# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_2(H)
_database_code_depnum_ccdc_archive 'CCDC 2059406'
loop_
_audit_author_name
_audit_author_address
'Yu Hai'
;State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matte
China
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C22 H23 N O2'
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.43
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.185(4)
_cell_length_b                   6.459(2)
_cell_length_c                   23.661(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.458(5)
_cell_angle_gamma                90
_cell_volume                     1850.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.1500
_cell_measurement_reflns_used    4630
_cell_measurement_theta_min      2.5471
_cell_measurement_theta_max      27.5398
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_description       Prism
_exptl_crystal_density_diffrn    1.1968
_exptl_crystal_F_000             712.3227
_diffrn_ambient_temperature      293.1500
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14107
_diffrn_reflns_theta_full        27.4632
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.93
_diffrn_measured_fraction_theta_full 0.9922
_diffrn_measured_fraction_theta_max 0.9922
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -15
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              -12
_reflns_number_gt                3201
_reflns_number_total             4197
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.2114
_refine_diff_density_min         -0.2066
_refine_diff_density_rms         0.0440
_refine_ls_d_res_high            0.7706
_refine_ls_d_res_low             6.9451
_refine_ls_goodness_of_fit_ref   1.0506
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.0506
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.1206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1350
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C11(H11a,H11b), C9(H9a,H9b), C8(H8a,H8b), C5(H5a,H5b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C10(H10), C7(H7), C6(H6), C4(H4), C3(H3),
 C2(H2), C1(H1a)
;
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_refinement_flags_posn
O2 O 0.25343(7) 0.71017(15) 0.20655(4) 0.0470(3) Uani 1.000000 .
O1 O 0.31663(8) 0.69235(15) 0.29894(4) 0.0501(3) Uani 1.000000 .
C22 C 0.23910(11) 0.7006(2) 0.26221(5) 0.0412(3) Uani 1.000000 .
C21 C 0.07670(10) 0.7058(2) 0.32443(5) 0.0445(3) Uani 1.000000 .
N1 N 0.12516(10) 0.5823(2) 0.12891(4) 0.0466(3) Uani 1.000000 .
C20 C 0.18332(11) 0.6111(2) 0.07830(5) 0.0454(3) Uani 1.000000 .
H20 H 0.25918(11) 0.6556(2) 0.09051(5) 0.0545(4) Uiso 1.000000 R
C19 C 0.11943(11) 0.7063(2) 0.26825(5) 0.0417(3) Uani 1.000000 .
C18 C 0.06454(11) 0.7255(2) 0.21636(5) 0.0429(3) Uani 1.000000 .
C17 C -0.05565(11) 0.7437(2) 0.20028(5) 0.0470(3) Uani 1.000000 .
C16 C 0.14382(11) 0.7321(2) 0.17206(5) 0.0433(3) Uani 1.000000 .
H16 H 0.13982(11) 0.8695(2) 0.15441(5) 0.0520(4) Uiso 1.000000 R
C15 C 0.12626(15) 0.7769(3) 0.04020(6) 0.0607(4) Uani 1.000000 .
H15a H 0.04875(15) 0.7418(3) 0.03175(6) 0.0728(5) Uiso 1.000000 R
H15b H 0.13092(15) 0.9081(3) 0.06027(6) 0.0728(5) Uiso 1.000000 R
C14 C -0.09932(14) 0.9069(3) 0.16750(7) 0.0677(5) Uani 1.000000 .
H14 H -0.05263(14) 1.0065(3) 0.15490(7) 0.0813(6) Uiso 1.000000 R
C13 C 0.08732(13) 0.5337(3) 0.35898(6) 0.0608(4) Uani 1.000000 .
H13 H 0.12296(13) 0.4166(3) 0.34724(6) 0.0730(5) Uiso 1.000000 R
C12 C 0.02457(14) 0.8793(3) 0.34309(7) 0.0657(4) Uani 1.000000 .
H12 H 0.01744(14) 0.9974(3) 0.32049(7) 0.0788(5) Uiso 1.000000 R
C11 C 0.18679(15) 0.4086(3) 0.04673(6) 0.0606(4) Uani 1.000000 .
H11a H 0.22909(15) 0.3085(3) 0.07076(6) 0.0727(5) Uiso 1.000000 R
H11b H 0.11227(15) 0.3555(3) 0.03834(6) 0.0727(5) Uiso 1.000000 R
C10 C -0.00645(14) 0.7061(3) 0.42889(7) 0.0749(5) Uani 1.000000 .
H10 H -0.03441(14) 0.7062(3) 0.46388(7) 0.0899(6) Uiso 1.000000 R
C9 C 0.23874(18) 0.4335(3) -0.00882(7) 0.0780(5) Uani 1.000000 .
H9a H 0.31577(18) 0.4719(3) -0.00019(7) 0.0936(7) Uiso 1.000000 R
H9b H 0.23579(18) 0.3021(3) -0.02879(7) 0.0936(7) Uiso 1.000000 R
C8 C 0.18013(17) 0.5959(3) -0.04673(6) 0.0767(5) Uani 1.000000 .
H8a H 0.21795(17) 0.6140(3) -0.08034(6) 0.0920(6) Uiso 1.000000 R
H8b H 0.10526(17) 0.5508(3) -0.05889(6) 0.0920(6) Uiso 1.000000 R
C7 C -0.28175(14) 0.7751(3) 0.17055(7) 0.0715(5) Uani 1.000000 .
H7 H -0.35758(14) 0.7863(3) 0.16072(7) 0.0858(6) Uiso 1.000000 R
C6 C -0.12700(13) 0.5955(3) 0.21724(7) 0.0632(4) Uani 1.000000 .
H6 H -0.09892(13) 0.4838(3) 0.23906(7) 0.0758(5) Uiso 1.000000 R
C5 C 0.17736(17) 0.8005(3) -0.01543(7) 0.0753(5) Uani 1.000000 .
H5a H 0.13485(17) 0.9001(3) -0.03953(7) 0.0904(6) Uiso 1.000000 R
H5b H 0.25198(17) 0.8534(3) -0.00740(7) 0.0904(6) Uiso 1.000000 R
C4 C 0.04547(15) 0.5333(3) 0.41107(7) 0.0738(5) Uani 1.000000 .
H4 H 0.05256(15) 0.4159(3) 0.43394(7) 0.0886(6) Uiso 1.000000 R
C3 C -0.21230(15) 0.9230(3) 0.15327(7) 0.0778(6) Uani 1.000000 .
H3 H -0.24123(15) 1.0350(3) 0.13184(7) 0.0934(7) Uiso 1.000000 R
C2 C -0.01696(16) 0.8780(3) 0.39512(7) 0.0795(6) Uani 1.000000 .
H2 H -0.05227(16) 0.9950(3) 0.40720(7) 0.0954(7) Uiso 1.000000 R
C1 C -0.23953(14) 0.6116(3) 0.20214(8) 0.0760(5) Uani 1.000000 .
H1a H -0.28659(14) 0.5103(3) 0.21359(8) 0.0912(6) Uiso 1.000000 R
H1 H 0.1332(12) 0.455(3) 0.1441(7) 0.059(5) Uiso 1.000000 .


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 C22 1.3492(15) . ?
O2 C16 1.4915(16) . ?
O1 C22 1.2109(15) . ?
C22 C19 1.4815(19) . ?
C21 C19 1.4811(18) . ?
C21 C13 1.377(2) . ?
C21 C12 1.385(2) . ?
N1 C20 1.4702(17) . ?
N1 C16 1.4063(17) . ?
C20 C15 1.517(2) . ?
C20 C11 1.509(2) . ?
C19 C18 1.3362(17) . ?
C18 C17 1.4759(19) . ?
C18 C16 1.5038(18) . ?
C17 C14 1.379(2) . ?
C17 C6 1.382(2) . ?
C15 C5 1.526(2) . ?
C14 C3 1.384(2) . ?
C13 C4 1.386(2) . ?
C12 C2 1.383(2) . ?
C11 C9 1.530(2) . ?
C10 C4 1.373(3) . ?
C10 C2 1.365(3) . ?
C9 C8 1.507(3) . ?
C8 C5 1.517(3) . ?
C7 C3 1.369(3) . ?
C7 C1 1.361(3) . ?
C6 C1 1.381(2) . ?

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 O2 C22 109.40(10) . . ?
O1 C22 O2 121.77(12) . . ?
C19 C22 O2 109.26(11) . . ?
C19 C22 O1 128.96(12) . . ?
C13 C21 C19 121.02(13) . . ?
C12 C21 C19 120.32(13) . . ?
C12 C21 C13 118.66(13) . . ?
C16 N1 C20 116.80(11) . . ?
C15 C20 N1 110.04(12) . . ?
C11 C20 N1 109.66(11) . . ?
C11 C20 C15 110.73(11) . . ?
C21 C19 C22 122.40(11) . . ?
C18 C19 C22 108.06(11) . . ?
C18 C19 C21 129.39(12) . . ?
C17 C18 C19 128.60(12) . . ?
C16 C18 C19 110.41(11) . . ?
C16 C18 C17 120.97(10) . . ?
C14 C17 C18 120.98(13) . . ?
C6 C17 C18 120.55(13) . . ?
C6 C17 C14 118.47(14) . . ?
N1 C16 O2 113.18(11) . . ?
C18 C16 O2 102.82(9) . . ?
C18 C16 N1 114.99(11) . . ?
C5 C15 C20 112.27(14) . . ?
C3 C14 C17 120.30(16) . . ?
C4 C13 C21 120.68(16) . . ?
C2 C12 C21 120.41(16) . . ?
C9 C11 C20 111.80(14) . . ?
C2 C10 C4 119.85(15) . . ?
C8 C9 C11 111.73(15) . . ?
C5 C8 C9 110.54(13) . . ?
C1 C7 C3 119.83(15) . . ?
C1 C6 C17 120.76(16) . . ?
C8 C5 C15 111.58(14) . . ?
C10 C4 C13 119.99(16) . . ?
C7 C3 C14 120.43(16) . . ?
C10 C2 C12 120.40(17) . . ?
C6 C1 C7 120.20(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3(OMe)
_database_code_depnum_ccdc_archive 'CCDC 2059405'
loop_
_audit_author_name
_audit_author_address
'Yu Hai'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C18 H13 O5'
_chemical_formula_sum            'C18 H13 O5'
_chemical_formula_weight         309.30
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   3.973(4)
_cell_length_b                   20.429(17)
_cell_length_c                   17.719(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.915(15)
_cell_angle_gamma                90
_cell_volume                     1433(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.1500
_cell_measurement_reflns_used    3912
_cell_measurement_theta_min      3.6032
_cell_measurement_theta_max      27.4584
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_description       Prism
_exptl_crystal_density_diffrn    1.4335
_exptl_crystal_F_000             644.4092
_diffrn_ambient_temperature      293.1500
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11830
_diffrn_reflns_theta_full        24.9998
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.60
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1970
_reflns_number_total             2505
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.4661
_refine_diff_density_min         -0.4201
_refine_diff_density_rms         0.1103
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.6547
_refine_ls_goodness_of_fit_ref   1.0426
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.1310
_refine_ls_restrained_S_all      1.0349
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+4.5617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2595
_refine_ls_wR_factor_ref         0.2807
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-O4A
 1.24 with sigma of 0.02
 C16-O4B
 1.24 with sigma of 0.02
 O5A-C16
 1.45 with sigma of 0.02
 C15-O5B
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O4B) \\sim Ueq, Uanis(O5A)
\\sim Ueq, Uanis(O5B) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(O4B)=Sof(O5B)=Sof(H5B)=1-FVAR(1)
 Sof(O4A)=Sof(O5A)=Sof(H5A)=FVAR(1)
5.a Riding coordinates:
 O5A(H5A), O5B(H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12)
5.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
O1 O 0.1193(12) 0.90099(19) 0.8027(2) 0.0700(13) Uani 1.000000 . . .
O2 O -0.0030(13) 0.5570(2) 0.9200(2) 0.0768(14) Uani 1.000000 . . .
O3 O 0.6656(12) 0.6294(2) 0.5250(2) 0.0784(14) Uani 1.000000 . U .
C1 C 0.1816(14) 0.7835(3) 0.7850(3) 0.0498(14) Uani 1.000000 . . .
H1 H 0.1027(14) 0.7744(3) 0.8318(3) 0.0597(17) Uiso 1.000000 R . .
C2 C 0.2050(15) 0.8471(3) 0.7622(3) 0.0557(15) Uani 1.000000 . . .
C3 C 0.3308(16) 0.8620(3) 0.6922(4) 0.0638(17) Uani 1.000000 . . .
H3 H 0.3492(16) 0.9053(3) 0.6771(4) 0.077(2) Uiso 1.000000 R . .
C4 C 0.4257(16) 0.8125(3) 0.6467(3) 0.0606(16) Uani 1.000000 . . .
H4 H 0.5103(16) 0.8225(3) 0.6007(3) 0.0727(19) Uiso 1.000000 R . .
C5 C 0.3972(14) 0.7466(3) 0.6684(3) 0.0522(14) Uani 1.000000 . . .
C6 C 0.4882(14) 0.6926(3) 0.6222(3) 0.0533(15) Uani 1.000000 . . .
C7 C 0.4591(14) 0.6298(3) 0.6438(3) 0.0530(15) Uani 1.000000 . . .
C8 C 0.3406(14) 0.6112(3) 0.7140(3) 0.0507(14) Uani 1.000000 . . .
C9 C 0.3147(16) 0.5456(3) 0.7368(3) 0.0612(16) Uani 1.000000 . . .
H9 H 0.3780(16) 0.5122(3) 0.7052(3) 0.073(2) Uiso 1.000000 R . .
C10 C 0.1966(17) 0.5302(3) 0.8055(4) 0.0705(18) Uani 1.000000 . . .
H10 H 0.1785(17) 0.4866(3) 0.8196(4) 0.085(2) Uiso 1.000000 R . .
C11 C 0.1039(16) 0.5796(3) 0.8538(3) 0.0601(16) Uani 1.000000 . . .
C12 C 0.1254(14) 0.6443(3) 0.8326(3) 0.0516(14) Uani 1.000000 . . .
H12 H 0.0602(14) 0.6769(3) 0.8650(3) 0.0619(17) Uiso 1.000000 R . .
C13 C 0.2446(13) 0.6622(3) 0.7624(3) 0.0462(13) Uani 1.000000 . . .
C14 C 0.2756(13) 0.7311(3) 0.7387(3) 0.0496(14) Uani 1.000000 . . .
C15 C 0.6263(18) 0.6947(4) 0.5464(4) 0.074(2) Uani 1.000000 D . .
C16 C 0.5733(19) 0.5861(4) 0.5826(4) 0.081(2) Uani 1.000000 D . .
C17 C -0.0064(17) 0.8896(3) 0.8751(3) 0.0643(17) Uani 1.000000 . . .
H17a H -0.201(7) 0.8617(17) 0.8689(4) 0.097(3) Uiso 1.000000 GR . .
H17b H 0.166(4) 0.8690(19) 0.9082(8) 0.097(3) Uiso 1.000000 GR . .
H17c H -0.068(10) 0.9306(4) 0.8965(12) 0.097(3) Uiso 1.000000 GR . .
C18 C -0.105(2) 0.6041(3) 0.9729(4) 0.081(2) Uani 1.000000 . . .
H18a H 0.086(3) 0.6302(17) 0.991(2) 0.121(3) Uiso 1.000000 GR . .
H18b H -0.276(9) 0.6319(17) 0.9485(9) 0.121(3) Uiso 1.000000 GR . .
H18c H -0.193(12) 0.5820(4) 1.0147(15) 0.121(3) Uiso 1.000000 GR . .
O4A O 0.729(3) 0.7347(4) 0.5110(5) 0.086(4) Uani 0.610(14) D U 1
O5A O 0.352(2) 0.5392(4) 0.5556(4) 0.060(3) Uani 0.610(14) D U 1
H5A H 0.145(2) 0.5528(4) 0.5612(4) 0.072(3) Uiso 0.610(14) R . 1
O4B O 0.539(7) 0.5327(8) 0.5657(11) 0.106(6) Uani 0.390(14) D U 2
O5B O 0.449(4) 0.7396(5) 0.4903(5) 0.058(4) Uani 0.390(14) D U 2
H5B H 0.253(4) 0.7512(5) 0.5055(5) 0.070(5) Uiso 0.390(14) R . 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.372(7) . ?
O1 C17 1.435(7) . ?
O2 C11 1.362(7) . ?
O2 C18 1.425(7) . ?
O3 C15 1.399(8) . ?
O3 C16 1.422(8) . ?
C1 C2 1.366(8) . ?
C1 C14 1.420(7) . ?
C2 C3 1.410(8) . ?
C3 C4 1.367(8) . ?
C4 C5 1.406(8) . ?
C5 C6 1.438(8) . ?
C5 C14 1.409(7) . ?
C6 C7 1.346(8) . ?
C6 C15 1.495(8) . ?
C7 C8 1.419(8) . ?
C7 C16 1.504(9) . ?
C8 C9 1.408(8) . ?
C8 C13 1.422(7) . ?
C9 C10 1.377(9) . ?
C10 C11 1.393(9) . ?
C11 C12 1.379(8) . ?
C12 C13 1.416(7) . ?
C13 C14 1.476(8) . ?
C15 O4A 1.128(9) . ?
C15 O5B 1.486(12) . ?
C16 O5A 1.361(10) . ?
C16 O4B 1.137(14) . ?

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
C17 O1 C2 117.3(4) . . ?
C18 O2 C11 117.7(5) . . ?
C16 O3 C15 110.9(5) . . ?
C14 C1 C2 121.2(5) . . ?
C1 C2 O1 125.6(5) . . ?
C3 C2 O1 114.2(5) . . ?
C3 C2 C1 120.2(5) . . ?
C4 C3 C2 119.8(6) . . ?
C5 C4 C3 120.9(5) . . ?
C6 C5 C4 123.2(5) . . ?
C14 C5 C4 120.0(5) . . ?
C14 C5 C6 116.8(5) . . ?
C7 C6 C5 122.5(5) . . ?
C15 C6 C5 128.3(6) . . ?
C15 C6 C7 109.2(6) . . ?
C8 C7 C6 123.2(5) . . ?
C16 C7 C6 108.8(5) . . ?
C16 C7 C8 128.0(6) . . ?
C9 C8 C7 123.0(5) . . ?
C13 C8 C7 117.3(5) . . ?
C13 C8 C9 119.6(5) . . ?
C10 C9 C8 120.6(6) . . ?
C11 C10 C9 120.5(6) . . ?
C10 C11 O2 113.8(6) . . ?
C12 C11 O2 126.2(5) . . ?
C12 C11 C10 120.0(5) . . ?
C13 C12 C11 121.3(5) . . ?
C12 C13 C8 117.9(5) . . ?
C14 C13 C8 119.5(5) . . ?
C14 C13 C12 122.6(5) . . ?
C5 C14 C1 117.9(5) . . ?
C13 C14 C1 121.4(5) . . ?
C13 C14 C5 120.7(5) . . ?
C6 C15 O3 105.9(6) . . ?
C7 C16 O3 105.1(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C15 O4A 1 1.2400 0.0200 0.1124
C15 O5B 1 1.4500 0.0200 -0.0356
C16 O4B 1 1.2400 0.0200 0.1032
O5A C16 1 1.4500 0.0200 0.0892

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
O3 0.0100
O4A 0.0200
O5A 0.0100
O4B 0.0200
O5B 0.0100

####################################################################### 
# 
# 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_1(1-Naph)
_database_code_depnum_ccdc_archive 'CCDC 2059407'
loop_
_audit_author_name
_audit_author_address
'Yu Hai'
;State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matte
China
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C24 H16 O3, C24 H15 O3, C4 H8 O2'
_chemical_formula_sum            'C52 H39 O8'
_chemical_formula_weight         791.88
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H -0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.01500 0.00700 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04100 0.02500 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.37670(10)
_cell_length_b                   27.2161(5)
_cell_length_c                   19.7147(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.144(2)
_cell_angle_gamma                90
_cell_volume                     3947.67(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.1500
_cell_measurement_reflns_used    4630
_cell_measurement_theta_min      2.5471
_cell_measurement_theta_max      27.5398
_exptl_absorpt_coefficient_mu    0.463
_exptl_crystal_density_diffrn    1.3323
_exptl_crystal_F_000             1664.2406
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_description       Prism
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28325
_diffrn_reflns_theta_full        54.8218
_diffrn_reflns_theta_max         54.82
_diffrn_reflns_theta_min         2.41
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9760
_diffrn_measured_fraction_theta_max 0.9760
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.3405
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              33
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -7
_reflns_number_gt                5528
_reflns_number_total             7291
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         1.0128
_refine_diff_density_min         -0.5436
_refine_diff_density_rms         0.0736
_refine_ls_d_res_high            0.8200
_refine_ls_d_res_low             15.9385
_refine_ls_goodness_of_fit_ref   1.0796
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    74
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0830
_refine_ls_restrained_S_all      1.0796
_refine_ls_shift/su_max          0.0055
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1001P)²+3.8523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2312
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C26(H26a,H26b), C28(H28a,H28b), C27(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C46(H46), C23(H23), C49(H49), C12(H12), C22(H22), C8(H8a), C47(H47),
  C41(H41), C6(H6), C16(H16), C20(H20), C21(H21), C51(H51), C48(H48), C18(H18),
 C10(H10), C53(H53), C34(H34), C52(H52), C11(H11), C17(H17), C7(H7), C40(H40),
 C35(H35), C36(H36), C39(H39), C38(H38)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O8(H8)
;
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_refinement_flags_posn
O4 O 0.4454(4) 0.61159(8) 0.23700(13) 0.0619(7) Uani 1.000000 .
O7 O 0.8866(3) 0.56100(9) 0.27865(14) 0.0626(7) Uani 1.000000 .
O3 O 0.3975(4) 0.65367(10) 0.33550(13) 0.0644(7) Uani 1.000000 .
H3 H 0.374(6) 0.6359(11) 0.3673(4) 0.0966(10) Uiso 1.000000 GR
O5 O 0.5663(4) 0.62447(10) 0.13824(15) 0.0739(8) Uani 1.000000 .
O8 O 0.8935(5) 0.56828(11) 0.16157(18) 0.0868(9) Uani 1.000000 .
H8 H 0.790(2) 0.579(2) 0.155(2) 0.1303(14) Uiso 1.000000 GR
O6 O 0.7098(5) 0.55644(13) 0.36517(16) 0.0956(11) Uani 1.000000 .
C14 C 0.5567(4) 0.46607(11) 0.11240(16) 0.0436(7) Uani 1.000000 .
O2 O 0.2808(5) 0.59554(13) 0.42929(17) 0.0966(11) Uani 1.000000 .
C2 C 0.6678(4) 0.49989(11) 0.27117(17) 0.0450(7) Uani 1.000000 .
C5 C 0.7234(4) 0.46551(11) 0.15330(17) 0.0452(7) Uani 1.000000 .
C42 C 0.1604(5) 0.71485(11) 0.07007(17) 0.0484(8) Uani 1.000000 .
C43 C 0.2420(4) 0.67723(10) 0.23198(17) 0.0451(7) Uani 1.000000 .
C45 C 0.1440(4) 0.75790(11) 0.28168(16) 0.0430(7) Uani 1.000000 .
C24 C 0.5539(4) 0.41827(11) 0.31263(16) 0.0440(7) Uani 1.000000 .
C1 C 0.7509(4) 0.49802(11) 0.21325(18) 0.0455(7) Uani 1.000000 .
C13 C 0.4080(4) 0.49743(12) 0.12467(18) 0.0482(8) Uani 1.000000 .
H13 H 0.4164(4) 0.51802(12) 0.16242(18) 0.0579(9) Uiso 1.000000 R
C15 C 0.5209(4) 0.46906(11) 0.29665(16) 0.0448(7) Uani 1.000000 .
C50 C 0.0065(4) 0.78540(12) 0.31149(17) 0.0481(8) Uani 1.000000 .
C9 C 0.5393(5) 0.43541(12) 0.05400(17) 0.0504(8) Uani 1.000000 .
C46 C 0.3158(4) 0.77993(12) 0.27632(18) 0.0482(8) Uani 1.000000 .
H46 H 0.4076(4) 0.76231(12) 0.25737(18) 0.0578(9) Uiso 1.000000 R
C31 C 0.3271(5) 0.67763(11) 0.17434(18) 0.0479(8) Uani 1.000000 .
C19 C 0.4118(4) 0.39097(12) 0.33940(17) 0.0492(8) Uani 1.000000 .
C44 C 0.0999(4) 0.70901(11) 0.25890(17) 0.0465(7) Uani 1.000000 .
C30 C 0.3147(5) 0.63590(12) 0.27689(18) 0.0500(8) Uani 1.000000 .
H30 H 0.2167(5) 0.61325(12) 0.28670(18) 0.0600(9) Uiso 1.000000 R
C23 C 0.7220(4) 0.39500(11) 0.30590(18) 0.0487(8) Uani 1.000000 .
H23 H 0.8167(4) 0.41250(11) 0.28866(18) 0.0584(9) Uiso 1.000000 R
C29 C 0.4590(5) 0.63612(12) 0.17824(19) 0.0540(8) Uani 1.000000 .
C33 C 0.3178(5) 0.71167(11) 0.11613(17) 0.0486(8) Uani 1.000000 .
C49 C 0.0460(5) 0.83426(13) 0.33277(19) 0.0562(9) Uani 1.000000 .
H49 H -0.0440(5) 0.85292(13) 0.35114(19) 0.0674(11) Uiso 1.000000 R
C3 C 0.7477(5) 0.54095(13) 0.31257(19) 0.0561(9) Uani 1.000000 .
O1 O 0.1315(7) 0.55433(17) 0.54147(19) 0.1140(13) Uani 1.000000 .
C37 C 0.1597(5) 0.74725(13) 0.01412(19) 0.0579(9) Uani 1.000000 .
C4 C 0.9002(5) 0.53674(12) 0.2146(2) 0.0591(9) Uani 1.000000 .
C12 C 0.2551(5) 0.49792(14) 0.08264(19) 0.0574(9) Uani 1.000000 .
H12 H 0.1601(5) 0.51878(14) 0.09180(19) 0.0688(11) Uiso 1.000000 R
C22 C 0.7477(5) 0.34675(12) 0.3245(2) 0.0586(9) Uani 1.000000 .
H22 H 0.8597(5) 0.33186(12) 0.3201(2) 0.0703(11) Uiso 1.000000 R
C8 C 0.6853(6) 0.40486(13) 0.0392(2) 0.0634(10) Uani 1.000000 .
H8a H 0.6729(6) 0.38412(13) 0.0016(2) 0.0761(12) Uiso 1.000000 R
C47 C 0.3486(5) 0.82688(12) 0.2987(2) 0.0572(9) Uani 1.000000 .
H47 H 0.4626(5) 0.84086(12) 0.2952(2) 0.0686(11) Uiso 1.000000 R
C41 C 0.0013(5) 0.68536(14) 0.0775(2) 0.0605(9) Uani 1.000000 .
H41 H -0.0016(5) 0.66329(14) 0.1134(2) 0.0726(11) Uiso 1.000000 R
C6 C 0.8629(5) 0.43623(13) 0.1358(2) 0.0574(9) Uani 1.000000 .
H6 H 0.9728(5) 0.43679(13) 0.1621(2) 0.0689(11) Uiso 1.000000 R
C16 C 0.3588(5) 0.48999(14) 0.3092(2) 0.0595(9) Uani 1.000000 .
H16 H 0.3404(5) 0.52327(14) 0.3004(2) 0.0714(11) Uiso 1.000000 R
C20 C 0.4435(5) 0.34093(13) 0.3573(2) 0.0588(9) Uani 1.000000 .
H20 H 0.3505(5) 0.32255(13) 0.3741(2) 0.0705(11) Uiso 1.000000 R
C21 C 0.6054(5) 0.31974(13) 0.3503(2) 0.0625(10) Uani 1.000000 .
H21 H 0.6236(5) 0.28702(13) 0.3625(2) 0.0750(12) Uiso 1.000000 R
C51 C -0.1649(5) 0.76396(14) 0.3188(2) 0.0605(9) Uani 1.000000 .
H51 H -0.2546(5) 0.78203(14) 0.3383(2) 0.0726(11) Uiso 1.000000 R
C48 C 0.2107(5) 0.85409(13) 0.3269(2) 0.0606(9) Uani 1.000000 .
H48 H 0.2337(5) 0.88609(13) 0.3417(2) 0.0727(11) Uiso 1.000000 R
C18 C 0.2444(5) 0.41384(15) 0.34901(19) 0.0611(10) Uani 1.000000 .
H18 H 0.1502(5) 0.39553(15) 0.36516(19) 0.0733(11) Uiso 1.000000 R
C10 C 0.3753(6) 0.43711(14) 0.01129(19) 0.0629(10) Uani 1.000000 .
H10 H 0.3623(6) 0.41710(14) -0.02698(19) 0.0755(12) Uiso 1.000000 R
C53 C -0.0672(5) 0.69002(13) 0.2676(2) 0.0590(9) Uani 1.000000 .
H53 H -0.0933(5) 0.65809(13) 0.2532(2) 0.0708(11) Uiso 1.000000 R
C34 C 0.4666(5) 0.73891(13) 0.1040(2) 0.0614(9) Uani 1.000000 .
H34 H 0.5713(5) 0.73579(13) 0.1329(2) 0.0736(11) Uiso 1.000000 R
C52 C -0.2008(5) 0.71724(15) 0.2976(2) 0.0637(10) Uani 1.000000 .
H52 H -0.3141(5) 0.70338(15) 0.3030(2) 0.0765(12) Uiso 1.000000 R
C11 C 0.2382(6) 0.46752(16) 0.0258(2) 0.0674(10) Uani 1.000000 .
H11 H 0.1318(6) 0.46812(16) -0.0026(2) 0.0809(13) Uiso 1.000000 R
C17 C 0.2188(5) 0.46216(16) 0.3350(2) 0.0671(10) Uani 1.000000 .
H17 H 0.1084(5) 0.47697(16) 0.3426(2) 0.0805(13) Uiso 1.000000 R
C7 C 0.8432(6) 0.40513(13) 0.0785(2) 0.0650(10) Uani 1.000000 .
H7 H 0.9386(6) 0.38487(13) 0.0678(2) 0.0780(12) Uiso 1.000000 R
C40 C -0.1455(6) 0.68989(16) 0.0316(2) 0.0704(11) Uani 1.000000 .
H40 H -0.2484(6) 0.67083(16) 0.0364(2) 0.0845(13) Uiso 1.000000 R
C35 C 0.4664(6) 0.77176(16) 0.0487(2) 0.0718(11) Uani 1.000000 .
H35 H 0.5688(6) 0.79064(16) 0.0423(2) 0.0861(13) Uiso 1.000000 R
C36 C 0.3184(6) 0.77580(15) 0.0053(2) 0.0714(11) Uani 1.000000 .
H36 H 0.3193(6) 0.79754(15) -0.0311(2) 0.0857(13) Uiso 1.000000 R
C39 C -0.1421(6) 0.72304(18) -0.0226(2) 0.0775(12) Uani 1.000000 .
H39 H -0.2437(6) 0.72589(18) -0.0531(2) 0.0930(14) Uiso 1.000000 R
C38 C 0.0037(6) 0.75059(17) -0.0313(2) 0.0742(12) Uani 1.000000 .
H38 H 0.0025(6) 0.77228(17) -0.0677(2) 0.0891(14) Uiso 1.000000 R
C25 C 0.3901(8) 0.5764(3) 0.4839(3) 0.1077(19) Uani 1.000000 .
H25a H 0.5001(8) 0.5627(3) 0.4674(3) 0.129(2) Uiso 1.000000 R
H25b H 0.4247(8) 0.6025(3) 0.5157(3) 0.129(2) Uiso 1.000000 R
C26 C 0.2945(10) 0.5386(2) 0.5184(3) 0.113(2) Uani 1.000000 .
H26a H 0.3720(10) 0.5268(2) 0.5568(3) 0.136(2) Uiso 1.000000 R
H26b H 0.2709(10) 0.5112(2) 0.4875(3) 0.136(2) Uiso 1.000000 R
C28 C 0.1109(11) 0.6119(2) 0.4509(4) 0.129(2) Uani 1.000000 .
H28a H 0.1299(11) 0.6405(2) 0.4799(4) 0.155(3) Uiso 1.000000 R
H28b H 0.0321(11) 0.6215(2) 0.4115(4) 0.155(3) Uiso 1.000000 R
C27 C 0.0243(9) 0.5734(3) 0.4877(4) 0.131(2) Uani 1.000000 .
H27a H -0.0104(9) 0.5470(3) 0.4564(4) 0.157(3) Uiso 1.000000 R
H27b H -0.0861(9) 0.5865(3) 0.5048(4) 0.157(3) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C30 1.447(4) . ?
O4 C29 1.347(4) . ?
O7 C3 1.377(4) . ?
O7 C4 1.434(5) . ?
O3 C30 1.356(4) . ?
O5 C29 1.200(4) . ?
O8 C4 1.351(5) . ?
O6 C3 1.172(5) . ?
C14 C5 1.421(5) . ?
C14 C13 1.424(5) . ?
C14 C9 1.420(5) . ?
O2 C25 1.399(6) . ?
O2 C28 1.424(7) . ?
C2 C1 1.336(5) . ?
C2 C15 1.486(4) . ?
C2 C3 1.481(5) . ?
C5 C1 1.479(5) . ?
C5 C6 1.365(5) . ?
C42 C33 1.424(5) . ?
C42 C37 1.412(5) . ?
C42 C41 1.438(5) . ?
C43 C31 1.337(5) . ?
C43 C44 1.486(4) . ?
C43 C30 1.506(4) . ?
C45 C50 1.421(4) . ?
C45 C46 1.413(5) . ?
C45 C44 1.434(4) . ?
C24 C15 1.435(4) . ?
C24 C19 1.417(4) . ?
C24 C23 1.407(5) . ?
C1 C4 1.523(5) . ?
C13 C12 1.350(5) . ?
C15 C16 1.363(5) . ?
C50 C49 1.418(5) . ?
C50 C51 1.410(5) . ?
C9 C8 1.408(5) . ?
C9 C10 1.424(5) . ?
C46 C47 1.368(5) . ?
C31 C29 1.489(5) . ?
C31 C33 1.473(5) . ?
C19 C20 1.422(5) . ?
C19 C18 1.408(5) . ?
C44 C53 1.359(5) . ?
C23 C22 1.373(5) . ?
C33 C34 1.360(5) . ?
C49 C48 1.341(5) . ?
O1 C26 1.384(7) . ?
O1 C27 1.377(8) . ?
C37 C36 1.426(6) . ?
C37 C38 1.408(6) . ?
C12 C11 1.392(6) . ?
C22 C21 1.406(5) . ?
C8 C7 1.352(6) . ?
C47 C48 1.405(5) . ?
C41 C40 1.366(5) . ?
C6 C7 1.411(6) . ?
C16 C17 1.406(5) . ?
C20 C21 1.342(5) . ?
C51 C52 1.359(5) . ?
C18 C17 1.354(6) . ?
C10 C11 1.353(6) . ?
C53 C52 1.398(5) . ?
C34 C35 1.410(5) . ?
C40 C39 1.400(6) . ?
C35 C36 1.342(6) . ?
C39 C38 1.333(6) . ?
C25 C26 1.444(8) . ?
C28 C27 1.450(9) . ?

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
C29 O4 C30 109.6(2) . . ?
C4 O7 C3 110.3(3) . . ?
C13 C14 C5 123.8(3) . . ?
C9 C14 C5 118.5(3) . . ?
C9 C14 C13 117.7(3) . . ?
C28 O2 C25 111.0(4) . . ?
C15 C2 C1 131.2(3) . . ?
C3 C2 C1 108.1(3) . . ?
C3 C2 C15 120.7(3) . . ?
C1 C5 C14 120.7(3) . . ?
C6 C5 C14 120.0(3) . . ?
C6 C5 C1 119.2(3) . . ?
C37 C42 C33 119.5(3) . . ?
C41 C42 C33 122.3(3) . . ?
C41 C42 C37 118.1(3) . . ?
C44 C43 C31 133.2(3) . . ?
C30 C43 C31 109.7(3) . . ?
C30 C43 C44 117.1(3) . . ?
C46 C45 C50 118.6(3) . . ?
C44 C45 C50 117.8(3) . . ?
C44 C45 C46 123.7(3) . . ?
C19 C24 C15 118.0(3) . . ?
C23 C24 C15 123.3(3) . . ?
C23 C24 C19 118.7(3) . . ?
C5 C1 C2 131.4(3) . . ?
C4 C1 C2 109.5(3) . . ?
C4 C1 C5 119.1(3) . . ?
C12 C13 C14 121.4(3) . . ?
C24 C15 C2 120.1(3) . . ?
C16 C15 C2 119.7(3) . . ?
C16 C15 C24 120.0(3) . . ?
C49 C50 C45 118.6(3) . . ?
C51 C50 C45 119.8(3) . . ?
C51 C50 C49 121.6(3) . . ?
C8 C9 C14 119.3(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C8 121.8(3) . . ?
C47 C46 C45 120.7(3) . . ?
C29 C31 C43 107.1(3) . . ?
C33 C31 C43 132.0(3) . . ?
C33 C31 C29 120.7(3) . . ?
C20 C19 C24 118.8(3) . . ?
C18 C19 C24 119.8(3) . . ?
C18 C19 C20 121.4(3) . . ?
C45 C44 C43 120.1(3) . . ?
C53 C44 C43 119.6(3) . . ?
C53 C44 C45 120.0(3) . . ?
O3 C30 O4 110.5(3) . . ?
C43 C30 O4 104.2(3) . . ?
C43 C30 O3 110.7(3) . . ?
C22 C23 C24 120.7(3) . . ?
O5 C29 O4 121.9(3) . . ?
C31 C29 O4 109.3(3) . . ?
C31 C29 O5 128.8(3) . . ?
C31 C33 C42 121.7(3) . . ?
C34 C33 C42 119.1(3) . . ?
C34 C33 C31 119.2(3) . . ?
C48 C49 C50 121.3(3) . . ?
O6 C3 O7 121.4(3) . . ?
C2 C3 O7 108.2(3) . . ?
C2 C3 O6 130.4(4) . . ?
C27 O1 C26 109.1(4) . . ?
C36 C37 C42 118.6(3) . . ?
C38 C37 C42 119.6(4) . . ?
C38 C37 C36 121.8(4) . . ?
O8 C4 O7 112.8(3) . . ?
C1 C4 O7 103.8(3) . . ?
C1 C4 O8 116.1(3) . . ?
C11 C12 C13 120.7(4) . . ?
C21 C22 C23 120.3(3) . . ?
C7 C8 C9 121.2(4) . . ?
C48 C47 C46 120.2(3) . . ?
C40 C41 C42 119.7(4) . . ?
C7 C6 C5 121.1(4) . . ?
C17 C16 C15 121.2(3) . . ?
C21 C20 C19 121.2(3) . . ?
C20 C21 C22 120.4(3) . . ?
C52 C51 C50 120.8(3) . . ?
C47 C48 C49 120.5(3) . . ?
C17 C18 C19 120.8(3) . . ?
C11 C10 C9 120.8(4) . . ?
C52 C53 C44 121.7(3) . . ?
C35 C34 C33 121.7(4) . . ?
C53 C52 C51 119.9(3) . . ?
C10 C11 C12 120.6(4) . . ?
C18 C17 C16 120.1(3) . . ?
C6 C7 C8 119.8(3) . . ?
C39 C40 C41 120.5(4) . . ?
C36 C35 C34 120.0(4) . . ?
C35 C36 C37 121.0(4) . . ?
C38 C39 C40 121.3(4) . . ?
C39 C38 C37 120.8(4) . . ?
C26 C25 O2 110.7(5) . . ?
C25 C26 O1 113.6(5) . . ?
C27 C28 O2 110.6(5) . . ?
C28 C27 O1 114.2(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1(H)
_database_code_depnum_ccdc_archive 'CCDC 2059408'
loop_
_audit_author_name
_audit_author_address
'Yu Hai'
;State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matte
China
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C16 H12 O3'
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.27
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 x+1/3,y+2/3,z+2/3
8 -y+1/3,x-y+2/3,z+2/3
9 -x+y+1/3,-x+2/3,z+2/3
10 -x+1/3,-y+2/3,-z+2/3
11 y+1/3,-x+y+2/3,-z+2/3
12 x-y+1/3,x+2/3,-z+2/3
13 x+2/3,y+1/3,z+1/3
14 -y+2/3,x-y+1/3,z+1/3
15 -x+y+2/3,-x+1/3,z+1/3
16 -x+2/3,-y+1/3,-z+1/3
17 y+2/3,-x+y+1/3,-z+1/3
18 x-y+2/3,x+1/3,-z+1/3

_symmetry_Int_Tables_number      148
_cell_length_a                   58.934(3)
_cell_length_b                   58.934(3)
_cell_length_c                   5.7790(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     17382.4(16)
_cell_formula_units_Z            54
_cell_measurement_temperature    193.1500
_cell_measurement_reflns_used    12237
_cell_measurement_theta_min      2.0734
_cell_measurement_theta_max      27.4932
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_description       Prism
_exptl_crystal_density_diffrn    1.3013
_exptl_crystal_F_000             7132.0527
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_limit_h_max       73
_diffrn_reflns_limit_h_min       -76
_diffrn_reflns_limit_k_max       76
_diffrn_reflns_limit_k_min       -76
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            46793
_diffrn_reflns_theta_full        27.4320
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.07
_diffrn_ambient_temperature      193.15
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              65
_reflns_limit_h_min              0
_reflns_limit_k_max              66
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              -7
_reflns_number_gt                6780
_reflns_number_total             8825
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         1.3796
_refine_diff_density_min         -0.4992
_refine_diff_density_rms         0.1264
_refine_ls_d_res_high            0.7714
_refine_ls_d_res_low             9.8223
_refine_ls_goodness_of_fit_ref   1.0368
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     517
_refine_ls_number_reflns         8825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1759
_refine_ls_R_factor_gt           0.1395
_refine_ls_restrained_S_all      1.0368
_refine_ls_shift/su_max          0.0023
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+171.3301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2708
_refine_ls_wR_factor_ref         0.2933
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C37(H37), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C36(H36), C40(H40), C46(H46), C52(H52), C53(H53), C54(H54),
 C55(H55), C56(H56), C57(H57), C13(H13), C22(H22), C25(H25), C27(H27), C32(H32),
  C35(H35), C41(H41), C43(H43), C44(H44), C49(H49), C23(H23), C31(H31),
 C33(H33), C39(H39), C42(H42), C45(H45), C47(H47), C48(H48), C50(H50), C51(H51)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O7(H7)
;
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_refinement_flags_posn
O1 O 0.00588(8) 0.18875(8) 0.0705(7) 0.0666(11) Uani 1.000000 .
H1 H -0.0078(4) 0.1791(9) -0.005(8) 0.0799(13) Uiso 1.000000 GR
O2 O 0.04193(7) 0.18850(7) 0.2137(7) 0.0638(10) Uani 1.000000 .
O6 O 0.05634(8) 0.16656(8) 0.4275(7) 0.0744(12) Uani 1.000000 .
C12 C 0.02868(10) 0.12125(11) 0.1040(10) 0.0557(13) Uani 1.000000 .
C14 C 0.01537(9) 0.15435(10) -0.0402(9) 0.0491(12) Uani 1.000000 .
C17 C -0.00499(9) 0.13986(10) -0.2161(8) 0.0480(11) Uani 1.000000 .
C20 C 0.02787(9) 0.14595(10) 0.0998(9) 0.0478(11) Uani 1.000000 .
C24 C 0.02491(10) 0.18288(10) 0.0122(9) 0.0527(12) Uani 1.000000 .
H24 H 0.03536(10) 0.19398(10) -0.1213(9) 0.0632(15) Uiso 1.000000 R
C34 C -0.02171(10) 0.11292(11) -0.1947(10) 0.0601(14) Uani 1.000000 .
H34 H -0.01957(10) 0.10371(11) -0.0695(10) 0.0721(17) Uiso 1.000000 R
C36 C -0.00870(11) 0.15288(11) -0.4009(9) 0.0567(13) Uani 1.000000 .
H36 H 0.00227(11) 0.17129(11) -0.4169(9) 0.0681(16) Uiso 1.000000 R
C38 C 0.04363(10) 0.16702(11) 0.2647(10) 0.0574(13) Uani 1.000000 .
C40 C -0.02844(11) 0.13897(13) -0.5624(10) 0.0630(15) Uani 1.000000 .
H40 H -0.03064(11) 0.14788(13) -0.6897(10) 0.0756(18) Uiso 1.000000 R
C46 C -0.04472(11) 0.11245(13) -0.5382(10) 0.0681(16) Uani 1.000000 .
H46 H -0.05824(11) 0.10305(13) -0.6479(10) 0.0817(19) Uiso 1.000000 R
C52 C 0.01982(13) 0.10492(12) 0.2948(12) 0.0727(17) Uani 1.000000 .
H52 H 0.01188(13) 0.10867(12) 0.4209(12) 0.087(2) Uiso 1.000000 R
C53 C 0.04023(13) 0.11560(14) -0.0784(12) 0.0787(19) Uani 1.000000 .
H53 H 0.04607(13) 0.12679(14) -0.2098(12) 0.094(2) Uiso 1.000000 R
C54 C -0.04142(11) 0.09956(12) -0.3552(11) 0.0684(16) Uani 1.000000 .
H54 H -0.05282(11) 0.08123(12) -0.3384(11) 0.0820(19) Uiso 1.000000 R
C55 C 0.04338(18) 0.09398(19) -0.0721(16) 0.105(3) Uani 1.000000 .
H55 H 0.05141(18) 0.09028(19) -0.1978(16) 0.126(3) Uiso 1.000000 R
C56 C 0.02276(18) 0.08267(15) 0.2990(16) 0.103(3) Uani 1.000000 .
H56 H 0.01646(18) 0.07097(15) 0.4268(16) 0.124(3) Uiso 1.000000 R
C57 C 0.0349(2) 0.07799(18) 0.116(2) 0.118(3) Uani 1.000000 .
H57 H 0.0373(2) 0.06325(18) 0.122(2) 0.141(4) Uiso 1.000000 R
O3 O 0.08633(7) 0.20079(7) 0.7560(7) 0.0629(10) Uani 1.000000 .
H3 H 0.0769(10) 0.19030(15) 0.652(5) 0.0755(12) Uiso 1.000000 GR
O4 O 0.11087(8) 0.27282(8) 1.1179(8) 0.0705(12) Uani 1.000000 .
O5 O 0.08772(6) 0.23803(7) 0.8890(7) 0.0607(10) Uani 1.000000 .
C11 C 0.13181(9) 0.26380(9) 0.7985(8) 0.0438(11) Uani 1.000000 .
C13 C 0.12250(10) 0.22057(9) 0.2879(9) 0.0511(12) Uani 1.000000 .
H13 H 0.10432(10) 0.21444(9) 0.2695(9) 0.0613(14) Uiso 1.000000 R
C15 C 0.12240(9) 0.24351(9) 0.6505(8) 0.0426(11) Uani 1.000000 .
C16 C 0.15782(9) 0.28780(9) 0.8204(8) 0.0429(11) Uani 1.000000 .
C18 C 0.13582(9) 0.23637(9) 0.4772(8) 0.0412(10) Uani 1.000000 .
C21 C 0.11007(11) 0.25966(10) 0.9526(10) 0.0559(13) Uani 1.000000 .
C22 C 0.16725(10) 0.30581(9) 0.6405(9) 0.0492(12) Uani 1.000000 .
H22 H 0.15754(10) 0.30218(9) 0.5008(9) 0.0591(14) Uiso 1.000000 R
C25 C 0.16245(10) 0.24453(10) 0.5020(9) 0.0483(11) Uani 1.000000 .
H25 H 0.17185(10) 0.25500(10) 0.6311(9) 0.0580(14) Uiso 1.000000 R
C27 C 0.17228(10) 0.29315(10) 1.0229(9) 0.0524(12) Uani 1.000000 .
H27 H 0.16611(10) 0.28093(10) 1.1469(9) 0.0629(15) Uiso 1.000000 R
C32 C 0.17523(11) 0.23761(11) 0.3419(10) 0.0572(13) Uani 1.000000 .
H32 H 0.19334(11) 0.24340(11) 0.3603(10) 0.0687(16) Uiso 1.000000 R
C35 C 0.19088(11) 0.32915(10) 0.6642(11) 0.0582(14) Uani 1.000000 .
H35 H 0.19721(11) 0.34138(10) 0.5403(11) 0.0699(17) Uiso 1.000000 R
C37 C 0.09316(9) 0.22602(10) 0.6928(9) 0.0520(12) Uani 1.000000 .
H37 H 0.08293(9) 0.22584(10) 0.5541(9) 0.0624(15) Uiso 1.000000 R
C41 C 0.19605(11) 0.31672(12) 1.0426(11) 0.0641(15) Uani 1.000000 .
H41 H 0.20604(11) 0.32038(12) 1.1806(11) 0.0769(19) Uiso 1.000000 R
C43 C 0.13538(12) 0.21369(11) 0.1263(9) 0.0589(14) Uani 1.000000 .
H43 H 0.12611(12) 0.20315(11) -0.0029(9) 0.0707(16) Uiso 1.000000 R
C44 C 0.16157(12) 0.22211(12) 0.1533(10) 0.0621(15) Uani 1.000000 .
H44 H 0.17038(12) 0.21734(12) 0.0428(10) 0.0746(17) Uiso 1.000000 R
C49 C 0.20514(11) 0.33467(11) 0.8648(11) 0.0629(15) Uani 1.000000 .
H49 H 0.22115(11) 0.35075(11) 0.8809(11) 0.0754(18) Uiso 1.000000 R
O7 O 0.07678(7) 0.28088(9) 0.3672(8) 0.0730(12) Uani 1.000000 .
H7 H 0.08936(10) 0.2796(5) 0.314(10) 0.0876(14) Uiso 1.000000 GR
C8 C 0.01165(9) 0.24979(9) 0.4148(8) 0.0431(11) Uani 1.000000 .
O9 O 0.04447(8) 0.24100(8) 0.5146(7) 0.0695(11) Uani 1.000000 .
C10 C 0.03144(9) 0.26429(10) 0.2704(9) 0.0466(11) Uani 1.000000 .
O19 O 0.00858(9) 0.22225(9) 0.7384(8) 0.0813(13) Uani 1.000000 .
C23 C 0.02069(9) 0.29779(10) 0.1320(9) 0.0501(12) Uani 1.000000 .
H23 H 0.00986(9) 0.29441(10) 0.2641(9) 0.0601(14) Uiso 1.000000 R
C26 C 0.02028(11) 0.23587(10) 0.5744(10) 0.0571(13) Uani 1.000000 .
C28 C 0.03394(8) 0.28384(9) 0.1007(8) 0.0440(11) Uani 1.000000 .
C29 C 0.05341(11) 0.25842(11) 0.3140(10) 0.0595(14) Uani 1.000000 .
H29 H 0.05572(11) 0.24937(11) 0.1773(10) 0.0714(17) Uiso 1.000000 R
C30 C -0.01531(9) 0.24568(9) 0.4288(8) 0.0440(11) Uani 1.000000 .
C31 C 0.05004(10) 0.28974(10) -0.0949(9) 0.0521(12) Uani 1.000000 .
H31 H 0.05969(10) 0.28097(10) -0.1188(9) 0.0625(15) Uiso 1.000000 R
C33 C -0.02394(10) 0.25280(10) 0.6230(9) 0.0527(12) Uani 1.000000 .
H33 H -0.01246(10) 0.26067(10) 0.7506(9) 0.0632(15) Uiso 1.000000 R
C39 C 0.02318(11) 0.31640(11) -0.0265(10) 0.0605(14) Uani 1.000000 .
H39 H 0.01416(11) 0.32578(11) -0.0024(10) 0.0726(17) Uiso 1.000000 R
C42 C -0.03237(10) 0.23381(10) 0.2453(9) 0.0561(13) Uani 1.000000 .
H42 H -0.02672(10) 0.22863(10) 0.1116(9) 0.0674(16) Uiso 1.000000 R
C45 C 0.05197(11) 0.30822(11) -0.2529(10) 0.0627(15) Uani 1.000000 .
H45 H 0.06267(11) 0.31174(11) -0.3861(10) 0.0753(18) Uiso 1.000000 R
C47 C 0.03879(11) 0.32147(11) -0.2210(10) 0.0629(15) Uani 1.000000 .
H47 H 0.04028(11) 0.33410(11) -0.3312(10) 0.0755(18) Uiso 1.000000 R
C48 C -0.06600(11) 0.23705(12) 0.4505(12) 0.0699(17) Uani 1.000000 .
H48 H -0.08331(11) 0.23427(12) 0.4571(12) 0.084(2) Uiso 1.000000 R
C50 C -0.04926(11) 0.24852(12) 0.6322(11) 0.0656(15) Uani 1.000000 .
H50 H -0.05503(11) 0.25359(12) 0.7657(11) 0.0787(18) Uiso 1.000000 R
C51 C -0.05766(11) 0.22952(12) 0.2578(11) 0.0690(17) Uani 1.000000 .
H51 H -0.06938(11) 0.22131(12) 0.1323(11) 0.083(2) Uiso 1.000000 R


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 C24 1.371(6) . ?
O2 C24 1.462(6) . ?
O2 C38 1.351(6) . ?
O6 C38 1.212(6) . ?
C12 C20 1.480(7) . ?
C12 C52 1.383(8) . ?
C12 C53 1.383(8) . ?
C14 C17 1.476(7) . ?
C14 C20 1.345(7) . ?
C14 C24 1.513(7) . ?
C17 C34 1.393(7) . ?
C17 C36 1.395(7) . ?
C20 C38 1.469(7) . ?
C34 C54 1.384(8) . ?
C36 C40 1.394(8) . ?
C40 C46 1.372(8) . ?
C46 C54 1.371(8) . ?
C52 C56 1.406(10) . ?
C53 C55 1.377(10) . ?
C55 C57 1.360(13) . ?
C56 C57 1.378(12) . ?
O3 C37 1.381(6) . ?
O4 C21 1.217(6) . ?
O5 C21 1.348(6) . ?
O5 C37 1.455(6) . ?
C11 C15 1.344(7) . ?
C11 C16 1.483(6) . ?
C11 C21 1.477(7) . ?
C13 C18 1.396(7) . ?
C13 C43 1.386(7) . ?
C15 C18 1.462(6) . ?
C15 C37 1.522(6) . ?
C16 C22 1.388(7) . ?
C16 C27 1.388(7) . ?
C18 C25 1.400(6) . ?
C22 C35 1.391(7) . ?
C25 C32 1.377(7) . ?
C27 C41 1.399(8) . ?
C32 C44 1.391(8) . ?
C35 C49 1.372(8) . ?
C41 C49 1.377(8) . ?
C43 C44 1.373(8) . ?
O7 C29 1.386(7) . ?
C8 C10 1.338(7) . ?
C8 C26 1.483(7) . ?
C8 C30 1.485(6) . ?
O9 C26 1.347(7) . ?
O9 C29 1.461(7) . ?
C10 C28 1.463(7) . ?
C10 C29 1.519(7) . ?
O19 C26 1.210(6) . ?
C23 C28 1.400(7) . ?
C23 C39 1.379(7) . ?
C28 C31 1.403(7) . ?
C30 C33 1.381(7) . ?
C30 C42 1.386(7) . ?
C31 C45 1.382(8) . ?
C33 C50 1.385(7) . ?
C39 C47 1.387(8) . ?
C42 C51 1.383(8) . ?
C45 C47 1.361(8) . ?
C48 C50 1.366(8) . ?
C48 C51 1.377(9) . ?

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
C38 O2 C24 109.0(4) . . ?
C52 C12 C20 120.7(5) . . ?
C53 C12 C20 119.1(6) . . ?
C53 C12 C52 120.0(6) . . ?
C20 C14 C17 129.6(5) . . ?
C24 C14 C17 121.6(4) . . ?
C24 C14 C20 108.7(4) . . ?
C34 C17 C14 120.4(5) . . ?
C36 C17 C14 121.0(5) . . ?
C36 C17 C34 118.6(5) . . ?
C14 C20 C12 131.7(5) . . ?
C38 C20 C12 120.2(4) . . ?
C38 C20 C14 108.1(5) . . ?
O2 C24 O1 107.6(4) . . ?
C14 C24 O1 115.7(4) . . ?
C14 C24 O2 104.1(4) . . ?
C54 C34 C17 120.2(5) . . ?
C40 C36 C17 120.2(5) . . ?
O6 C38 O2 121.8(5) . . ?
C20 C38 O2 109.8(5) . . ?
C20 C38 O6 128.4(5) . . ?
C46 C40 C36 120.3(5) . . ?
C54 C46 C40 119.8(5) . . ?
C56 C52 C12 118.9(7) . . ?
C55 C53 C12 120.9(8) . . ?
C46 C54 C34 120.9(6) . . ?
C57 C55 C53 119.2(8) . . ?
C57 C56 C52 119.4(8) . . ?
C56 C57 C55 121.6(8) . . ?
C37 O5 C21 108.9(4) . . ?
C16 C11 C15 132.3(4) . . ?
C21 C11 C15 107.4(4) . . ?
C21 C11 C16 120.3(4) . . ?
C43 C13 C18 121.0(5) . . ?
C18 C15 C11 130.5(4) . . ?
C37 C15 C11 108.9(4) . . ?
C37 C15 C18 120.5(4) . . ?
C22 C16 C11 119.6(5) . . ?
C27 C16 C11 120.9(4) . . ?
C27 C16 C22 119.5(5) . . ?
C15 C18 C13 121.6(4) . . ?
C25 C18 C13 118.0(4) . . ?
C25 C18 C15 120.4(4) . . ?
O5 C21 O4 121.7(5) . . ?
C11 C21 O4 127.9(5) . . ?
C11 C21 O5 110.4(5) . . ?
C35 C22 C16 120.2(5) . . ?
C32 C25 C18 121.0(5) . . ?
C41 C27 C16 119.4(5) . . ?
C44 C32 C25 119.9(5) . . ?
C49 C35 C22 120.6(5) . . ?
O5 C37 O3 107.5(4) . . ?
C15 C37 O3 113.2(4) . . ?
C15 C37 O5 104.2(4) . . ?
C49 C41 C27 120.9(6) . . ?
C44 C43 C13 119.9(5) . . ?
C43 C44 C32 120.2(5) . . ?
C41 C49 C35 119.4(5) . . ?
C26 C8 C10 108.1(4) . . ?
C30 C8 C10 131.1(4) . . ?
C30 C8 C26 120.7(4) . . ?
C29 O9 C26 109.3(4) . . ?
C28 C10 C8 129.3(4) . . ?
C29 C10 C8 108.7(4) . . ?
C29 C10 C28 121.9(4) . . ?
C39 C23 C28 120.8(5) . . ?
O9 C26 C8 109.5(5) . . ?
O19 C26 C8 128.0(5) . . ?
O19 C26 O9 122.5(5) . . ?
C23 C28 C10 120.6(4) . . ?
C31 C28 C10 121.6(4) . . ?
C31 C28 C23 117.7(5) . . ?
O9 C29 O7 109.4(5) . . ?
C10 C29 O7 111.9(4) . . ?
C10 C29 O9 104.1(4) . . ?
C33 C30 C8 121.4(4) . . ?
C42 C30 C8 119.2(5) . . ?
C42 C30 C33 119.4(5) . . ?
C45 C31 C28 120.4(5) . . ?
C50 C33 C30 120.2(5) . . ?
C47 C39 C23 120.3(5) . . ?
C51 C42 C30 119.7(5) . . ?
C47 C45 C31 121.1(5) . . ?
C45 C47 C39 119.6(5) . . ?
C51 C48 C50 119.7(5) . . ?
C48 C50 C33 120.4(6) . . ?
C48 C51 C42 120.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
