# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_gouxy_1113_2
_database_code_depnum_ccdc_archive 'CCDC 1973724'
loop_
_audit_author_name
_audit_author_address
'xue-ya gou'
;lanzhou university
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_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         'C H Cl3, C23 H23 F N O2 P'
_chemical_formula_sum            'C24 H24 Cl3 F N O2 P'
_chemical_formula_weight         514.76
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   13.7106(3)
_cell_length_b                   10.0817(2)
_cell_length_c                   19.9799(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.4380(18)
_cell_angle_gamma                90
_cell_volume                     2760.85(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3607
_cell_measurement_temperature    236(20)
_cell_measurement_theta_max      69.7470
_cell_measurement_theta_min      9.0550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         4.427
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      236(20)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     53.00  80.00   1.00    2.00    --   54.00 -38.00 150.00   27
  2  ω     50.00 111.00   1.00    2.00    --  108.00-111.00  60.00   61
  3  ω     64.00 134.00   1.00    2.00    --  108.00 -77.00  60.00   70
  4  ω     56.00 107.00   1.00    2.00    --   54.00-125.00 120.00   51
  5  ω     38.00 130.00   1.00    2.00    --  108.00 -50.00  30.00   92
  6  ω     85.00 124.00   1.00    2.00    --   54.00  77.00 -60.00   39
  7  ω    129.00 164.00   1.00    2.00    --  108.00 111.00 -30.00   35
  8  ω     86.00 176.00   1.00    2.00    --  108.00  63.00-180.00   90
  9  ω     43.00 118.00   1.00    2.00    --   54.00  57.00-150.00   75
 10  ω     34.00  59.00   1.00    2.00    --    0.00  77.00   0.00   25
 11  ω     31.00 108.00   1.00    2.00    --   54.00  38.00 120.00   77
 12  ω     35.00  62.00   1.00    2.00    --   54.00  57.00   0.00   27
 13  ω     28.00  53.00   1.00    2.00    --   54.00  77.00 -60.00   25
 14  ω     38.00 121.00   1.00    2.00    --  108.00 -50.00 -90.00   83
 15  ω     38.00  84.00   1.00    2.00    --  108.00 -95.00 -75.00   46
 16  ω     -6.00  20.00   1.00    2.00    --    0.00 -57.00-120.00   26
 17  ω    -63.00 -12.00   1.00    2.00    --    0.00 -57.00-120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0474471000
_diffrn_orient_matrix_UB_12      -0.0290304000
_diffrn_orient_matrix_UB_13      -0.0675151000
_diffrn_orient_matrix_UB_21      0.0948159000
_diffrn_orient_matrix_UB_22      0.0673865000
_diffrn_orient_matrix_UB_23      0.0252789000
_diffrn_orient_matrix_UB_31      0.0374384000
_diffrn_orient_matrix_UB_32      -0.1340720000
_diffrn_orient_matrix_UB_33      0.0272946000
_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                3974
_reflns_number_total             4874
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.046
_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)+(0.0682P)²+1.1185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1399
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.28914(10) 0.32258(11) 0.27506(6) 0.1023(4) Uani 1 1 d . . . . .
Cl2 Cl 0.12124(8) 0.23754(14) 0.34796(6) 0.1016(4) Uani 1 1 d . . . . .
Cl3 Cl 0.31354(7) 0.21386(11) 0.40830(4) 0.0797(3) Uani 1 1 d . . . . .
C24 C 0.2458(3) 0.2093(3) 0.33370(16) 0.0613(8) Uani 1 1 d . . . . .
H24 H 0.252025 0.120119 0.314762 0.074 Uiso 1 1 calc R . . . .
P1 P 0.25720(4) 0.84521(6) 0.22865(3) 0.03005(16) Uani 1 1 d . . . . .
F1 F 0.19557(10) 0.59831(16) 0.14657(9) 0.0543(4) Uani 1 1 d . . . . .
O1 O 0.42415(16) 0.3364(3) 0.03918(12) 0.0744(7) Uani 1 1 d . . . . .
O2 O 0.31730(11) 0.93249(16) 0.27350(9) 0.0404(4) Uani 1 1 d . . . . .
N1 N 0.51449(14) 0.4095(2) 0.12787(10) 0.0367(4) Uani 1 1 d . . . . .
H1 H 0.568327 0.397989 0.150126 0.044 Uiso 1 1 calc R . . . .
C1 C 0.29268(15) 0.6016(2) 0.16269(12) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.34883(16) 0.5021(2) 0.13732(12) 0.0364(5) Uani 1 1 d . . . . .
H2 H 0.321369 0.436018 0.110408 0.044 Uiso 1 1 calc R . . . .
C3 C 0.44912(16) 0.5030(2) 0.15321(11) 0.0316(5) Uani 1 1 d . . . . .
C4 C 0.48590(16) 0.6007(2) 0.19572(12) 0.0357(5) Uani 1 1 d . . . . .
H4 H 0.551563 0.599325 0.208570 0.043 Uiso 1 1 calc R . . . .
C5 C 0.42672(16) 0.6996(2) 0.21915(12) 0.0347(5) Uani 1 1 d . . . . .
H5 H 0.453681 0.765244 0.246580 0.042 Uiso 1 1 calc R . . . .
C6 C 0.32699(15) 0.7040(2) 0.20276(11) 0.0311(5) Uani 1 1 d . . . . .
C7 C 0.50077(19) 0.3346(3) 0.07100(13) 0.0415(6) Uani 1 1 d . . . . .
C8 C 0.5871(2) 0.2502(3) 0.04977(13) 0.0457(6) Uani 1 1 d . . . . .
C9 C 0.5969(3) 0.1334(4) 0.09845(19) 0.0820(12) Uani 1 1 d . . . . .
H9A H 0.609314 0.166243 0.142952 0.123 Uiso 1 1 calc GR . . . .
H9B H 0.650082 0.077743 0.085516 0.123 Uiso 1 1 calc GR . . . .
H9C H 0.537559 0.082857 0.097411 0.123 Uiso 1 1 calc GR . . . .
C10 C 0.6814(2) 0.3317(4) 0.0494(2) 0.0846(12) Uani 1 1 d . . . . .
H10A H 0.670872 0.411048 0.023697 0.127 Uiso 1 1 calc GR . . . .
H10B H 0.732273 0.280246 0.029848 0.127 Uiso 1 1 calc GR . . . .
H10C H 0.700260 0.354876 0.094535 0.127 Uiso 1 1 calc GR . . . .
C11 C 0.5655(3) 0.1979(4) -0.02078(16) 0.0729(10) Uani 1 1 d . . . . .
H11A H 0.507424 0.144660 -0.020696 0.109 Uiso 1 1 calc GR . . . .
H11B H 0.619308 0.144910 -0.035060 0.109 Uiso 1 1 calc GR . . . .
H11C H 0.556118 0.271166 -0.050934 0.109 Uiso 1 1 calc GR . . . .
C12 C 0.14821(16) 0.7891(2) 0.26783(12) 0.0335(5) Uani 1 1 d . . . . .
C13 C 0.1418(2) 0.6649(3) 0.29711(15) 0.0483(6) Uani 1 1 d . . . . .
H13 H 0.192652 0.604525 0.293461 0.058 Uiso 1 1 calc R . . . .
C14 C 0.0589(2) 0.6310(3) 0.33196(17) 0.0633(8) Uani 1 1 d . . . . .
H14 H 0.054751 0.547935 0.351936 0.076 Uiso 1 1 calc R . . . .
C15 C -0.0160(2) 0.7183(4) 0.33706(17) 0.0669(9) Uani 1 1 d . . . . .
H15 H -0.071396 0.694243 0.360071 0.080 Uiso 1 1 calc R . . . .
C16 C -0.0105(2) 0.8417(4) 0.30850(17) 0.0623(8) Uani 1 1 d . . . . .
H16 H -0.062014 0.901035 0.312216 0.075 Uiso 1 1 calc R . . . .
C17 C 0.07170(18) 0.8780(3) 0.27418(14) 0.0458(6) Uani 1 1 d . . . . .
H17 H 0.075714 0.962088 0.255318 0.055 Uiso 1 1 calc R . . . .
C18 C 0.22094(17) 0.9299(2) 0.15229(12) 0.0371(5) Uani 1 1 d . . . . .
C19 C 0.1439(2) 0.8867(3) 0.11129(14) 0.0511(7) Uani 1 1 d . . . . .
H19 H 0.105295 0.816178 0.124747 0.061 Uiso 1 1 calc R . . . .
C20 C 0.1245(3) 0.9485(4) 0.05025(17) 0.0678(9) Uani 1 1 d . . . . .
H20 H 0.073524 0.918369 0.022685 0.081 Uiso 1 1 calc R . . . .
C21 C 0.1796(3) 1.0526(4) 0.03070(18) 0.0738(10) Uani 1 1 d . . . . .
H21 H 0.166173 1.093157 -0.010309 0.089 Uiso 1 1 calc R . . . .
C22 C 0.2545(3) 1.0984(3) 0.07069(18) 0.0689(10) Uani 1 1 d . . . . .
H22 H 0.291141 1.170774 0.057195 0.083 Uiso 1 1 calc R . . . .
C23 C 0.2760(2) 1.0368(3) 0.13150(15) 0.0512(7) Uani 1 1 d . . . . .
H23 H 0.327541 1.067562 0.158382 0.061 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
Cl1 C24 1.751(4) . ?
Cl2 C24 1.761(4) . ?
Cl3 C24 1.737(3) . ?
C24 H24 0.9800 . ?
P1 O2 1.4897(16) . ?
P1 C6 1.799(2) . ?
P1 C12 1.796(2) . ?
P1 C18 1.807(3) . ?
F1 C1 1.362(2) . ?
O1 C7 1.214(3) . ?
N1 H1 0.8600 . ?
N1 C3 1.404(3) . ?
N1 C7 1.373(3) . ?
C1 C2 1.369(3) . ?
C1 C6 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.404(3) . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(3) . ?
C7 C8 1.527(3) . ?
C8 C9 1.531(4) . ?
C8 C10 1.532(4) . ?
C8 C11 1.527(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.386(4) . ?
C12 C17 1.388(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(4) . ?
C18 C23 1.386(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.356(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.366(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(4) . ?
C23 H23 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
Cl1 C24 Cl2 110.47(17) . . ?
Cl1 C24 H24 107.8 . . ?
Cl2 C24 H24 107.8 . . ?
Cl3 C24 Cl1 111.9(2) . . ?
Cl3 C24 Cl2 110.91(19) . . ?
Cl3 C24 H24 107.8 . . ?
O2 P1 C6 110.51(10) . . ?
O2 P1 C12 112.19(10) . . ?
O2 P1 C18 111.43(11) . . ?
C6 P1 C18 105.56(11) . . ?
C12 P1 C6 109.29(11) . . ?
C12 P1 C18 107.62(11) . . ?
C3 N1 H1 116.8 . . ?
C7 N1 H1 116.8 . . ?
C7 N1 C3 126.3(2) . . ?
F1 C1 C2 116.7(2) . . ?
F1 C1 C6 118.2(2) . . ?
C2 C1 C6 125.1(2) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 117.9(2) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 N1 123.0(2) . . ?
C4 C3 N1 118.2(2) . . ?
C4 C3 C2 118.8(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 P1 125.60(17) . . ?
C1 C6 C5 115.4(2) . . ?
C5 C6 P1 118.79(17) . . ?
O1 C7 N1 121.6(2) . . ?
O1 C7 C8 122.0(2) . . ?
N1 C7 C8 116.4(2) . . ?
C7 C8 C9 108.0(2) . . ?
C7 C8 C10 111.3(2) . . ?
C7 C8 C11 108.3(2) . . ?
C9 C8 C10 110.8(3) . . ?
C11 C8 C9 109.4(3) . . ?
C11 C8 C10 109.0(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 P1 122.09(19) . . ?
C13 C12 C17 119.3(2) . . ?
C17 C12 P1 118.38(19) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C19 C18 P1 122.6(2) . . ?
C23 C18 P1 118.7(2) . . ?
C23 C18 C19 118.6(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.3(3) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?

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 C12 C13 C14 174.2(2) . . . . ?
P1 C12 C17 C16 -175.1(2) . . . . ?
P1 C18 C19 C20 -174.4(2) . . . . ?
P1 C18 C23 C22 175.4(2) . . . . ?
F1 C1 C2 C3 -179.9(2) . . . . ?
F1 C1 C6 P1 -7.3(3) . . . . ?
F1 C1 C6 C5 178.2(2) . . . . ?
O1 C7 C8 C9 -107.4(3) . . . . ?
O1 C7 C8 C10 130.8(3) . . . . ?
O1 C7 C8 C11 11.0(4) . . . . ?
O2 P1 C6 C1 178.0(2) . . . . ?
O2 P1 C6 C5 -7.6(2) . . . . ?
O2 P1 C12 C13 -98.7(2) . . . . ?
O2 P1 C12 C17 75.2(2) . . . . ?
O2 P1 C18 C19 -161.4(2) . . . . ?
O2 P1 C18 C23 23.0(2) . . . . ?
N1 C3 C4 C5 176.3(2) . . . . ?
N1 C7 C8 C9 73.1(3) . . . . ?
N1 C7 C8 C10 -48.7(4) . . . . ?
N1 C7 C8 C11 -168.5(3) . . . . ?
C1 C2 C3 N1 -177.3(2) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C2 C1 C6 P1 172.5(2) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C2 C3 C4 C5 -3.6(4) . . . . ?
C3 N1 C7 O1 -5.8(4) . . . . ?
C3 N1 C7 C8 173.8(2) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C4 C5 C6 P1 -173.97(19) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C6 P1 C12 C13 24.2(2) . . . . ?
C6 P1 C12 C17 -161.87(19) . . . . ?
C6 P1 C18 C19 78.6(2) . . . . ?
C6 P1 C18 C23 -97.0(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C7 N1 C3 C2 22.1(4) . . . . ?
C7 N1 C3 C4 -157.8(2) . . . . ?
C12 P1 C6 C1 54.1(2) . . . . ?
C12 P1 C6 C5 -131.51(19) . . . . ?
C12 P1 C18 C19 -38.0(2) . . . . ?
C12 P1 C18 C23 146.3(2) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C12 C17 C16 -1.0(4) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 C12 0.8(5) . . . . ?
C17 C12 C13 C14 0.4(4) . . . . ?
C18 P1 C6 C1 -61.4(2) . . . . ?
C18 P1 C6 C5 113.0(2) . . . . ?
C18 P1 C12 C13 138.3(2) . . . . ?
C18 P1 C12 C17 -47.7(2) . . . . ?
C18 C19 C20 C21 -1.0(5) . . . . ?
C19 C18 C23 C22 -0.4(4) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C23 1.1(5) . . . . ?
C21 C22 C23 C18 -0.8(5) . . . . ?
C23 C18 C19 C20 1.3(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 153.4 58.7 ?
2 0.000 0.500 0.000 153.4 58.7 ?

_olex2_date_sample_data_collection 2019-11-14
_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 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.703
_exptl_crystal_recrystallization_method Sublimation
