# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_uch111_7MeO_143K
_database_code_depnum_ccdc_archive 'CCDC 2061357'
loop_
_audit_author_name
_audit_author_address
'Kanae Yano'
;Ryukoku University
Japan
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         176.16

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8212(3)
_cell_length_b                   13.3401(5)
_cell_length_c                   18.5886(7)
_cell_angle_alpha                80.8654(17)
_cell_angle_beta                 89.4342(17)
_cell_angle_gamma                81.6705(16)
_cell_volume                     1652.26(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    505
_cell_measurement_theta_min      1.8073
_cell_measurement_theta_max      29.1472
_cell_measurement_temperature    143.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.124
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736

_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      143.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            37034
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             5849
_reflns_number_gt                4795
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1396
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_number_reflns         5849
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+0.2487P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.772
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3689(2) 0.35937(13) 0.17039(9) 0.0353(4) Uani d . . . 1 . .
C C2 0.1868(2) 0.33939(12) 0.20614(9) 0.0341(4) Uani d . . . 1 . .
H H2 0.1816 0.3306 0.2578 0.041 Uiso calc U . R 1 . .
C C3 0.0248(2) 0.33299(12) 0.16782(9) 0.0315(4) Uani d . . . 1 . .
H H3 -0.0929 0.3189 0.1927 0.038 Uiso calc U . R 1 . .
C C4 0.0271(2) 0.34721(11) 0.08980(8) 0.0270(3) Uani d . . . 1 . .
C C5 -0.1356(2) 0.34270(12) 0.04518(9) 0.0312(4) Uani d . . . 1 . .
H H5 -0.2571 0.3283 0.0669 0.037 Uiso calc U . R 1 . .
C C6 -0.1212(2) 0.35888(12) -0.02922(9) 0.0330(4) Uani d . . . 1 . .
H H6 -0.2325 0.3557 -0.0586 0.04 Uiso calc U . R 1 . .
C C7 0.0571(2) 0.38015(11) -0.06210(8) 0.0295(4) Uani d . . . 1 . .
C C8 0.2204(2) 0.38501(11) -0.01993(8) 0.0291(4) Uani d . . . 1 . .
H H8 0.3419 0.3992 -0.0418 0.035 Uiso calc U . R 1 . .
C C9 0.2015(2) 0.36867(11) 0.05497(8) 0.0262(3) Uani d . . . 1 . .
C C10 0.2299(3) 0.41845(14) -0.17348(10) 0.0442(4) Uani d . . . 1 . .
H H10A 0.27 0.4796 -0.1582 0.066 Uiso calc U . R 1 . .
H H10B 0.2045 0.4314 -0.2262 0.066 Uiso calc U . R 1 . .
H H10C 0.336 0.3603 -0.1615 0.066 Uiso calc U . R 1 . .
C C11 0.1376(2) 0.09008(11) 1.11911(8) 0.0290(4) Uani d . . . 1 . .
C C12 0.3240(2) 0.09999(11) 1.15170(8) 0.0293(3) Uani d . . . 1 . .
H H12 0.3343 0.0951 1.2031 0.035 Uiso calc U . R 1 . .
C C13 0.4829(2) 0.11602(11) 1.11055(8) 0.0275(3) Uani d . . . 1 . .
H H13 0.6045 0.1211 1.1332 0.033 Uiso calc U . R 1 . .
C C14 0.4709(2) 0.12551(10) 1.03307(8) 0.0235(3) Uani d . . . 1 . .
C C15 0.6290(2) 0.14283(11) 0.98575(8) 0.0277(3) Uani d . . . 1 . .
H H15 0.7546 0.148 1.0054 0.033 Uiso calc U . R 1 . .
C C16 0.6046(2) 0.15237(11) 0.91204(9) 0.0297(3) Uani d . . . 1 . .
H H16 0.7122 0.1653 0.8808 0.036 Uiso calc U . R 1 . .
C C17 0.4206(2) 0.14311(11) 0.88226(8) 0.0261(3) Uani d . . . 1 . .
C C18 0.2623(2) 0.12476(11) 0.92695(8) 0.0255(3) Uani d . . . 1 . .
H H18 0.138 0.1178 0.9072 0.031 Uiso calc U . R 1 . .
C C19 0.2905(2) 0.11685(10) 1.00146(8) 0.0226(3) Uani d . . . 1 . .
C C20 0.2341(3) 0.14277(16) 0.77426(9) 0.0464(5) Uani d . . . 1 . .
H H20A 0.1982 0.0747 0.7918 0.07 Uiso calc U . R 1 . .
H H20B 0.2511 0.1512 0.7213 0.07 Uiso calc U . R 1 . .
H H20C 0.1287 0.1955 0.7861 0.07 Uiso calc U . R 1 . .
C C21 0.6400(2) 0.10973(12) 0.35367(9) 0.0331(4) Uani d . . . 1 . .
C C22 0.8270(2) 0.12139(12) 0.31844(9) 0.0326(4) Uani d . . . 1 . .
H H22 0.8373 0.1208 0.2675 0.039 Uiso calc U . R 1 . .
C C23 0.9865(2) 0.13310(12) 0.35637(9) 0.0303(4) Uani d . . . 1 . .
H H23 1.1077 0.1408 0.332 0.036 Uiso calc U . R 1 . .
C C24 0.9756(2) 0.13415(10) 0.43334(8) 0.0248(3) Uani d . . . 1 . .
C C25 1.1355(2) 0.14482(11) 0.47714(9) 0.0294(4) Uani d . . . 1 . .
H H25 1.2605 0.1526 0.4557 0.035 Uiso calc U . R 1 . .
C C26 1.1130(2) 0.14410(11) 0.55054(9) 0.0297(4) Uani d . . . 1 . .
H H26 1.2222 0.1517 0.5796 0.036 Uiso calc U . R 1 . .
C C27 0.9297(2) 0.13223(11) 0.58300(8) 0.0266(3) Uani d . . . 1 . .
C C28 0.7693(2) 0.12090(11) 0.54163(8) 0.0256(3) Uani d . . . 1 . .
H H28 0.6448 0.1127 0.5633 0.031 Uiso calc U . R 1 . .
C C29 0.7961(2) 0.12195(10) 0.46737(8) 0.0239(3) Uani d . . . 1 . .
C C30 0.7473(3) 0.11325(13) 0.69340(9) 0.0394(4) Uani d . . . 1 . .
H H30A 0.6404 0.1694 0.6768 0.059 Uiso calc U . R 1 . .
H H30B 0.7685 0.1086 0.746 0.059 Uiso calc U . R 1 . .
H H30C 0.7107 0.0485 0.6831 0.059 Uiso calc U . R 1 . .
C C31 0.8739(2) 0.39253(12) 0.39623(9) 0.0310(4) Uani d . . . 1 . .
C C32 0.6918(2) 0.37727(12) 0.36380(8) 0.0307(4) Uani d . . . 1 . .
H H32 0.6865 0.3747 0.3131 0.037 Uiso calc U . R 1 . .
C C33 0.5294(2) 0.36665(11) 0.40404(8) 0.0292(3) Uani d . . . 1 . .
H H33 0.4106 0.3574 0.3813 0.035 Uiso calc U . R 1 . .
C C34 0.5327(2) 0.36906(10) 0.48069(8) 0.0247(3) Uani d . . . 1 . .
C C35 0.3695(2) 0.35936(11) 0.52671(9) 0.0293(4) Uani d . . . 1 . .
H H35 0.2464 0.3504 0.507 0.035 Uiso calc U . R 1 . .
C C36 0.3856(2) 0.36268(12) 0.59952(9) 0.0314(4) Uani d . . . 1 . .
H H36 0.2746 0.3551 0.6301 0.038 Uiso calc U . R 1 . .
C C37 0.5661(2) 0.37732(11) 0.62929(8) 0.0279(3) Uani d . . . 1 . .
C C38 0.7291(2) 0.38779(11) 0.58550(8) 0.0263(3) Uani d . . . 1 . .
H H38 0.8514 0.3978 0.6052 0.032 Uiso calc U . R 1 . .
C C39 0.7092(2) 0.38323(10) 0.51216(8) 0.0235(3) Uani d . . . 1 . .
C C40 0.7419(3) 0.39523(15) 0.73574(9) 0.0462(5) Uani d . . . 1 . .
H H40A 0.8469 0.3389 0.7297 0.069 Uiso calc U . R 1 . .
H H40B 0.7197 0.3965 0.7878 0.069 Uiso calc U . R 1 . .
H H40C 0.7817 0.4605 0.7129 0.069 Uiso calc U . R 1 . .
O O1 0.52380(18) 0.36490(11) 0.19925(7) 0.0516(4) Uani d . . . 1 . .
O O2 0.36723(15) 0.37506(8) 0.09494(6) 0.0320(3) Uani d . . . 1 . .
O O3 0.05369(17) 0.39512(9) -0.13633(6) 0.0403(3) Uani d . . . 1 . .
O O4 -0.01393(16) 0.07463(10) 1.15107(6) 0.0419(3) Uani d . . . 1 . .
O O5 0.12927(14) 0.09915(8) 1.04418(6) 0.0274(3) Uani d . . . 1 . .
O O6 0.41491(16) 0.15285(9) 0.80842(6) 0.0361(3) Uani d . . . 1 . .
O O7 0.48787(17) 0.09906(11) 0.32477(7) 0.0493(4) Uani d . . . 1 . .
O O8 0.63327(14) 0.11053(8) 0.42786(6) 0.0292(3) Uani d . . . 1 . .
O O9 0.92529(16) 0.13254(9) 0.65602(6) 0.0350(3) Uani d . . . 1 . .
O O10 1.02799(17) 0.40423(10) 0.36517(6) 0.0447(3) Uani d . . . 1 . .
O O11 0.87502(14) 0.39386(8) 0.47045(6) 0.0283(3) Uani d . . . 1 . .
O O12 0.56346(17) 0.38048(9) 0.70200(6) 0.0378(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2067(19) ?
C1 O2 . 1.3848(19) ?
C1 C2 . 1.442(2) ?
C2 C3 . 1.341(2) ?
C3 C4 . 1.433(2) ?
C4 C9 . 1.393(2) ?
C4 C5 . 1.406(2) ?
C5 C6 . 1.370(2) ?
C6 C7 . 1.401(2) ?
C7 O3 . 1.3625(19) ?
C7 C8 . 1.383(2) ?
C8 C9 . 1.382(2) ?
C9 O2 . 1.3790(18) ?
C10 O3 . 1.429(2) ?
C11 O4 . 1.2145(18) ?
C11 O5 . 1.3800(18) ?
C11 C12 . 1.446(2) ?
C12 C13 . 1.343(2) ?
C13 C14 . 1.428(2) ?
C14 C19 . 1.396(2) ?
C14 C15 . 1.407(2) ?
C15 C16 . 1.365(2) ?
C16 C17 . 1.406(2) ?
C17 O6 . 1.3584(17) ?
C17 C18 . 1.382(2) ?
C18 C19 . 1.385(2) ?
C19 O5 . 1.3763(17) ?
C20 O6 . 1.4259(19) ?
C21 O7 . 1.2102(18) ?
C21 O8 . 1.3810(18) ?
C21 C22 . 1.445(2) ?
C22 C23 . 1.343(2) ?
C23 C24 . 1.434(2) ?
C24 C29 . 1.391(2) ?
C24 C25 . 1.404(2) ?
C25 C26 . 1.370(2) ?
C26 C27 . 1.402(2) ?
C27 O9 . 1.3581(17) ?
C27 C28 . 1.383(2) ?
C28 C29 . 1.389(2) ?
C29 O8 . 1.3771(17) ?
C30 O9 . 1.4286(19) ?
C31 O10 . 1.2121(18) ?
C31 O11 . 1.3827(18) ?
C31 C32 . 1.441(2) ?
C32 C33 . 1.342(2) ?
C33 C34 . 1.431(2) ?
C34 C39 . 1.394(2) ?
C34 C35 . 1.406(2) ?
C35 C36 . 1.367(2) ?
C36 C37 . 1.406(2) ?
C37 O12 . 1.3588(18) ?
C37 C38 . 1.382(2) ?
C38 C39 . 1.383(2) ?
C39 O11 . 1.3764(17) ?
C40 O12 . 1.427(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 115.92(14) ?
O1 C1 C2 . . 126.88(16) ?
O2 C1 C2 . . 117.20(13) ?
C3 C2 C1 . . 121.24(15) ?
C2 C3 C4 . . 120.75(14) ?
C9 C4 C5 . . 117.06(14) ?
C9 C4 C3 . . 118.19(14) ?
C5 C4 C3 . . 124.74(13) ?
C6 C5 C4 . . 120.88(14) ?
C5 C6 C7 . . 120.25(14) ?
O3 C7 C8 . . 124.49(14) ?
O3 C7 C6 . . 115.04(13) ?
C8 C7 C6 . . 120.47(14) ?
C9 C8 C7 . . 118.05(14) ?
O2 C9 C8 . . 116.18(13) ?
O2 C9 C4 . . 120.54(14) ?
C8 C9 C4 . . 123.28(14) ?
O4 C11 O5 . . 116.16(14) ?
O4 C11 C12 . . 126.55(14) ?
O5 C11 C12 . . 117.29(13) ?
C13 C12 C11 . . 121.14(14) ?
C12 C13 C14 . . 120.67(14) ?
C19 C14 C15 . . 117.17(13) ?
C19 C14 C13 . . 118.26(13) ?
C15 C14 C13 . . 124.57(13) ?
C16 C15 C14 . . 120.96(13) ?
C15 C16 C17 . . 120.19(14) ?
O6 C17 C18 . . 124.51(13) ?
O6 C17 C16 . . 114.86(13) ?
C18 C17 C16 . . 120.63(14) ?
C17 C18 C19 . . 117.95(13) ?
O5 C19 C18 . . 116.30(12) ?
O5 C19 C14 . . 120.61(13) ?
C18 C19 C14 . . 123.08(13) ?
O7 C21 O8 . . 116.32(14) ?
O7 C21 C22 . . 126.58(15) ?
O8 C21 C22 . . 117.10(13) ?
C23 C22 C21 . . 121.23(14) ?
C22 C23 C24 . . 120.66(14) ?
C29 C24 C25 . . 117.58(14) ?
C29 C24 C23 . . 118.09(13) ?
C25 C24 C23 . . 124.32(13) ?
C26 C25 C24 . . 120.65(14) ?
C25 C26 C27 . . 120.27(14) ?
O9 C27 C28 . . 124.35(13) ?
O9 C27 C26 . . 115.00(13) ?
C28 C27 C26 . . 120.65(14) ?
C27 C28 C29 . . 117.91(13) ?
O8 C29 C28 . . 116.34(12) ?
O8 C29 C24 . . 120.72(13) ?
C28 C29 C24 . . 122.94(13) ?
O10 C31 O11 . . 116.07(14) ?
O10 C31 C32 . . 126.71(15) ?
O11 C31 C32 . . 117.23(13) ?
C33 C32 C31 . . 121.10(14) ?
C32 C33 C34 . . 120.91(14) ?
C39 C34 C35 . . 117.36(14) ?
C39 C34 C33 . . 118.00(14) ?
C35 C34 C33 . . 124.63(13) ?
C36 C35 C34 . . 120.79(14) ?
C35 C36 C37 . . 120.22(14) ?
O12 C37 C38 . . 124.68(14) ?
O12 C37 C36 . . 114.87(13) ?
C38 C37 C36 . . 120.45(14) ?
C37 C38 C39 . . 118.17(13) ?
O11 C39 C38 . . 116.35(12) ?
O11 C39 C34 . . 120.65(13) ?
C38 C39 C34 . . 123.00(14) ?
C9 O2 C1 . . 122.04(12) ?
C7 O3 C10 . . 118.01(13) ?
C19 O5 C11 . . 122.02(11) ?
C17 O6 C20 . . 118.13(12) ?
C29 O8 C21 . . 122.19(11) ?
C27 O9 C30 . . 117.88(12) ?
C39 O11 C31 . . 122.10(11) ?
C37 O12 C40 . . 117.77(13) ?



####################################################################### 
# 
# 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_uch121_7MeO_rt_400nm_010min
_database_code_depnum_ccdc_archive 'CCDC 2075129'
loop_
_audit_author_name
_audit_author_address
'Kingo Uchida'
;Ryukoku University
Japan
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        7-methoxycoumarin
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         176.16

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8504(8)
_cell_length_b                   10.7265(13)
_cell_length_c                   12.3293(15)
_cell_angle_alpha                107.962(4)
_cell_angle_beta                 95.521(4)
_cell_angle_gamma                95.436(4)
_cell_volume                     850.38(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    212
_cell_measurement_theta_min      3.2724
_cell_measurement_theta_max      22.3220
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
 The crystal was prepared by recrystallization from benzene. 
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            43778
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3003
_reflns_number_gt                1797
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.2183
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_number_reflns         3003
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+0.2942P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1354(6) 0.2215(4) 1.0327(3) 0.0924(11) Uani d . . . 1 . .
C C2 0.3190(6) 0.1713(4) 1.0523(3) 0.0950(11) Uani d . . . 1 . .
H H2 0.3278 0.1182 1.0993 0.114 Uiso calc U . R 1 . .
C C3 0.4772(5) 0.1999(4) 1.0039(3) 0.0861(10) Uani d . . . 1 . .
H H3 0.5939 0.166 1.0172 0.103 Uiso calc U . R 1 . .
C C4 0.4686(4) 0.2813(3) 0.9324(2) 0.0673(8) Uani d . . . 1 . .
C C5 0.6269(4) 0.3171(3) 0.8800(3) 0.0758(9) Uani d . . . 1 . .
H H5 0.7464 0.2847 0.8897 0.091 Uiso calc U . R 1 . .
C C6 0.6093(5) 0.3987(3) 0.8150(3) 0.0759(9) Uani d . . . 1 . .
H H6 0.716 0.4213 0.7804 0.091 Uiso calc U . R 1 . .
C C7 0.4324(5) 0.4479(3) 0.8006(3) 0.0703(8) Uani d . . . 1 . .
C C8 0.2729(4) 0.4152(3) 0.8512(3) 0.0686(8) Uani d . . . 1 . .
H H8 0.1539 0.4482 0.8418 0.082 Uiso calc U . R 1 . .
C C9 0.2948(4) 0.3327(3) 0.9157(2) 0.0616(7) Uani d . . . 1 . .
C C10 0.2576(7) 0.5859(4) 0.7163(4) 0.1119(14) Uani d . . . 1 . .
H H10A 0.1498 0.5178 0.6776 0.168 Uiso calc U . R 1 . .
H H10B 0.2805 0.6425 0.6705 0.168 Uiso calc U . R 1 . .
H H10C 0.2253 0.6369 0.7896 0.168 Uiso calc U . R 1 . .
C C11 0.3653(5) -0.0145(3) 0.7111(3) 0.0758(9) Uani d . . . 1 . .
C C12 0.1812(5) -0.0329(3) 0.7565(3) 0.0747(9) Uani d . . . 1 . .
H H12 0.1726 -0.0834 0.8056 0.09 Uiso calc U . R 1 . .
C C13 0.0249(5) 0.0207(3) 0.7296(3) 0.0700(8) Uani d . . . 1 . .
H H13 -0.0923 0.0058 0.7587 0.084 Uiso calc U . R 1 . .
C C14 0.0337(4) 0.1006(3) 0.6569(2) 0.0579(7) Uani d . . . 1 . .
C C15 -0.1234(4) 0.1621(3) 0.6244(3) 0.0686(8) Uani d . . . 1 . .
H H15 -0.2439 0.1514 0.6515 0.082 Uiso calc U . R 1 . .
C C16 -0.1031(5) 0.2367(3) 0.5545(3) 0.0735(9) Uani d . . . 1 . .
H H16 -0.2093 0.2764 0.5339 0.088 Uiso calc U . R 1 . .
C C17 0.0764(5) 0.2543(3) 0.5129(3) 0.0667(8) Uani d . . . 1 . .
C C18 0.2336(4) 0.1943(3) 0.5424(2) 0.0615(7) Uani d . . . 1 . .
H H18 0.3533 0.2042 0.5143 0.074 Uiso calc U . R 1 . .
C C19 0.2099(4) 0.1201(3) 0.6139(2) 0.0548(7) Uani d . . . 1 . .
C C20 0.2567(6) 0.3512(4) 0.3962(4) 0.1144(14) Uani d . . . 1 . .
H H20A 0.3637 0.3892 0.4574 0.172 Uiso calc U . R 1 . .
H H20B 0.2399 0.4104 0.3523 0.172 Uiso calc U . R 1 . .
H H20C 0.2859 0.2684 0.347 0.172 Uiso calc U . R 1 . .
O O1 -0.0167(4) 0.2016(4) 1.0702(3) 0.1294(12) Uani d . . . 1 . .
O O2 0.1317(3) 0.3031(2) 0.96520(18) 0.0780(7) Uani d . . . 1 . .
O O3 0.4309(4) 0.5274(2) 0.7329(2) 0.0998(8) Uani d . . . 1 . .
O O4 0.5155(4) -0.0600(3) 0.7288(2) 0.1079(9) Uani d . . . 1 . .
O O5 0.3711(3) 0.0620(2) 0.64091(17) 0.0676(6) Uani d . . . 1 . .
O O6 0.0797(4) 0.3300(2) 0.4431(2) 0.0920(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.208(4) ?
C1 O2 . 1.382(4) ?
C1 C2 . 1.442(5) ?
C2 C3 . 1.342(5) ?
C3 C4 . 1.420(5) ?
C4 C9 . 1.382(4) ?
C4 C5 . 1.396(4) ?
C5 C6 . 1.362(5) ?
C6 C7 . 1.384(4) ?
C7 O3 . 1.366(4) ?
C7 C8 . 1.378(4) ?
C8 C9 . 1.370(4) ?
C9 O2 . 1.380(3) ?
C10 O3 . 1.420(4) ?
C11 O4 . 1.209(4) ?
C11 O5 . 1.365(4) ?
C11 C12 . 1.449(5) ?
C12 C13 . 1.324(4) ?
C13 C14 . 1.419(4) ?
C14 C19 . 1.387(4) ?
C14 C15 . 1.403(4) ?
C15 C16 . 1.353(4) ?
C16 C17 . 1.395(4) ?
C17 O6 . 1.354(4) ?
C17 C18 . 1.380(4) ?
C18 C19 . 1.368(4) ?
C19 O5 . 1.381(3) ?
C20 O6 . 1.421(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 115.6(3) ?
O1 C1 C2 . . 127.1(4) ?
O2 C1 C2 . . 117.3(3) ?
C3 C2 C1 . . 121.0(4) ?
C2 C3 C4 . . 120.8(3) ?
C9 C4 C5 . . 117.1(3) ?
C9 C4 C3 . . 118.5(3) ?
C5 C4 C3 . . 124.4(3) ?
C6 C5 C4 . . 121.1(3) ?
C5 C6 C7 . . 119.9(3) ?
O3 C7 C8 . . 124.3(3) ?
O3 C7 C6 . . 114.9(3) ?
C8 C7 C6 . . 120.8(3) ?
C9 C8 C7 . . 118.0(3) ?
C8 C9 O2 . . 116.1(3) ?
C8 C9 C4 . . 123.1(3) ?
O2 C9 C4 . . 120.8(3) ?
O4 C11 O5 . . 116.2(3) ?
O4 C11 C12 . . 126.8(3) ?
O5 C11 C12 . . 117.1(3) ?
C13 C12 C11 . . 121.3(3) ?
C12 C13 C14 . . 120.9(3) ?
C19 C14 C15 . . 116.8(3) ?
C19 C14 C13 . . 118.3(3) ?
C15 C14 C13 . . 125.0(3) ?
C16 C15 C14 . . 121.3(3) ?
C15 C16 C17 . . 120.4(3) ?
O6 C17 C18 . . 124.8(3) ?
O6 C17 C16 . . 115.4(3) ?
C18 C17 C16 . . 119.8(3) ?
C19 C18 C17 . . 118.7(3) ?
C18 C19 O5 . . 116.6(2) ?
C18 C19 C14 . . 123.0(3) ?
O5 C19 C14 . . 120.4(2) ?
C9 O2 C1 . . 121.6(3) ?
C7 O3 C10 . . 118.8(3) ?
C11 O5 C19 . . 122.0(2) ?
C17 O6 C20 . . 118.7(3) ?



_chemical_properties_physical    Photo-sensitive
####################################################################### 
# 
# 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_uch117_7MeO_rt
_database_code_depnum_ccdc_archive 'CCDC 2074689'
loop_
_audit_author_name
_audit_author_address
'Kanae Yano' 'The Cambridge Crystal Date Center'
_audit_update_record             
;
2021-04-01 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         176.16

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8137(3)
_cell_length_b                   10.6684(5)
_cell_length_c                   12.4313(6)
_cell_angle_alpha                108.1891(15)
_cell_angle_beta                 95.2297(15)
_cell_angle_gamma                95.2045(15)
_cell_volume                     848.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    264
_cell_measurement_theta_min      3.2726
_cell_measurement_theta_max      25.0760
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
 The crystal was prepared by recrystallization from benzene. 
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            44444
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3053
_reflns_number_gt                2094
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1625
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_number_reflns         3053
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.1707P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.536
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1406(4) 0.2207(3) 1.0334(2) 0.0750(7) Uani d . . . 1 . .
C C2 0.3241(4) 0.1704(3) 1.0519(2) 0.0771(7) Uani d . . . 1 . .
H H2 0.3333 0.117 1.0982 0.092 Uiso calc U . R 1 . .
C C3 0.4827(3) 0.1991(3) 1.00360(19) 0.0701(6) Uani d . . . 1 . .
H H3 0.5999 0.1645 1.0162 0.084 Uiso calc U . R 1 . .
C C4 0.4744(3) 0.2819(2) 0.93321(16) 0.0546(5) Uani d . . . 1 . .
C C5 0.6331(3) 0.3183(2) 0.88028(19) 0.0656(6) Uani d . . . 1 . .
H H5 0.7542 0.2867 0.8897 0.079 Uiso calc U . R 1 . .
C C6 0.6125(3) 0.3990(2) 0.8153(2) 0.0666(6) Uani d . . . 1 . .
H H6 0.7191 0.4221 0.7806 0.08 Uiso calc U . R 1 . .
C C7 0.4325(3) 0.4473(2) 0.80039(18) 0.0598(5) Uani d . . . 1 . .
C C8 0.2740(3) 0.4140(2) 0.85129(17) 0.0574(5) Uani d . . . 1 . .
H H8 0.1533 0.446 0.8418 0.069 Uiso calc U . R 1 . .
C C9 0.2982(3) 0.3323(2) 0.91664(16) 0.0521(5) Uani d . . . 1 . .
C C10 0.2532(4) 0.5848(3) 0.7182(3) 0.0938(9) Uani d . . . 1 . .
H H10A 0.1468 0.5159 0.6783 0.141 Uiso calc U . R 1 . .
H H10B 0.2753 0.6437 0.6746 0.141 Uiso calc U . R 1 . .
H H10C 0.2187 0.6339 0.7914 0.141 Uiso calc U . R 1 . .
C C11 0.3616(3) -0.0146(2) 0.71184(18) 0.0612(6) Uani d . . . 1 . .
C C12 0.1783(3) -0.0326(2) 0.75582(18) 0.0614(6) Uani d . . . 1 . .
H H12 0.1689 -0.0834 0.8042 0.074 Uiso calc U . R 1 . .
C C13 0.0201(3) 0.0220(2) 0.72882(17) 0.0570(5) Uani d . . . 1 . .
H H13 -0.0979 0.0077 0.7579 0.068 Uiso calc U . R 1 . .
C C14 0.0298(3) 0.10189(18) 0.65599(15) 0.0466(5) Uani d . . . 1 . .
C C15 -0.1278(3) 0.1628(2) 0.62273(18) 0.0574(5) Uani d . . . 1 . .
H H15 -0.2499 0.1518 0.6487 0.069 Uiso calc U . R 1 . .
C C16 -0.1051(3) 0.2380(2) 0.55302(19) 0.0617(6) Uani d . . . 1 . .
H H16 -0.2109 0.2786 0.5325 0.074 Uiso calc U . R 1 . .
C C17 0.0767(3) 0.25418(19) 0.51235(17) 0.0555(5) Uani d . . . 1 . .
C C18 0.2338(3) 0.19491(19) 0.54205(16) 0.0515(5) Uani d . . . 1 . .
H H18 0.3547 0.2047 0.5145 0.062 Uiso calc U . R 1 . .
C C19 0.2081(3) 0.12032(18) 0.61390(15) 0.0444(4) Uani d . . . 1 . .
C C20 0.2595(4) 0.3500(3) 0.3961(3) 0.0979(9) Uani d . . . 1 . .
H H20A 0.3655 0.3913 0.4569 0.147 Uiso calc U . R 1 . .
H H20B 0.2421 0.4062 0.3498 0.147 Uiso calc U . R 1 . .
H H20C 0.2915 0.2657 0.3501 0.147 Uiso calc U . R 1 . .
O O1 -0.0113(3) 0.2001(2) 1.07177(19) 0.1114(8) Uani d . . . 1 . .
O O2 0.1352(2) 0.30149(16) 0.96611(13) 0.0658(4) Uani d . . . 1 . .
O O3 0.4294(3) 0.52677(16) 0.73335(16) 0.0834(5) Uani d . . . 1 . .
O O4 0.5130(3) -0.0600(2) 0.73005(16) 0.0905(6) Uani d . . . 1 . .
O O5 0.36962(18) 0.06296(14) 0.64172(11) 0.0559(4) Uani d . . . 1 . .
O O6 0.0807(3) 0.33051(16) 0.44295(15) 0.0779(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.209(3) ?
C1 O2 . 1.376(3) ?
C1 C2 . 1.432(3) ?
C2 C3 . 1.340(3) ?
C3 C4 . 1.425(3) ?
C4 C9 . 1.384(3) ?
C4 C5 . 1.402(3) ?
C5 C6 . 1.361(3) ?
C6 C7 . 1.392(3) ?
C7 O3 . 1.362(3) ?
C7 C8 . 1.374(3) ?
C8 C9 . 1.375(3) ?
C9 O2 . 1.380(2) ?
C10 O3 . 1.423(3) ?
C11 O4 . 1.211(3) ?
C11 O5 . 1.378(2) ?
C11 C12 . 1.430(3) ?
C12 C13 . 1.336(3) ?
C13 C14 . 1.426(3) ?
C14 C19 . 1.387(2) ?
C14 C15 . 1.400(3) ?
C15 C16 . 1.362(3) ?
C16 C17 . 1.397(3) ?
C17 O6 . 1.359(2) ?
C17 C18 . 1.370(3) ?
C18 C19 . 1.381(3) ?
C19 O5 . 1.375(2) ?
C20 O6 . 1.423(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 116.1(2) ?
O1 C1 C2 . . 126.4(3) ?
O2 C1 C2 . . 117.4(2) ?
C3 C2 C1 . . 121.0(2) ?
C2 C3 C4 . . 120.9(2) ?
C9 C4 C5 . . 117.0(2) ?
C9 C4 C3 . . 118.12(19) ?
C5 C4 C3 . . 124.9(2) ?
C6 C5 C4 . . 120.9(2) ?
C5 C6 C7 . . 120.3(2) ?
O3 C7 C8 . . 124.6(2) ?
O3 C7 C6 . . 115.0(2) ?
C8 C7 C6 . . 120.3(2) ?
C7 C8 C9 . . 118.38(19) ?
C8 C9 O2 . . 116.40(18) ?
C8 C9 C4 . . 123.06(19) ?
O2 C9 C4 . . 120.53(19) ?
O4 C11 O5 . . 115.8(2) ?
O4 C11 C12 . . 126.9(2) ?
O5 C11 C12 . . 117.33(19) ?
C13 C12 C11 . . 121.4(2) ?
C12 C13 C14 . . 120.82(18) ?
C19 C14 C15 . . 117.16(18) ?
C19 C14 C13 . . 117.89(18) ?
C15 C14 C13 . . 124.95(18) ?
C16 C15 C14 . . 121.04(18) ?
C15 C16 C17 . . 120.10(19) ?
O6 C17 C18 . . 124.82(19) ?
O6 C17 C16 . . 114.65(19) ?
C18 C17 C16 . . 120.53(19) ?
C17 C18 C19 . . 118.39(18) ?
O5 C19 C18 . . 116.44(16) ?
O5 C19 C14 . . 120.78(17) ?
C18 C19 C14 . . 122.78(17) ?
C1 O2 C9 . . 121.94(17) ?
C7 O3 C10 . . 118.4(2) ?
C19 O5 C11 . . 121.79(15) ?
C17 O6 C20 . . 118.23(19) ?



####################################################################### 
# 
# 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_uch106_coumarin_benzene_143K
_database_code_depnum_ccdc_archive 'CCDC 2061358'
loop_
_audit_author_name
_audit_author_address
'Kanae Yano'
;Ryukoku University
Japan
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         352.33

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.6312(7)
_cell_length_b                   12.0469(6)
_cell_length_c                   18.6651(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3289.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1270
_cell_measurement_theta_min      2.4387
_cell_measurement_theta_max      30.2829
_cell_measurement_temperature    143.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.509
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.202
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472

_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      143.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            178897
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             2922
_reflns_number_gt                2693
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1368
_refine_ls_goodness_of_fit_ref   1.305
_refine_ls_restrained_S_all      1.305
_refine_ls_number_reflns         2922
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+0.8903P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.441
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.78884(10) 0.13081(13) 0.53733(8) 0.0232(4) Uani d . . . 1 . .
C C2 0.82394(11) 0.24658(12) 0.54102(8) 0.0224(3) Uani d . . . 1 . .
H H2 0.8131 0.2778 0.5899 0.027 Uiso calc U . R 1 . .
C C3 0.92300(10) 0.27257(12) 0.51661(8) 0.0216(3) Uani d . . . 1 . .
H H3 0.9653 0.2876 0.5576 0.026 Uiso calc U . R 1 . .
C C4 0.95868(10) 0.18576(12) 0.46609(8) 0.0212(3) Uani d . . . 1 . .
C C5 1.03988(10) 0.19845(13) 0.42771(8) 0.0237(3) Uani d . . . 1 . .
H H5 1.0733 0.2656 0.4327 0.028 Uiso calc U . R 1 . .
C C6 1.07348(11) 0.11656(14) 0.38259(9) 0.0270(4) Uani d . . . 1 . .
H H6 1.1291 0.1276 0.3573 0.032 Uiso calc U . R 1 . .
C C7 1.02468(11) 0.01803(13) 0.37485(9) 0.0274(4) Uani d . . . 1 . .
C C8 0.94362(11) 0.00285(13) 0.41187(8) 0.0260(4) Uani d . . . 1 . .
H H8 0.9097 -0.0639 0.4064 0.031 Uiso calc U . R 1 . .
C C9 0.91269(10) 0.08558(12) 0.45667(8) 0.0218(3) Uani d . . . 1 . .
C C10 1.12397(13) -0.05144(17) 0.28354(11) 0.0408(5) Uani d . . . 1 . .
H H10A 1.1112 0.0159 0.2559 0.061 Uiso calc U . R 1 . .
H H10B 1.1285 -0.115 0.251 0.061 Uiso calc U . R 1 . .
H H10C 1.1818 -0.0425 0.3094 0.061 Uiso calc U . R 1 . .
C C11 0.92410(11) 0.41771(12) 0.41200(8) 0.0230(3) Uani d . . . 1 . .
C C12 0.88410(10) 0.38157(12) 0.48157(8) 0.0224(3) Uani d . . . 1 . .
H H12 0.8872 0.4439 0.5169 0.027 Uiso calc U . R 1 . .
C C13 0.78722(10) 0.32976(12) 0.48252(8) 0.0215(3) Uani d . . . 1 . .
H H13 0.7394 0.3815 0.5012 0.026 Uiso calc U . R 1 . .
C C14 0.76294(10) 0.27977(12) 0.41128(8) 0.0199(3) Uani d . . . 1 . .
C C15 0.68673(10) 0.21214(13) 0.40155(8) 0.0228(3) Uani d . . . 1 . .
H H15 0.6481 0.1979 0.4414 0.027 Uiso calc U . R 1 . .
C C16 0.66503(10) 0.16477(13) 0.33596(8) 0.0241(3) Uani d . . . 1 . .
H H16 0.6124 0.1192 0.3311 0.029 Uiso calc U . R 1 . .
C C17 0.72148(10) 0.18496(12) 0.27748(8) 0.0226(3) Uani d . . . 1 . .
C C18 0.79709(11) 0.25387(13) 0.28474(8) 0.0235(4) Uani d . . . 1 . .
H H18 0.8353 0.2689 0.2448 0.028 Uiso calc U . R 1 . .
C C19 0.81591(10) 0.30016(12) 0.35079(8) 0.0208(3) Uani d . . . 1 . .
C C20 0.63097(12) 0.07142(15) 0.20004(9) 0.0352(4) Uani d . . . 1 . .
H H20A 0.6324 0.0112 0.2353 0.053 Uiso calc U . R 1 . .
H H20B 0.6329 0.04 0.1516 0.053 Uiso calc U . R 1 . .
H H20C 0.5746 0.1145 0.206 0.053 Uiso calc U . R 1 . .
O O1 0.83204(7) 0.05817(9) 0.49336(6) 0.0258(3) Uani d . . . 1 . .
O O2 0.72255(8) 0.09797(10) 0.56890(6) 0.0319(3) Uani d . . . 1 . .
O O3 1.05155(9) -0.07002(10) 0.33372(8) 0.0396(3) Uani d . . . 1 . .
O O4 0.89107(7) 0.37178(9) 0.35068(6) 0.0258(3) Uani d . . . 1 . .
O O5 0.98443(8) 0.48449(10) 0.40594(6) 0.0327(3) Uani d . . . 1 . .
O O6 0.70810(8) 0.14222(10) 0.21050(6) 0.0294(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.2019(19) ?
C1 O1 . 1.3561(19) ?
C1 C2 . 1.488(2) ?
C2 C3 . 1.551(2) ?
C2 C13 . 1.576(2) ?
C3 C4 . 1.502(2) ?
C3 C12 . 1.573(2) ?
C4 C9 . 1.393(2) ?
C4 C5 . 1.396(2) ?
C5 C6 . 1.387(2) ?
C6 C7 . 1.393(2) ?
C7 O3 . 1.367(2) ?
C7 C8 . 1.385(2) ?
C8 C9 . 1.377(2) ?
C9 O1 . 1.4036(19) ?
C10 O3 . 1.432(2) ?
C11 O5 . 1.1997(19) ?
C11 O4 . 1.3601(19) ?
C11 C12 . 1.489(2) ?
C12 C13 . 1.549(2) ?
C13 C14 . 1.502(2) ?
C14 C19 . 1.391(2) ?
C14 C15 . 1.393(2) ?
C15 C16 . 1.388(2) ?
C16 C17 . 1.390(2) ?
C17 O6 . 1.3663(18) ?
C17 C18 . 1.390(2) ?
C18 C19 . 1.381(2) ?
C19 O4 . 1.3978(18) ?
C20 O6 . 1.428(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 117.42(14) ?
O2 C1 C2 . . 124.36(15) ?
O1 C1 C2 . . 118.17(13) ?
C1 C2 C3 . . 119.87(13) ?
C1 C2 C13 . . 116.49(12) ?
C3 C2 C13 . . 89.24(11) ?
C4 C3 C2 . . 111.63(12) ?
C4 C3 C12 . . 116.48(12) ?
C2 C3 C12 . . 87.28(11) ?
C9 C4 C5 . . 116.19(14) ?
C9 C4 C3 . . 120.98(13) ?
C5 C4 C3 . . 122.81(13) ?
C6 C5 C4 . . 122.38(14) ?
C5 C6 C7 . . 119.16(15) ?
O3 C7 C8 . . 115.09(14) ?
O3 C7 C6 . . 124.89(15) ?
C8 C7 C6 . . 120.00(15) ?
C9 C8 C7 . . 119.26(15) ?
C8 C9 C4 . . 123.01(14) ?
C8 C9 O1 . . 113.71(13) ?
C4 C9 O1 . . 123.25(14) ?
O5 C11 O4 . . 117.06(14) ?
O5 C11 C12 . . 124.56(14) ?
O4 C11 C12 . . 118.37(13) ?
C11 C12 C13 . . 119.17(13) ?
C11 C12 C3 . . 117.66(13) ?
C13 C12 C3 . . 89.43(11) ?
C14 C13 C12 . . 111.58(12) ?
C14 C13 C2 . . 116.03(12) ?
C12 C13 C2 . . 87.26(11) ?
C19 C14 C15 . . 116.32(13) ?
C19 C14 C13 . . 121.05(13) ?
C15 C14 C13 . . 122.62(13) ?
C16 C15 C14 . . 122.60(14) ?
C15 C16 C17 . . 119.01(14) ?
O6 C17 C18 . . 115.36(13) ?
O6 C17 C16 . . 124.58(14) ?
C18 C17 C16 . . 120.06(14) ?
C19 C18 C17 . . 119.14(14) ?
C18 C19 C14 . . 122.83(14) ?
C18 C19 O4 . . 113.88(13) ?
C14 C19 O4 . . 123.26(13) ?
C1 O1 C9 . . 122.36(12) ?
C7 O3 C10 . . 117.32(14) ?
C11 O4 C19 . . 121.96(12) ?
C17 O6 C20 . . 117.60(12) ?



