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

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

data_exp_9968
_database_code_depnum_ccdc_archive 'CCDC 1978107'
loop_
_audit_author_name
_audit_author_address
p
;Xinxiang Medical University
China
;
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_audit_creation_date             2019-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 O2 P'
_chemical_formula_sum            'C25 H27 O2 P'
_chemical_formula_weight         390.43
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4061(2)
_cell_length_b                   10.0093(2)
_cell_length_c                   20.3835(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.910(2)
_cell_angle_gamma                90
_cell_volume                     2122.83(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3397
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      64.5860
_cell_measurement_theta_min      4.2420
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    1.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7201
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        64.830
_diffrn_reflns_theta_max         64.830
_diffrn_reflns_theta_min         4.249
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  15.00   1.00    1.00    --  -41.13  37.00 -60.00   62
  2  ω    -65.00  38.00   1.00    1.00    --  -41.13  19.00  60.00  103
  3  ω     25.00 102.00   1.00    1.70    --   89.91 -61.00  30.00   77
  4  ω    120.00 146.00   1.00    1.70    --   89.91 112.00 111.00   26
  5  ω    100.00 150.00   1.00    1.70    --   89.91 125.00  30.00   50
  6  ω     95.00 162.00   1.00    1.70    --   89.91 125.00 -60.00   67
  7  ω     89.00 153.00   1.00    1.70    --   89.91  45.00-150.00   64
  8  ω     57.00 121.00   1.00    1.70    --   89.91 -77.00 -90.00   64
  9  ω     51.00 101.00   1.00    1.70    --   89.91-125.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0614793000
_diffrn_orient_matrix_UB_12      -0.1241735000
_diffrn_orient_matrix_UB_13      -0.0313808000
_diffrn_orient_matrix_UB_21      -0.0017993000
_diffrn_orient_matrix_UB_22      0.0705643000
_diffrn_orient_matrix_UB_23      -0.0671729000
_diffrn_orient_matrix_UB_31      0.1346710000
_diffrn_orient_matrix_UB_32      0.0573539000
_diffrn_orient_matrix_UB_33      0.0147625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3079
_reflns_number_total             3521
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.205
_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)+(0.0724P)²+1.1022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1344
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C2 \\sim O2A-C2A
 with sigma of 0.02
 O2-C1 \\sim O2A-C1A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C9-C8 \\sim C9-C8A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C8-C7 \\sim C8A-C7A
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C2-C7 \\sim C2A-C7A
 with sigma of 0.02
 O2-C3 \\sim O2A-C3A
 with sigma of 0.04
 O2-C7 \\sim O2A-C7A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C6-C2 \\sim C6A-C2A
 with sigma of 0.04
 C6-C4 \\sim C6A-C4A
 with sigma of 0.04
 C9-C7 \\sim C9-C7A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 C8-C2 \\sim C8A-C2A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.04
 C2-C1 \\sim C2A-C1A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C22 \\sim C23 \\sim C25 \\sim C24 \\sim C21 \\sim C20: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.003
Uanis(C6A) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(O2A)
\\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.01
4. Others
 Sof(O2A)=Sof(C6A)=Sof(H6A)=Sof(C3A)=Sof(H3A)=Sof(C8A)=Sof(H8A)=Sof(C5A)=
 Sof(H5A)=Sof(C2A)=Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(H1Ac)=Sof(C7A)=Sof(C4A)=
 Sof(H4A)=1-FVAR(1)
 Sof(O2)=Sof(C6)=Sof(H6)=Sof(C3)=Sof(H3)=Sof(C8)=Sof(H8)=Sof(C5)=Sof(H5)=
 Sof(C2)=Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(H1c)=Sof(C7)=Sof(C4)=Sof(H4)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C19(H19), C3(H3), C15(H15), C17(H17), C18(H18), C16(H16), C21(H21),
 C22(H22), C23(H23), C25(H25), C24(H24), C8(H8), C5(H5), C4(H4), C6A(H6A),
 C3A(H3A), C8A(H8A), C5A(H5A), C4A(H4A)
5.b Fitted hexagon refined as free rotating group:
 C21(C20,C22,C23,C25,C24)
5.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C13(H13a,H13b,H13c), C12(H12a,H12b,H12c), C1(H1a,H1b,
 H1c), C1A(H1Aa,H1Ab,H1Ac)
;
_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 0.72348(5) 0.13058(5) 0.65887(2) 0.01798(18) Uani 1 1 d . . . . .
O1 O 0.74504(15) -0.01188(15) 0.64220(8) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.6325(10) 0.3611(7) 0.4563(4) 0.0219(15) Uani 0.634(5) 1 d D U P A 1
C6 C 0.7107(14) 0.6037(13) 0.5820(6) 0.0188(18) Uani 0.634(5) 1 d D U P A 1
H6 H 0.7263 0.6052 0.6271 0.023 Uiso 0.634(5) 1 calc R . P A 1
C10 C 0.88355(19) 0.2200(2) 0.55405(10) 0.0206(4) Uani 1 1 d . . . . .
C14 C 0.5582(2) 0.1557(2) 0.68297(10) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.76046(19) 0.2468(2) 0.59329(10) 0.0225(5) Uani 1 1 d D . . . .
C11 C 0.9921(2) 0.1661(2) 0.59902(11) 0.0255(5) Uani 1 1 d . . . . .
H11A H 1.0139 0.2320 0.6316 0.038 Uiso 1 1 calc GR . . . .
H11B H 1.0663 0.1468 0.5733 0.038 Uiso 1 1 calc GR . . . .
H11C H 0.9638 0.0860 0.6203 0.038 Uiso 1 1 calc GR . . . .
C19 C 0.5191(2) 0.2496(2) 0.72890(11) 0.0280(5) Uani 1 1 d . . . . .
H19 H 0.5791 0.3075 0.7477 0.034 Uiso 1 1 calc R . . . .
C13 C 0.93593(19) 0.3457(2) 0.52119(10) 0.0228(5) Uani 1 1 d . . . . .
H13A H 0.8797 0.3713 0.4856 0.034 Uiso 1 1 calc GR . . . .
H13B H 1.0201 0.3279 0.5047 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.9408 0.4169 0.5527 0.034 Uiso 1 1 calc GR . . . .
C3 C 0.6609(16) 0.5974(11) 0.4450(6) 0.020(2) Uani 0.634(5) 1 d D . P A 1
H3 H 0.6462 0.5953 0.3999 0.024 Uiso 0.634(5) 1 calc R . P A 1
C15 C 0.4664(2) 0.0705(2) 0.65552(11) 0.0305(5) Uani 1 1 d . . . . .
H15 H 0.4909 0.0069 0.6249 0.037 Uiso 1 1 calc R . . . .
C17 C 0.3010(2) 0.1727(3) 0.71892(12) 0.0337(6) Uani 1 1 d . . . . .
H17 H 0.2153 0.1787 0.7308 0.040 Uiso 1 1 calc R . . . .
C12 C 0.8522(3) 0.1148(2) 0.50142(11) 0.0330(6) Uani 1 1 d . . . . .
H12A H 0.8263 0.0332 0.5222 0.049 Uiso 1 1 calc GR . . . .
H12B H 0.9270 0.0986 0.4756 0.049 Uiso 1 1 calc GR . . . .
H12C H 0.7836 0.1467 0.4735 0.049 Uiso 1 1 calc GR . . . .
C18 C 0.3911(2) 0.2575(3) 0.74687(12) 0.0376(6) Uani 1 1 d . . . . .
H18 H 0.3661 0.3201 0.7778 0.045 Uiso 1 1 calc R . . . .
C16 C 0.3383(2) 0.0794(3) 0.67344(12) 0.0356(6) Uani 1 1 d . . . . .
H16 H 0.2777 0.0221 0.6547 0.043 Uiso 1 1 calc R . . . .
C21 C 0.86621(16) 0.07997(13) 0.77032(7) 0.0384(5) Uani 1 1 d . U . . .
H21 H 0.8444 -0.0086 0.7619 0.046 Uiso 1 1 calc R . . . .
C20 C 0.82026(13) 0.18072(15) 0.72930(6) 0.0266(4) Uani 1 1 d G U . . .
C22 C 0.85286(15) 0.31305(13) 0.74185(7) 0.0357(5) Uani 1 1 d G U . . .
H22 H 0.8221 0.3805 0.7144 0.043 Uiso 1 1 calc R . . . .
C23 C 0.93143(16) 0.34462(15) 0.79541(8) 0.0504(6) Uani 1 1 d G U . . .
H23 H 0.9532 0.4332 0.8038 0.060 Uiso 1 1 calc R . . . .
C25 C 0.97739(15) 0.2439(2) 0.83643(7) 0.0553(6) Uani 1 1 d G U . . .
H25 H 1.0300 0.2650 0.8723 0.066 Uiso 1 1 calc R . . . .
C24 C 0.94478(16) 0.11155(18) 0.82389(7) 0.0547(6) Uani 1 1 d G U . . .
H24 H 0.9755 0.0441 0.8513 0.066 Uiso 1 1 calc R . . . .
C8 C 0.6833(4) 0.3596(4) 0.5908(2) 0.0185(9) Uani 0.634(5) 1 d D . P A 1
H8 H 0.6163 0.3583 0.6205 0.022 Uiso 0.634(5) 1 calc R . P A 1
C5 C 0.7102(5) 0.7248(5) 0.5448(2) 0.0231(10) Uani 0.634(5) 1 d D . P A 1
H5 H 0.7261 0.8061 0.5656 0.028 Uiso 0.634(5) 1 calc R . P A 1
C2 C 0.6590(3) 0.4815(5) 0.48207(19) 0.0204(11) Uani 0.634(5) 1 d D . P A 1
C1 C 0.6077(8) 0.3519(7) 0.3869(3) 0.0339(15) Uani 0.634(5) 1 d D . P A 1
H1A H 0.6815 0.3830 0.3636 0.051 Uiso 0.634(5) 1 calc GR . P A 1
H1B H 0.5346 0.4060 0.3753 0.051 Uiso 0.634(5) 1 calc GR . P A 1
H1C H 0.5906 0.2606 0.3752 0.051 Uiso 0.634(5) 1 calc GR . P A 1
C7 C 0.6873(3) 0.4829(4) 0.5496(2) 0.0167(9) Uani 0.634(5) 1 d D . P A 1
C4 C 0.6863(3) 0.7209(4) 0.47847(18) 0.0261(9) Uani 0.634(5) 1 d D . P A 1
H4 H 0.6865 0.8001 0.4546 0.031 Uiso 0.634(5) 1 calc R . P A 1
O2A O 0.7052(18) 0.5831(15) 0.5696(6) 0.029(4) Uani 0.366(5) 1 d D U P A 2
C6A C 0.623(3) 0.332(2) 0.4494(9) 0.024(4) Uani 0.366(5) 1 d D U P A 2
H6A H 0.6043 0.2415 0.4472 0.028 Uiso 0.366(5) 1 calc R . P A 2
C3A C 0.672(3) 0.618(2) 0.4576(9) 0.027(6) Uani 0.366(5) 1 d D U P A 2
H3A H 0.6865 0.7090 0.4610 0.033 Uiso 0.366(5) 1 calc R . P A 2
C8A C 0.6623(6) 0.3122(8) 0.5690(4) 0.0166(15) Uani 0.366(5) 1 d D . P A 2
H8A H 0.5865 0.3062 0.5924 0.020 Uiso 0.366(5) 1 calc R . P A 2
C5A C 0.6193(13) 0.4169(13) 0.3919(6) 0.052(4) Uani 0.366(5) 1 d D . P A 2
H5A H 0.6002 0.3793 0.3512 0.062 Uiso 0.366(5) 1 calc R . P A 2
C2A C 0.6769(6) 0.5321(7) 0.5111(5) 0.028(2) Uani 0.366(5) 1 d D . P A 2
C1A C 0.7143(10) 0.7238(10) 0.5791(6) 0.045(3) Uani 0.366(5) 1 d D . P A 2
H1AA H 0.7829 0.7586 0.5532 0.067 Uiso 0.366(5) 1 calc GR . P A 2
H1AB H 0.7314 0.7424 0.6246 0.067 Uiso 0.366(5) 1 calc GR . P A 2
H1AC H 0.6348 0.7652 0.5658 0.067 Uiso 0.366(5) 1 calc GR . P A 2
C7A C 0.6565(5) 0.3952(6) 0.5085(3) 0.0193(17) Uani 0.366(5) 1 d D . P A 2
C4A C 0.6433(6) 0.5517(9) 0.3961(5) 0.046(2) Uani 0.366(5) 1 d D . P A 2
H4A H 0.6407 0.6025 0.3579 0.055 Uiso 0.366(5) 1 calc R . P A 2


_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 O1 1.4838(16) . ?
P1 C14 1.814(2) . ?
P1 C9 1.818(2) . ?
P1 C20 1.8114(11) . ?
O2 C2 1.342(8) . ?
O2 C1 1.438(9) . ?
C6 H6 0.9300 . ?
C6 C5 1.430(14) . ?
C6 C7 1.397(12) . ?
C10 C9 1.544(3) . ?
C10 C11 1.541(3) . ?
C10 C13 1.530(3) . ?
C10 C12 1.535(3) . ?
C14 C19 1.392(3) . ?
C14 C15 1.392(3) . ?
C9 C8 1.386(5) . ?
C9 C8A 1.304(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C18 1.389(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.385(8) . ?
C3 C4 1.433(13) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C17 C16 1.376(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C21 C24 1.3900 . ?
C20 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C23 1.3900 . ?
C23 H23 0.9300 . ?
C23 C25 1.3900 . ?
C25 H25 0.9300 . ?
C25 C24 1.3900 . ?
C24 H24 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.495(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(6) . ?
C2 C7 1.403(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 0.9300 . ?
O2A C2A 1.325(13) . ?
O2A C1A 1.424(15) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.45(2) . ?
C6A C7A 1.399(18) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.387(12) . ?
C3A C4A 1.444(19) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.488(8) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.375(13) . ?
C2A C7A 1.387(9) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C4A H4A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C14 110.06(9) . . ?
O1 P1 C9 114.35(9) . . ?
O1 P1 C20 111.32(8) . . ?
C14 P1 C9 108.84(9) . . ?
C20 P1 C14 105.34(8) . . ?
C20 P1 C9 106.49(8) . . ?
C2 O2 C1 118.4(6) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C7 C6 C5 118.9(10) . . ?
C11 C10 C9 111.06(16) . . ?
C13 C10 C9 112.79(17) . . ?
C13 C10 C11 106.56(17) . . ?
C13 C10 C12 109.38(17) . . ?
C12 C10 C9 108.21(17) . . ?
C12 C10 C11 108.77(18) . . ?
C19 C14 P1 124.35(16) . . ?
C19 C14 C15 118.6(2) . . ?
C15 C14 P1 116.98(17) . . ?
C10 C9 P1 117.14(15) . . ?
C8 C9 P1 114.7(2) . . ?
C8 C9 C10 127.5(2) . . ?
C8A C9 P1 115.2(3) . . ?
C8A C9 C10 122.8(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.8 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(9) . . ?
C4 C3 H3 121.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(2) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C24 120.0 . . ?
C24 C21 H21 120.0 . . ?
C21 C20 P1 117.22(8) . . ?
C21 C20 C22 120.0 . . ?
C22 C20 P1 122.74(8) . . ?
C20 C22 H22 120.0 . . ?
C23 C22 C20 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C23 C22 120.0 . . ?
C25 C23 H23 120.0 . . ?
C23 C25 H25 120.0 . . ?
C23 C25 C24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C21 C24 H24 120.0 . . ?
C25 C24 C21 120.0 . . ?
C25 C24 H24 120.0 . . ?
C9 C8 H8 113.9 . . ?
C9 C8 C7 132.2(3) . . ?
C7 C8 H8 113.9 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(7) . . ?
C4 C5 H5 120.1 . . ?
O2 C2 C3 123.0(7) . . ?
O2 C2 C7 115.6(5) . . ?
C3 C2 C7 121.4(7) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C7 C8 117.0(7) . . ?
C6 C7 C2 120.4(7) . . ?
C2 C7 C8 122.4(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4 119.2 . . ?
C2A O2A C1A 121.1(12) . . ?
C5A C6A H6A 122.1 . . ?
C7A C6A H6A 122.1 . . ?
C7A C6A C5A 115.9(14) . . ?
C2A C3A H3A 123.0 . . ?
C2A C3A C4A 113.9(15) . . ?
C4A C3A H3A 123.0 . . ?
C9 C8A H8A 116.0 . . ?
C9 C8A C7A 128.0(5) . . ?
C7A C8A H8A 116.0 . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A C6A 121.5(12) . . ?
C4A C5A H5A 119.3 . . ?
O2A C2A C3A 118.3(13) . . ?
O2A C2A C7A 116.6(10) . . ?
C3A C2A C7A 125.1(12) . . ?
O2A C1A H1AA 109.5 . . ?
O2A C1A H1AB 109.5 . . ?
O2A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C6A C7A C8A 118.0(10) . . ?
C2A C7A C6A 121.0(10) . . ?
C2A C7A C8A 121.0(7) . . ?
C3A C4A H4A 118.7 . . ?
C5A C4A C3A 122.5(9) . . ?
C5A C4A H4A 118.7 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.796
