# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_3
_audit_block_doi                 10.5517/ccdc.csd.cc294tjt
_database_code_depnum_ccdc_archive 'CCDC 2119796'
loop_
_audit_author_name
_audit_author_address
'DPP-modified coumarin'
;Peking University
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 O2 P'
_chemical_formula_weight         330.30

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0126(2)
_cell_length_b                   14.6954(3)
_cell_length_c                   19.5545(5)
_cell_angle_alpha                91.632(2)
_cell_angle_beta                 97.805(2)
_cell_angle_gamma                105.419(2)
_cell_volume                     2467.86(10)
_cell_formula_units_Z            6
_cell_measurement_temperature    179.99(10)
_cell_measurement_reflns_used    11682
_cell_measurement_theta_min      2.4170
_cell_measurement_theta_max      29.3910

_exptl_crystal_description       rod-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.55784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      179.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34864
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         29.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12366
_reflns_number_gt                9107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.5776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12366
_refine_ls_number_parameters     649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.29558(5) 0.74349(3) 0.97150(2) 0.03279(11) Uani 1 1 d . . . . .
O1 O 0.40544(15) 0.44091(9) 0.87420(7) 0.0453(3) Uani 1 1 d . . . . .
O2 O 0.15930(14) 0.43412(8) 0.87727(6) 0.0368(3) Uani 1 1 d . . . . .
C1 C 0.5072(2) 0.78232(11) 0.97837(8) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.5870(2) 0.84974(14) 0.93855(10) 0.0442(5) Uani 1 1 d . . . . .
H2 H 0.5320 0.8741 0.9033 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7478(2) 0.88113(16) 0.95079(11) 0.0573(6) Uani 1 1 d . . . . .
H3 H 0.7998 0.9269 0.9240 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8314(2) 0.84527(16) 1.00208(11) 0.0539(5) Uani 1 1 d . . . . .
H4 H 0.9395 0.8665 1.0099 0.065 Uiso 1 1 calc R U . . .
C5 C 0.7545(2) 0.77765(15) 1.04194(11) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.8108 0.7523 1.0761 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5942(2) 0.74757(13) 1.03117(9) 0.0423(4) Uani 1 1 d . . . . .
H6 H 0.5430 0.7036 1.0593 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2253(2) 0.80454(12) 0.89881(10) 0.0402(4) Uani 1 1 d . . . . .
C8 C 0.1977(3) 0.89142(14) 0.91417(14) 0.0598(6) Uani 1 1 d . . . . .
H8 H 0.2208 0.9176 0.9595 0.072 Uiso 1 1 calc R U . . .
C9 C 0.1362(3) 0.93861(19) 0.8623(2) 0.0844(10) Uani 1 1 d . . . . .
H9 H 0.1189 0.9967 0.8728 0.101 Uiso 1 1 calc R U . . .
C10 C 0.1006(3) 0.9005(2) 0.7959(2) 0.0864(11) Uani 1 1 d . . . . .
H10 H 0.0573 0.9323 0.7615 0.104 Uiso 1 1 calc R U . . .
C11 C 0.1280(3) 0.8157(2) 0.77917(14) 0.0709(8) Uani 1 1 d . . . . .
H11 H 0.1041 0.7903 0.7336 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1919(2) 0.76792(16) 0.83077(11) 0.0510(5) Uani 1 1 d . . . . .
H12 H 0.2122 0.7110 0.8194 0.061 Uiso 1 1 calc R U . . .
C13 C 0.24601(18) 0.62252(11) 0.93220(8) 0.0265(3) Uani 1 1 d . . . . .
C14 C 0.3535(2) 0.58010(11) 0.91587(8) 0.0308(4) Uani 1 1 d . . . . .
H14 H 0.4575 0.6149 0.9225 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3135(2) 0.48280(12) 0.88857(9) 0.0329(4) Uani 1 1 d . . . . .
C16 C 0.04595(19) 0.47496(12) 0.89328(8) 0.0318(4) Uani 1 1 d . . . . .
C17 C 0.08367(19) 0.56782(11) 0.92176(8) 0.0285(3) Uani 1 1 d . . . . .
C18 C -0.0392(2) 0.60190(13) 0.93817(9) 0.0365(4) Uani 1 1 d . . . . .
H18 H -0.0184 0.6633 0.9576 0.044 Uiso 1 1 calc R U . . .
C19 C -0.1904(2) 0.54563(15) 0.92586(9) 0.0443(5) Uani 1 1 d . . . . .
H19 H -0.2706 0.5689 0.9376 0.053 Uiso 1 1 calc R U . . .
C20 C -0.2234(2) 0.45417(16) 0.89598(10) 0.0462(5) Uani 1 1 d . . . . .
H20 H -0.3259 0.4170 0.8869 0.055 Uiso 1 1 calc R U . . .
C21 C -0.1055(2) 0.41839(14) 0.87984(9) 0.0415(4) Uani 1 1 d . . . . .
H21 H -0.1272 0.3570 0.8602 0.050 Uiso 1 1 calc R U . . .
P2 P 0.16185(5) 0.38834(3) 0.65775(2) 0.02674(10) Uani 1 1 d . . . . .
O3 O -0.14932(14) 0.35895(10) 0.41098(6) 0.0472(3) Uani 1 1 d . . . . .
O4 O 0.09745(12) 0.36259(8) 0.41731(5) 0.0306(2) Uani 1 1 d . . . . .
C22 C -0.03105(19) 0.38452(11) 0.67856(8) 0.0290(3) Uani 1 1 d . . . . .
C23 C -0.0605(2) 0.47162(13) 0.69088(9) 0.0384(4) Uani 1 1 d . . . . .
H23 H 0.0153 0.5272 0.6865 0.046 Uiso 1 1 calc R U . . .
C24 C -0.2007(2) 0.47619(15) 0.70950(9) 0.0478(5) Uani 1 1 d . . . . .
H24 H -0.2195 0.5346 0.7170 0.057 Uiso 1 1 calc R U . . .
C25 C -0.3130(2) 0.39416(16) 0.71701(9) 0.0462(5) Uani 1 1 d . . . . .
H25 H -0.4070 0.3973 0.7301 0.055 Uiso 1 1 calc R U . . .
C26 C -0.2860(2) 0.30743(15) 0.70509(9) 0.0452(5) Uani 1 1 d . . . . .
H26 H -0.3618 0.2522 0.7103 0.054 Uiso 1 1 calc R U . . .
C27 C -0.1461(2) 0.30237(13) 0.68537(9) 0.0378(4) Uani 1 1 d . . . . .
H27 H -0.1293 0.2437 0.6766 0.045 Uiso 1 1 calc R U . . .
C28 C 0.18542(18) 0.27106(11) 0.67605(8) 0.0262(3) Uani 1 1 d . . . . .
C29 C 0.2651(2) 0.26218(12) 0.74092(8) 0.0333(4) Uani 1 1 d . . . . .
H29 H 0.2977 0.3136 0.7735 0.040 Uiso 1 1 calc R U . . .
C30 C 0.2958(2) 0.17716(14) 0.75690(9) 0.0419(4) Uani 1 1 d . . . . .
H30 H 0.3484 0.1715 0.8002 0.050 Uiso 1 1 calc R U . . .
C31 C 0.2487(2) 0.10093(13) 0.70884(10) 0.0400(4) Uani 1 1 d . . . . .
H31 H 0.2713 0.0443 0.7195 0.048 Uiso 1 1 calc R U . . .
C32 C 0.1682(2) 0.10819(12) 0.64495(9) 0.0374(4) Uani 1 1 d . . . . .
H32 H 0.1354 0.0563 0.6129 0.045 Uiso 1 1 calc R U . . .
C33 C 0.1361(2) 0.19277(11) 0.62859(9) 0.0323(4) Uani 1 1 d . . . . .
H33 H 0.0812 0.1973 0.5855 0.039 Uiso 1 1 calc R U . . .
C34 C 0.13024(18) 0.37666(10) 0.56252(8) 0.0247(3) Uani 1 1 d . . . . .
C35 C -0.00705(18) 0.37186(11) 0.52345(8) 0.0308(4) Uani 1 1 d . . . . .
H35 H -0.0916 0.3735 0.5455 0.037 Uiso 1 1 calc R U . . .
C36 C -0.02867(19) 0.36432(12) 0.44856(9) 0.0327(4) Uani 1 1 d . . . . .
C37 C 0.24054(18) 0.36921(10) 0.45561(8) 0.0254(3) Uani 1 1 d . . . . .
C38 C 0.26341(17) 0.37751(10) 0.52761(8) 0.0239(3) Uani 1 1 d . . . . .
C39 C 0.41373(18) 0.38634(11) 0.56180(9) 0.0289(3) Uani 1 1 d . . . . .
H39 H 0.4326 0.3917 0.6099 0.035 Uiso 1 1 calc R U . . .
C40 C 0.53430(19) 0.38719(11) 0.52520(9) 0.0324(4) Uani 1 1 d . . . . .
H40 H 0.6338 0.3936 0.5487 0.039 Uiso 1 1 calc R U . . .
C41 C 0.5082(2) 0.37848(11) 0.45357(9) 0.0328(4) Uani 1 1 d . . . . .
H41 H 0.5901 0.3789 0.4292 0.039 Uiso 1 1 calc R U . . .
C42 C 0.36052(19) 0.36907(11) 0.41819(9) 0.0305(4) Uani 1 1 d . . . . .
H42 H 0.3421 0.3628 0.3701 0.037 Uiso 1 1 calc R U . . .
P3 P 0.47958(5) 0.08471(3) 0.30377(2) 0.02541(10) Uani 1 1 d . . . . .
O5 O 0.09000(15) 0.14935(8) 0.45746(7) 0.0426(3) Uani 1 1 d . . . . .
O6 O 0.17312(13) 0.02342(8) 0.47857(6) 0.0321(3) Uani 1 1 d . . . . .
C43 C 0.36304(18) -0.00669(10) 0.23743(8) 0.0258(3) Uani 1 1 d . . . . .
C44 C 0.2077(2) -0.05601(11) 0.23739(9) 0.0335(4) Uani 1 1 d . . . . .
H44 H 0.1561 -0.0431 0.2730 0.040 Uiso 1 1 calc R U . . .
C45 C 0.1295(2) -0.12393(12) 0.18505(9) 0.0393(4) Uani 1 1 d . . . . .
H45 H 0.0260 -0.1564 0.1857 0.047 Uiso 1 1 calc R U . . .
C46 C 0.2047(2) -0.14364(12) 0.13172(9) 0.0392(4) Uani 1 1 d . . . . .
H46 H 0.1520 -0.1892 0.0964 0.047 Uiso 1 1 calc R U . . .
C47 C 0.3590(2) -0.09532(13) 0.13107(9) 0.0398(4) Uani 1 1 d . . . . .
H47 H 0.4099 -0.1082 0.0952 0.048 Uiso 1 1 calc R U . . .
C48 C 0.4374(2) -0.02800(12) 0.18364(8) 0.0320(4) Uani 1 1 d . . . . .
H48 H 0.5414 0.0035 0.1831 0.038 Uiso 1 1 calc R U . . .
C49 C 0.44497(18) 0.19292(10) 0.26930(8) 0.0258(3) Uani 1 1 d . . . . .
C50 C 0.5625(2) 0.27634(11) 0.28743(8) 0.0329(4) Uani 1 1 d . . . . .
H50 H 0.6525 0.2752 0.3166 0.039 Uiso 1 1 calc R U . . .
C51 C 0.5469(2) 0.36126(12) 0.26252(10) 0.0400(4) Uani 1 1 d . . . . .
H51 H 0.6259 0.4167 0.2754 0.048 Uiso 1 1 calc R U . . .
C52 C 0.4154(2) 0.36393(12) 0.21889(9) 0.0388(4) Uani 1 1 d . . . . .
H52 H 0.4061 0.4208 0.2017 0.047 Uiso 1 1 calc R U . . .
C53 C 0.2974(2) 0.28204(13) 0.20077(10) 0.0433(4) Uani 1 1 d . . . . .
H53 H 0.2075 0.2838 0.1718 0.052 Uiso 1 1 calc R U . . .
C54 C 0.3123(2) 0.19688(12) 0.22566(9) 0.0372(4) Uani 1 1 d . . . . .
H54 H 0.2324 0.1418 0.2129 0.045 Uiso 1 1 calc R U . . .
C55 C 0.35434(17) 0.06214(10) 0.37153(8) 0.0243(3) Uani 1 1 d . . . . .
C56 C 0.26611(19) 0.11873(11) 0.38675(8) 0.0283(3) Uani 1 1 d . . . . .
H56 H 0.2658 0.1709 0.3609 0.034 Uiso 1 1 calc R U . . .
C57 C 0.17164(19) 0.10144(11) 0.44188(9) 0.0308(4) Uani 1 1 d . . . . .
C58 C 0.26350(18) -0.03567(10) 0.46479(8) 0.0265(3) Uani 1 1 d . . . . .
C59 C 0.35653(17) -0.01875(10) 0.41267(8) 0.0245(3) Uani 1 1 d . . . . .
C60 C 0.44820(19) -0.08062(11) 0.40396(8) 0.0286(3) Uani 1 1 d . . . . .
H60 H 0.5119 -0.0712 0.3697 0.034 Uiso 1 1 calc R U . . .
C61 C 0.44518(19) -0.15495(11) 0.44536(9) 0.0315(4) Uani 1 1 d . . . . .
H61 H 0.5075 -0.1950 0.4393 0.038 Uiso 1 1 calc R U . . .
C62 C 0.3495(2) -0.17052(11) 0.49626(9) 0.0325(4) Uani 1 1 d . . . . .
H62 H 0.3472 -0.2213 0.5238 0.039 Uiso 1 1 calc R U . . .
C63 C 0.25767(19) -0.11103(11) 0.50631(8) 0.0310(4) Uani 1 1 d . . . . .
H63 H 0.1932 -0.1213 0.5403 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.8245(18) . ?
P1 C13 1.8321(16) . ?
P1 C7 1.8321(19) . ?
O1 C15 1.212(2) . ?
O2 C15 1.368(2) . ?
O2 C16 1.380(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.384(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.350(2) . ?
C13 C17 1.453(2) . ?
C14 C15 1.446(2) . ?
C14 H14 0.9300 . ?
C16 C21 1.382(2) . ?
C16 C17 1.395(2) . ?
C17 C18 1.400(2) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
P2 C22 1.8256(17) . ?
P2 C28 1.8311(16) . ?
P2 C34 1.8413(15) . ?
O3 C36 1.209(2) . ?
O4 C36 1.3672(19) . ?
O4 C37 1.3785(19) . ?
C22 C27 1.390(2) . ?
C22 C23 1.395(2) . ?
C23 C24 1.379(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.387(2) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C33 1.392(2) . ?
C28 C29 1.398(2) . ?
C29 C30 1.385(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.377(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.385(2) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.347(2) . ?
C34 C38 1.457(2) . ?
C35 C36 1.448(2) . ?
C35 H35 0.9300 . ?
C37 C42 1.386(2) . ?
C37 C38 1.392(2) . ?
C38 C39 1.398(2) . ?
C39 C40 1.378(2) . ?
C39 H39 0.9300 . ?
C40 C41 1.385(2) . ?
C40 H40 0.9300 . ?
C41 C42 1.384(2) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
P3 C49 1.8297(16) . ?
P3 C55 1.8362(15) . ?
P3 C43 1.8360(16) . ?
O5 C57 1.2058(19) . ?
O6 C57 1.3718(19) . ?
O6 C58 1.3830(18) . ?
C43 C48 1.392(2) . ?
C43 C44 1.395(2) . ?
C44 C45 1.383(2) . ?
C44 H44 0.9300 . ?
C45 C46 1.382(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.385(3) . ?
C46 H46 0.9300 . ?
C47 C48 1.381(2) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C54 1.387(2) . ?
C49 C50 1.391(2) . ?
C50 C51 1.387(2) . ?
C50 H50 0.9300 . ?
C51 C52 1.373(3) . ?
C51 H51 0.9300 . ?
C52 C53 1.378(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.388(2) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 C56 1.347(2) . ?
C55 C59 1.457(2) . ?
C56 C57 1.450(2) . ?
C56 H56 0.9300 . ?
C58 C63 1.386(2) . ?
C58 C59 1.393(2) . ?
C59 C60 1.402(2) . ?
C60 C61 1.375(2) . ?
C60 H60 0.9300 . ?
C61 C62 1.389(2) . ?
C61 H61 0.9300 . ?
C62 C63 1.381(2) . ?
C62 H62 0.9300 . ?
C63 H63 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C13 103.39(7) . . ?
C1 P1 C7 104.65(8) . . ?
C13 P1 C7 100.59(8) . . ?
C15 O2 C16 121.54(13) . . ?
C2 C1 C6 118.03(17) . . ?
C2 C1 P1 124.12(14) . . ?
C6 C1 P1 117.63(13) . . ?
C3 C2 C1 120.60(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.61(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.03(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.94(17) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C12 C7 C8 118.6(2) . . ?
C12 C7 P1 124.06(14) . . ?
C8 C7 P1 117.27(17) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 120.5(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C17 118.42(14) . . ?
C14 C13 P1 123.26(13) . . ?
C17 C13 P1 118.23(12) . . ?
C13 C14 C15 122.69(16) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
O1 C15 O2 117.16(15) . . ?
O1 C15 C14 125.35(16) . . ?
O2 C15 C14 117.49(15) . . ?
O2 C16 C21 116.10(16) . . ?
O2 C16 C17 121.42(15) . . ?
C21 C16 C17 122.48(17) . . ?
C16 C17 C18 117.12(16) . . ?
C16 C17 C13 118.38(15) . . ?
C18 C17 C13 124.51(15) . . ?
C19 C18 C17 120.86(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.22(18) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.35(18) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 118.96(19) . . ?
C20 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
C22 P2 C28 104.32(7) . . ?
C22 P2 C34 103.09(7) . . ?
C28 P2 C34 99.80(7) . . ?
C36 O4 C37 121.28(12) . . ?
C27 C22 C23 118.58(16) . . ?
C27 C22 P2 124.98(13) . . ?
C23 C22 P2 116.39(13) . . ?
C24 C23 C22 120.77(18) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.04(18) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.03(18) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.18(19) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 120.38(17) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
C33 C28 C29 118.78(14) . . ?
C33 C28 P2 124.19(12) . . ?
C29 C28 P2 116.95(12) . . ?
C30 C29 C28 120.22(16) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.22(16) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.25(16) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C33 119.99(16) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 120.53(15) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C35 C34 C38 118.27(14) . . ?
C35 C34 P2 123.70(12) . . ?
C38 C34 P2 117.96(11) . . ?
C34 C35 C36 122.79(15) . . ?
C34 C35 H35 118.6 . . ?
C36 C35 H35 118.6 . . ?
O3 C36 O4 116.86(15) . . ?
O3 C36 C35 125.60(16) . . ?
O4 C36 C35 117.54(14) . . ?
O4 C37 C42 116.05(14) . . ?
O4 C37 C38 121.80(13) . . ?
C42 C37 C38 122.14(15) . . ?
C37 C38 C39 117.55(14) . . ?
C37 C38 C34 118.27(14) . . ?
C39 C38 C34 124.18(14) . . ?
C40 C39 C38 120.88(16) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C39 C40 C41 120.37(16) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C42 C41 C40 120.16(15) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C37 118.90(15) . . ?
C41 C42 H42 120.6 . . ?
C37 C42 H42 120.6 . . ?
C49 P3 C55 102.59(7) . . ?
C49 P3 C43 102.36(7) . . ?
C55 P3 C43 99.47(7) . . ?
C57 O6 C58 121.62(12) . . ?
C48 C43 C44 118.27(15) . . ?
C48 C43 P3 116.73(12) . . ?
C44 C43 P3 125.01(12) . . ?
C45 C44 C43 120.81(16) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C46 C45 C44 120.15(17) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C45 C46 C47 119.70(16) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
C48 C47 C46 120.12(16) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C47 C48 C43 120.93(16) . . ?
C47 C48 H48 119.5 . . ?
C43 C48 H48 119.5 . . ?
C54 C49 C50 118.32(15) . . ?
C54 C49 P3 124.71(12) . . ?
C50 C49 P3 116.95(12) . . ?
C51 C50 C49 120.68(16) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
C52 C51 C50 120.33(16) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C51 C52 C53 119.74(16) . . ?
C51 C52 H52 120.1 . . ?
C53 C52 H52 120.1 . . ?
C52 C53 C54 120.13(17) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C49 C54 C53 120.79(16) . . ?
C49 C54 H54 119.6 . . ?
C53 C54 H54 119.6 . . ?
C56 C55 C59 118.73(14) . . ?
C56 C55 P3 123.24(12) . . ?
C59 C55 P3 117.97(11) . . ?
C55 C56 C57 122.48(14) . . ?
C55 C56 H56 118.8 . . ?
C57 C56 H56 118.8 . . ?
O5 C57 O6 117.29(14) . . ?
O5 C57 C56 125.27(15) . . ?
O6 C57 C56 117.43(14) . . ?
O6 C58 C63 116.26(14) . . ?
O6 C58 C59 121.33(13) . . ?
C63 C58 C59 122.40(14) . . ?
C58 C59 C60 117.33(14) . . ?
C58 C59 C55 118.37(14) . . ?
C60 C59 C55 124.29(14) . . ?
C61 C60 C59 120.90(15) . . ?
C61 C60 H60 119.5 . . ?
C59 C60 H60 119.5 . . ?
C60 C61 C62 120.26(15) . . ?
C60 C61 H61 119.9 . . ?
C62 C61 H61 119.9 . . ?
C63 C62 C61 120.42(15) . . ?
C63 C62 H62 119.8 . . ?
C61 C62 H62 119.8 . . ?
C62 C63 C58 118.67(15) . . ?
C62 C63 H63 120.7 . . ?
C58 C63 H63 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 P1 C1 C2 109.61(15) . . . . ?
C7 P1 C1 C2 4.69(17) . . . . ?
C13 P1 C1 C6 -76.01(14) . . . . ?
C7 P1 C1 C6 179.07(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
P1 C1 C2 C3 174.59(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
P1 C1 C6 C5 -176.47(15) . . . . ?
C1 P1 C7 C12 90.29(17) . . . . ?
C13 P1 C7 C12 -16.71(17) . . . . ?
C1 P1 C7 C8 -92.71(15) . . . . ?
C13 P1 C7 C8 160.29(14) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
P1 C7 C8 C9 -176.25(17) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
P1 C7 C12 C11 175.22(15) . . . . ?
C10 C11 C12 C7 1.1(3) . . . . ?
C1 P1 C13 C14 1.02(15) . . . . ?
C7 P1 C13 C14 109.03(14) . . . . ?
C1 P1 C13 C17 177.41(11) . . . . ?
C7 P1 C13 C17 -74.59(13) . . . . ?
C17 C13 C14 C15 0.0(2) . . . . ?
P1 C13 C14 C15 176.34(12) . . . . ?
C16 O2 C15 O1 178.65(15) . . . . ?
C16 O2 C15 C14 -2.0(2) . . . . ?
C13 C14 C15 O1 -178.67(17) . . . . ?
C13 C14 C15 O2 2.1(2) . . . . ?
C15 O2 C16 C21 -179.63(14) . . . . ?
C15 O2 C16 C17 0.0(2) . . . . ?
O2 C16 C17 C18 -178.09(14) . . . . ?
C21 C16 C17 C18 1.5(2) . . . . ?
O2 C16 C17 C13 2.1(2) . . . . ?
C21 C16 C17 C13 -178.32(15) . . . . ?
C14 C13 C17 C16 -2.0(2) . . . . ?
P1 C13 C17 C16 -178.58(11) . . . . ?
C14 C13 C17 C18 178.18(15) . . . . ?
P1 C13 C17 C18 1.6(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C13 C17 C18 C19 179.24(15) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C21 1.4(3) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
O2 C16 C21 C20 178.63(14) . . . . ?
C17 C16 C21 C20 -1.0(3) . . . . ?
C28 P2 C22 C27 -17.46(16) . . . . ?
C34 P2 C22 C27 86.41(15) . . . . ?
C28 P2 C22 C23 160.04(12) . . . . ?
C34 P2 C22 C23 -96.09(13) . . . . ?
C27 C22 C23 C24 0.1(3) . . . . ?
P2 C22 C23 C24 -177.58(14) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C22 1.1(3) . . . . ?
C23 C22 C27 C26 -1.0(3) . . . . ?
P2 C22 C27 C26 176.42(13) . . . . ?
C22 P2 C28 C33 87.42(15) . . . . ?
C34 P2 C28 C33 -18.92(15) . . . . ?
C22 P2 C28 C29 -95.88(13) . . . . ?
C34 P2 C28 C29 157.78(12) . . . . ?
C33 C28 C29 C30 0.8(2) . . . . ?
P2 C28 C29 C30 -176.05(13) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C29 C30 C31 C32 -1.2(3) . . . . ?
C30 C31 C32 C33 0.8(3) . . . . ?
C31 C32 C33 C28 0.4(3) . . . . ?
C29 C28 C33 C32 -1.2(2) . . . . ?
P2 C28 C33 C32 175.44(13) . . . . ?
C22 P2 C34 C35 2.91(15) . . . . ?
C28 P2 C34 C35 110.25(14) . . . . ?
C22 P2 C34 C38 179.67(11) . . . . ?
C28 P2 C34 C38 -73.00(12) . . . . ?
C38 C34 C35 C36 2.2(2) . . . . ?
P2 C34 C35 C36 178.90(12) . . . . ?
C37 O4 C36 O3 179.37(14) . . . . ?
C37 O4 C36 C35 -1.0(2) . . . . ?
C34 C35 C36 O3 179.31(17) . . . . ?
C34 C35 C36 O4 -0.3(2) . . . . ?
C36 O4 C37 C42 -178.43(14) . . . . ?
C36 O4 C37 C38 0.3(2) . . . . ?
O4 C37 C38 C39 -178.33(13) . . . . ?
C42 C37 C38 C39 0.3(2) . . . . ?
O4 C37 C38 C34 1.6(2) . . . . ?
C42 C37 C38 C34 -179.80(13) . . . . ?
C35 C34 C38 C37 -2.7(2) . . . . ?
P2 C34 C38 C37 -179.67(11) . . . . ?
C35 C34 C38 C39 177.15(15) . . . . ?
P2 C34 C38 C39 0.22(19) . . . . ?
C37 C38 C39 C40 0.3(2) . . . . ?
C34 C38 C39 C40 -179.58(14) . . . . ?
C38 C39 C40 C41 -0.5(2) . . . . ?
C39 C40 C41 C42 0.2(2) . . . . ?
C40 C41 C42 C37 0.4(2) . . . . ?
O4 C37 C42 C41 178.03(13) . . . . ?
C38 C37 C42 C41 -0.7(2) . . . . ?
C49 P3 C43 C48 90.10(13) . . . . ?
C55 P3 C43 C48 -164.66(12) . . . . ?
C49 P3 C43 C44 -90.35(15) . . . . ?
C55 P3 C43 C44 14.89(15) . . . . ?
C48 C43 C44 C45 -0.4(2) . . . . ?
P3 C43 C44 C45 -179.90(13) . . . . ?
C43 C44 C45 C46 -0.2(3) . . . . ?
C44 C45 C46 C47 0.2(3) . . . . ?
C45 C46 C47 C48 0.3(3) . . . . ?
C46 C47 C48 C43 -0.8(3) . . . . ?
C44 C43 C48 C47 0.9(2) . . . . ?
P3 C43 C48 C47 -179.56(13) . . . . ?
C55 P3 C49 C54 -75.78(15) . . . . ?
C43 P3 C49 C54 27.03(16) . . . . ?
C55 P3 C49 C50 105.63(13) . . . . ?
C43 P3 C49 C50 -151.57(12) . . . . ?
C54 C49 C50 C51 0.1(2) . . . . ?
P3 C49 C50 C51 178.82(13) . . . . ?
C49 C50 C51 C52 -0.7(3) . . . . ?
C50 C51 C52 C53 1.1(3) . . . . ?
C51 C52 C53 C54 -1.0(3) . . . . ?
C50 C49 C54 C53 0.0(3) . . . . ?
P3 C49 C54 C53 -178.60(14) . . . . ?
C52 C53 C54 C49 0.5(3) . . . . ?
C49 P3 C55 C56 -0.65(15) . . . . ?
C43 P3 C55 C56 -105.70(14) . . . . ?
C49 P3 C55 C59 -177.82(11) . . . . ?
C43 P3 C55 C59 77.13(12) . . . . ?
C59 C55 C56 C57 -0.9(2) . . . . ?
P3 C55 C56 C57 -178.02(12) . . . . ?
C58 O6 C57 O5 -179.71(15) . . . . ?
C58 O6 C57 C56 1.4(2) . . . . ?
C55 C56 C57 O5 -179.56(16) . . . . ?
C55 C56 C57 O6 -0.7(2) . . . . ?
C57 O6 C58 C63 178.67(14) . . . . ?
C57 O6 C58 C59 -0.4(2) . . . . ?
O6 C58 C59 C60 177.91(14) . . . . ?
C63 C58 C59 C60 -1.1(2) . . . . ?
O6 C58 C59 C55 -1.3(2) . . . . ?
C63 C58 C59 C55 179.76(14) . . . . ?
C56 C55 C59 C58 1.9(2) . . . . ?
P3 C55 C59 C58 179.15(11) . . . . ?
C56 C55 C59 C60 -177.26(15) . . . . ?
P3 C55 C59 C60 0.0(2) . . . . ?
C58 C59 C60 C61 0.2(2) . . . . ?
C55 C59 C60 C61 179.30(14) . . . . ?
C59 C60 C61 C62 0.7(2) . . . . ?
C60 C61 C62 C63 -0.7(2) . . . . ?
C61 C62 C63 C58 -0.2(2) . . . . ?
O6 C58 C63 C62 -177.95(14) . . . . ?
C59 C58 C63 C62 1.1(2) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_yfj-1_02
_audit_block_doi                 10.5517/ccdc.csd.cc294tmx
_database_code_depnum_ccdc_archive 'CCDC 2119799'
loop_
_audit_author_name
_audit_author_address
'DPP-modified coumarin'
;Peking University
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 O2 P'
_chemical_formula_weight         344.32

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+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                   8.0623(2)
_cell_length_b                   14.6716(6)
_cell_length_c                   29.7285(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3516.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16318
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.741
_diffrn_reflns_theta_max         31.218
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4601
_reflns_number_gt                3258
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0572P)²+1.4552P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P11 P 0.58659(5) 0.60614(3) 0.65476(2) 0.01516(12) Uani 1 1 d . . . . .
O1 O 0.94177(14) 0.61102(10) 0.51364(4) 0.0223(3) Uani 1 1 d . . . . .
O24 O 1.12237(15) 0.60573(11) 0.45763(5) 0.0308(4) Uani 1 1 d . . . . .
C12 C 0.64701(19) 0.72047(12) 0.67315(6) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.7799(2) 0.61548(13) 0.52902(6) 0.0175(4) Uani 1 1 d . . . . .
C13 C 0.6636(2) 0.79546(13) 0.64448(6) 0.0173(4) Uani 1 1 d . . . . .
H13 H 0.6369 0.7897 0.6142 0.021 Uiso 1 1 calc R U . . .
C18 C 0.3638(2) 0.60393(12) 0.66632(6) 0.0153(3) Uani 1 1 d . . . . .
C15 C 0.7611(2) 0.88735(13) 0.70610(6) 0.0192(4) Uani 1 1 d . . . . .
H15 H 0.7996 0.9429 0.7170 0.023 Uiso 1 1 calc R U . . .
C16 C 0.7451(2) 0.81388(13) 0.73473(6) 0.0203(4) Uani 1 1 d . . . . .
H16 H 0.7720 0.8202 0.7650 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5996(2) 0.61606(12) 0.59342(6) 0.0167(3) Uani 1 1 d . . . . .
C23 C 0.3000(2) 0.52209(13) 0.68261(6) 0.0193(4) Uani 1 1 d . . . . .
H23 H 0.3698 0.4722 0.6863 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6458(2) 0.62223(12) 0.49913(6) 0.0173(4) Uani 1 1 d . . . . .
C3 C 0.7590(2) 0.61174(13) 0.57500(6) 0.0173(4) Uani 1 1 d . . . . .
H3 H 0.8508 0.6064 0.5937 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4633(2) 0.62241(13) 0.56414(6) 0.0196(4) Uani 1 1 d . . . . .
H5 H 0.3565 0.6246 0.5759 0.024 Uiso 1 1 calc R U . . .
C17 C 0.6891(2) 0.73051(13) 0.71867(6) 0.0182(4) Uani 1 1 d . . . . .
H17 H 0.6794 0.6812 0.7381 0.022 Uiso 1 1 calc R U . . .
C21 C 0.0289(2) 0.58864(14) 0.68851(6) 0.0213(4) Uani 1 1 d . . . . .
H21 H -0.0826 0.5837 0.6961 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7196(2) 0.87845(13) 0.66089(6) 0.0188(4) Uani 1 1 d . . . . .
H14 H 0.7294 0.9282 0.6417 0.023 Uiso 1 1 calc R U . . .
C22 C 0.1321(2) 0.51436(14) 0.69350(6) 0.0231(4) Uani 1 1 d . . . . .
H22 H 0.0900 0.4594 0.7041 0.028 Uiso 1 1 calc R U . . .
C20 C 0.0903(2) 0.67068(13) 0.67225(6) 0.0199(4) Uani 1 1 d . . . . .
H20 H 0.0199 0.7204 0.6688 0.024 Uiso 1 1 calc R U . . .
C19 C 0.2573(2) 0.67837(13) 0.66114(6) 0.0183(4) Uani 1 1 d . . . . .
H19 H 0.2983 0.7333 0.6502 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4859(2) 0.62541(13) 0.51801(6) 0.0204(4) Uani 1 1 d . . . . .
H6 H 0.3941 0.6296 0.4992 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9774(2) 0.61023(14) 0.46810(6) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.6795(2) 0.62282(13) 0.45108(6) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.8384(2) 0.61568(14) 0.43738(6) 0.0230(4) Uani 1 1 d . . . . .
H9 H 0.8597 0.6142 0.4066 0.028 Uiso 1 1 calc R U . . .
C25 C 0.5382(2) 0.63217(15) 0.41857(6) 0.0249(4) Uani 1 1 d . . . . .
H25A H 0.4599 0.5839 0.4235 0.037 Uiso 1 1 calc R U . . .
H25B H 0.5797 0.6286 0.3884 0.037 Uiso 1 1 calc R U . . .
H25C H 0.4847 0.6899 0.4230 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P11 C18 1.8290(17) . ?
P11 C12 1.8303(18) . ?
P11 C4 1.8323(18) . ?
O1 C10 1.384(2) . ?
O1 C2 1.3847(19) . ?
O24 C10 1.212(2) . ?
C12 C13 1.398(2) . ?
C12 C17 1.403(2) . ?
C2 C3 1.378(2) . ?
C2 C7 1.403(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C18 C23 1.393(3) . ?
C18 C19 1.398(2) . ?
C15 C16 1.379(3) . ?
C15 C14 1.391(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C4 C3 1.399(2) . ?
C4 C5 1.405(2) . ?
C23 C22 1.397(2) . ?
C23 H23 0.9300 . ?
C7 C6 1.406(2) . ?
C7 C8 1.454(2) . ?
C3 H3 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C21 C22 1.379(3) . ?
C21 C20 1.388(3) . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?
C20 C19 1.391(2) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C10 C9 1.448(3) . ?
C8 C9 1.348(2) . ?
C8 C25 1.500(2) . ?
C9 H9 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 P11 C12 102.80(8) . . ?
C18 P11 C4 104.15(7) . . ?
C12 P11 C4 102.08(8) . . ?
C10 O1 C2 121.26(14) . . ?
C13 C12 C17 118.84(16) . . ?
C13 C12 P11 124.38(14) . . ?
C17 C12 P11 116.65(13) . . ?
C3 C2 O1 116.14(15) . . ?
C3 C2 C7 122.47(15) . . ?
O1 C2 C7 121.38(16) . . ?
C14 C13 C12 120.50(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C23 C18 C19 118.99(15) . . ?
C23 C18 P11 116.32(13) . . ?
C19 C18 P11 124.66(14) . . ?
C16 C15 C14 120.02(17) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.44(16) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C3 C4 C5 118.61(16) . . ?
C3 C4 P11 116.02(13) . . ?
C5 C4 P11 125.27(13) . . ?
C18 C23 C22 120.57(17) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C2 C7 C6 117.12(16) . . ?
C2 C7 C8 118.59(15) . . ?
C6 C7 C8 124.26(16) . . ?
C2 C3 C4 119.92(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C6 C5 C4 120.87(16) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C16 C17 C12 120.18(17) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C22 C21 C20 120.51(16) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C13 C14 C15 120.02(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C21 C22 C23 119.71(18) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C21 C20 C19 119.87(17) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C19 C18 120.34(17) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C5 C6 C7 120.99(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
O24 C10 O1 116.87(16) . . ?
O24 C10 C9 125.99(17) . . ?
O1 C10 C9 117.14(15) . . ?
C9 C8 C7 118.30(16) . . ?
C9 C8 C25 122.25(17) . . ?
C7 C8 C25 119.44(15) . . ?
C8 C9 C10 123.29(17) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C8 C25 H25A 109.5 . . ?
C8 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C8 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 P11 C12 C13 -96.96(15) . . . . ?
C4 P11 C12 C13 10.80(16) . . . . ?
C18 P11 C12 C17 87.28(13) . . . . ?
C4 P11 C12 C17 -164.96(12) . . . . ?
C10 O1 C2 C3 177.22(17) . . . . ?
C10 O1 C2 C7 -2.0(3) . . . . ?
C17 C12 C13 C14 -0.5(2) . . . . ?
P11 C12 C13 C14 -176.13(13) . . . . ?
C12 P11 C18 C23 -141.73(14) . . . . ?
C4 P11 C18 C23 112.10(14) . . . . ?
C12 P11 C18 C19 36.40(17) . . . . ?
C4 P11 C18 C19 -69.77(17) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C18 P11 C4 C3 -174.97(14) . . . . ?
C12 P11 C4 C3 78.32(15) . . . . ?
C18 P11 C4 C5 1.34(18) . . . . ?
C12 P11 C4 C5 -105.37(16) . . . . ?
C19 C18 C23 C22 0.1(3) . . . . ?
P11 C18 C23 C22 178.39(14) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
O1 C2 C7 C6 179.36(17) . . . . ?
C3 C2 C7 C8 -178.05(18) . . . . ?
O1 C2 C7 C8 1.1(3) . . . . ?
O1 C2 C3 C4 179.83(16) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
P11 C4 C3 C2 177.78(15) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
P11 C4 C5 C6 -176.96(15) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C13 C12 C17 C16 0.4(2) . . . . ?
P11 C12 C17 C16 176.43(13) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C16 C15 C14 C13 -0.6(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C18 C23 C22 C21 -0.6(3) . . . . ?
C22 C21 C20 C19 -0.4(3) . . . . ?
C21 C20 C19 C18 -0.1(3) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
P11 C18 C19 C20 -177.86(13) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C2 C7 C6 C5 0.3(3) . . . . ?
C8 C7 C6 C5 178.44(18) . . . . ?
C2 O1 C10 O24 -179.62(18) . . . . ?
C2 O1 C10 C9 0.9(3) . . . . ?
C2 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -177.28(19) . . . . ?
C2 C7 C8 C25 -178.59(17) . . . . ?
C6 C7 C8 C25 3.3(3) . . . . ?
C7 C8 C9 C10 -1.9(3) . . . . ?
C25 C8 C9 C10 177.46(19) . . . . ?
O24 C10 C9 C8 -178.3(2) . . . . ?
O1 C10 C9 C8 1.1(3) . . . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_yfj-3
_database_code_depnum_ccdc_archive 'CCDC 2119798'
loop_
_audit_author_name
_audit_author_address
'DPP-modified coumarin'
;Peking University
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 O4 P'
_chemical_formula_weight         402.36

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3656(2)
_cell_length_b                   12.6487(4)
_cell_length_c                   15.2302(5)
_cell_angle_alpha                81.699(3)
_cell_angle_beta                 80.761(3)
_cell_angle_gamma                85.473(3)
_cell_volume                     1007.90(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14431
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         31.284
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5443
_reflns_number_gt                4223
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0561P)²+0.2461P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5443
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P001 P 0.09262(8) 0.79270(3) 0.36608(3) 0.01839(11) Uani 1 1 d . . . . .
O002 O 0.8386(2) 0.37733(9) -0.02981(7) 0.0196(2) Uani 1 1 d . . . . .
O003 O 0.1583(2) 0.32325(9) 0.13437(7) 0.0216(3) Uani 1 1 d . . . . .
O004 O 0.1891(2) 0.45921(8) 0.20707(7) 0.0179(2) Uani 1 1 d . . . . .
O005 O 0.6207(2) 0.24148(9) 0.04914(8) 0.0266(3) Uani 1 1 d . . . . .
C006 C 0.2841(3) 0.70647(12) 0.29042(9) 0.0168(3) Uani 1 1 d . . . . .
C007 C 0.6502(3) 0.66531(12) 0.18273(10) 0.0184(3) Uani 1 1 d . . . . .
H007 H 0.8080 0.6827 0.1512 0.022 Uiso 1 1 calc R U . . .
C008 C 0.6620(3) 0.49980(12) 0.10975(9) 0.0164(3) Uani 1 1 d . . . . .
H008 H 0.8214 0.5133 0.0776 0.020 Uiso 1 1 calc R U . . .
C009 C 0.5468(3) 0.41247(12) 0.09817(9) 0.0162(3) Uani 1 1 d . . . . .
C00A C 0.5442(3) 0.57157(12) 0.17031(9) 0.0157(3) Uani 1 1 d . . . . .
C00B C 0.2625(3) 0.91601(12) 0.33687(10) 0.0192(3) Uani 1 1 d . . . . .
C00C C 0.3067(3) 0.54763(12) 0.21917(9) 0.0164(3) Uani 1 1 d . . . . .
C00D C 0.1782(3) 0.61274(12) 0.27915(10) 0.0176(3) Uani 1 1 d . . . . .
H00D H 0.0223 0.5943 0.3118 0.021 Uiso 1 1 calc R U . . .
C00E C 0.6837(3) 0.34316(12) 0.03258(10) 0.0173(3) Uani 1 1 d . . . . .
C00F C 0.1831(3) 0.73539(12) 0.47459(10) 0.0189(3) Uani 1 1 d . . . . .
C00G C 0.2912(3) 0.39124(12) 0.14474(9) 0.0167(3) Uani 1 1 d . . . . .
C00H C 0.5225(3) 0.73197(13) 0.24137(10) 0.0191(3) Uani 1 1 d . . . . .
H00H H 0.5943 0.7941 0.2485 0.023 Uiso 1 1 calc R U . . .
C00I C 0.0234(3) 0.76249(13) 0.55102(10) 0.0221(3) Uani 1 1 d . . . . .
H00I H -0.1187 0.8084 0.5448 0.027 Uiso 1 1 calc R U . . .
C00J C 0.4389(3) 0.94644(13) 0.38515(11) 0.0225(3) Uani 1 1 d . . . . .
H00J H 0.4735 0.9036 0.4373 0.027 Uiso 1 1 calc R U . . .
C00K C 0.3942(3) 0.66615(14) 0.48548(11) 0.0255(4) Uani 1 1 d . . . . .
H00K H 0.5031 0.6479 0.4353 0.031 Uiso 1 1 calc R U . . .
C00L C 0.2111(3) 0.98290(13) 0.25975(11) 0.0255(4) Uani 1 1 d . . . . .
H00L H 0.0890 0.9651 0.2283 0.031 Uiso 1 1 calc R U . . .
C00M C 0.5632(4) 1.04045(14) 0.35578(12) 0.0283(4) Uani 1 1 d . . . . .
H00M H 0.6789 1.0607 0.3888 0.034 Uiso 1 1 calc R U . . .
C00N C 0.0754(4) 0.72130(14) 0.63615(11) 0.0275(4) Uani 1 1 d . . . . .
H00N H -0.0299 0.7408 0.6866 0.033 Uiso 1 1 calc R U . . .
C00O C 0.4434(4) 0.62394(14) 0.57121(11) 0.0291(4) Uani 1 1 d . . . . .
H00O H 0.5840 0.5773 0.5780 0.035 Uiso 1 1 calc R U . . .
C00P C 0.2833(4) 0.65151(14) 0.64593(11) 0.0278(4) Uani 1 1 d . . . . .
H00P H 0.3156 0.6229 0.7030 0.033 Uiso 1 1 calc R U . . .
C00Q C 0.5156(4) 1.10393(14) 0.27773(12) 0.0304(4) Uani 1 1 d . . . . .
H00Q H 0.6019 1.1659 0.2577 0.036 Uiso 1 1 calc R U . . .
C00R C 0.3392(4) 1.07542(14) 0.22925(12) 0.0306(4) Uani 1 1 d . . . . .
H00R H 0.3071 1.1180 0.1767 0.037 Uiso 1 1 calc R U . . .
C00S C 0.7577(3) 0.17091(14) -0.01350(12) 0.0279(4) Uani 1 1 d . . . . .
H00A H 0.7753 0.2083 -0.0742 0.033 Uiso 1 1 calc R U . . .
H00B H 0.6628 0.1082 -0.0114 0.033 Uiso 1 1 calc R U . . .
C00T C 1.0142(4) 0.13732(16) 0.01146(14) 0.0377(5) Uani 1 1 d . . . . .
H00C H 1.1053 0.0938 -0.0311 0.056 Uiso 1 1 calc R U . . .
H00E H 0.9959 0.0970 0.0703 0.056 Uiso 1 1 calc R U . . .
H00F H 1.1056 0.1997 0.0112 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P001 C00F 1.8299(16) . ?
P001 C00B 1.8318(16) . ?
P001 C006 1.8383(16) . ?
O002 C00E 1.2102(18) . ?
O003 C00G 1.2020(18) . ?
O004 C00C 1.3751(17) . ?
O004 C00G 1.3911(18) . ?
O005 C00E 1.3339(18) . ?
O005 C00S 1.471(2) . ?
C006 C00D 1.398(2) . ?
C006 C00H 1.409(2) . ?
C007 C00H 1.381(2) . ?
C007 C00A 1.404(2) . ?
C007 H007 0.9300 . ?
C008 C009 1.354(2) . ?
C008 C00A 1.428(2) . ?
C008 H008 0.9300 . ?
C009 C00G 1.465(2) . ?
C009 C00E 1.491(2) . ?
C00A C00C 1.400(2) . ?
C00B C00J 1.395(2) . ?
C00B C00L 1.397(2) . ?
C00C C00D 1.383(2) . ?
C00D H00D 0.9300 . ?
C00F C00K 1.393(2) . ?
C00F C00I 1.398(2) . ?
C00H H00H 0.9300 . ?
C00I C00N 1.389(2) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.391(2) . ?
C00J H00J 0.9300 . ?
C00K C00O 1.395(2) . ?
C00K H00K 0.9300 . ?
C00L C00R 1.387(2) . ?
C00L H00L 0.9300 . ?
C00M C00Q 1.383(3) . ?
C00M H00M 0.9300 . ?
C00N C00P 1.380(3) . ?
C00N H00N 0.9300 . ?
C00O C00P 1.382(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q C00R 1.388(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S C00T 1.500(3) . ?
C00S H00A 0.9700 . ?
C00S H00B 0.9700 . ?
C00T H00C 0.9600 . ?
C00T H00E 0.9600 . ?
C00T H00F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00F P001 C00B 103.62(7) . . ?
C00F P001 C006 101.53(7) . . ?
C00B P001 C006 100.88(7) . . ?
C00C O004 C00G 122.98(12) . . ?
C00E O005 C00S 115.16(12) . . ?
C00D C006 C00H 119.24(14) . . ?
C00D C006 P001 116.85(11) . . ?
C00H C006 P001 123.85(11) . . ?
C00H C007 C00A 120.68(14) . . ?
C00H C007 H007 119.7 . . ?
C00A C007 H007 119.7 . . ?
C009 C008 C00A 121.42(14) . . ?
C009 C008 H008 119.3 . . ?
C00A C008 H008 119.3 . . ?
C008 C009 C00G 120.75(14) . . ?
C008 C009 C00E 117.42(13) . . ?
C00G C009 C00E 121.73(13) . . ?
C00C C00A C007 118.15(14) . . ?
C00C C00A C008 117.86(13) . . ?
C007 C00A C008 123.98(14) . . ?
C00J C00B C00L 118.51(15) . . ?
C00J C00B P001 124.87(12) . . ?
C00L C00B P001 116.62(12) . . ?
O004 C00C C00D 117.43(13) . . ?
O004 C00C C00A 120.71(13) . . ?
C00D C00C C00A 121.84(14) . . ?
C00C C00D C006 119.60(14) . . ?
C00C C00D H00D 120.2 . . ?
C006 C00D H00D 120.2 . . ?
O002 C00E O005 123.67(14) . . ?
O002 C00E C009 122.18(13) . . ?
O005 C00E C009 114.15(13) . . ?
C00K C00F C00I 118.80(15) . . ?
C00K C00F P001 124.62(12) . . ?
C00I C00F P001 116.56(13) . . ?
O003 C00G O004 116.35(13) . . ?
O003 C00G C009 127.68(14) . . ?
O004 C00G C009 115.96(12) . . ?
C007 C00H C006 120.48(14) . . ?
C007 C00H H00H 119.8 . . ?
C006 C00H H00H 119.8 . . ?
C00N C00I C00F 120.45(17) . . ?
C00N C00I H00I 119.8 . . ?
C00F C00I H00I 119.8 . . ?
C00M C00J C00B 120.38(15) . . ?
C00M C00J H00J 119.8 . . ?
C00B C00J H00J 119.8 . . ?
C00F C00K C00O 120.43(16) . . ?
C00F C00K H00K 119.8 . . ?
C00O C00K H00K 119.8 . . ?
C00R C00L C00B 121.14(16) . . ?
C00R C00L H00L 119.4 . . ?
C00B C00L H00L 119.4 . . ?
C00Q C00M C00J 120.24(16) . . ?
C00Q C00M H00M 119.9 . . ?
C00J C00M H00M 119.9 . . ?
C00P C00N C00I 120.12(16) . . ?
C00P C00N H00N 119.9 . . ?
C00I C00N H00N 119.9 . . ?
C00P C00O C00K 119.95(17) . . ?
C00P C00O H00O 120.0 . . ?
C00K C00O H00O 120.0 . . ?
C00N C00P C00O 120.24(15) . . ?
C00N C00P H00P 119.9 . . ?
C00O C00P H00P 119.9 . . ?
C00M C00Q C00R 120.18(16) . . ?
C00M C00Q H00Q 119.9 . . ?
C00R C00Q H00Q 119.9 . . ?
C00L C00R C00Q 119.49(16) . . ?
C00L C00R H00R 120.3 . . ?
C00Q C00R H00R 120.3 . . ?
O005 C00S C00T 109.87(14) . . ?
O005 C00S H00A 109.7 . . ?
C00T C00S H00A 109.7 . . ?
O005 C00S H00B 109.7 . . ?
C00T C00S H00B 109.7 . . ?
H00A C00S H00B 108.2 . . ?
C00S C00T H00C 109.5 . . ?
C00S C00T H00E 109.5 . . ?
H00C C00T H00E 109.5 . . ?
C00S C00T H00F 109.5 . . ?
H00C C00T H00F 109.5 . . ?
H00E C00T H00F 109.5 . . ?

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_yfj-5
_audit_block_doi                 10.5517/ccdc.csd.cc294tkv
_database_code_depnum_ccdc_archive 'CCDC 2119797'
loop_
_audit_author_name
_audit_author_address
'DPP-modified coumarin'
;Peking University
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;
_audit_creation_date             2020-08-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H17 O3 P'
_chemical_formula_sum            'C23 H17 O3 P'
_chemical_formula_weight         372.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O P'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.4282(9)
_cell_length_b                   13.8412(7)
_cell_length_c                   9.7598(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.854(5)
_cell_angle_gamma                90
_cell_volume                     1811.73(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4545
_cell_measurement_temperature    100.00(14)
_cell_measurement_theta_max      29.6740
_cell_measurement_theta_min      2.5280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sheet
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15183
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.316
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  41.00   0.50   51.24    --   10.95 -81.00  58.00  144
  2  ω    -18.00  44.00   0.50   51.24    --   10.95 -99.00 -30.00  124
  3  ω    -19.00  32.00   0.50   51.24    --   10.95  81.00-179.00  102
  4  ω    -22.00  35.00   0.50   51.24    --  -12.67  81.00-179.00  114
  5  ω    -91.00 -42.00   0.50   51.24    --  -12.67 178.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0474720000
_diffrn_orient_matrix_UB_12      0.0215961000
_diffrn_orient_matrix_UB_13      -0.0061781000
_diffrn_orient_matrix_UB_21      0.0143128000
_diffrn_orient_matrix_UB_22      -0.0387438000
_diffrn_orient_matrix_UB_23      -0.0422895000
_diffrn_orient_matrix_UB_31      -0.0183848000
_diffrn_orient_matrix_UB_32      0.0256409000
_diffrn_orient_matrix_UB_33      -0.0589144000
_diffrn_oxdiff_digest_frames     
;
018091a0c22e0e69053e7c3b1422613c2300025590d
;
_diffrn_oxdiff_digest_hkl        
;
01a9061e95fc76e2472348fc2d263d62a91c92
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3558
_reflns_number_total             4754
_reflns_odcompleteness_completeness 98.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0848P)²+1.7393P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1793
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C2(H2), C5(H5), C22(H22), C13(H13), C17(H17), C16(H16), C4(H4),
 C7(H7), C15(H15), C19(H19), C20(H20), C21(H21), C14(H14)
2.b Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P11 P 0.79841(5) 0.51011(5) 0.38161(7) 0.01885(18) Uani 1 1 d . . . . .
O10 O 0.57299(13) 0.33171(13) 0.01341(18) 0.0209(4) Uani 1 1 d . . . . .
O25 O 0.21833(14) 0.36160(14) -0.0268(2) 0.0286(5) Uani 1 1 d . . . . .
O27 O 0.49177(15) 0.24146(15) -0.1401(2) 0.0353(5) Uani 1 1 d . . . . .
C12 C 0.78031(19) 0.45382(18) 0.5485(3) 0.0189(5) Uani 1 1 d . . . . .
C23 C 0.91401(19) 0.44717(19) 0.1715(3) 0.0208(5) Uani 1 1 d . . . . .
H23 H 0.8910 0.5033 0.1281 0.025 Uiso 1 1 calc R . . . .
C2 C 0.67039(18) 0.41639(17) 0.1807(3) 0.0182(5) Uani 1 1 d . . . . .
H2 H 0.7267 0.3865 0.1487 0.022 Uiso 1 1 calc R . . . .
C6 C 0.49068(18) 0.44102(17) 0.1631(2) 0.0175(5) Uani 1 1 d . . . . .
C18 C 0.88362(18) 0.42491(17) 0.3039(3) 0.0178(5) Uani 1 1 d . . . . .
C8 C 0.39280(18) 0.34659(17) -0.0056(3) 0.0184(5) Uani 1 1 d . . . . .
C5 C 0.4999(2) 0.50670(18) 0.2736(3) 0.0217(5) Uani 1 1 d . . . . .
H5 H 0.4435 0.5371 0.3047 0.026 Uiso 1 1 calc R . . . .
C1 C 0.57725(18) 0.39778(17) 0.1190(2) 0.0176(5) Uani 1 1 d . . . . .
C24 C 0.29096(19) 0.31976(19) -0.0668(3) 0.0220(5) Uani 1 1 d . . . . .
C3 C 0.67908(19) 0.48016(17) 0.2907(3) 0.0189(5) Uani 1 1 d . . . . .
C22 C 0.9781(2) 0.38607(19) 0.1050(3) 0.0227(5) Uani 1 1 d . . . . .
H22 H 0.9962 0.4006 0.0166 0.027 Uiso 1 1 calc R . . . .
C13 C 0.83457(19) 0.49291(18) 0.6617(3) 0.0207(5) Uani 1 1 d . . . . .
H13 H 0.8752 0.5464 0.6502 0.025 Uiso 1 1 calc R . . . .
C17 C 0.71765(19) 0.37465(17) 0.5683(3) 0.0199(5) Uani 1 1 d . . . . .
H17 H 0.6809 0.3484 0.4941 0.024 Uiso 1 1 calc R . . . .
C9 C 0.48386(19) 0.30126(18) -0.0519(3) 0.0214(5) Uani 1 1 d . . . . .
C16 C 0.7101(2) 0.33498(18) 0.6987(3) 0.0212(5) Uani 1 1 d . . . . .
H16 H 0.6677 0.2830 0.7115 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5922(2) 0.52592(19) 0.3352(3) 0.0222(5) Uani 1 1 d . . . . .
H4 H 0.5975 0.5698 0.4075 0.027 Uiso 1 1 calc R . . . .
C7 C 0.39788(18) 0.41328(18) 0.0962(3) 0.0192(5) Uani 1 1 d . . . . .
H7 H 0.3393 0.4418 0.1234 0.023 Uiso 1 1 calc R . . . .
C15 C 0.7663(2) 0.37334(19) 0.8102(3) 0.0224(5) Uani 1 1 d . . . . .
H15 H 0.7623 0.3461 0.8969 0.027 Uiso 1 1 calc R . . . .
C19 C 0.9220(2) 0.34172(19) 0.3683(3) 0.0228(5) Uani 1 1 d . . . . .
H19 H 0.9035 0.3262 0.4562 0.027 Uiso 1 1 calc R . . . .
C20 C 0.9877(2) 0.28185(19) 0.3022(3) 0.0243(6) Uani 1 1 d . . . . .
H20 H 1.0132 0.2271 0.3467 0.029 Uiso 1 1 calc R . . . .
C21 C 1.01526(19) 0.30320(19) 0.1704(3) 0.0228(5) Uani 1 1 d . . . . .
H21 H 1.0583 0.2625 0.1260 0.027 Uiso 1 1 calc R . . . .
C14 C 0.8279(2) 0.4521(2) 0.7913(3) 0.0239(6) Uani 1 1 d . . . . .
H14 H 0.8650 0.4778 0.8656 0.029 Uiso 1 1 calc R . . . .
C26 C 0.2806(2) 0.2427(2) -0.1747(3) 0.0346(7) Uani 1 1 d . . . . .
H26A H 0.2113 0.2325 -0.1992 0.052 Uiso 1 1 calc GR . . . .
H26B H 0.3095 0.1836 -0.1396 0.052 Uiso 1 1 calc GR . . . .
H26C H 0.3146 0.2625 -0.2543 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P11 C12 1.833(3) . ?
P11 C18 1.833(3) . ?
P11 C3 1.840(3) . ?
O10 C1 1.377(3) . ?
O10 C9 1.393(3) . ?
O25 C24 1.215(3) . ?
O27 C9 1.203(3) . ?
C12 C13 1.401(3) . ?
C12 C17 1.401(3) . ?
C23 H23 0.9300 . ?
C23 C18 1.409(4) . ?
C23 C22 1.390(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.385(3) . ?
C2 C3 1.391(3) . ?
C6 C5 1.411(3) . ?
C6 C1 1.394(3) . ?
C6 C7 1.430(3) . ?
C18 C19 1.398(3) . ?
C8 C24 1.511(3) . ?
C8 C9 1.465(4) . ?
C8 C7 1.356(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(4) . ?
C24 C26 1.501(4) . ?
C3 C4 1.415(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.393(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.395(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.398(4) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(4) . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 P11 C18 101.96(11) . . ?
C12 P11 C3 100.47(11) . . ?
C18 P11 C3 101.67(11) . . ?
C1 O10 C9 123.1(2) . . ?
C13 C12 P11 116.73(19) . . ?
C17 C12 P11 124.21(19) . . ?
C17 C12 C13 119.1(2) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C18 120.6(2) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
C5 C6 C7 124.3(2) . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 C7 117.7(2) . . ?
C23 C18 P11 117.00(19) . . ?
C19 C18 P11 124.6(2) . . ?
C19 C18 C23 118.4(2) . . ?
C9 C8 C24 121.7(2) . . ?
C7 C8 C24 117.9(2) . . ?
C7 C8 C9 120.3(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
O10 C1 C2 116.9(2) . . ?
O10 C1 C6 120.8(2) . . ?
C2 C1 C6 122.3(2) . . ?
O25 C24 C8 118.7(2) . . ?
O25 C24 C26 121.1(2) . . ?
C26 C24 C8 120.1(2) . . ?
C2 C3 P11 123.57(19) . . ?
C2 C3 C4 118.8(2) . . ?
C4 C3 P11 117.58(19) . . ?
C23 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
O10 C9 C8 116.2(2) . . ?
O27 C9 O10 115.5(2) . . ?
O27 C9 C8 128.3(2) . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C22 C21 H21 120.2 . . ?
C20 C21 C22 119.6(3) . . ?
C20 C21 H21 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P11 C12 C13 C14 -177.61(19) . . . . ?
P11 C12 C17 C16 178.5(2) . . . . ?
P11 C18 C19 C20 -179.0(2) . . . . ?
P11 C3 C4 C5 -179.3(2) . . . . ?
C12 P11 C18 C23 -179.73(19) . . . . ?
C12 P11 C18 C19 -1.5(2) . . . . ?
C12 P11 C3 C2 -112.0(2) . . . . ?
C12 P11 C3 C4 68.8(2) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
C12 C17 C16 C15 -0.9(4) . . . . ?
C23 C18 C19 C20 -0.8(4) . . . . ?
C23 C22 C21 C20 0.2(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C18 P11 C12 C13 101.2(2) . . . . ?
C18 P11 C12 C17 -77.8(2) . . . . ?
C18 P11 C3 C2 -7.3(2) . . . . ?
C18 P11 C3 C4 173.5(2) . . . . ?
C18 C23 C22 C21 -1.8(4) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C5 C6 C1 O10 178.8(2) . . . . ?
C5 C6 C1 C2 0.7(4) . . . . ?
C5 C6 C7 C8 -177.1(2) . . . . ?
C1 O10 C9 O27 -178.2(2) . . . . ?
C1 O10 C9 C8 2.4(3) . . . . ?
C1 C2 C3 P11 179.63(19) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C1 C6 C7 C8 0.7(4) . . . . ?
C24 C8 C9 O10 -179.5(2) . . . . ?
C24 C8 C9 O27 1.2(4) . . . . ?
C24 C8 C7 C6 178.1(2) . . . . ?
C3 P11 C12 C13 -154.3(2) . . . . ?
C3 P11 C12 C17 26.7(2) . . . . ?
C3 P11 C18 C23 76.8(2) . . . . ?
C3 P11 C18 C19 -105.0(2) . . . . ?
C3 C2 C1 O10 -178.0(2) . . . . ?
C3 C2 C1 C6 0.1(4) . . . . ?
C22 C23 C18 P11 -179.63(19) . . . . ?
C22 C23 C18 C19 2.1(4) . . . . ?
C13 C12 C17 C16 -0.5(4) . . . . ?
C17 C12 C13 C14 1.5(4) . . . . ?
C17 C16 C15 C14 1.3(4) . . . . ?
C9 O10 C1 C2 175.7(2) . . . . ?
C9 O10 C1 C6 -2.5(3) . . . . ?
C9 C8 C24 O25 -178.1(2) . . . . ?
C9 C8 C24 C26 2.0(4) . . . . ?
C9 C8 C7 C6 -0.8(4) . . . . ?
C16 C15 C14 C13 -0.3(4) . . . . ?
C7 C6 C5 C4 177.3(2) . . . . ?
C7 C6 C1 O10 0.9(3) . . . . ?
C7 C6 C1 C2 -177.2(2) . . . . ?
C7 C8 C24 O25 3.1(4) . . . . ?
C7 C8 C24 C26 -176.8(3) . . . . ?
C7 C8 C9 O10 -0.7(4) . . . . ?
C7 C8 C9 O27 180.0(3) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.722
