# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_xc
_audit_block_doi                 10.5517/ccdc.csd.cc24c43s
_database_code_depnum_ccdc_archive 'CCDC 1976904'
loop_
_audit_author_name
_audit_author_address
'Chao Xia'
;Henan Normal University
China
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;
_audit_creation_date             2019-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 O5'
_chemical_formula_sum            'C25 H22 O5'
_chemical_formula_weight         402.42
_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 0.0033 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           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                   6.4099(4)
_cell_length_b                   16.5738(9)
_cell_length_c                   18.3583(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.04(4)
_cell_angle_gamma                90
_cell_volume                     1950.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5254
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.8570
_cell_measurement_theta_min      2.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77562
_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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12558
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  38.00   1.00    2.00    --   11.74 -57.00 150.00   97
  2  ω    -13.00  76.00   1.00    2.00    --   11.74  77.00  60.00   89
  3  ω    -13.00  83.00   1.00    2.00    --   11.74  57.00 -60.00   96
;
_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      0.1032678000
_diffrn_orient_matrix_UB_12      -0.0051268000
_diffrn_orient_matrix_UB_13      -0.0129561000
_diffrn_orient_matrix_UB_21      0.0339646000
_diffrn_orient_matrix_UB_22      -0.0096756000
_diffrn_orient_matrix_UB_23      0.0357639000
_diffrn_orient_matrix_UB_31      -0.0206154000
_diffrn_orient_matrix_UB_32      -0.0413872000
_diffrn_orient_matrix_UB_33      -0.0067159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2951
_reflns_number_total             3439
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.049
_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)+(0.0383P)²+0.6867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0910
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C18(H18), C15(H15), C14(H14), C17(H17), C2(H2), C9(H9), C20(H20),
 C24(H24), C21(H21), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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
O5 O 0.97253(16) 0.91782(6) 0.93382(6) 0.0195(3) Uani 1 1 d . . . . .
O3 O 0.27909(15) 0.59568(6) 0.72181(6) 0.0197(3) Uani 1 1 d . . . . .
O4 O 0.72825(16) 0.71090(6) 0.65497(5) 0.0176(2) Uani 1 1 d . . . . .
O1 O 0.70441(17) 0.38293(6) 0.82806(6) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.99026(16) 0.46686(6) 0.83998(6) 0.0240(3) Uani 1 1 d . . . . .
C6 C 0.6393(2) 0.61581(9) 0.75217(8) 0.0157(3) Uani 1 1 d . . . . .
C16 C 0.9022(2) 0.86626(8) 0.87991(8) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.6263(2) 0.70258(8) 0.72469(8) 0.0155(3) Uani 1 1 d . . . . .
H12 H 0.478947 0.717061 0.719007 0.019 Uiso 1 1 calc R . . . .
C1 C 0.4674(2) 0.56480(9) 0.74665(8) 0.0170(3) Uani 1 1 d . . . . .
C13 C 0.7263(2) 0.76136(8) 0.77723(8) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.8257(2) 0.58680(9) 0.78298(8) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.943133 0.619478 0.786853 0.020 Uiso 1 1 calc R . . . .
C18 C 0.9311(2) 0.78745(9) 0.77089(8) 0.0171(3) Uani 1 1 d . . . . .
H18 H 1.011347 0.769339 0.731987 0.021 Uiso 1 1 calc R . . . .
C15 C 0.6982(2) 0.83957(9) 0.88783(8) 0.0176(3) Uani 1 1 d . . . . .
H15 H 0.619369 0.856437 0.927534 0.021 Uiso 1 1 calc R . . . .
C4 C 0.8276(2) 0.50852(9) 0.80708(8) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.6118(2) 0.78791(9) 0.83684(8) 0.0169(3) Uani 1 1 d . . . . .
H14 H 0.474679 0.770691 0.842584 0.020 Uiso 1 1 calc R . . . .
C11 C 0.6320(2) 0.66484(9) 0.59762(8) 0.0182(3) Uani 1 1 d . . . . .
H11A H 0.622853 0.608927 0.612912 0.022 Uiso 1 1 calc R . . . .
H11B H 0.720960 0.666880 0.554911 0.022 Uiso 1 1 calc R . . . .
C17 C 1.0198(2) 0.84024(9) 0.82147(8) 0.0176(3) Uani 1 1 d . . . . .
H17 H 1.156803 0.857676 0.815824 0.021 Uiso 1 1 calc R . . . .
C19 C 0.4016(2) 0.76574(9) 0.52818(8) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.6567(2) 0.45835(9) 0.80023(8) 0.0190(3) Uani 1 1 d . . . . .
C10 C 0.4161(2) 0.69384(9) 0.57671(8) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.4731(2) 0.48379(9) 0.76950(8) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.359138 0.449555 0.764103 0.024 Uiso 1 1 calc R . . . .
C9 C 0.2438(2) 0.65688(9) 0.60094(8) 0.0208(4) Uani 1 1 d . . . . .
H9 H 0.117274 0.680813 0.588744 0.025 Uiso 1 1 calc R . . . .
C8 C 0.2320(3) 0.58107(9) 0.64564(9) 0.0226(4) Uani 1 1 d . . . . .
H8A H 0.092888 0.558422 0.641651 0.027 Uiso 1 1 calc R . . . .
H8B H 0.329784 0.541847 0.626371 0.027 Uiso 1 1 calc R . . . .
C25 C 1.1815(2) 0.94581(9) 0.92789(9) 0.0222(4) Uani 1 1 d . . . . .
H25A H 1.200416 0.971784 0.881623 0.033 Uiso 1 1 calc GR . . . .
H25B H 1.275540 0.900951 0.931771 0.033 Uiso 1 1 calc GR . . . .
H25C H 1.209523 0.983615 0.966286 0.033 Uiso 1 1 calc GR . . . .
C20 C 0.2281(3) 0.77703(10) 0.48238(9) 0.0250(4) Uani 1 1 d . . . . .
H20 H 0.121766 0.738863 0.482200 0.030 Uiso 1 1 calc R . . . .
C7 C 0.8885(3) 0.39781(10) 0.87109(9) 0.0271(4) Uani 1 1 d . . . . .
H7A H 0.850720 0.408403 0.921352 0.033 Uiso 1 1 calc R . . . .
H7B H 0.980398 0.351323 0.869805 0.033 Uiso 1 1 calc R . . . .
C24 C 0.5598(3) 0.82327(10) 0.52568(9) 0.0255(4) Uani 1 1 d . . . . .
H24 H 0.677289 0.817000 0.554836 0.031 Uiso 1 1 calc R . . . .
C21 C 0.2128(3) 0.84419(11) 0.43740(9) 0.0339(5) Uani 1 1 d . . . . .
H21 H 0.096246 0.850890 0.407855 0.041 Uiso 1 1 calc R . . . .
C23 C 0.5440(3) 0.88998(11) 0.48010(10) 0.0345(4) Uani 1 1 d . . . . .
H23 H 0.651445 0.927658 0.478918 0.041 Uiso 1 1 calc R . . . .
C22 C 0.3702(3) 0.90098(11) 0.43649(9) 0.0375(5) Uani 1 1 d . . . . .
H22 H 0.359624 0.946265 0.406801 0.045 Uiso 1 1 calc R . . . .


_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
O5 C16 1.3831(17) . ?
O5 C25 1.4215(18) . ?
O3 C1 1.3883(18) . ?
O3 C8 1.4510(18) . ?
O4 C12 1.4437(18) . ?
O4 C11 1.4393(17) . ?
O1 C3 1.3846(18) . ?
O1 C7 1.441(2) . ?
O2 C4 1.3886(18) . ?
O2 C7 1.4356(19) . ?
C6 C12 1.526(2) . ?
C6 C1 1.392(2) . ?
C6 C5 1.407(2) . ?
C16 C15 1.388(2) . ?
C16 C17 1.381(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.513(2) . ?
C1 C2 1.407(2) . ?
C13 C18 1.387(2) . ?
C13 C14 1.389(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.371(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.397(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(2) . ?
C4 C3 1.381(2) . ?
C14 H14 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.515(2) . ?
C17 H17 0.9300 . ?
C19 C10 1.491(2) . ?
C19 C20 1.407(2) . ?
C19 C24 1.392(2) . ?
C3 C2 1.372(2) . ?
C10 C9 1.339(2) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.503(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.389(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C24 H24 0.9300 . ?
C24 C23 1.390(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.384(3) . ?
C22 H22 0.9300 . ?

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
C16 O5 C25 117.00(12) . . ?
C1 O3 C8 115.85(11) . . ?
C11 O4 C12 113.82(11) . . ?
C3 O1 C7 103.20(12) . . ?
C4 O2 C7 103.21(12) . . ?
C1 C6 C12 120.34(13) . . ?
C1 C6 C5 119.58(13) . . ?
C5 C6 C12 120.08(13) . . ?
O5 C16 C15 115.41(13) . . ?
C17 C16 O5 124.82(13) . . ?
C17 C16 C15 119.77(14) . . ?
O4 C12 C6 110.99(11) . . ?
O4 C12 H12 108.6 . . ?
O4 C12 C13 108.16(11) . . ?
C6 C12 H12 108.6 . . ?
C13 C12 C6 111.89(12) . . ?
C13 C12 H12 108.6 . . ?
O3 C1 C6 119.21(13) . . ?
O3 C1 C2 118.16(13) . . ?
C6 C1 C2 122.52(14) . . ?
C18 C13 C12 123.24(13) . . ?
C18 C13 C14 117.87(14) . . ?
C14 C13 C12 118.82(13) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 C6 117.44(14) . . ?
C4 C5 H5 121.3 . . ?
C13 C18 H18 119.2 . . ?
C13 C18 C17 121.67(14) . . ?
C17 C18 H18 119.2 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.23(14) . . ?
C14 C15 H15 119.9 . . ?
C5 C4 O2 128.15(14) . . ?
C5 C4 C3 122.23(14) . . ?
C3 C4 O2 109.61(13) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.14(14) . . ?
C15 C14 H14 119.4 . . ?
O4 C11 H11A 108.7 . . ?
O4 C11 H11B 108.7 . . ?
O4 C11 C10 114.12(12) . . ?
H11A C11 H11B 107.6 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C16 C17 C18 119.32(14) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C20 C19 C10 120.84(15) . . ?
C24 C19 C10 121.45(14) . . ?
C24 C19 C20 117.70(15) . . ?
C4 C3 O1 109.57(13) . . ?
C2 C3 O1 128.21(14) . . ?
C2 C3 C4 122.22(14) . . ?
C19 C10 C11 117.51(13) . . ?
C9 C10 C11 121.63(14) . . ?
C9 C10 C19 120.86(14) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 C1 115.96(14) . . ?
C3 C2 H2 122.0 . . ?
C10 C9 H9 116.4 . . ?
C10 C9 C8 127.27(14) . . ?
C8 C9 H9 116.4 . . ?
O3 C8 C9 112.10(12) . . ?
O3 C8 H8A 109.2 . . ?
O3 C8 H8B 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.17(17) . . ?
C21 C20 H20 119.4 . . ?
O1 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
O2 C7 O1 106.87(12) . . ?
O2 C7 H7A 110.3 . . ?
O2 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.76(16) . . ?
C23 C24 H24 119.6 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.14(17) . . ?
C22 C21 H21 119.9 . . ?
C24 C23 H23 119.6 . . ?
C22 C23 C24 120.77(18) . . ?
C22 C23 H23 119.6 . . ?
C21 C22 C23 119.45(17) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.576
####################################################################### 
# 
# 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_xc-20181015
_database_code_depnum_ccdc_archive 'CCDC 1976905'
loop_
_audit_author_name
_audit_author_address
'Chao Xia'
;Henan Normal University
China
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 O5'
_chemical_formula_weight         400.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   14.7117(2)
_cell_length_b                   10.94480(10)
_cell_length_c                   13.1133(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.597(2)
_cell_angle_gamma                90
_cell_volume                     1949.36(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.776
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10459
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.190
_diffrn_reflns_theta_max         71.199
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3702
_reflns_number_gt                3357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.0269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3702
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.31597(8) 0.35725(10) 0.40063(8) 0.0221(2) Uani 1 1 d . . . . .
O14 O 0.37833(8) 0.17717(10) 0.49768(9) 0.0232(2) Uani 1 1 d . . . . .
O21 O 0.64439(9) 0.24953(11) 0.22449(11) 0.0319(3) Uani 1 1 d . . . . .
O6 O 0.19720(9) 0.74469(10) 0.47289(10) 0.0290(3) Uani 1 1 d . . . . .
O8 O 0.12586(10) 0.65905(11) 0.58622(10) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.26829(11) 0.42553(14) 0.45451(12) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.22592(11) 0.37111(14) 0.52207(12) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.21244(11) 0.62042(14) 0.48043(12) 0.0216(3) Uani 1 1 d . . . . .
C23 C 0.15641(11) 0.16989(13) 0.43207(12) 0.0190(3) Uani 1 1 d . . . . .
C9 C 0.17030(11) 0.56930(15) 0.54750(12) 0.0228(3) Uani 1 1 d . . . . .
C4 C 0.26208(11) 0.55092(14) 0.43142(12) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.2900 0.5852 0.3854 0.026 Uiso 1 1 calc R U . . .
C12 C 0.22732(11) 0.23166(14) 0.53753(12) 0.0198(3) Uani 1 1 d . . . . .
C15 C 0.46712(11) 0.27986(14) 0.40540(12) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.17528(11) 0.44626(15) 0.56964(12) 0.0227(3) Uani 1 1 d . . . . .
H10 H 0.1459 0.4135 0.6149 0.027 Uiso 1 1 calc R U . . .
C20 C 0.49687(11) 0.38460(14) 0.36733(13) 0.0242(3) Uani 1 1 d . . . . .
H20 H 0.4760 0.4603 0.3822 0.029 Uiso 1 1 calc R U . . .
C18 C 0.58722(11) 0.26633(15) 0.28457(13) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.40162(11) 0.29245(14) 0.46990(12) 0.0214(3) Uani 1 1 d . . . . .
H1 H 0.4359 0.3397 0.5373 0.026 Uiso 1 1 calc R U . . .
C13 C 0.33353(11) 0.18005(15) 0.57680(12) 0.0234(3) Uani 1 1 d . . . . .
H13A H 0.3751 0.2283 0.6394 0.028 Uiso 1 1 calc R U . . .
H13B H 0.3328 0.0974 0.6031 0.028 Uiso 1 1 calc R U . . .
C24 C 0.17550(11) 0.05605(15) 0.39795(13) 0.0243(3) Uani 1 1 d . . . . .
H24 H 0.2351 0.0175 0.4372 0.029 Uiso 1 1 calc R U . . .
C26 C 0.01724(12) 0.05424(15) 0.24681(13) 0.0267(3) Uani 1 1 d . . . . .
H26 H -0.0286 0.0162 0.1850 0.032 Uiso 1 1 calc R U . . .
C28 C 0.06579(12) 0.22431(14) 0.37235(13) 0.0245(3) Uani 1 1 d . . . . .
H28 H 0.0513 0.3002 0.3942 0.029 Uiso 1 1 calc R U . . .
C25 C 0.10658(12) -0.00121(15) 0.30585(14) 0.0267(3) Uani 1 1 d . . . . .
H25 H 0.1207 -0.0773 0.2839 0.032 Uiso 1 1 calc R U . . .
C19 C 0.55681(11) 0.37958(15) 0.30774(13) 0.0246(3) Uani 1 1 d . . . . .
H19 H 0.5764 0.4510 0.2836 0.029 Uiso 1 1 calc R U . . .
C29 C 0.19913(12) 0.20012(15) 0.63509(13) 0.0252(3) Uani 1 1 d . . . . .
H29 H 0.2338 0.2400 0.7014 0.030 Uiso 1 1 calc R U . . .
C16 C 0.49954(12) 0.16731(15) 0.38328(14) 0.0260(3) Uani 1 1 d . . . . .
H16 H 0.4812 0.0960 0.4090 0.031 Uiso 1 1 calc R U . . .
C17 C 0.55892(12) 0.16082(15) 0.32321(14) 0.0276(4) Uani 1 1 d . . . . .
H17 H 0.5800 0.0851 0.3086 0.033 Uiso 1 1 calc R U . . .
C27 C -0.00317(12) 0.16705(16) 0.28086(14) 0.0296(4) Uani 1 1 d . . . . .
H27 H -0.0634 0.2046 0.2423 0.035 Uiso 1 1 calc R U . . .
C30 C 0.13039(13) 0.12189(17) 0.63503(15) 0.0323(4) Uani 1 1 d . . . . .
C22 C 0.66254(13) 0.35436(16) 0.17058(15) 0.0305(4) Uani 1 1 d . . . . .
H22A H 0.6010 0.3896 0.1233 0.046 Uiso 1 1 calc R U . . .
H22B H 0.6994 0.3308 0.1272 0.046 Uiso 1 1 calc R U . . .
H22C H 0.6995 0.4133 0.2249 0.046 Uiso 1 1 calc R U . . .
C7 C 0.13820(15) 0.76969(16) 0.53564(16) 0.0349(4) Uani 1 1 d . . . . .
H7A H 0.1703 0.8305 0.5918 0.042 Uiso 1 1 calc R U . . .
H7B H 0.0745 0.8013 0.4876 0.042 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 C3 1.3895(18) . ?
O2 C1 1.4269(18) . ?
O14 C1 1.3922(19) . ?
O14 C13 1.4275(18) . ?
O21 C18 1.3679(19) . ?
O21 C22 1.426(2) . ?
O6 C5 1.3758(19) . ?
O6 C7 1.433(2) . ?
O8 C9 1.3803(19) . ?
O8 C7 1.425(2) . ?
C3 C11 1.397(2) . ?
C3 C4 1.401(2) . ?
C11 C10 1.406(2) . ?
C11 C12 1.539(2) . ?
C5 C4 1.373(2) . ?
C5 C9 1.375(2) . ?
C23 C24 1.388(2) . ?
C23 C28 1.394(2) . ?
C23 C12 1.533(2) . ?
C9 C10 1.374(2) . ?
C4 H4 0.9300 . ?
C12 C29 1.528(2) . ?
C12 C13 1.552(2) . ?
C15 C20 1.387(2) . ?
C15 C16 1.391(2) . ?
C15 C1 1.513(2) . ?
C10 H10 0.9300 . ?
C20 C19 1.386(2) . ?
C20 H20 0.9300 . ?
C18 C17 1.388(2) . ?
C18 C19 1.390(2) . ?
C1 H1 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C24 C25 1.392(2) . ?
C24 H24 0.9300 . ?
C26 C25 1.383(2) . ?
C26 C27 1.385(2) . ?
C26 H26 0.9300 . ?
C28 C27 1.388(2) . ?
C28 H28 0.9300 . ?
C25 H25 0.9300 . ?
C19 H19 0.9300 . ?
C29 C30 1.325(2) . ?
C29 H29 0.9300 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C27 H27 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C1 116.01(11) . . ?
C1 O14 C13 113.51(12) . . ?
C18 O21 C22 116.82(13) . . ?
C5 O6 C7 105.39(12) . . ?
C9 O8 C7 105.69(12) . . ?
O2 C3 C11 121.90(14) . . ?
O2 C3 C4 114.88(13) . . ?
C11 C3 C4 123.15(14) . . ?
C3 C11 C10 118.25(14) . . ?
C3 C11 C12 121.31(13) . . ?
C10 C11 C12 120.27(13) . . ?
C4 C5 C9 121.71(15) . . ?
C4 C5 O6 127.97(14) . . ?
C9 C5 O6 110.32(14) . . ?
C24 C23 C28 118.08(14) . . ?
C24 C23 C12 122.33(13) . . ?
C28 C23 C12 119.39(13) . . ?
C10 C9 C5 122.25(14) . . ?
C10 C9 O8 127.91(14) . . ?
C5 C9 O8 109.84(14) . . ?
C5 C4 C3 116.35(14) . . ?
C5 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
C29 C12 C23 110.25(12) . . ?
C29 C12 C11 109.89(12) . . ?
C23 C12 C11 110.40(12) . . ?
C29 C12 C13 101.68(12) . . ?
C23 C12 C13 112.85(12) . . ?
C11 C12 C13 111.44(12) . . ?
C20 C15 C16 118.43(14) . . ?
C20 C15 C1 118.87(14) . . ?
C16 C15 C1 122.70(14) . . ?
C9 C10 C11 118.29(14) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C19 C20 C15 121.84(14) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
O21 C18 C17 115.83(14) . . ?
O21 C18 C19 124.50(15) . . ?
C17 C18 C19 119.67(15) . . ?
O14 C1 O2 111.79(12) . . ?
O14 C1 C15 109.71(13) . . ?
O2 C1 C15 106.60(12) . . ?
O14 C1 H1 109.6 . . ?
O2 C1 H1 109.6 . . ?
C15 C1 H1 109.6 . . ?
O14 C13 C12 117.01(12) . . ?
O14 C13 H13A 108.0 . . ?
C12 C13 H13A 108.0 . . ?
O14 C13 H13B 108.0 . . ?
C12 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C23 C24 C25 120.89(14) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C25 C26 C27 119.20(15) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C27 C28 C23 121.08(15) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C26 C25 C24 120.45(15) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C20 C19 C18 119.11(15) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C30 C29 C12 126.73(15) . . ?
C30 C29 H29 116.6 . . ?
C12 C29 H29 116.6 . . ?
C17 C16 C15 120.38(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.57(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C26 C27 C28 120.30(15) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8 C7 O6 108.57(13) . . ?
O8 C7 H7A 110.0 . . ?
O6 C7 H7A 110.0 . . ?
O8 C7 H7B 110.0 . . ?
O6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C3 C11 -62.93(18) . . . . ?
C1 O2 C3 C4 120.05(14) . . . . ?
O2 C3 C11 C10 -177.24(13) . . . . ?
C4 C3 C11 C10 -0.5(2) . . . . ?
O2 C3 C11 C12 -1.8(2) . . . . ?
C4 C3 C11 C12 174.94(14) . . . . ?
C7 O6 C5 C4 177.74(16) . . . . ?
C7 O6 C5 C9 -2.65(17) . . . . ?
C4 C5 C9 C10 0.1(2) . . . . ?
O6 C5 C9 C10 -179.57(14) . . . . ?
C4 C5 C9 O8 179.65(14) . . . . ?
O6 C5 C9 O8 0.01(17) . . . . ?
C7 O8 C9 C10 -177.79(17) . . . . ?
C7 O8 C9 C5 2.66(18) . . . . ?
C9 C5 C4 C3 -0.7(2) . . . . ?
O6 C5 C4 C3 178.89(14) . . . . ?
O2 C3 C4 C5 177.86(12) . . . . ?
C11 C3 C4 C5 0.9(2) . . . . ?
C24 C23 C12 C29 -92.56(17) . . . . ?
C28 C23 C12 C29 82.15(17) . . . . ?
C24 C23 C12 C11 145.83(14) . . . . ?
C28 C23 C12 C11 -39.46(18) . . . . ?
C24 C23 C12 C13 20.37(19) . . . . ?
C28 C23 C12 C13 -164.91(13) . . . . ?
C3 C11 C12 C29 166.40(13) . . . . ?
C10 C11 C12 C29 -18.28(19) . . . . ?
C3 C11 C12 C23 -71.77(17) . . . . ?
C10 C11 C12 C23 103.55(15) . . . . ?
C3 C11 C12 C13 54.47(18) . . . . ?
C10 C11 C12 C13 -130.21(14) . . . . ?
C5 C9 C10 C11 0.4(2) . . . . ?
O8 C9 C10 C11 -179.12(14) . . . . ?
C3 C11 C10 C9 -0.2(2) . . . . ?
C12 C11 C10 C9 -175.64(13) . . . . ?
C16 C15 C20 C19 0.5(2) . . . . ?
C1 C15 C20 C19 -179.99(14) . . . . ?
C22 O21 C18 C17 171.20(15) . . . . ?
C22 O21 C18 C19 -8.6(2) . . . . ?
C13 O14 C1 O2 -73.78(15) . . . . ?
C13 O14 C1 C15 168.18(11) . . . . ?
C3 O2 C1 O14 87.85(15) . . . . ?
C3 O2 C1 C15 -152.27(12) . . . . ?
C20 C15 C1 O14 178.44(13) . . . . ?
C16 C15 C1 O14 -2.1(2) . . . . ?
C20 C15 C1 O2 57.23(17) . . . . ?
C16 C15 C1 O2 -123.29(15) . . . . ?
C1 O14 C13 C12 69.93(17) . . . . ?
C29 C12 C13 O14 170.76(13) . . . . ?
C23 C12 C13 O14 52.68(18) . . . . ?
C11 C12 C13 O14 -72.21(17) . . . . ?
C28 C23 C24 C25 0.9(2) . . . . ?
C12 C23 C24 C25 175.63(14) . . . . ?
C24 C23 C28 C27 -0.5(2) . . . . ?
C12 C23 C28 C27 -175.46(14) . . . . ?
C27 C26 C25 C24 -0.5(2) . . . . ?
C23 C24 C25 C26 -0.4(2) . . . . ?
C15 C20 C19 C18 0.6(2) . . . . ?
O21 C18 C19 C20 178.43(14) . . . . ?
C17 C18 C19 C20 -1.3(2) . . . . ?
C23 C12 C29 C30 6.3(2) . . . . ?
C11 C12 C29 C30 128.19(18) . . . . ?
C13 C12 C29 C30 -113.66(18) . . . . ?
C20 C15 C16 C17 -0.9(2) . . . . ?
C1 C15 C16 C17 179.58(14) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
O21 C18 C17 C16 -178.86(15) . . . . ?
C19 C18 C17 C16 0.9(2) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C23 C28 C27 C26 -0.3(3) . . . . ?
C9 O8 C7 O6 -4.27(19) . . . . ?
C5 O6 C7 O8 4.27(19) . . . . ?

_refine_diff_density_max         0.757
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052



