# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_z0223m
_database_code_depnum_ccdc_archive 'CCDC 1537201'
_audit_update_record             
;
2017-03-10 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_audit_creation_date             2017-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_chemical_formula_moiety         'C24 H21 F2 O3 P'
_chemical_formula_sum            'C24 H21 F2 O3 P'
_chemical_formula_weight         426.40
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   25.317(4)
_cell_length_b                   8.8649(15)
_cell_length_c                   22.042(4)
_cell_angle_alpha                90
_cell_angle_beta                 120.571(2)
_cell_angle_gamma                90
_cell_volume                     4259.4(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8180
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.745
_cell_measurement_theta_min      2.480
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.661395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker,200?) was used for absorption correction. R(int) was 0.1268 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.6614. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3298
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1777.8731
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17795
_diffrn_reflns_theta_full        25.9990
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.87
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9943
_diffrn_measured_fraction_theta_max 0.9943
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              26
_reflns_limit_h_min              -31
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                3723
_reflns_number_total             4161
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.2762
_refine_diff_density_min         -0.2661
_refine_diff_density_rms         0.0509
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             10.8992
_refine_ls_goodness_of_fit_ref   1.0601
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.0601
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+3.7640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1347
_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
2. Others
 Fixed Sof: C25(0.5) H25a(0.5) H25b(0.5) C26(0.55) H26a(0.55) H26b(0.55)
 H26c(0.55) C24(0.45) H24a(0.45) H24b(0.45) H24c(0.45) C23(0.5) H23a(0.5)
 H23b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C23(H23a,H23b)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C20(H20), C8(H8), C12(H12), C9(H9), C5(H5), C6(H6), C4(H4),
 C14(H14), C10(H10), C18(H18), C15(H15), C3(H3), C17(H17), C16(H16), C2(H2)
3.c Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C24(H24a,H24b,H24c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_disorder_group
P1 P 0.06306(2) 0.72917(5) 0.12643(2) 0.03635(16) Uani 1.000000 . .
O1 O 0.00594(6) 0.64155(17) 0.08994(7) 0.0482(3) Uani 1.000000 . .
C19 C 0.10915(8) 0.6720(2) 0.21811(9) 0.0357(4) Uani 1.000000 . .
F1 F 0.06839(6) 0.44652(18) 0.32108(7) 0.0690(4) Uani 1.000000 . .
C13 C 0.17248(9) 0.7292(2) 0.26207(9) 0.0403(4) Uani 1.000000 . .
C11 C 0.16310(9) 0.7875(2) 0.10843(10) 0.0407(4) Uani 1.000000 . .
H11 H 0.17774(9) 0.8535(2) 0.14639(10) 0.0489(5) Uiso 1.000000 R .
C7 C 0.11011(8) 0.70579(19) 0.08807(9) 0.0348(4) Uani 1.000000 . .
F2 F 0.14601(7) 0.38066(17) 0.31153(8) 0.0722(4) Uani 1.000000 . .
C20 C 0.08341(9) 0.5723(2) 0.23916(9) 0.0412(4) Uani 1.000000 . .
H20 H 0.04332(9) 0.5437(2) 0.20702(9) 0.0494(5) Uiso 1.000000 R .
C8 C 0.08949(9) 0.6057(2) 0.03246(9) 0.0405(4) Uani 1.000000 . .
H8 H 0.05419(9) 0.5493(2) 0.01876(9) 0.0486(5) Uiso 1.000000 R .
O2 O 0.20523(8) 0.5629(2) 0.41718(8) 0.0765(6) Uani 1.000000 . .
C12 C 0.19417(10) 0.7713(2) 0.07276(12) 0.0489(5) Uani 1.000000 . .
H12 H 0.22950(10) 0.8273(2) 0.08619(12) 0.0587(6) Uiso 1.000000 R .
O3 O 0.12536(8) 0.7164(2) 0.37515(9) 0.0736(5) Uani 1.000000 . .
C9 C 0.12117(11) 0.5894(2) -0.00264(11) 0.0517(5) Uani 1.000000 . .
H9 H 0.10729(11) 0.5218(2) -0.03995(11) 0.0620(6) Uiso 1.000000 R .
C1 C 0.05108(9) 0.9285(2) 0.12783(10) 0.0466(5) Uani 1.000000 . .
C21 C 0.11315(10) 0.5015(3) 0.31013(11) 0.0492(5) Uani 1.000000 . .
C5 C 0.04256(11) 1.1779(2) 0.08124(13) 0.0615(6) Uani 1.000000 . .
H5 H 0.04688(11) 1.2429(2) 0.05094(13) 0.0738(8) Uiso 1.000000 R .
C6 C 0.05696(9) 1.0267(2) 0.08335(10) 0.0467(5) Uani 1.000000 . .
H6 H 0.07083(9) 0.9909(2) 0.05423(10) 0.0560(6) Uiso 1.000000 R .
C4 C 0.02221(15) 1.2311(3) 0.12320(14) 0.0859(10) Uani 1.000000 . .
H4 H 0.01226(15) 1.3325(3) 0.12164(14) 0.1030(12) Uiso 1.000000 R .
C22 C 0.15488(11) 0.5971(3) 0.37442(11) 0.0563(6) Uani 1.000000 . .
C14 C 0.22100(10) 0.6385(3) 0.27576(12) 0.0533(5) Uani 1.000000 . .
H14 H 0.21369(10) 0.5409(3) 0.25785(12) 0.0640(6) Uiso 1.000000 R .
C10 C 0.17306(11) 0.6724(3) 0.01725(12) 0.0545(5) Uani 1.000000 . .
H10 H 0.19409(11) 0.6618(3) -0.00693(12) 0.0654(7) Uiso 1.000000 R .
C18 C 0.18401(12) 0.8730(3) 0.28916(12) 0.0602(6) Uani 1.000000 . .
H18 H 0.15189(12) 0.9378(3) 0.27997(12) 0.0722(7) Uiso 1.000000 R .
C15 C 0.28038(11) 0.6891(3) 0.31551(15) 0.0735(8) Uani 1.000000 . .
H15 H 0.31269(11) 0.6264(3) 0.32329(15) 0.0882(9) Uiso 1.000000 R .
C3 C 0.0165(2) 1.1367(4) 0.16709(18) 0.1159(15) Uani 1.000000 . .
H3 H 0.0026(2) 1.1740(4) 0.19594(18) 0.1391(18) Uiso 1.000000 R .
C17 C 0.24455(17) 0.9195(3) 0.33055(15) 0.0849(9) Uani 1.000000 . .
H17 H 0.25288(17) 1.0157(3) 0.35017(15) 0.1018(11) Uiso 1.000000 R .
C16 C 0.29189(13) 0.8270(4) 0.34289(15) 0.0834(9) Uani 1.000000 . .
H16 H 0.33216(13) 0.8602(4) 0.37040(15) 0.1001(11) Uiso 1.000000 R .
C25 C 0.1527(4) 0.8549(11) 0.4246(4) 0.074(2) Uani 0.500000 . -1
H25a H 0.1967(4) 0.8610(11) 0.4437(4) 0.089(3) Uiso 0.500000 R -1
H25b H 0.1339(4) 0.9475(11) 0.3993(4) 0.089(3) Uiso 0.500000 R -1
C26 C 0.1397(4) 0.8323(10) 0.4793(4) 0.095(2) Uani 0.550000 . -1
H26a H 0.0962(4) 0.823(6) 0.4594(4) 0.142(3) Uiso 0.550000 GR -1
H26b H 0.160(2) 0.742(3) 0.5047(17) 0.142(3) Uiso 0.550000 GR -1
H26c H 0.154(2) 0.917(3) 0.5109(16) 0.142(3) Uiso 0.550000 GR -1
C2 C 0.03080(18) 0.9846(4) 0.17039(16) 0.0925(11) Uani 1.000000 . .
H2 H 0.02667(18) 0.9211(4) 0.20131(16) 0.1110(13) Uiso 1.000000 R .
C24 C 0.1212(5) 0.9134(11) 0.4374(6) 0.113(4) Uani 0.450000 . 1
H24a H 0.111(3) 0.973(5) 0.396(2) 0.170(5) Uiso 0.450000 GR 1
H24b H 0.0845(15) 0.8709(12) 0.433(4) 0.170(5) Uiso 0.450000 GR 1
H24c H 0.1407(14) 0.976(5) 0.478(2) 0.170(5) Uiso 0.450000 GR 1
C23 C 0.1651(4) 0.7857(9) 0.4445(4) 0.0625(17) Uani 0.500000 . 1
H23a H 0.1739(4) 0.7175(9) 0.4829(4) 0.075(2) Uiso 0.500000 R 1
H23b H 0.2031(4) 0.8236(9) 0.4496(4) 0.075(2) Uiso 0.500000 R 1


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 1.4691(14) . ?
P1 C19 1.8175(18) . ?
P1 C7 1.7892(18) . ?
P1 C1 1.796(2) . ?
C19 C13 1.479(2) . ?
C19 C20 1.315(3) . ?
F1 C21 1.363(2) . ?
C13 C14 1.367(3) . ?
C13 C18 1.374(3) . ?
C11 C7 1.383(3) . ?
C11 C12 1.374(3) . ?
C7 C8 1.383(2) . ?
F2 C21 1.347(3) . ?
C20 C21 1.487(3) . ?
C8 C9 1.376(3) . ?
O2 C22 1.176(3) . ?
C12 C10 1.373(3) . ?
O3 C22 1.300(3) . ?
O3 C25 1.552(8) . ?
O3 C23 1.469(7) . ?
C9 C10 1.369(3) . ?
C1 C6 1.374(3) . ?
C1 C2 1.371(3) . ?
C21 C22 1.523(3) . ?
C5 C6 1.383(3) . ?
C5 C4 1.352(4) . ?
C4 C3 1.342(5) . ?
C14 C15 1.374(3) . ?
C18 C17 1.389(4) . ?
C15 C16 1.329(4) . ?
C3 C2 1.389(4) . ?
C17 C16 1.361(5) . ?
C25 C26 1.417(11) . ?
C24 C23 1.538(11) . ?

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
C19 P1 O1 110.97(8) . . ?
C7 P1 O1 112.74(8) . . ?
C7 P1 C19 106.73(8) . . ?
C1 P1 O1 113.70(9) . . ?
C1 P1 C19 105.88(8) . . ?
C1 P1 C7 106.31(9) . . ?
C13 C19 P1 120.14(13) . . ?
C20 C19 P1 115.25(14) . . ?
C20 C19 C13 124.47(17) . . ?
C14 C13 C19 119.76(17) . . ?
C18 C13 C19 121.5(2) . . ?
C18 C13 C14 118.7(2) . . ?
C12 C11 C7 120.20(18) . . ?
C11 C7 P1 123.71(14) . . ?
C8 C7 P1 116.83(14) . . ?
C8 C7 C11 119.35(17) . . ?
C21 C20 C19 125.35(17) . . ?
C9 C8 C7 120.04(19) . . ?
C10 C12 C11 120.0(2) . . ?
C25 O3 C22 126.8(4) . . ?
C10 C9 C8 120.15(19) . . ?
C6 C1 P1 122.02(15) . . ?
C2 C1 P1 119.6(2) . . ?
C2 C1 C6 118.2(2) . . ?
F2 C21 F1 105.72(18) . . ?
C20 C21 F1 108.40(16) . . ?
C20 C21 F2 109.65(17) . . ?
C22 C21 F1 106.26(16) . . ?
C22 C21 F2 107.06(19) . . ?
C22 C21 C20 118.96(19) . . ?
C4 C5 C6 120.0(3) . . ?
C5 C6 C1 121.0(2) . . ?
C3 C4 C5 119.7(2) . . ?
O3 C22 O2 126.6(2) . . ?
C21 C22 O2 123.9(3) . . ?
C21 C22 O3 109.47(19) . . ?
C15 C14 C13 121.2(2) . . ?
C9 C10 C12 120.25(19) . . ?
C17 C18 C13 118.7(3) . . ?
C16 C15 C14 120.4(3) . . ?
C2 C3 C4 121.4(3) . . ?
C16 C17 C18 121.2(3) . . ?
C17 C16 C15 119.8(2) . . ?
C26 C25 O3 105.8(6) . . ?
C3 C2 C1 119.7(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
