Uiso 1 1 calc GR . . . .
HB H 0.3038 0.7505 0.3395 0.062 Uiso 1 1 calc GR . . . .
HC H 0.2741 0.6725 0.3571 0.062 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.3789(14) . ?
O001 C00P 1.4240(14) . ?
O10 H10 0.8503 . ?
O003 C00B 1.3714(14) . ?
O003 C00R 1.4100(16) . ?
O004 H004 0.8200 . ?
O004 C00I 1.4432(15) . ?
C005 C006 1.4958(15) . ?
C005 C009 1.3971(15) . ?
C005 C00A 1.3941(16) . ?
C006 H00A 0.9700 . ?
C006 H00B 0.9700 . ?
C006 C00E 1.5494(15) . ?
C007 H00C 0.9600 . ?
C007 H00D 0.9600 . ?
C007 H00E 0.9600 . ?
C007 C00E 1.5399(15) . ?
C008 H00F 0.9700 . ?
C008 H00G 0.9700 . ?
C008 C00F 1.5497(15) . ?
C008 C00G 1.5257(16) . ?
C009 C00C 1.3830(16) . ?
C00A C00B 1.4064(16) . ?
C00A C00F 1.5645(15) . ?
C00B C00D 1.3880(17) . ?
C00C H00H 0.9300 . ?
C00C C00D 1.3896(17) . ?
C00D H00I 0.9300 . ?
C00E C00F 1.5938(15) . ?
C00E C00K 1.5619(16) . ?
C00F C00O 1.5781(15) . ?
C00G H00J 0.9700 . ?
C00G H00K 0.9700 . ?
C00G C00I 1.5219(17) . ?
C00H H00L 0.9600 . ?
C00H H00M 0.9600 . ?
C00H H00N 0.9600 . ?
C00H C00O 1.5573(16) . ?
C00I H00O 0.9800 . ?
C00I C00M 1.5176(17) . ?
C00J H00P 0.9700 . ?
C00J H00Q 0.9700 . ?
C00J C00N 1.5214(17) . ?
C00J C00O 1.5334(16) . ?
C00K H00R 0.9800 . ?
C00K C00L 1.5306(16) . ?
C00K C00N 1.5279(16) . ?
C00L H00S 0.9600 . ?
C00L H00T 0.9600 . ?
C00L H00U 0.9600 . ?
C00M C00O 1.5312(16) . ?
C00M C00Q 1.3285(17) . ?
C00N H00V 0.9700 . ?
C00N H00W 0.9700 . ?
C00P H00X 0.9600 . ?
C00P H00Y 0.9600 . ?
C00P H 0.9600 . ?
C00Q H00Z 0.9300 . ?
C00Q HA 0.9300 . ?
C00R H00 0.9600 . ?
C00R HB 0.9600 . ?
C00R HC 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
C009 O001 C00P 116.14(9) . . ?
C00B O003 C00R 118.69(10) . . ?
C00I O004 H004 109.5 . . ?
C009 C005 C006 126.21(10) . . ?
C00A C005 C006 111.24(10) . . ?
C00A C005 C009 122.54(10) . . ?
C005 C006 H00A 111.0 . . ?
C005 C006 H00B 111.0 . . ?
C005 C006 C00E 103.57(9) . . ?
H00A C006 H00B 109.0 . . ?
C00E C006 H00A 111.0 . . ?
C00E C006 H00B 111.0 . . ?
H00C C007 H00D 109.5 . . ?
H00C C007 H00E 109.5 . . ?
H00D C007 H00E 109.5 . . ?
C00E C007 H00C 109.5 . . ?
C00E C007 H00D 109.5 . . ?
C00E C007 H00E 109.5 . . ?
H00F C008 H00G 108.0 . . ?
C00F C008 H00F 109.4 . . ?
C00F C008 H00G 109.4 . . ?
C00G C008 H00F 109.4 . . ?
C00G C008 H00G 109.4 . . ?
C00G C008 C00F 111.26(9) . . ?
O001 C009 C005 115.98(10) . . ?
O001 C009 C00C 124.81(10) . . ?
C00C C009 C005 119.20(11) . . ?
C005 C00A C00B 117.19(10) . . ?
C005 C00A C00F 108.88(9) . . ?
C00B C00A C00F 133.40(10) . . ?
O003 C00B C00A 117.61(10) . . ?
O003 C00B C00D 122.16(10) . . ?
C00D C00B C00A 120.24(11) . . ?
C009 C00C H00H 120.4 . . ?
C009 C00C C00D 119.23(11) . . ?
C00D C00C H00H 120.4 . . ?
C00B C00D C00C 121.46(11) . . ?
C00B C00D H00I 119.3 . . ?
C00C C00D H00I 119.3 . . ?
C006 C00E C00F 102.50(9) . . ?
C006 C00E C00K 106.55(9) . . ?
C007 C00E C006 108.01(9) . . ?
C007 C00E C00F 116.84(9) . . ?
C007 C00E C00K 112.16(9) . . ?
C00K C00E C00F 109.84(9) . . ?
C008 C00F C00A 105.13(9) . . ?
C008 C00F C00E 111.92(9) . . ?
C008 C00F C00O 108.20(9) . . ?
C00A C00F C00E 99.40(8) . . ?
C00A C00F C00O 118.73(9) . . ?
C00O C00F C00E 113.09(9) . . ?
C008 C00G H00J 109.1 . . ?
C008 C00G H00K 109.1 . . ?
H00J C00G H00K 107.9 . . ?
C00I C00G C008 112.27(10) . . ?
C00I C00G H00J 109.1 . . ?
C00I C00G H00K 109.1 . . ?
H00L C00H H00M 109.5 . . ?
H00L C00H H00N 109.5 . . ?
H00M C00H H00N 109.5 . . ?
C00O C00H H00L 109.5 . . ?
C00O C00H H00M 109.5 . . ?
C00O C00H H00N 109.5 . . ?
O004 C00I C00G 107.86(10) . . ?
O004 C00I H00O 108.4 . . ?
O004 C00I C00M 109.16(10) . . ?
C00G C00I H00O 108.4 . . ?
C00M C00I C00G 114.33(10) . . ?
C00M C00I H00O 108.4 . . ?
H00P C00J H00Q 107.9 . . ?
C00N C00J H00P 109.2 . . ?
C00N C00J H00Q 109.2 . . ?
C00N C00J C00O 111.86(10) . . ?
C00O C00J H00P 109.2 . . ?
C00O C00J H00Q 109.2 . . ?
C00E C00K H00R 106.0 . . ?
C00L C00K C00E 113.90(10) . . ?
C00L C00K H00R 106.0 . . ?
C00N C00K C00E 114.95(9) . . ?
C00N C00K H00R 106.0 . . ?
C00N C00K C00L 109.27(10) . . ?
C00K C00L H00S 109.5 . . ?
C00K C00L H00T 109.5 . . ?
C00K C00L H00U 109.5 . . ?
H00S C00L H00T 109.5 . . ?
H00S C00L H00U 109.5 . . ?
H00T C00L H00U 109.5 . . ?
C00I C00M C00O 117.75(10) . . ?
C00Q C00M C00I 118.04(11) . . ?
C00Q C00M C00O 123.85(12) . . ?
C00J C00N C00K 113.63(10) . . ?
C00J C00N H00V 108.8 . . ?
C00J C00N H00W 108.8 . . ?
C00K C00N H00V 108.8 . . ?
C00K C00N H00W 108.8 . . ?
H00V C00N H00W 107.7 . . ?
C00H C00O C00F 112.16(9) . . ?
C00J C00O C00F 108.31(9) . . ?
C00J C00O C00H 107.91(10) . . ?
C00M C00O C00F 112.10(9) . . ?
C00M C00O C00H 103.17(9) . . ?
C00M C00O C00J 113.10(9) . . ?
O001 C00P H00X 109.5 . . ?
O001 C00P H00Y 109.5 . . ?
O001 C00P H 109.5 . . ?
H00X C00P H00Y 109.5 . . ?
H00X C00P H 109.5 . . ?
H00Y C00P H 109.5 . . ?
C00M C00Q H00Z 120.0 . . ?
C00M C00Q HA 120.0 . . ?
H00Z C00Q HA 120.0 . . ?
O003 C00R H00 109.5 . . ?
O003 C00R HB 109.5 . . ?
O003 C00R HC 109.5 . . ?
H00 C00R HB 109.5 . . ?
H00 C00R HC 109.5 . . ?
HB C00R HC 109.5 . . ?


_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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_ky0508-1
_database_code_depnum_ccdc_archive 'CCDC 2141326'
loop_
_audit_author_name
_audit_author_address
'Zhang Qunlong'
;Nankai University
China
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 O3'
_chemical_formula_sum            'C21 H26 O3'
_chemical_formula_weight         326.42
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.46953(17)
_cell_length_b                   17.2423(4)
_cell_length_c                   25.6766(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3306.93(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4177
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.3120
_cell_measurement_theta_min      6.6530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9856
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        66.998
_diffrn_reflns_theta_max         66.998
_diffrn_reflns_theta_min         6.685
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  31.00   1.00    1.00    --    0.00  26.00 -21.00   26
  2  ω    -81.00 -28.00   1.00    1.00    --    0.00 -26.00 175.00   53
  3  ω    106.00 131.00   1.00    3.00    --  101.30  26.00 -21.00   25
  4  ω     23.00  87.00   1.00    3.00    --  101.30 -26.00 175.00   64
  5  ω    -36.00  38.00   1.00    1.00    --    0.00  82.00 -60.00   74
  6  ω     83.00 180.00   1.00    3.00    --  101.30  82.00 120.00   97
  7  ω     12.00 133.00   1.00    3.00    --  101.30 -77.00  30.00  121
  8  ω     76.00 101.00   1.00    3.00    --  101.30  38.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1608594000
_diffrn_orient_matrix_UB_12      0.0555587000
_diffrn_orient_matrix_UB_13      0.0044463000
_diffrn_orient_matrix_UB_21      -0.1175453000
_diffrn_orient_matrix_UB_22      -0.0673102000
_diffrn_orient_matrix_UB_23      0.0196558000
_diffrn_orient_matrix_UB_31      0.0534680000
_diffrn_orient_matrix_UB_32      0.0190636000
_diffrn_orient_matrix_UB_33      0.0565114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2488
_reflns_number_total             2827
_reflns_odcompleteness_completeness 95.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.183
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+1.3546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1073
_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:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C), C00F(H00D,H00E), C00H(H00F,H00H), C00K(H00M,H00N), C00L(H00O,
 H00P)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I)
2.d Idealised Me refined as rotating group:
 C00J(H00J,H00K,H00L), C00M(H00Q,H00R,H00S), C00N(H00T,H00U,H00V), C00O(H00W,
 H00X,H00Y)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
O001 O 0.30634(14) 0.29151(5) 0.66581(4) 0.0205(2) Uani 1 1 d . . . . .
O002 O 0.57380(16) 0.58949(6) 0.69265(4) 0.0268(3) Uani 1 1 d . . . . .
H002 H 0.5333 0.6100 0.7190 0.040 Uiso 1 1 calc GR . . . .
O003 O 0.48586(16) 0.13876(6) 0.70727(4) 0.0326(3) Uani 1 1 d . . . . .
C004 C 0.54064(19) 0.38545(8) 0.65685(5) 0.0173(3) Uani 1 1 d . . . . .
C005 C 0.3755(2) 0.36464(8) 0.67532(5) 0.0180(3) Uani 1 1 d . . . . .
C006 C 0.5080(2) 0.51505(8) 0.68847(5) 0.0207(3) Uani 1 1 d . . . . .
C007 C 0.77677(19) 0.39381(8) 0.59571(5) 0.0189(3) Uani 1 1 d . . . . .
C008 C 0.6088(2) 0.46006(8) 0.66189(5) 0.0190(3) Uani 1 1 d . . . . .
C009 C 0.55714(19) 0.26873(8) 0.60062(5) 0.0187(3) Uani 1 1 d . . . . .
C00A C 0.6624(2) 0.41956(8) 0.54781(6) 0.0208(3) Uani 1 1 d . . . . .
H00A H 0.5640 0.4511 0.5615 0.025 Uiso 1 1 calc R . . . .
C00B C 0.4247(2) 0.23395(8) 0.64159(5) 0.0203(3) Uani 1 1 d . . . . .
C00C C 0.66897(19) 0.33221(8) 0.62914(5) 0.0175(3) Uani 1 1 d . . . . .
C00D C 0.5299(2) 0.20036(8) 0.68818(6) 0.0218(3) Uani 1 1 d . . . . .
C00E C 0.7846(2) 0.46497(8) 0.63360(6) 0.0215(3) Uani 1 1 d . . . . .
H00B H 0.8845 0.4606 0.6576 0.026 Uiso 1 1 calc R . . . .
H00C H 0.7948 0.5133 0.6145 0.026 Uiso 1 1 calc R . . . .
C00F C 0.4541(2) 0.30519(8) 0.55499(5) 0.0214(3) Uani 1 1 d . . . . .
H00D H 0.3962 0.2645 0.5350 0.026 Uiso 1 1 calc R . . . .
H00E H 0.3615 0.3391 0.5685 0.026 Uiso 1 1 calc R . . . .
C00G C 0.2744(2) 0.41909(8) 0.70245(5) 0.0219(3) Uani 1 1 d . . . . .
H00G H 0.1630 0.4059 0.7160 0.026 Uiso 1 1 calc R . . . .
C00H C 0.5770(2) 0.35140(8) 0.51937(6) 0.0227(3) Uani 1 1 d . . . . .
H00F H 0.5088 0.3706 0.4899 0.027 Uiso 1 1 calc R . . . .
H00H H 0.6703 0.3176 0.5061 0.027 Uiso 1 1 calc R . . . .
C00I C 0.3427(2) 0.49368(8) 0.70892(5) 0.0234(3) Uani 1 1 d . . . . .
H00I H 0.2762 0.5301 0.7274 0.028 Uiso 1 1 calc R . . . .
C00J C 0.9653(2) 0.36820(9) 0.57943(6) 0.0246(3) Uani 1 1 d . . . . .
H00J H 0.9567 0.3296 0.5526 0.037 Uiso 1 1 calc GR . . . .
H00K H 1.0267 0.3469 0.6090 0.037 Uiso 1 1 calc GR . . . .
H00L H 1.0306 0.4121 0.5665 0.037 Uiso 1 1 calc GR . . . .
C00K C 0.6749(2) 0.24953(8) 0.71114(5) 0.0235(3) Uani 1 1 d . . . . .
H00M H 0.7533 0.2167 0.7316 0.028 Uiso 1 1 calc R . . . .
H00N H 0.6208 0.2868 0.7346 0.028 Uiso 1 1 calc R . . . .
C00L C 0.7881(2) 0.29348(8) 0.67108(5) 0.0221(3) Uani 1 1 d . . . . .
H00O H 0.8704 0.2577 0.6544 0.027 Uiso 1 1 calc R . . . .
H00P H 0.8582 0.3329 0.6887 0.027 Uiso 1 1 calc R . . . .
C00M C 0.6754(2) 0.20167(8) 0.58037(6) 0.0256(4) Uani 1 1 d . . . . .
H00Q H 0.7153 0.1708 0.6092 0.038 Uiso 1 1 calc GR . . . .
H00R H 0.7772 0.2226 0.5624 0.038 Uiso 1 1 calc GR . . . .
H00S H 0.6070 0.1700 0.5569 0.038 Uiso 1 1 calc GR . . . .
C00N C 0.2953(2) 0.17435(9) 0.61981(6) 0.0276(4) Uani 1 1 d . . . . .
H00T H 0.2172 0.1567 0.6470 0.041 Uiso 1 1 calc GR . . . .
H00U H 0.3613 0.1312 0.6061 0.041 Uiso 1 1 calc GR . . . .
H00V H 0.2255 0.1975 0.5925 0.041 Uiso 1 1 calc GR . . . .
C00O C 0.7648(2) 0.47080(9) 0.50921(6) 0.0288(4) Uani 1 1 d . . . . .
H00W H 0.8213 0.5126 0.5276 0.043 Uiso 1 1 calc GR . . . .
H00X H 0.6829 0.4915 0.4840 0.043 Uiso 1 1 calc GR . . . .
H00Y H 0.8542 0.4404 0.4918 0.043 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.3845(17) . ?
O001 C00B 1.4676(17) . ?
O002 H002 0.8200 . ?
O002 C006 1.3786(18) . ?
O003 C00D 1.2153(18) . ?
C004 C005 1.369(2) . ?
C004 C008 1.390(2) . ?
C004 C00C 1.5059(19) . ?
C005 C00G 1.392(2) . ?
C006 C008 1.390(2) . ?
C006 C00I 1.391(2) . ?
C007 C00A 1.562(2) . ?
C007 C00C 1.5854(19) . ?
C007 C00E 1.5671(19) . ?
C007 C00J 1.5340(19) . ?
C008 C00E 1.503(2) . ?
C009 C00B 1.5635(19) . ?
C009 C00C 1.5595(19) . ?
C009 C00F 1.5364(19) . ?
C009 C00M 1.5450(19) . ?
C00A H00A 0.9800 . ?
C00A C00H 1.524(2) . ?
C00A C00O 1.532(2) . ?
C00B C00D 1.544(2) . ?
C00B C00N 1.518(2) . ?
C00C C00L 1.5484(19) . ?
C00D C00K 1.496(2) . ?
C00E H00B 0.9700 . ?
C00E H00C 0.9700 . ?
C00F H00D 0.9700 . ?
C00F H00E 0.9700 . ?
C00F C00H 1.522(2) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.394(2) . ?
C00H H00F 0.9700 . ?
C00H H00H 0.9700 . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00J H00L 0.9600 . ?
C00K H00M 0.9700 . ?
C00K H00N 0.9700 . ?
C00K C00L 1.532(2) . ?
C00L H00O 0.9700 . ?
C00L H00P 0.9700 . ?
C00M H00Q 0.9600 . ?
C00M H00R 0.9600 . ?
C00M H00S 0.9600 . ?
C00N H00T 0.9600 . ?
C00N H00U 0.9600 . ?
C00N H00V 0.9600 . ?
C00O H00W 0.9600 . ?
C00O H00X 0.9600 . ?
C00O H00Y 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
C005 O001 C00B 117.76(11) . . ?
C006 O002 H002 109.5 . . ?
C005 C004 C008 122.71(13) . . ?
C005 C004 C00C 125.26(13) . . ?
C008 C004 C00C 112.03(13) . . ?
O001 C005 C00G 119.99(14) . . ?
C004 C005 O001 120.92(13) . . ?
C004 C005 C00G 119.06(13) . . ?
O002 C006 C008 118.69(14) . . ?
O002 C006 C00I 122.26(13) . . ?
C008 C006 C00I 119.04(13) . . ?
C00A C007 C00C 109.83(11) . . ?
C00A C007 C00E 106.66(11) . . ?
C00E C007 C00C 101.96(11) . . ?
C00J C007 C00A 111.68(12) . . ?
C00J C007 C00C 114.90(11) . . ?
C00J C007 C00E 111.11(12) . . ?
C004 C008 C006 118.61(14) . . ?
C004 C008 C00E 109.10(12) . . ?
C006 C008 C00E 132.24(13) . . ?
C00C C009 C00B 106.98(11) . . ?
C00F C009 C00B 110.67(12) . . ?
C00F C009 C00C 109.84(11) . . ?
C00F C009 C00M 109.63(12) . . ?
C00M C009 C00B 107.51(11) . . ?
C00M C009 C00C 112.16(12) . . ?
C007 C00A H00A 106.6 . . ?
C00H C00A C007 112.78(11) . . ?
C00H C00A H00A 106.6 . . ?
C00H C00A C00O 110.09(12) . . ?
C00O C00A C007 113.61(12) . . ?
C00O C00A H00A 106.6 . . ?
O001 C00B C009 114.01(11) . . ?
O001 C00B C00D 103.42(11) . . ?
O001 C00B C00N 103.31(12) . . ?
C00D C00B C009 110.07(12) . . ?
C00N C00B C009 114.51(11) . . ?
C00N C00B C00D 110.83(12) . . ?
C004 C00C C007 99.83(11) . . ?
C004 C00C C009 107.98(12) . . ?
C004 C00C C00L 107.47(11) . . ?
C009 C00C C007 119.20(11) . . ?
C00L C00C C007 111.94(12) . . ?
C00L C00C C009 109.38(11) . . ?
O003 C00D C00B 120.17(14) . . ?
O003 C00D C00K 122.16(14) . . ?
C00K C00D C00B 117.45(12) . . ?
C007 C00E H00B 111.2 . . ?
C007 C00E H00C 111.2 . . ?
C008 C00E C007 102.90(11) . . ?
C008 C00E H00B 111.2 . . ?
C008 C00E H00C 111.2 . . ?
H00B C00E H00C 109.1 . . ?
C009 C00F H00D 109.3 . . ?
C009 C00F H00E 109.3 . . ?
H00D C00F H00E 107.9 . . ?
C00H C00F C009 111.73(12) . . ?
C00H C00F H00D 109.3 . . ?
C00H C00F H00E 109.3 . . ?
C005 C00G H00G 120.6 . . ?
C005 C00G C00I 118.88(14) . . ?
C00I C00G H00G 120.6 . . ?
C00A C00H H00F 109.3 . . ?
C00A C00H H00H 109.3 . . ?
C00F C00H C00A 111.62(12) . . ?
C00F C00H H00F 109.3 . . ?
C00F C00H H00H 109.3 . . ?
H00F C00H H00H 108.0 . . ?
C006 C00I C00G 121.64(13) . . ?
C006 C00I H00I 119.2 . . ?
C00G C00I H00I 119.2 . . ?
C007 C00J H00J 109.5 . . ?
C007 C00J H00K 109.5 . . ?
C007 C00J H00L 109.5 . . ?
H00J C00J H00K 109.5 . . ?
H00J C00J H00L 109.5 . . ?
H00K C00J H00L 109.5 . . ?
C00D C00K H00M 108.6 . . ?
C00D C00K H00N 108.6 . . ?
C00D C00K C00L 114.53(12) . . ?
H00M C00K H00N 107.6 . . ?
C00L C00K H00M 108.6 . . ?
C00L C00K H00N 108.6 . . ?
C00C C00L H00O 109.4 . . ?
C00C C00L H00P 109.4 . . ?
C00K C00L C00C 111.28(12) . . ?
C00K C00L H00O 109.4 . . ?
C00K C00L H00P 109.4 . . ?
H00O C00L H00P 108.0 . . ?
C009 C00M H00Q 109.5 . . ?
C009 C00M H00R 109.5 . . ?
C009 C00M H00S 109.5 . . ?
H00Q C00M H00R 109.5 . . ?
H00Q C00M H00S 109.5 . . ?
H00R C00M H00S 109.5 . . ?
C00B C00N H00T 109.5 . . ?
C00B C00N H00U 109.5 . . ?
C00B C00N H00V 109.5 . . ?
H00T C00N H00U 109.5 . . ?
H00T C00N H00V 109.5 . . ?
H00U C00N H00V 109.5 . . ?
C00A C00O H00W 109.5 . . ?
C00A C00O H00X 109.5 . . ?
C00A C00O H00Y 109.5 . . ?
H00W C00O H00X 109.5 . . ?
H00W C00O H00Y 109.5 . . ?
H00X C00O H00Y 109.5 . . ?

_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 1.676
_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_r20220716d
_database_code_depnum_ccdc_archive 'CCDC 2192301'
loop_
_audit_author_name
_audit_author_address
'Zhang Qunlong'
;Nankai University
China
;
_audit_update_record             
;
2022-07-25 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2022-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H30 O2'
_chemical_formula_sum            'C23 H30 O2'
_chemical_formula_weight         338.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.6931(4)
_cell_length_b                   25.8093(8)
_cell_length_c                   7.4931(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.745(4)
_cell_angle_gamma                90
_cell_volume                     1828.38(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.5370
_cell_measurement_theta_min      2.2780
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11231
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.631
_diffrn_reflns_theta_min         2.294
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    1.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    1.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0174158000
_diffrn_orient_matrix_UB_12      0.0248140000
_diffrn_orient_matrix_UB_13      -0.0393059000
_diffrn_orient_matrix_UB_21      -0.0459883000
_diffrn_orient_matrix_UB_22      -0.0116573000
_diffrn_orient_matrix_UB_23      -0.0761551000
_diffrn_orient_matrix_UB_31      -0.0566707000
_diffrn_orient_matrix_UB_32      0.0018658000
_diffrn_orient_matrix_UB_33      0.0455438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.513
_reflns_Friedel_fraction_full    0.642
_reflns_Friedel_fraction_max     0.477
_reflns_number_gt                4333
_reflns_number_total             5088
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(9)
_refine_ls_extinction_coef       0.0050(11)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5088
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.031
_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)+(0.0586P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1241
_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:
 C00H(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00A(H00C,H00D), C00I(H00K,H00L), C00J(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00E), C00F(H00I), C00K(H00O)
2.d Idealised Me refined as rotating group:
 C00E(H00F,H00G,H00H), C00L(H00P,H00Q,H00R), C00M(H00S,H00T,H00U), C00N(H00V,
 H00W,H00X), C00O(H00Y,H,HA), C00P(H00Z,HB,HC)
;
_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
O001 O 0.69395(16) 0.32780(6) 0.7288(2) 0.0259(3) Uani 1 1 d . . . . .
O002 O 0.14611(17) 0.27656(6) 0.7613(2) 0.0283(4) Uani 1 1 d . . . . .
C003 C 0.4489(2) 0.34699(7) 0.6698(2) 0.0179(4) Uani 1 1 d . . . . .
C004 C 0.3131(2) 0.33305(7) 0.6828(3) 0.0193(4) Uani 1 1 d . . . . .
C005 C 0.5613(2) 0.31398(8) 0.7451(3) 0.0203(4) Uani 1 1 d . . . . .
C006 C 0.2853(2) 0.28699(8) 0.7635(3) 0.0217(4) Uani 1 1 d . . . . .
C007 C 0.5480(2) 0.40808(7) 0.4496(3) 0.0199(4) Uani 1 1 d . . . . .
C008 C 0.4738(2) 0.44281(8) 0.7185(3) 0.0236(4) Uani 1 1 d . . . . .
H00A H 0.455102 0.476976 0.657983 0.028 Uiso 1 1 calc R U . . .
H00B H 0.408875 0.438786 0.802698 0.028 Uiso 1 1 calc R U . . .
C009 C 0.4434(2) 0.39970(7) 0.5719(3) 0.0176(4) Uani 1 1 d . . . . .
C00A C 0.2074(2) 0.37281(8) 0.5953(3) 0.0230(4) Uani 1 1 d . . . . .
H00C H 0.184714 0.396933 0.687482 0.028 Uiso 1 1 calc R U . . .
H00D H 0.118994 0.356325 0.527618 0.028 Uiso 1 1 calc R U . . .
C00B C 0.5064(3) 0.40400(8) 0.2674(3) 0.0268(5) Uani 1 1 d . . . . .
H00E H 0.574795 0.411177 0.197435 0.032 Uiso 1 1 calc R U . . .
C00C C 0.6939(2) 0.42368(8) 0.5351(3) 0.0241(4) Uani 1 1 d . . . . .
C00D C 0.7314(3) 0.43859(8) 0.7103(3) 0.0270(5) Uani 1 1 d . . . . .
C00E C 0.2266(3) 0.45563(8) 0.4180(3) 0.0291(5) Uani 1 1 d . . . . .
H00F H 0.226008 0.474375 0.531559 0.044 Uiso 1 1 calc R U . . .
H00G H 0.129988 0.453490 0.343654 0.044 Uiso 1 1 calc R U . . .
H00H H 0.286666 0.474065 0.349482 0.044 Uiso 1 1 calc R U . . .
C00F C 0.5339(2) 0.26842(8) 0.8296(3) 0.0260(5) Uani 1 1 d . . . . .
H00I H 0.610179 0.246262 0.882665 0.031 Uiso 1 1 calc R U . . .
C00G C 0.2845(2) 0.40107(7) 0.4636(3) 0.0207(4) Uani 1 1 d . . . . .
C00H C 0.2699(2) 0.36801(8) 0.2881(3) 0.0246(4) Uani 1 1 d . . . . .
H00J H 0.306256 0.332624 0.327649 0.030 Uiso 1 1 calc R U . . .
C00I C 0.3627(3) 0.38925(9) 0.1656(3) 0.0308(5) Uani 1 1 d . . . . .
H00K H 0.371163 0.362726 0.073175 0.037 Uiso 1 1 calc R U . . .
H00L H 0.316088 0.420012 0.099729 0.037 Uiso 1 1 calc R U . . .
C00J C 0.6244(3) 0.44128(8) 0.8273(3) 0.0278(5) Uani 1 1 d . . . . .
H00M H 0.642790 0.472642 0.905009 0.033 Uiso 1 1 calc R U . . .
H00N H 0.636449 0.410754 0.909287 0.033 Uiso 1 1 calc R U . . .
C00K C 0.3971(2) 0.25465(8) 0.8381(3) 0.0258(5) Uani 1 1 d . . . . .
H00O H 0.380177 0.223094 0.894965 0.031 Uiso 1 1 calc R U . . .
C00L C 0.1144(3) 0.22452(9) 0.8021(4) 0.0378(6) Uani 1 1 d . . . . .
H00P H 0.155337 0.200652 0.726202 0.057 Uiso 1 1 calc R U . . .
H00Q H 0.011551 0.219802 0.776545 0.057 Uiso 1 1 calc R U . . .
H00R H 0.154376 0.217340 0.931618 0.057 Uiso 1 1 calc R U . . .
C00M C 0.8019(3) 0.41832(10) 0.4183(4) 0.0368(6) Uani 1 1 d . . . . .
H00S H 0.803447 0.382393 0.376442 0.055 Uiso 1 1 calc R U . . .
H00T H 0.895639 0.427713 0.490594 0.055 Uiso 1 1 calc R U . . .
H00U H 0.776665 0.441371 0.312187 0.055 Uiso 1 1 calc R U . . .
C00N C 0.8816(3) 0.44897(11) 0.8083(4) 0.0412(6) Uani 1 1 d . . . . .
H00V H 0.936585 0.416879 0.815540 0.062 Uiso 1 1 calc R U . . .
H00W H 0.883241 0.461605 0.932040 0.062 Uiso 1 1 calc R U . . .
H00X H 0.922813 0.475182 0.741011 0.062 Uiso 1 1 calc R U . . .
C00O C 0.1189(3) 0.36133(10) 0.1761(4) 0.0385(6) Uani 1 1 d . . . . .
H00Y H 0.059775 0.346494 0.253751 0.058 Uiso 1 1 calc R U . . .
H H 0.119217 0.338062 0.072863 0.058 Uiso 1 1 calc R U . . .
HA H 0.080885 0.395131 0.130006 0.058 Uiso 1 1 calc R U . . .
C00P C 0.8080(3) 0.29608(12) 0.8109(5) 0.0471(7) Uani 1 1 d . . . . .
H00Z H 0.791799 0.260785 0.762622 0.071 Uiso 1 1 calc R U . . .
HB H 0.816409 0.295590 0.943653 0.071 Uiso 1 1 calc R U . . .
HC H 0.895508 0.309730 0.783794 0.071 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
O001 C005 1.365(3) . ?
O001 C00P 1.404(3) . ?
O002 C006 1.372(3) . ?
O002 C00L 1.426(3) . ?
C003 C004 1.388(3) . ?
C003 C005 1.400(3) . ?
C003 C009 1.541(3) . ?
C004 C006 1.387(3) . ?
C004 C00A 1.496(3) . ?
C005 C00F 1.389(3) . ?
C006 C00K 1.384(3) . ?
C007 C009 1.525(3) . ?
C007 C00B 1.340(3) . ?
C007 C00C 1.474(3) . ?
C008 H00A 0.9900 . ?
C008 H00B 0.9900 . ?
C008 C009 1.545(3) . ?
C008 C00J 1.507(3) . ?
C009 C00G 1.574(3) . ?
C00A H00C 0.9900 . ?
C00A H00D 0.9900 . ?
C00A C00G 1.546(3) . ?
C00B H00E 0.9500 . ?
C00B C00I 1.482(3) . ?
C00C C00D 1.339(3) . ?
C00C C00M 1.512(3) . ?
C00D C00J 1.499(3) . ?
C00D C00N 1.503(3) . ?
C00E H00F 0.9800 . ?
C00E H00G 0.9800 . ?
C00E H00H 0.9800 . ?
C00E C00G 1.527(3) . ?
C00F H00I 0.9500 . ?
C00F C00K 1.388(3) . ?
C00G C00H 1.548(3) . ?
C00H H00J 1.0000 . ?
C00H C00I 1.522(3) . ?
C00H C00O 1.528(3) . ?
C00I H00K 0.9900 . ?
C00I H00L 0.9900 . ?
C00J H00M 0.9900 . ?
C00J H00N 0.9900 . ?
C00K H00O 0.9500 . ?
C00L H00P 0.9800 . ?
C00L H00Q 0.9800 . ?
C00L H00R 0.9800 . ?
C00M H00S 0.9800 . ?
C00M H00T 0.9800 . ?
C00M H00U 0.9800 . ?
C00N H00V 0.9800 . ?
C00N H00W 0.9800 . ?
C00N H00X 0.9800 . ?
C00O H00Y 0.9800 . ?
C00O H 0.9800 . ?
C00O HA 0.9800 . ?
C00P H00Z 0.9800 . ?
C00P HB 0.9800 . ?
C00P HC 0.9800 . ?

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
C005 O001 C00P 118.32(17) . . ?
C006 O002 C00L 116.12(17) . . ?
C004 C003 C005 118.66(17) . . ?
C004 C003 C009 109.13(16) . . ?
C005 C003 C009 132.19(18) . . ?
C003 C004 C00A 111.13(16) . . ?
C006 C004 C003 122.08(18) . . ?
C006 C004 C00A 126.76(18) . . ?
O001 C005 C003 117.98(17) . . ?
O001 C005 C00F 122.76(18) . . ?
C00F C005 C003 119.25(19) . . ?
O002 C006 C004 116.64(17) . . ?
O002 C006 C00K 124.50(17) . . ?
C00K C006 C004 118.86(19) . . ?
C00B C007 C009 120.7(2) . . ?
C00B C007 C00C 120.61(19) . . ?
C00C C007 C009 118.61(17) . . ?
H00A C008 H00B 107.9 . . ?
C009 C008 H00A 109.2 . . ?
C009 C008 H00B 109.2 . . ?
C00J C008 H00A 109.2 . . ?
C00J C008 H00B 109.2 . . ?
C00J C008 C009 112.08(17) . . ?
C003 C009 C008 108.44(15) . . ?
C003 C009 C00G 101.13(15) . . ?
C007 C009 C003 116.94(16) . . ?
C007 C009 C008 106.08(16) . . ?
C007 C009 C00G 113.03(16) . . ?
C008 C009 C00G 111.23(16) . . ?
C004 C00A H00C 111.2 . . ?
C004 C00A H00D 111.2 . . ?
C004 C00A C00G 102.82(16) . . ?
H00C C00A H00D 109.1 . . ?
C00G C00A H00C 111.2 . . ?
C00G C00A H00D 111.2 . . ?
C007 C00B H00E 117.2 . . ?
C007 C00B C00I 125.6(2) . . ?
C00I C00B H00E 117.2 . . ?
C007 C00C C00M 116.3(2) . . ?
C00D C00C C007 122.10(19) . . ?
C00D C00C C00M 121.4(2) . . ?
C00C C00D C00J 120.9(2) . . ?
C00C C00D C00N 123.6(2) . . ?
C00J C00D C00N 115.3(2) . . ?
H00F C00E H00G 109.5 . . ?
H00F C00E H00H 109.5 . . ?
H00G C00E H00H 109.5 . . ?
C00G C00E H00F 109.5 . . ?
C00G C00E H00G 109.5 . . ?
C00G C00E H00H 109.5 . . ?
C005 C00F H00I 119.4 . . ?
C00K C00F C005 121.3(2) . . ?
C00K C00F H00I 119.4 . . ?
C00A C00G C009 102.47(16) . . ?
C00A C00G C00H 108.40(16) . . ?
C00E C00G C009 113.93(17) . . ?
C00E C00G C00A 111.84(18) . . ?
C00E C00G C00H 110.99(17) . . ?
C00H C00G C009 108.76(16) . . ?
C00G C00H H00J 106.9 . . ?
C00I C00H C00G 111.01(18) . . ?
C00I C00H H00J 106.9 . . ?
C00I C00H C00O 109.37(19) . . ?
C00O C00H C00G 115.2(2) . . ?
C00O C00H H00J 106.9 . . ?
C00B C00I C00H 113.28(19) . . ?
C00B C00I H00K 108.9 . . ?
C00B C00I H00L 108.9 . . ?
C00H C00I H00K 108.9 . . ?
C00H C00I H00L 108.9 . . ?
H00K C00I H00L 107.7 . . ?
C008 C00J H00M 108.9 . . ?
C008 C00J H00N 108.9 . . ?
C00D C00J C008 113.39(18) . . ?
C00D C00J H00M 108.9 . . ?
C00D C00J H00N 108.9 . . ?
H00M C00J H00N 107.7 . . ?
C006 C00K C00F 119.85(18) . . ?
C006 C00K H00O 120.1 . . ?
C00F C00K H00O 120.1 . . ?
O002 C00L H00P 109.5 . . ?
O002 C00L H00Q 109.5 . . ?
O002 C00L H00R 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
H00P C00L H00R 109.5 . . ?
H00Q C00L H00R 109.5 . . ?
C00C C00M H00S 109.5 . . ?
C00C C00M H00T 109.5 . . ?
C00C C00M H00U 109.5 . . ?
H00S C00M H00T 109.5 . . ?
H00S C00M H00U 109.5 . . ?
H00T C00M H00U 109.5 . . ?
C00D C00N H00V 109.5 . . ?
C00D C00N H00W 109.5 . . ?
C00D C00N H00X 109.5 . . ?
H00V C00N H00W 109.5 . . ?
H00V C00N H00X 109.5 . . ?
H00W C00N H00X 109.5 . . ?
C00H C00O H00Y 109.5 . . ?
C00H C00O H 109.5 . . ?
C00H C00O HA 109.5 . . ?
H00Y C00O H 109.5 . . ?
H00Y C00O HA 109.5 . . ?
H C00O HA 109.5 . . ?
O001 C00P H00Z 109.5 . . ?
O001 C00P HB 109.5 . . ?
O001 C00P HC 109.5 . . ?
H00Z C00P HB 109.5 . . ?
H00Z C00P HC 109.5 . . ?
HB C00P HC 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
O001 C005 C00F C00K -177.6(2) . . . . ?
O002 C006 C00K C00F 178.7(2) . . . . ?
C003 C004 C006 O002 -177.39(18) . . . . ?
C003 C004 C006 C00K 1.9(3) . . . . ?
C003 C004 C00A C00G 21.5(2) . . . . ?
C003 C005 C00F C00K 1.1(3) . . . . ?
C003 C009 C00G C00A 34.38(17) . . . . ?
C003 C009 C00G C00E 155.38(18) . . . . ?
C003 C009 C00G C00H -80.24(18) . . . . ?
C004 C003 C005 O001 178.99(18) . . . . ?
C004 C003 C005 C00F 0.2(3) . . . . ?
C004 C003 C009 C007 -145.82(17) . . . . ?
C004 C003 C009 C008 94.38(19) . . . . ?
C004 C003 C009 C00G -22.65(19) . . . . ?
C004 C006 C00K C00F -0.6(3) . . . . ?
C004 C00A C00G C009 -34.24(19) . . . . ?
C004 C00A C00G C00E -156.67(18) . . . . ?
C004 C00A C00G C00H 80.6(2) . . . . ?
C005 C003 C004 C006 -1.7(3) . . . . ?
C005 C003 C004 C00A 179.95(17) . . . . ?
C005 C003 C009 C007 35.6(3) . . . . ?
C005 C003 C009 C008 -84.2(2) . . . . ?
C005 C003 C009 C00G 158.7(2) . . . . ?
C005 C00F C00K C006 -0.9(3) . . . . ?
C006 C004 C00A C00G -156.76(19) . . . . ?
C007 C009 C00G C00A 160.20(15) . . . . ?
C007 C009 C00G C00E -78.8(2) . . . . ?
C007 C009 C00G C00H 45.6(2) . . . . ?
C007 C00B C00I C00H -11.8(3) . . . . ?
C007 C00C C00D C00J -1.5(3) . . . . ?
C007 C00C C00D C00N 172.8(2) . . . . ?
C008 C009 C00G C00A -80.60(18) . . . . ?
C008 C009 C00G C00E 40.4(2) . . . . ?
C008 C009 C00G C00H 164.78(15) . . . . ?
C009 C003 C004 C006 179.44(18) . . . . ?
C009 C003 C004 C00A 1.1(2) . . . . ?
C009 C003 C005 O001 -2.5(3) . . . . ?
C009 C003 C005 C00F 178.7(2) . . . . ?
C009 C007 C00B C00I -2.8(3) . . . . ?
C009 C007 C00C C00D -10.8(3) . . . . ?
C009 C007 C00C C00M 164.97(18) . . . . ?
C009 C008 C00J C00D 49.7(2) . . . . ?
C009 C00G C00H C00I -60.4(2) . . . . ?
C009 C00G C00H C00O 174.63(18) . . . . ?
C00A C004 C006 O002 0.7(3) . . . . ?
C00A C004 C006 C00K 180.0(2) . . . . ?
C00A C00G C00H C00I -171.08(18) . . . . ?
C00A C00G C00H C00O 63.9(2) . . . . ?
C00B C007 C009 C003 101.7(2) . . . . ?
C00B C007 C009 C008 -137.3(2) . . . . ?
C00B C007 C009 C00G -15.1(3) . . . . ?
C00B C007 C00C C00D 165.8(2) . . . . ?
C00B C007 C00C C00M -18.5(3) . . . . ?
C00C C007 C009 C003 -81.8(2) . . . . ?
C00C C007 C009 C008 39.3(2) . . . . ?
C00C C007 C009 C00G 161.42(16) . . . . ?
C00C C007 C00B C00I -179.3(2) . . . . ?
C00C C00D C00J C008 -18.4(3) . . . . ?
C00E C00G C00H C00I 65.7(2) . . . . ?
C00E C00G C00H C00O -59.3(2) . . . . ?
C00G C00H C00I C00B 43.7(3) . . . . ?
C00J C008 C009 C003 68.1(2) . . . . ?
C00J C008 C009 C007 -58.2(2) . . . . ?
C00J C008 C009 C00G 178.48(16) . . . . ?
C00L O002 C006 C004 165.0(2) . . . . ?
C00L O002 C006 C00K -14.2(3) . . . . ?
C00M C00C C00D C00J -177.0(2) . . . . ?
C00M C00C C00D C00N -2.7(3) . . . . ?
C00N C00D C00J C008 166.86(19) . . . . ?
C00O C00H C00I C00B 171.9(2) . . . . ?
C00P O001 C005 C003 177.2(2) . . . . ?
C00P O001 C005 C00F -4.0(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.938
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_ky05062
_database_code_depnum_ccdc_archive 'CCDC 2141304'
loop_
_audit_author_name
_audit_author_address
'Zhang Qunlong'
;Nankai University
China
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_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         'C21 H28 O3'
_chemical_formula_sum            'C21 H28 O3'
_chemical_formula_weight         328.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   13.35230(10)
_cell_length_b                   7.54950(10)
_cell_length_c                   16.84080(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.7850(10)
_cell_angle_gamma                90
_cell_volume                     1677.69(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6774
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6010
_cell_measurement_theta_min      5.7970
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13374
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.833
_diffrn_reflns_theta_min         5.837
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  25.00   0.50    0.50    --    0.00 -80.00  39.00   56
  2  ω    -33.00  -5.00   0.50    0.50    --    0.00 -80.00  39.00   56
  3  ω     82.00 138.00   0.50    0.50    --  101.30  80.00 162.00  112
  4  ω     49.00 133.00   0.50    0.50    --  101.30 -80.00  39.00  168
  5  ω    -25.00  41.00   0.50    0.50    --    0.00  80.00 162.00  132
  6  ω    -37.00  35.00   0.50    0.50    --    0.00 -82.00-180.00  144
  7  ω      1.00  33.00   0.50    0.50    --    0.00 -82.00 -30.00   64
  8  ω    -39.00  -9.00   0.50    0.50    --    0.00 -82.00 -30.00   60
  9  ω     21.00  90.00   0.50    0.50    --  101.30 -77.00 120.00  138
 10  ω    110.00 135.00   0.50    0.50    --  101.30 -77.00 120.00   50
 11  ω    135.00 191.00   0.50    0.50    --  101.30  82.00  90.00  112
 12  ω     94.00 185.00   0.50    0.50    --  101.30  38.00-120.00  182
 13  ω     85.00 191.00   0.50    0.50    --  101.30  82.00-180.00  212
 14  ω     75.00 191.00   0.50    0.50    --  101.30  57.00 150.00  232
 15  ω     82.00 191.00   0.50    0.50    --  101.30  82.00  60.00  218
 16  ω     80.00 190.00   0.50    0.50    --  101.30  38.00 -90.00  220
 17  ω     84.00 110.00   0.50    0.50    --  101.30  82.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0463929000
_diffrn_orient_matrix_UB_12      -0.0330018000
_diffrn_orient_matrix_UB_13      -0.0769784000
_diffrn_orient_matrix_UB_21      0.0622017000
_diffrn_orient_matrix_UB_22      0.1719048000
_diffrn_orient_matrix_UB_23      0.0151994000
_diffrn_orient_matrix_UB_31      0.0872327000
_diffrn_orient_matrix_UB_32      -0.1049071000
_diffrn_orient_matrix_UB_33      0.0491075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3056
_reflns_number_total             3407
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.083
_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)+(0.0523P)²+0.6333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1106
_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(H1A), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), 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 0.08164(6) 0.39713(11) 0.43480(5) 0.0174(2) Uani 1 1 d . . . . .
O1 O 0.13365(7) 0.56761(12) 0.58481(5) 0.0218(2) Uani 1 1 d . . . . .
H1 H 0.081506 0.574745 0.552204 0.033 Uiso 1 1 calc R U . . .
O3 O 0.22002(7) 0.64405(12) 0.15962(5) 0.0216(2) Uani 1 1 d . . . . .
H3 H 0.184175 0.724468 0.138477 0.032 Uiso 1 1 calc R U . . .
C20 C 0.11430(9) 0.46329(16) 0.36606(7) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.21167(9) 0.43236(16) 0.35227(7) 0.0165(3) Uani 1 1 d . . . . .
C16 C 0.24642(9) 0.48772(16) 0.28280(7) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.18273(10) 0.58564(16) 0.22641(7) 0.0183(3) Uani 1 1 d . . . . .
C18 C 0.08366(10) 0.61772(16) 0.23978(7) 0.0198(3) Uani 1 1 d . . . . .
H18 H 0.040155 0.681922 0.201960 0.024 Uiso 1 1 calc R U . . .
C15 C 0.35279(9) 0.42018(17) 0.28392(7) 0.0190(3) Uani 1 1 d . . . . .
H15A H 0.402291 0.512225 0.300433 0.023 Uiso 1 1 calc R U . . .
H15B H 0.362455 0.376085 0.231523 0.023 Uiso 1 1 calc R U . . .
C1 C 0.20748(9) 0.46575(16) 0.55091(7) 0.0179(3) Uani 1 1 d . . . . .
H1A H 0.251696 0.409929 0.595764 0.022 Uiso 1 1 calc R U . . .
C19 C 0.04833(9) 0.55568(16) 0.30860(7) 0.0191(3) Uani 1 1 d . . . . .
H19 H -0.018365 0.575831 0.315927 0.023 Uiso 1 1 calc R U . . .
C2 C 0.15760(9) 0.31542(16) 0.49693(7) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.34806(9) 0.48586(16) 0.46470(7) 0.0181(3) Uani 1 1 d . . . . .
H5A H 0.399853 0.431237 0.503698 0.022 Uiso 1 1 calc R U . . .
H5B H 0.381139 0.567957 0.432779 0.022 Uiso 1 1 calc R U . . .
C4 C 0.29292(9) 0.34076(16) 0.40919(7) 0.0162(3) Uani 1 1 d . . . . .
C12 C 0.36091(9) 0.26681(16) 0.34728(7) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.27380(9) 0.58762(16) 0.50886(7) 0.0189(3) Uani 1 1 d . . . . .
H6A H 0.311816 0.665238 0.548390 0.023 Uiso 1 1 calc R U . . .
H6B H 0.230701 0.661089 0.470592 0.023 Uiso 1 1 calc R U . . .
C11 C 0.30991(9) 0.10050(16) 0.30308(7) 0.0192(3) Uani 1 1 d . . . . .
H11 H 0.251533 0.143320 0.265589 0.023 Uiso 1 1 calc R U . . .
C14 C 0.47131(9) 0.23110(18) 0.38337(8) 0.0216(3) Uani 1 1 d . . . . .
H14A H 0.510254 0.209102 0.340960 0.032 Uiso 1 1 calc R U . . .
H14B H 0.474572 0.129475 0.417938 0.032 Uiso 1 1 calc R U . . .
H14C H 0.498376 0.332325 0.413868 0.032 Uiso 1 1 calc R U . . .
C3 C 0.24097(9) 0.20752(16) 0.46052(7) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.31613(10) 0.12451(17) 0.52932(8) 0.0215(3) Uani 1 1 d . . . . .
H8A H 0.345472 0.216174 0.565003 0.032 Uiso 1 1 calc R U . . .
H8B H 0.368761 0.063830 0.507256 0.032 Uiso 1 1 calc R U . . .
H8C H 0.280845 0.041957 0.558448 0.032 Uiso 1 1 calc R U . . .
C7 C 0.09272(10) 0.19927(17) 0.54289(8) 0.0214(3) Uani 1 1 d . . . . .
H7A H 0.040107 0.269647 0.560061 0.032 Uiso 1 1 calc R U . . .
H7B H 0.134308 0.149310 0.588991 0.032 Uiso 1 1 calc R U . . .
H7C H 0.062899 0.105681 0.508566 0.032 Uiso 1 1 calc R U . . .
C10 C 0.26879(10) -0.03009(17) 0.35963(8) 0.0215(3) Uani 1 1 d . . . . .
H10A H 0.236301 -0.128063 0.328489 0.026 Uiso 1 1 calc R U . . .
H10B H 0.324795 -0.077488 0.397079 0.026 Uiso 1 1 calc R U . . .
C9 C 0.19288(10) 0.05603(16) 0.40658(8) 0.0199(3) Uani 1 1 d . . . . .
H9A H 0.166711 -0.032781 0.439633 0.024 Uiso 1 1 calc R U . . .
H9B H 0.136397 0.102111 0.369211 0.024 Uiso 1 1 calc R U . . .
C13 C 0.37868(10) 0.00252(19) 0.25274(8) 0.0246(3) Uani 1 1 d . . . . .
H13A H 0.405177 0.085027 0.217858 0.037 Uiso 1 1 calc R U . . .
H13B H 0.340292 -0.087152 0.221092 0.037 Uiso 1 1 calc R U . . .
H13C H 0.433674 -0.051716 0.287709 0.037 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 C20 1.3908(14) . ?
O2 C2 1.4764(14) . ?
O1 H1 0.8200 . ?
O1 C1 1.4356(14) . ?
O3 H3 0.8200 . ?
O3 C17 1.3707(14) . ?
C20 C21 1.3750(17) . ?
C20 C19 1.3923(17) . ?
C21 C16 1.3872(16) . ?
C21 C4 1.5021(16) . ?
C16 C17 1.3874(17) . ?
C16 C15 1.5064(17) . ?
C17 C18 1.3965(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3972(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C12 1.5671(16) . ?
C1 H1A 0.9800 . ?
C1 C2 1.5405(16) . ?
C1 C6 1.5243(17) . ?
C19 H19 0.9300 . ?
C2 C3 1.5772(16) . ?
C2 C7 1.5241(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.5510(16) . ?
C5 C6 1.5335(16) . ?
C4 C12 1.5848(16) . ?
C4 C3 1.5567(16) . ?
C12 C11 1.5619(17) . ?
C12 C14 1.5302(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C10 1.5299(17) . ?
C11 C13 1.5319(17) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 C8 1.5450(17) . ?
C3 C9 1.5386(17) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.5231(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
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
C20 O2 C2 118.11(9) . . ?
C1 O1 H1 109.5 . . ?
C17 O3 H3 109.5 . . ?
O2 C20 C19 120.85(11) . . ?
C21 C20 O2 120.29(11) . . ?
C21 C20 C19 118.81(11) . . ?
C20 C21 C16 122.54(11) . . ?
C20 C21 C4 125.43(11) . . ?
C16 C21 C4 112.01(10) . . ?
C21 C16 C17 119.26(11) . . ?
C21 C16 C15 108.88(10) . . ?
C17 C16 C15 131.84(11) . . ?
O3 C17 C16 118.14(11) . . ?
O3 C17 C18 123.25(11) . . ?
C16 C17 C18 118.61(11) . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.58(11) . . ?
C19 C18 H18 119.2 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C16 C15 C12 103.04(9) . . ?
H15A C15 H15B 109.1 . . ?
C12 C15 H15A 111.2 . . ?
C12 C15 H15B 111.2 . . ?
O1 C1 H1A 107.1 . . ?
O1 C1 C2 111.59(10) . . ?
O1 C1 C6 110.14(10) . . ?
C2 C1 H1A 107.1 . . ?
C6 C1 H1A 107.1 . . ?
C6 C1 C2 113.58(9) . . ?
C20 C19 C18 119.11(11) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
O2 C2 C1 107.38(9) . . ?
O2 C2 C3 112.92(9) . . ?
O2 C2 C7 102.60(9) . . ?
C1 C2 C3 110.04(9) . . ?
C7 C2 C1 110.63(9) . . ?
C7 C2 C3 112.95(10) . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C6 C5 C4 111.32(10) . . ?
C21 C4 C5 106.83(10) . . ?
C21 C4 C12 99.96(9) . . ?
C21 C4 C3 108.19(10) . . ?
C5 C4 C12 112.24(9) . . ?
C5 C4 C3 109.41(9) . . ?
C3 C4 C12 119.09(10) . . ?
C15 C12 C4 101.57(9) . . ?
C11 C12 C15 106.84(9) . . ?
C11 C12 C4 110.18(9) . . ?
C14 C12 C15 111.28(10) . . ?
C14 C12 C4 114.50(10) . . ?
C14 C12 C11 111.78(10) . . ?
C1 C6 C5 112.79(10) . . ?
C1 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C12 C11 H11 106.7 . . ?
C10 C11 C12 113.14(10) . . ?
C10 C11 H11 106.7 . . ?
C10 C11 C13 109.63(10) . . ?
C13 C11 C12 113.42(10) . . ?
C13 C11 H11 106.7 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C3 C2 106.44(9) . . ?
C8 C3 C2 109.51(9) . . ?
C8 C3 C4 112.65(10) . . ?
C9 C3 C2 110.96(10) . . ?
C9 C3 C4 109.49(9) . . ?
C9 C3 C8 107.82(10) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C9 C10 C11 112.25(10) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C3 C9 H9A 109.2 . . ?
C3 C9 H9B 109.2 . . ?
C10 C9 C3 111.90(10) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
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
O2 C20 C21 C16 176.69(10) . . . . ?
O2 C20 C21 C4 -4.72(19) . . . . ?
O2 C20 C19 C18 -179.04(11) . . . . ?
O2 C2 C3 C4 58.80(12) . . . . ?
O2 C2 C3 C8 -179.16(9) . . . . ?
O2 C2 C3 C9 -60.25(12) . . . . ?
O1 C1 C2 O2 56.40(12) . . . . ?
O1 C1 C2 C3 179.67(9) . . . . ?
O1 C1 C2 C7 -54.82(13) . . . . ?
O1 C1 C6 C5 -174.76(9) . . . . ?
O3 C17 C18 C19 179.88(11) . . . . ?
C20 O2 C2 C1 84.79(11) . . . . ?
C20 O2 C2 C3 -36.69(13) . . . . ?
C20 O2 C2 C7 -158.58(10) . . . . ?
C20 C21 C16 C17 3.24(19) . . . . ?
C20 C21 C16 C15 -175.48(11) . . . . ?
C20 C21 C4 C5 -88.85(14) . . . . ?
C20 C21 C4 C12 154.11(12) . . . . ?
C20 C21 C4 C3 28.85(16) . . . . ?
C21 C20 C19 C18 -1.53(18) . . . . ?
C21 C16 C17 O3 177.76(10) . . . . ?
C21 C16 C17 C18 -3.14(18) . . . . ?
C21 C16 C15 C12 18.80(13) . . . . ?
C21 C4 C12 C15 36.32(11) . . . . ?
C21 C4 C12 C11 -76.65(11) . . . . ?
C21 C4 C12 C14 156.34(10) . . . . ?
C21 C4 C3 C2 -51.93(12) . . . . ?
C21 C4 C3 C8 -171.96(10) . . . . ?
C21 C4 C3 C9 68.08(12) . . . . ?
C16 C21 C4 C5 89.87(12) . . . . ?
C16 C21 C4 C12 -27.17(12) . . . . ?
C16 C21 C4 C3 -152.43(10) . . . . ?
C16 C17 C18 C19 0.83(19) . . . . ?
C16 C15 C12 C4 -34.14(11) . . . . ?
C16 C15 C12 C11 81.32(11) . . . . ?
C16 C15 C12 C14 -156.41(10) . . . . ?
C17 C16 C15 C12 -159.70(13) . . . . ?
C17 C18 C19 C20 1.54(19) . . . . ?
C15 C16 C17 O3 -3.9(2) . . . . ?
C15 C16 C17 C18 175.23(12) . . . . ?
C15 C12 C11 C10 -154.17(10) . . . . ?
C15 C12 C11 C13 80.15(12) . . . . ?
C1 C2 C3 C4 -61.17(12) . . . . ?
C1 C2 C3 C8 60.87(12) . . . . ?
C1 C2 C3 C9 179.78(9) . . . . ?
C19 C20 C21 C16 -0.84(19) . . . . ?
C19 C20 C21 C4 177.75(11) . . . . ?
C2 O2 C20 C21 8.24(16) . . . . ?
C2 O2 C20 C19 -174.28(10) . . . . ?
C2 C1 C6 C5 -48.77(14) . . . . ?
C2 C3 C9 C10 170.30(10) . . . . ?
C5 C4 C12 C15 -76.60(11) . . . . ?
C5 C4 C12 C11 170.43(10) . . . . ?
C5 C4 C12 C14 43.43(14) . . . . ?
C5 C4 C3 C2 64.11(12) . . . . ?
C5 C4 C3 C8 -55.92(13) . . . . ?
C5 C4 C3 C9 -175.88(10) . . . . ?
C4 C21 C16 C17 -175.53(11) . . . . ?
C4 C21 C16 C15 5.75(14) . . . . ?
C4 C5 C6 C1 50.78(13) . . . . ?
C4 C12 C11 C10 -44.63(13) . . . . ?
C4 C12 C11 C13 -170.30(10) . . . . ?
C4 C3 C9 C10 53.10(13) . . . . ?
C12 C4 C3 C2 -164.95(10) . . . . ?
C12 C4 C3 C8 75.02(13) . . . . ?
C12 C4 C3 C9 -44.94(14) . . . . ?
C12 C11 C10 C9 57.02(14) . . . . ?
C6 C1 C2 O2 -68.82(12) . . . . ?
C6 C1 C2 C3 54.45(13) . . . . ?
C6 C1 C2 C7 179.96(10) . . . . ?
C6 C5 C4 C21 57.13(12) . . . . ?
C6 C5 C4 C12 165.72(10) . . . . ?
C6 C5 C4 C3 -59.77(12) . . . . ?
C11 C10 C9 C3 -61.50(14) . . . . ?
C14 C12 C11 C10 83.88(12) . . . . ?
C14 C12 C11 C13 -41.80(14) . . . . ?
C3 C4 C12 C15 153.73(10) . . . . ?
C3 C4 C12 C11 40.76(14) . . . . ?
C3 C4 C12 C14 -86.25(13) . . . . ?
C8 C3 C9 C10 -69.77(12) . . . . ?
C7 C2 C3 C4 174.66(9) . . . . ?
C7 C2 C3 C8 -63.30(13) . . . . ?
C7 C2 C3 C9 55.61(13) . . . . ?
C13 C11 C10 C9 -175.29(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.765
####################################################################### 
# 
# 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_r20220716c
_database_code_depnum_ccdc_archive 'CCDC 2192302'
loop_
_audit_author_name
_audit_author_address
'Zhang Qunlong'
;Nankai University
China
;
_audit_update_record             
;
2022-07-25 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2022-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H30 O3'
_chemical_formula_sum            'C23 H30 O3'
_chemical_formula_weight         354.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4840(3)
_cell_length_b                   13.8807(3)
_cell_length_c                   14.0827(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1853.91(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17756
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8680
_cell_measurement_theta_min      2.0380
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23157
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.817
_diffrn_reflns_theta_min         2.060
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.951
_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  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    2.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    2.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268239000
_diffrn_orient_matrix_UB_12      0.0246215000
_diffrn_orient_matrix_UB_13      -0.0402700000
_diffrn_orient_matrix_UB_21      -0.0089613000
_diffrn_orient_matrix_UB_22      0.0446119000
_diffrn_orient_matrix_UB_23      0.0237626000
_diffrn_orient_matrix_UB_31      0.0692541000
_diffrn_orient_matrix_UB_32      -0.0038031000
_diffrn_orient_matrix_UB_33      0.0186977000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                5935
_reflns_number_total             6371
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2373 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       0.019(4)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         6371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.044
_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)+(0.0497P)²+0.1810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0916
_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:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00I,H00J), C00I(H00K,H00L), C00K(H00P,H00Q), C00O(H00U,H00V)
2.c Aromatic/amide H refined with riding coordinates:
 C004(H004), C00A(H00D), C00B(H00E)
2.d Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00C(H00F,H00G,H00H), C00J(H00M,H00N,H00O), C00L(H00R,
 H00S,H00T), C00P(H00W,H00X,H00Y), C00Q(H00Z,H,HA)
;
_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
O001 O 1.07452(11) 0.12062(7) 0.56676(7) 0.0226(2) Uani 1 1 d . . . . .
O002 O 0.52334(11) 0.21323(8) 0.66304(7) 0.0249(2) Uani 1 1 d . . . . .
O003 O 0.37875(15) 0.18790(10) 0.86698(11) 0.0433(3) Uani 1 1 d . . . . .
C004 C 0.67311(15) 0.44889(9) 0.76214(9) 0.0184(2) Uani 1 1 d . . . . .
H004 H 0.595345 0.491560 0.768409 0.022 Uiso 1 1 calc R U . . .
C005 C 0.65618(14) 0.18669(9) 0.63437(9) 0.0180(2) Uani 1 1 d . . . . .
C006 C 0.76925(14) 0.22084(8) 0.68864(8) 0.0155(2) Uani 1 1 d . . . . .
C007 C 0.92256(13) 0.33045(8) 0.77019(8) 0.0152(2) Uani 1 1 d . . . . .
C008 C 0.91609(14) 0.41382(9) 0.69658(8) 0.0164(2) Uani 1 1 d . . . . .
H008 H 0.885522 0.384947 0.634862 0.020 Uiso 1 1 calc R U . . .
C009 C 0.97864(15) 0.36606(10) 0.86598(9) 0.0206(2) Uani 1 1 d . . . . .
H00A H 1.066107 0.402264 0.856023 0.031 Uiso 1 1 calc R U . . .
H00B H 0.997378 0.310731 0.907323 0.031 Uiso 1 1 calc R U . . .
H00C H 0.908298 0.407956 0.895866 0.031 Uiso 1 1 calc R U . . .
C00A C 0.68388(16) 0.12903(10) 0.55567(9) 0.0220(3) Uani 1 1 d . . . . .
H00D H 0.607791 0.105932 0.518159 0.026 Uiso 1 1 calc R U . . .
C00B C 0.82224(16) 0.10466(9) 0.53108(9) 0.0211(3) Uani 1 1 d . . . . .
H00E H 0.839461 0.064827 0.477463 0.025 Uiso 1 1 calc R U . . .
C00C C 1.10746(17) 0.07686(10) 0.47770(9) 0.0247(3) Uani 1 1 d . . . . .
H00F H 1.067169 0.115427 0.426118 0.037 Uiso 1 1 calc R U . . .
H00G H 1.067756 0.011705 0.475735 0.037 Uiso 1 1 calc R U . . .
H00H H 1.210056 0.073407 0.470148 0.037 Uiso 1 1 calc R U . . .
C00D C 0.77128(13) 0.28347(8) 0.77857(8) 0.0148(2) Uani 1 1 d . . . . .
C00E C 0.93469(14) 0.13861(9) 0.58494(9) 0.0174(2) Uani 1 1 d . . . . .
C00F C 1.01125(14) 0.24726(9) 0.72676(9) 0.0183(2) Uani 1 1 d . . . . .
H00I H 1.091938 0.272534 0.689759 0.022 Uiso 1 1 calc R U . . .
H00J H 1.046893 0.203389 0.776715 0.022 Uiso 1 1 calc R U . . .
C00G C 0.90649(14) 0.19720(9) 0.66347(8) 0.0160(2) Uani 1 1 d . . . . .
C00H C 0.65348(14) 0.35738(9) 0.78901(9) 0.0164(2) Uani 1 1 d . . . . .
C00I C 0.76431(16) 0.21436(9) 0.86478(9) 0.0202(2) Uani 1 1 d . . . . .
H00K H 0.843098 0.167734 0.861001 0.024 Uiso 1 1 calc R U . . .
H00L H 0.775517 0.251902 0.924071 0.024 Uiso 1 1 calc R U . . .
C00J C 1.05783(16) 0.46414(11) 0.67860(10) 0.0241(3) Uani 1 1 d . . . . .
H00M H 1.086235 0.499532 0.735699 0.036 Uiso 1 1 calc R U . . .
H00N H 1.048057 0.509181 0.625417 0.036 Uiso 1 1 calc R U . . .
H00O H 1.129632 0.415829 0.663222 0.036 Uiso 1 1 calc R U . . .
C00K C 0.80664(15) 0.48958(9) 0.72319(10) 0.0196(2) Uani 1 1 d . . . . .
H00P H 0.848171 0.533534 0.770967 0.023 Uiso 1 1 calc R U . . .
H00Q H 0.784168 0.528278 0.666110 0.023 Uiso 1 1 calc R U . . .
C00L C 0.5239(2) 0.37137(12) 0.94470(11) 0.0318(3) Uani 1 1 d . . . . .
H00R H 0.602854 0.341354 0.978420 0.048 Uiso 1 1 calc R U . . .
H00S H 0.435639 0.356811 0.977973 0.048 Uiso 1 1 calc R U . . .
H00T H 0.537717 0.441299 0.942576 0.048 Uiso 1 1 calc R U . . .
C00M C 0.51649(15) 0.33109(10) 0.84165(10) 0.0219(3) Uani 1 1 d . . . . .
C00N C 0.49549(18) 0.22228(11) 0.85654(11) 0.0272(3) Uani 1 1 d . . . . .
C00O C 0.62511(17) 0.15979(10) 0.86789(10) 0.0258(3) Uani 1 1 d . . . . .
H00U H 0.625345 0.110752 0.816840 0.031 Uiso 1 1 calc R U . . .
H00V H 0.618665 0.125311 0.929277 0.031 Uiso 1 1 calc R U . . .
C00P C 0.40640(16) 0.17938(11) 0.60906(11) 0.0261(3) Uani 1 1 d . . . . .
H00W H 0.411080 0.206097 0.544726 0.039 Uiso 1 1 calc R U . . .
H00X H 0.318469 0.199874 0.639522 0.039 Uiso 1 1 calc R U . . .
H00Y H 0.409198 0.108883 0.605805 0.039 Uiso 1 1 calc R U . . .
C00Q C 0.38536(17) 0.37373(12) 0.79331(13) 0.0329(3) Uani 1 1 d . . . . .
H00Z H 0.384732 0.443803 0.801785 0.049 Uiso 1 1 calc R U . . .
H H 0.300296 0.346097 0.821927 0.049 Uiso 1 1 calc R U . . .
HA H 0.387410 0.358486 0.725373 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
O001 C00C 1.4281(16) . ?
O001 C00E 1.3735(17) . ?
O002 C005 1.3732(16) . ?
O002 C00P 1.4243(17) . ?
O003 C00N 1.2145(19) . ?
C004 H004 0.9500 . ?
C004 C00H 1.3385(17) . ?
C004 C00K 1.4912(19) . ?
C005 C006 1.3996(17) . ?
C005 C00A 1.3921(18) . ?
C006 C00D 1.5361(16) . ?
C006 C00G 1.3884(18) . ?
C007 C008 1.5547(17) . ?
C007 C009 1.5319(17) . ?
C007 C00D 1.5804(18) . ?
C007 C00F 1.5540(17) . ?
C008 H008 1.0000 . ?
C008 C00J 1.536(2) . ?
C008 C00K 1.5244(18) . ?
C009 H00A 0.9800 . ?
C009 H00B 0.9800 . ?
C009 H00C 0.9800 . ?
C00A H00D 0.9500 . ?
C00A C00B 1.399(2) . ?
C00B H00E 0.9500 . ?
C00B C00E 1.3909(18) . ?
C00C H00F 0.9800 . ?
C00C H00G 0.9800 . ?
C00C H00H 0.9800 . ?
C00D C00H 1.5239(17) . ?
C00D C00I 1.5487(17) . ?
C00E C00G 1.3986(16) . ?
C00F H00I 0.9900 . ?
C00F H00J 0.9900 . ?
C00F C00G 1.5049(17) . ?
C00H C00M 1.5397(18) . ?
C00I H00K 0.9900 . ?
C00I H00L 0.9900 . ?
C00I C00O 1.523(2) . ?
C00J H00M 0.9800 . ?
C00J H00N 0.9800 . ?
C00J H00O 0.9800 . ?
C00K H00P 0.9900 . ?
C00K H00Q 0.9900 . ?
C00L H00R 0.9800 . ?
C00L H00S 0.9800 . ?
C00L H00T 0.9800 . ?
C00L C00M 1.557(2) . ?
C00M C00N 1.538(2) . ?
C00M C00Q 1.536(2) . ?
C00N C00O 1.513(2) . ?
C00O H00U 0.9900 . ?
C00O H00V 0.9900 . ?
C00P H00W 0.9800 . ?
C00P H00X 0.9800 . ?
C00P H00Y 0.9800 . ?
C00Q H00Z 0.9800 . ?
C00Q H 0.9800 . ?
C00Q HA 0.9800 . ?

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
C00E O001 C00C 116.88(11) . . ?
C005 O002 C00P 117.97(11) . . ?
C00H C004 H004 117.2 . . ?
C00H C004 C00K 125.56(12) . . ?
C00K C004 H004 117.2 . . ?
O002 C005 C006 116.83(11) . . ?
O002 C005 C00A 124.16(12) . . ?
C00A C005 C006 119.01(12) . . ?
C005 C006 C00D 130.66(12) . . ?
C00G C006 C005 119.92(11) . . ?
C00G C006 C00D 109.42(11) . . ?
C008 C007 C00D 108.73(10) . . ?
C009 C007 C008 111.14(10) . . ?
C009 C007 C00D 112.49(10) . . ?
C009 C007 C00F 113.48(10) . . ?
C00F C007 C008 108.18(10) . . ?
C00F C007 C00D 102.36(9) . . ?
C007 C008 H008 107.0 . . ?
C00J C008 C007 114.45(11) . . ?
C00J C008 H008 107.0 . . ?
C00K C008 C007 112.11(10) . . ?
C00K C008 H008 107.0 . . ?
C00K C008 C00J 108.83(10) . . ?
C007 C009 H00A 109.5 . . ?
C007 C009 H00B 109.5 . . ?
C007 C009 H00C 109.5 . . ?
H00A C009 H00B 109.5 . . ?
H00A C009 H00C 109.5 . . ?
H00B C009 H00C 109.5 . . ?
C005 C00A H00D 119.6 . . ?
C005 C00A C00B 120.88(13) . . ?
C00B C00A H00D 119.6 . . ?
C00A C00B H00E 119.9 . . ?
C00E C00B C00A 120.16(12) . . ?
C00E C00B H00E 119.9 . . ?
O001 C00C H00F 109.5 . . ?
O001 C00C H00G 109.5 . . ?
O001 C00C H00H 109.5 . . ?
H00F C00C H00G 109.5 . . ?
H00F C00C H00H 109.5 . . ?
H00G C00C H00H 109.5 . . ?
C006 C00D C007 100.57(10) . . ?
C006 C00D C00I 107.17(9) . . ?
C00H C00D C006 116.83(10) . . ?
C00H C00D C007 113.26(9) . . ?
C00H C00D C00I 108.06(10) . . ?
C00I C00D C007 110.66(10) . . ?
O001 C00E C00B 125.25(11) . . ?
O001 C00E C00G 115.96(11) . . ?
C00B C00E C00G 118.79(12) . . ?
C007 C00F H00I 111.2 . . ?
C007 C00F H00J 111.2 . . ?
H00I C00F H00J 109.2 . . ?
C00G C00F C007 102.64(10) . . ?
C00G C00F H00I 111.2 . . ?
C00G C00F H00J 111.2 . . ?
C006 C00G C00E 121.25(12) . . ?
C006 C00G C00F 111.01(10) . . ?
C00E C00G C00F 127.63(12) . . ?
C004 C00H C00D 120.64(12) . . ?
C004 C00H C00M 118.58(11) . . ?
C00D C00H C00M 120.37(10) . . ?
C00D C00I H00K 109.3 . . ?
C00D C00I H00L 109.3 . . ?
H00K C00I H00L 108.0 . . ?
C00O C00I C00D 111.58(11) . . ?
C00O C00I H00K 109.3 . . ?
C00O C00I H00L 109.3 . . ?
C008 C00J H00M 109.5 . . ?
C008 C00J H00N 109.5 . . ?
C008 C00J H00O 109.5 . . ?
H00M C00J H00N 109.5 . . ?
H00M C00J H00O 109.5 . . ?
H00N C00J H00O 109.5 . . ?
C004 C00K C008 114.04(10) . . ?
C004 C00K H00P 108.7 . . ?
C004 C00K H00Q 108.7 . . ?
C008 C00K H00P 108.7 . . ?
C008 C00K H00Q 108.7 . . ?
H00P C00K H00Q 107.6 . . ?
H00R C00L H00S 109.5 . . ?
H00R C00L H00T 109.5 . . ?
H00S C00L H00T 109.5 . . ?
C00M C00L H00R 109.5 . . ?
C00M C00L H00S 109.5 . . ?
C00M C00L H00T 109.5 . . ?
C00H C00M C00L 109.01(12) . . ?
C00N C00M C00H 114.06(11) . . ?
C00N C00M C00L 103.38(12) . . ?
C00Q C00M C00H 112.23(12) . . ?
C00Q C00M C00L 108.12(13) . . ?
C00Q C00M C00N 109.51(13) . . ?
O003 C00N C00M 121.36(15) . . ?
O003 C00N C00O 120.18(14) . . ?
C00O C00N C00M 118.18(13) . . ?
C00I C00O H00U 108.6 . . ?
C00I C00O H00V 108.6 . . ?
C00N C00O C00I 114.59(11) . . ?
C00N C00O H00U 108.6 . . ?
C00N C00O H00V 108.6 . . ?
H00U C00O H00V 107.6 . . ?
O002 C00P H00W 109.5 . . ?
O002 C00P H00X 109.5 . . ?
O002 C00P H00Y 109.5 . . ?
H00W C00P H00X 109.5 . . ?
H00W C00P H00Y 109.5 . . ?
H00X C00P H00Y 109.5 . . ?
C00M C00Q H00Z 109.5 . . ?
C00M C00Q H 109.5 . . ?
C00M C00Q HA 109.5 . . ?
H00Z C00Q H 109.5 . . ?
H00Z C00Q HA 109.5 . . ?
H C00Q HA 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
O001 C00E C00G C006 179.67(11) . . . . ?
O001 C00E C00G C00F 3.83(19) . . . . ?
O002 C005 C006 C00D 1.19(19) . . . . ?
O002 C005 C006 C00G -179.69(11) . . . . ?
O002 C005 C00A C00B -179.73(13) . . . . ?
O003 C00N C00O C00I -172.93(15) . . . . ?
C004 C00H C00M C00L -73.24(16) . . . . ?
C004 C00H C00M C00N 171.80(13) . . . . ?
C004 C00H C00M C00Q 46.51(17) . . . . ?
C005 C006 C00D C007 -154.85(13) . . . . ?
C005 C006 C00D C00H -31.85(18) . . . . ?
C005 C006 C00D C00I 89.47(15) . . . . ?
C005 C006 C00G C00E -0.70(18) . . . . ?
C005 C006 C00G C00F 175.78(11) . . . . ?
C005 C00A C00B C00E -0.5(2) . . . . ?
C006 C005 C00A C00B 0.5(2) . . . . ?
C006 C00D C00H C004 -95.66(14) . . . . ?
C006 C00D C00H C00M 91.79(14) . . . . ?
C006 C00D C00I C00O -64.87(13) . . . . ?
C007 C008 C00K C004 -40.12(15) . . . . ?
C007 C00D C00H C004 20.51(16) . . . . ?
C007 C00D C00H C00M -152.04(11) . . . . ?
C007 C00D C00I C00O -173.64(10) . . . . ?
C007 C00F C00G C006 -18.84(13) . . . . ?
C007 C00F C00G C00E 157.36(12) . . . . ?
C008 C007 C00D C006 78.36(10) . . . . ?
C008 C007 C00D C00H -47.09(12) . . . . ?
C008 C007 C00D C00I -168.61(9) . . . . ?
C008 C007 C00F C00G -80.97(12) . . . . ?
C009 C007 C008 C00J 57.62(14) . . . . ?
C009 C007 C008 C00K -66.94(14) . . . . ?
C009 C007 C00D C006 -158.09(10) . . . . ?
C009 C007 C00D C00H 76.46(12) . . . . ?
C009 C007 C00D C00I -45.06(13) . . . . ?
C009 C007 C00F C00G 155.22(11) . . . . ?
C00A C005 C006 C00D -178.99(12) . . . . ?
C00A C005 C006 C00G 0.13(18) . . . . ?
C00A C00B C00E O001 -178.97(13) . . . . ?
C00A C00B C00E C00G -0.06(19) . . . . ?
C00B C00E C00G C006 0.66(18) . . . . ?
C00B C00E C00G C00F -175.19(12) . . . . ?
C00C O001 C00E C00B 10.50(19) . . . . ?
C00C O001 C00E C00G -168.44(11) . . . . ?
C00D C006 C00G C00E 178.59(11) . . . . ?
C00D C006 C00G C00F -4.93(14) . . . . ?
C00D C007 C008 C00J -178.03(10) . . . . ?
C00D C007 C008 C00K 57.40(12) . . . . ?
C00D C007 C00F C00G 33.74(12) . . . . ?
C00D C00H C00M C00L 99.46(14) . . . . ?
C00D C00H C00M C00N -15.50(17) . . . . ?
C00D C00H C00M C00Q -140.78(13) . . . . ?
C00D C00I C00O C00N -48.86(16) . . . . ?
C00F C007 C008 C00J -67.59(13) . . . . ?
C00F C007 C008 C00K 167.85(10) . . . . ?
C00F C007 C00D C006 -35.94(11) . . . . ?
C00F C007 C00D C00H -161.39(10) . . . . ?
C00F C007 C00D C00I 77.09(11) . . . . ?
C00G C006 C00D C007 25.96(12) . . . . ?
C00G C006 C00D C00H 148.95(11) . . . . ?
C00G C006 C00D C00I -89.72(12) . . . . ?
C00H C004 C00K C008 11.71(19) . . . . ?
C00H C00D C00I C00O 61.82(13) . . . . ?
C00H C00M C00N O003 -155.31(14) . . . . ?
C00H C00M C00N C00O 30.80(18) . . . . ?
C00I C00D C00H C004 143.48(12) . . . . ?
C00I C00D C00H C00M -29.07(15) . . . . ?
C00J C008 C00K C004 -167.75(11) . . . . ?
C00K C004 C00H C00D -1.8(2) . . . . ?
C00K C004 C00H C00M 170.84(12) . . . . ?
C00L C00M C00N O003 86.46(19) . . . . ?
C00L C00M C00N C00O -87.43(15) . . . . ?
C00M C00N C00O C00I 1.04(19) . . . . ?
C00P O002 C005 C006 -179.96(12) . . . . ?
C00P O002 C005 C00A 0.23(19) . . . . ?
C00Q C00M C00N O003 -28.6(2) . . . . ?
C00Q C00M C00N C00O 157.51(13) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.799
