# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_c_70m_3_2
_database_code_depnum_ccdc_archive 'CCDC 2246216'
loop_
_audit_author_name
_audit_author_address
'Zhao Huan'
;Jinan university
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-04
_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 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.95724(19)
_cell_length_b                   9.43219(18)
_cell_length_c                   22.4623(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1897.76(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11072
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.1050
_cell_measurement_theta_min      3.8880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16860
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.145
_diffrn_reflns_theta_min         3.936
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  35.00   1.00    1.00    --  -40.73  77.00  60.00  108
  2  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 150.00   99
  3  ω    -34.00  65.00   1.00    1.00    --   40.73 -38.00   0.00   99
  4  ω     79.00 178.00   1.00    1.92    --  108.20  61.00-120.00   99
  5  ω     79.00 178.00   1.00    1.92    --  108.20  61.00   0.00   99
  6  ω    101.00 178.00   1.00    1.92    --  108.20  95.00 100.00   77
  7  ω     26.00 109.00   1.00    1.92    --  108.20 -94.00 120.00   83
  8  ω     82.00 178.00   1.00    1.92    --  108.20  45.00 -30.00   96
  9  ω     76.00 178.00   1.00    1.92    --  108.20  77.00 150.00  102
 10  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00  60.00  100
 11  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00  100
 12  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00 -90.00   81
 13  ω     94.00 178.00   1.00    1.92    --  108.20 125.00-180.00   84
 14  ω     76.00 178.00   1.00    1.92    --  108.20  77.00  60.00  102
 15  ω   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 -60.00  109
 16  ω   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  30.00  109
 17  ω    -69.00  32.00   1.00    1.00    --  -40.98  57.00-150.00  101
 18  ω    -66.00   9.00   1.00    1.00    --  -40.98  38.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0825706000
_diffrn_orient_matrix_UB_12      0.1078311000
_diffrn_orient_matrix_UB_13      -0.0396043000
_diffrn_orient_matrix_UB_21      0.1259761000
_diffrn_orient_matrix_UB_22      0.1084861000
_diffrn_orient_matrix_UB_23      0.0102530000
_diffrn_orient_matrix_UB_31      0.0829605000
_diffrn_orient_matrix_UB_32      -0.0573718000
_diffrn_orient_matrix_UB_33      -0.0550437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3421
_reflns_number_total             3766
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.094
_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)+(0.0532P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1030
_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:
 C6(H6), C6'(H6'), C5(H5), C5'(H5')
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C7(H7A,H7B), C4'(H4'A,H4'B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10'(H10A,H10B,H10C), C10(H10D,H10E,H10F), C11'(H11A,
 H11B,H11C), C11(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O -0.48137(17) -0.2210(2) -0.05646(7) 0.0359(4) Uani 1 1 d . . . . .
O1 O -0.22979(18) -0.16081(19) -0.24119(7) 0.0362(4) Uani 1 1 d . . . . .
O3' O -0.37212(19) -0.3262(2) 0.02238(7) 0.0391(4) Uani 1 1 d . . . . .
O3 O -0.1064(2) -0.1523(2) -0.32893(8) 0.0474(5) Uani 1 1 d . . . . .
C9' C -0.4783(3) -0.1876(2) -0.11614(9) 0.0294(5) Uani 1 1 d . . . . .
C13 C -0.6151(2) -0.1482(2) -0.14069(10) 0.0293(5) Uani 1 1 d . . . . .
H13 H -0.7006 -0.1484 -0.1172 0.035 Uiso 1 1 calc R . . . .
C8' C -0.3495(2) -0.1940(3) -0.15005(9) 0.0295(5) Uani 1 1 d . . . . .
C8 C -0.4948(3) -0.1072(2) -0.23521(9) 0.0292(5) Uani 1 1 d . . . . .
C9 C -0.3608(2) -0.1511(2) -0.20981(10) 0.0291(5) Uani 1 1 d . . . . .
C2' C -0.3397(3) -0.2345(3) -0.02497(10) 0.0338(5) Uani 1 1 d . . . . .
C7' C -0.2043(3) -0.2448(3) -0.12431(10) 0.0368(5) Uani 1 1 d . . . . .
H7'A H -0.1357 -0.1656 -0.1211 0.044 Uiso 1 1 calc R . . . .
H7'B H -0.1603 -0.3143 -0.1509 0.044 Uiso 1 1 calc R . . . .
C6 C -0.3576(3) -0.0911(3) -0.33292(10) 0.0375(6) Uani 1 1 d . . . . .
H6 H -0.3495 -0.0257 -0.3667 0.045 Uiso 1 1 calc R . . . .
C12 C -0.6238(2) -0.1088(2) -0.20004(9) 0.0283(5) Uani 1 1 d . . . . .
C6' C -0.2264(3) -0.3109(3) -0.06307(10) 0.0336(5) Uani 1 1 d . . . . .
H6' H -0.1303 -0.3094 -0.0422 0.040 Uiso 1 1 calc R . . . .
C7 C -0.4986(3) -0.0554(3) -0.29858(10) 0.0362(5) Uani 1 1 d . . . . .
H7A H -0.5123 0.0466 -0.2986 0.043 Uiso 1 1 calc R . . . .
H7B H -0.5836 -0.0975 -0.3187 0.043 Uiso 1 1 calc R . . . .
C14 C -0.7730(3) -0.0656(3) -0.22622(10) 0.0340(5) Uani 1 1 d . . . . .
H14A H -0.8495 -0.0762 -0.1966 0.051 Uiso 1 1 calc GR . . . .
H14B H -0.7955 -0.1249 -0.2598 0.051 Uiso 1 1 calc GR . . . .
H14C H -0.7684 0.0315 -0.2388 0.051 Uiso 1 1 calc GR . . . .
C5 C -0.3455(3) -0.2427(3) -0.35651(11) 0.0421(6) Uani 1 1 d . . . . .
H5 H -0.3719 -0.3090 -0.3246 0.051 Uiso 1 1 calc R . . . .
C10' C -0.2936(3) -0.0920(3) -0.00042(13) 0.0461(6) Uani 1 1 d . . . . .
H10A H -0.2798 -0.0264 -0.0326 0.069 Uiso 1 1 calc GR . . . .
H10B H -0.2017 -0.1018 0.0212 0.069 Uiso 1 1 calc GR . . . .
H10C H -0.3699 -0.0572 0.0258 0.069 Uiso 1 1 calc GR . . . .
C2 C -0.2159(3) -0.0804(3) -0.29631(11) 0.0376(6) Uani 1 1 d . . . . .
C4' C -0.3474(3) -0.4695(3) 0.00255(11) 0.0440(6) Uani 1 1 d . . . . .
H4'A H -0.4402 -0.5225 0.0036 0.053 Uiso 1 1 calc R . . . .
H4'B H -0.2759 -0.5164 0.0283 0.053 Uiso 1 1 calc R . . . .
C10 C -0.1621(3) 0.0662(3) -0.28094(14) 0.0518(7) Uani 1 1 d . . . . .
H10D H -0.2347 0.1124 -0.2562 0.078 Uiso 1 1 calc GR . . . .
H10E H -0.1484 0.1199 -0.3168 0.078 Uiso 1 1 calc GR . . . .
H10F H -0.0690 0.0598 -0.2600 0.078 Uiso 1 1 calc GR . . . .
C5' C -0.2879(3) -0.4630(3) -0.06058(11) 0.0365(5) Uani 1 1 d . . . . .
H5' H -0.3718 -0.4709 -0.0884 0.044 Uiso 1 1 calc R . . . .
C11' C -0.1753(3) -0.5783(3) -0.07460(14) 0.0498(7) Uani 1 1 d . . . . .
H11A H -0.1386 -0.5658 -0.1144 0.075 Uiso 1 1 calc GR . . . .
H11B H -0.2225 -0.6694 -0.0713 0.075 Uiso 1 1 calc GR . . . .
H11C H -0.0937 -0.5728 -0.0470 0.075 Uiso 1 1 calc GR . . . .
C4 C -0.1782(3) -0.2525(3) -0.36827(12) 0.0497(7) Uani 1 1 d . . . . .
H4A H -0.1426 -0.3478 -0.3603 0.060 Uiso 1 1 calc R . . . .
H4B H -0.1566 -0.2294 -0.4095 0.060 Uiso 1 1 calc R . . . .
C11 C -0.4416(4) -0.2742(4) -0.41081(13) 0.0609(9) Uani 1 1 d . . . . .
H11D H -0.5445 -0.2567 -0.4014 0.091 Uiso 1 1 calc GR . . . .
H11E H -0.4292 -0.3716 -0.4221 0.091 Uiso 1 1 calc GR . . . .
H11F H -0.4116 -0.2140 -0.4431 0.091 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
O1' C9' 1.377(3) . ?
O1' C2' 1.459(3) . ?
O1 C9 1.372(3) . ?
O1 C2 1.457(3) . ?
O3' C2' 1.402(3) . ?
O3' C4' 1.440(3) . ?
O3 C2 1.400(3) . ?
O3 C4 1.445(4) . ?
C9' C13 1.394(3) . ?
C9' C8' 1.384(3) . ?
C13 C12 1.386(3) . ?
C8' C9 1.406(3) . ?
C8' C7' 1.502(3) . ?
C8 C9 1.392(3) . ?
C8 C12 1.400(3) . ?
C8 C7 1.505(3) . ?
C2' C6' 1.511(3) . ?
C2' C10' 1.510(4) . ?
C7' C6' 1.523(3) . ?
C6 C7 1.517(3) . ?
C6 C5 1.529(4) . ?
C6 C2 1.516(4) . ?
C12 C14 1.515(3) . ?
C6' C5' 1.537(4) . ?
C5 C4 1.525(4) . ?
C5 C11 1.522(4) . ?
C2 C10 1.504(4) . ?
C4' C5' 1.516(3) . ?
C5' C11' 1.517(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9' O1' C2' 118.34(17) . . ?
C9 O1 C2 118.34(17) . . ?
C2' O3' C4' 108.24(18) . . ?
C2 O3 C4 109.0(2) . . ?
O1' C9' C13 115.38(19) . . ?
O1' C9' C8' 122.85(19) . . ?
C8' C9' C13 121.77(19) . . ?
C12 C13 C9' 120.1(2) . . ?
C9' C8' C9 116.96(19) . . ?
C9' C8' C7' 121.59(19) . . ?
C9 C8' C7' 121.45(19) . . ?
C9 C8 C12 118.49(19) . . ?
C9 C8 C7 120.2(2) . . ?
C12 C8 C7 121.3(2) . . ?
O1 C9 C8' 114.19(19) . . ?
O1 C9 C8 123.15(19) . . ?
C8 C9 C8' 122.62(19) . . ?
O1' C2' C6' 110.57(18) . . ?
O1' C2' C10' 109.7(2) . . ?
O3' C2' O1' 103.97(18) . . ?
O3' C2' C6' 105.9(2) . . ?
O3' C2' C10' 109.2(2) . . ?
C10' C2' C6' 116.6(2) . . ?
C8' C7' C6' 111.47(19) . . ?
C7 C6 C5 116.3(2) . . ?
C2 C6 C7 113.97(19) . . ?
C2 C6 C5 101.0(2) . . ?
C13 C12 C8 120.0(2) . . ?
C13 C12 C14 119.7(2) . . ?
C8 C12 C14 120.37(19) . . ?
C2' C6' C7' 113.8(2) . . ?
C2' C6' C5' 100.59(19) . . ?
C7' C6' C5' 117.5(2) . . ?
C8 C7 C6 112.97(19) . . ?
C4 C5 C6 100.7(2) . . ?
C11 C5 C6 114.8(2) . . ?
C11 C5 C4 113.9(2) . . ?
O1 C2 C6 110.7(2) . . ?
O1 C2 C10 108.1(2) . . ?
O3 C2 O1 104.60(18) . . ?
O3 C2 C6 105.7(2) . . ?
O3 C2 C10 110.0(2) . . ?
C10 C2 C6 117.0(2) . . ?
O3' C4' C5' 107.8(2) . . ?
C4' C5' C6' 101.4(2) . . ?
C4' C5' C11' 113.5(2) . . ?
C11' C5' C6' 115.0(2) . . ?
O3 C4 C5 107.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.147
_oxdiff_exptl_absorpt_empirical_full_min 0.672
####################################################################### 
# 
# 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_70m-2-4-2
_database_code_depnum_ccdc_archive 'CCDC 2246217'
loop_
_audit_author_name
_audit_author_address
'Zhao Huan'
;Jinan university
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-04
_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 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.75334(11)
_cell_length_b                   12.14604(19)
_cell_length_c                   19.6200(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1847.66(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6130
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.2700
_cell_measurement_theta_min      3.5900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7587
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.302
_diffrn_reflns_theta_min         4.281
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  32.00   1.00    1.00    --  -40.73  57.00   0.00  101
  2  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00-150.00   81
  3  ω    -34.00  65.00   1.00    1.00    --   40.73 -38.00   0.00   99
  4  ω     94.00 178.00   1.00    1.00    --  106.95 125.00   0.00   84
  5  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-120.00   84
  6  ω     54.00 178.00   1.00    1.00    --  106.95  15.00-150.00  124
  7  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 -90.00   99
  8  ω     35.00  63.00   1.00    1.00    --  106.95 -61.00  90.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1613177000
_diffrn_orient_matrix_UB_12      -0.0300087000
_diffrn_orient_matrix_UB_13      -0.0421282000
_diffrn_orient_matrix_UB_21      -0.0960284000
_diffrn_orient_matrix_UB_22      0.0319152000
_diffrn_orient_matrix_UB_23      -0.0658389000
_diffrn_orient_matrix_UB_31      0.0662879000
_diffrn_orient_matrix_UB_32      0.1188345000
_diffrn_orient_matrix_UB_33      0.0070283000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                3308
_reflns_number_total             3404
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.089
_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)+(0.0609P)²+0.2449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1012
_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:
 C5'(H5'), C6'(H6'), C6(H6), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C7(H7A,H7B), C4'(H4'A,H4'B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10'(H10A,H10B,H10C), C11(H11A,H11B,H11C), C11'(H11D,
 H11E,H11F), C10(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2264(2) 0.54859(12) 0.20816(7) 0.0390(4) Uani 1 1 d . . . . .
C12 C 0.0831(2) 0.36133(16) 0.34549(11) 0.0312(4) Uani 1 1 d . . . . .
O3' O -0.3523(2) 0.64527(14) 0.41446(10) 0.0547(5) Uani 1 1 d . . . . .
O1' O -0.0579(2) 0.62848(13) 0.41232(9) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.1554(2) 0.50573(17) 0.26641(10) 0.0303(4) Uani 1 1 d . . . . .
C13 C 0.0764(3) 0.58278(16) 0.30832(11) 0.0334(4) Uani 1 1 d . . . . .
H13 H 0.0715 0.6564 0.2955 0.040 Uiso 1 1 calc R . . . .
C5' C -0.3811(2) 0.45348(18) 0.41025(10) 0.0343(4) Uani 1 1 d . . . . .
H5' H -0.3249 0.4399 0.3663 0.041 Uiso 1 1 calc R . . . .
C8 C 0.1616(2) 0.39455(16) 0.28397(11) 0.0308(4) Uani 1 1 d . . . . .
C7' C -0.0775(3) 0.41329(18) 0.45631(10) 0.0357(4) Uani 1 1 d . . . . .
H7'A H 0.0009 0.4308 0.4933 0.043 Uiso 1 1 calc R . . . .
H7'B H -0.1054 0.3356 0.4589 0.043 Uiso 1 1 calc R . . . .
C14 C 0.0798(3) 0.24026(17) 0.36417(12) 0.0422(5) Uani 1 1 d . . . . .
H14A H 0.1210 0.1974 0.3264 0.063 Uiso 1 1 calc GR . . . .
H14B H -0.0362 0.2187 0.3749 0.063 Uiso 1 1 calc GR . . . .
H14C H 0.1524 0.2279 0.4031 0.063 Uiso 1 1 calc GR . . . .
O3 O 0.4355(3) 0.53206(15) 0.12856(9) 0.0590(5) Uani 1 1 d . . . . .
C2 C 0.2966(3) 0.47520(19) 0.15687(10) 0.0403(5) Uani 1 1 d . . . . .
C6' C -0.2422(3) 0.48205(17) 0.46284(9) 0.0311(4) Uani 1 1 d . . . . .
H6' H -0.2901 0.4714 0.5086 0.037 Uiso 1 1 calc R . . . .
C9' C 0.0055(3) 0.54883(17) 0.36915(10) 0.0340(4) Uani 1 1 d . . . . .
C7 C 0.2539(3) 0.31520(18) 0.23744(13) 0.0433(5) Uani 1 1 d . . . . .
H7A H 0.1695 0.2738 0.2115 0.052 Uiso 1 1 calc R . . . .
H7B H 0.3194 0.2634 0.2647 0.052 Uiso 1 1 calc R . . . .
C2' C -0.2095(3) 0.60553(17) 0.45173(10) 0.0333(4) Uani 1 1 d . . . . .
C8' C 0.0071(2) 0.43834(17) 0.38886(10) 0.0305(4) Uani 1 1 d . . . . .
C6 C 0.3749(3) 0.37385(17) 0.18862(10) 0.0308(4) Uani 1 1 d . . . . .
H6 H 0.4062 0.3226 0.1521 0.037 Uiso 1 1 calc R . . . .
C5 C 0.5399(3) 0.4193(2) 0.21973(11) 0.0391(5) Uani 1 1 d . . . . .
H5 H 0.5134 0.4491 0.2650 0.047 Uiso 1 1 calc R . . . .
C10' C -0.1881(4) 0.6721(2) 0.51587(12) 0.0516(6) Uani 1 1 d . . . . .
H10A H -0.1565 0.7462 0.5043 0.077 Uiso 1 1 calc GR . . . .
H10B H -0.0994 0.6399 0.5436 0.077 Uiso 1 1 calc GR . . . .
H10C H -0.2948 0.6727 0.5407 0.077 Uiso 1 1 calc GR . . . .
C4' C -0.4782(3) 0.5613(2) 0.40586(12) 0.0425(5) Uani 1 1 d . . . . .
H4'A H -0.5346 0.5683 0.3619 0.051 Uiso 1 1 calc R . . . .
H4'B H -0.5649 0.5656 0.4414 0.051 Uiso 1 1 calc R . . . .
C4 C 0.5818(4) 0.5145(2) 0.17198(16) 0.0602(7) Uani 1 1 d . . . . .
H4A H 0.6060 0.5805 0.1981 0.072 Uiso 1 1 calc R . . . .
H4B H 0.6827 0.4970 0.1448 0.072 Uiso 1 1 calc R . . . .
C11 C 0.6845(3) 0.3360(3) 0.22656(15) 0.0632(8) Uani 1 1 d . . . . .
H11A H 0.6502 0.2789 0.2575 0.095 Uiso 1 1 calc GR . . . .
H11B H 0.7858 0.3720 0.2437 0.095 Uiso 1 1 calc GR . . . .
H11C H 0.7090 0.3045 0.1827 0.095 Uiso 1 1 calc GR . . . .
C11' C -0.4906(4) 0.3541(2) 0.42808(15) 0.0532(6) Uani 1 1 d . . . . .
H11D H -0.4195 0.2894 0.4289 0.080 Uiso 1 1 calc GR . . . .
H11E H -0.5797 0.3453 0.3945 0.080 Uiso 1 1 calc GR . . . .
H11F H -0.5421 0.3647 0.4721 0.080 Uiso 1 1 calc GR . . . .
C10 C 0.1612(5) 0.4565(3) 0.10309(16) 0.0896(13) Uani 1 1 d . . . . .
H10D H 0.0620 0.4224 0.1234 0.134 Uiso 1 1 calc GR . . . .
H10E H 0.2068 0.4094 0.0682 0.134 Uiso 1 1 calc GR . . . .
H10F H 0.1284 0.5258 0.0835 0.134 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
O1 C9 1.371(2) . ?
O1 C2 1.450(2) . ?
C12 C8 1.411(3) . ?
C12 C14 1.516(3) . ?
C12 C8' 1.395(3) . ?
O3' C2' 1.412(3) . ?
O3' C4' 1.422(3) . ?
O1' C9' 1.376(3) . ?
O1' C2' 1.434(3) . ?
C9 C13 1.388(3) . ?
C9 C8 1.394(3) . ?
C13 C9' 1.377(3) . ?
C5' C6' 1.532(3) . ?
C5' C4' 1.512(3) . ?
C5' C11' 1.517(3) . ?
C8 C7 1.508(3) . ?
C7' C6' 1.531(3) . ?
C7' C8' 1.508(3) . ?
O3 C2 1.395(3) . ?
O3 C4 1.435(4) . ?
C2 C6 1.507(3) . ?
C2 C10 1.506(4) . ?
C6' C2' 1.537(3) . ?
C9' C8' 1.397(3) . ?
C7 C6 1.518(3) . ?
C2' C10' 1.505(3) . ?
C6 C5 1.521(3) . ?
C5 C4 1.523(4) . ?
C5 C11 1.516(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C2 119.71(15) . . ?
C8 C12 C14 119.45(18) . . ?
C8' C12 C8 120.82(18) . . ?
C8' C12 C14 119.72(18) . . ?
C2' O3' C4' 110.76(17) . . ?
C9' O1' C2' 119.17(17) . . ?
O1 C9 C13 114.52(17) . . ?
O1 C9 C8 124.02(18) . . ?
C13 C9 C8 121.46(18) . . ?
C9' C13 C9 119.18(18) . . ?
C4' C5' C6' 101.09(17) . . ?
C4' C5' C11' 115.07(19) . . ?
C11' C5' C6' 114.75(18) . . ?
C12 C8 C7 122.68(18) . . ?
C9 C8 C12 118.25(18) . . ?
C9 C8 C7 119.07(18) . . ?
C8' C7' C6' 109.02(16) . . ?
C2 O3 C4 107.49(17) . . ?
O1 C2 C6 111.50(15) . . ?
O1 C2 C10 108.5(2) . . ?
O3 C2 O1 105.16(18) . . ?
O3 C2 C6 104.93(18) . . ?
O3 C2 C10 109.5(2) . . ?
C10 C2 C6 116.6(2) . . ?
C5' C6' C2' 103.98(16) . . ?
C7' C6' C5' 114.00(17) . . ?
C7' C6' C2' 112.51(18) . . ?
O1' C9' C13 117.72(18) . . ?
O1' C9' C8' 120.55(18) . . ?
C13 C9' C8' 121.60(19) . . ?
C8 C7 C6 112.05(17) . . ?
O3' C2' O1' 107.28(16) . . ?
O3' C2' C6' 106.13(18) . . ?
O3' C2' C10' 109.61(19) . . ?
O1' C2' C6' 113.67(17) . . ?
O1' C2' C10' 104.83(19) . . ?
C10' C2' C6' 115.09(17) . . ?
C12 C8' C7' 125.71(18) . . ?
C12 C8' C9' 118.63(18) . . ?
C9' C8' C7' 115.66(18) . . ?
C2 C6 C7 113.24(18) . . ?
C2 C6 C5 102.03(18) . . ?
C7 C6 C5 115.89(18) . . ?
C6 C5 C4 102.0(2) . . ?
C11 C5 C6 114.5(2) . . ?
C11 C5 C4 113.8(2) . . ?
O3' C4' C5' 105.83(17) . . ?
O3 C4 C5 108.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.716
####################################################################### 
# 
# 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_ahk-4
_database_code_depnum_ccdc_archive 'CCDC 2246219'
loop_
_audit_author_name
_audit_author_address
'Zhao Huan'
;Jinan university
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-04
_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         '2(C15 H20 O3)'
_chemical_formula_sum            'C30 H40 O6'
_chemical_formula_weight         496.62
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.35263(13)
_cell_length_b                   15.2684(2)
_cell_length_c                   9.55302(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.5004(15)
_cell_angle_gamma                90
_cell_volume                     1364.12(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12380
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.4390
_cell_measurement_theta_min      2.8480
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16884
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.988
_diffrn_reflns_theta_min         4.629
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -40.73 125.00  30.00   94
  2  ω    -69.00  32.00   1.00    1.00    --  -40.73  57.00 -60.00  101
  3  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
  4  ω     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
  5  ω     81.00 178.00   1.00    1.00    --  106.95  45.00-180.00   97
  6  ω     31.00 140.00   1.00    1.00    --  106.95 -77.00   0.00  109
  7  ω     74.00 178.00   1.00    1.00    --  106.95  77.00 120.00  104
  8  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -30.00  100
  9  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00-150.00  100
 10  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -30.00   97
 11  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
 12  ω     25.00 109.00   1.00    1.00    --  106.95 -95.00-180.00   84
 13  ω     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
 14  ω   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00  90.00  100
 15  ω   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00-180.00  109
 16  ω     81.00 178.00   1.00    1.00    --  106.95  45.00  90.00   97
 17  ω     78.00 178.00   1.00    1.00    --  106.95  61.00   0.00  100
 18  ω     74.00 178.00   1.00    1.00    --  106.95  77.00 -90.00  104
 19  ω     74.00 178.00   1.00    1.00    --  106.95  77.00-150.00  104
 20  ω    -65.00  34.00   1.00    1.00    --  -40.73  38.00-120.00   99
 21  ω   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 -60.00  109
 22  ω     34.00  73.00   1.00    1.00    --  106.95-125.00 -60.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1139022000
_diffrn_orient_matrix_UB_12      -0.0543334000
_diffrn_orient_matrix_UB_13      0.0767941000
_diffrn_orient_matrix_UB_21      -0.1188077000
_diffrn_orient_matrix_UB_22      0.0568719000
_diffrn_orient_matrix_UB_23      -0.0660609000
_diffrn_orient_matrix_UB_31      -0.0090154000
_diffrn_orient_matrix_UB_32      -0.0631484000
_diffrn_orient_matrix_UB_33      -0.1254146000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5216
_reflns_number_total             5393
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 2345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_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     333
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0378
_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)+(0.0588P)²+0.0810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0972
_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:
 C6'(H6'), C5'(H5'), C6(H6), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C4'(H4'A,H4'B), C7(H7A,H7B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13'(H13'), C15'(H15'), C15(H15), C13(H13)
2.d Idealised Me refined as rotating group:
 C16'(H16A,H16B,H16C), C10'(H10A,H10B,H10C), C11'(H11A,H11B,H11C), C17'(H17A,
 H17B,H17C), C16(H16D,H16E,H16F), C17(H17D,H17E,H17F), C10(H10D,H10E,H10F),
 C11(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O -0.19463(14) -0.38408(10) -0.24578(14) 0.0328(3) Uani 1 1 d . . . . .
O3' O -0.09506(17) -0.40010(11) -0.45883(15) 0.0368(3) Uani 1 1 d . . . . .
C8' C -0.0762(2) -0.29842(13) -0.0644(2) 0.0278(4) Uani 1 1 d . . . . .
O4' O -0.45749(18) -0.30805(13) 0.15874(17) 0.0458(4) Uani 1 1 d . . . . .
C9' C -0.1944(2) -0.34255(13) -0.1189(2) 0.0272(4) Uani 1 1 d . . . . .
C12' C -0.0913(2) -0.25754(13) 0.0663(2) 0.0310(4) Uani 1 1 d . . . . .
C13' C -0.2198(2) -0.26167(14) 0.1367(2) 0.0340(4) Uani 1 1 d . . . . .
H13' H -0.2287 -0.2341 0.2230 0.041 Uiso 1 1 calc R . . . .
C15' C -0.3254(2) -0.34669(14) -0.0493(2) 0.0307(4) Uani 1 1 d . . . . .
H15' H -0.4032 -0.3756 -0.0892 0.037 Uiso 1 1 calc R . . . .
C7' C 0.0618(2) -0.29589(16) -0.1445(2) 0.0350(5) Uani 1 1 d . . . . .
H7'A H 0.1302 -0.3354 -0.1009 0.042 Uiso 1 1 calc R . . . .
H7'B H 0.1012 -0.2372 -0.1404 0.042 Uiso 1 1 calc R . . . .
C14' C -0.3363(2) -0.30687(14) 0.0795(2) 0.0330(4) Uani 1 1 d . . . . .
C2' C -0.0592(2) -0.39939(14) -0.3163(2) 0.0294(4) Uani 1 1 d . . . . .
C16' C 0.0338(3) -0.20928(17) 0.1301(2) 0.0421(5) Uani 1 1 d . . . . .
H16A H 0.1122 -0.2491 0.1435 0.063 Uiso 1 1 calc GR . . . .
H16B H 0.0066 -0.1852 0.2188 0.063 Uiso 1 1 calc GR . . . .
H16C H 0.0624 -0.1628 0.0687 0.063 Uiso 1 1 calc GR . . . .
C6' C 0.0399(2) -0.32209(14) -0.2967(2) 0.0306(4) Uani 1 1 d . . . . .
H6' H 0.1332 -0.3374 -0.3357 0.037 Uiso 1 1 calc R . . . .
C5' C -0.0299(2) -0.25362(15) -0.3918(2) 0.0369(5) Uani 1 1 d . . . . .
H5' H -0.1082 -0.2253 -0.3414 0.044 Uiso 1 1 calc R . . . .
C10' C -0.0037(3) -0.48793(15) -0.2740(3) 0.0399(5) Uani 1 1 d . . . . .
H10A H 0.0142 -0.4887 -0.1749 0.060 Uiso 1 1 calc GR . . . .
H10B H 0.0836 -0.4998 -0.3227 0.060 Uiso 1 1 calc GR . . . .
H10C H -0.0733 -0.5318 -0.2975 0.060 Uiso 1 1 calc GR . . . .
C11' C 0.0735(4) -0.18394(19) -0.4423(3) 0.0570(7) Uani 1 1 d . . . . .
H11A H 0.1152 -0.1544 -0.3632 0.086 Uiso 1 1 calc GR . . . .
H11B H 0.0231 -0.1424 -0.4997 0.086 Uiso 1 1 calc GR . . . .
H11C H 0.1477 -0.2110 -0.4961 0.086 Uiso 1 1 calc GR . . . .
C4' C -0.0926(3) -0.31067(18) -0.5092(2) 0.0439(5) Uani 1 1 d . . . . .
H4'A H -0.1887 -0.2914 -0.5328 0.053 Uiso 1 1 calc R . . . .
H4'B H -0.0341 -0.3064 -0.5923 0.053 Uiso 1 1 calc R . . . .
C17' C -0.5795(3) -0.3519(2) 0.1019(3) 0.0481(6) Uani 1 1 d . . . . .
H17A H -0.6032 -0.3273 0.0122 0.072 Uiso 1 1 calc GR . . . .
H17B H -0.6589 -0.3448 0.1639 0.072 Uiso 1 1 calc GR . . . .
H17C H -0.5586 -0.4131 0.0914 0.072 Uiso 1 1 calc GR . . . .
O4 O -0.02925(17) -0.05154(12) -0.13269(18) 0.0424(4) Uani 1 1 d . . . . .
C8 C -0.4208(2) -0.03395(14) -0.3437(2) 0.0323(4) Uani 1 1 d . . . . .
O1 O -0.30201(16) 0.05794(13) -0.51582(17) 0.0454(4) Uani 1 1 d . . . . .
O3 O -0.40083(17) 0.07498(11) -0.73103(16) 0.0399(4) Uani 1 1 d . . . . .
C12 C -0.4039(2) -0.08374(14) -0.2211(2) 0.0321(4) Uani 1 1 d . . . . .
C15 C -0.1681(2) 0.00554(15) -0.3288(2) 0.0316(4) Uani 1 1 d . . . . .
H15 H -0.0899 0.0351 -0.3653 0.038 Uiso 1 1 calc R . . . .
C13 C -0.2719(2) -0.08843(14) -0.1543(2) 0.0339(4) Uani 1 1 d . . . . .
H13 H -0.2613 -0.1220 -0.0737 0.041 Uiso 1 1 calc R . . . .
C14 C -0.1549(2) -0.04311(14) -0.2075(2) 0.0320(4) Uani 1 1 d . . . . .
C16 C -0.5301(2) -0.13151(17) -0.1594(3) 0.0418(5) Uani 1 1 d . . . . .
H16D H -0.6050 -0.0904 -0.1401 0.063 Uiso 1 1 calc GR . . . .
H16E H -0.5011 -0.1599 -0.0741 0.063 Uiso 1 1 calc GR . . . .
H16F H -0.5642 -0.1746 -0.2248 0.063 Uiso 1 1 calc GR . . . .
C7 C -0.5636(2) -0.02311(18) -0.4179(3) 0.0415(5) Uani 1 1 d . . . . .
H7A H -0.6200 0.0205 -0.3693 0.050 Uiso 1 1 calc R . . . .
H7B H -0.6153 -0.0781 -0.4154 0.050 Uiso 1 1 calc R . . . .
C9 C -0.3015(2) 0.00938(15) -0.3954(2) 0.0323(4) Uani 1 1 d . . . . .
C17 C 0.0851(2) 0.00552(17) -0.1697(3) 0.0429(5) Uani 1 1 d . . . . .
H17D H 0.1152 -0.0073 -0.2633 0.064 Uiso 1 1 calc GR . . . .
H17E H 0.1638 -0.0029 -0.1060 0.064 Uiso 1 1 calc GR . . . .
H17F H 0.0532 0.0652 -0.1647 0.064 Uiso 1 1 calc GR . . . .
C2 C -0.4358(2) 0.07742(16) -0.5884(2) 0.0350(5) Uani 1 1 d . . . . .
C6 C -0.5443(2) 0.00496(16) -0.5692(2) 0.0348(5) Uani 1 1 d . . . . .
H6 H -0.6367 0.0259 -0.6047 0.042 Uiso 1 1 calc R . . . .
C4 C -0.4113(3) -0.01421(18) -0.7795(3) 0.0462(6) Uani 1 1 d . . . . .
H4A H -0.3166 -0.0385 -0.7932 0.055 Uiso 1 1 calc R . . . .
H4B H -0.4629 -0.0165 -0.8680 0.055 Uiso 1 1 calc R . . . .
C5 C -0.4910(2) -0.06638(17) -0.6684(3) 0.0414(5) Uani 1 1 d . . . . .
H5 H -0.4232 -0.1043 -0.6183 0.050 Uiso 1 1 calc R . . . .
C10 C -0.4820(3) 0.16830(18) -0.5502(3) 0.0462(6) Uani 1 1 d . . . . .
H10D H -0.5033 0.1706 -0.4522 0.069 Uiso 1 1 calc GR . . . .
H10E H -0.5657 0.1837 -0.6036 0.069 Uiso 1 1 calc GR . . . .
H10F H -0.4064 0.2088 -0.5705 0.069 Uiso 1 1 calc GR . . . .
C11 C -0.6104(3) -0.1221(2) -0.7308(4) 0.0625(8) Uani 1 1 d . . . . .
H11D H -0.6604 -0.1513 -0.6570 0.094 Uiso 1 1 calc GR . . . .
H11E H -0.5704 -0.1648 -0.7930 0.094 Uiso 1 1 calc GR . . . .
H11F H -0.6757 -0.0852 -0.7819 0.094 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
O1' C9' 1.368(2) . ?
O1' C2' 1.459(2) . ?
O3' C2' 1.399(2) . ?
O3' C4' 1.448(3) . ?
C8' C9' 1.392(3) . ?
C8' C12' 1.403(3) . ?
C8' C7' 1.507(3) . ?
O4' C14' 1.368(3) . ?
O4' C17' 1.426(3) . ?
C9' C15' 1.401(3) . ?
C12' C13' 1.384(3) . ?
C12' C16' 1.507(3) . ?
C13' C14' 1.397(3) . ?
C15' C14' 1.377(3) . ?
C7' C6' 1.520(3) . ?
C2' C6' 1.512(3) . ?
C2' C10' 1.502(3) . ?
C6' C5' 1.528(3) . ?
C5' C11' 1.520(3) . ?
C5' C4' 1.533(3) . ?
O4 C14 1.376(2) . ?
O4 C17 1.426(3) . ?
C8 C12 1.404(3) . ?
C8 C7 1.515(3) . ?
C8 C9 1.392(3) . ?
O1 C9 1.368(3) . ?
O1 C2 1.456(2) . ?
O3 C2 1.405(3) . ?
O3 C4 1.441(3) . ?
C12 C13 1.387(3) . ?
C12 C16 1.511(3) . ?
C15 C14 1.381(3) . ?
C15 C9 1.397(3) . ?
C13 C14 1.394(3) . ?
C7 C6 1.520(3) . ?
C2 C6 1.513(3) . ?
C2 C10 1.499(4) . ?
C6 C5 1.530(4) . ?
C4 C5 1.527(4) . ?
C5 C11 1.521(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9' O1' C2' 119.26(14) . . ?
C2' O3' C4' 108.16(17) . . ?
C9' C8' C12' 117.55(18) . . ?
C9' C8' C7' 120.19(17) . . ?
C12' C8' C7' 122.25(18) . . ?
C14' O4' C17' 117.35(18) . . ?
O1' C9' C8' 123.48(17) . . ?
O1' C9' C15' 113.87(17) . . ?
C8' C9' C15' 122.64(18) . . ?
C8' C12' C16' 119.56(19) . . ?
C13' C12' C8' 120.45(19) . . ?
C13' C12' C16' 120.00(19) . . ?
C12' C13' C14' 120.65(18) . . ?
C14' C15' C9' 118.41(19) . . ?
C8' C7' C6' 111.74(17) . . ?
O4' C14' C13' 115.90(19) . . ?
O4' C14' C15' 123.8(2) . . ?
C15' C14' C13' 120.28(19) . . ?
O1' C2' C6' 110.58(16) . . ?
O1' C2' C10' 108.64(17) . . ?
O3' C2' O1' 104.43(15) . . ?
O3' C2' C6' 105.57(17) . . ?
O3' C2' C10' 109.51(18) . . ?
C10' C2' C6' 117.32(17) . . ?
C7' C6' C5' 116.23(18) . . ?
C2' C6' C7' 113.69(17) . . ?
C2' C6' C5' 101.65(17) . . ?
C6' C5' C4' 101.84(18) . . ?
C11' C5' C6' 113.5(2) . . ?
C11' C5' C4' 113.9(2) . . ?
O3' C4' C5' 107.44(18) . . ?
C14 O4 C17 116.93(18) . . ?
C12 C8 C7 122.80(19) . . ?
C9 C8 C12 117.96(19) . . ?
C9 C8 C7 119.21(19) . . ?
C9 O1 C2 120.52(16) . . ?
C2 O3 C4 108.73(17) . . ?
C8 C12 C16 120.26(19) . . ?
C13 C12 C8 120.31(19) . . ?
C13 C12 C16 119.42(19) . . ?
C14 C15 C9 118.57(19) . . ?
C12 C13 C14 120.38(19) . . ?
O4 C14 C15 123.78(19) . . ?
O4 C14 C13 115.72(18) . . ?
C15 C14 C13 120.49(18) . . ?
C8 C7 C6 111.36(17) . . ?
C8 C9 C15 122.27(19) . . ?
O1 C9 C8 123.99(18) . . ?
O1 C9 C15 113.73(18) . . ?
O1 C2 C6 111.55(18) . . ?
O1 C2 C10 108.8(2) . . ?
O3 C2 O1 104.50(16) . . ?
O3 C2 C6 105.07(18) . . ?
O3 C2 C10 109.28(19) . . ?
C10 C2 C6 116.89(19) . . ?
C7 C6 C5 115.5(2) . . ?
C2 C6 C7 114.00(19) . . ?
C2 C6 C5 102.88(18) . . ?
O3 C4 C5 107.6(2) . . ?
C4 C5 C6 102.9(2) . . ?
C11 C5 C6 113.5(2) . . ?
C11 C5 C4 112.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.016
_oxdiff_exptl_absorpt_empirical_full_min 0.647
####################################################################### 
# 
# 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_c70m-2-4-1
_database_code_depnum_ccdc_archive 'CCDC 2246220'
loop_
_audit_author_name
_audit_author_address
'Zhao Huan'
;Jinan university
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-04
_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 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6389(2)
_cell_length_b                   11.9203(2)
_cell_length_c                   12.9914(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.143(2)
_cell_angle_gamma                90
_cell_volume                     1859.97(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6950
_cell_measurement_theta_min      3.6820
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.801
_diffrn_reflns_theta_min         3.680
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -41.11 125.00  90.00   94
  2  ω   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00 -30.00   98
  3  ω      9.00 117.00   1.00    1.00    --   41.11  77.00  90.00  108
  4  ω     17.00 115.00   1.00    1.00    --   41.11  38.00 -90.00   98
  5  ω      1.00  82.00   1.00    1.00    --   41.11 -99.00 -30.00   81
  6  ω     31.00 136.00   1.00    1.85    --  107.58 -30.00 150.00  105
  7  ω     34.00 122.00   1.00    1.85    --  107.58-125.00 -30.00   88
  8  ω     31.00 136.00   1.00    1.85    --  107.58 -30.00 -30.00  105
  9  ω     82.00 178.00   1.00    1.85    --  107.58  45.00 -30.00   96
 10  ω     82.00 178.00   1.00    1.85    --  107.58  45.00 150.00   96
 11  ω     79.00 178.00   1.00    1.85    --  107.58  30.00-150.00   99
 12  ω     25.00 110.00   1.00    1.85    --  107.58 -95.00  90.00   85
 13  ω     25.00  89.00   1.00    1.85    --  107.58 -95.00  30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0776191000
_diffrn_orient_matrix_UB_12      0.1028371000
_diffrn_orient_matrix_UB_13      -0.0196110000
_diffrn_orient_matrix_UB_21      -0.1012750000
_diffrn_orient_matrix_UB_22      -0.0767604000
_diffrn_orient_matrix_UB_23      -0.0489885000
_diffrn_orient_matrix_UB_31      -0.0132447000
_diffrn_orient_matrix_UB_32      -0.0154012000
_diffrn_orient_matrix_UB_33      0.1130608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3298
_reflns_number_total             3674
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.028
_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)+(0.0510P)²+0.6239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1055
_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:
 C6'(H6'), C6(H6), C5(H5), C5'(H5')
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C7(H7A,H7B), C4(H4A,H4B), C4'(H4'A,H4'B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10'(H10A,H10B,H10C), C11'(H11A,H11B,H11C), C11(H11D,
 H11E,H11F), C10(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O -0.00435(7) 0.19692(7) 0.15328(7) 0.0278(2) Uani 1 1 d . . . . .
O1 O -0.32444(8) 0.06411(7) 0.21449(8) 0.0320(2) Uani 1 1 d . . . . .
O3' O 0.16829(7) 0.23073(8) 0.14282(7) 0.0299(2) Uani 1 1 d . . . . .
O3 O -0.43836(8) -0.04112(9) 0.27877(8) 0.0387(2) Uani 1 1 d . . . . .
C8' C -0.08132(10) 0.31128(10) 0.26941(10) 0.0227(3) Uani 1 1 d . . . . .
C13 C -0.16887(10) 0.14034(10) 0.18266(10) 0.0232(3) Uani 1 1 d . . . . .
H13 H -0.1715 0.0808 0.1357 0.028 Uiso 1 1 calc R . . . .
C12 C -0.16626(10) 0.32282(10) 0.31716(10) 0.0225(2) Uani 1 1 d . . . . .
C9' C -0.08435(10) 0.21912(10) 0.20224(9) 0.0221(2) Uani 1 1 d . . . . .
C8 C -0.25039(10) 0.24193(10) 0.30148(10) 0.0229(3) Uani 1 1 d . . . . .
C6' C 0.10773(10) 0.35257(10) 0.25225(10) 0.0245(3) Uani 1 1 d . . . . .
H6' H 0.1515 0.4171 0.2420 0.029 Uiso 1 1 calc R . . . .
C9 C -0.24953(10) 0.15121(10) 0.23388(10) 0.0234(3) Uani 1 1 d . . . . .
C7' C 0.01153(10) 0.39616(10) 0.28806(11) 0.0281(3) Uani 1 1 d . . . . .
H7'A H 0.0388 0.4149 0.3645 0.034 Uiso 1 1 calc R . . . .
H7'B H -0.0175 0.4642 0.2483 0.034 Uiso 1 1 calc R . . . .
C1' C 0.07177(10) 0.28605(10) 0.14740(10) 0.0252(3) Uani 1 1 d . . . . .
C14 C -0.16484(11) 0.42334(10) 0.38846(11) 0.0290(3) Uani 1 1 d . . . . .
H14A H -0.1179 0.4078 0.4608 0.044 Uiso 1 1 calc GR . . . .
H14B H -0.2391 0.4387 0.3893 0.044 Uiso 1 1 calc GR . . . .
H14C H -0.1366 0.4873 0.3606 0.044 Uiso 1 1 calc GR . . . .
C6 C -0.39275(10) 0.13405(11) 0.35841(10) 0.0263(3) Uani 1 1 d . . . . .
H6 H -0.4615 0.1444 0.3770 0.032 Uiso 1 1 calc R . . . .
C7 C -0.34042(11) 0.24870(11) 0.35553(11) 0.0291(3) Uani 1 1 d . . . . .
H7A H -0.3975 0.3011 0.3162 0.035 Uiso 1 1 calc R . . . .
H7B H -0.3086 0.2765 0.4289 0.035 Uiso 1 1 calc R . . . .
C4 C -0.37089(12) -0.06268(12) 0.38932(12) 0.0358(3) Uani 1 1 d . . . . .
H4A H -0.3130 -0.1167 0.3909 0.043 Uiso 1 1 calc R . . . .
H4B H -0.4165 -0.0926 0.4307 0.043 Uiso 1 1 calc R . . . .
C2 C -0.42007(10) 0.06944(11) 0.25241(11) 0.0284(3) Uani 1 1 d . . . . .
C10' C 0.02137(12) 0.35108(12) 0.04441(11) 0.0351(3) Uani 1 1 d . . . . .
H10A H 0.0090 0.3017 -0.0166 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.0712 0.4101 0.0393 0.053 Uiso 1 1 calc GR . . . .
H10C H -0.0483 0.3829 0.0448 0.053 Uiso 1 1 calc GR . . . .
C4' C 0.24202(11) 0.21583(12) 0.25169(12) 0.0335(3) Uani 1 1 d . . . . .
H4'A H 0.3132 0.2512 0.2596 0.040 Uiso 1 1 calc R . . . .
H4'B H 0.2546 0.1366 0.2679 0.040 Uiso 1 1 calc R . . . .
C5 C -0.31912(11) 0.04940(11) 0.43734(11) 0.0300(3) Uani 1 1 d . . . . .
H5 H -0.2437 0.0538 0.4317 0.036 Uiso 1 1 calc R . . . .
C5' C 0.18689(11) 0.26973(11) 0.32852(11) 0.0293(3) Uani 1 1 d . . . . .
H5' H 0.1435 0.2131 0.3524 0.035 Uiso 1 1 calc R . . . .
C11' C 0.27004(12) 0.32340(14) 0.42690(12) 0.0395(3) Uani 1 1 d . . . . .
H11A H 0.3100 0.3815 0.4037 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.3215 0.2675 0.4664 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.2311 0.3550 0.4728 0.059 Uiso 1 1 calc GR . . . .
C11 C -0.31238(15) 0.06583(14) 0.55509(12) 0.0464(4) Uani 1 1 d . . . . .
H11D H -0.2839 0.1393 0.5784 0.070 Uiso 1 1 calc GR . . . .
H11E H -0.2637 0.0104 0.5989 0.070 Uiso 1 1 calc GR . . . .
H11F H -0.3853 0.0582 0.5624 0.070 Uiso 1 1 calc GR . . . .
C10 C -0.51761(13) 0.10921(17) 0.16014(13) 0.0514(4) Uani 1 1 d . . . . .
H10D H -0.5044 0.1846 0.1413 0.077 Uiso 1 1 calc GR . . . .
H10E H -0.5838 0.1072 0.1815 0.077 Uiso 1 1 calc GR . . . .
H10F H -0.5270 0.0612 0.0986 0.077 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
O1' C9' 1.3776(14) . ?
O1' C1' 1.4512(14) . ?
O1 C9 1.3746(14) . ?
O1 C2 1.4416(14) . ?
O3' C1' 1.4041(14) . ?
O3' C4' 1.4420(17) . ?
O3 C4 1.4467(18) . ?
O3 C2 1.3989(16) . ?
C8' C12 1.4039(17) . ?
C8' C9' 1.3960(17) . ?
C8' C7' 1.5108(16) . ?
C13 C9' 1.3851(16) . ?
C13 C9 1.3861(16) . ?
C12 C8 1.4026(17) . ?
C12 C14 1.5112(16) . ?
C8 C9 1.3952(17) . ?
C8 C7 1.5139(16) . ?
C6' C7' 1.5221(16) . ?
C6' C1' 1.5183(17) . ?
C6' C5' 1.5298(17) . ?
C1' C10' 1.5054(18) . ?
C6 C7 1.5238(17) . ?
C6 C2 1.5207(18) . ?
C6 C5 1.5302(18) . ?
C4 C5 1.5323(19) . ?
C2 C10 1.5037(19) . ?
C4' C5' 1.5257(19) . ?
C5 C11 1.518(2) . ?
C5' C11' 1.5201(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9' O1' C1' 118.53(9) . . ?
C9 O1 C2 120.47(9) . . ?
C1' O3' C4' 108.72(9) . . ?
C2 O3 C4 108.61(10) . . ?
C12 C8' C7' 121.75(10) . . ?
C9' C8' C12 118.52(11) . . ?
C9' C8' C7' 119.73(11) . . ?
C9' C13 C9 119.27(11) . . ?
C8' C12 C14 118.93(11) . . ?
C8 C12 C8' 121.19(11) . . ?
C8 C12 C14 119.86(11) . . ?
O1' C9' C8' 123.96(11) . . ?
O1' C9' C13 114.83(10) . . ?
C13 C9' C8' 121.19(11) . . ?
C12 C8 C7 122.77(11) . . ?
C9 C8 C12 118.04(11) . . ?
C9 C8 C7 119.19(11) . . ?
C7' C6' C5' 116.49(11) . . ?
C1' C6' C7' 114.08(10) . . ?
C1' C6' C5' 101.34(10) . . ?
O1 C9 C13 114.14(10) . . ?
O1 C9 C8 124.11(11) . . ?
C13 C9 C8 121.72(11) . . ?
C8' C7' C6' 112.14(10) . . ?
O1' C1' C6' 110.69(9) . . ?
O1' C1' C10' 108.65(10) . . ?
O3' C1' O1' 104.92(9) . . ?
O3' C1' C6' 105.19(10) . . ?
O3' C1' C10' 109.69(10) . . ?
C10' C1' C6' 117.00(11) . . ?
C7 C6 C5 115.46(10) . . ?
C2 C6 C7 114.20(11) . . ?
C2 C6 C5 101.08(10) . . ?
C8 C7 C6 110.99(10) . . ?
O3 C4 C5 107.11(11) . . ?
O1 C2 C6 110.71(10) . . ?
O1 C2 C10 107.93(11) . . ?
O3 C2 O1 105.20(10) . . ?
O3 C2 C6 105.29(11) . . ?
O3 C2 C10 109.59(12) . . ?
C10 C2 C6 117.44(12) . . ?
O3' C4' C5' 107.61(10) . . ?
C6 C5 C4 102.04(11) . . ?
C11 C5 C6 114.95(12) . . ?
C11 C5 C4 113.93(12) . . ?
C4' C5' C6' 100.83(10) . . ?
C11' C5' C6' 114.48(11) . . ?
C11' C5' C4' 112.98(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.403
