# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_z
_audit_block_doi                 10.5517/ccdc.csd.cc1p36zz
_database_code_depnum_ccdc_archive 'CCDC 1552231'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N3 P'
_chemical_formula_weight         431.46

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   R3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   34.841(3)
_cell_length_b                   34.841(3)
_cell_length_c                   5.5660(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5851.2(9)
_cell_formula_units_Z            9
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3638
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      19.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2034
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22882
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4512
_reflns_number_gt                3418
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0673P)²+0.3278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4512
_refine_ls_number_parameters     289
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.86106(3) 0.71559(3) 0.94006(16) 0.0580(2) Uani 1 1 d . . .
N1 N 0.81486(8) 0.59254(9) 1.1637(5) 0.0540(6) Uani 1 1 d . . .
N2 N 0.81903(10) 0.58918(10) 0.9262(5) 0.0690(8) Uani 1 1 d . . .
N3 N 0.83433(10) 0.62935(10) 0.8359(5) 0.0665(8) Uani 1 1 d . . .
C1 C 0.91165(9) 0.74384(10) 1.1226(6) 0.0498(7) Uani 1 1 d . . .
C2 C 0.91538(10) 0.77034(11) 1.3126(6) 0.0608(9) Uani 1 1 d . . .
H2A H 0.8911 0.7731 1.3573 0.073 Uiso 1 1 calc R . .
C3 C 0.95540(12) 0.79360(12) 1.4420(7) 0.0701(10) Uani 1 1 d . . .
H3A H 0.9574 0.8120 1.5684 0.084 Uiso 1 1 calc R . .
C4 C 0.99069(12) 0.78943(11) 1.3843(7) 0.0625(8) Uani 1 1 d . . .
H4A H 1.0167 0.8045 1.4732 0.075 Uiso 1 1 calc R . .
C5 C 0.98862(9) 0.76242(9) 1.1908(6) 0.0490(7) Uani 1 1 d . . .
C6 C 0.94906(9) 0.73953(9) 1.0539(5) 0.0476(7) Uani 1 1 d . . .
C7 C 0.94890(11) 0.71420(10) 0.8549(6) 0.0546(8) Uani 1 1 d . . .
H7A H 0.9235 0.6994 0.7609 0.065 Uiso 1 1 calc R . .
C8 C 0.98535(11) 0.71123(12) 0.7990(6) 0.0622(8) Uani 1 1 d . . .
H8A H 0.9847 0.6947 0.6664 0.075 Uiso 1 1 calc R . .
C9 C 1.02402(11) 0.73287(12) 0.9390(7) 0.0659(9) Uani 1 1 d . . .
H9A H 1.0485 0.7302 0.9006 0.079 Uiso 1 1 calc R . .
C10 C 1.02551(10) 0.75762(10) 1.1295(6) 0.0572(8) Uani 1 1 d . . .
H10A H 1.0511 0.7717 1.2220 0.069 Uiso 1 1 calc R . .
C11 C 0.82470(12) 0.72585(12) 1.1119(7) 0.0686(10) Uani 1 1 d . . .
C12 C 0.79758(11) 0.73359(11) 1.1890(7) 0.0670(9) Uani 1 1 d . . .
C13 C 0.76719(10) 0.74356(10) 1.3064(6) 0.0567(8) Uani 1 1 d . . .
C14 C 0.72609(13) 0.72919(16) 1.2117(9) 0.0939(14) Uani 1 1 d . . .
H14A H 0.7172 0.7123 1.0721 0.113 Uiso 1 1 calc R . .
C15 C 0.69751(17) 0.74052(18) 1.3298(10) 0.1111(11) Uani 1 1 d U . .
H15A H 0.6692 0.7307 1.2691 0.133 Uiso 1 1 calc R . .
C16 C 0.71069(17) 0.76543(18) 1.5299(10) 0.1090(11) Uani 1 1 d U . .
H16A H 0.6920 0.7738 1.6029 0.131 Uiso 1 1 calc R . .
C17 C 0.75004(16) 0.77808(17) 1.6233(10) 0.1106(11) Uani 1 1 d U . .
H17A H 0.7584 0.7945 1.7646 0.133 Uiso 1 1 calc R . .
C18 C 0.77836(14) 0.76745(13) 1.5158(8) 0.0828(11) Uani 1 1 d . . .
H18A H 0.8059 0.7765 1.5854 0.099 Uiso 1 1 calc R . .
C19 C 0.83999(10) 0.65752(11) 1.0129(5) 0.0504(8) Uani 1 1 d . . .
C20 C 0.82748(10) 0.63392(10) 1.2251(6) 0.0542(8) Uani 1 1 d . . .
H20A H 0.8278 0.6447 1.3784 0.065 Uiso 1 1 calc R . .
C21 C 0.79834(12) 0.55237(12) 1.3124(6) 0.0649(9) Uani 1 1 d . . .
H21A H 0.8032 0.5609 1.4804 0.078 Uiso 1 1 calc R . .
H21B H 0.8152 0.5379 1.2756 0.078 Uiso 1 1 calc R . .
C22 C 0.74994(11) 0.52007(10) 1.2734(6) 0.0588(8) Uani 1 1 d . . .
C23 C 0.73621(13) 0.49340(13) 1.0741(8) 0.0832(12) Uani 1 1 d . . .
H23A H 0.7570 0.4949 0.9638 0.100 Uiso 1 1 calc R . .
C24 C 0.69190(15) 0.46439(15) 1.0362(8) 0.0926(13) Uani 1 1 d . . .
H24A H 0.6832 0.4465 0.9000 0.111 Uiso 1 1 calc R . .
C25 C 0.66071(13) 0.46120(14) 1.1921(9) 0.0818(12) Uani 1 1 d . . .
C26 C 0.67482(15) 0.48770(15) 1.3887(9) 0.0900(13) Uani 1 1 d . . .
H26A H 0.6541 0.4857 1.5005 0.108 Uiso 1 1 calc R . .
C27 C 0.71828(14) 0.51697(13) 1.4270(8) 0.0740(10) Uani 1 1 d . . .
H27A H 0.7266 0.5353 1.5613 0.089 Uiso 1 1 calc R . .
C28 C 0.61137(15) 0.42915(18) 1.1413(13) 0.132(2) Uani 1 1 d . . .
H28A H 0.6084 0.4137 0.9934 0.199 Uiso 1 1 calc R . .
H28B H 0.5961 0.4456 1.1286 0.199 Uiso 1 1 calc R . .
H28C H 0.5988 0.4081 1.2702 0.199 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C11 1.761(4) . ?
P1 C19 1.820(3) . ?
P1 C1 1.836(3) . ?
N1 C20 1.325(4) . ?
N1 N2 1.342(4) . ?
N1 C21 1.473(4) . ?
N2 N3 1.323(4) . ?
N3 C19 1.334(4) . ?
C1 C2 1.367(4) . ?
C1 C6 1.436(4) . ?
C2 C3 1.411(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.347(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.408(5) . ?
C4 H4A 0.9300 . ?
C5 C10 1.418(4) . ?
C5 C6 1.420(4) . ?
C6 C7 1.415(4) . ?
C7 C8 1.361(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.405(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.351(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.185(4) . ?
C12 C13 1.427(5) . ?
C13 C14 1.365(5) . ?
C13 C18 1.371(5) . ?
C14 C15 1.404(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.344(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.319(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.354(6) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.380(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.503(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C27 1.356(5) . ?
C22 C23 1.371(5) . ?
C23 C24 1.374(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.351(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.356(6) . ?
C25 C28 1.537(6) . ?
C26 C27 1.354(6) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 P1 C19 99.99(15) . . ?
C11 P1 C1 100.72(16) . . ?
C19 P1 C1 102.60(14) . . ?
C20 N1 N2 111.0(3) . . ?
C20 N1 C21 130.4(3) . . ?
N2 N1 C21 118.6(3) . . ?
N3 N2 N1 106.6(2) . . ?
N2 N3 C19 109.3(3) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 P1 122.1(2) . . ?
C6 C1 P1 118.3(2) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C10 121.1(3) . . ?
C4 C5 C6 119.8(3) . . ?
C10 C5 C6 119.1(3) . . ?
C7 C6 C5 118.1(3) . . ?
C7 C6 C1 123.6(3) . . ?
C5 C6 C1 118.4(3) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10A 119.5 . . ?
C5 C10 H10A 119.5 . . ?
C12 C11 P1 168.3(4) . . ?
C11 C12 C13 173.8(4) . . ?
C14 C13 C18 118.6(4) . . ?
C14 C13 C12 120.3(3) . . ?
C18 C13 C12 121.1(3) . . ?
C13 C14 C15 118.5(4) . . ?
C13 C14 H14A 120.7 . . ?
C15 C14 H14A 120.7 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 120.8(5) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C17 C18 C13 121.1(4) . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
N3 C19 C20 107.9(3) . . ?
N3 C19 P1 118.9(2) . . ?
C20 C19 P1 133.2(2) . . ?
N1 C20 C19 105.2(3) . . ?
N1 C20 H20A 127.4 . . ?
C19 C20 H20A 127.4 . . ?
N1 C21 C22 112.9(3) . . ?
N1 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N1 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C27 C22 C23 117.5(3) . . ?
C27 C22 C21 122.1(3) . . ?
C23 C22 C21 120.3(3) . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C25 C24 C23 121.6(4) . . ?
C25 C24 H24A 119.2 . . ?
C23 C24 H24A 119.2 . . ?
C24 C25 C26 117.4(4) . . ?
C24 C25 C28 120.2(5) . . ?
C26 C25 C28 122.4(5) . . ?
C27 C26 C25 121.9(4) . . ?
C27 C26 H26A 119.1 . . ?
C25 C26 H26A 119.1 . . ?
C26 C27 C22 121.3(4) . . ?
C26 C27 H27A 119.4 . . ?
C22 C27 H27A 119.4 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 N1 N2 N3 -0.5(3) . . . . ?
C21 N1 N2 N3 -179.9(3) . . . . ?
N1 N2 N3 C19 0.4(3) . . . . ?
C11 P1 C1 C2 -9.3(3) . . . . ?
C19 P1 C1 C2 -112.2(3) . . . . ?
C11 P1 C1 C6 174.0(2) . . . . ?
C19 P1 C1 C6 71.1(2) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
P1 C1 C2 C3 -176.5(3) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C10 -179.6(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C7 177.4(3) . . . . ?
C10 C5 C6 C7 -2.6(4) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C10 C5 C6 C1 178.3(3) . . . . ?
C2 C1 C6 C7 -177.7(3) . . . . ?
P1 C1 C6 C7 -0.9(4) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
P1 C1 C6 C5 178.2(2) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C1 C6 C7 C8 -179.8(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C5 -0.3(5) . . . . ?
C4 C5 C10 C9 -177.8(3) . . . . ?
C6 C5 C10 C9 2.2(5) . . . . ?
C19 P1 C11 C12 -113.1(16) . . . . ?
C1 P1 C11 C12 141.9(16) . . . . ?
P1 C11 C12 C13 -167(2) . . . . ?
C11 C12 C13 C14 -157(3) . . . . ?
C11 C12 C13 C18 23(4) . . . . ?
C18 C13 C14 C15 1.6(7) . . . . ?
C12 C13 C14 C15 -178.6(4) . . . . ?
C13 C14 C15 C16 0.8(8) . . . . ?
C14 C15 C16 C17 -2.7(9) . . . . ?
C15 C16 C17 C18 2.0(8) . . . . ?
C16 C17 C18 C13 0.5(7) . . . . ?
C14 C13 C18 C17 -2.3(6) . . . . ?
C12 C13 C18 C17 177.9(4) . . . . ?
N2 N3 C19 C20 -0.2(4) . . . . ?
N2 N3 C19 P1 179.8(2) . . . . ?
C11 P1 C19 N3 135.0(3) . . . . ?
C1 P1 C19 N3 -121.5(3) . . . . ?
C11 P1 C19 C20 -44.9(3) . . . . ?
C1 P1 C19 C20 58.5(3) . . . . ?
N2 N1 C20 C19 0.3(3) . . . . ?
C21 N1 C20 C19 179.6(3) . . . . ?
N3 C19 C20 N1 -0.1(3) . . . . ?
P1 C19 C20 N1 179.9(2) . . . . ?
C20 N1 C21 C22 109.8(4) . . . . ?
N2 N1 C21 C22 -71.0(4) . . . . ?
N1 C21 C22 C27 -100.2(4) . . . . ?
N1 C21 C22 C23 77.7(4) . . . . ?
C27 C22 C23 C24 -0.9(6) . . . . ?
C21 C22 C23 C24 -178.9(4) . . . . ?
C22 C23 C24 C25 0.0(7) . . . . ?
C23 C24 C25 C26 -0.2(7) . . . . ?
C23 C24 C25 C28 178.6(4) . . . . ?
C24 C25 C26 C27 1.3(7) . . . . ?
C28 C25 C26 C27 -177.5(4) . . . . ?
C25 C26 C27 C22 -2.2(6) . . . . ?
C23 C22 C27 C26 1.9(5) . . . . ?
C21 C22 C27 C26 179.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.030

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.047 276 95 ' '
2 0.333 0.667 0.882 276 95 ' '
3 0.667 0.333 0.549 277 95 ' '
_platon_squeeze_details          
;
;

####################################################################### 
# 
# 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_z_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc1mm68q
_database_code_depnum_ccdc_archive 'CCDC 1508003'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N3 O P'
_chemical_formula_weight         334.33

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.0625(7)
_cell_length_b                   10.9721(8)
_cell_length_c                   18.2236(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1812.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5897
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      22.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9324
_exptl_absorpt_correction_T_max  0.9517
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21121
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3182
_reflns_number_gt                2677
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0834P)²+0.2975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3182
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.72166(8) 0.16395(7) 0.82108(4) 0.0553(2) Uani 1 1 d . . .
O1 O 0.6395(3) 0.2752(2) 0.80191(14) 0.0815(7) Uani 1 1 d . . .
N1 N 1.1082(3) 0.1197(2) 0.72992(13) 0.0618(7) Uani 1 1 d . . .
N2 N 1.1188(4) 0.2335(3) 0.75568(17) 0.0764(8) Uani 1 1 d . . .
N3 N 0.9928(3) 0.2580(2) 0.78805(15) 0.0660(7) Uani 1 1 d . . .
C1 C 0.8178(3) 0.0554(3) 0.95388(17) 0.0647(8) Uani 1 1 d . . .
C2 C 0.8197(5) 0.0564(4) 1.0305(2) 0.0921(12) Uani 1 1 d . . .
H2A H 0.8755 -0.0015 1.0553 0.111 Uiso 1 1 calc R . .
C3 C 0.7421(5) 0.1398(4) 1.0696(2) 0.0999(13) Uani 1 1 d . . .
H3A H 0.7439 0.1368 1.1205 0.120 Uiso 1 1 calc R . .
C4 C 0.6618(6) 0.2276(4) 1.0354(2) 0.1016(14) Uani 1 1 d . . .
H4A H 0.6096 0.2848 1.0627 0.122 Uiso 1 1 calc R . .
C5 C 0.6588(4) 0.2305(3) 0.9601(2) 0.0813(10) Uani 1 1 d . . .
H5A H 0.6035 0.2901 0.9364 0.098 Uiso 1 1 calc R . .
C6 C 0.7378(3) 0.1452(3) 0.91849(16) 0.0567(7) Uani 1 1 d . . .
C7 C 0.9043(5) -0.0402(4) 0.9132(2) 0.0858(11) Uani 1 1 d . . .
H7A H 0.8923 -0.0284 0.8613 0.129 Uiso 1 1 calc R . .
H7B H 0.8688 -0.1196 0.9265 0.129 Uiso 1 1 calc R . .
H7C H 1.0068 -0.0334 0.9257 0.129 Uiso 1 1 calc R . .
C8 C 0.6438(4) 0.0309(3) 0.78661(18) 0.0673(8) Uani 1 1 d . . .
C9 C 0.5842(4) -0.0546(4) 0.7610(2) 0.0822(10) Uani 1 1 d . . .
H9A H 0.5234 -0.1304 0.7324 0.099 Uiso 1 1 d R . .
C10 C 0.9029(3) 0.1609(3) 0.78164(14) 0.0525(6) Uani 1 1 d . . .
C11 C 0.9756(4) 0.0732(3) 0.74379(17) 0.0603(8) Uani 1 1 d . . .
H11A H 0.9404 -0.0032 0.7304 0.072 Uiso 1 1 calc R . .
C12 C 1.2339(4) 0.0651(4) 0.69057(19) 0.0810(10) Uani 1 1 d . . .
H12A H 1.2304 -0.0227 0.6963 0.097 Uiso 1 1 calc R . .
H12B H 1.3251 0.0938 0.7124 0.097 Uiso 1 1 calc R . .
C13 C 1.2341(4) 0.0958(3) 0.61014(18) 0.0646(8) Uani 1 1 d . . .
C14 C 1.1522(5) 0.0298(4) 0.5613(2) 0.0917(11) Uani 1 1 d . . .
H14A H 1.0961 -0.0359 0.5775 0.110 Uiso 1 1 calc R . .
C15 C 1.1529(6) 0.0608(5) 0.4876(3) 0.1097(14) Uani 1 1 d U . .
H15A H 1.0969 0.0146 0.4552 0.132 Uiso 1 1 calc R . .
C16 C 1.2321(5) 0.1561(5) 0.4608(2) 0.0942(12) Uani 1 1 d U . .
C17 C 1.3142(5) 0.2191(4) 0.5098(3) 0.0941(13) Uani 1 1 d . . .
H17A H 1.3713 0.2841 0.4935 0.113 Uiso 1 1 calc R . .
C18 C 1.3158(4) 0.1898(4) 0.5837(2) 0.0782(10) Uani 1 1 d . . .
H18A H 1.3737 0.2352 0.6158 0.094 Uiso 1 1 calc R . .
C19 C 1.2323(7) 0.1889(8) 0.3804(3) 0.164(3) Uani 1 1 d . . .
H19A H 1.2942 0.2587 0.3727 0.246 Uiso 1 1 calc R . .
H19B H 1.1335 0.2075 0.3651 0.246 Uiso 1 1 calc R . .
H19C H 1.2692 0.1214 0.3524 0.246 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.472(2) . ?
P1 C8 1.739(4) . ?
P1 C10 1.793(3) . ?
P1 C6 1.793(3) . ?
N1 C11 1.330(4) . ?
N1 N2 1.336(4) . ?
N1 C12 1.473(4) . ?
N2 N3 1.313(4) . ?
N3 C10 1.347(4) . ?
C1 C6 1.383(4) . ?
C1 C2 1.396(5) . ?
C1 C7 1.505(5) . ?
C2 C3 1.356(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.358(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.179(5) . ?
C9 H9A 1.1258 . ?
C10 C11 1.355(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.358(5) . ?
C13 C14 1.366(5) . ?
C14 C15 1.385(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.359(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.353(7) . ?
C16 C19 1.507(6) . ?
C17 C18 1.384(6) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C8 113.90(15) . . ?
O1 P1 C10 112.56(15) . . ?
C8 P1 C10 102.20(15) . . ?
O1 P1 C6 111.79(14) . . ?
C8 P1 C6 107.12(15) . . ?
C10 P1 C6 108.68(13) . . ?
C11 N1 N2 110.9(3) . . ?
C11 N1 C12 129.4(3) . . ?
N2 N1 C12 119.7(3) . . ?
N3 N2 N1 106.7(3) . . ?
N2 N3 C10 109.0(2) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 C7 122.7(3) . . ?
C2 C1 C7 119.5(3) . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 H2A 119.2 . . ?
C1 C2 H2A 119.2 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 P1 125.9(2) . . ?
C5 C6 P1 114.7(2) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 175.7(3) . . ?
C8 C9 H9A 174.5 . . ?
N3 C10 C11 108.1(3) . . ?
N3 C10 P1 120.3(2) . . ?
C11 C10 P1 131.5(2) . . ?
N1 C11 C10 105.3(3) . . ?
N1 C11 H11A 127.3 . . ?
C10 C11 H11A 127.3 . . ?
N1 C12 C13 112.6(3) . . ?
N1 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C18 C13 C14 117.9(3) . . ?
C18 C13 C12 121.1(3) . . ?
C14 C13 C12 121.1(3) . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 122.7(4) . . ?
C16 C15 H15A 118.6 . . ?
C14 C15 H15A 118.6 . . ?
C17 C16 C15 116.4(4) . . ?
C17 C16 C19 121.3(5) . . ?
C15 C16 C19 122.3(5) . . ?
C16 C17 C18 122.0(4) . . ?
C16 C17 H17A 119.0 . . ?
C18 C17 H17A 119.0 . . ?
C13 C18 C17 121.1(4) . . ?
C13 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 N2 N3 1.7(3) . . . . ?
C12 N1 N2 N3 -179.8(3) . . . . ?
N1 N2 N3 C10 -0.9(3) . . . . ?
C6 C1 C2 C3 2.1(6) . . . . ?
C7 C1 C2 C3 -179.2(4) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C7 C1 C6 C5 179.4(3) . . . . ?
C2 C1 C6 P1 178.9(3) . . . . ?
C7 C1 C6 P1 0.2(5) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 P1 -179.6(3) . . . . ?
O1 P1 C6 C1 -174.7(3) . . . . ?
C8 P1 C6 C1 59.8(3) . . . . ?
C10 P1 C6 C1 -49.9(3) . . . . ?
O1 P1 C6 C5 6.0(3) . . . . ?
C8 P1 C6 C5 -119.4(3) . . . . ?
C10 P1 C6 C5 130.9(3) . . . . ?
O1 P1 C8 C9 3(5) . . . . ?
C10 P1 C8 C9 -119(5) . . . . ?
C6 P1 C8 C9 127(5) . . . . ?
N2 N3 C10 C11 -0.2(3) . . . . ?
N2 N3 C10 P1 179.3(2) . . . . ?
O1 P1 C10 N3 49.0(3) . . . . ?
C8 P1 C10 N3 171.6(2) . . . . ?
C6 P1 C10 N3 -75.4(2) . . . . ?
O1 P1 C10 C11 -131.7(3) . . . . ?
C8 P1 C10 C11 -9.1(3) . . . . ?
C6 P1 C10 C11 103.9(3) . . . . ?
N2 N1 C11 C10 -1.8(3) . . . . ?
C12 N1 C11 C10 179.9(3) . . . . ?
N3 C10 C11 N1 1.2(3) . . . . ?
P1 C10 C11 N1 -178.2(2) . . . . ?
C11 N1 C12 C13 92.3(4) . . . . ?
N2 N1 C12 C13 -85.9(4) . . . . ?
N1 C12 C13 C18 96.3(4) . . . . ?
N1 C12 C13 C14 -83.8(4) . . . . ?
C18 C13 C14 C15 -0.9(6) . . . . ?
C12 C13 C14 C15 179.2(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 1.3(7) . . . . ?
C14 C15 C16 C19 179.9(5) . . . . ?
C15 C16 C17 C18 -1.1(6) . . . . ?
C19 C16 C17 C18 -179.7(4) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
C12 C13 C18 C17 -179.0(4) . . . . ?
C16 C17 C18 C13 -0.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_855
_database_code_depnum_ccdc_archive 'CCDC 1920853'
loop_
_audit_author_name
_audit_author_address
'Zhu renyi'
;East China normal university
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 O3 P'
_chemical_formula_sum            'C19 H23 O3 P'
_chemical_formula_weight         330.34
_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 0.0180 0.0090 '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 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2950 0.4340 '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                   8.3114(2)
_cell_length_b                   10.1411(2)
_cell_length_c                   10.8128(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.963(2)
_cell_angle_gamma                90
_cell_volume                     866.95(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24096
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1870
_cell_measurement_theta_min      4.0630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21852
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.524
_diffrn_reflns_theta_min         4.298
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  21.00   1.00    1.00    --    0.00  82.00  90.00   38
  2  ω     25.00  89.00   1.00    1.00    --    0.00  77.00 -60.00   64
  3  ω    -22.00  52.00   1.00    1.00    --    0.00  57.00-120.00   74
  4  ω     45.00  88.00   1.00    1.00    --    0.00  19.00  30.00   43
  5  ω    -23.00  52.00   1.00    1.00    --    0.00  19.00-150.00   75
  6  ω    -21.00  19.00   1.00    1.00    --    0.00  19.00  30.00   40
  7  ω    -22.00  63.00   1.00    1.00    --    0.00  19.00 -90.00   85
  8  ω    -18.00  62.00   1.00    1.00    --    0.00  38.00 -30.00   80
  9  ω    -19.00  59.00   1.00    1.00    --    0.00  38.00  90.00   78
 10  ω     26.00  84.00   1.00    1.00    --    0.00  82.00  90.00   58
 11  ω     60.00  89.00   1.00    1.00    --    0.00  57.00-120.00   29
 12  ω     10.00  59.00   1.00    1.00    --    0.00  38.00 150.00   49
 13  ω     65.00  96.00   1.00    1.00    --   95.80  79.00  71.70   31
 14  ω    134.00 160.00   1.00    1.00    --   95.80  50.00  24.02   26
 15  ω     64.00  90.00   1.00    1.00    --   95.80  80.00  47.18   26
 16  ω     74.00 100.00   1.00    1.00    --   95.80  50.00  24.02   26
 17  ω    108.00 180.00   1.00    1.00    --   95.80  68.00-112.96   72
 18  ω     68.00 137.00   1.00    1.00    --   95.80  68.00 126.44   69
 19  ω     69.00 107.00   1.00    1.00    --   95.80  66.00 -57.14   38
 20  ω     72.00 184.00   1.00    1.00    --   95.80  61.00 -30.00  112
 21  ω    132.00 157.00   1.00    1.00    --   95.80  61.00-120.00   25
 22  ω     68.00  98.00   1.00    1.00    --   95.80  68.00-112.96   30
 23  ω     64.00  90.00   1.00    1.00    --   95.80  82.00  90.00   26
 24  ω     71.00 106.00   1.00    1.00    --   95.80  61.00 -90.00   35
 25  ω    129.00 155.00   1.00    1.00    --   95.80  61.00 -90.00   26
 26  ω     66.00  92.00   1.00    1.00    --   95.80  77.00-180.00   26
 27  ω    123.00 185.00   1.00    1.00    --   95.80  77.00-180.00   62
 28  ω     14.00  39.00   1.00    1.00    --   95.80 -82.00 120.00   25
 29  ω     45.00  73.00   1.00    1.00    --   95.80 -82.00 120.00   28
 30  ω     79.00 128.00   1.00    1.00    --   95.80 -82.00 120.00   49
 31  ω     71.00 104.00   1.00    1.00    --   95.80  61.00-120.00   33
 32  ω     70.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   57
 33  ω     63.00 184.00   1.00    1.00    --   95.80  82.00 128.92  121
 34  ω    160.00 185.00   1.00    1.00    --   95.80  66.00 -57.14   25
 35  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 36  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 37  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 38  ω    144.00 170.00   1.00    1.00    --   95.80  77.00 150.00   26
 39  ω     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 40  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 41  ω     57.00 127.00   1.00    1.00    --   95.80 -82.00  60.00   70
 42  ω     68.00  97.00   1.00    1.00    --   95.80  69.00-177.03   29
 43  ω     65.00 185.00   1.00    1.00    --   95.80  77.00  90.00  120
 44  ω    141.00 167.00   1.00    1.00    --   95.80  78.00 -80.17   26
 45  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 46  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 47  ω     78.00 181.00   1.00    1.00    --   95.80  45.00 -60.00  103
 48  ω     66.00  91.00   1.00    1.00    --   95.80  77.00 120.00   25
 49  ω    146.00 171.00   1.00    1.00    --   95.80  77.00 120.00   25
 50  ω     66.00  92.00   1.00    1.00    --   95.80  82.00   0.00   26
 51  ω    115.00 184.00   1.00    1.00    --   95.80  82.00   0.00   69
 52  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 53  ω      8.00  34.00   1.00    1.00    --   95.80 -82.00-150.00   26
 54  ω     47.00  72.00   1.00    1.00    --   95.80 -82.00-150.00   25
 55  ω     81.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   47
 56  ω     68.00  94.00   1.00    1.00    --   95.80  82.00-150.00   26
 57  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 58  ω     78.00 103.00   1.00    1.00    --   95.80  45.00   0.00   25
 59  ω    137.00 162.00   1.00    1.00    --   95.80  45.00   0.00   25
 60  ω     68.00 185.00   1.00    1.00    --   95.80  69.00-154.81  117
 61  ω     96.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   31
 62  ω     65.00 140.00   1.00    1.00    --   95.80  77.00 150.00   75
 63  ω      6.00 118.00   1.00    1.00    --   95.80 -77.00 -90.00  112
 64  ω     65.00  90.00   1.00    1.00    --   95.80  78.00 -80.17   25
 65  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 66  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 67  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 68  ω     79.00 118.00   1.00    1.00    --   95.80  30.00  30.00   39
 69  ω     75.00 137.00   1.00    1.00    --   95.80  45.00  90.00   62
 70  ω    129.00 169.00   1.00    1.00    --   95.80  79.00  71.70   40
 71  ω    121.00 167.00   1.00    1.00    --   95.80  80.00  47.18   46
 72  ω    122.00 147.00   1.00    1.00    --   95.80  66.00 -57.14   25
 73  ω     71.00 104.00   1.00    1.00    --   95.80  61.00  24.72   33
 74  ω     74.00 100.00   1.00    1.00    --   95.80  52.00  52.55   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1213467000
_diffrn_orient_matrix_UB_12      0.0462152000
_diffrn_orient_matrix_UB_13      0.0149931000
_diffrn_orient_matrix_UB_21      -0.0609873000
_diffrn_orient_matrix_UB_22      -0.0120368000
_diffrn_orient_matrix_UB_23      -0.1009503000
_diffrn_orient_matrix_UB_31      -0.0339541000
_diffrn_orient_matrix_UB_32      -0.1443073000
_diffrn_orient_matrix_UB_33      0.0132553000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                3395
_reflns_number_total             3414
_reflns_odcompleteness_completeness 99.97
_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.
 
 _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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.247
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.3928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0876
_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. Restrained distances
 C182-C192
 1.52 with sigma of 0.01
 C191-C181
 1.52 with sigma of 0.01
 C181-C191
 1.52 with sigma of 0.01
3. Others
 Fixed Sof: C182(0.5) H18A(0.5) H18B(0.5) C192(0.5) H19A(0.5) H19B(0.5)
 H19C(0.5) C191(0.5) H19D(0.5) H19E(0.5) H19F(0.5) C181(0.5) H18C(0.5) H18D(0.5)
4.a Ternary CH refined with riding coordinates:
 C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C182(H18A,H18B), C181(H18C,H18D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C192(H19A,H19B,H19C), C191(H19D,
 H19E,H19F)
;
_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 0.26281(7) 0.02325(7) 0.38020(5) 0.01686(15) Uani 1 1 d . . . . .
O1 O 0.3861(2) 0.10310(19) 0.33804(18) 0.0235(4) Uani 1 1 d . . . . .
O2 O 0.3633(3) 0.0418(2) 0.82305(18) 0.0337(5) Uani 1 1 d . . . . .
O3 O 0.3561(4) 0.2601(3) 0.8058(2) 0.0548(8) Uani 1 1 d . . . . .
C1 C 0.0555(3) 0.0993(3) 0.3351(2) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.0408(4) 0.2285(3) 0.2880(3) 0.0263(6) Uani 1 1 d . . . . .
H2 H 0.135550 0.273339 0.281710 0.032 Uiso 1 1 calc R . . . .
C3 C -0.1168(4) 0.2895(4) 0.2507(3) 0.0352(7) Uani 1 1 d . . . . .
H3 H -0.127387 0.375606 0.219628 0.042 Uiso 1 1 calc R . . . .
C4 C -0.2572(4) 0.2228(4) 0.2594(3) 0.0377(8) Uani 1 1 d . . . . .
H4 H -0.362414 0.263815 0.233058 0.045 Uiso 1 1 calc R . . . .
C5 C -0.2429(4) 0.0950(4) 0.3072(4) 0.0414(8) Uani 1 1 d . . . . .
H5 H -0.337989 0.050779 0.313677 0.050 Uiso 1 1 calc R . . . .
C6 C -0.0856(3) 0.0331(4) 0.3456(3) 0.0320(6) Uani 1 1 d . . . . .
H6 H -0.075326 -0.052477 0.378110 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2191(3) -0.1406(3) 0.3095(2) 0.0208(5) Uani 1 1 d . . . . .
C8 C 0.1768(3) -0.2432(3) 0.3793(3) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.179909 -0.228936 0.464997 0.028 Uiso 1 1 calc R . . . .
C9 C 0.1301(4) -0.3666(3) 0.3236(3) 0.0289(6) Uani 1 1 d . . . . .
H9 H 0.100043 -0.433555 0.371000 0.035 Uiso 1 1 calc R . . . .
C10 C 0.1288(4) -0.3887(3) 0.1976(3) 0.0369(7) Uani 1 1 d . . . . .
H10 H 0.098875 -0.471022 0.159650 0.044 Uiso 1 1 calc R . . . .
C11 C 0.1723(5) -0.2878(4) 0.1278(3) 0.0428(8) Uani 1 1 d . . . . .
H11 H 0.171996 -0.304263 0.043157 0.051 Uiso 1 1 calc R . . . .
C12 C 0.2165(4) -0.1623(3) 0.1800(3) 0.0308(6) Uani 1 1 d . . . . .
C13 C 0.2518(7) -0.0542(4) 0.0966(3) 0.0544(11) Uani 1 1 d . . . . .
H13A H 0.170830 0.015457 0.088062 0.082 Uiso 1 1 calc GR . . . .
H13B H 0.243199 -0.088767 0.012132 0.082 Uiso 1 1 calc GR . . . .
H13C H 0.363696 -0.020328 0.136286 0.082 Uiso 1 1 calc GR . . . .
C14 C 0.3299(3) 0.0045(3) 0.5568(2) 0.0205(5) Uani 1 1 d . . . . .
H14 H 0.244658 -0.046201 0.582056 0.025 Uiso 1 1 calc R . . . .
C15 C 0.4991(3) -0.0695(3) 0.6000(3) 0.0257(6) Uani 1 1 d . . . . .
H15A H 0.480734 -0.160556 0.575302 0.039 Uiso 1 1 calc GR . . . .
H15B H 0.547305 -0.063242 0.692674 0.039 Uiso 1 1 calc GR . . . .
H15C H 0.575218 -0.031079 0.558957 0.039 Uiso 1 1 calc GR . . . .
C16 C 0.3445(4) 0.1431(3) 0.6167(3) 0.0239(6) Uani 1 1 d . . . . .
H16A H 0.443995 0.186454 0.606992 0.029 Uiso 1 1 calc R . . . .
H16B H 0.246364 0.194668 0.569760 0.029 Uiso 1 1 calc R . . . .
C17 C 0.3570(4) 0.1396(3) 0.7594(3) 0.0253(6) Uani 1 1 d . . . . .
C182 C 0.3361(9) 0.2555(6) 0.9398(5) 0.0211(12) Uani 0.5 1 d D . P A 1
H18A H 0.441381 0.228709 1.003385 0.025 Uiso 0.5 1 calc R . P A 1
H18B H 0.248720 0.192920 0.941845 0.025 Uiso 0.5 1 calc R . P A 1
C192 C 0.2876(8) 0.3934(6) 0.9696(5) 0.0234(12) Uani 0.5 1 d D . P A 1
H19A H 0.175206 0.413185 0.914930 0.035 Uiso 0.5 1 calc GR . P A 1
H19B H 0.365502 0.456070 0.953601 0.035 Uiso 0.5 1 calc GR . P A 1
H19C H 0.291413 0.398296 1.059120 0.035 Uiso 0.5 1 calc GR . P A 1
C191 C 0.2540(11) 0.3117(13) 0.9718(8) 0.056(2) Uani 0.5 1 d D . P A 2
H19D H 0.204890 0.390147 0.925753 0.083 Uiso 0.5 1 calc GR . P A 2
H19E H 0.272696 0.324176 1.063210 0.083 Uiso 0.5 1 calc GR . P A 2
H19F H 0.178447 0.238767 0.941598 0.083 Uiso 0.5 1 calc GR . P A 2
C181 C 0.4188(11) 0.2838(9) 0.9483(8) 0.0416(19) Uani 0.5 1 d D . P A 2
H18C H 0.494931 0.358722 0.970236 0.050 Uiso 0.5 1 calc R . P A 2
H18D H 0.474110 0.206624 0.995615 0.050 Uiso 0.5 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 1.4836(19) . ?
P1 C1 1.812(3) . ?
P1 C7 1.818(3) . ?
P1 C14 1.826(2) . ?
O2 C17 1.199(4) . ?
O3 C17 1.322(4) . ?
O3 C182 1.509(6) . ?
O3 C181 1.487(8) . ?
C1 C2 1.397(4) . ?
C1 C6 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(4) . ?
C7 C12 1.410(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(5) . ?
C12 C13 1.505(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.534(4) . ?
C14 C16 1.537(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.515(4) . ?
C182 H18A 0.9700 . ?
C182 H18B 0.9700 . ?
C182 C192 1.518(8) . ?
C192 H19A 0.9600 . ?
C192 H19B 0.9600 . ?
C192 H19C 0.9600 . ?
C191 H19D 0.9600 . ?
C191 H19E 0.9600 . ?
C191 H19F 0.9600 . ?
C191 C181 1.495(8) . ?
C181 H18C 0.9700 . ?
C181 H18D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 111.99(12) . . ?
O1 P1 C7 115.90(12) . . ?
O1 P1 C14 111.16(11) . . ?
C1 P1 C7 103.06(12) . . ?
C1 P1 C14 106.49(11) . . ?
C7 P1 C14 107.55(13) . . ?
C17 O3 C182 110.5(3) . . ?
C17 O3 C181 120.1(4) . . ?
C2 C1 P1 117.8(2) . . ?
C6 C1 P1 122.0(2) . . ?
C6 C1 C2 120.2(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 P1 120.4(2) . . ?
C8 C7 C12 119.5(3) . . ?
C12 C7 P1 120.0(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.3(3) . . ?
C12 C11 H11 118.9 . . ?
C7 C12 C13 122.3(3) . . ?
C11 C12 C7 117.8(3) . . ?
C11 C12 C13 119.8(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
P1 C14 H14 109.4 . . ?
C15 C14 P1 108.96(17) . . ?
C15 C14 H14 109.4 . . ?
C15 C14 C16 111.9(2) . . ?
C16 C14 P1 107.71(18) . . ?
C16 C14 H14 109.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.1 . . ?
C14 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C14 112.3(2) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
O2 C17 O3 123.5(2) . . ?
O2 C17 C16 125.6(3) . . ?
O3 C17 C16 110.9(2) . . ?
O3 C182 H18A 110.3 . . ?
O3 C182 H18B 110.3 . . ?
O3 C182 C192 106.9(4) . . ?
H18A C182 H18B 108.6 . . ?
C192 C182 H18A 110.3 . . ?
C192 C182 H18B 110.3 . . ?
C182 C192 H19A 109.5 . . ?
C182 C192 H19B 109.5 . . ?
C182 C192 H19C 109.5 . . ?
H19A C192 H19B 109.5 . . ?
H19A C192 H19C 109.5 . . ?
H19B C192 H19C 109.5 . . ?
H19D C191 H19E 109.5 . . ?
H19D C191 H19F 109.5 . . ?
H19E C191 H19F 109.5 . . ?
C181 C191 H19D 109.5 . . ?
C181 C191 H19E 109.5 . . ?
C181 C191 H19F 109.5 . . ?
O3 C181 C191 99.2(6) . . ?
O3 C181 H18C 111.9 . . ?
O3 C181 H18D 111.9 . . ?
C191 C181 H18C 111.9 . . ?
C191 C181 H18D 111.9 . . ?
H18C C181 H18D 109.6 . . ?

_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 9.557
_oxdiff_exptl_absorpt_empirical_full_min 0.442
####################################################################### 
# 
# 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_816
_database_code_depnum_ccdc_archive 'CCDC 1920855'
loop_
_audit_author_name
_audit_author_address
'Zhu renyi'
;East China normal university
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
_audit_creation_date             2019-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H32 N O2 P S'
_chemical_formula_sum            'C24 H32 N O2 P S'
_chemical_formula_weight         429.53
_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 0.0181 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'
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'
S S 0.3331 0.5567 '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                   6.07450(10)
_cell_length_b                   19.8094(2)
_cell_length_c                   9.96830(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.0600(10)
_cell_angle_gamma                90
_cell_volume                     1187.66(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14448
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26423
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.404
_diffrn_reflns_theta_min         4.480
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  60.00   1.00    3.00    --    0.00  68.00 119.00   87
  2  ω     52.00 122.00   1.00    3.00    --   95.80 -68.00 -13.00   70
  3  ω    148.00 181.00   1.00    3.00    --   95.80  68.00 119.00   33
  4  ω     68.00 117.00   1.00    3.00    --   95.80  68.00 119.00   49
  5  ω    -65.00 -39.00   1.00    3.00    --    0.00 -57.00-120.00   26
  6  ω    -29.00   5.00   1.00    3.00    --    0.00 -38.00 120.00   34
  7  ω     -3.00  61.00   1.00    3.00    --    0.00  77.00 -60.00   64
  8  ω     -7.00  27.00   1.00    3.00    --    0.00 -68.00 -13.00   34
  9  ω    -29.00   6.00   1.00    3.00    --    0.00 -38.00   0.00   35
 10  ω    -31.00  51.00   1.00    3.00    --    0.00  82.00-180.00   82
 11  ω    -69.00 -44.00   1.00    3.00    --    0.00 -38.00 120.00   25
 12  ω    -18.00  89.00   1.00    3.00    --    0.00  38.00  30.00  107
 13  ω    -15.00  23.00   1.00    3.00    --    0.00 -57.00-120.00   38
 14  ω     55.00  81.00   1.00    3.00    --    0.00  82.00-180.00   26
 15  ω    -67.00  18.00   1.00    3.00    --    0.00 -38.00  60.00   85
 16  ω    -87.00 -44.00   1.00    3.00    --    0.00 -38.00   0.00   43
 17  ω     73.00 185.00   1.00    3.00    --   95.80  52.00  69.30  112
 18  ω     65.00  91.00   1.00    3.00    --   95.80  77.00  90.00   26
 19  ω    127.00 153.00   1.00    3.00    --   95.80  82.00  30.00   26
 20  ω    119.00 170.00   1.00    3.00    --   95.80  79.00  -5.32   51
 21  ω     64.00  90.00   1.00    3.00    --   95.80  79.00  -5.32   26
 22  ω     66.00  92.00   1.00    3.00    --   95.80  82.00  30.00   26
 23  ω    149.00 175.00   1.00    3.00    --   95.80  82.00  60.00   26
 24  ω      6.00 127.00   1.00    3.00    --   95.80 -82.00 -30.00  121
 25  ω     64.00  89.00   1.00    3.00    --   95.80  79.00 -44.37   25
 26  ω      7.00 127.00   1.00    3.00    --   95.80 -82.00-120.00  120
 27  ω     65.00  90.00   1.00    3.00    --   95.80  77.00  60.00   25
 28  ω     71.00 109.00   1.00    3.00    --   95.80  61.00 -60.00   38
 29  ω    115.00 140.00   1.00    3.00    --   95.80  61.00 -60.00   25
 30  ω     69.00 123.00   1.00    3.00    --   95.80  69.00-149.98   54
 31  ω     67.00 181.00   1.00    3.00    --   95.80  73.00 -95.36  114
 32  ω     24.00 125.00   1.00    3.00    --   95.80 -82.00 150.00  101
 33  ω     65.00  90.00   1.00    3.00    --   95.80  77.00-120.00   25
 34  ω     71.00 116.00   1.00    3.00    --   95.80  58.00  46.37   45
 35  ω     76.00 185.00   1.00    3.00    --   95.80  45.00  30.00  109
 36  ω     63.00  99.00   1.00    3.00    --   95.80  82.00 150.00   36
 37  ω    119.00 153.00   1.00    3.00    --   95.80  45.00-180.00   34
 38  ω    124.00 181.00   1.00    3.00    --   95.80  68.00-174.81   57
 39  ω     65.00  90.00   1.00    3.00    --   95.80  77.00 -90.00   25
 40  ω     68.00  94.00   1.00    3.00    --   95.80  68.00-174.81   26
 41  ω    139.00 170.00   1.00    3.00    --   95.80  62.00 -46.08   31
 42  ω     63.00  88.00   1.00    3.00    --   95.80  82.00  90.00   25
 43  ω     63.00  88.00   1.00    3.00    --   95.80  82.00-150.00   25
 44  ω    140.00 166.00   1.00    3.00    --   95.80  61.00 150.00   26
 45  ω     71.00 105.00   1.00    3.00    --   95.80  62.00 -46.08   34
 46  ω     71.00  97.00   1.00    3.00    --   95.80  61.00   0.00   26
 47  ω     65.00  90.00   1.00    3.00    --   95.80  77.00 -60.00   25
 48  ω    109.00 185.00   1.00    3.00    --   95.80  77.00 -60.00   76
 49  ω     63.00  89.00   1.00    3.00    --   95.80  82.00-180.00   26
 50  ω     71.00  96.00   1.00    3.00    --   95.80  61.00  90.00   25
 51  ω    140.00 181.00   1.00    3.00    --   95.80  45.00 120.00   41
 52  ω     65.00  90.00   1.00    3.00    --   95.80  77.00-150.00   25
 53  ω     65.00  95.00   1.00    3.00    --   95.80  77.00 -30.00   30
 54  ω     75.00 130.00   1.00    3.00    --   95.80  45.00 120.00   55
 55  ω     75.00 101.00   1.00    3.00    --   95.80  45.00-150.00   26
 56  ω    132.00 183.00   1.00    3.00    --   95.80  45.00-150.00   51
 57  ω     75.00 114.00   1.00    3.00    --   95.80  45.00  90.00   39
 58  ω    117.00 143.00   1.00    3.00    --   95.80  45.00  90.00   26
 59  ω     70.00 116.00   1.00    3.00    --   95.80  63.00-111.14   46
 60  ω    136.00 175.00   1.00    3.00    --   95.80  63.00-111.14   39
 61  ω     56.00 124.00   1.00    3.00    --   95.80 -82.00  60.00   68
 62  ω     65.00  90.00   1.00    3.00    --   95.80  77.00 120.00   25
 63  ω     71.00  97.00   1.00    3.00    --   95.80  61.00 150.00   26
 64  ω     78.00 104.00   1.00    3.00    --   95.80  45.00-180.00   26
 65  ω     71.00  96.00   1.00    3.00    --   95.80  61.00  30.00   25
 66  ω     63.00  88.00   1.00    3.00    --   95.80  82.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1348183000
_diffrn_orient_matrix_UB_12      -0.0361557000
_diffrn_orient_matrix_UB_13      0.1215217000
_diffrn_orient_matrix_UB_21      0.0978873000
_diffrn_orient_matrix_UB_22      -0.0480560000
_diffrn_orient_matrix_UB_23      -0.0977687000
_diffrn_orient_matrix_UB_31      0.1946298000
_diffrn_orient_matrix_UB_32      0.0492827000
_diffrn_orient_matrix_UB_33      -0.0061647000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4602
_reflns_number_total             4775
_reflns_odcompleteness_completeness 99.95
_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.
 
 _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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.246
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 2082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4775
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.2049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0753
_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:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C20(H20a,H20b,
 H20c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_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
S1 S 1.07986(11) 0.64746(3) 0.87540(6) 0.02350(15) Uani 1 1 d . . . . .
P1 P 0.28518(11) 0.44835(3) 0.62597(6) 0.01905(14) Uani 1 1 d . . . . .
O1 O 0.0598(3) 0.47274(9) 0.64394(17) 0.0232(4) Uani 1 1 d . . . . .
O2 O 1.3100(3) 0.66321(10) 0.85119(19) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.9552(4) 0.60170(11) 0.7504(2) 0.0254(5) Uani 1 1 d . . . . .
H1 H 1.009(5) 0.5700(18) 0.726(3) 0.031 Uiso 1 1 d R . . . .
C1 C 0.2835(4) 0.41393(12) 0.4579(3) 0.0218(5) Uani 1 1 d . . . . .
C2 C 0.0914(5) 0.42735(13) 0.3674(3) 0.0263(6) Uani 1 1 d . . . . .
H2 H -0.021538 0.453098 0.395786 0.032 Uiso 1 1 calc R . . . .
C3 C 0.0667(5) 0.40286(16) 0.2362(3) 0.0340(7) Uani 1 1 d . . . . .
H3 H -0.062861 0.411463 0.177158 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2352(6) 0.36570(16) 0.1936(3) 0.0382(7) Uani 1 1 d . . . . .
H4 H 0.220035 0.349577 0.105192 0.046 Uiso 1 1 calc R . . . .
C5 C 0.4275(5) 0.35214(15) 0.2818(3) 0.0341(7) Uani 1 1 d . . . . .
H5 H 0.539482 0.326805 0.251339 0.041 Uiso 1 1 calc R . . . .
C6 C 0.4574(5) 0.37550(13) 0.4151(3) 0.0259(6) Uani 1 1 d . . . . .
C7 C 0.6650(5) 0.35832(15) 0.5064(3) 0.0312(6) Uani 1 1 d . . . . .
H7A H 0.725637 0.398420 0.551333 0.047 Uiso 1 1 calc GR . . . .
H7B H 0.771061 0.339405 0.454083 0.047 Uiso 1 1 calc GR . . . .
H7C H 0.632149 0.326030 0.572603 0.047 Uiso 1 1 calc GR . . . .
C8 C 0.3825(5) 0.38517(13) 0.7497(3) 0.0254(6) Uani 1 1 d . . . . .
C9 C 0.2308(6) 0.33340(13) 0.7681(3) 0.0304(6) Uani 1 1 d . . . . .
H9 H 0.089851 0.333103 0.717710 0.036 Uiso 1 1 calc R . . . .
C10 C 0.2928(7) 0.28305(15) 0.8617(3) 0.0411(8) Uani 1 1 d . . . . .
H10 H 0.193701 0.248576 0.873991 0.049 Uiso 1 1 calc R . . . .
C11 C 0.5011(7) 0.28378(17) 0.9368(3) 0.0457(9) Uani 1 1 d . . . . .
H11 H 0.541634 0.249564 0.999255 0.055 Uiso 1 1 calc R . . . .
C12 C 0.6507(7) 0.33467(19) 0.9206(3) 0.0478(9) Uani 1 1 d . . . . .
H12 H 0.790372 0.334857 0.972501 0.057 Uiso 1 1 calc R . . . .
C13 C 0.5910(6) 0.38610(16) 0.8255(3) 0.0361(7) Uani 1 1 d . . . . .
H13 H 0.690945 0.420443 0.813665 0.043 Uiso 1 1 calc R . . . .
C14 C 0.4831(5) 0.51267(13) 0.6447(3) 0.0247(6) Uani 1 1 d . . . . .
C15 C 0.5962(4) 0.56276(13) 0.6594(3) 0.0221(5) Uani 1 1 d . . . . .
C16 C 0.7435(4) 0.62222(12) 0.6748(2) 0.0198(5) Uani 1 1 d . . . . .
H16 H 0.676864 0.655124 0.730573 0.024 Uiso 1 1 calc R . . . .
C17 C 0.7598(4) 0.65637(13) 0.5360(3) 0.0241(5) Uani 1 1 d . . . . .
C18 C 0.8505(5) 0.60742(14) 0.4392(3) 0.0322(7) Uani 1 1 d . . . . .
H18A H 0.995595 0.592345 0.478310 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.860395 0.629806 0.354793 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.752742 0.569303 0.423423 0.048 Uiso 1 1 calc GR . . . .
C19 C 0.5272(5) 0.68003(14) 0.4762(3) 0.0301(6) Uani 1 1 d . . . . .
H19A H 0.430385 0.641693 0.460224 0.045 Uiso 1 1 calc GR . . . .
H19B H 0.534323 0.703113 0.392279 0.045 Uiso 1 1 calc GR . . . .
H19C H 0.470616 0.710164 0.538687 0.045 Uiso 1 1 calc GR . . . .
C20 C 0.9143(5) 0.71755(14) 0.5612(3) 0.0304(6) Uani 1 1 d . . . . .
H20A H 0.856524 0.748147 0.622350 0.046 Uiso 1 1 calc GR . . . .
H20B H 0.923539 0.740081 0.476944 0.046 Uiso 1 1 calc GR . . . .
H20C H 1.059811 0.702768 0.600275 0.046 Uiso 1 1 calc GR . . . .
C21 C 1.1117(5) 0.58496(14) 1.0150(2) 0.0249(6) Uani 1 1 d . . . . .
C22 C 1.2439(5) 0.52417(14) 0.9774(3) 0.0301(6) Uani 1 1 d . . . . .
H22A H 1.154407 0.498167 0.908986 0.045 Uiso 1 1 calc GR . . . .
H22B H 1.285135 0.496669 1.056179 0.045 Uiso 1 1 calc GR . . . .
H22C H 1.375481 0.539370 0.943232 0.045 Uiso 1 1 calc GR . . . .
C23 C 0.8782(5) 0.56648(16) 1.0408(3) 0.0332(6) Uani 1 1 d . . . . .
H23A H 0.795739 0.606929 1.052133 0.050 Uiso 1 1 calc GR . . . .
H23B H 0.886736 0.539540 1.121421 0.050 Uiso 1 1 calc GR . . . .
H23C H 0.804824 0.541312 0.965166 0.050 Uiso 1 1 calc GR . . . .
C24 C 1.2388(5) 0.62196(17) 1.1370(3) 0.0357(7) Uani 1 1 d . . . . .
H24A H 1.384693 0.633571 1.117835 0.054 Uiso 1 1 calc GR . . . .
H24B H 1.251369 0.593159 1.215127 0.054 Uiso 1 1 calc GR . . . .
H24C H 1.160127 0.662336 1.154382 0.054 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.485(2) . ?
S1 N1 1.638(2) . ?
S1 C21 1.852(3) . ?
P1 O1 1.4861(19) . ?
P1 C1 1.808(3) . ?
P1 C8 1.798(3) . ?
P1 C14 1.744(3) . ?
N1 H1 0.76(3) . ?
N1 C16 1.454(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.416(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(4) . ?
C6 C7 1.487(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.408(4) . ?
C8 C13 1.381(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.404(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.204(4) . ?
C15 C16 1.474(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.556(3) . ?
C17 C18 1.525(4) . ?
C17 C19 1.528(4) . ?
C17 C20 1.532(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.523(4) . ?
C21 C23 1.521(4) . ?
C21 C24 1.533(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 109.76(12) . . ?
O2 S1 C21 105.14(12) . . ?
N1 S1 C21 100.94(12) . . ?
O1 P1 C1 110.40(12) . . ?
O1 P1 C8 111.32(12) . . ?
O1 P1 C14 112.50(12) . . ?
C8 P1 C1 109.39(11) . . ?
C14 P1 C1 106.79(12) . . ?
C14 P1 C8 106.24(13) . . ?
S1 N1 H1 122(3) . . ?
C16 N1 S1 121.36(18) . . ?
C16 N1 H1 117(2) . . ?
C2 C1 P1 115.0(2) . . ?
C2 C1 C6 120.0(2) . . ?
C6 C1 P1 125.1(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 122.9(2) . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 C7 119.5(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 116.0(2) . . ?
C13 C8 P1 123.6(2) . . ?
C13 C8 C9 120.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 119.3(3) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 P1 171.2(3) . . ?
C14 C15 C16 177.2(3) . . ?
N1 C16 C15 108.1(2) . . ?
N1 C16 H16 107.3 . . ?
N1 C16 C17 114.9(2) . . ?
C15 C16 H16 107.3 . . ?
C15 C16 C17 111.6(2) . . ?
C17 C16 H16 107.3 . . ?
C18 C17 C16 111.1(2) . . ?
C18 C17 C19 110.2(2) . . ?
C18 C17 C20 109.8(2) . . ?
C19 C17 C16 108.0(2) . . ?
C19 C17 C20 109.5(2) . . ?
C20 C17 C16 108.2(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 S1 110.28(18) . . ?
C22 C21 C24 110.4(2) . . ?
C23 C21 S1 106.65(19) . . ?
C23 C21 C22 112.8(2) . . ?
C23 C21 C24 111.0(2) . . ?
C24 C21 S1 105.3(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_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 3.618
_oxdiff_exptl_absorpt_empirical_full_min 0.488
####################################################################### 
# 
# 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_248
_database_code_depnum_ccdc_archive 'CCDC 1826888'
loop_
_audit_author_name
_audit_author_address
'Zhu renyi' 'East China normal university'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
_audit_creation_date             2018-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 Au Cl P, C H2 Cl2'
_chemical_formula_sum            'C16 H18 Au Cl3 P'
_chemical_formula_weight         544.59
_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'
Au Au -4.4197 7.2980 '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'
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      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                   8.6866(3)
_cell_length_b                   10.7017(4)
_cell_length_c                   11.1556(3)
_cell_angle_alpha                72.428(3)
_cell_angle_beta                 86.595(3)
_cell_angle_gamma                70.591(3)
_cell_volume                     931.50(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13937
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1140
_cell_measurement_theta_min      4.1550
_shelx_estimated_absorpt_T_max   0.342
_shelx_estimated_absorpt_T_min   0.065
_exptl_absorpt_coefficient_mu    19.528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.942
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17430
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.048
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         4.161
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -49.00   1.00    1.00    --    0.00 -38.00 150.00   31
  2  ω    -84.00 -59.00   1.00    1.00    --    0.00 -38.00 -60.00   25
  3  ω    -17.00  53.00   1.00    1.00    --    0.00  57.00-180.00   70
  4  ω    -24.00   2.00   1.00    1.00    --    0.00  19.00  60.00   26
  5  ω     13.00  43.00   1.00    1.00    --    0.00  82.00 -90.00   30
  6  ω    -32.00  -1.00   1.00    1.00    --    0.00 -38.00 150.00   31
  7  ω    -31.00  15.00   1.00    1.00    --    0.00  82.00  90.00   46
  8  ω    -87.00   3.00   1.00    1.00    --    0.00 -38.00-120.00   90
  9  ω     10.00  67.00   1.00    1.00    --    0.00  19.00  60.00   57
 10  ω     31.00  67.00   1.00    1.00    --    0.00  82.00  90.00   36
 11  ω    -54.00  15.00   1.00    1.00    --    0.00 -38.00 -60.00   69
 12  ω    -26.00   9.00   1.00    1.00    --    0.00  82.00 -90.00   35
 13  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 14  ω    160.00 185.00   1.00    2.00    --   95.80  82.00 150.00   25
 15  ω    113.00 175.00   1.00    2.00    --   95.80  71.00  80.32   62
 16  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 150.00   26
 17  ω    160.00 185.00   1.00    2.00    --   95.80  77.00   0.00   25
 18  ω     69.00 100.00   1.00    2.00    --   95.80  71.00  80.32   31
 19  ω     65.00  94.00   1.00    2.00    --   95.80  77.00-116.42   29
 20  ω     59.00 127.00   1.00    2.00    --   95.80 -82.00-180.00   68
 21  ω    113.00 185.00   1.00    2.00    --   95.80  82.00 -90.00   72
 22  ω     65.00  90.00   1.00    2.00    --   95.80  77.00   0.00   25
 23  ω     64.00  90.00   1.00    2.00    --   95.80  82.00-180.00   26
 24  ω     64.00  89.00   1.00    2.00    --   95.80  82.00 120.00   25
 25  ω    117.00 183.00   1.00    2.00    --   95.80  82.00 120.00   66
 26  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 27  ω    116.00 184.00   1.00    2.00    --   95.80  77.00  60.00   68
 28  ω     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 29  ω     64.00  96.00   1.00    2.00    --   95.80  82.00 -90.00   32
 30  ω     65.00 101.00   1.00    2.00    --   95.80  77.00  30.00   36
 31  ω     92.00 128.00   1.00    2.00    --   95.80 -82.00 -30.00   36
 32  ω     38.00 123.00   1.00    2.00    --   95.80 -82.00 -90.00   85
 33  ω     71.00 106.00   1.00    2.00    --   95.80  61.00 -81.88   35
 34  ω     43.00  76.00   1.00    2.00    --   95.80 -82.00 -30.00   33
 35  ω    148.00 174.00   1.00    2.00    --   95.80  77.00 150.00   26
 36  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 150.00   25
 37  ω    129.00 184.00   1.00    2.00    --   95.80  82.00 -30.00   55
 38  ω    129.00 179.00   1.00    2.00    --   95.80  70.00 -56.54   50
 39  ω     63.00  94.00   1.00    2.00    --   95.80  82.00-150.00   31
 40  ω     38.00 127.00   1.00    2.00    --   95.80 -82.00 120.00   89
 41  ω     63.00  97.00   1.00    2.00    --   95.80  82.00   0.00   34
 42  ω     63.00  98.00   1.00    2.00    --   95.80  82.00  90.00   35
 43  ω     75.00 150.00   1.00    2.00    --   95.80  45.00-180.00   75
 44  ω     76.00 108.00   1.00    2.00    --   95.80  45.00-150.00   32
 45  ω    127.00 184.00   1.00    2.00    --   95.80  45.00-150.00   57
 46  ω     75.00 184.00   1.00    2.00    --   95.80  45.00-120.00  109
 47  ω     75.00 106.00   1.00    2.00    --   95.80  45.00 -30.00   31
 48  ω    136.00 162.00   1.00    2.00    --   95.80  45.00 -30.00   26
 49  ω     80.00 113.00   1.00    2.00    --   95.80  45.00  30.00   33
 50  ω    130.00 184.00   1.00    2.00    --   95.80  45.00  30.00   54
 51  ω     65.00  91.00   1.00    2.00    --   95.80  82.00  30.00   26
 52  ω     72.00  97.00   1.00    2.00    --   95.80  61.00   0.00   25
 53  ω     75.00 104.00   1.00    2.00    --   95.80  45.00   0.00   29
 54  ω    139.00 184.00   1.00    2.00    --   95.80  45.00   0.00   45
 55  ω     76.00 106.00   1.00    2.00    --   95.80  45.00  60.00   30
 56  ω    123.00 149.00   1.00    2.00    --   95.80  45.00  60.00   26
 57  ω     63.00  94.00   1.00    2.00    --   95.80  82.00 -60.00   31
 58  ω     63.00  89.00   1.00    2.00    --   95.80  82.00 -30.00   26
 59  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 60  ω     76.00 110.00   1.00    2.00    --   95.80  45.00 150.00   34
 61  ω     75.00 100.00   1.00    2.00    --   95.80  45.00  90.00   25
 62  ω     65.00  91.00   1.00    2.00    --   95.80  77.00  90.00   26
 63  ω    151.00 176.00   1.00    2.00    --   95.80  77.00-150.00   25
 64  ω     68.00  94.00   1.00    2.00    --   95.80  70.00 -56.54   26
 65  ω    129.00 154.00   1.00    2.00    --   95.80  45.00 150.00   25
 66  ω     74.00 182.00   1.00    2.00    --   95.80  48.00 155.40  108
 67  ω    127.00 176.00   1.00    2.00    --   95.80  34.00 -75.96   49
 68  ω     61.00 103.00   1.00    2.00    --   95.80 -82.00  60.00   42
 69  ω     76.00 102.00   1.00    2.00    --   95.80  34.00 -75.96   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118526000
_diffrn_orient_matrix_UB_12      0.0564606000
_diffrn_orient_matrix_UB_13      -0.1447779000
_diffrn_orient_matrix_UB_21      0.0694489000
_diffrn_orient_matrix_UB_22      -0.1495539000
_diffrn_orient_matrix_UB_23      -0.0081460000
_diffrn_orient_matrix_UB_31      -0.1745487000
_diffrn_orient_matrix_UB_32      -0.0063439000
_diffrn_orient_matrix_UB_33      -0.0005292000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3039
_reflns_number_total             3313
_reflns_odcompleteness_completeness 99.46
_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.
 
 _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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         2.271
_refine_diff_density_min         -2.080
_refine_diff_density_rms         0.209
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.081
_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)+(0.1100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1531
_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:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C11(H11), C2(H2), C10(H10), C9(H9), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
Au1 Au 0.74022(4) 0.36666(3) 0.76974(2) 0.0509(2) Uani 1 1 d . . . . .
P1 P 0.6801(3) 0.5789(2) 0.78974(18) 0.0439(5) Uani 1 1 d . . . . .
Cl1 Cl 0.8014(4) 0.1480(3) 0.7542(3) 0.0804(7) Uani 1 1 d . . . . .
Cl2 Cl 0.3076(7) 0.3435(5) 0.7605(4) 0.1292(13) Uani 1 1 d . . . . .
Cl3 Cl 0.2709(9) 0.1026(5) 0.9548(6) 0.169(2) Uani 1 1 d . . . . .
C1 C 0.7491(10) 0.6982(8) 0.6616(6) 0.0471(17) Uani 1 1 d . . . . .
C7 C 0.4630(10) 0.6675(7) 0.7952(7) 0.0482(16) Uani 1 1 d . . . . .
C8 C 0.3548(11) 0.6857(8) 0.6983(8) 0.057(2) Uani 1 1 d . . . . .
C6 C 0.8510(13) 0.6483(10) 0.5734(8) 0.068(2) Uani 1 1 d . . . . .
H6 H 0.885854 0.553943 0.581278 0.081 Uiso 1 1 calc R . . . .
C13 C 0.7761(10) 0.5736(8) 0.9314(7) 0.0494(17) Uani 1 1 d . . . . .
H13A H 0.754351 0.667861 0.933629 0.059 Uiso 1 1 calc R . . . .
H13B H 0.727997 0.526212 1.004014 0.059 Uiso 1 1 calc R . . . .
C14 C 0.9590(9) 0.5006(8) 0.9402(6) 0.0496(17) Uani 1 1 d . . . . .
H14A H 1.006924 0.546667 0.866666 0.060 Uiso 1 1 calc R . . . .
H14B H 0.980829 0.405662 0.940081 0.060 Uiso 1 1 calc R . . . .
C12 C 0.3996(11) 0.7184(9) 0.8959(8) 0.058(2) Uani 1 1 d . . . . .
H12 H 0.470062 0.705348 0.961525 0.070 Uiso 1 1 calc R . . . .
C11 C 0.2358(13) 0.7871(9) 0.9002(9) 0.068(2) Uani 1 1 d . . . . .
H11 H 0.196880 0.823373 0.966329 0.082 Uiso 1 1 calc R . . . .
C2 C 0.6999(15) 0.8373(9) 0.6513(10) 0.079(3) Uani 1 1 d . . . . .
H2 H 0.632810 0.870595 0.710731 0.095 Uiso 1 1 calc R . . . .
C10 C 0.1309(12) 0.8020(9) 0.8072(10) 0.071(3) Uani 1 1 d . . . . .
H10 H 0.019254 0.845220 0.810891 0.085 Uiso 1 1 calc R . . . .
C9 C 0.1906(13) 0.7529(10) 0.7086(10) 0.073(3) Uani 1 1 d . . . . .
H9 H 0.117437 0.765206 0.645085 0.088 Uiso 1 1 calc R . . . .
C15 C 0.4144(15) 0.6401(13) 0.5854(10) 0.087(3) Uani 1 1 d . . . . .
H15A H 0.431837 0.715887 0.520294 0.130 Uiso 1 1 calc GR . . . .
H15B H 0.334455 0.610913 0.555810 0.130 Uiso 1 1 calc GR . . . .
H15C H 0.515246 0.563999 0.607322 0.130 Uiso 1 1 calc GR . . . .
C5 C 0.9009(16) 0.7379(12) 0.4739(9) 0.081(3) Uani 1 1 d . . . . .
H5 H 0.968056 0.704521 0.414555 0.097 Uiso 1 1 calc R . . . .
C4 C 0.8502(15) 0.8765(12) 0.4640(9) 0.078(3) Uani 1 1 d . . . . .
H4 H 0.883274 0.936978 0.397115 0.094 Uiso 1 1 calc R . . . .
C3 C 0.7502(15) 0.9284(10) 0.5521(11) 0.083(3) Uani 1 1 d . . . . .
H3 H 0.717380 1.022515 0.544829 0.100 Uiso 1 1 calc R . . . .
C16 C 0.367(3) 0.158(2) 0.8105(19) 0.160(9) Uani 1 1 d . . . . .
H16A H 0.484358 0.118271 0.823399 0.192 Uiso 1 1 calc R . . . .
H16B H 0.333337 0.127207 0.746272 0.192 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
Au1 P1 2.233(2) . ?
Au1 Cl1 2.279(3) . ?
P1 C1 1.827(8) . ?
P1 C7 1.814(8) . ?
P1 C13 1.808(7) . ?
Cl2 C16 1.79(2) . ?
Cl3 C16 1.80(2) . ?
C1 C6 1.393(12) . ?
C1 C2 1.375(12) . ?
C7 C8 1.402(10) . ?
C7 C12 1.399(11) . ?
C8 C9 1.383(14) . ?
C8 C15 1.489(14) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.514(11) . ?
C14 C14 1.544(14) 2_767 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C11 1.373(13) . ?
C11 H11 0.9300 . ?
C11 C10 1.360(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(14) . ?
C10 H10 0.9300 . ?
C10 C9 1.362(15) . ?
C9 H9 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.370(17) . ?
C4 H4 0.9300 . ?
C4 C3 1.392(17) . ?
C3 H3 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Au1 Cl1 178.69(7) . . ?
C1 P1 Au1 114.0(3) . . ?
C7 P1 Au1 113.9(3) . . ?
C7 P1 C1 104.7(3) . . ?
C13 P1 Au1 111.4(3) . . ?
C13 P1 C1 105.2(4) . . ?
C13 P1 C7 106.9(4) . . ?
C6 C1 P1 119.8(6) . . ?
C2 C1 P1 120.4(7) . . ?
C2 C1 C6 119.8(8) . . ?
C8 C7 P1 120.4(6) . . ?
C12 C7 P1 121.2(6) . . ?
C12 C7 C8 118.5(8) . . ?
C7 C8 C15 121.4(8) . . ?
C9 C8 C7 117.5(8) . . ?
C9 C8 C15 121.0(8) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.5(9) . . ?
C5 C6 H6 119.7 . . ?
P1 C13 H13A 109.0 . . ?
P1 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 P1 112.7(5) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C13 C14 C14 112.5(8) . 2_767 ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C14 C14 H14A 109.1 2_767 . ?
C14 C14 H14B 109.1 2_767 . ?
H14A C14 H14B 107.8 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.6(9) . . ?
C11 C12 H12 119.2 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.6(9) . . ?
C10 C11 H11 120.2 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(10) . . ?
C3 C2 H2 119.9 . . ?
C11 C10 H10 120.3 . . ?
C11 C10 C9 119.5(9) . . ?
C9 C10 H10 120.3 . . ?
C8 C9 H9 118.4 . . ?
C10 C9 C8 123.2(9) . . ?
C10 C9 H9 118.4 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.2(10) . . ?
C4 C5 H5 120.4 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.3(8) . . ?
C3 C4 H4 119.4 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(9) . . ?
C4 C3 H3 120.5 . . ?
Cl2 C16 Cl3 109.3(9) . . ?
Cl2 C16 H16A 109.8 . . ?
Cl2 C16 H16B 109.8 . . ?
Cl3 C16 H16A 109.8 . . ?
Cl3 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?

_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 9.756
_oxdiff_exptl_absorpt_empirical_full_min 0.224
####################################################################### 
# 
# 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_cd15350
_audit_block_doi                 10.5517/cc1kp17j
_database_code_depnum_ccdc_archive 'CCDC 1450187'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H33 Cl N3 O3 P'
_chemical_formula_weight         622.07

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.421(2)
_cell_length_b                   7.7894(13)
_cell_length_c                   16.028(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.539(4)
_cell_angle_gamma                90
_cell_volume                     1637.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1012
_cell_measurement_theta_min      4.965
_cell_measurement_theta_max      38.207

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9105
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.552
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             5518
_reflns_number_gt                3679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    0.879

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1001 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.00(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5518
_refine_ls_number_parameters     410
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001

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 1.0274(2) 0.9256(11) 1.1786(3) 0.237(4) Uani 1 1 d . . . . .
P1 P 0.28441(14) 0.9359(3) 0.45321(13) 0.0459(6) Uani 1 1 d . . . . .
N1 N 0.5299(5) 0.8551(11) 0.9600(4) 0.066(2) Uani 1 1 d . . . . .
N2 N 0.4316(5) 0.8861(13) 0.9171(5) 0.082(3) Uani 1 1 d . . . . .
N3 N 0.4093(5) 0.8904(12) 0.8298(4) 0.076(3) Uani 1 1 d . . . . .
O1 O 0.2408(4) 1.1083(8) 0.4456(4) 0.0607(16) Uani 1 1 d . . . . .
O2 O 0.6655(4) 0.8180(9) 0.7814(4) 0.0662(18) Uani 1 1 d . . . . .
O3 O 0.5550(4) 0.7889(9) 0.2689(4) 0.0711(19) Uani 1 1 d . . . . .
C1 C 0.5700(6) 0.8357(15) 0.8976(5) 0.072(3) Uani 1 1 d . . . . .
H1 H 0.6371 0.8093 0.9092 0.087 Uiso 1 1 calc R U . . .
C2 C 0.4927(5) 0.8625(11) 0.8159(5) 0.0463(19) Uani 1 1 d . . . . .
C3 C 0.4902(5) 0.8606(12) 0.7224(5) 0.050(2) Uani 1 1 d . . . . .
C4 C 0.3970(5) 0.8855(9) 0.6474(5) 0.0421(18) Uani 1 1 d . . . . .
H4 H 0.3381 0.9025 0.6566 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3923(5) 0.8851(11) 0.5590(5) 0.050(2) Uani 1 1 d . . . . .
C6 C 0.4794(6) 0.8566(11) 0.5440(5) 0.048(2) Uani 1 1 d . . . . .
C7 C 0.5714(6) 0.8329(11) 0.6176(5) 0.047(2) Uani 1 1 d . . . . .
H7 H 0.6301 0.8148 0.6082 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5768(5) 0.8359(11) 0.7061(5) 0.047(2) Uani 1 1 d . . . . .
C9 C 0.4583(6) 0.8571(10) 0.4448(5) 0.0454(19) Uani 1 1 d . . . . .
C10 C 0.5275(6) 0.8243(11) 0.4076(5) 0.052(2) Uani 1 1 d . . . . .
H10 H 0.5953 0.8014 0.4459 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4962(6) 0.8254(11) 0.3135(5) 0.054(2) Uani 1 1 d . . . . .
C12 C 0.3925(6) 0.8607(12) 0.2552(5) 0.056(2) Uani 1 1 d . . . . .
C13 C 0.3247(6) 0.8881(12) 0.2925(5) 0.054(2) Uani 1 1 d . . . . .
H13 H 0.2562 0.9056 0.2545 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3570(6) 0.8900(11) 0.3872(5) 0.054(2) Uani 1 1 d . . . . .
C15 C 0.3595(6) 0.8610(14) 0.1565(6) 0.067(3) Uani 1 1 d . . . . .
C16 C 0.3344(8) 0.8682(18) 0.0785(7) 0.103(4) Uani 1 1 d . . . . .
H16 H 0.3142 0.8741 0.0153 0.124 Uiso 1 1 calc R U . . .
C17 C 0.1882(6) 0.7712(11) 0.4270(5) 0.046(2) Uani 1 1 d . . . . .
C18 C 0.2082(7) 0.6027(13) 0.4192(6) 0.064(2) Uani 1 1 d . . . . .
H18 H 0.2743 0.5707 0.4297 0.077 Uiso 1 1 calc R U . . .
C19 C 0.1357(9) 0.4807(13) 0.3966(7) 0.076(3) Uani 1 1 d . . . . .
H19 H 0.1518 0.3669 0.3910 0.091 Uiso 1 1 calc R U . . .
C20 C 0.0384(9) 0.5242(17) 0.3820(7) 0.081(3) Uani 1 1 d . . . . .
C21 C 0.0161(8) 0.6901(19) 0.3924(8) 0.090(4) Uani 1 1 d . . . . .
H21 H -0.0491 0.7203 0.3855 0.108 Uiso 1 1 calc R U . . .
C22 C 0.0902(6) 0.8119(14) 0.4132(6) 0.067(3) Uani 1 1 d . . . . .
H22 H 0.0739 0.9259 0.4181 0.081 Uiso 1 1 calc R U . . .
C23 C -0.0436(9) 0.3885(18) 0.3572(9) 0.125(5) Uani 1 1 d . . . . .
H23A H -0.0263 0.2936 0.3281 0.187 Uiso 1 1 calc R U . . .
H23B H -0.1076 0.4363 0.3158 0.187 Uiso 1 1 calc R U . . .
H23C H -0.0490 0.3493 0.4117 0.187 Uiso 1 1 calc R U . . .
C24 C 0.5801(7) 0.8450(18) 1.0614(5) 0.087(4) Uani 1 1 d . . . . .
H24A H 0.5653 0.7347 1.0812 0.105 Uiso 1 1 calc R U . . .
H24B H 0.5530 0.9340 1.0874 0.105 Uiso 1 1 calc R U . . .
C25 C 0.6948(7) 0.8667(19) 1.0962(6) 0.072(3) Uani 1 1 d . . . . .
C26 C 0.7339(11) 1.025(2) 1.1001(9) 0.109(4) Uani 1 1 d . . . . .
H26 H 0.6916 1.1210 1.0843 0.130 Uiso 1 1 calc R U . . .
C27 C 0.8364(14) 1.043(2) 1.1275(10) 0.128(5) Uani 1 1 d . . . . .
H27 H 0.8638 1.1521 1.1316 0.153 Uiso 1 1 calc R U . . .
C28 C 0.8998(10) 0.904(3) 1.1491(9) 0.126(6) Uani 1 1 d . . . . .
C29 C 0.8581(9) 0.749(2) 1.1449(9) 0.112(5) Uani 1 1 d . . . . .
H29 H 0.8992 0.6513 1.1598 0.134 Uiso 1 1 calc R U . . .
C30 C 0.7561(9) 0.7332(17) 1.1188(7) 0.086(3) Uani 1 1 d . . . . .
H30 H 0.7286 0.6245 1.1169 0.104 Uiso 1 1 calc R U . . .
C31 C 0.6639(6) 0.8046(11) 0.3163(6) 0.057(2) Uani 1 1 d . . . . .
H31A H 0.6958 0.7468 0.2814 0.069 Uiso 1 1 calc R U . . .
H31B H 0.6868 0.7491 0.3757 0.069 Uiso 1 1 calc R U . . .
C32 C 0.6952(8) 0.9837(13) 0.3289(8) 0.087(3) Uani 1 1 d . . . . .
H32A H 0.6742 1.0353 0.3734 0.105 Uiso 1 1 calc R U . . .
H32B H 0.6606 1.0442 0.2713 0.105 Uiso 1 1 calc R U . . .
C33 C 0.8071(8) 1.0056(19) 0.3607(9) 0.121(5) Uani 1 1 d . . . . .
H33A H 0.8405 0.9802 0.4250 0.181 Uiso 1 1 calc R U . . .
H33B H 0.8217 1.1218 0.3502 0.181 Uiso 1 1 calc R U . . .
H33C H 0.8314 0.9288 0.3273 0.181 Uiso 1 1 calc R U . . .
C34 C 0.7598(6) 0.8498(17) 0.7754(6) 0.087(3) Uani 1 1 d . . . . .
H34A H 0.7570 0.9587 0.7451 0.104 Uiso 1 1 calc R U . . .
H34B H 0.7735 0.7598 0.7402 0.104 Uiso 1 1 calc R U . . .
C35 C 0.8410(7) 0.854(2) 0.8701(8) 0.127(5) Uani 1 1 d D . . . .
H35A H 0.8510 0.7388 0.8936 0.152 Uiso 0.7 1 d R U P A 1
H35B H 0.8188 0.9245 0.9074 0.152 Uiso 0.7 1 d R U P A 1
H35C H 0.9063 0.8348 0.8690 0.152 Uiso 0.3 1 d R U P B 2
H35D H 0.8276 0.7648 0.9050 0.152 Uiso 0.3 1 d R U P B 2
C36 C 0.9400(12) 0.920(4) 0.8758(15) 0.184(11) Uani 0.7 1 d D U P C 1
H36A H 0.9597 0.8575 0.8341 0.276 Uiso 0.7 1 calc R U P C 1
H36B H 0.9911 0.9065 0.9372 0.276 Uiso 0.7 1 calc R U P C 1
H36C H 0.9332 1.0398 0.8597 0.276 Uiso 0.7 1 calc R U P C 1
C36' C 0.844(4) 1.027(5) 0.914(4) 0.183(12) Uani 0.3 1 d D U P C 2
H36D H 0.8985 1.0943 0.9115 0.275 Uiso 0.3 1 calc R U P C 2
H36E H 0.8556 1.0105 0.9772 0.275 Uiso 0.3 1 calc R U P C 2
H36F H 0.7805 1.0850 0.8822 0.275 Uiso 0.3 1 calc R U P C 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
Cl1 C28 1.707(14) . ?
P1 O1 1.467(6) . ?
P1 C17 1.806(9) . ?
P1 C5 1.806(8) . ?
P1 C14 1.806(7) . ?
N1 N2 1.316(9) . ?
N1 C1 1.355(9) . ?
N1 C24 1.481(10) . ?
N2 N3 1.300(9) . ?
N3 C2 1.328(8) . ?
O2 C8 1.353(8) . ?
O2 C34 1.424(10) . ?
O3 C11 1.347(8) . ?
O3 C31 1.438(9) . ?
C1 C2 1.337(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.486(10) . ?
C3 C8 1.390(9) . ?
C3 C4 1.395(10) . ?
C4 C5 1.390(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(9) . ?
C6 C7 1.373(10) . ?
C6 C9 1.489(10) . ?
C7 C8 1.389(10) . ?
C7 H7 0.9300 . ?
C9 C10 1.384(9) . ?
C9 C14 1.390(10) . ?
C10 C11 1.383(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.422(11) . ?
C12 C13 1.358(10) . ?
C12 C15 1.451(11) . ?
C13 C14 1.391(10) . ?
C13 H13 0.9300 . ?
C15 C16 1.150(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(12) . ?
C17 C22 1.374(11) . ?
C18 C19 1.347(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(13) . ?
C19 H19 0.9300 . ?
C20 C21 1.359(15) . ?
C20 C23 1.511(15) . ?
C21 C22 1.362(14) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.520(12) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C30 1.315(14) . ?
C25 C26 1.347(16) . ?
C26 C27 1.364(17) . ?
C26 H26 0.9300 . ?
C27 C28 1.36(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.34(2) . ?
C29 C30 1.358(15) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.454(13) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.486(13) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.483(13) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.485(16) . ?
C35 C36' 1.51(3) . ?
C35 H35A 0.9598 . ?
C35 H35B 0.9602 . ?
C35 H35C 0.9601 . ?
C35 H35D 0.9602 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36' H36D 0.9600 . ?
C36' H36E 0.9600 . ?
C36' H36F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C17 111.7(4) . . ?
O1 P1 C5 116.8(4) . . ?
C17 P1 C5 110.0(4) . . ?
O1 P1 C14 117.8(4) . . ?
C17 P1 C14 107.4(4) . . ?
C5 P1 C14 91.4(3) . . ?
N2 N1 C1 109.4(6) . . ?
N2 N1 C24 120.9(6) . . ?
C1 N1 C24 129.8(7) . . ?
N3 N2 N1 107.4(6) . . ?
N2 N3 C2 109.8(6) . . ?
C8 O2 C34 119.8(6) . . ?
C11 O3 C31 119.5(6) . . ?
C2 C1 N1 105.5(7) . . ?
C2 C1 H1 127.2 . . ?
N1 C1 H1 127.2 . . ?
N3 C2 C1 107.9(6) . . ?
N3 C2 C3 121.8(7) . . ?
C1 C2 C3 130.4(7) . . ?
C8 C3 C4 118.5(6) . . ?
C8 C3 C2 122.9(7) . . ?
C4 C3 C2 118.6(6) . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 P1 128.0(5) . . ?
C6 C5 P1 111.1(5) . . ?
C7 C6 C5 119.5(6) . . ?
C7 C6 C9 127.9(6) . . ?
C5 C6 C9 112.6(7) . . ?
C6 C7 C8 120.0(6) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O2 C8 C7 122.7(6) . . ?
O2 C8 C3 115.9(6) . . ?
C7 C8 C3 121.4(7) . . ?
C10 C9 C14 119.7(7) . . ?
C10 C9 C6 126.6(7) . . ?
C14 C9 C6 113.7(6) . . ?
C9 C10 C11 120.1(7) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
O3 C11 C10 125.8(7) . . ?
O3 C11 C12 114.5(7) . . ?
C10 C11 C12 119.7(7) . . ?
C13 C12 C11 119.6(7) . . ?
C13 C12 C15 120.7(7) . . ?
C11 C12 C15 119.7(7) . . ?
C12 C13 C14 120.4(7) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.4(6) . . ?
C13 C14 P1 128.9(6) . . ?
C9 C14 P1 110.6(5) . . ?
C16 C15 C12 177.2(13) . . ?
C15 C16 H16 180.0 . . ?
C18 C17 C22 116.8(9) . . ?
C18 C17 P1 122.3(7) . . ?
C22 C17 P1 120.9(7) . . ?
C19 C18 C17 122.3(9) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 119.9(10) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.6(10) . . ?
C21 C20 C23 119.9(12) . . ?
C19 C20 C23 120.5(12) . . ?
C20 C21 C22 119.4(10) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C17 121.9(10) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 C25 111.0(7) . . ?
N1 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
N1 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C30 C25 C26 119.4(11) . . ?
C30 C25 C24 121.2(13) . . ?
C26 C25 C24 119.3(12) . . ?
C25 C26 C27 118.9(15) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C28 C27 C26 121.7(17) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C29 C28 C27 117.6(14) . . ?
C29 C28 Cl1 120.7(16) . . ?
C27 C28 Cl1 121.7(19) . . ?
C28 C29 C30 120.1(14) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 122.2(13) . . ?
C25 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
O3 C31 C32 111.3(8) . . ?
O3 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
O3 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 112.8(10) . . ?
C31 C32 H32A 109.0 . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
C33 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O2 C34 C35 107.8(8) . . ?
O2 C34 H34A 110.2 . . ?
C35 C34 H34A 110.2 . . ?
O2 C34 H34B 110.2 . . ?
C35 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
C34 C35 C36 113.7(12) . . ?
C34 C35 C36' 111(3) . . ?
C34 C35 H35A 107.9 . . ?
C36 C35 H35A 108.5 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 109.0 . . ?
C34 C35 H35C 110.0 . . ?
C36' C35 H35C 107.9 . . ?
C34 C35 H35D 108.4 . . ?
C36' C35 H35D 110.2 . . ?
H35C C35 H35D 109.6 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C36' H36D 109.5 . . ?
C35 C36' H36E 109.5 . . ?
H36D C36' H36E 109.5 . . ?
C35 C36' H36F 109.5 . . ?
H36D C36' H36F 109.5 . . ?
H36E C36' H36F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -1.3(12) . . . . ?
C24 N1 N2 N3 179.0(9) . . . . ?
N1 N2 N3 C2 -0.1(12) . . . . ?
N2 N1 C1 C2 2.2(12) . . . . ?
C24 N1 C1 C2 -178.2(10) . . . . ?
N2 N3 C2 C1 1.5(12) . . . . ?
N2 N3 C2 C3 -179.8(9) . . . . ?
N1 C1 C2 N3 -2.2(12) . . . . ?
N1 C1 C2 C3 179.3(9) . . . . ?
N3 C2 C3 C8 178.4(9) . . . . ?
C1 C2 C3 C8 -3.2(16) . . . . ?
N3 C2 C3 C4 -1.2(13) . . . . ?
C1 C2 C3 C4 177.1(10) . . . . ?
C8 C3 C4 C5 0.1(12) . . . . ?
C2 C3 C4 C5 179.7(8) . . . . ?
C3 C4 C5 C6 1.2(12) . . . . ?
C3 C4 C5 P1 -173.1(6) . . . . ?
O1 P1 C5 C4 59.4(9) . . . . ?
C17 P1 C5 C4 -69.2(8) . . . . ?
C14 P1 C5 C4 -178.3(8) . . . . ?
O1 P1 C5 C6 -115.3(6) . . . . ?
C17 P1 C5 C6 116.1(6) . . . . ?
C14 P1 C5 C6 6.9(7) . . . . ?
C4 C5 C6 C7 -1.6(12) . . . . ?
P1 C5 C6 C7 173.6(7) . . . . ?
C4 C5 C6 C9 178.7(8) . . . . ?
P1 C5 C6 C9 -6.1(9) . . . . ?
C5 C6 C7 C8 0.6(12) . . . . ?
C9 C6 C7 C8 -179.7(8) . . . . ?
C34 O2 C8 C7 20.1(13) . . . . ?
C34 O2 C8 C3 -158.9(9) . . . . ?
C6 C7 C8 O2 -178.1(8) . . . . ?
C6 C7 C8 C3 0.8(13) . . . . ?
C4 C3 C8 O2 177.9(7) . . . . ?
C2 C3 C8 O2 -1.8(12) . . . . ?
C4 C3 C8 C7 -1.1(13) . . . . ?
C2 C3 C8 C7 179.3(8) . . . . ?
C7 C6 C9 C10 3.7(14) . . . . ?
C5 C6 C9 C10 -176.6(8) . . . . ?
C7 C6 C9 C14 -178.1(8) . . . . ?
C5 C6 C9 C14 1.6(10) . . . . ?
C14 C9 C10 C11 0.4(12) . . . . ?
C6 C9 C10 C11 178.5(8) . . . . ?
C31 O3 C11 C10 -22.3(13) . . . . ?
C31 O3 C11 C12 160.3(8) . . . . ?
C9 C10 C11 O3 -177.2(8) . . . . ?
C9 C10 C11 C12 0.1(13) . . . . ?
O3 C11 C12 C13 175.7(8) . . . . ?
C10 C11 C12 C13 -1.9(14) . . . . ?
O3 C11 C12 C15 -2.1(12) . . . . ?
C10 C11 C12 C15 -179.6(8) . . . . ?
C11 C12 C13 C14 3.1(14) . . . . ?
C15 C12 C13 C14 -179.1(9) . . . . ?
C12 C13 C14 C9 -2.6(13) . . . . ?
C12 C13 C14 P1 175.9(7) . . . . ?
C10 C9 C14 C13 0.8(12) . . . . ?
C6 C9 C14 C13 -177.5(8) . . . . ?
C10 C9 C14 P1 -178.0(7) . . . . ?
C6 C9 C14 P1 3.7(9) . . . . ?
O1 P1 C14 C13 -63.1(9) . . . . ?
C17 P1 C14 C13 63.9(9) . . . . ?
C5 P1 C14 C13 175.4(9) . . . . ?
O1 P1 C14 C9 115.5(6) . . . . ?
C17 P1 C14 C9 -117.4(6) . . . . ?
C5 P1 C14 C9 -6.0(7) . . . . ?
O1 P1 C17 C18 172.3(6) . . . . ?
C5 P1 C17 C18 -56.4(7) . . . . ?
C14 P1 C17 C18 41.7(8) . . . . ?
O1 P1 C17 C22 -7.1(7) . . . . ?
C5 P1 C17 C22 124.3(7) . . . . ?
C14 P1 C17 C22 -137.6(7) . . . . ?
C22 C17 C18 C19 1.7(13) . . . . ?
P1 C17 C18 C19 -177.7(7) . . . . ?
C17 C18 C19 C20 -0.9(15) . . . . ?
C18 C19 C20 C21 -1.6(16) . . . . ?
C18 C19 C20 C23 -179.7(10) . . . . ?
C19 C20 C21 C22 3.1(17) . . . . ?
C23 C20 C21 C22 -178.8(10) . . . . ?
C20 C21 C22 C17 -2.3(16) . . . . ?
C18 C17 C22 C21 -0.1(13) . . . . ?
P1 C17 C22 C21 179.3(8) . . . . ?
N2 N1 C24 C25 -161.4(11) . . . . ?
C1 N1 C24 C25 19.0(17) . . . . ?
N1 C24 C25 C30 -99.0(12) . . . . ?
N1 C24 C25 C26 78.0(13) . . . . ?
C30 C25 C26 C27 0.0(17) . . . . ?
C24 C25 C26 C27 -177.1(10) . . . . ?
C25 C26 C27 C28 1(2) . . . . ?
C26 C27 C28 C29 -2(2) . . . . ?
C26 C27 C28 Cl1 177.1(11) . . . . ?
C27 C28 C29 C30 1(2) . . . . ?
Cl1 C28 C29 C30 -178.1(10) . . . . ?
C26 C25 C30 C29 -1.0(17) . . . . ?
C24 C25 C30 C29 176.0(10) . . . . ?
C28 C29 C30 C25 1(2) . . . . ?
C11 O3 C31 C32 -73.7(10) . . . . ?
O3 C31 C32 C33 -168.7(8) . . . . ?
C8 O2 C34 C35 169.2(10) . . . . ?
O2 C34 C35 C36 -168.3(17) . . . . ?
O2 C34 C35 C36' -81(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2 0.93 2.25 2.741(9) 112.3 .
C1 H1 O2 0.93 2.25 2.741(9) 112.3 .
C1 H1 O2 0.93 2.25 2.741(9) 112.3 .
C1 H1 O2 0.93 2.25 2.741(9) 112.3 .
C1 H1 O2 0.93 2.25 2.741(9) 112.3 .

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_z_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1548228'
_audit_update_record             
;
2017-05-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 O P'
_chemical_formula_weight         240.22

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6851(3)
_cell_length_b                   12.5057(5)
_cell_length_c                   13.9472(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1340.43(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7724
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15650
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2362
_reflns_number_gt                2246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.0978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2362
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.16520(6) 0.94029(3) 0.40643(3) 0.04540(15) Uani 1 1 d . . .
O1 O 0.32355(18) 0.89755(12) 0.36009(10) 0.0664(4) Uani 1 1 d . . .
C1 C -0.0013(2) 0.98457(13) 0.32538(11) 0.0465(4) Uani 1 1 d . . .
C2 C 0.0365(3) 1.06207(15) 0.25589(13) 0.0538(4) Uani 1 1 d . . .
C3 C -0.0965(3) 1.09130(19) 0.19440(15) 0.0722(6) Uani 1 1 d . . .
H3A H -0.0741 1.1417 0.1469 0.087 Uiso 1 1 calc R . .
C4 C -0.2606(3) 1.0483(3) 0.20113(19) 0.0863(8) Uani 1 1 d . . .
H4A H -0.3470 1.0705 0.1589 0.104 Uiso 1 1 calc R . .
C5 C -0.2981(3) 0.9731(2) 0.26959(18) 0.0881(8) Uani 1 1 d . . .
H5A H -0.4091 0.9439 0.2741 0.106 Uiso 1 1 calc R . .
C6 C -0.1689(3) 0.94170(19) 0.33121(15) 0.0649(5) Uani 1 1 d . . .
H6A H -0.1932 0.8908 0.3779 0.078 Uiso 1 1 calc R . .
C7 C 0.2086(3) 1.04752(16) 0.48852(13) 0.0657(6) Uani 1 1 d . . .
C8 C 0.0771(5) 1.1033(2) 0.5302(2) 0.1009(10) Uani 1 1 d . . .
H8A H -0.0379 1.0892 0.5137 0.121 Uiso 1 1 calc R . .
C9 C 0.1154(9) 1.1815(3) 0.5977(3) 0.1507(19) Uani 1 1 d . . .
H9A H 0.0262 1.2204 0.6263 0.181 Uiso 1 1 calc R . .
C10 C 0.2826(10) 1.2008(3) 0.6216(3) 0.167(3) Uani 1 1 d . . .
H10A H 0.3074 1.2522 0.6679 0.200 Uiso 1 1 calc R . .
C11 C 0.4155(8) 1.1467(4) 0.5795(3) 0.156(2) Uani 1 1 d . . .
H11A H 0.5299 1.1629 0.5956 0.187 Uiso 1 1 calc R . .
C12 C 0.3815(5) 1.0678(3) 0.5127(2) 0.1052(11) Uani 1 1 d . . .
H12A H 0.4716 1.0292 0.4847 0.126 Uiso 1 1 calc R . .
C13 C 0.2136(3) 1.1102(2) 0.24516(17) 0.0792(7) Uani 1 1 d . . .
H13A H 0.2126 1.1609 0.1935 0.119 Uiso 1 1 calc R . .
H13B H 0.2965 1.0548 0.2315 0.119 Uiso 1 1 calc R . .
H13C H 0.2455 1.1457 0.3036 0.119 Uiso 1 1 calc R . .
C14 C 0.0645(3) 0.84348(14) 0.47946(13) 0.0500(4) Uani 1 1 d . . .
C15 C 0.0092(3) 0.77689(15) 0.53030(13) 0.0591(5) Uani 1 1 d . . .
H15A H -0.0363 0.7195 0.5685 0.089 Uiso 1 1 d R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4780(15) . ?
P1 C14 1.7613(18) . ?
P1 C7 1.794(2) . ?
P1 C1 1.7950(18) . ?
C1 C6 1.397(3) . ?
C1 C2 1.401(2) . ?
C2 C3 1.384(3) . ?
C2 C13 1.496(3) . ?
C3 C4 1.374(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.371(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.359(4) . ?
C7 C12 1.394(4) . ?
C8 C9 1.389(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.350(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.359(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.173(3) . ?
C15 H15A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C14 111.47(8) . . ?
O1 P1 C7 113.35(11) . . ?
C14 P1 C7 103.09(9) . . ?
O1 P1 C1 115.03(8) . . ?
C14 P1 C1 105.25(9) . . ?
C7 P1 C1 107.68(9) . . ?
C6 C1 C2 119.79(17) . . ?
C6 C1 P1 120.13(14) . . ?
C2 C1 P1 120.08(15) . . ?
C3 C2 C1 117.28(19) . . ?
C3 C2 C13 120.28(18) . . ?
C1 C2 C13 122.42(17) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 H3A 118.9 . . ?
C2 C3 H3A 118.9 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 H6A 119.3 . . ?
C1 C6 H6A 119.3 . . ?
C8 C7 C12 120.8(3) . . ?
C8 C7 P1 121.2(2) . . ?
C12 C7 P1 117.9(2) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C10 C9 C8 119.7(5) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 118.2(4) . . ?
C7 C12 H12A 120.9 . . ?
C11 C12 H12A 120.9 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 P1 175.16(19) . . ?
C14 C15 H15A 176.4 . . ?

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
O1 P1 C1 C6 123.55(17) . . . . ?
C14 P1 C1 C6 0.46(18) . . . . ?
C7 P1 C1 C6 -109.01(17) . . . . ?
O1 P1 C1 C2 -56.29(17) . . . . ?
C14 P1 C1 C2 -179.39(14) . . . . ?
C7 P1 C1 C2 71.15(17) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
P1 C1 C2 C3 178.78(15) . . . . ?
C6 C1 C2 C13 -179.3(2) . . . . ?
P1 C1 C2 C13 0.6(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C13 C2 C3 C4 179.4(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
P1 C1 C6 C5 -179.25(19) . . . . ?
O1 P1 C7 C8 173.36(19) . . . . ?
C14 P1 C7 C8 -66.0(2) . . . . ?
C1 P1 C7 C8 45.0(2) . . . . ?
O1 P1 C7 C12 -10.4(2) . . . . ?
C14 P1 C7 C12 110.22(19) . . . . ?
C1 P1 C7 C12 -138.83(19) . . . . ?
C12 C7 C8 C9 0.1(4) . . . . ?
P1 C7 C8 C9 176.2(2) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
C9 C10 C11 C12 -2.0(7) . . . . ?
C8 C7 C12 C11 -0.7(4) . . . . ?
P1 C7 C12 C11 -176.9(2) . . . . ?
C10 C11 C12 C7 1.6(6) . . . . ?
O1 P1 C14 C15 41(2) . . . . ?
C7 P1 C14 C15 -81(2) . . . . ?
C1 P1 C14 C15 167(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.031
