# 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_single_phase
_database_code_depnum_ccdc_archive 'CCDC 2060715'
loop_
_audit_author_name
_audit_author_address
'haneda tsuyoshi'
;asahi kasei corpration
Japan
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_GEOM001_single_phase        
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: powder data
;
_vrf_GEOM002_single_phase        
;
PROBLEM: _geom_bond_atom_site_label_2 is missing
RESPONSE: powder data
;
_vrf_GEOM003_single_phase        
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: powder data
;
_vrf_GEOM006_single_phase        
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: powder data
;
_vrf_GEOM007_single_phase        
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: powder data
;
_vrf_PLAT340_single_phase        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.07667 Ang.
RESPONSE: powder data
;
_vrf_PLAT351_single_phase        
;
PROBLEM: Long   C-H (X0.96,N1.08A)  C22      - H57      .       1.36 Ang.
RESPONSE: powder data
;
_vrf_PLAT411_single_phase        
;
PROBLEM: Short Inter H...H Contact  H31      ..H47      .       1.77 Ang.
RESPONSE: powder data
;
_vrf_PLAT413_single_phase        
;
PROBLEM: Short Inter XH3 .. XHn     H56      ..H61      .       1.83 Ang.
RESPONSE: powder data
;
_vrf_PLAT242_single_phase        
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        P11 Check
RESPONSE: powder data
;
_vrf_PLAT351_single_phase_2      
;
PROBLEM: Long   C-H (X0.96,N1.08A)  C18      - H50      .       1.19 Ang.
RESPONSE: powder data
;
_vrf_PLAT361_single_phase        
;
PROBLEM: Long   C(sp3)-C(sp3) Bond  C23      - C27      .       1.76 Ang.
RESPONSE: powder data
;
_vrf_PLAT411_single_phase_2      
;
PROBLEM: Short Inter H...H Contact  H30      ..H39      .       1.90 Ang.
RESPONSE: powder data
;
# Added during the CSD deposition process: Wednesday 03 February 2021 06:55 AM
# end Validation Reply Form


# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            TBPADP
# Get _chemical_formula_moiety using checkCIF
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C44 H89 O8 P2'
_chemical_formula_weight         808.120
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0021 'International Tables for Crystallography, Vol. C'
O O 0.0087 0.0080 'International Tables for Crystallography, Vol. C'
P P 0.1044 0.1225 'International Tables for Crystallography, Vol. C'
H H -0.0006 0.0000 'International Tables for Crystallography, Vol. C'

#===============================================================================
# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2

_cell_length_a                   21.4300(3)
_cell_length_b                   13.5076(1)
_cell_length_c                   9.2943(1)
_cell_angle_alpha                90
_cell_angle_beta                 113.170(1)
_cell_angle_gamma                90
_cell_volume                     2473.39(5)
# If checkCIF gives a different Z value, change both
# _chemical_formula_sum and _chemical_formula_weight.
_cell_formula_units_Z            2
_cell_measurement_temperature    300

_cell_special_details            ?

_exptl_crystal_density_diffrn    1.0851
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             894.00
_exptl_crystal_description       ?????

# The next three fields give the specimen dimensions in mm.  The equatorial
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              ? # perpendicular to
# equatorial plane

_pd_spec_size_equat              ? # parallel to
# scattering vector
# in transmission

_pd_spec_size_thick              ? # parallel to
# scattering vector
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
# This field should be
# used to give details of the
# container.
; ?
;
_pd_spec_mount_mode              transmission

_pd_spec_shape                   cylinder

_pd_char_particle_morphology     ?
_pd_char_colour                  ?

# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    0.177
# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record
# the powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      300
_diffrn_source                   'Synchrotron radiation'
_diffrn_source_type              'SPring-8 BL19B2'
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  IP
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             step # options are 'step', 'cont',
#' 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;

_diffrn_radiation_wavelength     0.800000
_diffrn_radiation_monochromator  ?

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        6401
_pd_meas_2theta_range_min        3.0000
_pd_meas_2theta_range_max        35.0000
_pd_meas_2theta_range_inc        0.0050

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

#===============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text.

_pd_calc_method                  'Rietveld Refinement'

_pd_proc_ls_profile_function     'split pseudo-Voigt function'
_pd_proc_ls_background_function  'Legendre polynomials'
_pd_proc_ls_pref_orient_corr     
; ?
;
# Replace '; ?' with the following four lines for the March-Dollase function:
#; $P_k = \sum_{j=1}^{m_k} \frac{1}{m_k}
#\left( r^2 \cos^2 \alpha_j +r^{-1}\ sin^2 \alpha_j \right)^{-3/2}$
#with a preferred-orientation vector, (hkl),
#and <i>r</i> = 1.0(0)

_pd_proc_ls_prof_R_factor        0.11422
_pd_proc_ls_prof_wR_factor       0.12856
_pd_proc_ls_prof_wR_expected     0.17980
_refine_ls_R_I_factor            0.19512
_refine_ls_R_Fsqd_factor         0.10497
_refine_ls_R_factor_all          0.10497

_refine_special_details          
; ?
;

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     1/yi
# The following line must be commented out in the absence of H atoms.
#_refine_ls_hydrogen_treatment       ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    70

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   0.7150

_refine_ls_restrained_S_all      ?
# The following item can be obtained by setting NPRINT at 2 in *.ins.
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         ?

_refine_diff_density_max         0.0
_refine_diff_density_min         0.0

# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.

_pd_proc_2theta_range_min        3.0000
_pd_proc_2theta_range_max        35.0000
_pd_proc_2theta_range_inc        0.0050
_pd_proc_wavelength              ?


# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting
# of one data block containing a single powder profile. The value of
# _pd_block_diffractogram_id is used to associate each refinement with
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?

# Give appropriate details in the next two text fields.

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

# The following items are used to identify the programs used.

_computing_data_collection       ?
_computing_cell_refinement       'RIETAN-FP (Izumi and Momma, 2007)'
_computing_data_reduction        ?
_computing_structure_solution    DASH
_computing_structure_refinement  'RIETAN-FP (Izumi and Momma, 2007)'
_computing_molecular_graphics    'VESTA (Momma and Izumi, 2008)'
_computing_publication_material  ?

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_type_symbol
C1 0.793(3) 1.012(4) 0.049(5) 1 4 e Uiso 0.073(3) C
C2 0.830(2) 0.995(4) -0.050(6) 1 4 e Uiso 0.073(3) C
C3 0.708(3) 1.010(3) -0.054(5) 1 4 e Uiso 0.073(3) C
C4 0.901(3) 0.997(4) 0.024(6) 1 4 e Uiso 0.073(3) C
C5 0.669(2) 0.990(3) 0.056(6) 1 4 e Uiso 0.073(3) C
O6 0.939(1) 0.986(2) -0.056(4) 1 4 e Uiso 0.073(3) O
O7 0.922(1) 0.979(2) 0.162(4) 1 4 e Uiso 0.073(3) O
C8 0.594(3) 0.982(4) -0.031(6) 1 4 e Uiso 0.073(3) C
O9 0.566(1) 0.992(2) -0.178(4) 1 4 e Uiso 0.073(3) O
O10 0.558(1) 0.996(2) 0.059(4) 1 4 e Uiso 0.073(3) O
P11 0.248(1) 0.3099(9) -0.011(2) 1 4 e Uiso 0.079(4) P
C12 0.189(3) 0.387(4) 0.001(6) 1 4 e Uiso 0.139(5) C
C13 0.272(2) 0.225(4) 0.138(6) 1 4 e Uiso 0.139(5) C
C14 0.218(2) 0.232(4) -0.186(6) 1 4 e Uiso 0.139(5) C
C15 0.315(3) 0.383(4) 0.002(6) 1 4 e Uiso 0.139(5) C
C16 0.121(2) 0.322(4) 0.025(5) 1 4 e Uiso 0.139(5) C
C17 0.298(3) 0.262(4) 0.312(6) 1 4 e Uiso 0.139(5) C
C18 0.195(2) 0.285(4) -0.349(6) 1 4 e Uiso 0.139(5) C
C19 0.385(2) 0.319(4) 0.036(6) 1 4 e Uiso 0.139(5) C
C20 0.062(3) 0.368(4) -0.028(6) 1 4 e Uiso 0.139(5) C
C21 0.343(2) 0.177(3) 0.420(5) 1 4 e Uiso 0.139(5) C
C22 0.178(2) 0.211(3) -0.486(5) 1 4 e Uiso 0.139(5) C
C23 0.432(3) 0.369(4) 0.004(6) 1 4 e Uiso 0.139(5) C
C24 0.006(2) 0.298(4) -0.007(6) 1 4 e Uiso 0.139(5) C
C25 0.378(2) 0.203(3) 0.616(5) 1 4 e Uiso 0.139(5) C
C26 0.100(2) 0.145(3) -0.541(5) 1 4 e Uiso 0.139(5) C
C27 0.494(2) 0.285(4) 0.001(6) 1 4 e Uiso 0.139(5) C
H28 0.80303 0.9509 0.11432 1 4 e Uiso 0.087(3) H
H29 0.80278 1.06795 0.10378 1 4 e Uiso 0.087(3) H
H30 0.80807 0.94256 -0.12323 1 4 e Uiso 0.087(3) H
H31 0.81125 1.05965 -0.12683 1 4 e Uiso 0.087(3) H
H32 0.69449 1.06798 -0.10724 1 4 e Uiso 0.087(3) H
H33 0.69667 0.95166 -0.12634 1 4 e Uiso 0.087(3) H
H34 0.69457 0.93299 0.12035 1 4 e Uiso 0.087(3) H
H35 0.68703 1.04925 0.12902 1 4 e Uiso 0.087(3) H
H36 1 1 0 0.5 2 a Uiso 0.087(3) H
H37 0.20985 0.42804 0.08795 1 4 e Uiso 0.167(5) H
H38 0.17038 0.426 -0.0963 1 4 e Uiso 0.167(5) H
H39 0.22857 0.18506 0.12071 1 4 e Uiso 0.167(5) H
H40 0.30256 0.17517 0.12268 1 4 e Uiso 0.167(5) H
H41 0.25502 0.18447 -0.18785 1 4 e Uiso 0.167(5) H
H42 0.1791 0.19683 -0.20364 1 4 e Uiso 0.167(5) H
H43 0.30557 0.42763 -0.09627 1 4 e Uiso 0.167(5) H
H44 0.33046 0.4284 0.08836 1 4 e Uiso 0.167(5) H
H45 0.11742 0.26317 -0.04311 1 4 e Uiso 0.167(5) H
H46 0.13831 0.30754 0.12726 1 4 e Uiso 0.167(5) H
H47 0.32605 0.31982 0.3175 1 4 e Uiso 0.167(5) H
H48 0.26525 0.27022 0.34743 1 4 e Uiso 0.167(5) H
H49 0.16682 0.34297 -0.378 1 4 e Uiso 0.167(5) H
H50 0.24114 0.32323 -0.36889 1 4 e Uiso 0.167(5) H
H51 0.39933 0.28189 0.10937 1 4 e Uiso 0.167(5) H
H52 0.37054 0.27199 -0.07522 1 4 e Uiso 0.167(5) H
H53 0.07132 0.43744 0.0281 1 4 e Uiso 0.167(5) H
H54 0.05075 0.39386 -0.14265 1 4 e Uiso 0.167(5) H
H55 0.32643 0.1144 0.38467 1 4 e Uiso 0.167(5) H
H56 0.38936 0.17583 0.38447 1 4 e Uiso 0.167(5) H
H57 0.14898 0.25322 -0.63008 1 4 e Uiso 0.167(5) H
H58 0.20326 0.17144 -0.53988 1 4 e Uiso 0.167(5) H
H59 0.42539 0.41426 -0.0843 1 4 e Uiso 0.167(5) H
H60 0.4576 0.41585 0.10105 1 4 e Uiso 0.167(5) H
H61 -0.02636 0.29544 -0.11189 1 4 e Uiso 0.167(5) H
H62 0.02704 0.2537 0.04589 1 4 e Uiso 0.167(5) H
H63 -0.01348 0.35032 0.04589 1 4 e Uiso 0.167(5) H
H64 0.35798 0.25211 0.62516 1 4 e Uiso 0.167(5) H
H65 0.363 0.13697 0.64797 1 4 e Uiso 0.167(5) H
H66 0.42561 0.19701 0.64797 1 4 e Uiso 0.167(5) H
H67 0.08001 0.128 -0.65277 1 4 e Uiso 0.167(5) H
H68 0.12769 0.07985 -0.49403 1 4 e Uiso 0.167(5) H
H69 0.08225 0.17079 -0.49403 1 4 e Uiso 0.167(5) H
H70 0.4954 0.27789 -0.09602 1 4 e Uiso 0.167(5) H
H71 0.54562 0.32287 0.06286 1 4 e Uiso 0.167(5) H
H72 0.49915 0.23324 0.06286 1 4 e Uiso 0.167(5) H
H73 0.5 1 0 0.5 2 d Uiso 0.167(5) H

####################################################################### 
# 
# 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_single_phase_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2060716'
loop_
_audit_author_name
_audit_author_address
'haneda tsuyoshi'
;asahi kasei corpration
Japan
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_GEOM001_single_phase        
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: powder data
;
_vrf_GEOM002_single_phase        
;
PROBLEM: _geom_bond_atom_site_label_2 is missing
RESPONSE: powder data
;
_vrf_GEOM003_single_phase        
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: powder data
;
_vrf_GEOM006_single_phase        
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: powder data
;
_vrf_GEOM007_single_phase        
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: powder data
;
_vrf_PLAT305_single_phase        
;
PROBLEM: Isolated Hydrogen Atom   (Outside Bond Range ??)        H58 Check
RESPONSE: powder data
;
_vrf_PLAT351_single_phase        
;
PROBLEM: Long   C-H (X0.96,N1.08A)  C14      - H55      .       1.28 Ang.
RESPONSE: powder data
;
_vrf_PLAT369_single_phase        
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C20      - C24      .       1.65 Ang.
RESPONSE: powder data
;
_vrf_PLAT411_single_phase        
;
PROBLEM: Short Inter H...H Contact  H57      ..H58      .       1.57 Ang.
RESPONSE: powder data
;
_vrf_PLAT334_single_phase        
;
PROBLEM: Small Aver. Benzene C-C Dist C18      -C20             1.33 Ang.
RESPONSE: powder data
;
_vrf_PLAT340_single_phase        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0405 Ang.
RESPONSE: powder data
;
_vrf_PLAT350_single_phase        
;
PROBLEM: Short  C-H (X0.96,N1.08A)  C7       - H40      .       0.75 Ang.
RESPONSE: powder data
;
_vrf_PLAT351_single_phase_2      
;
PROBLEM: Long   C-H (X0.96,N1.08A)  C11      - H49      .       1.17 Ang.
RESPONSE: powder data
;
_vrf_PLAT360_single_phase        
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C3       - C7       .       1.26 Ang.
RESPONSE: powder data
;
_vrf_PLAT369_single_phase_2      
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C19      - C22      .       1.57 Ang.
RESPONSE: powder data
;
_vrf_PLAT411_single_phase_2      
;
PROBLEM: Short Inter H...H Contact  H48      ..H58      .       1.86 Ang.
RESPONSE: powder data
;
# Added during the CSD deposition process: Wednesday 03 February 2021 06:55 AM
# end Validation Reply Form


# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            TBP
# Get _chemical_formula_moiety using checkCIF
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C48 H81 O8 P2'
_chemical_formula_weight         848.099
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0212 0.0130 'International Tables for Crystallography, Vol. C'
O O 0.0594 0.0453 'International Tables for Crystallography, Vol. C'
P P 0.3250 0.5665 'International Tables for Crystallography, Vol. C'
H H -0.0006 0.0000 'International Tables for Crystallography, Vol. C'

#===============================================================================
# 6. POWDER SPECIMEN AND CRYSTAL DATA

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

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   13.8216(4)
_cell_length_b                   10.5310(3)
_cell_length_c                   9.5380(2)
_cell_angle_alpha                83.576(1)
_cell_angle_beta                 93.435(1)
_cell_angle_gamma                109.149(2)
_cell_volume                     1302.87(5)
# If checkCIF gives a different Z value, change both
# _chemical_formula_sum and _chemical_formula_weight.
_cell_formula_units_Z            1
_cell_measurement_temperature    300

_cell_special_details            ?

_exptl_crystal_density_diffrn    1.0809
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             463.00
_exptl_crystal_description       ?????

# The next three fields give the specimen dimensions in mm.  The equatorial
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              ? # perpendicular to
# equatorial plane

_pd_spec_size_equat              ? # parallel to
# scattering vector
# in transmission

_pd_spec_size_thick              ? # parallel to
# scattering vector
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
# This field should be
# used to give details of the
# container.
; ?
;
_pd_spec_mount_mode              transmission

_pd_spec_shape                   cylinder

_pd_char_particle_morphology     ?
_pd_char_colour                  ?

# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    1.628
# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record
# the powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      300
_diffrn_source                   'Synchrotron radiation'
_diffrn_source_type              'aichiSR BL5S2'
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  CCD
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             step # options are 'step', 'cont',
#' 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;

_diffrn_radiation_wavelength     1.770000
_diffrn_radiation_monochromator  ?

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        5501
_pd_meas_2theta_range_min        5.0000
_pd_meas_2theta_range_max        60.0000
_pd_meas_2theta_range_inc        0.0100

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

#===============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text.

_pd_calc_method                  'Rietveld Refinement'

_pd_proc_ls_profile_function     'split pseudo-Voigt function'
_pd_proc_ls_background_function  'Legendre polynomials'
_pd_proc_ls_pref_orient_corr     
; ?
;
# Replace '; ?' with the following four lines for the March-Dollase function:
#; $P_k = \sum_{j=1}^{m_k} \frac{1}{m_k}
#\left( r^2 \cos^2 \alpha_j +r^{-1}\ sin^2 \alpha_j \right)^{-3/2}$
#with a preferred-orientation vector, (hkl),
#and <i>r</i> = 1.0(0)

_pd_proc_ls_prof_R_factor        0.04788
_pd_proc_ls_prof_wR_factor       0.03793
_pd_proc_ls_prof_wR_expected     0.00875
_refine_ls_R_I_factor            0.06802
_refine_ls_R_Fsqd_factor         0.02811
_refine_ls_R_factor_all          0.02813

_refine_special_details          
; ?
;

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     1/yi
# The following line must be commented out in the absence of H atoms.
#_refine_ls_hydrogen_treatment       ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_number_constraints    69

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   4.3378

_refine_ls_restrained_S_all      ?
# The following item can be obtained by setting NPRINT at 2 in *.ins.
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         ?

_refine_diff_density_max         0.0
_refine_diff_density_min         0.0

# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.

_pd_proc_2theta_range_min        5.0000
_pd_proc_2theta_range_max        60.0000
_pd_proc_2theta_range_inc        0.0100
_pd_proc_wavelength              ?


# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting
# of one data block containing a single powder profile. The value of
# _pd_block_diffractogram_id is used to associate each refinement with
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?

# Give appropriate details in the next two text fields.

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

# The following items are used to identify the programs used.

_computing_data_collection       ?
_computing_cell_refinement       'RIETAN-FP (Izumi and Momma, 2007)'
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'RIETAN-FP (Izumi and Momma, 2007)'
_computing_molecular_graphics    'VESTA (Momma and Izumi, 2008)'
_computing_publication_material  ?

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_type_symbol
P1 0.7924(9) 0.185(1) 0.184(1) 1 2 i Uiso 0.152(3) P
C2 0.789(2) 0.119(3) 0.359(3) 1 2 i Uiso 0.152(3) C
C3 0.916(2) 0.218(3) 0.101(2) 1 2 i Uiso 0.152(3) C
C4 0.780(2) 0.336(3) 0.200(2) 1 2 i Uiso 0.152(3) C
C5 0.688(2) 0.087(3) 0.071(3) 1 2 i Uiso 0.152(3) C
C6 0.828(2) 0.005(3) 0.398(2) 1 2 i Uiso 0.152(3) C
C7 0.915(2) 0.242(3) -0.031(2) 1 2 i Uiso 0.152(3) C
C8 0.684(2) 0.354(2) 0.241(3) 1 2 i Uiso 0.152(3) C
C9 0.707(2) -0.020(2) 0.040(3) 1 2 i Uiso 0.152(3) C
C10 0.843(2) -0.010(2) 0.580(2) 1 2 i Uiso 0.152(3) C
C11 1.026(2) 0.291(2) -0.112(3) 1 2 i Uiso 0.152(3) C
C12 0.703(2) 0.499(3) 0.272(3) 1 2 i Uiso 0.152(3) C
C13 0.629(2) -0.078(2) -0.085(3) 1 2 i Uiso 0.152(3) C
C14 0.806(2) -0.162(2) 0.583(2) 1 2 i Uiso 0.152(3) C
C15 1.070(2) 0.198(2) -0.114(3) 1 2 i Uiso 0.152(3) C
C16 0.615(2) 0.499(3) 0.321(2) 1 2 i Uiso 0.152(3) C
C17 0.617(2) -0.202(3) -0.110(2) 1 2 i Uiso 0.152(3) C
C18 0.710(3) 0.314(4) 0.664(2) 1 2 i Uiso 0.075(2) C
C19 0.617(2) 0.269(3) 0.706(4) 1 2 i Uiso 0.075(2) C
C20 0.779(2) 0.436(4) 0.711(3) 1 2 i Uiso 0.075(2) C
C21 0.589(2) 0.340(3) 0.812(4) 1 2 i Uiso 0.075(2) C
C22 0.543(2) 0.143(3) 0.637(2) 1 2 i Uiso 0.075(2) C
C23 0.754(3) 0.499(2) 0.788(3) 1 2 i Uiso 0.075(2) C
C24 0.892(2) 0.495(2) 0.638(2) 1 2 i Uiso 0.075(2) C
C25 0.648(3) 0.452(3) 0.853(2) 1 2 i Uiso 0.075(2) C
O26 0.450(1) 0.113(2) 0.687(1) 1 2 i Uiso 0.075(2) O
O27 0.565(1) 0.091(1) 0.541(1) 1 2 i Uiso 0.075(2) O
O28 0.956(1) 0.585(1) 0.720(1) 1 2 i Uiso 0.075(2) O
O29 0.915(1) 0.435(1) 0.546(1) 1 2 i Uiso 0.075(2) O
H30 0.80663 0.16206 0.4374 1 2 i Uiso 0.182(3) H
H31 0.71002 0.04461 0.38773 1 2 i Uiso 0.182(3) H
H32 0.97035 0.26427 0.16535 1 2 i Uiso 0.182(3) H
H33 0.92597 0.11794 0.11353 1 2 i Uiso 0.182(3) H
H34 0.83438 0.37967 0.2741 1 2 i Uiso 0.182(3) H
H35 0.79865 0.38964 0.11348 1 2 i Uiso 0.182(3) H
H36 0.62835 0.08043 0.12665 1 2 i Uiso 0.182(3) H
H37 0.69363 0.15408 -0.00747 1 2 i Uiso 0.182(3) H
H38 0.79974 -0.06768 0.34043 1 2 i Uiso 0.182(3) H
H39 0.90203 0.05602 0.3507 1 2 i Uiso 0.182(3) H
H40 0.87695 0.20155 -0.08252 1 2 i Uiso 0.182(3) H
H41 0.92097 0.34791 -0.03072 1 2 i Uiso 0.182(3) H
H42 0.63015 0.32902 0.17195 1 2 i Uiso 0.182(3) H
H43 0.65473 0.28595 0.33105 1 2 i Uiso 0.182(3) H
H44 0.77441 -0.00814 0.03095 1 2 i Uiso 0.182(3) H
H45 0.68535 -0.08756 0.13631 1 2 i Uiso 0.182(3) H
H46 0.90287 0.02264 0.61184 1 2 i Uiso 0.182(3) H
H47 0.78299 -0.00706 0.61549 1 2 i Uiso 0.182(3) H
H48 1.03485 0.37291 -0.15228 1 2 i Uiso 0.182(3) H
H49 1.07554 0.31467 -0.0089 1 2 i Uiso 0.182(3) H
H50 0.75451 0.5197 0.35197 1 2 i Uiso 0.182(3) H
H51 0.71148 0.55561 0.20039 1 2 i Uiso 0.182(3) H
H52 0.55663 -0.0824 -0.05902 1 2 i Uiso 0.182(3) H
H53 0.64755 -0.01051 -0.16386 1 2 i Uiso 0.182(3) H
H54 0.757 -0.19694 0.50654 1 2 i Uiso 0.182(3) H
H55 0.87565 -0.16754 0.50293 1 2 i Uiso 0.182(3) H
H56 0.8198 -0.20656 0.64746 1 2 i Uiso 0.182(3) H
H57 1.00149 0.10075 -0.13849 1 2 i Uiso 0.182(3) H
H58 1.00211 0.22147 -0.25105 1 2 i Uiso 0.182(3) H
H59 1.10551 0.199 -0.19871 1 2 i Uiso 0.182(3) H
H60 0.55862 0.49178 0.28257 1 2 i Uiso 0.182(3) H
H61 0.60121 0.45625 0.43258 1 2 i Uiso 0.182(3) H
H62 0.63467 0.60635 0.36486 1 2 i Uiso 0.182(3) H
H63 0.69798 -0.18372 -0.12867 1 2 i Uiso 0.182(3) H
H64 0.608 -0.25486 -0.02491 1 2 i Uiso 0.182(3) H
H65 0.58418 -0.22269 -0.18521 1 2 i Uiso 0.182(3) H
H66 0.74123 0.28386 0.57958 1 2 i Uiso 0.090(2) H
H67 0.51397 0.29532 0.83245 1 2 i Uiso 0.090(2) H
H68 0.80236 0.57788 0.81914 1 2 i Uiso 0.090(2) H
H69 0.62724 0.49268 0.92125 1 2 i Uiso 0.090(2) H
H70 1 0.5 0.5 0.5 1 e Uiso 0.090(2) H
H71 0.5 0 0.5 0.5 1 f Uiso 0.090(2) H

####################################################################### 
# 
# 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_single_phase_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2060717'
loop_
_audit_author_name
_audit_author_address
'tsuyoshi haneda'
;ASAHI KASEI Corp
Japan
;
_audit_update_record             
;
2021-08-29 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_GEOM006_single_phase        
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: powder data
;
_vrf_GEOM007_single_phase        
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: powder data
;
_vrf_PLAT721_single_phase        
;
PROBLEM: Bond    Calc     1.18(2), Rep     1.21080 Dev...       0.03 Ang.
RESPONSE: powder data
;
_vrf_PLAT340_single_phase        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02667 Ang.
RESPONSE: powder data
;
_vrf_PLAT721_single_phase_2      
;
PROBLEM: Bond    Calc   2.720(15), Rep     2.69150 Dev...       0.03 Ang.
RESPONSE: powder data
;
# Added during the CSD deposition process: Sunday 29 August 2021 05:52 AM
# end Validation Reply Form


# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            BTB-Pyram
# Get _chemical_formula_moiety using checkCIF
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C21 O4 P'
_chemical_formula_weight         347.196
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and
# natural products

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0021 'International Tables for Crystallography, Vol. C'
O O 0.0087 0.0080 'International Tables for Crystallography, Vol. C'
P P 0.1044 0.1225 'International Tables for Crystallography, Vol. C'

#===============================================================================
# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'C c c a'
_space_group_name_Hall           '-C 2b 2bc'
_space_group_IT_number           68

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,-y,z
3 -x,y,-z+1/2
4 x+1/2,-y,-z+1/2
5 -x,-y,-z
6 x+1/2,y,-z
7 x,-y,z+1/2
8 -x+1/2,y,z+1/2
9 x+1/2,y+1/2,z
10 -x,-y+1/2,z
11 -x+1/2,y+1/2,-z+1/2
12 x,-y+1/2,-z+1/2
13 -x+1/2,-y+1/2,-z
14 x,y+1/2,-z
15 x+1/2,-y+1/2,z+1/2
16 -x,y+1/2,z+1/2

_cell_length_a                   19.5817(2)
_cell_length_b                   19.58544(6)
_cell_length_c                   12.02036(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4610.02(5)
# If checkCIF gives a different Z value, change both
# _chemical_formula_sum and _chemical_formula_weight.
_cell_formula_units_Z            8
_cell_measurement_temperature    300

_cell_special_details            ?

_exptl_crystal_density_diffrn    1.0005
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384.00

# The next three fields give the specimen dimensions in mm.  The equatorial
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              ? # perpendicular to
# equatorial plane

_pd_spec_size_equat              ? # parallel to
# scattering vector
# in transmission

_pd_spec_size_thick              ? # parallel to
# scattering vector
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
# This field should be
# used to give details of the
# container.
; ?
;
_pd_spec_mount_mode              transmission

_pd_spec_shape                   cylinder

_pd_char_particle_morphology     ?
_pd_char_colour                  ?

# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    0.187
# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record
# the powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      300
_diffrn_source                   'Synchrotron radiation'
_diffrn_source_type              'SPring-8 BL19B2'
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  IP
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             step # options are 'step', 'cont',
#' 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;

_diffrn_radiation_wavelength     0.800000
_diffrn_radiation_monochromator  ?

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        6584
_pd_meas_2theta_range_min        2.0850
_pd_meas_2theta_range_max        35.0000
_pd_meas_2theta_range_inc        0.0050

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

#===============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text.

_pd_calc_method                  'Rietveld Refinement'

_pd_proc_ls_profile_function     'split pseudo-Voigt function'
_pd_proc_ls_background_function  'Legendre polynomials'
_pd_proc_ls_pref_orient_corr     
; ?
;
# Replace '; ?' with the following four lines for the March-Dollase function:
#; $P_k = \sum_{j=1}^{m_k} \frac{1}{m_k}
#\left( r^2 \cos^2 \alpha_j +r^{-1}\ sin^2 \alpha_j \right)^{-3/2}$
#with a preferred-orientation vector, (hkl),
#and <i>r</i> = 1.0(0)

_pd_proc_ls_prof_R_factor        0.07507
_pd_proc_ls_prof_wR_factor       0.08895
_pd_proc_ls_prof_wR_expected     0.18146
_refine_ls_R_I_factor            0.14659
_refine_ls_R_Fsqd_factor         0.12329
_refine_ls_R_factor_all          0.12309

_refine_special_details          
; ?
;

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     1/yi
# The following line must be commented out in the absence of H atoms.
#_refine_ls_hydrogen_treatment       ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     54
_refine_ls_number_restraints     43
_refine_ls_number_constraints    12

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   0.4902

_refine_ls_restrained_S_all      ?
# The following item can be obtained by setting NPRINT at 2 in *.ins.
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         ?

_refine_diff_density_max         0.0
_refine_diff_density_min         0.0

# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.

_pd_proc_2theta_range_min        2.0850
_pd_proc_2theta_range_max        35.0000
_pd_proc_2theta_range_inc        0.0050
_pd_proc_wavelength              ?


# Each refinement must be accompanied by a listing of the powder data
# in CIF format. Each listing should be sent as a separate file consisting
# of one data block containing a single powder profile. The value of
# _pd_block_diffractogram_id is used to associate each refinement with
# its corresponding powder profile, since it must match the value
# of _pd_block_id in the file containing the powder data. A template
# for supplying powder data in CIF format is available by ftp at
# ftp://ftp.iucr.org/pub/rietdataform.cif and an example is given
# at ftp://ftp.iucr.org/pub/rietdataxmpl.cif.

_pd_block_diffractogram_id       ?

# Give appropriate details in the next two text fields.

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

# The following items are used to identify the programs used.

_computing_data_collection       ?
_computing_cell_refinement       'RIETAN-FP (Izumi and Momma, 2007)'
_computing_data_reduction        ?
_computing_structure_solution    DASH
_computing_structure_refinement  'RIETAN-FP (Izumi and Momma, 2007)'
_computing_molecular_graphics    'VESTA (Momma and Izumi, 2008)'
_computing_publication_material  ?

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_type_symbol
C1 0.412(1) 0.124(1) 0.251(2) 1 16 i Uiso 0.131(3) C
C2 0.4660(8) 0.188(1) 0.248(4) 1 16 i Uiso 0.131(3) C
O3 0.3533(6) 0.1364(5) 0.241(1) 1 16 i Uiso 0.131(3) O
O4 0.4415(5) 0.0576(6) 0.257(1) 1 16 i Uiso 0.131(3) O
C5 0.433(1) 0.25 0.25 1 8 e Uiso 0.131(3) C
P6 0.25 0.5 -0.004(2) 1 8 h Uiso 0.090(2) P
C7 0.220(1) 0.567(1) -0.090(2) 1 16 i Uiso 0.090(2) C
C8 0.320(1) 0.526(1) 0.089(2) 1 16 i Uiso 0.090(2) C
C9 0.196(1) 0.627(1) -0.027(2) 1 16 i Uiso 0.090(2) C
C10 0.379(1) 0.562(1) 0.028(2) 1 16 i Uiso 0.090(2) C
C11 0.171(1) 0.691(1) -0.103(1) 1 16 i Uiso 0.090(2) C
C12 0.443(1) 0.582(1) 0.120(1) 1 16 i Uiso 0.090(2) C
C13 0.1395(8) 0.750(1) -0.027(1) 1 16 i Uiso 0.090(2) C
C14 0.4926(9) 0.6271(9) 0.079(1) 1 16 i Uiso 0.090(2) C

#===============================================================================

#10. GEOMETRICAL PARAMETERS

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.2108 . ?_??? ?
C1 O4 1.2746 . 1_555 ?
C1 C2 1.5472 . ?_??? ?
C1 C5 2.4535 . ?_??? ?
C1 C2 2.5673 . ?_??? ?
C1 C5 2.7196 . ?_??? ?
C1 O4 3.0838 . 3_655 ?
C1 C1 3.2987 . 3_655 ?
C1 C5 3.7574 . ?_??? ?
C2 C2 1.2761 . ?_??? ?
C2 C5 1.3871 . ?_??? ?
C2 C1 1.5472 . 1_555 ?
C2 C5 1.6311 . ?_??? ?
C2 C5 2.2427 . ?_??? ?
C2 O3 2.3813 . ?_??? ?
C2 C5 2.4077 . ?_??? ?
C2 O4 2.4223 . 1_555 ?
C2 C1 2.5673 . 3_655 ?
C2 C2 2.7688 . ?_??? ?
C2 O4 2.9873 . 3_655 ?
C2 C2 3.0429 . ?_??? ?
C2 O3 3.5851 . ?_??? ?
O3 C1 1.2108 . 1_555 ?
O3 O4 2.1858 . 1_555 ?
O3 C2 2.3813 . ?_??? ?
O3 C5 2.6915 . ?_??? ?
O3 C5 2.915 . ?_??? ?
O3 C9 3.5718 . ?_??? ?
O3 C2 3.5851 . ?_??? ?
O3 C8 3.5951 . ?_??? ?
O3 C7 3.6769 . ?_??? ?
O4 C1 1.2746 . 1_555 ?
O4 O3 2.1858 . ?_??? ?
O4 O4 2.3955 . 3_655 ?
O4 C2 2.4223 . ?_??? ?
O4 C12 2.7497 . ?_??? ?
O4 C2 2.9873 . ?_??? ?
O4 C1 3.0838 . 3_655 ?
O4 C8 3.3693 . ?_??? ?
O4 C10 3.4346 . ?_??? ?
O4 C5 3.6077 . ?_??? ?
C5 C5 0.2947 . ?_??? ?
C5 C2 1.3871 . ?_??? ?
C5 C2 1.6311 . ?_??? ?
C5 C2 2.2427 . ?_??? ?
C5 C2 2.4077 . ?_??? ?
C5 C1 2.4535 . 1_555 ?
C5 C5 2.4618 . ?_??? ?
C5 C5 2.4741 . ?_??? ?
C5 O3 2.6915 . ?_??? ?
C5 C1 2.7196 . 12_555 ?
C5 O3 2.915 . ?_??? ?
C5 O4 3.6077 . 1_555 ?
C5 C13 3.6342 . ?_??? ?
C5 C13 3.7116 . ?_??? ?
C5 C1 3.7574 . 3_655 ?
P6 P6 0.4979 . ?_??? ?
P6 C7 1.4222 . ?_??? ?
P6 C8 1.7595 . ?_??? ?
P6 C7 1.789 . ?_??? ?
P6 C8 1.7916 . ?_??? ?
P6 C9 2.3105 . ?_??? ?
P6 C10 2.7126 . ?_??? ?
P6 C9 2.8032 . ?_??? ?
P6 C10 2.8038 . ?_??? ?
P6 C11 3.6909 . ?_??? ?
C7 P6 1.4222 . ?_??? ?
C7 C9 1.5277 . ?_??? ?
C7 P6 1.789 . ?_??? ?
C7 C7 2.4789 . ?_??? ?
C7 C11 2.53 . ?_??? ?
C7 C8 2.7102 . ?_??? ?
C7 C8 2.9531 . ?_??? ?
C7 C10 3.238 . ?_??? ?
C7 C10 3.466 . ?_??? ?
C7 O3 3.6769 . ?_??? ?
C8 C10 1.5337 . ?_??? ?
C8 P6 1.7595 . ?_??? ?
C8 P6 1.7916 . ?_??? ?
C8 C12 2.5273 . ?_??? ?
C8 C8 2.591 . ?_??? ?
C8 C7 2.7102 . ?_??? ?
C8 C7 2.9531 . ?_??? ?
C8 C9 3.2083 . ?_??? ?
C8 C9 3.2289 . ?_??? ?
C8 O4 3.3693 . 12_555 ?
C8 O3 3.5951 . ?_??? ?
C9 C11 1.5197 . ?_??? ?
C9 C7 1.5277 . ?_??? ?
C9 P6 2.3105 . ?_??? ?
C9 C13 2.5209 . ?_??? ?
C9 P6 2.8032 . ?_??? ?
C9 C8 3.2083 . ?_??? ?
C9 C8 3.2289 . ?_??? ?
C9 O3 3.5718 . ?_??? ?
C9 C10 3.5954 . ?_??? ?
C10 C12 1.5139 . ?_??? ?
C10 C8 1.5337 . ?_??? ?
C10 C14 2.522 . ?_??? ?
C10 P6 2.7126 . ?_??? ?
C10 P6 2.8038 . ?_??? ?
C10 C7 3.238 . ?_??? ?
C10 O4 3.4346 . 12_555 ?
C10 C7 3.466 . ?_??? ?
C10 C9 3.5954 . ?_??? ?
C11 C13 1.5075 . ?_??? ?
C11 C9 1.5197 . ?_??? ?
C11 C7 2.53 . ?_??? ?
C11 P6 3.6909 . ?_??? ?
C12 C14 1.5128 . ?_??? ?
C12 C10 1.5139 . ?_??? ?
C12 C8 2.5273 . ?_??? ?
C12 O4 2.7497 . 12_555 ?
C12 C14 3.7679 . ?_??? ?
C13 C11 1.5075 . ?_??? ?
C13 C9 2.5209 . ?_??? ?
C13 C5 3.6342 . ?_??? ?
C13 C5 3.7116 . ?_??? ?
C14 C12 1.5128 . ?_??? ?
C14 C10 2.522 . ?_??? ?
C14 C12 3.7679 . ?_??? ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
? ? ? ? ? ? ? ?
####################################################################### 
# 
# 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_haneda_ad_auto
_database_code_depnum_ccdc_archive 'CCDC 2092705'
loop_
_audit_author_name
_audit_author_address
'tsuyoshi haneda'
;ASAHI KASEI Corp
Japan
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H36 P, C6 H9 O4'
_chemical_formula_sum            'C22 H45 O4 P'
_chemical_formula_weight         404.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P C22 H44 O4'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.3115(3)
_cell_length_b                   13.0344(4)
_cell_length_c                   19.6397(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.560(3)
_cell_angle_gamma                90
_cell_volume                     2382.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7896
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.8450
_cell_measurement_theta_min      2.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -16 12 0.0715
-13 -2 -2 0.0097
-4 4 26 0.1224
-1 16 -14 0.0470
8 -10 -17 0.0955
13 1 1 0.0710

_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.089
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.2563 -16.4485 12.0018 0.2224 0.9274 -0.3008
-13.0191 -1.5578 -1.9468 0.9518 -0.2283 0.2050
-3.8833 4.2453 25.8757 0.1069 0.4451 0.8891
-0.9658 15.9125 -13.6558 -0.2267 -0.9455 0.2338
7.9328 -9.9350 -16.6682 -0.2984 0.0714 -0.9518
13.0938 0.8724 0.8157 -0.9393 0.2252 -0.2590

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.780
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10259
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.928
_diffrn_reflns_theta_min         2.689
_diffrn_ambient_temperature      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  18.00   0.50    3.32    --    4.43 -67.00  -7.00  172
  2  ω    -17.00  27.00   0.50    3.32    --   -6.23 -99.00 -30.00   88
  3  ω    -18.00  23.00   0.50    3.32    --   -6.23 -99.00-180.00   82
  4  ω     -7.00  68.00   0.50    3.32    --    4.43  67.00 126.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0701487000
_diffrn_orient_matrix_UB_12      -0.0210319000
_diffrn_orient_matrix_UB_13      -0.0029471000
_diffrn_orient_matrix_UB_21      0.0179957000
_diffrn_orient_matrix_UB_22      -0.0361563000
_diffrn_orient_matrix_UB_23      0.0258339000
_diffrn_orient_matrix_UB_31      -0.0236625000
_diffrn_orient_matrix_UB_32      0.0347953000
_diffrn_orient_matrix_UB_33      0.0251000000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2644
_reflns_number_total             2953
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.054
_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)+(0.0400P)²+1.4477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C2(H2A,H2B), C1(H1A,H1B), C10(H10A,
 H10B), C6(H6A,H6B), C7(H7A,H7B)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.500000 0.45535(3) 0.750000 0.01520(10) Uani 1 2 d S T P . .
O2 O 0.99753(8) 0.26969(6) 0.68682(4) 0.02050(17) Uani 1 1 d . . . . .
O1 O 0.75950(8) 0.24197(5) 0.68281(4) 0.02102(17) Uani 1 1 d . . . . .
C11 C 0.87482(11) 0.25562(7) 0.65536(5) 0.01633(19) Uani 1 1 d . . . . .
C3 C 0.87658(11) 0.57962(8) 0.67438(5) 0.0197(2) Uani 1 1 d . . . . .
H3A H 0.831249 0.630799 0.643367 0.024 Uiso 1 1 calc R U . . .
H3B H 0.902331 0.614778 0.717698 0.024 Uiso 1 1 calc R U . . .
C5 C 0.43157(11) 0.37348(7) 0.68320(5) 0.0179(2) Uani 1 1 d . . . . .
H5A H 0.506487 0.322952 0.671686 0.022 Uiso 1 1 calc R U . . .
H5B H 0.347967 0.335026 0.699997 0.022 Uiso 1 1 calc R U . . .
C9 C 0.74192(11) 0.25212(8) 0.53859(5) 0.0205(2) Uani 1 1 d . . . . .
H9A H 0.685264 0.313666 0.550169 0.025 Uiso 1 1 calc R U . . .
H9B H 0.687592 0.191065 0.553263 0.025 Uiso 1 1 calc R U . . .
C2 C 0.76832(10) 0.49466(7) 0.68836(5) 0.0174(2) Uani 1 1 d . . . . .
H2A H 0.740438 0.459740 0.645232 0.021 Uiso 1 1 calc R U . . .
H2B H 0.812321 0.443206 0.719588 0.021 Uiso 1 1 calc R U . . .
C1 C 0.63593(10) 0.54092(7) 0.72035(5) 0.0183(2) Uani 1 1 d . . . . .
H1A H 0.590087 0.587586 0.686450 0.022 Uiso 1 1 calc R U . . .
H1B H 0.668918 0.583659 0.759404 0.022 Uiso 1 1 calc R U . . .
C10 C 0.88490(11) 0.25562(8) 0.57773(5) 0.0215(2) Uani 1 1 d . . . . .
H10A H 0.937137 0.318089 0.563944 0.026 Uiso 1 1 calc R U . . .
H10B H 0.942821 0.195666 0.564184 0.026 Uiso 1 1 calc R U . . .
C6 C 0.38570(11) 0.43193(8) 0.61857(5) 0.0217(2) Uani 1 1 d . . . . .
H6A H 0.319578 0.488091 0.630733 0.026 Uiso 1 1 calc R U . . .
H6B H 0.471463 0.463125 0.598220 0.026 Uiso 1 1 calc R U . . .
C4 C 1.01267(12) 0.53935(9) 0.64267(6) 0.0270(2) Uani 1 1 d . . . . .
H4A H 0.990126 0.514386 0.596539 0.040 Uiso 1 1 calc R U . . .
H4B H 1.051974 0.483004 0.670459 0.040 Uiso 1 1 calc R U . . .
H4C H 1.083624 0.594716 0.640570 0.040 Uiso 1 1 calc R U . . .
C7 C 0.31157(14) 0.36249(9) 0.56640(6) 0.0299(3) Uani 1 1 d . . . . .
H7A H 0.225617 0.331474 0.586678 0.036 Uiso 1 1 calc R U . . .
H7B H 0.377576 0.306210 0.554320 0.036 Uiso 1 1 calc R U . . .
C8 C 0.26656(17) 0.42061(12) 0.50220(7) 0.0441(3) Uani 1 1 d . . . . .
H8A H 0.214951 0.374197 0.470828 0.066 Uiso 1 1 calc R U . . .
H8B H 0.352077 0.447359 0.480241 0.066 Uiso 1 1 calc R U . . .
H8C H 0.203623 0.477737 0.514144 0.066 Uiso 1 1 calc R U . . .
H2 H 0.992(4) 0.272(2) 0.7270(13) 0.031(8) Uiso 0.5 1 d . . P . .


_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 C5 1.7946(10) . ?
P1 C5 1.7947(10) 2_656 ?
P1 C1 1.7959(10) 2_656 ?
P1 C1 1.7959(10) . ?
O2 C11 1.2972(12) . ?
O2 H2 0.79(3) . ?
O1 C11 1.2275(13) . ?
C11 C10 1.5300(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.5274(13) . ?
C3 C4 1.5206(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5311(14) . ?
C9 C9 1.5285(18) 7_656 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5198(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.5232(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5189(15) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5200(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C5 P1 C5 107.03(6) . 2_656 ?
C5 P1 C1 111.53(5) 2_656 . ?
C5 P1 C1 111.82(4) 2_656 2_656 ?
C5 P1 C1 111.81(4) . . ?
C5 P1 C1 111.53(5) . 2_656 ?
C1 P1 C1 103.21(6) . 2_656 ?
C11 O2 H2 114(2) . . ?
O2 C11 C10 113.42(9) . . ?
O1 C11 O2 125.53(9) . . ?
O1 C11 C10 121.05(9) . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C4 C3 C2 112.63(8) . . ?
P1 C5 H5A 108.9 . . ?
P1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 P1 113.31(7) . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C9 C9 H9A 108.9 7_656 . ?
C9 C9 H9B 108.9 7_656 . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C9 113.21(11) . 7_656 ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C1 C2 C3 109.43(8) . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
P1 C1 H1A 107.7 . . ?
P1 C1 H1B 107.7 . . ?
C2 C1 P1 118.25(7) . . ?
C2 C1 H1A 107.7 . . ?
C2 C1 H1B 107.7 . . ?
H1A C1 H1B 107.1 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 C11 115.29(9) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 111.97(9) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C6 C7 C8 111.88(10) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
P1 C5 C6 C7 -172.96(8) . . . . ?
O2 C11 C10 C9 -173.04(9) . . . . ?
O1 C11 C10 C9 7.84(14) . . . . ?
C3 C2 C1 P1 -173.59(7) . . . . ?
C5 P1 C5 C6 -172.97(9) 2_656 . . . ?
C5 P1 C1 C2 -57.65(9) . . . . ?
C5 P1 C1 C2 62.15(9) 2_656 . . . ?
C5 C6 C7 C8 -179.82(10) . . . . ?
C9 C9 C10 C11 -177.67(10) 7_656 . . . ?
C1 P1 C5 C6 64.44(8) 2_656 . . . ?
C1 P1 C5 C6 -50.56(8) . . . . ?
C1 P1 C1 C2 -177.65(9) 2_656 . . . ?
C4 C3 C2 C1 179.67(8) . . . . ?

_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.565
####################################################################### 
# 
# 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_han_pym-50
_database_code_depnum_ccdc_archive 'CCDC 2092707'
loop_
_audit_author_name
_audit_author_address
'tsuyoshi haneda'
;ASAHI KASEI Corp
Japan
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H36 P), C10 H4 O8'
_chemical_formula_sum            'C42 H76 O8 P2'
_chemical_formula_weight         770.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C42 H78 O8 P2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c e'
_space_group_name_Hall           '-C 2b 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
'-x, y+1/2, z-1/2'

_cell_length_a                   19.1921(7)
_cell_length_b                   20.0035(8)
_cell_length_c                   11.7616(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4515.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    223
_cell_measurement_theta_max      74.5440
_cell_measurement_theta_min      4.4230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 7 2 0.0206
-10 8 -1 0.0222
-8 -3 -5 0.0306
8 -10 -1 0.0513
6 6 6 0.0134
-1 1 -8 0.0107
-3 -4 7 0.0367

_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.8965 7.3496 1.6793 -0.1274 -0.5321 0.8371
-9.5346 8.1960 -0.9570 0.9168 -0.2199 -0.3334
-8.4733 -3.1333 -5.2796 0.1292 -0.0310 -0.9911
7.6524 -10.1675 -0.7581 -0.9720 0.2331 0.0281
6.4977 5.8676 5.5218 0.1290 -0.0309 0.9912
-0.6261 1.4405 -7.5760 -0.1665 -0.6938 -0.7006
-3.4411 -4.4531 6.8549 0.2181 0.9095 0.3540

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9289
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.063
_diffrn_reflns_theta_min         4.421
_diffrn_ambient_temperature      223
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  67.00   0.50   11.00    --   47.00 -71.00 -37.00  184
  2  ω   -106.00 -29.00   0.50   38.00    -- -102.00  96.00-171.00  154
  3  ω    -93.00 -29.00   0.50   38.00    -- -102.00  71.00  93.00  128
  4  ω    -69.00 -29.00   0.50   38.00    -- -102.00  59.00 -43.00   80
  5  ω     40.00  91.00   0.50   38.00    --  104.75 -71.00 -37.00  102
  6  ω    -12.00  14.00   0.50   11.00    --  -47.00  19.00-120.00   52
  7  ω   -109.00 -81.00   0.50   11.00    --  -47.00-125.00 120.00   56
  8  ω      2.00  27.00   0.50   11.00    --  -47.00  19.00  90.00   50
  9  ω    -63.00 -37.00   0.50   38.00    -- -102.00  61.00  60.00   52
 10  ω     32.00  74.00   0.50   38.00    --  104.75 -61.00 -90.00   84
 11  ω     32.00  57.00   0.50   38.00    --  104.75 -61.00  30.00   50
 12  ω    113.00 165.00   0.50   38.00    --  104.75  45.00-120.00  104
 13  ω     32.00  63.00   0.50   38.00    --  104.75 -61.00 150.00   62
 14  ω     37.00  65.00   0.50   38.00    --  104.75 -61.00 120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0564600000
_diffrn_orient_matrix_UB_12      0.0504090000
_diffrn_orient_matrix_UB_13      0.0362262000
_diffrn_orient_matrix_UB_21      -0.0297423000
_diffrn_orient_matrix_UB_22      -0.0515893000
_diffrn_orient_matrix_UB_23      0.0842296000
_diffrn_orient_matrix_UB_31      0.0487109000
_diffrn_orient_matrix_UB_32      0.0269201000
_diffrn_orient_matrix_UB_33      0.0935760000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1668
_reflns_number_total             2301
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.041
_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     122
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0507
_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)+(0.0698P)²+2.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C2(H2A,H2B), C6(H6A,H6B), C3(H3A,H3B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.750000 0.500000 0.49797(5) 0.0450(2) Uani 1 2 d S T P . .
O2 O 0.64886(13) 0.63886(13) 0.24312(17) 0.1107(8) Uani 1 1 d . . . . .
C1 C 0.68102(10) 0.47159(10) 0.40690(16) 0.0496(5) Uani 1 1 d . . . . .
H1A H 0.664895 0.509399 0.360906 0.060 Uiso 1 1 calc R U . . .
H1B H 0.699913 0.437955 0.354749 0.060 Uiso 1 1 calc R U . . .
C5 C 0.72135(10) 0.56647(10) 0.58865(16) 0.0517(5) Uani 1 1 d . . . . .
H5A H 0.683654 0.549581 0.636961 0.062 Uiso 1 1 calc R U . . .
H5B H 0.760028 0.579094 0.638635 0.062 Uiso 1 1 calc R U . . .
C9 C 0.56997(15) 0.750000 0.250000 0.0549(7) Uani 1 2 d S T P . .
H9 H 0.618951 0.750000 0.250003 0.066 Uiso 1 2 calc R U P . .
C10 C 0.53653(12) 0.68848(10) 0.24934(15) 0.0542(5) Uani 1 1 d . . . . .
C2 C 0.61852(10) 0.44156(11) 0.46844(18) 0.0563(5) Uani 1 1 d . . . . .
H2A H 0.633913 0.403212 0.513812 0.068 Uiso 1 1 calc R U . . .
H2B H 0.598965 0.474894 0.520495 0.068 Uiso 1 1 calc R U . . .
C6 C 0.69560(11) 0.62901(11) 0.52774(18) 0.0570(5) Uani 1 1 d . . . . .
H6A H 0.731012 0.643688 0.473147 0.068 Uiso 1 1 calc R U . . .
H6B H 0.653170 0.618227 0.485160 0.068 Uiso 1 1 calc R U . . .
O1 O 0.56179(17) 0.56990(10) 0.2489(3) 0.1359(11) Uani 1 1 d . . . . .
H1 H 0.519297 0.572305 0.261371 0.204 Uiso 0.5 1 calc R U P . .
C3 C 0.56257(11) 0.41910(12) 0.3862(2) 0.0662(6) Uani 1 1 d . . . . .
H3A H 0.546483 0.457782 0.342301 0.079 Uiso 1 1 calc R U . . .
H3B H 0.582705 0.386877 0.332699 0.079 Uiso 1 1 calc R U . . .
C7 C 0.68029(12) 0.68549(12) 0.6099(2) 0.0691(6) Uani 1 1 d . . . . .
H7A H 0.648343 0.669347 0.668841 0.083 Uiso 1 1 calc R U . . .
H7B H 0.723715 0.698999 0.647272 0.083 Uiso 1 1 calc R U . . .
C11 C 0.58801(19) 0.62889(15) 0.24814(19) 0.0817(8) Uani 1 1 d . . . . .
C4 C 0.50104(13) 0.38742(17) 0.4447(3) 0.0903(9) Uani 1 1 d . . . . .
H4A H 0.467102 0.373622 0.388295 0.136 Uiso 1 1 calc R U . . .
H4B H 0.479916 0.419535 0.496012 0.136 Uiso 1 1 calc R U . . .
H4C H 0.516490 0.348723 0.487541 0.136 Uiso 1 1 calc R U . . .
C8 C 0.64838(17) 0.74563(13) 0.5521(3) 0.0891(9) Uani 1 1 d . . . . .
H8A H 0.678748 0.760571 0.491305 0.134 Uiso 1 1 calc R U . . .
H8B H 0.642585 0.781366 0.607083 0.134 Uiso 1 1 calc R U . . .
H8C H 0.603316 0.733565 0.520930 0.134 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 1.7953(18) . ?
P1 C1 1.7953(18) 2_665 ?
P1 C5 1.7910(19) 2_665 ?
P1 C5 1.7909(19) . ?
O2 C11 1.186(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 C2 1.524(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C6 1.524(3) . ?
C9 H9 0.9400 . ?
C9 C10 1.388(3) 8_465 ?
C9 C10 1.388(3) . ?
C10 C10 1.402(4) 3_655 ?
C10 C11 1.548(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.514(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 C7 1.516(3) . ?
O1 H1 0.8300 . ?
O1 C11 1.283(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.507(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 C8 1.512(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C1 106.74(13) 2_665 . ?
C5 P1 C1 111.34(9) . . ?
C5 P1 C1 110.28(9) . 2_665 ?
C5 P1 C1 111.34(9) 2_665 2_665 ?
C5 P1 C1 110.28(9) 2_665 . ?
C5 P1 C5 106.90(13) . 2_665 ?
P1 C1 H1A 108.5 . . ?
P1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 P1 114.95(13) . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
P1 C5 H5A 108.4 . . ?
P1 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 P1 115.41(13) . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C10 C9 H9 117.5 8_465 . ?
C10 C9 H9 117.5 . . ?
C10 C9 C10 124.9(3) . 8_465 ?
C9 C10 C10 117.54(14) . 3_655 ?
C9 C10 C11 112.8(2) . . ?
C10 C10 C11 129.66(16) 3_655 . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 111.82(17) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 112.02(18) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C11 O1 H1 109.5 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.9(2) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.6(2) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O2 C11 C10 120.0(3) . . ?
O2 C11 O1 122.8(3) . . ?
O1 C11 C10 117.2(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
P1 C1 C2 C3 179.75(15) . . . . ?
P1 C5 C6 C7 -173.39(15) . . . . ?
C1 P1 C1 C2 176.73(19) 2_665 . . . ?
C1 P1 C5 C6 -60.38(17) . . . . ?
C1 P1 C5 C6 57.92(17) 2_665 . . . ?
C1 C2 C3 C4 178.4(2) . . . . ?
C5 P1 C1 C2 55.64(17) 2_665 . . . ?
C5 P1 C1 C2 -62.86(17) . . . . ?
C5 P1 C5 C6 179.11(18) 2_665 . . . ?
C5 C6 C7 C8 -174.6(2) . . . . ?
C9 C10 C11 O2 -3.1(3) . . . . ?
C9 C10 C11 O1 179.2(2) . . . . ?
C10 C9 C10 C10 -0.71(17) 8_465 . . 3_655 ?
C10 C9 C10 C11 179.73(17) 8_465 . . . ?
C10 C10 C11 O2 177.4(3) 3_655 . . . ?
C10 C10 C11 O1 -0.3(4) 3_655 . . . ?

_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.620
####################################################################### 
# 
# 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_haneda_ipa_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2092706'
loop_
_audit_author_name
_audit_author_address
'tsuyoshi haneda'
;ASAHI KASEI Corp
Japan
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H36 P, C8 H5 O4'
_chemical_formula_sum            'C24 H41 O4 P'
_chemical_formula_weight         424.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P C24 H40 O4'
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      triclinic
_space_group_IT_number           2
_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                   9.5325(4)
_cell_length_b                   10.0097(3)
_cell_length_c                   13.4783(4)
_cell_angle_alpha                74.634(3)
_cell_angle_beta                 87.007(3)
_cell_angle_gamma                81.876(3)
_cell_volume                     1227.50(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24669
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.1710
_cell_measurement_theta_min      2.6290
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 17 0.0554
0 -9 10 0.0634
13 3 8 0.0963
-13 -3 -8 0.0914
1 10 -9 0.0945
5 -11 -10 0.0667
1 1 -18 0.0959
-5 12 8 0.0306

_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1177 -2.5574 17.1070 0.1215 0.5078 0.8528
0.3631 -9.4828 10.0303 -0.1544 0.0368 0.9873
12.5236 2.9317 7.8008 0.8982 -0.2155 0.3832
-12.5802 -3.1708 -7.6046 -0.9065 0.2174 -0.3619
1.0953 10.0214 -9.3239 0.2628 -0.0628 -0.9628
4.6939 -11.4397 -10.3838 -0.2185 -0.9108 0.3502
0.8120 0.7540 -17.9842 -0.1493 -0.6236 -0.7673
-4.7600 12.0921 7.6204 0.2015 0.8399 -0.5039

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            57391
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.972
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_temperature      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  32.00   0.50    4.50    --   10.39 -55.00 178.00  190
  2  ω    -34.00  62.00   0.50    4.50    --  -11.95  55.00 -38.00  192
  3  ω    -86.00  10.00   0.50    4.50    --  -11.95 -55.00 178.00  192
  4  ω    -69.00  19.00   0.50    4.50    --   10.39 -19.00  90.00  176
  5  ω    -11.00  85.00   0.50    4.50    --   10.39  57.00-120.00  192
  6  ω    -11.00  85.00   0.50    4.50    --   10.39  55.00 -38.00  192
  7  ω    -18.00  85.00   0.50    4.50    --   10.39  77.00  90.00  206
  8  ω    -51.00  26.00   0.50    4.50    --  -11.95  98.00-171.94  154
  9  ω    -51.00  26.00   0.50    4.50    --  -11.95  98.00-104.94  154
 10  ω    -58.00  -2.00   0.50    4.50    --  -11.95 110.00 -61.16  112
 11  ω    -18.00  28.00   0.50    4.50    --  -11.95 -99.00 -30.00   92
 12  ω    -61.00  -7.00   0.50    4.50    --  -11.95 115.00  52.88  108
 13  ω    -74.00 -21.00   0.50    4.50    --  -11.95 139.00  27.55  106
 14  ω    -18.00  28.00   0.50    4.50    --  -11.95 -99.00  30.00   92
 15  ω    -11.00  85.00   0.50    4.50    --   10.39  57.00  30.00  192
 16  ω    -18.00  28.00   0.50    4.50    --  -11.95 -99.00 150.00   92
 17  ω    -49.00  33.00   0.50    4.50    --  -11.95  94.00 -71.10  164
 18  ω    -62.00 -37.00   0.50    4.50    --  -11.95 118.00  40.95   50
 19  ω    -62.00  -8.00   0.50    4.50    --  -11.95 117.00-148.07  108
 20  ω    -61.00  -7.00   0.50    4.50    --  -11.95 116.00  59.31  108
 21  ω    -58.00  -2.00   0.50    4.50    --  -11.95 110.00 153.82  112
 22  ω    -67.00 -15.00   0.50    4.50    --  -11.95 127.00 -80.05  104
 23  ω    -55.00   2.00   0.50    4.50    --  -11.95 105.00  -8.49  114
 24  ω    -54.00   6.00   0.50    4.50    --  -11.95 103.00 122.66  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0567947000
_diffrn_orient_matrix_UB_12      0.0313457000
_diffrn_orient_matrix_UB_13      0.0121818000
_diffrn_orient_matrix_UB_21      -0.0453924000
_diffrn_orient_matrix_UB_22      0.0302306000
_diffrn_orient_matrix_UB_23      0.0338937000
_diffrn_orient_matrix_UB_31      0.0190961000
_diffrn_orient_matrix_UB_32      -0.0600039000
_diffrn_orient_matrix_UB_33      0.0410137000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5474
_reflns_number_total             7036
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.111
_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)+(0.0807P)²+1.4111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.1976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H3(0.5) H2(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C14(H14A,H14B), C13(H13A,H13B), C1(H1A,H1B), C7(H7A,
 H7B), C15(H15A,H15B), C9(H9A,H9B), C3(H3A,H3B), C2(H2A,H2B), C10(H10A,H10B),
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C21(H21), C20(H20)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C12(H12A,H12B,H12C)
3.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.29325(6) 0.34003(6) 0.79972(4) 0.02362(15) Uani 1 1 d . . . . .
O3 O 0.04520(18) 0.93901(18) 0.08681(12) 0.0341(4) Uani 1 1 d . . . . .
H3 H 0.000744 1.003982 0.042189 0.051 Uiso 0.5 1 calc R U P . .
O4 O 0.2327(2) 1.05421(19) 0.04128(13) 0.0394(4) Uani 1 1 d . . . . .
O2 O 0.04831(19) 0.58894(19) 0.42990(13) 0.0347(4) Uani 1 1 d . . . . .
O1 O 0.1999(2) 0.5987(2) 0.54726(14) 0.0459(5) Uani 1 1 d . . . . .
C24 C 0.1637(2) 0.9748(2) 0.10375(16) 0.0283(4) Uani 1 1 d . . . . .
C18 C 0.2108(2) 0.7549(2) 0.38205(15) 0.0248(4) Uani 1 1 d . . . . .
C22 C 0.2193(2) 0.9130(2) 0.21190(16) 0.0255(4) Uani 1 1 d . . . . .
C17 C 0.1598(2) 0.8052(2) 0.28214(15) 0.0245(4) Uani 1 1 d . . . . .
H17 H 0.084442 0.766140 0.261647 0.029 Uiso 1 1 calc R U . . .
C23 C 0.1498(2) 0.6383(2) 0.46090(16) 0.0289(4) Uani 1 1 d . . . . .
C6 C 0.4590(2) 0.5505(2) 0.70352(17) 0.0278(4) Uani 1 1 d . . . . .
H6A H 0.374074 0.620761 0.684992 0.033 Uiso 1 1 calc R U . . .
H6B H 0.487819 0.549536 0.773253 0.033 Uiso 1 1 calc R U . . .
C19 C 0.3203(2) 0.8130(2) 0.41157(17) 0.0280(4) Uani 1 1 d . . . . .
H19 H 0.354314 0.779560 0.479895 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4223(2) 0.4063(2) 0.70446(16) 0.0259(4) Uani 1 1 d . . . . .
H5A H 0.510331 0.338999 0.715705 0.031 Uiso 1 1 calc R U . . .
H5B H 0.386666 0.410807 0.635790 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2308(2) 0.1587(2) 0.68733(16) 0.0264(4) Uani 1 1 d . . . . .
H14A H 0.146260 0.226904 0.662394 0.032 Uiso 1 1 calc R U . . .
H14B H 0.310218 0.182984 0.638531 0.032 Uiso 1 1 calc R U . . .
C21 C 0.3307(2) 0.9677(2) 0.24255(18) 0.0291(4) Uani 1 1 d . . . . .
H21 H 0.373314 1.039109 0.194643 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2691(2) 0.1677(2) 0.79439(16) 0.0251(4) Uani 1 1 d . . . . .
H13A H 0.357540 0.103911 0.816454 0.030 Uiso 1 1 calc R U . . .
H13B H 0.193009 0.134799 0.843857 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3806(2) 0.9193(2) 0.34255(18) 0.0298(5) Uani 1 1 d . . . . .
H20 H 0.455361 0.958765 0.363395 0.036 Uiso 1 1 calc R U . . .
C1 C 0.3539(2) 0.3341(2) 0.92553(16) 0.0263(4) Uani 1 1 d . . . . .
H1A H 0.339804 0.430253 0.934243 0.032 Uiso 1 1 calc R U . . .
H1B H 0.293955 0.277866 0.977930 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5783(3) 0.5916(3) 0.62718(18) 0.0325(5) Uani 1 1 d . . . . .
H7A H 0.664364 0.523677 0.648032 0.039 Uiso 1 1 calc R U . . .
H7B H 0.551332 0.586909 0.558371 0.039 Uiso 1 1 calc R U . . .
C15 C 0.2004(3) 0.0118(2) 0.69073(18) 0.0318(5) Uani 1 1 d . . . . .
H15A H 0.287617 -0.054840 0.710657 0.038 Uiso 1 1 calc R U . . .
H15B H 0.127037 -0.015140 0.744313 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1298(2) 0.4564(2) 0.77643(16) 0.0284(4) Uani 1 1 d . . . . .
H9A H 0.151590 0.553635 0.761769 0.034 Uiso 1 1 calc R U . . .
H9B H 0.086768 0.446182 0.714018 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5544(3) 0.2854(3) 1.05054(18) 0.0314(5) Uani 1 1 d . . . . .
H3A H 0.525645 0.382543 1.055158 0.038 Uiso 1 1 calc R U . . .
H3B H 0.503534 0.223237 1.105917 0.038 Uiso 1 1 calc R U . . .
C2 C 0.5094(2) 0.2729(3) 0.94657(17) 0.0303(5) Uani 1 1 d . . . . .
H2A H 0.522795 0.173284 0.945861 0.036 Uiso 1 1 calc R U . . .
H2B H 0.570177 0.323161 0.891407 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0207(2) 0.4340(3) 0.86407(18) 0.0319(5) Uani 1 1 d . . . . .
H10A H 0.061961 0.444871 0.926935 0.038 Uiso 1 1 calc R U . . .
H10B H -0.003556 0.337620 0.878727 0.038 Uiso 1 1 calc R U . . .
C11 C -0.1142(3) 0.5387(3) 0.8368(2) 0.0397(6) Uani 1 1 d . . . . .
H11A H -0.154593 0.527309 0.773767 0.048 Uiso 1 1 calc R U . . .
H11B H -0.184878 0.516784 0.893227 0.048 Uiso 1 1 calc R U . . .
C4 C 0.7127(3) 0.2477(3) 1.0682(2) 0.0405(6) Uani 1 1 d . . . . .
H4A H 0.763910 0.309391 1.014167 0.061 Uiso 1 1 calc R U . . .
H4B H 0.741508 0.150386 1.066417 0.061 Uiso 1 1 calc R U . . .
H4C H 0.734889 0.258879 1.135510 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6122(3) 0.7375(3) 0.6200(2) 0.0437(6) Uani 1 1 d . . . . .
H8A H 0.697769 0.753971 0.577476 0.065 Uiso 1 1 calc R U . . .
H8B H 0.628129 0.746247 0.689159 0.065 Uiso 1 1 calc R U . . .
H8C H 0.532657 0.806528 0.588854 0.065 Uiso 1 1 calc R U . . .
C16 C 0.1502(4) -0.0004(3) 0.5889(2) 0.0449(6) Uani 1 1 d . . . . .
H16A H 0.223886 0.022302 0.535983 0.067 Uiso 1 1 calc R U . . .
H16B H 0.063445 0.064880 0.568774 0.067 Uiso 1 1 calc R U . . .
H16C H 0.130782 -0.096066 0.596075 0.067 Uiso 1 1 calc R U . . .
C12 C -0.0893(3) 0.6894(3) 0.8192(2) 0.0473(7) Uani 1 1 d . . . . .
H12A H -0.034358 0.717553 0.755361 0.071 Uiso 1 1 calc R U . . .
H12B H -0.036787 0.698810 0.877074 0.071 Uiso 1 1 calc R U . . .
H12C H -0.180660 0.749492 0.813835 0.071 Uiso 1 1 calc R U . . .
H2 H 0.006(6) 0.541(5) 0.483(4) 0.025(13) Uiso 0.5 1 d . . P . .


_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 C5 1.793(2) . ?
P1 C13 1.792(2) . ?
P1 C1 1.803(2) . ?
P1 C9 1.796(2) . ?
O3 H3 0.8400 . ?
O3 C24 1.281(3) . ?
O4 C24 1.228(3) . ?
O2 C23 1.282(3) . ?
O2 H2 0.86(5) . ?
O1 C23 1.225(3) . ?
C24 C22 1.516(3) . ?
C18 C17 1.394(3) . ?
C18 C23 1.516(3) . ?
C18 C19 1.387(3) . ?
C22 C17 1.399(3) . ?
C22 C21 1.389(3) . ?
C17 H17 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.530(3) . ?
C6 C7 1.518(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.535(3) . ?
C14 C15 1.527(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.390(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C20 H20 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.533(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.517(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.527(3) . ?
C3 C4 1.519(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.534(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.516(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C5 P1 C1 109.39(10) . . ?
C5 P1 C9 109.06(10) . . ?
C13 P1 C5 109.46(10) . . ?
C13 P1 C1 109.66(10) . . ?
C13 P1 C9 111.03(11) . . ?
C9 P1 C1 108.21(10) . . ?
C24 O3 H3 109.5 . . ?
C23 O2 H2 109(4) . . ?
O3 C24 C22 115.33(18) . . ?
O4 C24 O3 125.9(2) . . ?
O4 C24 C22 118.8(2) . . ?
C17 C18 C23 122.2(2) . . ?
C19 C18 C17 119.54(19) . . ?
C19 C18 C23 118.25(19) . . ?
C17 C22 C24 122.1(2) . . ?
C21 C22 C24 118.67(19) . . ?
C21 C22 C17 119.23(19) . . ?
C18 C17 C22 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C22 C17 H17 119.9 . . ?
O2 C23 C18 115.74(18) . . ?
O1 C23 O2 125.4(2) . . ?
O1 C23 C18 118.9(2) . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C7 C6 C5 111.29(18) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
P1 C5 H5A 108.5 . . ?
P1 C5 H5B 108.5 . . ?
C6 C5 P1 115.26(15) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
H14A C14 H14B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 C13 110.86(17) . . ?
C22 C21 H21 119.6 . . ?
C22 C21 C20 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
P1 C13 H13A 108.8 . . ?
P1 C13 H13B 108.8 . . ?
C14 C13 P1 113.92(14) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C19 C20 C21 119.5(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
P1 C1 H1A 108.5 . . ?
P1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 P1 115.09(15) . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.7(2) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 113.2(2) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
P1 C9 H9A 108.5 . . ?
P1 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 P1 115.29(15) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C4 C3 C2 113.4(2) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 C1 111.09(19) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.19(19) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.4(2) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
P1 C1 C2 C3 174.51(16) . . . . ?
P1 C9 C10 C11 179.74(18) . . . . ?
O3 C24 C22 C17 11.3(3) . . . . ?
O3 C24 C22 C21 -167.2(2) . . . . ?
O4 C24 C22 C17 -169.4(2) . . . . ?
O4 C24 C22 C21 12.1(3) . . . . ?
C24 C22 C17 C18 -177.6(2) . . . . ?
C24 C22 C21 C20 176.7(2) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C22 C21 C20 C19 1.4(3) . . . . ?
C17 C18 C23 O2 0.0(3) . . . . ?
C17 C18 C23 O1 179.7(2) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C17 C22 C21 C20 -1.8(3) . . . . ?
C23 C18 C17 C22 180.0(2) . . . . ?
C23 C18 C19 C20 179.6(2) . . . . ?
C19 C18 C17 C22 0.4(3) . . . . ?
C19 C18 C23 O2 179.5(2) . . . . ?
C19 C18 C23 O1 -0.7(3) . . . . ?
C5 P1 C13 C14 -54.61(18) . . . . ?
C5 P1 C1 C2 -45.35(19) . . . . ?
C5 P1 C9 C10 -166.35(17) . . . . ?
C5 C6 C7 C8 176.9(2) . . . . ?
C21 C22 C17 C18 0.9(3) . . . . ?
C13 P1 C5 C6 -177.21(15) . . . . ?
C13 P1 C1 C2 74.70(18) . . . . ?
C13 P1 C9 C10 73.0(2) . . . . ?
C13 C14 C15 C16 175.3(2) . . . . ?
C1 P1 C5 C6 -57.04(18) . . . . ?
C1 P1 C13 C14 -174.61(15) . . . . ?
C1 P1 C9 C10 -47.4(2) . . . . ?
C7 C6 C5 P1 174.85(16) . . . . ?
C15 C14 C13 P1 -175.44(15) . . . . ?
C9 P1 C5 C6 61.14(19) . . . . ?
C9 P1 C13 C14 65.85(18) . . . . ?
C9 P1 C1 C2 -164.04(16) . . . . ?
C9 C10 C11 C12 -62.5(3) . . . . ?
C4 C3 C2 C1 -170.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.735
####################################################################### 
# 
# 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_180309_try1_
_database_code_depnum_ccdc_archive 'CCDC 2060718'
loop_
_audit_author_name
_audit_author_address
'haneda tsuyoshi'
;asahi kasei corpration
Japan
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_180309_try1_        
;
PROBLEM: Short Inter D...A Contact  O2       ..O2       .       2.45 Ang.
RESPONSE: There is a hydrogen bonding between O2-O2. So that the distance is close.
;
# Added during the CSD deposition process: Wednesday 03 February 2021 06:55 AM
# end Validation Reply Form


_vrf_PLAT430_ALERT_2_A           
;
PROBLEM:Short Inter D...A Contact
RESPONSE: There is a hydrogen bonding between O2-O2. So that the distance is close.
;

_audit_creation_date             2021-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H20 P, C8 H5 O4'
_chemical_formula_sum            'C16 H25 O4 P'
_chemical_formula_weight         312.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.9106(5)
_cell_length_b                   14.2542(4)
_cell_length_c                   15.9668(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.032(7)
_cell_angle_gamma                90
_cell_volume                     3607.20(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12465
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.12
_cell_measurement_theta_min      4.17
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20100
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.159
_diffrn_reflns_theta_min         4.171
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2027
_reflns_number_total             3288
_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       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1066P)²+1.1713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C13(H13)
2.d Tetrahedral OH refined with riding coordinates:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P1 P 0.50008(4) 0.21804(5) 0.49978(3) 0.0720(3) Uani 1 1 d . . . . .
O2 O 0.53874(8) 0.49939(9) 0.43687(9) 0.0609(4) Uani 1 1 d . . . . .
O3 O 0.92622(8) 0.50016(9) 0.37654(9) 0.0644(4) Uani 1 1 d . . . . .
O4 O 0.92283(9) 0.49935(9) 0.23789(10) 0.0775(6) Uani 1 1 d . . . . .
H4 H 0.886424 0.498291 0.198228 0.093 Uiso 1 1 calc R . . . .
O5 O 0.66011(11) 0.49993(13) 0.51562(10) 0.1096(9) Uani 1 1 d . . . . .
C6 C 0.66344(10) 0.49937(11) 0.36778(11) 0.0446(4) Uani 1 1 d . . . . .
C7 C 0.75083(10) 0.49917(11) 0.37199(11) 0.0453(4) Uani 1 1 d . . . . .
H7 H 0.781907 0.498413 0.424109 0.054 Uiso 1 1 calc R . . . .
C8 C 0.79246(10) 0.50011(11) 0.29890(11) 0.0444(4) Uani 1 1 d . . . . .
C9 C 0.74580(12) 0.49967(12) 0.22143(12) 0.0547(5) Uani 1 1 d . . . . .
H9 H 0.773213 0.498988 0.172335 0.066 Uiso 1 1 calc R . . . .
C10 C 0.61986(11) 0.49797(13) 0.44799(12) 0.0545(5) Uani 1 1 d . . . . .
C11 C 0.88772(11) 0.49893(12) 0.30696(12) 0.0508(5) Uani 1 1 d . . . . .
C12 C 0.61783(11) 0.49935(12) 0.29000(12) 0.0575(6) Uani 1 1 d . . . . .
H12 H 0.559189 0.498729 0.286805 0.069 Uiso 1 1 calc R . . . .
C13 C 0.65843(13) 0.50026(13) 0.21687(12) 0.0641(6) Uani 1 1 d . . . . .
H13 H 0.627209 0.501263 0.164832 0.077 Uiso 1 1 calc R . . . .
C14 C 0.42303(14) 0.14502(19) 0.54312(15) 0.0793(7) Uani 1 1 d . . . . .
H14A H 0.397672 0.104536 0.499065 0.095 Uiso 1 1 calc R . . . .
H14B H 0.451413 0.105227 0.586038 0.095 Uiso 1 1 calc R . . . .
C15 C 0.57705(16) 0.14469(19) 0.45713(16) 0.0843(7) Uani 1 1 d . . . . .
H15A H 0.602226 0.104462 0.501476 0.101 Uiso 1 1 calc R . . . .
H15B H 0.548717 0.104655 0.414380 0.101 Uiso 1 1 calc R . . . .
C16 C 0.4485(2) 0.29241(18) 0.41896(18) 0.0926(9) Uani 1 1 d . . . . .
H16A H 0.409204 0.332936 0.444801 0.111 Uiso 1 1 calc R . . . .
H16B H 0.490911 0.332273 0.397055 0.111 Uiso 1 1 calc R . . . .
C17 C 0.5501(2) 0.29269(19) 0.57970(17) 0.0982(9) Uani 1 1 d . . . . .
H17A H 0.588358 0.334538 0.553800 0.118 Uiso 1 1 calc R . . . .
H17B H 0.507196 0.331085 0.602403 0.118 Uiso 1 1 calc R . . . .
C18 C 0.4015(2) 0.2423(2) 0.34630(19) 0.1192(13) Uani 1 1 d . . . . .
H18A H 0.376532 0.287535 0.307088 0.143 Uiso 1 1 calc R . . . .
H18B H 0.439900 0.203372 0.318792 0.143 Uiso 1 1 calc R . . . .
H18C H 0.357985 0.204037 0.366659 0.143 Uiso 1 1 calc R . . . .
C19 C 0.5992(2) 0.2419(2) 0.6519(2) 0.1204(13) Uani 1 1 d . . . . .
H19A H 0.623712 0.286939 0.691502 0.145 Uiso 1 1 calc R . . . .
H19B H 0.561746 0.201558 0.679265 0.145 Uiso 1 1 calc R . . . .
H19C H 0.643067 0.205017 0.630566 0.145 Uiso 1 1 calc R . . . .
C20 C 0.3530(2) 0.1991(3) 0.5817(3) 0.1263(13) Uani 1 1 d . . . . .
H20A H 0.314329 0.155525 0.603515 0.152 Uiso 1 1 calc R . . . .
H20B H 0.377198 0.238138 0.626502 0.152 Uiso 1 1 calc R . . . .
H20C H 0.323388 0.237446 0.539418 0.152 Uiso 1 1 calc R . . . .
C21 C 0.6483(2) 0.1989(3) 0.4179(3) 0.1348(14) Uani 1 1 d . . . . .
H21A H 0.686884 0.155042 0.396489 0.162 Uiso 1 1 calc R . . . .
H21B H 0.624249 0.237689 0.372834 0.162 Uiso 1 1 calc R . . . .
H21C H 0.677830 0.237496 0.460047 0.162 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C14 1.793(2) . ?
P1 C15 1.790(3) . ?
P1 C16 1.810(3) . ?
P1 C17 1.793(3) . ?
O2 C10 1.287(2) . ?
O3 C11 1.221(2) . ?
O4 H4 0.8200 . ?
O4 C11 1.279(2) . ?
O5 C10 1.206(3) . ?
C6 C7 1.386(2) . ?
C6 C10 1.509(2) . ?
C6 C12 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(2) . ?
C8 C9 1.386(3) . ?
C8 C11 1.510(2) . ?
C9 H9 0.9300 . ?
C9 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C20 1.529(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C21 1.548(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C18 1.505(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C19 1.518(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C14 P1 C16 109.45(13) . . ?
C14 P1 C17 110.23(14) . . ?
C15 P1 C14 108.76(14) . . ?
C15 P1 C16 110.69(14) . . ?
C15 P1 C17 109.96(14) . . ?
C17 P1 C16 107.75(15) . . ?
C11 O4 H4 109.5 . . ?
C7 C6 C10 119.50(17) . . ?
C12 C6 C7 119.27(16) . . ?
C12 C6 C10 121.23(15) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.56(17) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C11 118.45(16) . . ?
C9 C8 C7 119.43(16) . . ?
C9 C8 C11 122.09(15) . . ?
C8 C9 H9 119.9 . . ?
C13 C9 C8 120.23(16) . . ?
C13 C9 H9 119.9 . . ?
O2 C10 C6 114.35(17) . . ?
O5 C10 O2 124.76(17) . . ?
O5 C10 C6 120.80(16) . . ?
O3 C11 O4 124.21(16) . . ?
O3 C11 C8 119.82(16) . . ?
O4 C11 C8 115.94(17) . . ?
C6 C12 H12 119.6 . . ?
C6 C12 C13 120.74(17) . . ?
C13 C12 H12 119.6 . . ?
C9 C13 H13 120.1 . . ?
C12 C13 C9 119.75(18) . . ?
C12 C13 H13 120.1 . . ?
P1 C14 H14A 108.7 . . ?
P1 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C20 C14 P1 114.2(2) . . ?
C20 C14 H14A 108.7 . . ?
C20 C14 H14B 108.7 . . ?
P1 C15 H15A 108.7 . . ?
P1 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C21 C15 P1 114.3(2) . . ?
C21 C15 H15A 108.7 . . ?
C21 C15 H15B 108.7 . . ?
P1 C16 H16A 108.3 . . ?
P1 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C18 C16 P1 115.81(19) . . ?
C18 C16 H16A 108.3 . . ?
C18 C16 H16B 108.3 . . ?
P1 C17 H17A 108.5 . . ?
P1 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C17 P1 115.07(19) . . ?
C19 C17 H17A 108.5 . . ?
C19 C17 H17B 108.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C11 -179.43(15) . . . . ?
C6 C12 C13 C9 1.0(3) . . . . ?
C7 C6 C10 O2 179.23(16) . . . . ?
C7 C6 C10 O5 2.6(3) . . . . ?
C7 C6 C12 C13 -0.8(3) . . . . ?
C7 C8 C9 C13 1.3(3) . . . . ?
C7 C8 C11 O3 -2.3(3) . . . . ?
C7 C8 C11 O4 179.64(16) . . . . ?
C8 C9 C13 C12 -1.3(3) . . . . ?
C9 C8 C11 O3 179.38(17) . . . . ?
C9 C8 C11 O4 1.3(3) . . . . ?
C10 C6 C7 C8 179.77(15) . . . . ?
C10 C6 C12 C13 -179.74(17) . . . . ?
C11 C8 C9 C13 179.64(16) . . . . ?
C12 C6 C7 C8 0.8(3) . . . . ?
C12 C6 C10 O2 -1.8(3) . . . . ?
C12 C6 C10 O5 -178.47(19) . . . . ?
C14 P1 C15 C21 -179.6(2) . . . . ?
C14 P1 C16 C18 -59.3(3) . . . . ?
C14 P1 C17 C19 62.4(3) . . . . ?
C15 P1 C14 C20 -179.9(2) . . . . ?
C15 P1 C16 C18 60.6(3) . . . . ?
C15 P1 C17 C19 -57.5(3) . . . . ?
C16 P1 C14 C20 -58.8(3) . . . . ?
C16 P1 C15 C21 60.1(3) . . . . ?
C16 P1 C17 C19 -178.2(3) . . . . ?
C17 P1 C14 C20 59.5(2) . . . . ?
C17 P1 C15 C21 -58.8(3) . . . . ?
C17 P1 C16 C18 -179.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
