# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1827907'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;
_audit_creation_date             2017-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        AKY-623
_chemical_formula_moiety         'C27 H21 Mo O6 P'
_chemical_formula_sum            'C27 H21 Mo O6 P'
_chemical_formula_weight         568.35
_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 0.0033 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'
Mo Mo -1.6832 0.6857 '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                   9.6734(4)
_cell_length_b                   10.6787(4)
_cell_length_c                   12.9836(5)
_cell_angle_alpha                76.188(2)
_cell_angle_beta                 83.221(2)
_cell_angle_gamma                73.4935(19)
_cell_volume                     1246.92(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6663
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0840 before and 0.0485 after correction. The Ratio of minimum to maximum transmission is 0.8930. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35439
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         3.236
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5670
_reflns_number_total             6000
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.4712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0614
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C1S)=Sof(H1S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=Sof(H2BC)=Sof(H2BD)=
 1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C3S(H3SA,H3SB,H3SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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
Mo Mo 0.52953(2) 0.53715(2) 0.71909(2) 0.01622(5) Uani 1 1 d . . . . .
P P 0.61650(5) 0.71479(5) 0.76633(4) 0.01317(10) Uani 1 1 d . . . . .
O1 O 0.49961(15) 0.86512(14) 0.75121(11) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.4290(2) 0.29757(19) 0.67749(17) 0.0429(5) Uani 1 1 d . . . . .
O3 O 0.76916(18) 0.46853(19) 0.53442(13) 0.0354(4) Uani 1 1 d . . . . .
O4 O 0.70164(18) 0.32820(15) 0.90917(12) 0.0281(3) Uani 1 1 d . . . . .
O5 O 0.26551(17) 0.57879(18) 0.88907(13) 0.0324(4) Uani 1 1 d . . . . .
O6 O 0.32822(19) 0.75344(18) 0.54374(15) 0.0380(4) Uani 1 1 d . . . . .
C1 C 0.4522(6) 0.8412(6) 0.8724(4) 0.0221(11) Uani 0.498(7) 1 d . . P A 1
H1 H 0.365(6) 0.810(5) 0.881(4) 0.026 Uiso 0.498(7) 1 d R . P A 1
C3 C 0.4277(6) 0.9676(5) 0.9112(4) 0.0316(14) Uani 0.498(7) 1 d . . P A 1
H3A H 0.3995 0.9514 0.9872 0.047 Uiso 0.498(7) 1 calc GR . P A 1
H3B H 0.3506 1.0374 0.8723 0.047 Uiso 0.498(7) 1 calc GR . P A 1
H3C H 0.5168 0.9965 0.8995 0.047 Uiso 0.498(7) 1 calc GR . P A 1
C1S C 0.4956(6) 0.8806(6) 0.8573(4) 0.0197(11) Uani 0.502(7) 1 d . . P A 2
H1S H 0.544(5) 0.951(5) 0.863(4) 0.024 Uiso 0.502(7) 1 d R . P A 2
C3S C 0.3413(5) 0.9131(5) 0.8992(4) 0.0263(13) Uani 0.502(7) 1 d . . P A 2
H3SA H 0.2881 0.9990 0.8575 0.039 Uiso 0.502(7) 1 calc GR . P A 2
H3SB H 0.3375 0.9187 0.9738 0.039 Uiso 0.502(7) 1 calc GR . P A 2
H3SC H 0.2977 0.8428 0.8937 0.039 Uiso 0.502(7) 1 calc GR . P A 2
C2 C 0.5898(2) 0.7324(2) 0.90556(16) 0.0210(4) Uani 1 1 d . . . . .
H2AA H 0.5731 0.6524 0.9569 0.025 Uiso 0.498(7) 1 calc R . P A 1
H2AB H 0.6646 0.7648 0.9289 0.025 Uiso 0.498(7) 1 calc R . P A 1
H2BC H 0.5341 0.6739 0.9522 0.025 Uiso 0.502(7) 1 calc R . P A 2
H2BD H 0.6787 0.7285 0.9383 0.025 Uiso 0.502(7) 1 calc R . P A 2
C4 C 0.8007(2) 0.74282(18) 0.71632(15) 0.0135(4) Uani 1 1 d . . . . .
C5 C 0.8037(2) 0.80190(18) 0.59606(15) 0.0155(4) Uani 1 1 d . . . . .
C6 C 0.6837(2) 0.8404(2) 0.53520(16) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.5952 0.8241 0.5671 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6912(3) 0.9028(2) 0.42788(17) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.6083 0.9284 0.3873 0.029 Uiso 1 1 calc R . . . .
C8 C 0.8193(3) 0.9273(2) 0.38091(17) 0.0286(5) Uani 1 1 d . . . . .
H8 H 0.8248 0.9702 0.3081 0.034 Uiso 1 1 calc R . . . .
C9 C 0.9400(3) 0.8889(2) 0.44077(18) 0.0281(5) Uani 1 1 d . . . . .
H9 H 1.0287 0.9043 0.4084 0.034 Uiso 1 1 calc R . . . .
C10 C 0.9322(2) 0.8283(2) 0.54705(17) 0.0216(4) Uani 1 1 d . . . . .
H10 H 1.0151 0.8043 0.5874 0.026 Uiso 1 1 calc R . . . .
C11 C 0.9030(2) 0.60074(19) 0.74569(16) 0.0158(4) Uani 1 1 d . . . . .
C12 C 0.9828(2) 0.5344(2) 0.66906(17) 0.0209(4) Uani 1 1 d . . . . .
H12 H 0.9770 0.5783 0.5963 0.025 Uiso 1 1 calc R . . . .
C13 C 1.0710(2) 0.4048(2) 0.6970(2) 0.0275(5) Uani 1 1 d . . . . .
H13 H 1.1246 0.3614 0.6432 0.033 Uiso 1 1 calc R . . . .
C14 C 1.0811(2) 0.3389(2) 0.8022(2) 0.0296(5) Uani 1 1 d . . . . .
H14 H 1.1420 0.2508 0.8211 0.035 Uiso 1 1 calc R . . . .
C15 C 1.0016(2) 0.4024(2) 0.87978(19) 0.0267(5) Uani 1 1 d . . . . .
H15 H 1.0077 0.3575 0.9523 0.032 Uiso 1 1 calc R . . . .
C16 C 0.9126(2) 0.5320(2) 0.85201(17) 0.0208(4) Uani 1 1 d . . . . .
H16 H 0.8577 0.5742 0.9059 0.025 Uiso 1 1 calc R . . . .
C17 C 0.8348(2) 0.84580(19) 0.76782(15) 0.0155(4) Uani 1 1 d . . . . .
C18 C 0.9459(2) 0.8142(2) 0.83624(16) 0.0192(4) Uani 1 1 d . . . . .
H18 H 1.0029 0.7244 0.8549 0.023 Uiso 1 1 calc R . . . .
C19 C 0.9747(2) 0.9121(2) 0.87770(18) 0.0263(5) Uani 1 1 d . . . . .
H19 H 1.0499 0.8880 0.9253 0.032 Uiso 1 1 calc R . . . .
C20 C 0.8952(2) 1.0443(2) 0.85057(17) 0.0247(5) Uani 1 1 d . . . . .
H20 H 0.9150 1.1108 0.8794 0.030 Uiso 1 1 calc R . . . .
C21 C 0.7862(2) 1.0778(2) 0.78069(17) 0.0228(4) Uani 1 1 d . . . . .
H21 H 0.7312 1.1682 0.7610 0.027 Uiso 1 1 calc R . . . .
C22 C 0.7567(2) 0.9804(2) 0.73935(17) 0.0213(4) Uani 1 1 d . . . . .
H22 H 0.6824 1.0052 0.6909 0.026 Uiso 1 1 calc R . . . .
C23 C 0.4615(2) 0.3868(2) 0.69120(19) 0.0264(5) Uani 1 1 d . . . . .
C24 C 0.6897(2) 0.4961(2) 0.60199(17) 0.0227(4) Uani 1 1 d . . . . .
C25 C 0.6455(2) 0.4033(2) 0.83851(17) 0.0198(4) Uani 1 1 d . . . . .
C26 C 0.3608(2) 0.5675(2) 0.82759(17) 0.0219(4) Uani 1 1 d . . . . .
C27 C 0.4004(2) 0.6772(2) 0.60526(18) 0.0243(4) Uani 1 1 d . . . . .


_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
Mo P 2.5034(5) . ?
Mo C23 2.019(2) . ?
Mo C24 2.069(2) . ?
Mo C25 2.036(2) . ?
Mo C26 2.032(2) . ?
Mo C27 2.074(2) . ?
P O1 1.6627(14) . ?
P C2 1.842(2) . ?
P C4 1.9039(19) . ?
O1 C1 1.567(5) . ?
O1 C1S 1.420(5) . ?
O2 C23 1.142(3) . ?
O3 C24 1.132(3) . ?
O4 C25 1.139(3) . ?
O5 C26 1.145(3) . ?
O6 C27 1.134(3) . ?
C1 C3 1.498(8) . ?
C1 C2 1.525(6) . ?
C1S C3S 1.499(7) . ?
C1S C2 1.603(6) . ?
C4 C5 1.538(3) . ?
C4 C11 1.545(3) . ?
C4 C17 1.541(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.399(3) . ?
C6 C7 1.397(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.388(4) . ?
C9 C10 1.380(3) . ?
C11 C12 1.390(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.395(3) . ?
C17 C18 1.391(3) . ?
C17 C22 1.403(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.385(3) . ?
C21 C22 1.387(3) . ?

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
C23 Mo P 176.12(7) . . ?
C23 Mo C24 86.11(9) . . ?
C23 Mo C25 88.44(9) . . ?
C23 Mo C26 88.32(9) . . ?
C23 Mo C27 92.01(9) . . ?
C24 Mo P 95.80(6) . . ?
C24 Mo C27 89.53(9) . . ?
C25 Mo P 88.05(6) . . ?
C25 Mo C24 94.39(8) . . ?
C25 Mo C27 176.07(9) . . ?
C26 Mo P 89.88(6) . . ?
C26 Mo C24 174.08(8) . . ?
C26 Mo C25 87.45(8) . . ?
C26 Mo C27 88.66(9) . . ?
C27 Mo P 91.38(6) . . ?
O1 P Mo 115.51(5) . . ?
O1 P C2 80.43(8) . . ?
O1 P C4 106.67(8) . . ?
C2 P Mo 117.93(7) . . ?
C2 P C4 106.65(9) . . ?
C4 P Mo 121.85(6) . . ?
C1 O1 P 91.9(2) . . ?
C1S O1 P 97.4(2) . . ?
C3 C1 O1 110.0(5) . . ?
C3 C1 C2 116.3(5) . . ?
C2 C1 O1 94.3(3) . . ?
O1 C1S C3S 108.7(4) . . ?
O1 C1S C2 97.0(3) . . ?
C3S C1S C2 114.9(5) . . ?
C1 C2 P 86.7(2) . . ?
C1S C2 P 84.4(2) . . ?
C5 C4 P 110.72(13) . . ?
C5 C4 C11 112.71(15) . . ?
C5 C4 C17 105.68(14) . . ?
C11 C4 P 102.66(12) . . ?
C17 C4 P 111.17(13) . . ?
C17 C4 C11 114.04(15) . . ?
C6 C5 C4 123.96(17) . . ?
C6 C5 C10 118.11(18) . . ?
C10 C5 C4 117.71(17) . . ?
C5 C6 C7 121.1(2) . . ?
C8 C7 C6 119.9(2) . . ?
C7 C8 C9 119.6(2) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C5 120.9(2) . . ?
C12 C11 C4 122.13(17) . . ?
C12 C11 C16 117.73(18) . . ?
C16 C11 C4 120.07(18) . . ?
C11 C12 C13 121.3(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 119.4(2) . . ?
C14 C15 C16 120.3(2) . . ?
C15 C16 C11 120.9(2) . . ?
C18 C17 C4 123.40(17) . . ?
C18 C17 C22 117.67(18) . . ?
C22 C17 C4 118.80(17) . . ?
C19 C18 C17 120.9(2) . . ?
C20 C19 C18 120.9(2) . . ?
C19 C20 C21 118.83(19) . . ?
C20 C21 C22 120.5(2) . . ?
C21 C22 C17 121.17(19) . . ?
O2 C23 Mo 176.7(2) . . ?
O3 C24 Mo 173.68(18) . . ?
O4 C25 Mo 175.31(18) . . ?
O5 C26 Mo 176.91(18) . . ?
O6 C27 Mo 179.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1827910'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;
_audit_creation_date             2017-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        FLG-17
_chemical_formula_moiety         'C22 H21 Au Cl O P'
_chemical_formula_sum            'C22 H21 Au Cl O P'
_chemical_formula_weight         564.77
_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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 '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                   8.3743(4)
_cell_length_b                   7.4432(3)
_cell_length_c                   31.6312(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.768(2)
_cell_angle_gamma                90
_cell_volume                     1957.88(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.576
_shelx_estimated_absorpt_T_min   0.248
_exptl_absorpt_coefficient_mu    7.740
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2985
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1578 before and 0.0656 after correction. The Ratio of minimum to maximum transmission is 0.4001. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2257
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            48893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.449
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4170
_reflns_number_total             4720
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         4.488
_refine_diff_density_min         -3.087
_refine_diff_density_rms         0.412
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1295
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Me refined with riding coordinates:
 C3(H3A,H3B,H3C)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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
Au Au 0.39763(2) 0.25738(2) 0.53875(2) 0.01433(11) Uani 1 1 d . . . . .
Cl Cl 0.16982(18) 0.21913(18) 0.49191(5) 0.0221(3) Uani 1 1 d . . . . .
P P 0.61549(15) 0.30229(18) 0.58459(4) 0.0128(2) Uani 1 1 d . . . . .
O O 0.7252(4) 0.1296(4) 0.60125(10) 0.0171(7) Uani 1 1 d . . . . .
C1 C 0.8617(6) 0.1819(7) 0.57629(16) 0.0197(10) Uani 1 1 d . . . . .
H1 H 0.857(7) 0.103(7) 0.5516(16) 0.024 Uiso 1 1 d R . . . .
C2 C 0.8005(6) 0.3742(6) 0.56530(15) 0.0179(10) Uani 1 1 d . . . . .
H2A H 0.7897 0.4033 0.5346 0.021 Uiso 1 1 calc R . . . .
H2B H 0.8589 0.4698 0.5826 0.021 Uiso 1 1 calc R . . . .
C3 C 1.0202(6) 0.1650(7) 0.60308(16) 0.0234(11) Uani 1 1 d . . . . .
H3A H 1.1065 0.1994 0.5863 0.035 Uiso 1 1 calc R . . . .
H3B H 1.0221 0.2441 0.6279 0.035 Uiso 1 1 calc R . . . .
H3C H 1.0360 0.0403 0.6126 0.035 Uiso 1 1 calc R . . . .
C4 C 0.5646(5) 0.4377(6) 0.63148(13) 0.0127(9) Uani 1 1 d . . . . .
C5 C 0.4793(6) 0.3171(7) 0.66147(15) 0.0154(9) Uani 1 1 d . . . . .
C6 C 0.4288(6) 0.1408(7) 0.65204(15) 0.0189(10) Uani 1 1 d . . . . .
H6 H 0.4495 0.0870 0.6260 0.023 Uiso 1 1 calc R . . . .
C7 C 0.3481(6) 0.0440(7) 0.68081(16) 0.0238(11) Uani 1 1 d . . . . .
H7 H 0.3132 -0.0751 0.6740 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3188(6) 0.1184(8) 0.71863(16) 0.0250(12) Uani 1 1 d . . . . .
H8 H 0.2641 0.0511 0.7380 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3691(7) 0.2929(9) 0.72864(17) 0.0246(11) Uani 1 1 d . . . . .
H9 H 0.3491 0.3453 0.7549 0.029 Uiso 1 1 calc R . . . .
C10 C 0.4485(6) 0.3899(7) 0.70011(14) 0.0186(10) Uani 1 1 d . . . . .
H10 H 0.4827 0.5090 0.7071 0.022 Uiso 1 1 calc R . . . .
C11 C 0.4491(5) 0.5783(6) 0.60891(13) 0.0135(9) Uani 1 1 d . . . . .
C12 C 0.2865(5) 0.5853(6) 0.61456(14) 0.0164(9) Uani 1 1 d . . . . .
H12 H 0.2482 0.5134 0.6361 0.020 Uiso 1 1 calc R . . . .
C13 C 0.1810(6) 0.6929(7) 0.58995(18) 0.0237(11) Uani 1 1 d . . . . .
H13 H 0.0706 0.6935 0.5942 0.028 Uiso 1 1 calc R . . . .
C14 C 0.2349(6) 0.8026(7) 0.55839(16) 0.0205(10) Uani 1 1 d . . . . .
H14 H 0.1625 0.8796 0.5416 0.025 Uiso 1 1 calc R . . . .
C15 C 0.3956(6) 0.7962(7) 0.55234(16) 0.0171(10) Uani 1 1 d . . . . .
H15 H 0.4332 0.8684 0.5308 0.021 Uiso 1 1 calc R . . . .
C16 C 0.5038(6) 0.6856(6) 0.57722(14) 0.0155(9) Uani 1 1 d . . . . .
H16 H 0.6139 0.6833 0.5727 0.019 Uiso 1 1 calc R . . . .
C17 C 0.7178(5) 0.5157(6) 0.65626(13) 0.0139(9) Uani 1 1 d . . . . .
C18 C 0.7551(6) 0.6987(7) 0.65739(15) 0.0182(10) Uani 1 1 d . . . . .
H18 H 0.6832 0.7819 0.6425 0.022 Uiso 1 1 calc R . . . .
C19 C 0.8972(8) 0.7601(6) 0.6802(2) 0.0242(14) Uani 1 1 d . . . . .
H19 H 0.9206 0.8850 0.6808 0.029 Uiso 1 1 calc R . . . .
C20 C 1.0034(6) 0.6429(8) 0.70185(15) 0.0255(11) Uani 1 1 d . . . . .
H20 H 1.1013 0.6858 0.7166 0.031 Uiso 1 1 calc R . . . .
C21 C 0.9669(6) 0.4602(7) 0.70201(14) 0.0229(11) Uani 1 1 d . . . . .
H21 H 1.0386 0.3783 0.7175 0.027 Uiso 1 1 calc R . . . .
C22 C 0.8248(6) 0.3984(7) 0.67939(13) 0.0178(9) Uani 1 1 d . . . . .
H22 H 0.8001 0.2739 0.6797 0.021 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
Au Cl 2.2912(15) . ?
Au P 2.2179(13) . ?
P O 1.631(3) . ?
P C2 1.812(5) . ?
P C4 1.883(4) . ?
O C1 1.514(5) . ?
C1 H1 0.98(5) . ?
C1 C2 1.546(7) . ?
C1 C3 1.493(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.541(6) . ?
C4 C11 1.542(6) . ?
C4 C17 1.537(6) . ?
C5 C6 1.400(7) . ?
C5 C10 1.389(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.367(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(6) . ?
C11 C16 1.400(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.366(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.405(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(7) . ?
C17 C22 1.394(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.370(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(7) . ?
C22 H22 0.9500 . ?

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
P Au Cl 178.31(4) . . ?
O P Au 118.77(14) . . ?
O P C2 82.52(19) . . ?
O P C4 109.78(18) . . ?
C2 P Au 119.65(17) . . ?
C2 P C4 112.9(2) . . ?
C4 P Au 110.51(14) . . ?
C1 O P 93.5(3) . . ?
O C1 H1 107(3) . . ?
O C1 C2 96.0(3) . . ?
C2 C1 H1 113(3) . . ?
C3 C1 O 110.9(4) . . ?
C3 C1 H1 111(3) . . ?
C3 C1 C2 117.0(5) . . ?
P C2 H2A 114.4 . . ?
P C2 H2B 114.4 . . ?
C1 C2 P 85.7(3) . . ?
C1 C2 H2A 114.4 . . ?
C1 C2 H2B 114.4 . . ?
H2A C2 H2B 111.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 P 109.7(3) . . ?
C5 C4 C11 111.7(4) . . ?
C11 C4 P 100.7(3) . . ?
C17 C4 P 110.5(3) . . ?
C17 C4 C5 109.0(3) . . ?
C17 C4 C11 114.8(4) . . ?
C6 C5 C4 124.4(4) . . ?
C10 C5 C4 117.5(4) . . ?
C10 C5 C6 118.1(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 H10 119.2 . . ?
C9 C10 C5 121.5(5) . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C4 122.3(4) . . ?
C12 C11 C16 118.5(4) . . ?
C16 C11 C4 118.6(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.5(5) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.3(5) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C4 123.5(4) . . ?
C22 C17 C4 118.5(4) . . ?
C22 C17 C18 118.0(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.7(5) . . ?
C22 C21 H21 120.2 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.3(5) . . ?
C21 C22 H22 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#END---------------------------------------------------------------------------

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1827908'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;
_audit_creation_date             2017-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        AKY-630
_chemical_formula_moiety         'C22 H21 O P'
_chemical_formula_sum            'C22 H21 O P'
_chemical_formula_weight         332.36
_chemical_absolute_configuration ad
_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 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3304(3)
_cell_length_b                   25.6709(9)
_cell_length_c                   9.0341(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.043(2)
_cell_angle_gamma                90
_cell_volume                     1750.31(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17137
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.8819
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14129
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_temperature      123
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7538
_reflns_number_total             8403
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 3315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         8403
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      0.972
_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)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0757
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2'(H2'A,H2'B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6'(H6'),
  C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10'), C12'(H12'), C13'(H13'), C14'(H14'),
 C15'(H15'), C16'(H16'), C18'(H18'), C19'(H19'), C20'(H20'), C21'(H21'),
 C22'(H22')
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C3'(H3'A,H3'B,H3'C)
;
_atom_sites_solution_hydrogens   mixed
_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
P P 0.62008(7) 0.33563(2) 0.45676(7) 0.01952(13) Uani 1 1 d . . . . .
O O 0.6771(2) 0.33540(7) 0.3002(2) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.8713(3) 0.33589(10) 0.4034(3) 0.0288(5) Uani 1 1 d . . . . .
H1 H 0.922(4) 0.3670(12) 0.370(4) 0.035 Uiso 1 1 d R . . . .
C2 C 0.8642(3) 0.34101(10) 0.5706(3) 0.0252(5) Uani 1 1 d . . . . .
H2A H 0.9056 0.3751 0.6249 0.030 Uiso 1 1 calc R . . . .
H2B H 0.9200 0.3117 0.6463 0.030 Uiso 1 1 calc R . . . .
C3 C 0.9533(5) 0.28658(12) 0.3774(5) 0.0468(8) Uani 1 1 d . . . . .
H3A H 0.9004 0.2565 0.4070 0.070 Uiso 1 1 calc GR . . . .
H3B H 1.0812 0.2871 0.4460 0.070 Uiso 1 1 calc GR . . . .
H3C H 0.9318 0.2839 0.2623 0.070 Uiso 1 1 calc GR . . . .
C4 C 0.5333(3) 0.40498(8) 0.4599(3) 0.0158(4) Uani 1 1 d . . . . .
C5 C 0.6710(3) 0.44603(8) 0.4721(3) 0.0159(4) Uani 1 1 d . . . . .
C6 C 0.7488(3) 0.47906(8) 0.6077(3) 0.0179(4) Uani 1 1 d . . . . .
H6 H 0.7122 0.4772 0.6939 0.022 Uiso 1 1 calc R . . . .
C7 C 0.8793(3) 0.51458(9) 0.6171(3) 0.0231(5) Uani 1 1 d . . . . .
H7 H 0.9313 0.5366 0.7100 0.028 Uiso 1 1 calc R . . . .
C8 C 0.9338(3) 0.51809(9) 0.4927(3) 0.0229(5) Uani 1 1 d . . . . .
H8 H 1.0239 0.5421 0.5004 0.027 Uiso 1 1 calc R . . . .
C9 C 0.8559(3) 0.48642(9) 0.3566(3) 0.0214(4) Uani 1 1 d . . . . .
H9 H 0.8924 0.4888 0.2704 0.026 Uiso 1 1 calc R . . . .
C10 C 0.7249(3) 0.45126(8) 0.3456(3) 0.0184(4) Uani 1 1 d . . . . .
H10 H 0.6707 0.4303 0.2504 0.022 Uiso 1 1 calc R . . . .
C11 C 0.4867(3) 0.40485(8) 0.6068(3) 0.0162(4) Uani 1 1 d . . . . .
C12 C 0.6026(3) 0.38233(9) 0.7553(3) 0.0206(4) Uani 1 1 d . . . . .
H12 H 0.7091 0.3666 0.7631 0.025 Uiso 1 1 calc R . . . .
C13 C 0.5651(3) 0.38256(9) 0.8909(3) 0.0239(5) Uani 1 1 d . . . . .
H13 H 0.6464 0.3675 0.9905 0.029 Uiso 1 1 calc R . . . .
C14 C 0.4099(3) 0.40466(10) 0.8816(3) 0.0240(5) Uani 1 1 d . . . . .
H14 H 0.3834 0.4046 0.9741 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2931(3) 0.42698(9) 0.7357(3) 0.0237(5) Uani 1 1 d . . . . .
H15 H 0.1865 0.4425 0.7286 0.028 Uiso 1 1 calc R . . . .
C16 C 0.3308(3) 0.42688(9) 0.6002(3) 0.0207(5) Uani 1 1 d . . . . .
H16 H 0.2490 0.4421 0.5011 0.025 Uiso 1 1 calc R . . . .
C17 C 0.3629(3) 0.41145(9) 0.3001(3) 0.0168(4) Uani 1 1 d . . . . .
C18 C 0.2445(3) 0.37024(9) 0.2348(3) 0.0227(5) Uani 1 1 d . . . . .
H18 H 0.2720 0.3370 0.2858 0.027 Uiso 1 1 calc R . . . .
C19 C 0.0868(3) 0.37715(10) 0.0957(3) 0.0295(5) Uani 1 1 d . . . . .
H19 H 0.0087 0.3486 0.0515 0.035 Uiso 1 1 calc R . . . .
C20 C 0.0434(3) 0.42565(10) 0.0215(3) 0.0283(5) Uani 1 1 d . . . . .
H20 H -0.0644 0.4304 -0.0732 0.034 Uiso 1 1 calc R . . . .
C21 C 0.1577(3) 0.46680(10) 0.0862(3) 0.0246(5) Uani 1 1 d . . . . .
H21 H 0.1282 0.5002 0.0365 0.029 Uiso 1 1 calc R . . . .
C22 C 0.3165(3) 0.45984(9) 0.2242(3) 0.0198(4) Uani 1 1 d . . . . .
H22 H 0.3944 0.4886 0.2672 0.024 Uiso 1 1 calc R . . . .
P' P 0.87696(7) 0.72937(2) 0.03626(8) 0.02005(13) Uani 1 1 d . . . . .
O' O 0.8217(2) 0.74039(7) 0.1921(2) 0.0280(4) Uani 1 1 d . . . . .
C1' C 0.6420(3) 0.75942(10) 0.0814(4) 0.0327(6) Uani 1 1 d . . . . .
H1' H 0.648(4) 0.7982(13) 0.077(4) 0.039 Uiso 1 1 d R . . . .
C2' C 0.6334(3) 0.73403(10) -0.0759(3) 0.0277(5) Uani 1 1 d . . . . .
H2'A H 0.5919 0.7575 -0.1719 0.033 Uiso 1 1 calc R . . . .
H2'B H 0.5714 0.7001 -0.1027 0.033 Uiso 1 1 calc R . . . .
C3' C 0.5054(4) 0.74325(11) 0.1409(5) 0.0433(7) Uani 1 1 d . . . . .
H3'A H 0.5076 0.7053 0.1533 0.065 Uiso 1 1 calc GR . . . .
H3'B H 0.3876 0.7542 0.0616 0.065 Uiso 1 1 calc GR . . . .
H3'C H 0.5322 0.7597 0.2466 0.065 Uiso 1 1 calc GR . . . .
C4' C 0.9364(3) 0.65687(8) 0.0464(2) 0.0145(4) Uani 1 1 d . . . . .
C5' C 0.7884(3) 0.61985(8) 0.0356(3) 0.0152(4) Uani 1 1 d . . . . .
C6' C 0.7258(3) 0.62157(9) 0.1564(3) 0.0196(4) Uani 1 1 d . . . . .
H6' H 0.7736 0.6464 0.2421 0.024 Uiso 1 1 calc R . . . .
C7' C 0.5947(3) 0.58757(9) 0.1536(3) 0.0228(5) Uani 1 1 d . . . . .
H7' H 0.5525 0.5897 0.2360 0.027 Uiso 1 1 calc R . . . .
C8' C 0.5250(3) 0.55057(9) 0.0308(3) 0.0241(5) Uani 1 1 d . . . . .
H8' H 0.4351 0.5274 0.0286 0.029 Uiso 1 1 calc R . . . .
C9' C 0.5875(3) 0.54768(9) -0.0883(3) 0.0234(5) Uani 1 1 d . . . . .
H9' H 0.5414 0.5222 -0.1720 0.028 Uiso 1 1 calc R . . . .
C10' C 0.7181(3) 0.58206(9) -0.0862(3) 0.0185(4) Uani 1 1 d . . . . .
H10' H 0.7598 0.5797 -0.1689 0.022 Uiso 1 1 calc R . . . .
C11' C 1.1021(3) 0.64702(9) 0.2064(3) 0.0161(4) Uani 1 1 d . . . . .
C12' C 1.2197(3) 0.68654(9) 0.2910(3) 0.0216(4) Uani 1 1 d . . . . .
H12' H 1.1967 0.7212 0.2508 0.026 Uiso 1 1 calc R . . . .
C13' C 1.3708(3) 0.67595(10) 0.4337(3) 0.0270(5) Uani 1 1 d . . . . .
H13' H 1.4484 0.7035 0.4911 0.032 Uiso 1 1 calc R . . . .
C14' C 1.4080(3) 0.62559(10) 0.4918(3) 0.0263(5) Uani 1 1 d . . . . .
H14' H 1.5114 0.6183 0.5884 0.032 Uiso 1 1 calc R . . . .
C15' C 1.2942(3) 0.58600(9) 0.4088(3) 0.0225(5) Uani 1 1 d . . . . .
H15' H 1.3197 0.5513 0.4481 0.027 Uiso 1 1 calc R . . . .
C16' C 1.1418(3) 0.59645(9) 0.2674(3) 0.0187(4) Uani 1 1 d . . . . .
H16' H 1.0639 0.5688 0.2118 0.022 Uiso 1 1 calc R . . . .
C17' C 0.9788(3) 0.65313(8) -0.1030(3) 0.0152(4) Uani 1 1 d . . . . .
C18' C 1.1432(3) 0.63688(9) -0.0923(3) 0.0190(4) Uani 1 1 d . . . . .
H18' H 1.2332 0.6269 0.0106 0.023 Uiso 1 1 calc R . . . .
C19' C 1.1767(3) 0.63513(10) -0.2307(3) 0.0229(5) Uani 1 1 d . . . . .
H19' H 1.2891 0.6238 -0.2214 0.028 Uiso 1 1 calc R . . . .
C20' C 1.0472(3) 0.64979(9) -0.3823(3) 0.0215(4) Uani 1 1 d . . . . .
H20' H 1.0703 0.6485 -0.4765 0.026 Uiso 1 1 calc R . . . .
C21' C 0.8833(3) 0.66634(9) -0.3941(3) 0.0220(4) Uani 1 1 d . . . . .
H21' H 0.7937 0.6765 -0.4970 0.026 Uiso 1 1 calc R . . . .
C22' C 0.8503(3) 0.66808(9) -0.2573(3) 0.0193(4) Uani 1 1 d . . . . .
H22' H 0.7378 0.6797 -0.2674 0.023 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
P O 1.6719(18) . ?
P C2 1.855(2) . ?
P C4 1.926(2) . ?
O C1 1.486(3) . ?
C1 C2 1.542(4) . ?
C1 C3 1.504(4) . ?
C4 C5 1.527(3) . ?
C4 C11 1.532(3) . ?
C4 C17 1.547(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.400(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.382(4) . ?
C8 C9 1.385(3) . ?
C9 C10 1.387(3) . ?
C11 C12 1.403(3) . ?
C11 C16 1.394(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.388(4) . ?
C15 C16 1.386(4) . ?
C17 C18 1.395(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.388(4) . ?
C20 C21 1.376(3) . ?
C21 C22 1.393(3) . ?
P' O' 1.6799(19) . ?
P' C2' 1.848(2) . ?
P' C4' 1.918(2) . ?
O' C1' 1.487(3) . ?
C1' C2' 1.537(4) . ?
C1' C3' 1.508(4) . ?
C4' C5' 1.527(3) . ?
C4' C11' 1.540(3) . ?
C4' C17' 1.535(3) . ?
C5' C6' 1.396(3) . ?
C5' C10' 1.396(3) . ?
C6' C7' 1.390(3) . ?
C7' C8' 1.387(4) . ?
C8' C9' 1.381(4) . ?
C9' C10' 1.394(3) . ?
C11' C12' 1.392(3) . ?
C11' C16' 1.394(3) . ?
C12' C13' 1.396(3) . ?
C13' C14' 1.380(4) . ?
C14' C15' 1.376(3) . ?
C15' C16' 1.394(3) . ?
C17' C18' 1.395(3) . ?
C17' C22' 1.404(3) . ?
C18' C19' 1.393(3) . ?
C19' C20' 1.389(3) . ?
C20' C21' 1.390(3) . ?
C21' C22' 1.376(3) . ?

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
O P C2 80.31(10) . . ?
O P C4 104.98(9) . . ?
C2 P C4 104.66(10) . . ?
C1 O P 95.32(14) . . ?
O C1 C2 97.63(18) . . ?
O C1 C3 109.9(2) . . ?
C3 C1 C2 115.7(2) . . ?
C1 C2 P 86.45(15) . . ?
C5 C4 P 111.35(14) . . ?
C5 C4 C11 113.40(18) . . ?
C5 C4 C17 110.96(17) . . ?
C11 C4 P 104.19(14) . . ?
C11 C4 C17 109.85(17) . . ?
C17 C4 P 106.71(14) . . ?
C6 C5 C4 122.37(19) . . ?
C10 C5 C4 119.88(19) . . ?
C10 C5 C6 117.74(19) . . ?
C7 C6 C5 120.6(2) . . ?
C8 C7 C6 120.6(2) . . ?
C7 C8 C9 119.5(2) . . ?
C8 C9 C10 120.3(2) . . ?
C9 C10 C5 121.2(2) . . ?
C12 C11 C4 120.33(19) . . ?
C16 C11 C4 122.35(19) . . ?
C16 C11 C12 117.3(2) . . ?
C13 C12 C11 121.5(2) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 C15 119.2(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C11 121.2(2) . . ?
C18 C17 C4 121.23(19) . . ?
C22 C17 C4 120.62(19) . . ?
C22 C17 C18 118.0(2) . . ?
C19 C18 C17 120.9(2) . . ?
C20 C19 C18 120.3(2) . . ?
C21 C20 C19 119.4(2) . . ?
C20 C21 C22 120.4(2) . . ?
C17 C22 C21 121.1(2) . . ?
O' P' C2' 79.74(11) . . ?
O' P' C4' 106.28(9) . . ?
C2' P' C4' 106.87(11) . . ?
C1' O' P' 92.69(15) . . ?
O' C1' C2' 97.00(18) . . ?
O' C1' C3' 111.5(2) . . ?
C3' C1' C2' 117.8(2) . . ?
C1' C2' P' 84.83(15) . . ?
C5' C4' P' 114.57(14) . . ?
C5' C4' C11' 109.65(17) . . ?
C5' C4' C17' 112.63(17) . . ?
C11' C4' P' 108.35(14) . . ?
C17' C4' P' 99.77(14) . . ?
C17' C4' C11' 111.53(17) . . ?
C6' C5' C4' 119.30(19) . . ?
C10' C5' C4' 122.77(19) . . ?
C10' C5' C6' 117.85(19) . . ?
C7' C6' C5' 121.1(2) . . ?
C8' C7' C6' 120.3(2) . . ?
C9' C8' C7' 119.4(2) . . ?
C8' C9' C10' 120.3(2) . . ?
C9' C10' C5' 121.0(2) . . ?
C12' C11' C4' 122.6(2) . . ?
C12' C11' C16' 117.9(2) . . ?
C16' C11' C4' 119.51(19) . . ?
C11' C12' C13' 121.0(2) . . ?
C14' C13' C12' 120.2(2) . . ?
C15' C14' C13' 119.5(2) . . ?
C14' C15' C16' 120.5(2) . . ?
C15' C16' C11' 120.9(2) . . ?
C18' C17' C4' 122.8(2) . . ?
C18' C17' C22' 117.6(2) . . ?
C22' C17' C4' 119.54(18) . . ?
C19' C18' C17' 120.7(2) . . ?
C20' C19' C18' 120.6(2) . . ?
C19' C20' C21' 119.1(2) . . ?
C22' C21' C20' 120.3(2) . . ?
C21' C22' C17' 121.6(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
