# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_L2
_database_code_depnum_ccdc_archive 'CCDC 1497885'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H20 N O3 P'
_chemical_formula_sum            'C15 H20 N O3 P'
_chemical_formula_weight         293.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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'
'-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                   8.0100(2)
_cell_length_b                   11.3652(3)
_cell_length_c                   32.3906(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2948.69(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8872
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0469 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.9308.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.780
_diffrn_reflns_theta_min         1.257
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2827
_reflns_number_total             3146
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+1.5621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0764
_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:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.37824(4) 0.70860(3) 0.65390(2) 0.01152(9) Uani 1 1 d . . . . .
O1 O 0.53198(11) 0.81354(7) 0.58998(3) 0.01460(19) Uani 1 1 d . . . . .
O2 O 0.50045(11) 0.65903(7) 0.54238(2) 0.01486(19) Uani 1 1 d . . . . .
O3 O 0.36948(10) 0.53733(7) 0.59135(2) 0.01267(18) Uani 1 1 d . . . . .
N1 N 0.50832(14) 0.63843(9) 0.72452(3) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.57592(15) 0.73536(10) 0.62371(4) 0.0130(2) Uani 1 1 d . . . . .
C2 C 0.42617(16) 0.76296(10) 0.55905(4) 0.0150(2) Uani 1 1 d . . . . .
C3 C 0.25585(15) 0.72974(11) 0.57670(4) 0.0148(2) Uani 1 1 d . . . . .
H3A H 0.1839 0.7022 0.5546 0.018 Uiso 1 1 calc R . . . .
H3B H 0.2043 0.7985 0.5890 0.018 Uiso 1 1 calc R . . . .
C4 C 0.27432(14) 0.63323(10) 0.60934(4) 0.0128(2) Uani 1 1 d . . . . .
C5 C 0.64505(15) 0.62179(10) 0.60548(4) 0.0134(2) Uani 1 1 d . . . . .
H5A H 0.6619 0.5648 0.6274 0.016 Uiso 1 1 calc R . . . .
H5B H 0.7523 0.6373 0.5927 0.016 Uiso 1 1 calc R . . . .
C6 C 0.52559(15) 0.57112(10) 0.57338(4) 0.0133(2) Uani 1 1 d . . . . .
C7 C 0.70251(16) 0.80069(11) 0.64998(4) 0.0176(3) Uani 1 1 d . . . . .
H7A H 0.6575 0.8756 0.6579 0.026 Uiso 1 1 calc GR . . . .
H7B H 0.8031 0.8124 0.6344 0.026 Uiso 1 1 calc GR . . . .
H7C H 0.7270 0.7554 0.6742 0.026 Uiso 1 1 calc GR . . . .
C8 C 0.41541(18) 0.85145(11) 0.52444(4) 0.0208(3) Uani 1 1 d . . . . .
H8A H 0.3641 0.9223 0.5344 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.3497 0.8195 0.5023 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.5256 0.8689 0.5145 0.031 Uiso 1 1 calc GR . . . .
C9 C 0.10669(15) 0.58178(12) 0.62159(4) 0.0182(3) Uani 1 1 d . . . . .
H9A H 0.1233 0.5201 0.6414 0.027 Uiso 1 1 calc GR . . . .
H9B H 0.0523 0.5503 0.5976 0.027 Uiso 1 1 calc GR . . . .
H9C H 0.0384 0.6423 0.6335 0.027 Uiso 1 1 calc GR . . . .
C10 C 0.59304(16) 0.46340(11) 0.55182(4) 0.0176(3) Uani 1 1 d . . . . .
H10A H 0.5119 0.4350 0.5324 0.026 Uiso 1 1 calc GR . . . .
H10B H 0.6160 0.4033 0.5718 0.026 Uiso 1 1 calc GR . . . .
H10C H 0.6941 0.4834 0.5375 0.026 Uiso 1 1 calc GR . . . .
C11 C 0.44345(15) 0.59165(10) 0.68970(4) 0.0131(2) Uani 1 1 d . . . . .
C12 C 0.42393(15) 0.47055(11) 0.68454(4) 0.0157(2) Uani 1 1 d . . . . .
H12 H 0.3805 0.4404 0.6601 0.019 Uiso 1 1 calc R . . . .
C13 C 0.47026(16) 0.39578(11) 0.71641(4) 0.0184(3) Uani 1 1 d . . . . .
H13 H 0.4553 0.3149 0.7139 0.022 Uiso 1 1 calc R . . . .
C14 C 0.53878(17) 0.44262(11) 0.75190(4) 0.0209(3) Uani 1 1 d . . . . .
H14 H 0.5720 0.3944 0.7736 0.025 Uiso 1 1 calc R . . . .
C15 C 0.55647(18) 0.56399(12) 0.75416(4) 0.0242(3) Uani 1 1 d . . . . .
H15 H 0.6049 0.5955 0.7778 0.029 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 C1 1.8857(12) . ?
P1 C4 1.8734(12) . ?
P1 C11 1.8395(12) . ?
O1 C1 1.4515(14) . ?
O1 C2 1.4326(14) . ?
O2 C2 1.4285(14) . ?
O2 C6 1.4307(14) . ?
O3 C4 1.4520(13) . ?
O3 C6 1.4317(14) . ?
N1 C11 1.3509(16) . ?
N1 C15 1.3366(16) . ?
C1 C5 1.5235(16) . ?
C1 C7 1.5178(16) . ?
C2 C3 1.5265(18) . ?
C2 C8 1.5084(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5307(16) . ?
C4 C9 1.5173(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5258(16) . ?
C6 C10 1.5095(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.3952(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3875(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.3806(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.3886(18) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 P1 C1 92.71(5) . . ?
C11 P1 C1 101.83(5) . . ?
C11 P1 C4 106.34(5) . . ?
C2 O1 C1 115.10(9) . . ?
C2 O2 C6 111.77(9) . . ?
C6 O3 C4 114.85(9) . . ?
C15 N1 C11 117.49(11) . . ?
O1 C1 P1 106.59(8) . . ?
O1 C1 C5 108.36(9) . . ?
O1 C1 C7 106.53(9) . . ?
C5 C1 P1 111.68(8) . . ?
C7 C1 P1 110.43(8) . . ?
C7 C1 C5 112.88(10) . . ?
O1 C2 C3 111.48(9) . . ?
O1 C2 C8 106.61(10) . . ?
O2 C2 O1 110.46(9) . . ?
O2 C2 C3 108.01(9) . . ?
O2 C2 C8 107.11(10) . . ?
C8 C2 C3 113.09(10) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.46(10) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
O3 C4 P1 114.78(8) . . ?
O3 C4 C3 108.14(9) . . ?
O3 C4 C9 106.27(9) . . ?
C3 C4 P1 104.33(8) . . ?
C9 C4 P1 111.59(8) . . ?
C9 C4 C3 111.79(10) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 C6 110.84(10) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O2 C6 O3 110.47(9) . . ?
O2 C6 C5 107.63(9) . . ?
O2 C6 C10 106.98(9) . . ?
O3 C6 C5 111.84(9) . . ?
O3 C6 C10 106.45(10) . . ?
C10 C6 C5 113.39(10) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 110.56(8) . . ?
N1 C11 C12 122.09(11) . . ?
C12 C11 P1 127.27(9) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.03(12) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.31(12) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 121.1 . . ?
C13 C14 C15 117.88(12) . . ?
C15 C14 H14 121.1 . . ?
N1 C15 C14 124.15(12) . . ?
N1 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C5 C6 65.11(11) . . . . ?
P1 C11 C12 C13 -175.33(10) . . . . ?
O1 C1 C5 C6 -52.01(12) . . . . ?
O1 C2 C3 C4 -64.11(12) . . . . ?
O2 C2 C3 C4 57.42(12) . . . . ?
N1 C11 C12 C13 0.97(19) . . . . ?
C1 P1 C4 O3 52.85(9) . . . . ?
C1 P1 C4 C3 -65.30(8) . . . . ?
C1 P1 C4 C9 173.83(9) . . . . ?
C1 P1 C11 N1 88.41(9) . . . . ?
C1 P1 C11 C12 -94.93(12) . . . . ?
C1 O1 C2 O2 -56.28(13) . . . . ?
C1 O1 C2 C3 63.81(12) . . . . ?
C1 O1 C2 C8 -172.33(10) . . . . ?
C1 C5 C6 O2 57.49(12) . . . . ?
C1 C5 C6 O3 -64.01(12) . . . . ?
C1 C5 C6 C10 175.61(10) . . . . ?
C2 O1 C1 P1 -68.37(10) . . . . ?
C2 O1 C1 C5 51.97(12) . . . . ?
C2 O1 C1 C7 173.70(10) . . . . ?
C2 O2 C6 O3 60.74(12) . . . . ?
C2 O2 C6 C5 -61.62(12) . . . . ?
C2 O2 C6 C10 176.20(10) . . . . ?
C2 C3 C4 P1 70.15(10) . . . . ?
C2 C3 C4 O3 -52.46(12) . . . . ?
C2 C3 C4 C9 -169.11(10) . . . . ?
C4 P1 C1 O1 63.90(8) . . . . ?
C4 P1 C1 C5 -54.28(9) . . . . ?
C4 P1 C1 C7 179.23(9) . . . . ?
C4 P1 C11 N1 -175.17(8) . . . . ?
C4 P1 C11 C12 1.48(13) . . . . ?
C4 O3 C6 O2 -56.97(12) . . . . ?
C4 O3 C6 C5 62.88(12) . . . . ?
C4 O3 C6 C10 -172.77(9) . . . . ?
C6 O2 C2 O1 60.88(12) . . . . ?
C6 O2 C2 C3 -61.28(12) . . . . ?
C6 O2 C2 C8 176.61(10) . . . . ?
C6 O3 C4 P1 -63.02(11) . . . . ?
C6 O3 C4 C3 52.96(12) . . . . ?
C6 O3 C4 C9 173.13(9) . . . . ?
C7 C1 C5 C6 -169.75(10) . . . . ?
C8 C2 C3 C4 175.78(10) . . . . ?
C11 P1 C1 O1 171.21(7) . . . . ?
C11 P1 C1 C5 53.04(9) . . . . ?
C11 P1 C1 C7 -73.45(9) . . . . ?
C11 P1 C4 O3 -50.31(9) . . . . ?
C11 P1 C4 C3 -168.47(8) . . . . ?
C11 P1 C4 C9 70.66(9) . . . . ?
C11 N1 C15 C14 -2.2(2) . . . . ?
C11 C12 C13 C14 -1.82(19) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 N1 1.4(2) . . . . ?
C15 N1 C11 P1 177.87(10) . . . . ?
C15 N1 C11 C12 1.02(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_meso_1c
_database_code_depnum_ccdc_archive 'CCDC 1497886'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H44 Cl2 N2 O6 P2 Pt'
_chemical_formula_sum            'C32 H44 Cl2 N2 O6 P2 Pt'
_chemical_formula_weight         880.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Pt Pt -1.7033 8.3905 '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                   8.2419(2)
_cell_length_b                   10.5796(3)
_cell_length_c                   11.4154(3)
_cell_angle_alpha                117.5507(14)
_cell_angle_beta                 91.9459(15)
_cell_angle_gamma                100.8508(15)
_cell_volume                     858.31(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6226
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.381
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0550 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.9105.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.121
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15546
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.924
_diffrn_reflns_theta_min         2.032
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4042
_reflns_number_total             4100
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.118
_refine_diff_density_min         -1.201
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.052
_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)+(0.0072P)²+1.4934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0469
_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:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Pt1 Pt 0.5000 0.5000 0.0000 0.01095(5) Uani 1 2 d S T P . .
Cl1 Cl 0.30752(9) 0.32279(8) 0.01859(7) 0.01774(15) Uani 1 1 d . . . . .
P1 P 0.64188(9) 0.53651(8) 0.19674(7) 0.01220(15) Uani 1 1 d . . . . .
O1 O 0.9149(2) 0.6525(2) 0.38500(19) 0.0170(4) Uani 1 1 d . . . . .
O2 O 0.5714(3) 0.7821(2) 0.3859(2) 0.0182(5) Uani 1 1 d . . . . .
O3 O 0.8223(3) 0.8609(2) 0.53188(19) 0.0176(4) Uani 1 1 d . . . . .
N1 N 0.5971(3) 0.3047(3) 0.2498(2) 0.0179(5) Uani 1 1 d . . . . .
C1 C 0.5511(4) 0.6299(3) 0.3560(3) 0.0144(6) Uani 1 1 d . . . . .
C2 C 0.7406(4) 0.8686(3) 0.4244(3) 0.0185(6) Uani 1 1 d . . . . .
C3 C 0.8394(4) 0.8141(3) 0.3081(3) 0.0156(6) Uani 1 1 d . . . . .
H3A H 0.7837 0.8157 0.2328 0.019 Uiso 1 1 calc R . . . .
H3B H 0.9495 0.8788 0.3330 0.019 Uiso 1 1 calc R . . . .
C4 C 0.8561(4) 0.6595(3) 0.2682(3) 0.0151(6) Uani 1 1 d . . . . .
C5 C 0.6491(3) 0.6254(3) 0.4674(3) 0.0120(6) Uani 1 1 d . . . . .
H5A H 0.6495 0.5245 0.4424 0.014 Uiso 1 1 calc R . . . .
H5B H 0.5951 0.6642 0.5469 0.014 Uiso 1 1 calc R . . . .
C6 C 0.8265(4) 0.7132(3) 0.4981(3) 0.0162(6) Uani 1 1 d . . . . .
C7 C 0.3668(4) 0.5718(3) 0.3428(3) 0.0192(6) Uani 1 1 d . . . . .
H7A H 0.3095 0.5861 0.2769 0.029 Uiso 1 1 calc GR . . . .
H7B H 0.3284 0.6229 0.4271 0.029 Uiso 1 1 calc GR . . . .
H7C H 0.3446 0.4691 0.3161 0.029 Uiso 1 1 calc GR . . . .
C8 C 0.7273(4) 1.0258(3) 0.4763(3) 0.0273(8) Uani 1 1 d . . . . .
H8A H 0.6631 1.0336 0.4091 0.041 Uiso 1 1 calc GR . . . .
H8B H 0.8370 1.0879 0.4976 0.041 Uiso 1 1 calc GR . . . .
H8C H 0.6734 1.0556 0.5550 0.041 Uiso 1 1 calc GR . . . .
C9 C 0.9842(4) 0.6158(3) 0.1741(3) 0.0187(6) Uani 1 1 d . . . . .
H9A H 0.9998 0.5216 0.1578 0.028 Uiso 1 1 calc GR . . . .
H9B H 1.0881 0.6871 0.2135 0.028 Uiso 1 1 calc GR . . . .
H9C H 0.9460 0.6108 0.0914 0.028 Uiso 1 1 calc GR . . . .
C10 C 0.9284(4) 0.7182(4) 0.6129(3) 0.0241(7) Uani 1 1 d . . . . .
H10A H 1.0366 0.7817 0.6309 0.036 Uiso 1 1 calc GR . . . .
H10B H 0.9407 0.6214 0.5902 0.036 Uiso 1 1 calc GR . . . .
H10C H 0.8731 0.7547 0.6906 0.036 Uiso 1 1 calc GR . . . .
C11 C 0.6633(4) 0.3556(3) 0.1698(3) 0.0141(6) Uani 1 1 d . . . . .
C12 C 0.7368(4) 0.2732(3) 0.0598(3) 0.0192(7) Uani 1 1 d . . . . .
H12 H 0.7776 0.3121 0.0055 0.023 Uiso 1 1 calc R . . . .
C13 C 0.7490(4) 0.1330(3) 0.0313(3) 0.0226(7) Uani 1 1 d . . . . .
C14 C 0.6817(4) 0.0806(3) 0.1145(3) 0.0247(7) Uani 1 1 d . . . . .
H14 H 0.6870 -0.0126 0.0999 0.030 Uiso 1 1 calc R . . . .
C15 C 0.6066(4) 0.1681(3) 0.2197(3) 0.0231(7) Uani 1 1 d . . . . .
H15 H 0.5598 0.1297 0.2727 0.028 Uiso 1 1 calc R . . . .
C16 C 0.8288(5) 0.0426(4) -0.0859(4) 0.0385(10) Uani 1 1 d . . . . .
H16A H 0.7771 0.0373 -0.1651 0.058 Uiso 1 1 calc GR . . . .
H16B H 0.8147 -0.0544 -0.0963 0.058 Uiso 1 1 calc GR . . . .
H16C H 0.9456 0.0869 -0.0712 0.058 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
Pt1 Cl1 2.3125(7) . ?
Pt1 Cl1 2.3125(7) 2_665 ?
Pt1 P1 2.3259(7) . ?
Pt1 P1 2.3259(7) 2_665 ?
P1 C1 1.884(3) . ?
P1 C4 1.879(3) . ?
P1 C11 1.837(3) . ?
O1 C4 1.443(3) . ?
O1 C6 1.444(3) . ?
O2 C1 1.458(3) . ?
O2 C2 1.442(4) . ?
O3 C2 1.422(4) . ?
O3 C6 1.433(3) . ?
N1 C11 1.343(4) . ?
N1 C15 1.340(4) . ?
C1 C5 1.507(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.517(4) . ?
C2 C8 1.514(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.516(4) . ?
C4 C9 1.511(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.509(4) . ?
C6 C10 1.506(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.392(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C13 C14 1.388(5) . ?
C13 C16 1.500(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
Cl1 Pt1 Cl1 180.0 . 2_665 ?
Cl1 Pt1 P1 94.77(3) 2_665 . ?
Cl1 Pt1 P1 85.23(3) . . ?
Cl1 Pt1 P1 94.77(3) . 2_665 ?
Cl1 Pt1 P1 85.23(3) 2_665 2_665 ?
P1 Pt1 P1 180.0 2_665 . ?
C1 P1 Pt1 118.05(9) . . ?
C4 P1 Pt1 122.04(10) . . ?
C4 P1 C1 94.10(13) . . ?
C11 P1 Pt1 106.67(9) . . ?
C11 P1 C1 109.47(13) . . ?
C11 P1 C4 105.41(13) . . ?
C4 O1 C6 116.0(2) . . ?
C2 O2 C1 115.7(2) . . ?
C2 O3 C6 111.8(2) . . ?
C15 N1 C11 116.3(3) . . ?
O2 C1 P1 106.28(18) . . ?
O2 C1 C5 108.8(2) . . ?
O2 C1 C7 105.6(2) . . ?
C5 C1 P1 109.46(19) . . ?
C7 C1 P1 113.5(2) . . ?
C7 C1 C5 112.9(2) . . ?
O2 C2 C3 110.5(2) . . ?
O2 C2 C8 105.8(2) . . ?
O3 C2 O2 111.1(2) . . ?
O3 C2 C3 108.2(2) . . ?
O3 C2 C8 106.9(2) . . ?
C8 C2 C3 114.2(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.9(2) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
O1 C4 P1 109.01(19) . . ?
O1 C4 C3 109.4(2) . . ?
O1 C4 C9 106.3(2) . . ?
C3 C4 P1 107.00(19) . . ?
C9 C4 P1 113.6(2) . . ?
C9 C4 C3 111.5(2) . . ?
C1 C5 H5A 109.3 . . ?
C1 C5 H5B 109.3 . . ?
C1 C5 C6 111.8(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
O1 C6 C5 111.0(2) . . ?
O1 C6 C10 105.9(2) . . ?
O3 C6 O1 110.0(2) . . ?
O3 C6 C5 108.1(2) . . ?
O3 C6 C10 107.6(2) . . ?
C10 C6 C5 114.2(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 119.0(2) . . ?
N1 C11 C12 123.2(3) . . ?
C12 C11 P1 117.6(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C16 121.0(3) . . ?
C14 C13 C12 116.9(3) . . ?
C14 C13 C16 122.1(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
N1 C15 C14 124.2(3) . . ?
N1 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Pt1 P1 C1 O2 -69.83(19) . . . . ?
Pt1 P1 C1 C5 172.87(15) . . . . ?
Pt1 P1 C1 C7 45.7(2) . . . . ?
Pt1 P1 C4 O1 -176.40(13) . . . . ?
Pt1 P1 C4 C3 65.4(2) . . . . ?
Pt1 P1 C4 C9 -58.1(2) . . . . ?
Pt1 P1 C11 N1 -120.6(2) . . . . ?
Pt1 P1 C11 C12 54.5(2) . . . . ?
P1 C1 C5 C6 64.9(3) . . . . ?
P1 C11 C12 C13 -177.0(2) . . . . ?
O2 C1 C5 C6 -50.8(3) . . . . ?
O2 C2 C3 C4 -64.5(3) . . . . ?
O3 C2 C3 C4 57.4(3) . . . . ?
N1 C11 C12 C13 -2.1(5) . . . . ?
C1 P1 C4 O1 56.66(19) . . . . ?
C1 P1 C4 C3 -61.5(2) . . . . ?
C1 P1 C4 C9 175.0(2) . . . . ?
C1 P1 C11 N1 8.2(3) . . . . ?
C1 P1 C11 C12 -176.7(2) . . . . ?
C1 O2 C2 O3 -53.2(3) . . . . ?
C1 O2 C2 C3 66.9(3) . . . . ?
C1 O2 C2 C8 -169.0(2) . . . . ?
C1 C5 C6 O1 -63.0(3) . . . . ?
C1 C5 C6 O3 57.7(3) . . . . ?
C1 C5 C6 C10 177.5(2) . . . . ?
C2 O2 C1 P1 -68.9(3) . . . . ?
C2 O2 C1 C5 48.9(3) . . . . ?
C2 O2 C1 C7 170.3(2) . . . . ?
C2 O3 C6 O1 60.1(3) . . . . ?
C2 O3 C6 C5 -61.3(3) . . . . ?
C2 O3 C6 C10 174.9(2) . . . . ?
C2 C3 C4 P1 67.7(3) . . . . ?
C2 C3 C4 O1 -50.3(3) . . . . ?
C2 C3 C4 C9 -167.5(2) . . . . ?
C4 P1 C1 O2 60.03(19) . . . . ?
C4 P1 C1 C5 -57.3(2) . . . . ?
C4 P1 C1 C7 175.6(2) . . . . ?
C4 P1 C11 N1 108.3(2) . . . . ?
C4 P1 C11 C12 -76.6(3) . . . . ?
C4 O1 C6 O3 -53.9(3) . . . . ?
C4 O1 C6 C5 65.7(3) . . . . ?
C4 O1 C6 C10 -169.9(2) . . . . ?
C6 O1 C4 P1 -67.1(3) . . . . ?
C6 O1 C4 C3 49.6(3) . . . . ?
C6 O1 C4 C9 170.1(2) . . . . ?
C6 O3 C2 O2 59.0(3) . . . . ?
C6 O3 C2 C3 -62.5(3) . . . . ?
C6 O3 C2 C8 174.0(2) . . . . ?
C7 C1 C5 C6 -167.6(2) . . . . ?
C8 C2 C3 C4 176.4(2) . . . . ?
C11 P1 C1 O2 167.96(17) . . . . ?
C11 P1 C1 C5 50.7(2) . . . . ?
C11 P1 C1 C7 -76.5(2) . . . . ?
C11 P1 C4 O1 -54.8(2) . . . . ?
C11 P1 C4 C3 -173.00(19) . . . . ?
C11 P1 C4 C9 63.5(2) . . . . ?
C11 N1 C15 C14 1.2(5) . . . . ?
C11 C12 C13 C14 1.6(5) . . . . ?
C11 C12 C13 C16 -179.5(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 N1 -1.7(5) . . . . ?
C15 N1 C11 P1 175.6(2) . . . . ?
C15 N1 C11 C12 0.8(4) . . . . ?
C16 C13 C14 C15 -178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_meso_1d
_database_code_depnum_ccdc_archive 'CCDC 1497887'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H44 Cl2 N2 O6 P2 Pt'
_chemical_formula_sum            'C32 H44 Cl2 N2 O6 P2 Pt'
_chemical_formula_weight         880.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Pt Pt -1.7033 8.3905 '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                   8.7414(2)
_cell_length_b                   10.2111(3)
_cell_length_c                   11.1847(3)
_cell_angle_alpha                64.6586(13)
_cell_angle_beta                 88.5905(15)
_cell_angle_gamma                77.9537(15)
_cell_volume                     880.03(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.273
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0743 before and 0.0343 after correction.
The Ratio of minimum to maximum transmission is 0.7340.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.055
_diffrn_reflns_theta_min         2.020
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4254
_reflns_number_total             4268
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.167
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.112
_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     210
_refine_ls_number_reflns         4268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.070
_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)+(0.0358P)²+0.6456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0566
_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:
 C5(H5A,H5B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C),
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C4 C 0.0581(3) 0.1295(3) 0.2509(2) 0.0166(5) Uani 1 1 d . . . . .
C5 C 0.1496(3) 0.0142(3) 0.3761(2) 0.0151(5) Uani 1 1 d . . . . .
H5A H 0.0981 -0.0686 0.4149 0.018 Uiso 1 1 calc R . . . .
H5B H 0.1517 0.0561 0.4391 0.018 Uiso 1 1 calc R . . . .
C6 C 0.3143(3) -0.0411(3) 0.3514(3) 0.0189(5) Uani 1 1 d . . . . .
C1 C 0.3436(3) 0.1949(3) 0.1696(3) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.3282(3) 0.1257(3) 0.0778(2) 0.0150(5) Uani 1 1 d . . . . .
H2A H 0.4318 0.0812 0.0627 0.018 Uiso 1 1 calc R . . . .
H2B H 0.2784 0.2019 -0.0069 0.018 Uiso 1 1 calc R . . . .
C3 C 0.2328(3) 0.0085(3) 0.1341(3) 0.0207(5) Uani 1 1 d . . . . .
C9 C -0.1150(3) 0.1633(4) 0.2694(3) 0.0269(6) Uani 1 1 d . . . . .
H9A H -0.1322 0.2094 0.3290 0.040 Uiso 1 1 calc GR . . . .
H9B H -0.1519 0.0727 0.3058 0.040 Uiso 1 1 calc GR . . . .
H9C H -0.1709 0.2294 0.1852 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.4066(5) -0.1628(4) 0.4745(3) 0.0357(8) Uani 1 1 d . . . . .
H10A H 0.3533 -0.2432 0.5110 0.054 Uiso 1 1 calc GR . . . .
H10B H 0.4162 -0.1251 0.5386 0.054 Uiso 1 1 calc GR . . . .
H10C H 0.5091 -0.1978 0.4525 0.054 Uiso 1 1 calc GR . . . .
C7 C 0.4626(3) 0.2918(3) 0.1246(3) 0.0249(6) Uani 1 1 d . . . . .
H7A H 0.4251 0.3745 0.0407 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.5605 0.2347 0.1153 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.4777 0.3275 0.1891 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.2182(5) -0.0727(4) 0.0509(3) 0.0374(8) Uani 1 1 d . . . . .
H8A H 0.1580 -0.1465 0.0947 0.056 Uiso 1 1 calc GR . . . .
H8B H 0.3208 -0.1200 0.0392 0.056 Uiso 1 1 calc GR . . . .
H8C H 0.1666 -0.0033 -0.0342 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.1754(3) 0.3618(3) 0.3093(3) 0.0195(5) Uani 1 1 d . . . . .
C12 C 0.2309(4) 0.4911(3) 0.2676(3) 0.0285(6) Uani 1 1 d . . . . .
H12 H 0.2506 0.5425 0.1794 0.034 Uiso 1 1 calc R . . . .
C13 C 0.2566(4) 0.5424(4) 0.3609(3) 0.0325(7) Uani 1 1 d . . . . .
H13 H 0.2949 0.6280 0.3368 0.039 Uiso 1 1 calc R . . . .
C14 C 0.2235(4) 0.4626(3) 0.4904(3) 0.0277(6) Uani 1 1 d . . . . .
H14 H 0.2397 0.4941 0.5547 0.033 Uiso 1 1 calc R . . . .
C15 C 0.1664(4) 0.3357(3) 0.5240(3) 0.0242(6) Uani 1 1 d . . . . .
C16 C 0.1345(5) 0.2434(4) 0.6640(3) 0.0374(8) Uani 1 1 d . . . . .
H16A H 0.0386 0.2115 0.6643 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.1251 0.3013 0.7135 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.2193 0.1581 0.7039 0.056 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.17109(8) 0.47093(8) -0.15220(6) 0.02552(14) Uani 1 1 d . . . . .
N1 N 0.1421(3) 0.2853(3) 0.4337(2) 0.0214(5) Uani 1 1 d . . . . .
O2 O 0.0739(2) 0.0730(2) 0.15041(19) 0.0231(4) Uani 1 1 d . . . . .
O1 O 0.3997(2) 0.0773(2) 0.3012(2) 0.0235(4) Uani 1 1 d . . . . .
O3 O 0.3085(2) -0.1018(2) 0.25863(19) 0.0208(4) Uani 1 1 d . . . . .
P1 P 0.14347(7) 0.29939(7) 0.18143(6) 0.01420(12) Uani 1 1 d . . . . .
Pt1 Pt 0.0000 0.5000 0.0000 0.01522(5) Uani 1 2 d S T P . .


_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
C4 C5 1.497(3) . ?
C4 C9 1.509(4) . ?
C4 O2 1.460(3) . ?
C4 P1 1.878(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.497(4) . ?
C6 C10 1.504(4) . ?
C6 O1 1.452(3) . ?
C6 O3 1.425(3) . ?
C1 C2 1.497(3) . ?
C1 C7 1.514(4) . ?
C1 O1 1.458(3) . ?
C1 P1 1.883(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.506(4) . ?
C3 C8 1.511(4) . ?
C3 O2 1.450(3) . ?
C3 O3 1.427(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 C12 1.389(4) . ?
C11 N1 1.332(4) . ?
C11 P1 1.845(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(4) . ?
C15 C16 1.498(4) . ?
C15 N1 1.354(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
Cl1 Pt1 2.3119(6) . ?
P1 Pt1 2.3198(6) . ?
Pt1 Cl1 2.3119(6) 2_565 ?
Pt1 P1 2.3197(6) 2_565 ?

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
C5 C4 C9 111.9(2) . . ?
C5 C4 P1 110.53(17) . . ?
C9 C4 P1 113.14(19) . . ?
O2 C4 C5 109.0(2) . . ?
O2 C4 C9 106.5(2) . . ?
O2 C4 P1 105.45(16) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.7(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 C10 112.8(2) . . ?
O1 C6 C5 111.4(2) . . ?
O1 C6 C10 107.0(2) . . ?
O3 C6 C5 108.3(2) . . ?
O3 C6 C10 107.0(2) . . ?
O3 C6 O1 110.3(2) . . ?
C2 C1 C7 110.9(2) . . ?
C2 C1 P1 108.46(17) . . ?
C7 C1 P1 112.91(19) . . ?
O1 C1 C2 108.7(2) . . ?
O1 C1 C7 107.5(2) . . ?
O1 C1 P1 108.17(16) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.4(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 C8 114.9(2) . . ?
O2 C3 C2 110.8(2) . . ?
O2 C3 C8 106.2(2) . . ?
O3 C3 C2 108.1(2) . . ?
O3 C3 C8 106.0(2) . . ?
O3 C3 O2 110.7(2) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C11 P1 116.6(2) . . ?
N1 C11 C12 123.4(2) . . ?
N1 C11 P1 120.0(2) . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.5(3) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 121.5(3) . . ?
N1 C15 C14 122.0(3) . . ?
N1 C15 C16 116.4(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 N1 C15 117.9(2) . . ?
C3 O2 C4 115.55(19) . . ?
C6 O1 C1 115.31(19) . . ?
C6 O3 C3 111.38(19) . . ?
C4 P1 C1 93.99(11) . . ?
C4 P1 Pt1 115.23(8) . . ?
C1 P1 Pt1 122.65(8) . . ?
C11 P1 C4 111.54(12) . . ?
C11 P1 C1 103.98(12) . . ?
C11 P1 Pt1 108.42(9) . . ?
Cl1 Pt1 Cl1 180.0 2_565 . ?
Cl1 Pt1 P1 85.39(2) . 2_565 ?
Cl1 Pt1 P1 94.61(2) 2_565 2_565 ?
Cl1 Pt1 P1 85.39(2) 2_565 . ?
Cl1 Pt1 P1 94.61(2) . . ?
P1 Pt1 P1 180.0 2_565 . ?

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
C4 C5 C6 C10 -177.0(2) . . . . ?
C4 C5 C6 O1 62.6(3) . . . . ?
C4 C5 C6 O3 -58.9(3) . . . . ?
C5 C4 O2 C3 -48.5(3) . . . . ?
C5 C4 P1 C1 57.42(19) . . . . ?
C5 C4 P1 C11 -49.3(2) . . . . ?
C5 C4 P1 Pt1 -173.47(14) . . . . ?
C5 C6 O1 C1 -66.4(3) . . . . ?
C5 C6 O3 C3 62.4(3) . . . . ?
C1 C2 C3 C8 -177.1(2) . . . . ?
C1 C2 C3 O2 62.6(3) . . . . ?
C1 C2 C3 O3 -58.9(3) . . . . ?
C2 C1 O1 C6 -49.9(3) . . . . ?
C2 C1 P1 C4 60.93(18) . . . . ?
C2 C1 P1 C11 174.30(17) . . . . ?
C2 C1 P1 Pt1 -62.59(19) . . . . ?
C2 C3 O2 C4 -67.3(3) . . . . ?
C2 C3 O3 C6 62.4(3) . . . . ?
C9 C4 C5 C6 168.5(2) . . . . ?
C9 C4 O2 C3 -169.4(2) . . . . ?
C9 C4 P1 C1 -176.2(2) . . . . ?
C9 C4 P1 C11 77.1(2) . . . . ?
C9 C4 P1 Pt1 -47.0(2) . . . . ?
C10 C6 O1 C1 169.9(2) . . . . ?
C10 C6 O3 C3 -175.8(2) . . . . ?
C7 C1 C2 C3 169.8(2) . . . . ?
C7 C1 O1 C6 -170.1(2) . . . . ?
C7 C1 P1 C4 -175.7(2) . . . . ?
C7 C1 P1 C11 -62.3(2) . . . . ?
C7 C1 P1 Pt1 60.8(2) . . . . ?
C8 C3 O2 C4 167.3(2) . . . . ?
C8 C3 O3 C6 -173.8(2) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C11 N1 C15 -1.1(4) . . . . ?
C12 C11 P1 C4 -176.9(2) . . . . ?
C12 C11 P1 C1 83.0(2) . . . . ?
C12 C11 P1 Pt1 -48.9(2) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 177.9(3) . . . . ?
C13 C14 C15 N1 0.4(5) . . . . ?
C14 C15 N1 C11 0.2(4) . . . . ?
C16 C15 N1 C11 -177.4(3) . . . . ?
N1 C11 C12 C13 1.4(5) . . . . ?
N1 C11 P1 C4 1.7(3) . . . . ?
N1 C11 P1 C1 -98.4(2) . . . . ?
N1 C11 P1 Pt1 129.7(2) . . . . ?
O2 C4 C5 C6 51.1(3) . . . . ?
O2 C4 P1 C1 -60.20(17) . . . . ?
O2 C4 P1 C11 -166.92(16) . . . . ?
O2 C4 P1 Pt1 68.91(17) . . . . ?
O2 C3 O3 C6 -59.1(3) . . . . ?
O1 C6 O3 C3 -59.7(3) . . . . ?
O1 C1 C2 C3 51.8(3) . . . . ?
O1 C1 P1 C4 -56.85(18) . . . . ?
O1 C1 P1 C11 56.52(19) . . . . ?
O1 C1 P1 Pt1 179.63(12) . . . . ?
O3 C6 O1 C1 53.9(3) . . . . ?
O3 C3 O2 C4 52.6(3) . . . . ?
P1 C4 C5 C6 -64.4(2) . . . . ?
P1 C4 O2 C3 70.2(2) . . . . ?
P1 C1 C2 C3 -65.6(2) . . . . ?
P1 C1 O1 C6 67.7(2) . . . . ?
P1 C11 C12 C13 179.9(3) . . . . ?
P1 C11 N1 C15 -179.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_meso_1e
_database_code_depnum_ccdc_archive 'CCDC 1497888'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H38 Cl2 F6 N2 O6 P2 Pt'
_chemical_formula_sum            'C32 H38 Cl2 F6 N2 O6 P2 Pt'
_chemical_formula_weight         988.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Pt Pt -1.7033 8.3905 '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                   8.2583(2)
_cell_length_b                   10.6521(3)
_cell_length_c                   11.5490(3)
_cell_angle_alpha                116.7870(10)
_cell_angle_beta                 93.6870(10)
_cell_angle_gamma                98.8740(10)
_cell_volume                     885.69(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9725
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.280
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0468 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16102
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.954
_diffrn_reflns_theta_min         1.998
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4234
_reflns_number_total             4241
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0185
_refine_ls_restrained_S_all      1.074
_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)+(0.0234P)²+0.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0445
_refine_ls_wR_factor_ref         0.0446
_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:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Pt1 Pt 0.0000 0.5000 0.5000 0.01025(4) Uani 1 2 d S T P . .
Cl1 Cl -0.18151(7) 0.32495(6) 0.51880(5) 0.01712(11) Uani 1 1 d . . . . .
P1 P 0.14509(7) 0.53747(6) 0.69571(5) 0.01091(11) Uani 1 1 d . . . . .
F1 F 0.4652(2) 0.0822(2) 0.4077(2) 0.0489(5) Uani 1 1 d . . . . .
F2 F 0.2341(3) 0.0575(2) 0.29960(17) 0.0481(5) Uani 1 1 d . . . . .
F3 F 0.2659(3) -0.09405(17) 0.36755(19) 0.0434(5) Uani 1 1 d . . . . .
O1 O 0.4196(2) 0.64461(17) 0.87865(15) 0.0156(3) Uani 1 1 d . . . . .
O2 O 0.0753(2) 0.77773(17) 0.88119(16) 0.0158(3) Uani 1 1 d . . . . .
O3 O 0.3282(2) 0.85048(17) 1.02395(15) 0.0158(3) Uani 1 1 d . . . . .
N1 N 0.1222(3) 0.3087(2) 0.75052(19) 0.0162(4) Uani 1 1 d . . . . .
C1 C 0.3574(3) 0.6552(2) 0.7644(2) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.3351(3) 0.7055(2) 0.9910(2) 0.0148(4) Uani 1 1 d . . . . .
C3 C 0.1594(3) 0.6219(2) 0.9629(2) 0.0130(4) Uani 1 1 d . . . . .
H3A H 0.1071 0.6618 1.0432 0.016 Uiso 1 1 calc R . . . .
H3B H 0.1612 0.5204 0.9385 0.016 Uiso 1 1 calc R . . . .
C4 C 0.0576(3) 0.6286(2) 0.8529(2) 0.0136(4) Uani 1 1 d . . . . .
C5 C 0.3383(3) 0.8084(2) 0.8041(2) 0.0138(4) Uani 1 1 d . . . . .
H5A H 0.4492 0.8721 0.8290 0.017 Uiso 1 1 calc R . . . .
H5B H 0.2791 0.8120 0.7286 0.017 Uiso 1 1 calc R . . . .
C6 C 0.2421(3) 0.8610(2) 0.9187(2) 0.0155(4) Uani 1 1 d . . . . .
C7 C 0.4825(3) 0.6105(3) 0.6707(2) 0.0166(5) Uani 1 1 d . . . . .
H7A H 0.4989 0.5148 0.6535 0.025 Uiso 1 1 calc GR . . . .
H7B H 0.5883 0.6797 0.7100 0.025 Uiso 1 1 calc GR . . . .
H7C H 0.4414 0.6082 0.5881 0.025 Uiso 1 1 calc GR . . . .
C8 C 0.4412(3) 0.7073(3) 1.1030(2) 0.0220(5) Uani 1 1 d . . . . .
H8A H 0.5525 0.7641 1.1163 0.033 Uiso 1 1 calc GR . . . .
H8B H 0.4489 0.6087 1.0824 0.033 Uiso 1 1 calc GR . . . .
H8C H 0.3914 0.7502 1.1831 0.033 Uiso 1 1 calc GR . . . .
C9 C -0.1251(3) 0.5721(3) 0.8396(2) 0.0186(5) Uani 1 1 d . . . . .
H9A H -0.1852 0.5815 0.7689 0.028 Uiso 1 1 calc GR . . . .
H9B H -0.1650 0.6273 0.9223 0.028 Uiso 1 1 calc GR . . . .
H9C H -0.1439 0.4706 0.8190 0.028 Uiso 1 1 calc GR . . . .
C10 C 0.2254(3) 1.0156(3) 0.9695(3) 0.0217(5) Uani 1 1 d . . . . .
H10A H 0.1541 1.0242 0.9033 0.033 Uiso 1 1 calc GR . . . .
H10B H 0.3352 1.0767 0.9876 0.033 Uiso 1 1 calc GR . . . .
H10C H 0.1761 1.0461 1.0503 0.033 Uiso 1 1 calc GR . . . .
C11 C 0.1719(3) 0.3582(2) 0.6685(2) 0.0138(4) Uani 1 1 d . . . . .
C12 C 0.2321(3) 0.2752(2) 0.5540(2) 0.0160(4) Uani 1 1 d . . . . .
H12 H 0.2660 0.3135 0.4974 0.019 Uiso 1 1 calc R . . . .
C13 C 0.2416(3) 0.1358(2) 0.5248(2) 0.0179(5) Uani 1 1 d . . . . .
C14 C 0.1905(3) 0.0822(3) 0.6085(2) 0.0190(5) Uani 1 1 d . . . . .
H14 H 0.1955 -0.0132 0.5906 0.023 Uiso 1 1 calc R . . . .
C15 C 0.1315(3) 0.1733(3) 0.7198(2) 0.0204(5) Uani 1 1 d . . . . .
H15 H 0.0957 0.1372 0.7776 0.025 Uiso 1 1 calc R . . . .
C16 C 0.3025(3) 0.0446(3) 0.4004(3) 0.0258(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pt1 Cl1 2.3056(5) 2_566 ?
Pt1 Cl1 2.3056(5) . ?
Pt1 P1 2.3227(5) . ?
Pt1 P1 2.3227(5) 2_566 ?
P1 C1 1.877(2) . ?
P1 C4 1.886(2) . ?
P1 C11 1.842(2) . ?
F1 C16 1.328(3) . ?
F2 C16 1.333(4) . ?
F3 C16 1.327(3) . ?
O1 C1 1.442(3) . ?
O1 C2 1.445(3) . ?
O2 C4 1.451(3) . ?
O2 C6 1.439(3) . ?
O3 C2 1.426(3) . ?
O3 C6 1.425(3) . ?
N1 C11 1.333(3) . ?
N1 C15 1.337(3) . ?
C1 C5 1.521(3) . ?
C1 C7 1.516(3) . ?
C2 C3 1.511(3) . ?
C2 C8 1.506(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.513(3) . ?
C4 C9 1.506(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.517(3) . ?
C6 C10 1.512(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.394(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 C14 1.383(3) . ?
C13 C16 1.499(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Pt1 Cl1 180.0 2_566 . ?
Cl1 Pt1 P1 94.810(19) . 2_566 ?
Cl1 Pt1 P1 85.190(19) 2_566 2_566 ?
Cl1 Pt1 P1 85.190(19) . . ?
Cl1 Pt1 P1 94.809(19) 2_566 . ?
P1 Pt1 P1 180.0 2_566 . ?
C1 P1 Pt1 122.16(7) . . ?
C1 P1 C4 94.43(10) . . ?
C4 P1 Pt1 119.23(7) . . ?
C11 P1 Pt1 105.26(7) . . ?
C11 P1 C1 105.04(10) . . ?
C11 P1 C4 109.69(10) . . ?
C1 O1 C2 115.97(16) . . ?
C6 O2 C4 116.15(17) . . ?
C6 O3 C2 111.97(16) . . ?
C11 N1 C15 117.6(2) . . ?
O1 C1 P1 108.48(15) . . ?
O1 C1 C5 109.77(17) . . ?
O1 C1 C7 106.26(17) . . ?
C5 C1 P1 107.01(15) . . ?
C7 C1 P1 113.55(16) . . ?
C7 C1 C5 111.72(19) . . ?
O1 C2 C3 111.10(18) . . ?
O1 C2 C8 105.71(18) . . ?
O3 C2 O1 110.30(18) . . ?
O3 C2 C3 107.96(18) . . ?
O3 C2 C8 107.81(18) . . ?
C8 C2 C3 113.9(2) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.42(18) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
O2 C4 P1 105.69(14) . . ?
O2 C4 C3 108.79(18) . . ?
O2 C4 C9 106.28(18) . . ?
C3 C4 P1 109.63(15) . . ?
C9 C4 P1 113.12(16) . . ?
C9 C4 C3 112.94(19) . . ?
C1 C5 H5A 109.6 . . ?
C1 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C1 110.46(18) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
O2 C6 C5 110.60(18) . . ?
O2 C6 C10 105.71(18) . . ?
O3 C6 O2 111.19(18) . . ?
O3 C6 C5 108.02(18) . . ?
O3 C6 C10 107.30(18) . . ?
C10 C6 C5 114.0(2) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 120.19(17) . . ?
N1 C11 C12 122.8(2) . . ?
C12 C11 P1 116.78(17) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.5(2) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 C16 118.9(2) . . ?
C14 C13 C16 121.5(2) . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.5(2) . . ?
C15 C14 H14 121.3 . . ?
N1 C15 C14 124.0(2) . . ?
N1 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
F1 C16 F2 106.0(2) . . ?
F1 C16 C13 112.3(2) . . ?
F2 C16 C13 111.3(2) . . ?
F3 C16 F1 108.0(2) . . ?
F3 C16 F2 106.4(2) . . ?
F3 C16 C13 112.4(2) . . ?

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
Pt1 P1 C1 O1 -174.32(10) . . . . ?
Pt1 P1 C1 C5 67.31(16) . . . . ?
Pt1 P1 C1 C7 -56.44(18) . . . . ?
Pt1 P1 C4 O2 -70.98(15) . . . . ?
Pt1 P1 C4 C3 171.93(12) . . . . ?
Pt1 P1 C4 C9 44.90(18) . . . . ?
Pt1 P1 C11 N1 -125.64(17) . . . . ?
Pt1 P1 C11 C12 49.06(19) . . . . ?
P1 C1 C5 C6 67.3(2) . . . . ?
P1 C11 C12 C13 -174.94(18) . . . . ?
O1 C1 C5 C6 -50.3(2) . . . . ?
O1 C2 C3 C4 -62.8(2) . . . . ?
O3 C2 C3 C4 58.2(2) . . . . ?
N1 C11 C12 C13 -0.4(4) . . . . ?
C1 P1 C4 O2 59.94(15) . . . . ?
C1 P1 C4 C3 -57.15(17) . . . . ?
C1 P1 C4 C9 175.82(17) . . . . ?
C1 P1 C11 N1 104.23(19) . . . . ?
C1 P1 C11 C12 -81.08(19) . . . . ?
C1 O1 C2 O3 -53.0(2) . . . . ?
C1 O1 C2 C3 66.6(2) . . . . ?
C1 O1 C2 C8 -169.31(19) . . . . ?
C1 C5 C6 O2 -64.3(2) . . . . ?
C1 C5 C6 O3 57.6(2) . . . . ?
C1 C5 C6 C10 176.78(19) . . . . ?
C2 O1 C1 P1 -67.8(2) . . . . ?
C2 O1 C1 C5 48.8(2) . . . . ?
C2 O1 C1 C7 169.77(18) . . . . ?
C2 O3 C6 O2 58.5(2) . . . . ?
C2 O3 C6 C5 -63.0(2) . . . . ?
C2 O3 C6 C10 173.66(19) . . . . ?
C2 C3 C4 P1 64.2(2) . . . . ?
C2 C3 C4 O2 -50.9(2) . . . . ?
C2 C3 C4 C9 -168.69(19) . . . . ?
C4 P1 C1 O1 56.83(15) . . . . ?
C4 P1 C1 C5 -61.53(15) . . . . ?
C4 P1 C1 C7 174.72(16) . . . . ?
C4 P1 C11 N1 3.8(2) . . . . ?
C4 P1 C11 C12 178.50(17) . . . . ?
C4 O2 C6 O3 -52.4(2) . . . . ?
C4 O2 C6 C5 67.7(2) . . . . ?
C4 O2 C6 C10 -168.48(18) . . . . ?
C6 O2 C4 P1 -69.13(19) . . . . ?
C6 O2 C4 C3 48.5(2) . . . . ?
C6 O2 C4 C9 170.41(18) . . . . ?
C6 O3 C2 O1 59.9(2) . . . . ?
C6 O3 C2 C3 -61.6(2) . . . . ?
C6 O3 C2 C8 174.86(19) . . . . ?
C7 C1 C5 C6 -167.86(19) . . . . ?
C8 C2 C3 C4 177.94(18) . . . . ?
C11 P1 C1 O1 -54.92(16) . . . . ?
C11 P1 C1 C5 -173.29(14) . . . . ?
C11 P1 C1 C7 62.96(18) . . . . ?
C11 P1 C4 O2 167.64(13) . . . . ?
C11 P1 C4 C3 50.55(18) . . . . ?
C11 P1 C4 C9 -76.47(18) . . . . ?
C11 N1 C15 C14 0.3(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C11 C12 C13 C16 178.6(2) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C12 C13 C16 F1 74.2(3) . . . . ?
C12 C13 C16 F2 -44.4(3) . . . . ?
C12 C13 C16 F3 -163.7(2) . . . . ?
C13 C14 C15 N1 -0.3(4) . . . . ?
C14 C13 C16 F1 -107.7(3) . . . . ?
C14 C13 C16 F2 133.7(3) . . . . ?
C14 C13 C16 F3 14.4(4) . . . . ?
C15 N1 C11 P1 174.37(18) . . . . ?
C15 N1 C11 C12 0.0(3) . . . . ?
C16 C13 C14 C15 -178.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_meso_1g
_database_code_depnum_ccdc_archive 'CCDC 1497889'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H56 Cl2 N2 O6 P2 Pt Si2'
_chemical_formula_sum            'C36 H56 Cl2 N2 O6 P2 Pt Si2'
_chemical_formula_weight         996.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   8.8531(2)
_cell_length_b                   10.6257(3)
_cell_length_c                   11.9101(3)
_cell_angle_alpha                79.9244(15)
_cell_angle_beta                 83.9717(15)
_cell_angle_gamma                88.2507(15)
_cell_volume                     1096.92(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.490
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0518 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.8133.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.970
_diffrn_reflns_theta_min         1.947
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5263
_reflns_number_total             5264
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.360
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.074
_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)+(0.0263P)²+0.6616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0447
_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
 O1-C1 \\sim O1-C2 \\sim O1A-C1 \\sim O1A-C6 \\sim O3A-C4 \\sim O3A-C2 \\sim
O3-C4 \\sim O3-C6
 with sigma of 0.01
 C5A-C1 \\sim C5A-C2 \\sim C5-C1 \\sim C6-C5 \\sim C3-C4 \\sim C2-C3 \\sim
C3A-C4 \\sim C6-C3A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C3A) = Uanis(O3)
Uanis(C3) = Uanis(O3A)
Uanis(C5) = Uanis(O1A)
Uanis(C5A) = Uanis(O1)
4. Others
 Fixed Sof: O3A(0.36543) O1A(0.36543) C3A(0.36543) H3AA(0.36543) H3AB(0.36543)
 C5A(0.36543) H5AA(0.36543) H5AB(0.36543) C5(0.63457) H5A(0.63457) H5B(0.63457)
 O1(0.63457) O3(0.63457) C3(0.63457) H3A(0.63457) H3B(0.63457)
5.a Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C5A(H5AA,H5AB), C5(H5A,H5B), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pt1 Pt 0.5000 0.0000 0.0000 0.01294(4) Uani 1 2 d S T P . .
Cl1 Cl 0.66499(6) 0.16823(5) -0.02483(5) 0.02990(12) Uani 1 1 d . . . . .
P1 P 0.37681(5) 0.09183(4) 0.14794(4) 0.01354(9) Uani 1 1 d . . . . .
Si1 Si 0.18395(7) 0.45820(6) -0.20585(5) 0.02535(12) Uani 1 1 d . . . . .
O2 O 0.23938(19) -0.03662(16) 0.45461(13) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.37223(19) 0.35077(17) 0.15598(16) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.4715(2) 0.0669(2) 0.28383(17) 0.0220(4) Uani 1 1 d D . . . .
C2 C 0.2333(2) 0.0958(2) 0.40473(17) 0.0256(4) Uani 1 1 d D . . . .
C1 C 0.1868(2) 0.03515(17) 0.22126(15) 0.0151(3) Uani 1 1 d D . . . .
C6 C 0.3030(2) -0.1122(2) 0.37331(18) 0.0253(4) Uani 1 1 d D . . . .
C9 C 0.6381(3) 0.1011(3) 0.2644(2) 0.0412(7) Uani 1 1 d . . . . .
H9A H 0.6913 0.0494 0.2118 0.062 Uiso 1 1 calc GR . . . .
H9B H 0.6823 0.0841 0.3378 0.062 Uiso 1 1 calc GR . . . .
H9C H 0.6485 0.1919 0.2313 0.062 Uiso 1 1 calc GR . . . .
C8 C 0.1530(4) 0.1670(3) 0.4933(3) 0.0541(9) Uani 1 1 d . . . . .
H8A H 0.1473 0.2582 0.4611 0.081 Uiso 1 1 calc GR . . . .
H8B H 0.2094 0.1552 0.5610 0.081 Uiso 1 1 calc GR . . . .
H8C H 0.0501 0.1337 0.5154 0.081 Uiso 1 1 calc GR . . . .
C7 C 0.0649(2) 0.0465(2) 0.13996(18) 0.0234(4) Uani 1 1 d . . . . .
H7A H 0.0511 0.1365 0.1061 0.035 Uiso 1 1 calc GR . . . .
H7B H -0.0308 0.0134 0.1821 0.035 Uiso 1 1 calc GR . . . .
H7C H 0.0954 -0.0030 0.0790 0.035 Uiso 1 1 calc GR . . . .
C10 C 0.3078(4) -0.2482(3) 0.4359(3) 0.0524(9) Uani 1 1 d . . . . .
H10A H 0.3424 -0.3049 0.3815 0.079 Uiso 1 1 calc GR . . . .
H10B H 0.2059 -0.2731 0.4719 0.079 Uiso 1 1 calc GR . . . .
H10C H 0.3781 -0.2550 0.4951 0.079 Uiso 1 1 calc GR . . . .
C11 C 0.3437(2) 0.26182(18) 0.09418(17) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.2880(2) 0.29043(19) -0.01285(17) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.2728 0.2236 -0.0539 0.023 Uiso 1 1 calc R . . . .
C13 C 0.2546(2) 0.41662(19) -0.05985(18) 0.0205(4) Uani 1 1 d . . . . .
C14 C 0.2833(2) 0.5086(2) 0.0056(2) 0.0256(4) Uani 1 1 d . . . . .
H14 H 0.2625 0.5962 -0.0214 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3423(2) 0.4719(2) 0.1100(2) 0.0259(4) Uani 1 1 d . . . . .
H15 H 0.3628 0.5370 0.1515 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0750(3) 0.6110(2) -0.2159(3) 0.0386(6) Uani 1 1 d . . . . .
H16A H 0.1401 0.6785 -0.2022 0.058 Uiso 1 1 calc GR . . . .
H16B H -0.0133 0.6012 -0.1584 0.058 Uiso 1 1 calc GR . . . .
H16C H 0.0408 0.6338 -0.2926 0.058 Uiso 1 1 calc GR . . . .
C17 C 0.0598(4) 0.3264(3) -0.2250(3) 0.0438(7) Uani 1 1 d . . . . .
H17A H -0.0224 0.3137 -0.1624 0.066 Uiso 1 1 calc GR . . . .
H17B H 0.1201 0.2474 -0.2242 0.066 Uiso 1 1 calc GR . . . .
H17C H 0.0165 0.3489 -0.2984 0.066 Uiso 1 1 calc GR . . . .
C18 C 0.3533(3) 0.4725(3) -0.3133(2) 0.0433(6) Uani 1 1 d . . . . .
H18A H 0.3206 0.4910 -0.3907 0.065 Uiso 1 1 calc GR . . . .
H18B H 0.4115 0.3920 -0.3041 0.065 Uiso 1 1 calc GR . . . .
H18C H 0.4173 0.5420 -0.3019 0.065 Uiso 1 1 calc GR . . . .
O3A O 0.3897(12) 0.1347(18) 0.3682(17) 0.0269(6) Uani 0.3654 1 d D . . A 2
O1A O 0.207(2) -0.0962(9) 0.2794(13) 0.0179(4) Uani 0.3654 1 d D . . A 2
C3A C 0.4606(16) -0.0765(10) 0.318(2) 0.0237(12) Uani 0.3654 1 d D . . A 2
H3AA H 0.4839 -0.1175 0.2500 0.028 Uiso 0.3654 1 calc R . . A 2
H3AB H 0.5358 -0.1076 0.3731 0.028 Uiso 0.3654 1 calc R . . A 2
C5A C 0.130(3) 0.114(3) 0.3109(15) 0.0173(8) Uani 0.3654 1 d D . . A 2
H5AA H 0.1265 0.2051 0.2755 0.021 Uiso 0.3654 1 calc R . . A 2
H5AB H 0.0261 0.0872 0.3432 0.021 Uiso 0.3654 1 calc R . . A 2
C5 C 0.2022(17) -0.1027(8) 0.2780(11) 0.0179(4) Uani 0.6346 1 d D . . A 1
H5A H 0.1008 -0.1370 0.3092 0.022 Uiso 0.6346 1 calc R . . A 1
H5B H 0.2463 -0.1543 0.2207 0.022 Uiso 0.6346 1 calc R . . A 1
O1 O 0.1454(9) 0.1150(10) 0.3068(6) 0.0173(8) Uani 0.6346 1 d D . . A 1
O3 O 0.4563(6) -0.0678(4) 0.3351(7) 0.0237(12) Uani 0.6346 1 d D . . A 1
C3 C 0.3927(10) 0.1428(16) 0.3690(14) 0.0269(6) Uani 0.6346 1 d D . . A 1
H3A H 0.4498 0.1340 0.4371 0.032 Uiso 0.6346 1 calc R . . A 1
H3B H 0.3899 0.2344 0.3341 0.032 Uiso 0.6346 1 calc R . . A 1


_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
Pt1 Cl1 2.3022(5) . ?
Pt1 Cl1 2.3022(5) 2_655 ?
Pt1 P1 2.3194(5) 2_655 ?
Pt1 P1 2.3193(5) . ?
P1 C4 1.875(2) . ?
P1 C1 1.8770(18) . ?
P1 C11 1.833(2) . ?
Si1 C13 1.885(2) . ?
Si1 C16 1.855(3) . ?
Si1 C17 1.865(3) . ?
Si1 C18 1.858(3) . ?
O2 C2 1.431(3) . ?
O2 C6 1.425(3) . ?
N1 C11 1.340(2) . ?
N1 C15 1.337(3) . ?
C4 C9 1.514(3) . ?
C4 O3A 1.457(8) . ?
C4 C3A 1.510(9) . ?
C4 O3 1.458(5) . ?
C4 C3 1.507(7) . ?
C2 C8 1.509(3) . ?
C2 O3A 1.457(8) . ?
C2 C5A 1.499(9) . ?
C2 O1 1.451(5) . ?
C2 C3 1.505(7) . ?
C1 C7 1.513(3) . ?
C1 O1A 1.460(7) . ?
C1 C5A 1.503(9) . ?
C1 C5 1.511(7) . ?
C1 O1 1.448(4) . ?
C6 C10 1.507(3) . ?
C6 O1A 1.457(7) . ?
C6 C3A 1.507(9) . ?
C6 C5 1.504(7) . ?
C6 O3 1.451(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.396(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(3) . ?
C13 C14 1.396(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Pt1 Cl1 180.0 . 2_655 ?
Cl1 Pt1 P1 85.500(17) . . ?
Cl1 Pt1 P1 94.500(17) 2_655 . ?
Cl1 Pt1 P1 85.499(17) 2_655 2_655 ?
Cl1 Pt1 P1 94.500(17) . 2_655 ?
P1 Pt1 P1 180.0 . 2_655 ?
C4 P1 Pt1 115.57(6) . . ?
C4 P1 C1 94.23(9) . . ?
C1 P1 Pt1 122.00(6) . . ?
C11 P1 Pt1 108.53(6) . . ?
C11 P1 C4 111.82(9) . . ?
C11 P1 C1 103.66(8) . . ?
C16 Si1 C13 109.49(12) . . ?
C16 Si1 C17 110.24(13) . . ?
C16 Si1 C18 110.94(13) . . ?
C17 Si1 C13 108.26(11) . . ?
C18 Si1 C13 107.22(11) . . ?
C18 Si1 C17 110.59(15) . . ?
C6 O2 C2 111.44(16) . . ?
C15 N1 C11 116.11(18) . . ?
C9 C4 P1 112.98(15) . . ?
O3A C4 P1 110.9(9) . . ?
O3A C4 C9 111.4(4) . . ?
O3A C4 C3A 112.4(11) . . ?
C3A C4 P1 100.6(11) . . ?
C3A C4 C9 108.0(6) . . ?
O3 C4 P1 107.4(4) . . ?
O3 C4 C9 109.3(3) . . ?
O3 C4 C3 107.0(7) . . ?
C3 C4 P1 111.2(7) . . ?
C3 C4 C9 108.8(4) . . ?
O2 C2 C8 107.89(19) . . ?
O2 C2 O3A 106.4(9) . . ?
O2 C2 C5A 109.3(11) . . ?
O2 C2 O1 110.7(5) . . ?
O2 C2 C3 108.9(7) . . ?
O3A C2 C8 114.3(4) . . ?
O3A C2 C5A 114.9(15) . . ?
C5A C2 C8 103.9(5) . . ?
O1 C2 C8 107.6(3) . . ?
O1 C2 C3 110.3(9) . . ?
C3 C2 C8 111.4(4) . . ?
C7 C1 P1 112.87(13) . . ?
O1A C1 P1 107.4(8) . . ?
O1A C1 C7 112.2(4) . . ?
O1A C1 C5A 107.6(13) . . ?
C5A C1 P1 111.2(12) . . ?
C5A C1 C7 105.6(5) . . ?
C5 C1 P1 108.8(7) . . ?
C5 C1 C7 109.4(4) . . ?
O1 C1 P1 106.4(5) . . ?
O1 C1 C7 109.1(3) . . ?
O1 C1 C5 110.2(7) . . ?
O2 C6 C10 106.68(19) . . ?
O2 C6 O1A 108.0(8) . . ?
O2 C6 C3A 115.8(9) . . ?
O2 C6 C5 109.2(6) . . ?
O2 C6 O3 107.5(3) . . ?
C10 C6 C3A 108.4(6) . . ?
O1A C6 C10 112.6(4) . . ?
O1A C6 C3A 105.6(13) . . ?
C5 C6 C10 109.7(4) . . ?
O3 C6 C10 109.8(3) . . ?
O3 C6 C5 113.7(7) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 120.72(15) . . ?
N1 C11 C12 123.44(18) . . ?
C12 C11 P1 115.84(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.35(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 Si1 121.16(15) . . ?
C12 C13 C14 115.81(19) . . ?
C14 C13 Si1 122.97(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.00(19) . . ?
C15 C14 H14 120.0 . . ?
N1 C15 C14 124.26(19) . . ?
N1 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 O3A C4 115.8(8) . . ?
C6 O1A C1 115.5(8) . . ?
C4 C3A H3AA 109.6 . . ?
C4 C3A H3AB 109.6 . . ?
C6 C3A C4 110.1(9) . . ?
C6 C3A H3AA 109.6 . . ?
C6 C3A H3AB 109.6 . . ?
H3AA C3A H3AB 108.2 . . ?
C2 C5A C1 110.1(9) . . ?
C2 C5A H5AA 109.6 . . ?
C2 C5A H5AB 109.6 . . ?
C1 C5A H5AA 109.6 . . ?
C1 C5A H5AB 109.6 . . ?
H5AA C5A H5AB 108.1 . . ?
C1 C5 H5A 109.7 . . ?
C1 C5 H5B 109.7 . . ?
C6 C5 C1 109.9(6) . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C1 O1 C2 116.2(4) . . ?
C6 O3 C4 116.3(4) . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 C4 110.1(6) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?

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
Pt1 P1 C4 C9 50.67(19) . . . . ?
Pt1 P1 C4 O3A 176.6(6) . . . . ?
Pt1 P1 C4 C3A -64.3(5) . . . . ?
Pt1 P1 C4 O3 -70.0(2) . . . . ?
Pt1 P1 C4 C3 173.3(5) . . . . ?
Pt1 P1 C1 C7 -59.61(15) . . . . ?
Pt1 P1 C1 O1A 64.5(5) . . . . ?
Pt1 P1 C1 C5A -178.0(7) . . . . ?
Pt1 P1 C1 C5 62.0(4) . . . . ?
Pt1 P1 C1 O1 -179.3(3) . . . . ?
Pt1 P1 C11 N1 -135.12(14) . . . . ?
Pt1 P1 C11 C12 44.98(16) . . . . ?
P1 C4 O3A C2 61.2(18) . . . . ?
P1 C4 C3A C6 -78.8(16) . . . . ?
P1 C4 O3 C6 -65.0(6) . . . . ?
P1 C4 C3 C2 64.1(13) . . . . ?
P1 C1 O1A C6 65.7(15) . . . . ?
P1 C1 C5A C2 -64(2) . . . . ?
P1 C1 C5 C6 66.0(11) . . . . ?
P1 C1 O1 C2 -70.1(9) . . . . ?
P1 C11 C12 C13 178.03(15) . . . . ?
Si1 C13 C14 C15 -176.84(17) . . . . ?
O2 C2 O3A C4 60.3(17) . . . . ?
O2 C2 C5A C1 -59(2) . . . . ?
O2 C2 O1 C1 -50.9(9) . . . . ?
O2 C2 C3 C4 59.1(13) . . . . ?
O2 C6 O1A C1 57.4(15) . . . . ?
O2 C6 C3A C4 -44.4(19) . . . . ?
O2 C6 C5 C1 58.8(11) . . . . ?
O2 C6 O3 C4 -57.9(6) . . . . ?
N1 C11 C12 C13 -1.9(3) . . . . ?
C4 P1 C1 C7 176.58(15) . . . . ?
C4 P1 C1 O1A -59.3(5) . . . . ?
C4 P1 C1 C5A 58.2(7) . . . . ?
C4 P1 C1 C5 -61.8(4) . . . . ?
C4 P1 C1 O1 56.9(3) . . . . ?
C4 P1 C11 N1 -6.47(19) . . . . ?
C4 P1 C11 C12 173.62(14) . . . . ?
C2 O2 C6 C10 178.4(2) . . . . ?
C2 O2 C6 O1A -60.3(6) . . . . ?
C2 O2 C6 C3A 57.7(10) . . . . ?
C2 O2 C6 C5 -63.1(5) . . . . ?
C2 O2 C6 O3 60.7(4) . . . . ?
C1 P1 C4 C9 179.31(18) . . . . ?
C1 P1 C4 O3A -54.7(7) . . . . ?
C1 P1 C4 C3A 64.4(5) . . . . ?
C1 P1 C4 O3 58.7(2) . . . . ?
C1 P1 C4 C3 -58.0(5) . . . . ?
C1 P1 C11 N1 93.84(16) . . . . ?
C1 P1 C11 C12 -86.07(16) . . . . ?
C6 O2 C2 C8 175.4(2) . . . . ?
C6 O2 C2 O3A -61.6(7) . . . . ?
C6 O2 C2 C5A 63.0(9) . . . . ?
C6 O2 C2 O1 57.9(4) . . . . ?
C6 O2 C2 C3 -63.6(5) . . . . ?
C9 C4 O3A C2 -172.0(12) . . . . ?
C9 C4 C3A C6 162.6(12) . . . . ?
C9 C4 O3 C6 172.1(5) . . . . ?
C9 C4 C3 C2 -170.8(9) . . . . ?
C8 C2 O3A C4 179.2(12) . . . . ?
C8 C2 C5A C1 -173.7(15) . . . . ?
C8 C2 O1 C1 -168.6(7) . . . . ?
C8 C2 C3 C4 178.0(9) . . . . ?
C7 C1 O1A C6 -169.8(10) . . . . ?
C7 C1 C5A C2 172.8(15) . . . . ?
C7 C1 C5 C6 -170.3(8) . . . . ?
C7 C1 O1 C2 167.9(7) . . . . ?
C10 C6 O1A C1 174.9(10) . . . . ?
C10 C6 C3A C4 -164.1(12) . . . . ?
C10 C6 C5 C1 175.4(8) . . . . ?
C10 C6 O3 C4 -173.6(5) . . . . ?
C11 P1 C4 C9 -74.15(19) . . . . ?
C11 P1 C4 O3A 51.8(7) . . . . ?
C11 P1 C4 C3A 170.9(5) . . . . ?
C11 P1 C4 O3 165.2(2) . . . . ?
C11 P1 C4 C3 48.5(5) . . . . ?
C11 P1 C1 C7 62.91(15) . . . . ?
C11 P1 C1 O1A -173.0(5) . . . . ?
C11 P1 C1 C5A -55.5(7) . . . . ?
C11 P1 C1 C5 -175.5(4) . . . . ?
C11 P1 C1 O1 -56.8(3) . . . . ?
C11 N1 C15 C14 0.9(3) . . . . ?
C11 C12 C13 Si1 178.45(15) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 N1 -1.5(3) . . . . ?
C15 N1 C11 P1 -179.08(15) . . . . ?
C15 N1 C11 C12 0.8(3) . . . . ?
C16 Si1 C13 C12 155.62(17) . . . . ?
C16 Si1 C13 C14 -27.3(2) . . . . ?
C17 Si1 C13 C12 35.4(2) . . . . ?
C17 Si1 C13 C14 -147.5(2) . . . . ?
C18 Si1 C13 C12 -83.9(2) . . . . ?
C18 Si1 C13 C14 93.1(2) . . . . ?
O3A C4 C3A C6 39(2) . . . . ?
O3A C4 O3 C6 52.8(10) . . . . ?
O3A C4 C3 C2 -22(30) . . . . ?
O3A C2 C5A C1 61(2) . . . . ?
O3A C2 O1 C1 66.4(11) . . . . ?
O3A C2 C3 C4 21(30) . . . . ?
O1A C1 C5A C2 53(2) . . . . ?
O1A C1 C5 C6 7(31) . . . . ?
O1A C1 O1 C2 45.3(12) . . . . ?
O1A C6 C3A C4 75.0(17) . . . . ?
O1A C6 C5 C1 -6(30) . . . . ?
O1A C6 O3 C4 60.5(9) . . . . ?
C3A C4 O3A C2 -51(2) . . . . ?
C3A C4 O3 C6 -105(6) . . . . ?
C3A C4 C3 C2 -49.4(17) . . . . ?
C3A C6 O1A C1 -67.0(16) . . . . ?
C3A C6 C5 C1 -67.2(12) . . . . ?
C3A C6 O3 C4 104(6) . . . . ?
C5A C2 O3A C4 -61(2) . . . . ?
C5A C2 O1 C1 -125(15) . . . . ?
C5A C2 C3 C4 -64.0(16) . . . . ?
C5A C1 O1A C6 -54.1(18) . . . . ?
C5A C1 C5 C6 -55.4(14) . . . . ?
C5A C1 O1 C2 124(15) . . . . ?
C5 C1 O1A C6 -173(34) . . . . ?
C5 C1 C5A C2 55(2) . . . . ?
C5 C1 O1 C2 47.7(11) . . . . ?
C5 C6 O1A C1 173(32) . . . . ?
C5 C6 C3A C4 77.6(17) . . . . ?
C5 C6 O3 C4 63.1(8) . . . . ?
O1 C2 O3A C4 -59.7(18) . . . . ?
O1 C2 C5A C1 49(13) . . . . ?
O1 C2 C3 C4 -62.6(13) . . . . ?
O1 C1 O1A C6 -49.0(16) . . . . ?
O1 C1 C5A C2 -50(13) . . . . ?
O1 C1 C5 C6 -50.3(12) . . . . ?
O3 C4 O3A C2 -54.1(18) . . . . ?
O3 C4 C3A C6 63(5) . . . . ?
O3 C4 C3 C2 -52.8(13) . . . . ?
O3 C6 O1A C1 -60.7(16) . . . . ?
O3 C6 C3A C4 -63(5) . . . . ?
O3 C6 C5 C1 -61.2(12) . . . . ?
C3 C4 O3A C2 157(33) . . . . ?
C3 C4 C3A C6 41(2) . . . . ?
C3 C4 O3 C6 54.4(8) . . . . ?
C3 C2 O3A C4 -157(33) . . . . ?
C3 C2 C5A C1 64(2) . . . . ?
C3 C2 O1 C1 69.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1497890'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_5                   
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: Compound is twinned, Flack not determined
;
# Added during the CSD deposition process: Friday 05 August 2016 03:50 PM
# end Validation Reply Form

_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H40 Cl N2 O6 P2 Pd, B F4, C H2 Cl2'
_chemical_formula_sum            'C31 H42 B Cl3 F4 N2 O6 P2 Pd'
_chemical_formula_weight         900.16
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
Pd Pd -0.9988 1.0072 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   29.1906(14)
_cell_length_b                   9.8378(5)
_cell_length_c                   13.0430(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3745.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7474
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0600 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32854
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.909
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6231
_reflns_number_total             6803
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²+0.9910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.60(3) 0.40(3)
2. 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
3. Restrained distances
 F4A-B1
 1.37 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F1 \\sim F4 \\sim F7 \\sim F1A \\sim F4A \\sim F7A \\sim F2 \\sim F6 \\sim F9:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: F1(0.48269) F4(0.48269) F7(0.48269) F1A(0.34267) F4A(0.34267)
 F7A(0.34267) F2(0.17469) F6(0.17469) F9(0.17469)
6.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C18(H18A,H18B), C20(H20A,H20B), C31(H31A,H31B)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C27(H27), C28(H28), C29(H29), C30(H30)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Pd1 Pd 0.67989(2) 0.09506(2) 0.60803(3) 0.00982(6) Uani 1 1 d . . . . .
Cl1 Cl 0.73932(3) 0.05783(10) 0.72023(8) 0.0187(2) Uani 1 1 d . . . . .
P1 P 0.63017(3) 0.07017(10) 0.47084(7) 0.00976(19) Uani 1 1 d . . . . .
P2 P 0.65955(3) 0.26972(10) 0.71326(8) 0.01042(19) Uani 1 1 d . . . . .
O1 O 0.60169(9) 0.0808(3) 0.27650(19) 0.0120(5) Uani 1 1 d . . . . .
O2 O 0.53901(8) 0.0879(3) 0.49198(19) 0.0126(5) Uani 1 1 d . . . . .
O3 O 0.52315(9) 0.0967(3) 0.3145(2) 0.0161(6) Uani 1 1 d . . . . .
O4 O 0.60714(8) 0.4175(3) 0.58924(18) 0.0124(6) Uani 1 1 d . . . . .
O5 O 0.63398(9) 0.6307(3) 0.64302(19) 0.0142(6) Uani 1 1 d . . . . .
O6 O 0.68266(9) 0.5317(3) 0.7659(2) 0.0135(6) Uani 1 1 d . . . . .
N1 N 0.70166(10) -0.0582(3) 0.5104(3) 0.0129(7) Uani 1 1 d . . . . .
N2 N 0.64075(12) 0.0871(3) 0.8534(3) 0.0178(7) Uani 1 1 d . . . . .
C1 C 0.61482(12) 0.1748(4) 0.3570(3) 0.0120(8) Uani 1 1 d . . . . .
C2 C 0.55984(13) 0.0054(4) 0.2923(3) 0.0141(8) Uani 1 1 d . . . . .
C3 C 0.56443(13) -0.0931(4) 0.3810(3) 0.0133(8) Uani 1 1 d . . . . .
H3A H 0.5902 -0.1561 0.3678 0.016 Uiso 1 1 calc R . . . .
H3B H 0.5361 -0.1477 0.3871 0.016 Uiso 1 1 calc R . . . .
C4 C 0.57288(12) -0.0170(4) 0.4808(3) 0.0129(8) Uani 1 1 d . . . . .
C5 C 0.57394(12) 0.2628(4) 0.3858(3) 0.0123(8) Uani 1 1 d . . . . .
H5A H 0.5674 0.3278 0.3297 0.015 Uiso 1 1 calc R . . . .
H5B H 0.5812 0.3156 0.4484 0.015 Uiso 1 1 calc R . . . .
C6 C 0.53184(13) 0.1744(4) 0.4051(3) 0.0133(8) Uani 1 1 d . . . . .
C7 C 0.65587(13) 0.2529(4) 0.3171(3) 0.0142(8) Uani 1 1 d . . . . .
H7A H 0.6783 0.1890 0.2889 0.021 Uiso 1 1 calc GR . . . .
H7B H 0.6698 0.3042 0.3734 0.021 Uiso 1 1 calc GR . . . .
H7C H 0.6460 0.3159 0.2633 0.021 Uiso 1 1 calc GR . . . .
C8 C 0.54926(14) -0.0620(4) 0.1910(3) 0.0210(9) Uani 1 1 d . . . . .
H8A H 0.5466 0.0075 0.1375 0.032 Uiso 1 1 calc GR . . . .
H8B H 0.5203 -0.1120 0.1965 0.032 Uiso 1 1 calc GR . . . .
H8C H 0.5740 -0.1251 0.1734 0.032 Uiso 1 1 calc GR . . . .
C9 C 0.57048(13) -0.1041(4) 0.5760(3) 0.0165(8) Uani 1 1 d . . . . .
H9A H 0.5766 -0.0478 0.6365 0.025 Uiso 1 1 calc GR . . . .
H9B H 0.5934 -0.1766 0.5717 0.025 Uiso 1 1 calc GR . . . .
H9C H 0.5399 -0.1444 0.5817 0.025 Uiso 1 1 calc GR . . . .
C10 C 0.48909(13) 0.2555(5) 0.4285(3) 0.0205(9) Uani 1 1 d . . . . .
H10A H 0.4940 0.3095 0.4907 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.4633 0.1933 0.4391 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.4823 0.3162 0.3709 0.031 Uiso 1 1 calc GR . . . .
C11 C 0.67309(12) -0.0531(4) 0.4284(3) 0.0112(8) Uani 1 1 d . . . . .
C12 C 0.68112(13) -0.1276(4) 0.3405(3) 0.0139(8) Uani 1 1 d . . . . .
H12 H 0.6614 -0.1208 0.2828 0.017 Uiso 1 1 calc R . . . .
C13 C 0.71905(14) -0.2129(4) 0.3393(3) 0.0179(9) Uani 1 1 d . . . . .
H13 H 0.7257 -0.2653 0.2800 0.021 Uiso 1 1 calc R . . . .
C14 C 0.74703(14) -0.2215(4) 0.4245(3) 0.0181(9) Uani 1 1 d . . . . .
H14 H 0.7723 -0.2823 0.4248 0.022 Uiso 1 1 calc R . . . .
C15 C 0.73811(13) -0.1410(4) 0.5092(3) 0.0162(8) Uani 1 1 d . . . . .
H15 H 0.7579 -0.1445 0.5669 0.019 Uiso 1 1 calc R . . . .
C16 C 0.60498(12) 0.3638(4) 0.6918(3) 0.0106(7) Uani 1 1 d . . . . .
C17 C 0.64083(13) 0.5222(4) 0.5726(3) 0.0143(8) Uani 1 1 d . . . . .
C18 C 0.68959(12) 0.4690(4) 0.5867(3) 0.0142(9) Uani 1 1 d . . . . .
H18A H 0.6948 0.3908 0.5404 0.017 Uiso 1 1 calc R . . . .
H18B H 0.7118 0.5412 0.5686 0.017 Uiso 1 1 calc R . . . .
C19 C 0.69712(12) 0.4250(4) 0.6975(3) 0.0137(8) Uani 1 1 d . . . . .
C20 C 0.60143(13) 0.4821(4) 0.7680(3) 0.0134(8) Uani 1 1 d . . . . .
H20A H 0.5708 0.5245 0.7623 0.016 Uiso 1 1 calc R . . . .
H20B H 0.6050 0.4471 0.8387 0.016 Uiso 1 1 calc R . . . .
C21 C 0.63798(14) 0.5878(4) 0.7470(3) 0.0133(9) Uani 1 1 d . . . . .
C22 C 0.56386(12) 0.2707(4) 0.6964(3) 0.0147(8) Uani 1 1 d . . . . .
H22A H 0.5635 0.2230 0.7624 0.022 Uiso 1 1 calc GR . . . .
H22B H 0.5656 0.2041 0.6407 0.022 Uiso 1 1 calc GR . . . .
H22C H 0.5358 0.3244 0.6892 0.022 Uiso 1 1 calc GR . . . .
C23 C 0.63099(18) 0.5793(4) 0.4680(4) 0.0217(10) Uani 1 1 d . . . . .
H23A H 0.5987 0.6060 0.4639 0.032 Uiso 1 1 calc GR . . . .
H23B H 0.6374 0.5101 0.4159 0.032 Uiso 1 1 calc GR . . . .
H23C H 0.6504 0.6589 0.4560 0.032 Uiso 1 1 calc GR . . . .
C24 C 0.74676(13) 0.3990(4) 0.7240(4) 0.0204(9) Uani 1 1 d . . . . .
H24A H 0.7588 0.3265 0.6801 0.031 Uiso 1 1 calc GR . . . .
H24B H 0.7491 0.3715 0.7960 0.031 Uiso 1 1 calc GR . . . .
H24C H 0.7645 0.4823 0.7131 0.031 Uiso 1 1 calc GR . . . .
C25 C 0.63402(14) 0.7141(4) 0.8117(3) 0.0179(8) Uani 1 1 d . . . . .
H25A H 0.6048 0.7591 0.7975 0.027 Uiso 1 1 calc GR . . . .
H25B H 0.6593 0.7761 0.7954 0.027 Uiso 1 1 calc GR . . . .
H25C H 0.6355 0.6893 0.8844 0.027 Uiso 1 1 calc GR . . . .
C26 C 0.65778(13) 0.2123(4) 0.8457(3) 0.0161(8) Uani 1 1 d . . . . .
C27 C 0.67270(13) 0.2891(5) 0.9292(3) 0.0182(9) Uani 1 1 d . . . . .
H27 H 0.6837 0.3792 0.9205 0.022 Uiso 1 1 calc R . . . .
C28 C 0.67086(14) 0.2291(5) 1.0250(3) 0.0217(9) Uani 1 1 d . . . . .
H28 H 0.6809 0.2777 1.0838 0.026 Uiso 1 1 calc R . . . .
C29 C 0.65441(16) 0.0989(5) 1.0349(3) 0.0231(9) Uani 1 1 d . . . . .
H29 H 0.6534 0.0559 1.1001 0.028 Uiso 1 1 calc R . . . .
C30 C 0.63917(15) 0.0312(4) 0.9474(3) 0.0221(9) Uani 1 1 d . . . . .
H30 H 0.6272 -0.0581 0.9546 0.026 Uiso 1 1 calc R . . . .
F0AA F 0.35537(11) 0.4212(3) 0.7058(2) 0.0437(8) Uani 1 1 d . . . . .
B1 B 0.34953(15) 0.3645(4) 0.6108(5) 0.0219(9) Uani 1 1 d D . . . .
F1 F 0.3360(11) 0.232(3) 0.621(2) 0.036(5) Uani 0.4827 1 d . U P A 1
F4 F 0.3176(7) 0.4412(19) 0.5538(18) 0.055(5) Uani 0.4827 1 d . U P A 1
F7 F 0.3937(5) 0.3615(15) 0.5629(11) 0.043(3) Uani 0.4827 1 d . U P A 1
F1A F 0.3442(14) 0.226(4) 0.608(3) 0.031(6) Uani 0.3427 1 d . U P A 2
F4A F 0.3107(6) 0.413(2) 0.562(2) 0.027(4) Uani 0.3427 1 d D U P A 2
F7A F 0.3849(6) 0.4031(16) 0.5433(14) 0.027(4) Uani 0.3427 1 d . U P A 2
F2 F 0.3025(10) 0.375(3) 0.595(2) 0.043(5) Uani 0.1747 1 d . U P A 3
F6 F 0.3720(12) 0.444(3) 0.536(3) 0.043(6) Uani 0.1747 1 d . U P A 3
F9 F 0.3612(8) 0.231(5) 0.610(4) 0.036(6) Uani 0.1747 1 d . U P A 3
Cl2 Cl 0.45422(4) 0.73161(15) 0.47525(9) 0.0403(3) Uani 1 1 d . . . . .
Cl3 Cl 0.49000(5) 0.57608(14) 0.64675(11) 0.0487(4) Uani 1 1 d . . . . .
C31 C 0.44208(14) 0.6600(5) 0.5951(4) 0.0277(10) Uani 1 1 d . . . . .
H31A H 0.4165 0.5945 0.5879 0.033 Uiso 1 1 calc R . . . .
H31B H 0.4322 0.7325 0.6427 0.033 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
Pd1 Cl1 2.2989(10) . ?
Pd1 P1 2.3170(10) . ?
Pd1 P2 2.2779(10) . ?
Pd1 N1 2.073(3) . ?
P1 C1 1.861(4) . ?
P1 C4 1.884(4) . ?
P1 C11 1.829(4) . ?
P2 C16 1.863(4) . ?
P2 C19 1.891(4) . ?
P2 C26 1.819(4) . ?
O1 C1 1.451(4) . ?
O1 C2 1.444(4) . ?
O2 C4 1.436(4) . ?
O2 C6 1.433(4) . ?
O3 C2 1.428(5) . ?
O3 C6 1.430(4) . ?
O4 C16 1.440(4) . ?
O4 C17 1.440(4) . ?
O5 C17 1.422(4) . ?
O5 C21 1.425(5) . ?
O6 C19 1.441(4) . ?
O6 C21 1.437(5) . ?
N1 C11 1.357(5) . ?
N1 C15 1.340(5) . ?
N2 C26 1.333(5) . ?
N2 C30 1.345(5) . ?
C1 C5 1.521(5) . ?
C1 C7 1.515(5) . ?
C2 C3 1.516(5) . ?
C2 C8 1.509(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(5) . ?
C4 C9 1.511(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(5) . ?
C6 C10 1.512(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C20 1.533(5) . ?
C16 C22 1.511(5) . ?
C17 C18 1.528(5) . ?
C17 C23 1.503(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.525(5) . ?
C19 C24 1.512(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.515(6) . ?
C21 C25 1.507(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.394(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.374(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.394(6) . ?
C30 H30 0.9500 . ?
F0AA B1 1.370(7) . ?
B1 F1 1.37(3) . ?
B1 F4 1.410(17) . ?
B1 F7 1.433(16) . ?
B1 F1A 1.37(4) . ?
B1 F4A 1.385(11) . ?
B1 F7A 1.41(2) . ?
B1 F2 1.39(3) . ?
B1 F6 1.41(4) . ?
B1 F9 1.36(5) . ?
Cl2 C31 1.750(5) . ?
Cl3 C31 1.759(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Pd1 P1 161.35(3) . . ?
P2 Pd1 Cl1 86.17(4) . . ?
P2 Pd1 P1 112.44(3) . . ?
N1 Pd1 Cl1 92.52(9) . . ?
N1 Pd1 P1 68.95(9) . . ?
N1 Pd1 P2 176.87(9) . . ?
C1 P1 Pd1 135.10(12) . . ?
C1 P1 C4 95.33(17) . . ?
C4 P1 Pd1 123.45(13) . . ?
C11 P1 Pd1 82.81(12) . . ?
C11 P1 C1 106.85(17) . . ?
C11 P1 C4 109.10(17) . . ?
C16 P2 Pd1 120.46(12) . . ?
C16 P2 C19 94.48(16) . . ?
C19 P2 Pd1 113.11(12) . . ?
C26 P2 Pd1 110.22(14) . . ?
C26 P2 C16 105.82(17) . . ?
C26 P2 C19 111.75(19) . . ?
C2 O1 C1 116.6(3) . . ?
C6 O2 C4 116.5(3) . . ?
C2 O3 C6 111.8(3) . . ?
C16 O4 C17 115.6(3) . . ?
C17 O5 C21 112.4(3) . . ?
C21 O6 C19 116.0(3) . . ?
C11 N1 Pd1 105.6(2) . . ?
C15 N1 Pd1 133.8(3) . . ?
C15 N1 C11 120.1(3) . . ?
C26 N2 C30 117.3(4) . . ?
O1 C1 P1 106.8(2) . . ?
O1 C1 C5 109.5(3) . . ?
O1 C1 C7 106.5(3) . . ?
C5 C1 P1 107.8(2) . . ?
C7 C1 P1 111.3(3) . . ?
C7 C1 C5 114.6(3) . . ?
O1 C2 C3 111.3(3) . . ?
O1 C2 C8 105.9(3) . . ?
O3 C2 O1 109.9(3) . . ?
O3 C2 C3 108.3(3) . . ?
O3 C2 C8 107.5(3) . . ?
C8 C2 C3 113.9(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 C4 110.6(3) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
O2 C4 P1 106.9(2) . . ?
O2 C4 C3 109.2(3) . . ?
O2 C4 C9 107.0(3) . . ?
C3 C4 P1 108.0(2) . . ?
C9 C4 P1 110.8(3) . . ?
C9 C4 C3 114.6(3) . . ?
C1 C5 H5A 109.6 . . ?
C1 C5 H5B 109.6 . . ?
C1 C5 C6 110.4(3) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
O2 C6 C5 110.6(3) . . ?
O2 C6 C10 105.9(3) . . ?
O3 C6 O2 111.2(3) . . ?
O3 C6 C5 108.1(3) . . ?
O3 C6 C10 107.6(3) . . ?
C10 C6 C5 113.4(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 101.9(3) . . ?
N1 C11 C12 122.0(3) . . ?
C12 C11 P1 136.0(3) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.7(4) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(4) . . ?
C15 C14 H14 120.1 . . ?
N1 C15 C14 120.4(4) . . ?
N1 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O4 C16 P2 106.5(2) . . ?
O4 C16 C20 109.1(3) . . ?
O4 C16 C22 107.1(3) . . ?
C20 C16 P2 109.7(2) . . ?
C22 C16 P2 111.8(3) . . ?
C22 C16 C20 112.4(3) . . ?
O4 C17 C18 111.9(3) . . ?
O4 C17 C23 105.9(3) . . ?
O5 C17 O4 110.1(3) . . ?
O5 C17 C18 108.1(3) . . ?
O5 C17 C23 106.2(3) . . ?
C23 C17 C18 114.5(3) . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 C17 110.2(3) . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
O6 C19 P2 110.6(2) . . ?
O6 C19 C18 109.7(3) . . ?
O6 C19 C24 105.2(3) . . ?
C18 C19 P2 104.4(2) . . ?
C24 C19 P2 113.2(3) . . ?
C24 C19 C18 113.8(3) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C16 110.9(3) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
O5 C21 O6 110.6(3) . . ?
O5 C21 C20 108.5(3) . . ?
O5 C21 C25 106.4(3) . . ?
O6 C21 C20 110.1(3) . . ?
O6 C21 C25 106.9(3) . . ?
C25 C21 C20 114.3(3) . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 P2 111.6(3) . . ?
N2 C26 C27 124.0(4) . . ?
C27 C26 P2 124.4(3) . . ?
C26 C27 H27 121.2 . . ?
C28 C27 C26 117.5(4) . . ?
C28 C27 H27 121.2 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.7(4) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.6 . . ?
C28 C29 C30 118.7(4) . . ?
C30 C29 H29 120.6 . . ?
N2 C30 C29 122.7(4) . . ?
N2 C30 H30 118.7 . . ?
C29 C30 H30 118.7 . . ?
F0AA B1 F1 109.6(14) . . ?
F0AA B1 F4 109.9(10) . . ?
F0AA B1 F7 106.9(8) . . ?
F0AA B1 F4A 112.2(12) . . ?
F0AA B1 F7A 111.3(8) . . ?
F0AA B1 F2 103.1(12) . . ?
F0AA B1 F6 109.8(16) . . ?
F1 B1 F4 111.8(16) . . ?
F1 B1 F7 106.4(14) . . ?
F4 B1 F7 112.0(11) . . ?
F1A B1 F0AA 116.1(19) . . ?
F1A B1 F4A 104(2) . . ?
F1A B1 F7A 109.6(18) . . ?
F4A B1 F7A 102.8(14) . . ?
F2 B1 F6 108.4(16) . . ?
F9 B1 F0AA 112(2) . . ?
F9 B1 F2 108.5(15) . . ?
F9 B1 F6 115(2) . . ?
Cl2 C31 Cl3 111.7(2) . . ?
Cl2 C31 H31A 109.3 . . ?
Cl2 C31 H31B 109.3 . . ?
Cl3 C31 H31A 109.3 . . ?
Cl3 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 P1 C1 O1 150.38(16) . . . . ?
Pd1 P1 C1 C5 -92.0(3) . . . . ?
Pd1 P1 C1 C7 34.6(3) . . . . ?
Pd1 P1 C4 O2 98.4(2) . . . . ?
Pd1 P1 C4 C3 -144.2(2) . . . . ?
Pd1 P1 C4 C9 -17.9(3) . . . . ?
Pd1 P1 C11 N1 6.9(2) . . . . ?
Pd1 P1 C11 C12 -171.3(4) . . . . ?
Pd1 P2 C16 O4 -57.9(3) . . . . ?
Pd1 P2 C16 C20 -175.8(2) . . . . ?
Pd1 P2 C16 C22 58.8(3) . . . . ?
Pd1 P2 C19 O6 -180.0(2) . . . . ?
Pd1 P2 C19 C18 62.1(2) . . . . ?
Pd1 P2 C19 C24 -62.2(3) . . . . ?
Pd1 P2 C26 N2 -38.5(3) . . . . ?
Pd1 P2 C26 C27 141.0(3) . . . . ?
Pd1 N1 C11 P1 -7.9(2) . . . . ?
Pd1 N1 C11 C12 170.6(3) . . . . ?
Pd1 N1 C15 C14 -170.4(3) . . . . ?
P1 C1 C5 C6 -66.3(3) . . . . ?
P1 C11 C12 C13 179.9(3) . . . . ?
P2 C16 C20 C21 66.3(4) . . . . ?
P2 C26 C27 C28 -177.4(3) . . . . ?
O1 C1 C5 C6 49.5(4) . . . . ?
O1 C2 C3 C4 63.0(4) . . . . ?
O3 C2 C3 C4 -57.9(4) . . . . ?
O4 C16 C20 C21 -50.1(4) . . . . ?
O4 C17 C18 C19 -64.4(4) . . . . ?
O5 C17 C18 C19 57.0(4) . . . . ?
N1 C11 C12 C13 2.1(6) . . . . ?
N2 C26 C27 C28 2.0(6) . . . . ?
C1 P1 C4 O2 -57.7(3) . . . . ?
C1 P1 C4 C3 59.7(3) . . . . ?
C1 P1 C4 C9 -174.0(3) . . . . ?
C1 P1 C11 N1 141.9(2) . . . . ?
C1 P1 C11 C12 -36.2(4) . . . . ?
C1 O1 C2 O3 53.3(4) . . . . ?
C1 O1 C2 C3 -66.6(4) . . . . ?
C1 O1 C2 C8 169.1(3) . . . . ?
C1 C5 C6 O2 64.4(4) . . . . ?
C1 C5 C6 O3 -57.6(4) . . . . ?
C1 C5 C6 C10 -176.8(3) . . . . ?
C2 O1 C1 P1 67.8(3) . . . . ?
C2 O1 C1 C5 -48.7(4) . . . . ?
C2 O1 C1 C7 -173.2(3) . . . . ?
C2 O3 C6 O2 -58.1(4) . . . . ?
C2 O3 C6 C5 63.5(4) . . . . ?
C2 O3 C6 C10 -173.7(3) . . . . ?
C2 C3 C4 P1 -65.1(3) . . . . ?
C2 C3 C4 O2 50.8(4) . . . . ?
C2 C3 C4 C9 170.8(3) . . . . ?
C4 P1 C1 O1 -58.2(2) . . . . ?
C4 P1 C1 C5 59.4(3) . . . . ?
C4 P1 C1 C7 -174.1(3) . . . . ?
C4 P1 C11 N1 -116.1(3) . . . . ?
C4 P1 C11 C12 65.8(4) . . . . ?
C4 O2 C6 O3 52.5(4) . . . . ?
C4 O2 C6 C5 -67.7(4) . . . . ?
C4 O2 C6 C10 169.1(3) . . . . ?
C6 O2 C4 P1 67.7(3) . . . . ?
C6 O2 C4 C3 -49.0(4) . . . . ?
C6 O2 C4 C9 -173.5(3) . . . . ?
C6 O3 C2 O1 -60.3(4) . . . . ?
C6 O3 C2 C3 61.4(4) . . . . ?
C6 O3 C2 C8 -175.1(3) . . . . ?
C7 C1 C5 C6 169.1(3) . . . . ?
C8 C2 C3 C4 -177.4(3) . . . . ?
C11 P1 C1 O1 53.6(3) . . . . ?
C11 P1 C1 C5 171.2(2) . . . . ?
C11 P1 C1 C7 -62.3(3) . . . . ?
C11 P1 C4 O2 -167.6(2) . . . . ?
C11 P1 C4 C3 -50.2(3) . . . . ?
C11 P1 C4 C9 76.1(3) . . . . ?
C11 N1 C15 C14 0.3(6) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
C12 C13 C14 C15 -2.5(6) . . . . ?
C13 C14 C15 N1 2.2(6) . . . . ?
C15 N1 C11 P1 179.1(3) . . . . ?
C15 N1 C11 C12 -2.4(6) . . . . ?
C16 P2 C19 O6 54.2(3) . . . . ?
C16 P2 C19 C18 -63.8(3) . . . . ?
C16 P2 C19 C24 171.9(3) . . . . ?
C16 P2 C26 N2 93.3(3) . . . . ?
C16 P2 C26 C27 -87.2(4) . . . . ?
C16 O4 C17 O5 -55.5(4) . . . . ?
C16 O4 C17 C18 64.7(4) . . . . ?
C16 O4 C17 C23 -169.9(3) . . . . ?
C16 C20 C21 O5 55.7(4) . . . . ?
C16 C20 C21 O6 -65.5(4) . . . . ?
C16 C20 C21 C25 174.3(3) . . . . ?
C17 O4 C16 P2 -67.7(3) . . . . ?
C17 O4 C16 C20 50.7(4) . . . . ?
C17 O4 C16 C22 172.5(3) . . . . ?
C17 O5 C21 O6 59.6(4) . . . . ?
C17 O5 C21 C20 -61.3(4) . . . . ?
C17 O5 C21 C25 175.3(3) . . . . ?
C17 C18 C19 P2 68.3(3) . . . . ?
C17 C18 C19 O6 -50.2(4) . . . . ?
C17 C18 C19 C24 -167.8(3) . . . . ?
C19 P2 C16 O4 62.3(3) . . . . ?
C19 P2 C16 C20 -55.7(3) . . . . ?
C19 P2 C16 C22 179.0(3) . . . . ?
C19 P2 C26 N2 -165.2(3) . . . . ?
C19 P2 C26 C27 14.4(4) . . . . ?
C19 O6 C21 O5 -53.2(4) . . . . ?
C19 O6 C21 C20 66.7(4) . . . . ?
C19 O6 C21 C25 -168.6(3) . . . . ?
C21 O5 C17 O4 60.3(4) . . . . ?
C21 O5 C17 C18 -62.2(4) . . . . ?
C21 O5 C17 C23 174.5(3) . . . . ?
C21 O6 C19 P2 -65.3(4) . . . . ?
C21 O6 C19 C18 49.3(4) . . . . ?
C21 O6 C19 C24 172.1(3) . . . . ?
C22 C16 C20 C21 -168.7(3) . . . . ?
C23 C17 C18 C19 175.2(3) . . . . ?
C26 P2 C16 O4 176.4(2) . . . . ?
C26 P2 C16 C20 58.5(3) . . . . ?
C26 P2 C16 C22 -66.9(3) . . . . ?
C26 P2 C19 O6 -54.9(3) . . . . ?
C26 P2 C19 C18 -172.8(2) . . . . ?
C26 P2 C19 C24 62.9(3) . . . . ?
C26 N2 C30 C29 0.1(6) . . . . ?
C26 C27 C28 C29 -0.5(6) . . . . ?
C27 C28 C29 C30 -1.1(6) . . . . ?
C28 C29 C30 N2 1.4(7) . . . . ?
C30 N2 C26 P2 177.7(3) . . . . ?
C30 N2 C26 C27 -1.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.60(3)
2 0.40(3)
####################################################################### 
# 
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 1497891'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H20 N O3 P'
_chemical_formula_sum            'C15 H20 N O3 P'
_chemical_formula_weight         293.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.9601(3)
_cell_length_b                   14.7432(5)
_cell_length_c                   24.8613(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.416(3)
_cell_angle_gamma                90
_cell_volume                     2912.47(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2503
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0616 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.8225.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.825
_diffrn_reflns_theta_min         1.641
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2428
_reflns_number_total             3126
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.023
_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)+(0.0371P)²+1.9037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0881
_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:
 C5(H5A,H5B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.14262(6) 0.42344(3) 0.33190(2) 0.01522(12) Uani 1 1 d . . . . .
O2 O 0.14186(14) 0.36644(7) 0.44023(4) 0.0144(3) Uani 1 1 d . . . . .
O3 O 0.25149(14) 0.50515(7) 0.47375(4) 0.0152(3) Uani 1 1 d . . . . .
O1 O 0.27778(14) 0.56266(7) 0.38650(4) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.29216(19) 0.15426(10) 0.32958(6) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.2446(2) 0.23607(12) 0.34639(7) 0.0192(4) Uani 1 1 d . . . . .
H15 H 0.2323 0.2441 0.3839 0.023 Uiso 1 1 calc R . . . .
C11 C 0.2118(2) 0.31041(11) 0.31263(7) 0.0161(4) Uani 1 1 d . . . . .
C12 C 0.2270(2) 0.29572(12) 0.25754(7) 0.0208(4) Uani 1 1 d . . . . .
H12 H 0.2039 0.3437 0.2327 0.025 Uiso 1 1 calc R . . . .
C13 C 0.2754(2) 0.21179(13) 0.23917(7) 0.0243(4) Uani 1 1 d . . . . .
H13 H 0.2863 0.2011 0.2018 0.029 Uiso 1 1 calc R . . . .
C14 C 0.3077(2) 0.14371(13) 0.27664(7) 0.0225(4) Uani 1 1 d . . . . .
H14 H 0.3429 0.0863 0.2641 0.027 Uiso 1 1 calc R . . . .
C4 C 0.0389(2) 0.40975(11) 0.39721(6) 0.0147(3) Uani 1 1 d . . . . .
C5 C 0.0043(2) 0.50673(11) 0.41438(7) 0.0166(4) Uani 1 1 d . . . . .
H5A H -0.0685 0.5063 0.4453 0.020 Uiso 1 1 calc R . . . .
H5B H -0.0557 0.5396 0.3843 0.020 Uiso 1 1 calc R . . . .
C6 C 0.1688(2) 0.55517(11) 0.43034(6) 0.0161(4) Uani 1 1 d . . . . .
C1 C 0.3363(2) 0.47682(11) 0.36585(7) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.4125(2) 0.42104(11) 0.41282(6) 0.0148(3) Uani 1 1 d . . . . .
H2A H 0.4391 0.3593 0.4001 0.018 Uiso 1 1 calc R . . . .
H2B H 0.5187 0.4496 0.4269 0.018 Uiso 1 1 calc R . . . .
C3 C 0.2911(2) 0.41456(11) 0.45768(6) 0.0141(3) Uani 1 1 d . . . . .
C9 C -0.1205(2) 0.35332(12) 0.39077(7) 0.0196(4) Uani 1 1 d . . . . .
H9A H -0.1972 0.3803 0.3629 0.029 Uiso 1 1 calc GR . . . .
H9B H -0.1753 0.3518 0.4250 0.029 Uiso 1 1 calc GR . . . .
H9C H -0.0920 0.2914 0.3802 0.029 Uiso 1 1 calc GR . . . .
C10 C 0.1428(2) 0.65041(11) 0.44997(7) 0.0209(4) Uani 1 1 d . . . . .
H10A H 0.0691 0.6493 0.4802 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.0906 0.6871 0.4206 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.2516 0.6769 0.4619 0.031 Uiso 1 1 calc GR . . . .
C7 C 0.4646(2) 0.49942(12) 0.32537(7) 0.0212(4) Uani 1 1 d . . . . .
H7A H 0.5038 0.4433 0.3091 0.032 Uiso 1 1 calc GR . . . .
H7B H 0.5603 0.5309 0.3436 0.032 Uiso 1 1 calc GR . . . .
H7C H 0.4129 0.5386 0.2972 0.032 Uiso 1 1 calc GR . . . .
C8 C 0.3631(2) 0.36658(11) 0.50726(7) 0.0177(4) Uani 1 1 d . . . . .
H8A H 0.2804 0.3670 0.5349 0.027 Uiso 1 1 calc GR . . . .
H8B H 0.4657 0.3977 0.5210 0.027 Uiso 1 1 calc GR . . . .
H8C H 0.3900 0.3038 0.4982 0.027 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
P1 C11 1.8278(17) . ?
P1 C4 1.8757(16) . ?
P1 C1 1.8850(18) . ?
O2 C4 1.4558(19) . ?
O2 C3 1.4287(19) . ?
O3 C6 1.4343(19) . ?
O3 C3 1.4345(19) . ?
O1 C6 1.4372(19) . ?
O1 C1 1.4526(19) . ?
N1 C15 1.338(2) . ?
N1 C14 1.338(2) . ?
C15 H15 0.9500 . ?
C15 C11 1.396(2) . ?
C11 C12 1.399(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C4 C5 1.522(2) . ?
C4 C9 1.518(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.523(2) . ?
C6 C10 1.505(2) . ?
C1 C2 1.524(2) . ?
C1 C7 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.522(2) . ?
C3 C8 1.505(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 C4 106.49(8) . . ?
C11 P1 C1 104.30(7) . . ?
C4 P1 C1 92.73(7) . . ?
C3 O2 C4 115.27(12) . . ?
C6 O3 C3 111.58(12) . . ?
C6 O1 C1 114.94(12) . . ?
C14 N1 C15 117.14(16) . . ?
N1 C15 H15 117.8 . . ?
N1 C15 C11 124.49(16) . . ?
C11 C15 H15 117.8 . . ?
C15 C11 P1 127.36(13) . . ?
C15 C11 C12 116.30(16) . . ?
C12 C11 P1 116.28(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.29(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.14(17) . . ?
C14 C13 H13 120.9 . . ?
N1 C14 C13 123.62(17) . . ?
N1 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
O2 C4 P1 115.19(11) . . ?
O2 C4 C5 108.01(13) . . ?
O2 C4 C9 105.52(13) . . ?
C5 C4 P1 103.77(11) . . ?
C9 C4 P1 112.09(11) . . ?
C9 C4 C5 112.37(14) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.28(13) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
O3 C6 O1 109.84(13) . . ?
O3 C6 C5 107.68(13) . . ?
O3 C6 C10 107.55(13) . . ?
O1 C6 C5 112.76(13) . . ?
O1 C6 C10 105.98(13) . . ?
C10 C6 C5 112.90(14) . . ?
O1 C1 P1 104.55(11) . . ?
O1 C1 C2 108.71(13) . . ?
O1 C1 C7 106.65(13) . . ?
C2 C1 P1 113.29(11) . . ?
C7 C1 P1 111.14(12) . . ?
C7 C1 C2 111.99(14) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.73(13) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
O2 C3 O3 110.75(12) . . ?
O2 C3 C2 111.19(13) . . ?
O2 C3 C8 106.52(13) . . ?
O3 C3 C2 107.78(13) . . ?
O3 C3 C8 106.79(13) . . ?
C8 C3 C2 113.74(14) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
P1 C11 C12 C13 -178.76(14) . . . . ?
P1 C4 C5 C6 -69.20(14) . . . . ?
P1 C1 C2 C3 -64.04(16) . . . . ?
O2 C4 C5 C6 53.51(17) . . . . ?
O1 C1 C2 C3 51.71(17) . . . . ?
N1 C15 C11 P1 178.71(13) . . . . ?
N1 C15 C11 C12 1.5(3) . . . . ?
C15 N1 C14 C13 -0.9(3) . . . . ?
C15 C11 C12 C13 -1.3(3) . . . . ?
C11 P1 C4 O2 55.35(13) . . . . ?
C11 P1 C4 C5 173.20(10) . . . . ?
C11 P1 C4 C9 -65.31(13) . . . . ?
C11 P1 C1 O1 -173.93(10) . . . . ?
C11 P1 C1 C2 -55.73(13) . . . . ?
C11 P1 C1 C7 71.38(13) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 N1 1.1(3) . . . . ?
C14 N1 C15 C11 -0.5(3) . . . . ?
C4 P1 C11 C15 -23.10(18) . . . . ?
C4 P1 C11 C12 154.08(13) . . . . ?
C4 P1 C1 O1 -66.15(11) . . . . ?
C4 P1 C1 C2 52.05(12) . . . . ?
C4 P1 C1 C7 179.17(12) . . . . ?
C4 O2 C3 O3 55.54(16) . . . . ?
C4 O2 C3 C2 -64.27(17) . . . . ?
C4 O2 C3 C8 171.31(12) . . . . ?
C4 C5 C6 O3 -59.05(17) . . . . ?
C4 C5 C6 O1 62.29(17) . . . . ?
C4 C5 C6 C10 -177.61(13) . . . . ?
C6 O3 C3 O2 -59.64(16) . . . . ?
C6 O3 C3 C2 62.19(16) . . . . ?
C6 O3 C3 C8 -175.24(13) . . . . ?
C6 O1 C1 P1 69.12(14) . . . . ?
C6 O1 C1 C2 -52.16(17) . . . . ?
C6 O1 C1 C7 -173.08(13) . . . . ?
C1 P1 C11 C15 74.18(17) . . . . ?
C1 P1 C11 C12 -108.64(14) . . . . ?
C1 P1 C4 O2 -50.43(12) . . . . ?
C1 P1 C4 C5 67.42(11) . . . . ?
C1 P1 C4 C9 -171.09(12) . . . . ?
C1 O1 C6 O3 56.75(17) . . . . ?
C1 O1 C6 C5 -63.35(17) . . . . ?
C1 O1 C6 C10 172.65(13) . . . . ?
C1 C2 C3 O2 64.28(17) . . . . ?
C1 C2 C3 O3 -57.28(16) . . . . ?
C1 C2 C3 C8 -175.48(14) . . . . ?
C3 O2 C4 P1 62.87(15) . . . . ?
C3 O2 C4 C5 -52.57(17) . . . . ?
C3 O2 C4 C9 -172.94(12) . . . . ?
C3 O3 C6 O1 -61.52(16) . . . . ?
C3 O3 C6 C5 61.63(16) . . . . ?
C3 O3 C6 C10 -176.42(13) . . . . ?
C9 C4 C5 C6 169.49(13) . . . . ?
C7 C1 C2 C3 169.29(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L4
_database_code_depnum_ccdc_archive 'CCDC 1497892'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H19 N2 O3 P'
_chemical_formula_sum            'C14 H19 N2 O3 P'
_chemical_formula_weight         294.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.9879(8)
_cell_length_b                   8.0408(5)
_cell_length_c                   25.4615(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.511(3)
_cell_angle_gamma                90
_cell_volume                     2824.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0514 before and 0.0420 after correction.
The Ratio of minimum to maximum transmission is 0.9134.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12722
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.033
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2910
_reflns_number_total             3422
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.028
_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)+(0.0370P)²+2.5878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0834
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.61933(2) 0.48618(4) 0.33131(2) 0.01207(9) Uani 1 1 d . . . . .
O1 O 0.70904(6) 0.57298(11) 0.43382(3) 0.01227(19) Uani 1 1 d . . . . .
O2 O 0.61966(7) 0.38117(11) 0.47558(3) 0.01295(19) Uani 1 1 d . . . . .
O3 O 0.53010(7) 0.29886(11) 0.39344(4) 0.0136(2) Uani 1 1 d . . . . .
N1 N 0.55973(8) 0.81781(14) 0.32563(4) 0.0161(2) Uani 1 1 d . . . . .
N2 N 0.69661(8) 0.73998(14) 0.28613(4) 0.0157(2) Uani 1 1 d . . . . .
C1 C 0.71886(9) 0.46204(16) 0.39065(5) 0.0125(2) Uani 1 1 d . . . . .
C2 C 0.70722(9) 0.28330(16) 0.40933(5) 0.0136(3) Uani 1 1 d . . . . .
H2A H 0.7055 0.2076 0.3795 0.016 Uiso 1 1 calc R . . . .
H2B H 0.7622 0.2537 0.4361 0.016 Uiso 1 1 calc R . . . .
C3 C 0.61415(9) 0.26680(16) 0.43249(5) 0.0133(3) Uani 1 1 d . . . . .
C4 C 0.52119(9) 0.46810(16) 0.37284(5) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.53299(9) 0.58838(16) 0.41952(5) 0.0123(3) Uani 1 1 d . . . . .
H5A H 0.5358 0.7014 0.4065 0.015 Uiso 1 1 calc R . . . .
H5B H 0.4775 0.5797 0.4377 0.015 Uiso 1 1 calc R . . . .
C6 C 0.62488(9) 0.54976(16) 0.45818(5) 0.0119(2) Uani 1 1 d . . . . .
C7 C 0.81898(10) 0.49318(18) 0.37770(5) 0.0172(3) Uani 1 1 d . . . . .
H7A H 0.8306 0.4189 0.3499 0.026 Uiso 1 1 calc GR . . . .
H7B H 0.8665 0.4743 0.4089 0.026 Uiso 1 1 calc GR . . . .
H7C H 0.8234 0.6061 0.3661 0.026 Uiso 1 1 calc GR . . . .
C8 C 0.60017(11) 0.09656(16) 0.45460(5) 0.0174(3) Uani 1 1 d . . . . .
H8A H 0.6538 0.0710 0.4821 0.026 Uiso 1 1 calc GR . . . .
H8B H 0.5967 0.0156 0.4266 0.026 Uiso 1 1 calc GR . . . .
H8C H 0.5411 0.0945 0.4692 0.026 Uiso 1 1 calc GR . . . .
C9 C 0.42188(10) 0.47715(18) 0.33883(6) 0.0178(3) Uani 1 1 d . . . . .
H9A H 0.4121 0.5861 0.3234 0.027 Uiso 1 1 calc GR . . . .
H9B H 0.3732 0.4555 0.3605 0.027 Uiso 1 1 calc GR . . . .
H9C H 0.4173 0.3956 0.3110 0.027 Uiso 1 1 calc GR . . . .
C10 C 0.63821(10) 0.65705(16) 0.50720(5) 0.0147(3) Uani 1 1 d . . . . .
H10A H 0.6925 0.6174 0.5321 0.022 Uiso 1 1 calc GR . . . .
H10B H 0.5808 0.6525 0.5232 0.022 Uiso 1 1 calc GR . . . .
H10C H 0.6498 0.7698 0.4976 0.022 Uiso 1 1 calc GR . . . .
C11 C 0.62534(9) 0.70809(16) 0.31419(5) 0.0131(3) Uani 1 1 d . . . . .
C12 C 0.56913(11) 0.97411(17) 0.30892(5) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.5255 1.0542 0.3166 0.022 Uiso 1 1 calc R . . . .
C13 C 0.64087(10) 1.02057(17) 0.28083(5) 0.0176(3) Uani 1 1 d . . . . .
H13 H 0.6468 1.1296 0.2696 0.021 Uiso 1 1 calc R . . . .
C14 C 0.70346(10) 0.89739(18) 0.27011(5) 0.0170(3) Uani 1 1 d . . . . .
H14 H 0.7524 0.9248 0.2510 0.020 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 C1 1.8876(13) . ?
P1 C4 1.8718(14) . ?
P1 C11 1.8420(14) . ?
O1 C1 1.4398(15) . ?
O1 C6 1.4306(15) . ?
O2 C3 1.4240(15) . ?
O2 C6 1.4317(15) . ?
O3 C3 1.4322(15) . ?
O3 C4 1.4563(15) . ?
N1 C11 1.3393(17) . ?
N1 C12 1.3402(17) . ?
N2 C11 1.3436(17) . ?
N2 C14 1.3382(17) . ?
C1 C2 1.5310(18) . ?
C1 C7 1.5117(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.5212(18) . ?
C3 C8 1.5050(18) . ?
C4 C5 1.5200(17) . ?
C4 C9 1.5124(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5164(18) . ?
C6 C10 1.5033(17) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.377(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 P1 C1 93.02(6) . . ?
C11 P1 C1 103.45(6) . . ?
C11 P1 C4 105.98(6) . . ?
C6 O1 C1 116.06(9) . . ?
C3 O2 C6 111.84(9) . . ?
C3 O3 C4 115.47(9) . . ?
C11 N1 C12 116.23(12) . . ?
C14 N2 C11 116.07(12) . . ?
O1 C1 P1 113.36(8) . . ?
O1 C1 C2 108.41(10) . . ?
O1 C1 C7 105.82(10) . . ?
C2 C1 P1 104.06(8) . . ?
C7 C1 P1 113.32(9) . . ?
C7 C1 C2 111.91(11) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.13(10) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
O2 C3 O3 110.64(10) . . ?
O2 C3 C2 107.55(10) . . ?
O2 C3 C8 107.05(10) . . ?
O3 C3 C2 111.84(10) . . ?
O3 C3 C8 106.32(10) . . ?
C8 C3 C2 113.37(11) . . ?
O3 C4 P1 104.41(8) . . ?
O3 C4 C5 108.73(10) . . ?
O3 C4 C9 105.49(10) . . ?
C5 C4 P1 113.40(9) . . ?
C9 C4 P1 111.28(9) . . ?
C9 C4 C5 112.82(11) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.38(10) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
O1 C6 O2 110.21(10) . . ?
O1 C6 C5 111.21(10) . . ?
O1 C6 C10 106.67(10) . . ?
O2 C6 C5 108.28(10) . . ?
O2 C6 C10 106.98(10) . . ?
C10 C6 C5 113.39(11) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 121.80(10) . . ?
N1 C11 N2 125.82(12) . . ?
N2 C11 P1 112.18(10) . . ?
N1 C12 H12 118.7 . . ?
N1 C12 C13 122.52(13) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 121.7 . . ?
C12 C13 C14 116.69(13) . . ?
C14 C13 H13 121.7 . . ?
N2 C14 C13 122.63(13) . . ?
N2 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -68.78(11) . . . . ?
P1 C4 C5 C6 -63.95(12) . . . . ?
O1 C1 C2 C3 52.17(13) . . . . ?
O3 C4 C5 C6 51.72(13) . . . . ?
N1 C12 C13 C14 0.4(2) . . . . ?
C1 P1 C4 O3 -65.22(8) . . . . ?
C1 P1 C4 C5 52.98(10) . . . . ?
C1 P1 C4 C9 -178.55(10) . . . . ?
C1 P1 C11 N1 -104.89(11) . . . . ?
C1 P1 C11 N2 79.99(10) . . . . ?
C1 O1 C6 O2 54.81(13) . . . . ?
C1 O1 C6 C5 -65.28(13) . . . . ?
C1 O1 C6 C10 170.61(10) . . . . ?
C1 C2 C3 O2 -58.66(13) . . . . ?
C1 C2 C3 O3 63.01(13) . . . . ?
C1 C2 C3 C8 -176.80(10) . . . . ?
C3 O2 C6 O1 -60.07(13) . . . . ?
C3 O2 C6 C5 61.77(13) . . . . ?
C3 O2 C6 C10 -175.68(10) . . . . ?
C3 O3 C4 P1 70.26(11) . . . . ?
C3 O3 C4 C5 -51.09(13) . . . . ?
C3 O3 C4 C9 -172.35(11) . . . . ?
C4 P1 C1 O1 -51.11(9) . . . . ?
C4 P1 C1 C2 66.46(9) . . . . ?
C4 P1 C1 C7 -171.74(10) . . . . ?
C4 P1 C11 N1 -7.71(12) . . . . ?
C4 P1 C11 N2 177.16(9) . . . . ?
C4 O3 C3 O2 54.80(14) . . . . ?
C4 O3 C3 C2 -65.07(13) . . . . ?
C4 O3 C3 C8 170.69(10) . . . . ?
C4 C5 C6 O1 63.42(13) . . . . ?
C4 C5 C6 O2 -57.81(13) . . . . ?
C4 C5 C6 C10 -176.37(10) . . . . ?
C6 O1 C1 P1 63.75(12) . . . . ?
C6 O1 C1 C2 -51.26(13) . . . . ?
C6 O1 C1 C7 -171.46(10) . . . . ?
C6 O2 C3 O3 -59.68(13) . . . . ?
C6 O2 C3 C2 62.74(12) . . . . ?
C6 O2 C3 C8 -175.11(10) . . . . ?
C7 C1 C2 C3 168.50(10) . . . . ?
C9 C4 C5 C6 168.38(11) . . . . ?
C11 P1 C1 O1 56.11(10) . . . . ?
C11 P1 C1 C2 173.69(8) . . . . ?
C11 P1 C1 C7 -64.52(10) . . . . ?
C11 P1 C4 O3 -170.13(7) . . . . ?
C11 P1 C4 C5 -51.94(10) . . . . ?
C11 P1 C4 C9 76.54(10) . . . . ?
C11 N1 C12 C13 0.96(19) . . . . ?
C11 N2 C14 C13 -0.82(19) . . . . ?
C12 N1 C11 P1 -176.91(10) . . . . ?
C12 N1 C11 N2 -2.48(19) . . . . ?
C12 C13 C14 N2 -0.5(2) . . . . ?
C14 N2 C11 P1 177.30(9) . . . . ?
C14 N2 C11 N1 2.41(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L5a
_database_code_depnum_ccdc_archive 'CCDC 1497893'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H22 N O3 P'
_chemical_formula_sum            'C16 H22 N O3 P'
_chemical_formula_weight         307.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3067(5)
_cell_length_b                   12.0198(4)
_cell_length_c                   7.7629(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.552(2)
_cell_angle_gamma                90
_cell_volume                     1520.04(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4279
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0636 before and 0.0412 after correction.
The Ratio of minimum to maximum transmission is 0.8281.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12114
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.761
_diffrn_reflns_theta_min         1.250
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2833
_reflns_number_total             3227
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.040
_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)+(0.0377P)²+0.7570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0832
_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:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.25789(2) 0.42673(3) 0.26715(4) 0.01045(10) Uani 1 1 d . . . . .
O1 O 0.18377(6) 0.62312(8) 0.25187(12) 0.0134(2) Uani 1 1 d . . . . .
O2 O 0.17148(6) 0.42280(8) -0.05351(12) 0.0114(2) Uani 1 1 d . . . . .
O3 O 0.11068(6) 0.59785(8) -0.01324(12) 0.0134(2) Uani 1 1 d . . . . .
N1 N 0.40532(7) 0.41544(10) 0.10219(15) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.25885(8) 0.57520(11) 0.19000(18) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.10930(8) 0.58310(12) 0.16920(18) 0.0134(3) Uani 1 1 d . . . . .
C3 C 0.09610(8) 0.45926(11) 0.20269(18) 0.0129(3) Uani 1 1 d . . . . .
H3A H 0.0434 0.4363 0.1515 0.016 Uiso 1 1 calc R . . . .
H3B H 0.0956 0.4459 0.3259 0.016 Uiso 1 1 calc R . . . .
C4 C 0.16469(8) 0.39089(11) 0.12535(17) 0.0113(3) Uani 1 1 d . . . . .
C5 C 0.25711(8) 0.58644(11) -0.00533(18) 0.0128(3) Uani 1 1 d . . . . .
H5A H 0.3034 0.5468 -0.0502 0.015 Uiso 1 1 calc R . . . .
H5B H 0.2621 0.6643 -0.0362 0.015 Uiso 1 1 calc R . . . .
C6 C 0.17751(8) 0.53973(11) -0.08553(17) 0.0128(3) Uani 1 1 d . . . . .
C7 C 0.32804(8) 0.64125(12) 0.27644(19) 0.0161(3) Uani 1 1 d . . . . .
H7A H 0.3246 0.6364 0.3993 0.024 Uiso 1 1 calc GR . . . .
H7B H 0.3237 0.7177 0.2414 0.024 Uiso 1 1 calc GR . . . .
H7C H 0.3797 0.6116 0.2435 0.024 Uiso 1 1 calc GR . . . .
C8 C 0.04162(8) 0.65477(13) 0.23453(19) 0.0183(3) Uani 1 1 d . . . . .
H8A H 0.0418 0.6502 0.3580 0.027 Uiso 1 1 calc GR . . . .
H8B H -0.0103 0.6293 0.1865 0.027 Uiso 1 1 calc GR . . . .
H8C H 0.0502 0.7306 0.2008 0.027 Uiso 1 1 calc GR . . . .
C9 C 0.14499(8) 0.26771(11) 0.12054(18) 0.0132(3) Uani 1 1 d . . . . .
H9A H 0.1860 0.2291 0.0587 0.020 Uiso 1 1 calc GR . . . .
H9B H 0.0922 0.2565 0.0637 0.020 Uiso 1 1 calc GR . . . .
H9C H 0.1443 0.2395 0.2362 0.020 Uiso 1 1 calc GR . . . .
C10 C 0.16910(9) 0.55457(12) -0.27859(18) 0.0172(3) Uani 1 1 d . . . . .
H10A H 0.1164 0.5278 -0.3200 0.026 Uiso 1 1 calc GR . . . .
H10B H 0.2115 0.5134 -0.3321 0.026 Uiso 1 1 calc GR . . . .
H10C H 0.1741 0.6320 -0.3064 0.026 Uiso 1 1 calc GR . . . .
C11 C 0.34385(8) 0.35589(11) 0.16699(16) 0.0113(3) Uani 1 1 d . . . . .
C12 C 0.34713(8) 0.23985(12) 0.18192(17) 0.0128(3) Uani 1 1 d . . . . .
H12 H 0.3047 0.2019 0.2325 0.015 Uiso 1 1 calc R . . . .
C13 C 0.41346(8) 0.18112(12) 0.12154(17) 0.0132(3) Uani 1 1 d . . . . .
C14 C 0.47616(8) 0.24312(12) 0.05257(18) 0.0146(3) Uani 1 1 d . . . . .
H14 H 0.5217 0.2077 0.0098 0.018 Uiso 1 1 calc R . . . .
C15 C 0.47008(8) 0.35793(12) 0.04814(18) 0.0150(3) Uani 1 1 d . . . . .
H15 H 0.5135 0.3978 0.0051 0.018 Uiso 1 1 calc R . . . .
C16 C 0.41742(9) 0.05634(12) 0.13218(19) 0.0177(3) Uani 1 1 d . . . . .
H16A H 0.3731 0.0295 0.1983 0.027 Uiso 1 1 calc GR . . . .
H16B H 0.4688 0.0344 0.1870 0.027 Uiso 1 1 calc GR . . . .
H16C H 0.4128 0.0255 0.0181 0.027 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
P1 C1 1.8826(14) . ?
P1 C4 1.8863(13) . ?
P1 C11 1.8416(14) . ?
O1 C1 1.4538(16) . ?
O1 C2 1.4313(16) . ?
O2 C4 1.4495(15) . ?
O2 C6 1.4315(16) . ?
O3 C2 1.4285(16) . ?
O3 C6 1.4300(16) . ?
N1 C11 1.3472(17) . ?
N1 C15 1.3448(18) . ?
C1 C5 1.5213(19) . ?
C1 C7 1.5121(18) . ?
C2 C3 1.5279(19) . ?
C2 C8 1.5057(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5318(18) . ?
C4 C9 1.5152(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5219(19) . ?
C6 C10 1.5095(19) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.4005(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3903(19) . ?
C13 C14 1.392(2) . ?
C13 C16 1.5033(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 P1 C4 92.79(6) . . ?
C11 P1 C1 106.66(6) . . ?
C11 P1 C4 104.87(6) . . ?
C2 O1 C1 115.39(10) . . ?
C6 O2 C4 115.78(10) . . ?
C2 O3 C6 111.99(10) . . ?
C15 N1 C11 116.81(12) . . ?
O1 C1 P1 104.56(9) . . ?
O1 C1 C5 108.39(10) . . ?
O1 C1 C7 105.55(10) . . ?
C5 C1 P1 113.66(9) . . ?
C7 C1 P1 111.91(10) . . ?
C7 C1 C5 112.09(11) . . ?
O1 C2 C3 111.98(11) . . ?
O1 C2 C8 106.06(11) . . ?
O3 C2 O1 110.63(11) . . ?
O3 C2 C3 107.35(11) . . ?
O3 C2 C8 107.88(11) . . ?
C8 C2 C3 112.90(12) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.19(11) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
O2 C4 P1 113.86(9) . . ?
O2 C4 C3 108.77(10) . . ?
O2 C4 C9 105.08(10) . . ?
C3 C4 P1 103.42(9) . . ?
C9 C4 P1 113.70(9) . . ?
C9 C4 C3 112.10(11) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 C6 110.65(11) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O2 C6 C5 110.80(11) . . ?
O2 C6 C10 106.53(11) . . ?
O3 C6 O2 110.62(10) . . ?
O3 C6 C5 108.07(11) . . ?
O3 C6 C10 107.14(11) . . ?
C10 C6 C5 113.62(11) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 120.33(10) . . ?
N1 C11 C12 122.26(12) . . ?
C12 C11 P1 116.91(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.34(13) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 116.98(13) . . ?
C12 C13 C16 121.35(13) . . ?
C14 C13 C16 121.67(13) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.38(13) . . ?
C15 C14 H14 120.3 . . ?
N1 C15 C14 124.14(13) . . ?
N1 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
P1 C1 C5 C6 63.68(13) . . . . ?
P1 C11 C12 C13 -175.00(10) . . . . ?
O1 C1 C5 C6 -52.10(14) . . . . ?
O1 C2 C3 C4 -63.17(14) . . . . ?
O3 C2 C3 C4 58.44(13) . . . . ?
N1 C11 C12 C13 -3.1(2) . . . . ?
C1 P1 C4 O2 50.80(10) . . . . ?
C1 P1 C4 C3 -67.06(9) . . . . ?
C1 P1 C4 C9 171.12(10) . . . . ?
C1 P1 C11 N1 18.54(12) . . . . ?
C1 P1 C11 C12 -169.43(10) . . . . ?
C1 O1 C2 O3 -55.39(14) . . . . ?
C1 O1 C2 C3 64.31(14) . . . . ?
C1 O1 C2 C8 -172.12(11) . . . . ?
C1 C5 C6 O2 -63.73(14) . . . . ?
C1 C5 C6 O3 57.61(14) . . . . ?
C1 C5 C6 C10 176.38(11) . . . . ?
C2 O1 C1 P1 -69.75(12) . . . . ?
C2 O1 C1 C5 51.80(14) . . . . ?
C2 O1 C1 C7 172.06(11) . . . . ?
C2 O3 C6 O2 60.30(13) . . . . ?
C2 O3 C6 C5 -61.16(13) . . . . ?
C2 O3 C6 C10 176.03(11) . . . . ?
C2 C3 C4 P1 69.52(11) . . . . ?
C2 C3 C4 O2 -51.83(14) . . . . ?
C2 C3 C4 C9 -167.59(11) . . . . ?
C4 P1 C1 O1 65.73(9) . . . . ?
C4 P1 C1 C5 -52.29(10) . . . . ?
C4 P1 C1 C7 179.49(10) . . . . ?
C4 P1 C11 N1 116.13(11) . . . . ?
C4 P1 C11 C12 -71.84(11) . . . . ?
C4 O2 C6 O3 -54.29(14) . . . . ?
C4 O2 C6 C5 65.54(14) . . . . ?
C4 O2 C6 C10 -170.41(10) . . . . ?
C6 O2 C4 P1 -64.18(12) . . . . ?
C6 O2 C4 C3 50.55(14) . . . . ?
C6 O2 C4 C9 170.76(10) . . . . ?
C6 O3 C2 O1 59.69(13) . . . . ?
C6 O3 C2 C3 -62.76(13) . . . . ?
C6 O3 C2 C8 175.29(11) . . . . ?
C7 C1 C5 C6 -168.20(11) . . . . ?
C8 C2 C3 C4 177.20(11) . . . . ?
C11 P1 C1 O1 172.16(8) . . . . ?
C11 P1 C1 C5 54.14(11) . . . . ?
C11 P1 C1 C7 -74.08(11) . . . . ?
C11 P1 C4 O2 -57.26(10) . . . . ?
C11 P1 C4 C3 -175.12(8) . . . . ?
C11 P1 C4 C9 63.06(11) . . . . ?
C11 N1 C15 C14 1.2(2) . . . . ?
C11 C12 C13 C14 2.10(19) . . . . ?
C11 C12 C13 C16 -178.50(12) . . . . ?
C12 C13 C14 C15 0.37(19) . . . . ?
C13 C14 C15 N1 -2.1(2) . . . . ?
C15 N1 C11 P1 173.03(10) . . . . ?
C15 N1 C11 C12 1.44(19) . . . . ?
C16 C13 C14 C15 -179.03(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L5b
_database_code_depnum_ccdc_archive 'CCDC 1497894'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H22 N O3 P'
_chemical_formula_sum            'C16 H22 N O3 P'
_chemical_formula_weight         307.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   8.0709(8)
_cell_length_b                   9.2900(9)
_cell_length_c                   11.0652(10)
_cell_angle_alpha                78.954(7)
_cell_angle_beta                 84.366(7)
_cell_angle_gamma                76.677(7)
_cell_volume                     791.10(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0585 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.8332.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12496
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.982
_diffrn_reflns_theta_min         1.878
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3108
_reflns_number_total             3788
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.035
_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)+(0.0581P)²+0.1989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.47398(5) 0.64919(4) 0.86225(4) 0.01385(12) Uani 1 1 d . . . . .
O1 O 0.34997(14) 0.64119(11) 0.63528(10) 0.0148(2) Uani 1 1 d . . . . .
O2 O 0.54747(14) 0.76910(12) 0.51741(10) 0.0162(2) Uani 1 1 d . . . . .
O3 O 0.66715(14) 0.79777(12) 0.69443(10) 0.0152(2) Uani 1 1 d . . . . .
N1 N 0.23185(17) 0.76249(15) 1.02009(12) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.4717(2) 0.55690(16) 0.72546(14) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.6507(2) 0.54755(17) 0.66264(14) 0.0156(3) Uani 1 1 d . . . . .
H2A H 0.7371 0.5008 0.7243 0.019 Uiso 1 1 calc R . . . .
H2B H 0.6663 0.4837 0.5985 0.019 Uiso 1 1 calc R . . . .
C3 C 0.6762(2) 0.70410(17) 0.60376(14) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.5016(2) 0.83176(17) 0.76146(14) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.3652(2) 0.89142(16) 0.66824(14) 0.0146(3) Uani 1 1 d . . . . .
H5A H 0.3777 0.9916 0.6233 0.017 Uiso 1 1 calc R . . . .
H5B H 0.2511 0.9028 0.7119 0.017 Uiso 1 1 calc R . . . .
C6 C 0.3797(2) 0.78520(16) 0.57676(14) 0.0144(3) Uani 1 1 d . . . . .
C7 C 0.4322(2) 0.40164(17) 0.76278(15) 0.0183(3) Uani 1 1 d . . . . .
H7A H 0.5158 0.3386 0.8201 0.027 Uiso 1 1 calc GR . . . .
H7B H 0.4379 0.3559 0.6893 0.027 Uiso 1 1 calc GR . . . .
H7C H 0.3175 0.4103 0.8030 0.027 Uiso 1 1 calc GR . . . .
C8 C 0.8462(2) 0.70200(19) 0.53313(16) 0.0210(4) Uani 1 1 d . . . . .
H8A H 0.8572 0.6403 0.4690 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.9382 0.6596 0.5897 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.8536 0.8047 0.4948 0.031 Uiso 1 1 calc GR . . . .
C9 C 0.5134(2) 0.94794(18) 0.83805(15) 0.0182(3) Uani 1 1 d . . . . .
H9A H 0.4080 0.9694 0.8897 0.027 Uiso 1 1 calc GR . . . .
H9B H 0.5296 1.0404 0.7832 0.027 Uiso 1 1 calc GR . . . .
H9C H 0.6103 0.9089 0.8907 0.027 Uiso 1 1 calc GR . . . .
C10 C 0.2547(2) 0.84492(18) 0.47716(15) 0.0185(3) Uani 1 1 d . . . . .
H10A H 0.2662 0.7711 0.4227 0.028 Uiso 1 1 calc GR . . . .
H10B H 0.2782 0.9390 0.4291 0.028 Uiso 1 1 calc GR . . . .
H10C H 0.1384 0.8636 0.5148 0.028 Uiso 1 1 calc GR . . . .
C11 C 0.2490(2) 0.69724(17) 0.91868(14) 0.0154(3) Uani 1 1 d . . . . .
C12 C 0.1101(2) 0.66547(18) 0.87130(15) 0.0188(3) Uani 1 1 d . . . . .
H12 H 0.1242 0.6228 0.7985 0.023 Uiso 1 1 calc R . . . .
C13 C -0.0492(2) 0.69718(18) 0.93233(16) 0.0216(4) Uani 1 1 d . . . . .
H13 H -0.1451 0.6734 0.9035 0.026 Uiso 1 1 calc R . . . .
C14 C -0.0663(2) 0.76379(18) 1.03566(16) 0.0214(4) Uani 1 1 d . . . . .
H14 H -0.1743 0.7864 1.0787 0.026 Uiso 1 1 calc R . . . .
C15 C 0.0759(2) 0.79754(17) 1.07613(14) 0.0180(3) Uani 1 1 d . . . . .
C16 C 0.0628(2) 0.8744(2) 1.18564(16) 0.0261(4) Uani 1 1 d . . . . .
H16A H 0.1772 0.8656 1.2129 0.039 Uiso 1 1 calc GR . . . .
H16B H -0.0059 0.8270 1.2529 0.039 Uiso 1 1 calc GR . . . .
H16C H 0.0084 0.9808 1.1625 0.039 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
P1 C1 1.8805(15) . ?
P1 C4 1.8897(16) . ?
P1 C11 1.8429(17) . ?
O1 C1 1.4534(18) . ?
O1 C6 1.4327(18) . ?
O2 C3 1.4291(18) . ?
O2 C6 1.4339(19) . ?
O3 C3 1.4352(18) . ?
O3 C4 1.4612(18) . ?
N1 C11 1.356(2) . ?
N1 C15 1.345(2) . ?
C1 C2 1.532(2) . ?
C1 C7 1.520(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(2) . ?
C3 C8 1.508(2) . ?
C4 C5 1.519(2) . ?
C4 C9 1.518(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.523(2) . ?
C6 C10 1.506(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.396(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(2) . ?
C15 C16 1.504(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 P1 C4 92.61(7) . . ?
C11 P1 C1 105.06(7) . . ?
C11 P1 C4 101.78(7) . . ?
C6 O1 C1 115.12(11) . . ?
C3 O2 C6 111.59(11) . . ?
C3 O3 C4 115.15(11) . . ?
C15 N1 C11 118.73(14) . . ?
O1 C1 P1 114.48(10) . . ?
O1 C1 C2 107.67(12) . . ?
O1 C1 C7 106.57(12) . . ?
C2 C1 P1 104.89(10) . . ?
C7 C1 P1 112.28(11) . . ?
C7 C1 C2 110.90(13) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.39(12) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
O2 C3 O3 110.38(11) . . ?
O2 C3 C2 107.95(12) . . ?
O2 C3 C8 107.01(13) . . ?
O3 C3 C2 111.68(12) . . ?
O3 C3 C8 106.64(13) . . ?
C8 C3 C2 113.09(13) . . ?
O3 C4 P1 105.97(9) . . ?
O3 C4 C5 108.42(12) . . ?
O3 C4 C9 106.16(12) . . ?
C5 C4 P1 112.26(11) . . ?
C9 C4 P1 111.52(11) . . ?
C9 C4 C5 112.09(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.74(12) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O1 C6 O2 110.16(12) . . ?
O1 C6 C5 112.18(12) . . ?
O1 C6 C10 106.70(12) . . ?
O2 C6 C5 107.88(12) . . ?
O2 C6 C10 107.16(12) . . ?
C10 C6 C5 112.65(13) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 111.49(11) . . ?
N1 C11 C12 121.91(15) . . ?
C12 C11 P1 126.51(12) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.90(15) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.01(16) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.45(16) . . ?
C15 C14 H14 120.3 . . ?
N1 C15 C14 121.92(15) . . ?
N1 C15 C16 116.64(15) . . ?
C14 C15 C16 121.43(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
P1 C1 C2 C3 -69.45(13) . . . . ?
P1 C4 C5 C6 -64.74(15) . . . . ?
P1 C11 C12 C13 173.96(12) . . . . ?
O1 C1 C2 C3 52.87(15) . . . . ?
O3 C4 C5 C6 51.98(16) . . . . ?
N1 C11 C12 C13 -2.2(2) . . . . ?
C1 P1 C4 O3 -64.00(10) . . . . ?
C1 P1 C4 C5 54.18(11) . . . . ?
C1 P1 C4 C9 -179.08(11) . . . . ?
C1 P1 C11 N1 178.67(10) . . . . ?
C1 P1 C11 C12 2.20(16) . . . . ?
C1 O1 C6 O2 57.27(15) . . . . ?
C1 O1 C6 C5 -62.92(16) . . . . ?
C1 O1 C6 C10 173.26(12) . . . . ?
C1 C2 C3 O2 -58.06(15) . . . . ?
C1 C2 C3 O3 63.45(16) . . . . ?
C1 C2 C3 C8 -176.26(13) . . . . ?
C3 O2 C6 O1 -60.75(14) . . . . ?
C3 O2 C6 C5 62.00(14) . . . . ?
C3 O2 C6 C10 -176.46(11) . . . . ?
C3 O3 C4 P1 69.05(13) . . . . ?
C3 O3 C4 C5 -51.65(15) . . . . ?
C3 O3 C4 C9 -172.26(12) . . . . ?
C4 P1 C1 O1 -52.39(12) . . . . ?
C4 P1 C1 C2 65.39(10) . . . . ?
C4 P1 C1 C7 -174.08(12) . . . . ?
C4 P1 C11 N1 -85.34(12) . . . . ?
C4 P1 C11 C12 98.19(15) . . . . ?
C4 O3 C3 O2 55.82(16) . . . . ?
C4 O3 C3 C2 -64.28(16) . . . . ?
C4 O3 C3 C8 171.72(12) . . . . ?
C4 C5 C6 O1 63.54(17) . . . . ?
C4 C5 C6 O2 -57.97(16) . . . . ?
C4 C5 C6 C10 -176.03(13) . . . . ?
C6 O1 C1 P1 62.80(15) . . . . ?
C6 O1 C1 C2 -53.40(15) . . . . ?
C6 O1 C1 C7 -172.44(12) . . . . ?
C6 O2 C3 O3 -60.68(15) . . . . ?
C6 O2 C3 C2 61.64(14) . . . . ?
C6 O2 C3 C8 -176.34(11) . . . . ?
C7 C1 C2 C3 169.11(13) . . . . ?
C9 C4 C5 C6 168.83(13) . . . . ?
C11 P1 C1 O1 50.55(12) . . . . ?
C11 P1 C1 C2 168.33(9) . . . . ?
C11 P1 C1 C7 -71.14(12) . . . . ?
C11 P1 C4 O3 -169.98(9) . . . . ?
C11 P1 C4 C5 -51.80(12) . . . . ?
C11 P1 C4 C9 74.94(12) . . . . ?
C11 N1 C15 C14 2.4(2) . . . . ?
C11 N1 C15 C16 -178.00(14) . . . . ?
C11 C12 C13 C14 2.1(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 N1 -2.4(2) . . . . ?
C13 C14 C15 C16 178.05(15) . . . . ?
C15 N1 C11 P1 -176.75(11) . . . . ?
C15 N1 C11 C12 -0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L6a
_database_code_depnum_ccdc_archive 'CCDC 1497895'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2014-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H19 F3 N O3 P'
_chemical_formula_sum            'C16 H19 F3 N O3 P'
_chemical_formula_weight         361.29
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5819(9)
_cell_length_b                   10.5008(12)
_cell_length_c                   22.185(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.305(5)
_cell_angle_gamma                90
_cell_volume                     1743.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    170
_cell_measurement_theta_max      66.523
_cell_measurement_theta_min      4.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1339 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.4874.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33931
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.809
_diffrn_reflns_theta_min         4.038
_diffrn_ambient_temperature      170
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2849
_reflns_number_total             3071
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.224
_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)+(0.0509P)²+1.2866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1133
_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
 O1-C2 \\sim O1A-C2
 with sigma of 0.01
 O1A-C1 \\sim O1-C1
 with sigma of 0.01
 C7-C1 \\sim C7A-C1
 with sigma of 0.01
 F1A-C16 \\sim F2-C16 \\sim F2A-C16 \\sim F3-C16 \\sim F3A-C16 \\sim F1-C16
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C7 \\sim C7A: within 1.7A with sigma of 0.003 and sigma for terminal atoms of
0.006
F1A \\sim F1 \\sim F2 \\sim F2A \\sim F3 \\sim F3A: within 1.7A with sigma of
0.004 and sigma for terminal atoms of 0.008
Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
4. Others
 Fixed Sof: F1(0.42486) F2(0.42486) F3(0.42486) O1(0.50062) C7(0.50062)
 H7A(0.50062) H7B(0.50062) H7C(0.50062) F1A(0.57514) F2A(0.57514) F3A(0.57514)
 C7A(0.49938) H7AA(0.49938) H7AB(0.49938) H7AC(0.49938) O1A(0.49938)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C7A(H7AA,H7AB,H7AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.43877(7) 0.14594(5) 0.66427(2) 0.04170(18) Uani 1 1 d . . . . .
F1 F 0.3815(7) 0.6468(7) 0.5845(3) 0.087(2) Uani 0.4249 1 d . . P A 1
F2 F 0.6094(12) 0.6021(6) 0.5506(2) 0.1029(18) Uani 0.4249 1 d . . P A 1
F3 F 0.6045(13) 0.7390(6) 0.6244(5) 0.086(3) Uani 0.4249 1 d . . P A 1
O1 O 0.0965(5) 0.0524(4) 0.6737(2) 0.0397(12) Uani 0.5006 1 d . U P B 1
O2 O -0.03586(17) 0.11588(14) 0.58208(7) 0.0440(4) Uani 1 1 d . . . . .
O3 O 0.20945(15) 0.23266(11) 0.56111(5) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.6367(2) 0.32139(16) 0.72863(7) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.2143(4) 0.1591(3) 0.68975(10) 0.0595(8) Uani 1 1 d . . . . .
C2 C 0.0756(3) 0.0156(2) 0.60964(9) 0.0458(5) Uani 1 1 d . . . . .
C3 C 0.2373(3) 0.00703(18) 0.57729(9) 0.0377(5) Uani 1 1 d . . . . .
H3A H 0.1981 -0.0147 0.5338 0.045 Uiso 1 1 calc R . . . .
H3B H 0.3183 -0.0611 0.5961 0.045 Uiso 1 1 calc R . . . .
C4 C 0.3368(2) 0.13420(16) 0.58211(8) 0.0289(4) Uani 1 1 d . . . . .
C5 C 0.0999(3) 0.2646(3) 0.65682(11) 0.0561(7) Uani 1 1 d . . . . .
H5A H -0.0116 0.2730 0.6744 0.067 Uiso 1 1 calc R . . . .
H5B H 0.1653 0.3464 0.6628 0.067 Uiso 1 1 calc R . . . .
C6 C 0.0538(2) 0.23605(19) 0.58903(10) 0.0394(5) Uani 1 1 d . . . . .
C7 C 0.1994(13) 0.1931(10) 0.7571(3) 0.064(2) Uani 0.5006 1 d . . P B 1
H7A H 0.2506 0.1240 0.7841 0.096 Uiso 0.5006 1 calc GR . P B 1
H7B H 0.0734 0.2046 0.7609 0.096 Uiso 0.5006 1 calc GR . P B 1
H7C H 0.2650 0.2722 0.7687 0.096 Uiso 0.5006 1 calc GR . P B 1
C8 C -0.0357(4) -0.1046(3) 0.60388(11) 0.0671(8) Uani 1 1 d . . . . .
H8A H 0.0358 -0.1752 0.6238 0.101 Uiso 1 1 calc GR . . . .
H8B H -0.0736 -0.1247 0.5606 0.101 Uiso 1 1 calc GR . . . .
H8C H -0.1412 -0.0920 0.6235 0.101 Uiso 1 1 calc GR . . . .
C9 C 0.4770(3) 0.1417(2) 0.54086(11) 0.0453(5) Uani 1 1 d . . . . .
H9A H 0.5309 0.2267 0.5438 0.068 Uiso 1 1 calc GR . . . .
H9B H 0.4212 0.1254 0.4986 0.068 Uiso 1 1 calc GR . . . .
H9C H 0.5697 0.0777 0.5535 0.068 Uiso 1 1 calc GR . . . .
C10 C -0.0675(3) 0.3331(2) 0.55357(16) 0.0700(8) Uani 1 1 d . . . . .
H10A H -0.0973 0.3059 0.5109 0.105 Uiso 1 1 calc GR . . . .
H10B H -0.0067 0.4157 0.5555 0.105 Uiso 1 1 calc GR . . . .
H10C H -0.1773 0.3409 0.5713 0.105 Uiso 1 1 calc GR . . . .
C11 C 0.5265(2) 0.30893(17) 0.67464(8) 0.0296(4) Uani 1 1 d . . . . .
C12 C 0.4965(2) 0.40762(17) 0.63267(8) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.4170 0.3970 0.5953 0.035 Uiso 1 1 calc R . . . .
C13 C 0.5847(2) 0.52183(17) 0.64647(8) 0.0313(4) Uani 1 1 d . . . . .
C14 C 0.6980(3) 0.53619(18) 0.70165(9) 0.0363(4) Uani 1 1 d . . . . .
H14 H 0.7604 0.6136 0.7120 0.044 Uiso 1 1 calc R . . . .
C15 C 0.7166(3) 0.43365(19) 0.74104(9) 0.0394(5) Uani 1 1 d . . . . .
H15 H 0.7912 0.4436 0.7795 0.047 Uiso 1 1 calc R . . . .
C16 C 0.5595(3) 0.62813(19) 0.60108(10) 0.0486(5) Uani 1 1 d . . . . .
F1A F 0.4227(8) 0.6169(6) 0.5573(2) 0.109(2) Uani 0.5751 1 d . . P A 2
F2A F 0.7056(5) 0.6367(4) 0.57224(19) 0.0788(11) Uani 0.5751 1 d . . P A 2
F3A F 0.5592(10) 0.7408(5) 0.6257(4) 0.0777(17) Uani 0.5751 1 d . . P A 2
C7A C 0.2686(12) 0.1482(10) 0.7603(2) 0.060(2) Uani 0.4994 1 d . . P B 2
H7AA H 0.3421 0.0719 0.7702 0.090 Uiso 0.4994 1 calc GR . P B 2
H7AB H 0.1608 0.1420 0.7792 0.090 Uiso 0.4994 1 calc GR . P B 2
H7AC H 0.3370 0.2238 0.7758 0.090 Uiso 0.4994 1 calc GR . P B 2
O1A O 0.1555(6) 0.0240(4) 0.6739(2) 0.0374(11) Uani 0.4994 1 d . U P B 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 C1 1.883(3) . ?
P1 C4 1.8655(18) . ?
P1 C11 1.8372(18) . ?
F1 C16 1.354(5) . ?
F2 C16 1.269(5) . ?
F3 C16 1.298(5) . ?
O1 C1 1.441(4) . ?
O1 C2 1.456(5) . ?
O2 C2 1.424(3) . ?
O2 C6 1.430(2) . ?
O3 C4 1.440(2) . ?
O3 C6 1.419(2) . ?
N1 C11 1.351(2) . ?
N1 C15 1.334(3) . ?
C1 C5 1.519(4) . ?
C1 C7 1.558(6) . ?
C1 C7A 1.556(6) . ?
C1 O1A 1.512(5) . ?
C2 C3 1.520(3) . ?
C2 C8 1.512(3) . ?
C2 O1A 1.458(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.529(2) . ?
C4 C9 1.513(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.518(3) . ?
C6 C10 1.507(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 C14 1.385(3) . ?
C13 C16 1.495(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9500 . ?
C16 F1A 1.307(4) . ?
C16 F2A 1.369(4) . ?
C16 F3A 1.303(4) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?

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
C4 P1 C1 92.65(9) . . ?
C11 P1 C1 102.74(10) . . ?
C11 P1 C4 105.57(8) . . ?
C1 O1 C2 114.4(3) . . ?
C2 O2 C6 111.55(14) . . ?
C6 O3 C4 115.99(14) . . ?
C15 N1 C11 117.63(16) . . ?
O1 C1 P1 115.0(3) . . ?
O1 C1 C5 99.5(3) . . ?
O1 C1 C7 106.1(5) . . ?
C5 C1 P1 112.50(14) . . ?
C5 C1 C7 99.8(4) . . ?
C5 C1 C7A 125.1(4) . . ?
C7 C1 P1 120.9(4) . . ?
C7A C1 P1 101.0(4) . . ?
O1A C1 P1 96.2(2) . . ?
O1A C1 C5 116.6(2) . . ?
O1A C1 C7A 100.7(5) . . ?
O1 C2 C3 120.5(2) . . ?
O1 C2 C8 106.0(2) . . ?
O2 C2 O1 100.7(3) . . ?
O2 C2 C3 108.00(15) . . ?
O2 C2 C8 107.27(18) . . ?
O2 C2 O1A 119.9(2) . . ?
C8 C2 C3 113.1(2) . . ?
O1A C2 C3 103.0(2) . . ?
O1A C2 C8 105.7(2) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C2 C3 C4 109.97(16) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
O3 C4 P1 114.77(12) . . ?
O3 C4 C3 107.90(13) . . ?
O3 C4 C9 105.49(15) . . ?
C3 C4 P1 104.35(12) . . ?
C9 C4 P1 111.51(13) . . ?
C9 C4 C3 112.96(16) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C1 110.78(19) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O2 C6 C5 108.07(18) . . ?
O2 C6 C10 107.55(16) . . ?
O3 C6 O2 110.20(15) . . ?
O3 C6 C5 111.29(15) . . ?
O3 C6 C10 105.63(19) . . ?
C10 C6 C5 114.0(2) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 111.14(13) . . ?
N1 C11 C12 122.24(16) . . ?
C12 C11 P1 126.52(13) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.56(16) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C14 119.91(17) . . ?
C12 C13 C16 119.58(16) . . ?
C14 C13 C16 120.50(17) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.40(17) . . ?
C15 C14 H14 121.3 . . ?
N1 C15 C14 124.23(17) . . ?
N1 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
F1 C16 C13 107.7(3) . . ?
F2 C16 F1 102.6(5) . . ?
F2 C16 F3 116.7(7) . . ?
F2 C16 C13 114.2(3) . . ?
F3 C16 F1 99.5(6) . . ?
F3 C16 C13 113.8(5) . . ?
F1A C16 C13 115.7(3) . . ?
F1A C16 F2A 105.3(4) . . ?
F2A C16 C13 109.8(2) . . ?
F3A C16 C13 113.9(4) . . ?
F3A C16 F1A 109.8(5) . . ?
F3A C16 F2A 101.1(4) . . ?
C1 C7A H7AA 109.5 . . ?
C1 C7A H7AB 109.5 . . ?
C1 C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C2 O1A C1 110.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C5 C6 64.39(19) . . . . ?
P1 C1 O1A C2 -84.9(3) . . . . ?
P1 C11 C12 C13 -175.10(14) . . . . ?
O1 C1 C5 C6 -57.8(3) . . . . ?
O1 C1 O1A C2 70.8(8) . . . . ?
O1 C2 C3 C4 -56.4(3) . . . . ?
O1 C2 O1A C1 -66.2(8) . . . . ?
O2 C2 C3 C4 58.32(18) . . . . ?
O2 C2 O1A C1 -38.9(4) . . . . ?
N1 C11 C12 C13 1.0(3) . . . . ?
C1 P1 C4 O3 51.38(14) . . . . ?
C1 P1 C4 C3 -66.49(14) . . . . ?
C1 P1 C4 C9 171.25(15) . . . . ?
C1 P1 C11 N1 96.71(15) . . . . ?
C1 P1 C11 C12 -86.87(18) . . . . ?
C1 O1 C2 O2 -74.1(4) . . . . ?
C1 O1 C2 C3 44.3(5) . . . . ?
C1 O1 C2 C8 174.2(3) . . . . ?
C1 O1 C2 O1A 82.0(8) . . . . ?
C1 C5 C6 O2 57.6(2) . . . . ?
C1 C5 C6 O3 -63.6(2) . . . . ?
C1 C5 C6 C10 177.07(18) . . . . ?
C2 O1 C1 P1 -50.4(4) . . . . ?
C2 O1 C1 C5 70.0(4) . . . . ?
C2 O1 C1 C7 173.1(4) . . . . ?
C2 O1 C1 C7A -160.0(4) . . . . ?
C2 O1 C1 O1A -77.3(9) . . . . ?
C2 O2 C6 O3 60.1(2) . . . . ?
C2 O2 C6 C5 -61.7(2) . . . . ?
C2 O2 C6 C10 174.75(19) . . . . ?
C2 C3 C4 P1 70.01(16) . . . . ?
C2 C3 C4 O3 -52.48(19) . . . . ?
C2 C3 C4 C9 -168.69(16) . . . . ?
C3 C2 O1A C1 81.1(3) . . . . ?
C4 P1 C1 O1 59.8(3) . . . . ?
C4 P1 C1 C5 -53.13(16) . . . . ?
C4 P1 C1 C7 -170.7(5) . . . . ?
C4 P1 C1 C7A 171.3(4) . . . . ?
C4 P1 C1 O1A 69.1(2) . . . . ?
C4 P1 C11 N1 -166.84(13) . . . . ?
C4 P1 C11 C12 9.58(19) . . . . ?
C4 O3 C6 O2 -56.3(2) . . . . ?
C4 O3 C6 C5 63.6(2) . . . . ?
C4 O3 C6 C10 -172.18(16) . . . . ?
C5 C1 O1A C2 34.1(4) . . . . ?
C6 O2 C2 O1 65.2(2) . . . . ?
C6 O2 C2 C3 -62.0(2) . . . . ?
C6 O2 C2 C8 175.87(18) . . . . ?
C6 O2 C2 O1A 55.5(3) . . . . ?
C6 O3 C4 P1 -63.11(16) . . . . ?
C6 O3 C4 C3 52.73(19) . . . . ?
C6 O3 C4 C9 173.72(14) . . . . ?
C7 C1 C5 C6 -166.1(4) . . . . ?
C7 C1 O1A C2 148.1(4) . . . . ?
C8 C2 C3 C4 176.85(17) . . . . ?
C8 C2 O1A C1 -160.1(3) . . . . ?
C11 P1 C1 O1 166.4(3) . . . . ?
C11 P1 C1 C5 53.49(16) . . . . ?
C11 P1 C1 C7 -64.1(5) . . . . ?
C11 P1 C1 C7A -82.1(4) . . . . ?
C11 P1 C1 O1A 175.69(19) . . . . ?
C11 P1 C4 O3 -52.63(14) . . . . ?
C11 P1 C4 C3 -170.51(12) . . . . ?
C11 P1 C4 C9 67.24(14) . . . . ?
C11 N1 C15 C14 -2.0(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C11 C12 C13 C16 177.89(18) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C12 C13 C16 F1 52.0(4) . . . . ?
C12 C13 C16 F2 -61.2(5) . . . . ?
C12 C13 C16 F3 161.3(6) . . . . ?
C12 C13 C16 F1A 15.8(5) . . . . ?
C12 C13 C16 F2A -103.1(3) . . . . ?
C12 C13 C16 F3A 144.4(4) . . . . ?
C13 C14 C15 N1 1.9(3) . . . . ?
C14 C13 C16 F1 -129.1(4) . . . . ?
C14 C13 C16 F2 117.7(5) . . . . ?
C14 C13 C16 F3 -19.8(6) . . . . ?
C14 C13 C16 F1A -165.3(4) . . . . ?
C14 C13 C16 F2A 75.8(3) . . . . ?
C14 C13 C16 F3A -36.7(4) . . . . ?
C15 N1 C11 P1 177.08(15) . . . . ?
C15 N1 C11 C12 0.5(3) . . . . ?
C16 C13 C14 C15 -179.21(19) . . . . ?
C7A C1 C5 C6 -172.6(5) . . . . ?
C7A C1 O1A C2 172.6(4) . . . . ?
O1A C1 C5 C6 -45.4(3) . . . . ?
O1A C2 C3 C4 -69.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L6b
_database_code_depnum_ccdc_archive 'CCDC 1497896'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H19 F3 N O3 P'
_chemical_formula_sum            'C16 H19 F3 N O3 P'
_chemical_formula_weight         361.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   35.1058(14)
_cell_length_b                   7.3422(3)
_cell_length_c                   13.5142(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.839(3)
_cell_angle_gamma                90
_cell_volume                     3351.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5917
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0504 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.8733.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.930
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3417
_reflns_number_total             4011
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.034
_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)+(0.0421P)²+2.4527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0862
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.61226(2) 0.75122(4) 0.48991(2) 0.01530(9) Uani 1 1 d . . . . .
F1 F 0.76745(3) 1.07935(15) 0.75918(8) 0.0469(3) Uani 1 1 d . . . . .
F2 F 0.73585(3) 1.18803(16) 0.61391(9) 0.0574(3) Uani 1 1 d . . . . .
F3 F 0.75608(3) 0.91204(17) 0.62550(11) 0.0661(4) Uani 1 1 d . . . . .
O1 O 0.56863(2) 0.55810(11) 0.60087(6) 0.01411(18) Uani 1 1 d . . . . .
O2 O 0.60723(2) 0.41321(12) 0.41045(6) 0.01608(18) Uani 1 1 d . . . . .
O3 O 0.56880(3) 0.28518(11) 0.51078(6) 0.01495(18) Uani 1 1 d . . . . .
N1 N 0.67622(3) 0.91135(15) 0.60502(9) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.56434(3) 0.67159(16) 0.51067(9) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.54497(4) 0.55546(17) 0.41579(9) 0.0161(2) Uani 1 1 d . . . . .
H2A H 0.5173 0.5271 0.4150 0.019 Uiso 1 1 calc R . . . .
H2B H 0.5444 0.6247 0.3526 0.019 Uiso 1 1 calc R . . . .
C3 C 0.56801(4) 0.37857(17) 0.41752(9) 0.0151(2) Uani 1 1 d . . . . .
C4 C 0.63276(3) 0.51174(17) 0.49666(9) 0.0159(2) Uani 1 1 d . . . . .
C5 C 0.63138(4) 0.41525(17) 0.59559(9) 0.0161(2) Uani 1 1 d . . . . .
H5A H 0.6445 0.2951 0.5994 0.019 Uiso 1 1 calc R . . . .
H5B H 0.6460 0.4882 0.6556 0.019 Uiso 1 1 calc R . . . .
C6 C 0.58877(4) 0.38904(16) 0.59936(9) 0.0143(2) Uani 1 1 d . . . . .
C7 C 0.53808(4) 0.83014(17) 0.52206(10) 0.0196(3) Uani 1 1 d . . . . .
H7A H 0.5503 0.8955 0.5861 0.029 Uiso 1 1 calc GR . . . .
H7B H 0.5121 0.7841 0.5239 0.029 Uiso 1 1 calc GR . . . .
H7C H 0.5349 0.9132 0.4636 0.029 Uiso 1 1 calc GR . . . .
C8 C 0.54967(4) 0.24994(19) 0.33092(9) 0.0201(3) Uani 1 1 d . . . . .
H8A H 0.5478 0.3098 0.2650 0.030 Uiso 1 1 calc GR . . . .
H8B H 0.5231 0.2157 0.3345 0.030 Uiso 1 1 calc GR . . . .
H8C H 0.5661 0.1405 0.3369 0.030 Uiso 1 1 calc GR . . . .
C9 C 0.67336(4) 0.51104(19) 0.47803(11) 0.0225(3) Uani 1 1 d . . . . .
H9A H 0.6718 0.5662 0.4110 0.034 Uiso 1 1 calc GR . . . .
H9B H 0.6828 0.3854 0.4789 0.034 Uiso 1 1 calc GR . . . .
H9C H 0.6918 0.5812 0.5322 0.034 Uiso 1 1 calc GR . . . .
C10 C 0.58498(4) 0.28543(18) 0.69234(9) 0.0204(3) Uani 1 1 d . . . . .
H10A H 0.5972 0.3556 0.7546 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.5984 0.1676 0.6956 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.5569 0.2656 0.6873 0.031 Uiso 1 1 calc GR . . . .
C11 C 0.64210(4) 0.83983(16) 0.61481(10) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.63324(4) 0.83565(17) 0.70978(10) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.6094 0.7810 0.7156 0.023 Uiso 1 1 calc R . . . .
C13 C 0.65961(4) 0.91217(18) 0.79531(10) 0.0227(3) Uani 1 1 d . . . . .
H13 H 0.6535 0.9150 0.8596 0.027 Uiso 1 1 calc R . . . .
C14 C 0.69491(4) 0.98451(18) 0.78590(11) 0.0237(3) Uani 1 1 d . . . . .
H14 H 0.7136 1.0373 0.8431 0.028 Uiso 1 1 calc R . . . .
C15 C 0.70182(4) 0.97680(17) 0.68980(11) 0.0214(3) Uani 1 1 d . . . . .
C16 C 0.74018(4) 1.0396(2) 0.67214(13) 0.0309(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.8730(12) . ?
P1 C4 1.8927(13) . ?
P1 C11 1.8451(13) . ?
F1 C16 1.3306(18) . ?
F2 C16 1.3286(18) . ?
F3 C16 1.3332(19) . ?
O1 C1 1.4501(14) . ?
O1 C6 1.4314(14) . ?
O2 C3 1.4287(14) . ?
O2 C4 1.4540(14) . ?
O3 C3 1.4284(14) . ?
O3 C6 1.4310(14) . ?
N1 C11 1.3468(16) . ?
N1 C15 1.3377(17) . ?
C1 C2 1.5354(17) . ?
C1 C7 1.5186(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5269(17) . ?
C3 C8 1.5050(17) . ?
C4 C5 1.5254(17) . ?
C4 C9 1.5136(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5229(17) . ?
C6 C10 1.5054(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.4011(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3872(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 C16 1.5029(19) . ?

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
C1 P1 C4 92.76(5) . . ?
C11 P1 C1 106.38(5) . . ?
C11 P1 C4 99.79(5) . . ?
C6 O1 C1 115.13(8) . . ?
C3 O2 C4 115.44(9) . . ?
C3 O3 C6 111.69(9) . . ?
C15 N1 C11 117.61(11) . . ?
O1 C1 P1 114.45(8) . . ?
O1 C1 C2 107.67(9) . . ?
O1 C1 C7 106.37(9) . . ?
C2 C1 P1 105.03(8) . . ?
C7 C1 P1 111.77(8) . . ?
C7 C1 C2 111.57(10) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.34(10) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
O2 C3 C2 111.33(10) . . ?
O2 C3 C8 105.98(9) . . ?
O3 C3 O2 110.94(9) . . ?
O3 C3 C2 107.72(9) . . ?
O3 C3 C8 106.63(10) . . ?
C8 C3 C2 114.17(10) . . ?
O2 C4 P1 106.29(8) . . ?
O2 C4 C5 108.13(9) . . ?
O2 C4 C9 105.52(9) . . ?
C5 C4 P1 111.78(8) . . ?
C9 C4 P1 110.98(9) . . ?
C9 C4 C5 113.63(10) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.77(10) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O1 C6 C5 112.61(10) . . ?
O1 C6 C10 105.65(9) . . ?
O3 C6 O1 110.05(9) . . ?
O3 C6 C5 107.49(9) . . ?
O3 C6 C10 107.11(10) . . ?
C10 C6 C5 113.78(10) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 110.22(9) . . ?
N1 C11 C12 121.62(12) . . ?
C12 C11 P1 128.14(10) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.33(12) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.27(13) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.38(12) . . ?
C15 C14 H14 121.3 . . ?
N1 C15 C14 124.67(12) . . ?
N1 C15 C16 113.32(12) . . ?
C14 C15 C16 121.99(13) . . ?
F1 C16 F3 106.21(13) . . ?
F1 C16 C15 112.74(13) . . ?
F2 C16 F1 106.37(12) . . ?
F2 C16 F3 106.93(14) . . ?
F2 C16 C15 112.52(12) . . ?
F3 C16 C15 111.63(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 69.57(10) . . . . ?
P1 C4 C5 C6 64.29(11) . . . . ?
P1 C11 C12 C13 -179.26(10) . . . . ?
O1 C1 C2 C3 -52.80(12) . . . . ?
O2 C4 C5 C6 -52.36(12) . . . . ?
N1 C11 C12 C13 2.10(19) . . . . ?
N1 C15 C16 F1 -170.82(12) . . . . ?
N1 C15 C16 F2 68.87(17) . . . . ?
N1 C15 C16 F3 -51.36(17) . . . . ?
C1 P1 C4 O2 63.27(8) . . . . ?
C1 P1 C4 C5 -54.49(9) . . . . ?
C1 P1 C4 C9 177.52(9) . . . . ?
C1 P1 C11 N1 -175.93(8) . . . . ?
C1 P1 C11 C12 5.30(13) . . . . ?
C1 O1 C6 O3 -57.47(12) . . . . ?
C1 O1 C6 C5 62.45(12) . . . . ?
C1 O1 C6 C10 -172.78(9) . . . . ?
C1 C2 C3 O2 -63.87(12) . . . . ?
C1 C2 C3 O3 57.97(12) . . . . ?
C1 C2 C3 C8 176.18(10) . . . . ?
C3 O2 C4 P1 -68.86(10) . . . . ?
C3 O2 C4 C5 51.30(13) . . . . ?
C3 O2 C4 C9 173.21(10) . . . . ?
C3 O3 C6 O1 61.15(12) . . . . ?
C3 O3 C6 C5 -61.82(12) . . . . ?
C3 O3 C6 C10 175.54(10) . . . . ?
C4 P1 C1 O1 53.17(9) . . . . ?
C4 P1 C1 C2 -64.70(8) . . . . ?
C4 P1 C1 C7 174.16(9) . . . . ?
C4 P1 C11 N1 88.24(9) . . . . ?
C4 P1 C11 C12 -90.53(12) . . . . ?
C4 O2 C3 O3 -55.22(13) . . . . ?
C4 O2 C3 C2 64.73(12) . . . . ?
C4 O2 C3 C8 -170.58(10) . . . . ?
C4 C5 C6 O1 -62.95(12) . . . . ?
C4 C5 C6 O3 58.44(12) . . . . ?
C4 C5 C6 C10 176.86(10) . . . . ?
C6 O1 C1 P1 -62.97(11) . . . . ?
C6 O1 C1 C2 53.39(12) . . . . ?
C6 O1 C1 C7 173.11(9) . . . . ?
C6 O3 C3 O2 60.15(12) . . . . ?
C6 O3 C3 C2 -61.93(12) . . . . ?
C6 O3 C3 C8 175.11(9) . . . . ?
C7 C1 C2 C3 -169.16(10) . . . . ?
C9 C4 C5 C6 -169.14(10) . . . . ?
C11 P1 C1 O1 -47.88(9) . . . . ?
C11 P1 C1 C2 -165.74(8) . . . . ?
C11 P1 C1 C7 73.12(9) . . . . ?
C11 P1 C4 O2 170.42(7) . . . . ?
C11 P1 C4 C5 52.65(9) . . . . ?
C11 P1 C4 C9 -75.34(9) . . . . ?
C11 N1 C15 C14 -3.38(19) . . . . ?
C11 N1 C15 C16 175.39(11) . . . . ?
C11 C12 C13 C14 -2.61(19) . . . . ?
C12 C13 C14 C15 0.32(19) . . . . ?
C13 C14 C15 N1 2.8(2) . . . . ?
C13 C14 C15 C16 -175.85(12) . . . . ?
C14 C15 C16 F1 8.0(2) . . . . ?
C14 C15 C16 F2 -112.33(16) . . . . ?
C14 C15 C16 F3 127.45(15) . . . . ?
C15 N1 C11 P1 -178.04(9) . . . . ?
C15 N1 C11 C12 0.82(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L7a
_database_code_depnum_ccdc_archive 'CCDC 1497897'
_audit_update_record             
;
2016-09-15 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_audit_creation_date             2016-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H28 N O3 P Si'
_chemical_formula_sum            'C18 H28 N O3 P Si'
_chemical_formula_weight         365.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2174(4)
_cell_length_b                   11.5325(5)
_cell_length_c                   18.7960(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.645(2)
_cell_angle_gamma                90
_cell_volume                     1969.77(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.869
_cell_measurement_theta_min      2.198
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0438 before and 0.0365 after correction.
The Ratio of minimum to maximum transmission is 0.9067.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16282
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         2.080
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3777
_reflns_number_total             4336
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.047
_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)+(0.0345P)²+0.9448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.32762(4) 0.53061(3) 0.20935(2) 0.01335(9) Uani 1 1 d . . . . .
Si1 Si -0.08286(4) 0.37404(3) 0.38483(2) 0.01603(10) Uani 1 1 d . . . . .
O1 O 0.39352(10) 0.43407(8) 0.08806(5) 0.0158(2) Uani 1 1 d . . . . .
O2 O 0.05830(10) 0.43902(8) 0.13987(5) 0.01272(19) Uani 1 1 d . . . . .
O3 O 0.15467(10) 0.37042(8) 0.03968(5) 0.01450(19) Uani 1 1 d . . . . .
N1 N 0.39947(12) 0.46001(9) 0.34603(6) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.38211(14) 0.39777(11) 0.16101(7) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.26607(14) 0.30304(11) 0.15656(7) 0.0147(3) Uani 1 1 d . . . . .
H2A H 0.2476 0.2844 0.2057 0.018 Uiso 1 1 calc R . . . .
H2B H 0.3026 0.2320 0.1358 0.018 Uiso 1 1 calc R . . . .
C3 C 0.12242(15) 0.34181(11) 0.10965(7) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.14716(14) 0.54382(11) 0.14658(7) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.18829(14) 0.57017(11) 0.07257(7) 0.0141(3) Uani 1 1 d . . . . .
H5A H 0.0990 0.5932 0.0385 0.017 Uiso 1 1 calc R . . . .
H5B H 0.2586 0.6357 0.0769 0.017 Uiso 1 1 calc R . . . .
C6 C 0.25731(14) 0.46448(11) 0.04334(7) 0.0144(3) Uani 1 1 d . . . . .
C7 C 0.53529(15) 0.35734(13) 0.19408(7) 0.0204(3) Uani 1 1 d . . . . .
H7A H 0.6066 0.4188 0.1896 0.031 Uiso 1 1 calc GR . . . .
H7B H 0.5606 0.2878 0.1688 0.031 Uiso 1 1 calc GR . . . .
H7C H 0.5377 0.3393 0.2452 0.031 Uiso 1 1 calc GR . . . .
C8 C 0.00625(16) 0.24819(12) 0.09959(7) 0.0192(3) Uani 1 1 d . . . . .
H8A H -0.0156 0.2247 0.1468 0.029 Uiso 1 1 calc GR . . . .
H8B H 0.0423 0.1812 0.0757 0.029 Uiso 1 1 calc GR . . . .
H8C H -0.0834 0.2780 0.0698 0.029 Uiso 1 1 calc GR . . . .
C9 C 0.05146(15) 0.63994(11) 0.16888(7) 0.0174(3) Uani 1 1 d . . . . .
H9A H 0.0224 0.6202 0.2152 0.026 Uiso 1 1 calc GR . . . .
H9B H -0.0367 0.6489 0.1321 0.026 Uiso 1 1 calc GR . . . .
H9C H 0.1069 0.7128 0.1737 0.026 Uiso 1 1 calc GR . . . .
C10 C 0.29122(16) 0.48339(12) -0.03178(7) 0.0186(3) Uani 1 1 d . . . . .
H10A H 0.3631 0.5463 -0.0308 0.028 Uiso 1 1 calc GR . . . .
H10B H 0.2006 0.5042 -0.0645 0.028 Uiso 1 1 calc GR . . . .
H10C H 0.3319 0.4120 -0.0488 0.028 Uiso 1 1 calc GR . . . .
C11 C 0.28045(15) 0.46878(11) 0.29320(7) 0.0136(3) Uani 1 1 d . . . . .
C12 C 0.13932(14) 0.44092(11) 0.30518(7) 0.0153(3) Uani 1 1 d . . . . .
H12 H 0.0592 0.4452 0.2663 0.018 Uiso 1 1 calc R . . . .
C13 C 0.11338(15) 0.40676(11) 0.37350(7) 0.0152(3) Uani 1 1 d . . . . .
C14 C 0.23771(15) 0.39890(11) 0.42747(7) 0.0167(3) Uani 1 1 d . . . . .
H14 H 0.2277 0.3767 0.4751 0.020 Uiso 1 1 calc R . . . .
C15 C 0.37591(15) 0.42383(12) 0.41092(7) 0.0171(3) Uani 1 1 d . . . . .
H15 H 0.4589 0.4146 0.4480 0.021 Uiso 1 1 calc R . . . .
C16 C -0.14637(16) 0.25111(13) 0.32303(7) 0.0210(3) Uani 1 1 d . . . . .
H16A H -0.1424 0.2739 0.2732 0.032 Uiso 1 1 calc GR . . . .
H16B H -0.2477 0.2308 0.3274 0.032 Uiso 1 1 calc GR . . . .
H16C H -0.0823 0.1839 0.3360 0.032 Uiso 1 1 calc GR . . . .
C17 C -0.19619(16) 0.50576(13) 0.35704(8) 0.0246(3) Uani 1 1 d . . . . .
H17A H -0.1611 0.5703 0.3893 0.037 Uiso 1 1 calc GR . . . .
H17B H -0.2995 0.4897 0.3599 0.037 Uiso 1 1 calc GR . . . .
H17C H -0.1875 0.5264 0.3074 0.037 Uiso 1 1 calc GR . . . .
C18 C -0.08919(17) 0.33583(13) 0.48079(7) 0.0233(3) Uani 1 1 d . . . . .
H18A H -0.0217 0.2713 0.4956 0.035 Uiso 1 1 calc GR . . . .
H18B H -0.1896 0.3130 0.4855 0.035 Uiso 1 1 calc GR . . . .
H18C H -0.0596 0.4032 0.5116 0.035 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
P1 C1 1.8915(14) . ?
P1 C4 1.8774(13) . ?
P1 C11 1.8468(13) . ?
Si1 C13 1.8943(14) . ?
Si1 C16 1.8639(14) . ?
Si1 C17 1.8678(15) . ?
Si1 C18 1.8672(14) . ?
O1 C1 1.4541(15) . ?
O1 C6 1.4326(15) . ?
O2 C3 1.4287(15) . ?
O2 C4 1.4536(15) . ?
O3 C3 1.4345(15) . ?
O3 C6 1.4334(16) . ?
N1 C11 1.3545(17) . ?
N1 C15 1.3408(17) . ?
C1 C2 1.5214(18) . ?
C1 C7 1.5176(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5296(17) . ?
C3 C8 1.5100(18) . ?
C4 C5 1.5322(17) . ?
C4 C9 1.5187(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5196(18) . ?
C6 C10 1.5122(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3944(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.4017(18) . ?
C13 C14 1.4004(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C4 P1 C1 92.43(6) . . ?
C11 P1 C1 102.52(6) . . ?
C11 P1 C4 104.90(6) . . ?
C16 Si1 C13 106.71(6) . . ?
C16 Si1 C17 109.99(7) . . ?
C16 Si1 C18 111.41(7) . . ?
C17 Si1 C13 107.84(6) . . ?
C18 Si1 C13 109.91(6) . . ?
C18 Si1 C17 110.82(7) . . ?
C6 O1 C1 115.40(9) . . ?
C3 O2 C4 114.98(9) . . ?
C6 O3 C3 111.50(9) . . ?
C15 N1 C11 117.09(11) . . ?
O1 C1 P1 106.66(8) . . ?
O1 C1 C2 108.44(10) . . ?
O1 C1 C7 105.39(10) . . ?
C2 C1 P1 111.54(9) . . ?
C7 C1 P1 110.84(9) . . ?
C7 C1 C2 113.53(11) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.76(10) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
O2 C3 O3 110.31(10) . . ?
O2 C3 C2 112.09(10) . . ?
O2 C3 C8 106.20(11) . . ?
O3 C3 C2 107.66(10) . . ?
O3 C3 C8 107.53(10) . . ?
C8 C3 C2 112.98(11) . . ?
O2 C4 P1 114.46(8) . . ?
O2 C4 C5 107.92(10) . . ?
O2 C4 C9 106.61(10) . . ?
C5 C4 P1 104.99(8) . . ?
C9 C4 P1 112.35(9) . . ?
C9 C4 C5 110.44(10) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.57(10) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O1 C6 O3 110.45(10) . . ?
O1 C6 C5 111.29(10) . . ?
O1 C6 C10 106.57(10) . . ?
O3 C6 C5 108.14(10) . . ?
O3 C6 C10 107.60(10) . . ?
C10 C6 C5 112.73(11) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 P1 112.14(9) . . ?
N1 C11 C12 121.83(12) . . ?
C12 C11 P1 125.88(10) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.31(12) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 Si1 118.14(10) . . ?
C14 C13 Si1 125.92(10) . . ?
C14 C13 C12 115.94(12) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.57(12) . . ?
C15 C14 H14 120.2 . . ?
N1 C15 C14 124.18(12) . . ?
N1 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
P1 C1 C2 C3 65.27(12) . . . . ?
P1 C4 C5 C6 70.00(11) . . . . ?
P1 C11 C12 C13 -172.63(10) . . . . ?
Si1 C13 C14 C15 178.90(10) . . . . ?
O1 C1 C2 C3 -51.89(13) . . . . ?
O2 C4 C5 C6 -52.49(13) . . . . ?
N1 C11 C12 C13 2.5(2) . . . . ?
C1 P1 C4 O2 53.45(9) . . . . ?
C1 P1 C4 C5 -64.70(9) . . . . ?
C1 P1 C4 C9 175.23(9) . . . . ?
C1 P1 C11 N1 87.61(10) . . . . ?
C1 P1 C11 C12 -96.82(12) . . . . ?
C1 O1 C6 O3 -55.95(13) . . . . ?
C1 O1 C6 C5 64.19(13) . . . . ?
C1 O1 C6 C10 -172.54(10) . . . . ?
C1 C2 C3 O2 -63.64(13) . . . . ?
C1 C2 C3 O3 57.85(13) . . . . ?
C1 C2 C3 C8 176.42(11) . . . . ?
C3 O2 C4 P1 -63.30(12) . . . . ?
C3 O2 C4 C5 53.17(13) . . . . ?
C3 O2 C4 C9 171.83(9) . . . . ?
C3 O3 C6 O1 60.72(13) . . . . ?
C3 O3 C6 C5 -61.29(12) . . . . ?
C3 O3 C6 C10 176.67(10) . . . . ?
C4 P1 C1 O1 63.19(9) . . . . ?
C4 P1 C1 C2 -55.04(9) . . . . ?
C4 P1 C1 C7 177.41(9) . . . . ?
C4 P1 C11 N1 -176.41(9) . . . . ?
C4 P1 C11 C12 -0.85(13) . . . . ?
C4 O2 C3 O3 -57.35(13) . . . . ?
C4 O2 C3 C2 62.60(13) . . . . ?
C4 O2 C3 C8 -173.58(9) . . . . ?
C4 C5 C6 O1 -63.96(13) . . . . ?
C4 C5 C6 O3 57.53(13) . . . . ?
C4 C5 C6 C10 176.36(11) . . . . ?
C6 O1 C1 P1 -68.54(11) . . . . ?
C6 O1 C1 C2 51.70(14) . . . . ?
C6 O1 C1 C7 173.58(11) . . . . ?
C6 O3 C3 O2 60.74(12) . . . . ?
C6 O3 C3 C2 -61.85(12) . . . . ?
C6 O3 C3 C8 176.13(10) . . . . ?
C7 C1 C2 C3 -168.65(11) . . . . ?
C9 C4 C5 C6 -168.67(11) . . . . ?
C11 P1 C1 O1 169.04(8) . . . . ?
C11 P1 C1 C2 50.81(10) . . . . ?
C11 P1 C1 C7 -76.74(10) . . . . ?
C11 P1 C4 O2 -50.18(10) . . . . ?
C11 P1 C4 C5 -168.33(8) . . . . ?
C11 P1 C4 C9 71.60(10) . . . . ?
C11 N1 C15 C14 -2.21(19) . . . . ?
C11 C12 C13 Si1 178.61(10) . . . . ?
C11 C12 C13 C14 -2.03(19) . . . . ?
C12 C13 C14 C15 -0.40(19) . . . . ?
C13 C14 C15 N1 2.6(2) . . . . ?
C15 N1 C11 P1 175.39(9) . . . . ?
C15 N1 C11 C12 -0.38(18) . . . . ?
C16 Si1 C13 C12 61.05(12) . . . . ?
C16 Si1 C13 C14 -118.24(12) . . . . ?
C17 Si1 C13 C12 -57.09(12) . . . . ?
C17 Si1 C13 C14 123.62(12) . . . . ?
C18 Si1 C13 C12 -178.01(10) . . . . ?
C18 Si1 C13 C14 2.71(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L7b
_database_code_depnum_ccdc_archive 'CCDC 1497898'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT915_L7b                 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         49 %
RESPONSE: Absolute structure not determined due to low Friedel Pair Coverage.
;
# Added during the CSD deposition process: Friday 05 August 2016 03:50 PM
# end Validation Reply Form

_audit_creation_date             2016-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H28 N O3 P Si'
_chemical_formula_sum            'C18 H28 N O3 P Si'
_chemical_formula_weight         365.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Si Si 0.0817 0.0704 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   11.9811(8)
_cell_length_b                   12.8561(11)
_cell_length_c                   12.8375(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1977.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4758
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8133.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17162
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.753
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.984
_diffrn_reflns_theta_min         1.584
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.452
_reflns_Friedel_fraction_full    0.548
_reflns_Friedel_fraction_max     0.491
_reflns_number_gt                3307
_reflns_number_total             3582
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0385
_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)+(0.0660P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.24535(5) 0.46878(5) 0.51083(7) 0.01246(15) Uani 1 1 d . . . . .
Si1 Si 0.31132(7) 0.87512(6) 0.46620(7) 0.01776(19) Uani 1 1 d . . . . .
O1 O 0.37919(16) 0.34189(16) 0.61990(15) 0.0144(4) Uani 1 1 d . . . . .
O2 O 0.30551(14) 0.31547(15) 0.36597(16) 0.0140(4) Uani 1 1 d . . . . .
O3 O 0.41287(16) 0.22089(15) 0.48651(15) 0.0157(4) Uani 1 1 d . . . . .
N2 N 0.27960(18) 0.66301(18) 0.4553(2) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.3914(2) 0.4307(2) 0.5510(2) 0.0140(5) Uani 1 1 d . . . . .
C2 C 0.4618(2) 0.3983(2) 0.4581(2) 0.0148(5) Uani 1 1 d . . . . .
H2A H 0.5380 0.3858 0.4805 0.018 Uiso 1 1 calc R . . . .
H2B H 0.4629 0.4539 0.4071 0.018 Uiso 1 1 calc R . . . .
C3 C 0.4148(2) 0.2997(2) 0.4082(2) 0.0144(6) Uani 1 1 d . . . . .
C4 C 0.2211(2) 0.3432(2) 0.4416(2) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.2235(2) 0.2611(2) 0.5282(2) 0.0152(6) Uani 1 1 d . . . . .
H5A H 0.1735 0.2818 0.5839 0.018 Uiso 1 1 calc R . . . .
H5B H 0.1976 0.1950 0.5008 0.018 Uiso 1 1 calc R . . . .
C6 C 0.3412(2) 0.2486(2) 0.5709(2) 0.0154(6) Uani 1 1 d . . . . .
C7 C 0.4446(2) 0.5156(2) 0.6164(2) 0.0160(6) Uani 1 1 d . . . . .
H7A H 0.4479 0.5789 0.5768 0.024 Uiso 1 1 calc GR . . . .
H7B H 0.5188 0.4950 0.6357 0.024 Uiso 1 1 calc GR . . . .
H7C H 0.4009 0.5267 0.6781 0.024 Uiso 1 1 calc GR . . . .
C8 C 0.4853(3) 0.2603(2) 0.3193(2) 0.0194(6) Uani 1 1 d . . . . .
H8A H 0.4546 0.1963 0.2936 0.029 Uiso 1 1 calc GR . . . .
H8B H 0.5601 0.2486 0.3434 0.029 Uiso 1 1 calc GR . . . .
H8C H 0.4861 0.3111 0.2645 0.029 Uiso 1 1 calc GR . . . .
C9 C 0.1101(2) 0.3412(2) 0.3836(2) 0.0176(6) Uani 1 1 d . . . . .
H9A H 0.0509 0.3597 0.4305 0.026 Uiso 1 1 calc GR . . . .
H9B H 0.0970 0.2726 0.3566 0.026 Uiso 1 1 calc GR . . . .
H9C H 0.1123 0.3901 0.3271 0.026 Uiso 1 1 calc GR . . . .
C10 C 0.3506(3) 0.1642(2) 0.6518(2) 0.0219(6) Uani 1 1 d . . . . .
H10A H 0.4270 0.1580 0.6736 0.033 Uiso 1 1 calc GR . . . .
H10B H 0.3261 0.0994 0.6225 0.033 Uiso 1 1 calc GR . . . .
H10C H 0.3048 0.1815 0.7106 0.033 Uiso 1 1 calc GR . . . .
C11 C 0.2743(2) 0.5678(2) 0.4106(2) 0.0139(5) Uani 1 1 d . . . . .
C12 C 0.2886(2) 0.5535(2) 0.3042(2) 0.0163(6) Uani 1 1 d . . . . .
H12 H 0.2851 0.4873 0.2754 0.020 Uiso 1 1 calc R . . . .
C13 C 0.3082(2) 0.6392(2) 0.2417(2) 0.0186(6) Uani 1 1 d . . . . .
H13 H 0.3160 0.6317 0.1700 0.022 Uiso 1 1 calc R . . . .
C14 C 0.3160(2) 0.7362(2) 0.2875(2) 0.0177(6) Uani 1 1 d . . . . .
H14 H 0.3305 0.7945 0.2468 0.021 Uiso 1 1 calc R . . . .
C15 C 0.3019(2) 0.7465(2) 0.3946(2) 0.0160(6) Uani 1 1 d . . . . .
C16 C 0.1701(3) 0.9109(3) 0.5151(3) 0.0334(8) Uani 1 1 d . . . . .
H16A H 0.1242 0.9323 0.4577 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.1766 0.9670 0.5641 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.1368 0.8518 0.5487 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.3642(4) 0.9748(3) 0.3739(3) 0.0425(10) Uani 1 1 d . . . . .
H17A H 0.4353 0.9531 0.3469 0.064 Uiso 1 1 calc GR . . . .
H17B H 0.3725 1.0399 0.4096 0.064 Uiso 1 1 calc GR . . . .
H17C H 0.3123 0.9827 0.3176 0.064 Uiso 1 1 calc GR . . . .
C18 C 0.4088(3) 0.8560(3) 0.5776(3) 0.0301(8) Uani 1 1 d . . . . .
H18A H 0.3821 0.8003 0.6208 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.4128 0.9188 0.6178 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.4817 0.8389 0.5516 0.045 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
P1 C1 1.888(3) . ?
P1 C4 1.866(3) . ?
P1 C11 1.843(3) . ?
Si1 C15 1.895(3) . ?
Si1 C16 1.862(3) . ?
Si1 C17 1.856(4) . ?
Si1 C18 1.863(3) . ?
O1 C1 1.451(3) . ?
O1 C6 1.428(3) . ?
O2 C3 1.432(3) . ?
O2 C4 1.446(3) . ?
O3 C3 1.427(3) . ?
O3 C6 1.428(3) . ?
N2 C11 1.353(4) . ?
N2 C15 1.353(4) . ?
C1 C2 1.520(4) . ?
C1 C7 1.517(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.528(4) . ?
C3 C8 1.507(4) . ?
C4 C5 1.534(4) . ?
C4 C9 1.524(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.522(4) . ?
C6 C10 1.506(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.388(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C4 P1 C1 92.88(12) . . ?
C11 P1 C1 101.27(12) . . ?
C11 P1 C4 107.10(13) . . ?
C16 Si1 C15 108.98(14) . . ?
C16 Si1 C18 110.08(18) . . ?
C17 Si1 C15 108.23(15) . . ?
C17 Si1 C16 110.78(19) . . ?
C17 Si1 C18 111.5(2) . . ?
C18 Si1 C15 107.12(14) . . ?
C6 O1 C1 115.1(2) . . ?
C3 O2 C4 114.9(2) . . ?
C3 O3 C6 111.5(2) . . ?
C15 N2 C11 118.9(2) . . ?
O1 C1 P1 106.10(17) . . ?
O1 C1 C2 108.5(2) . . ?
O1 C1 C7 105.7(2) . . ?
C2 C1 P1 111.77(19) . . ?
C7 C1 P1 110.76(19) . . ?
C7 C1 C2 113.5(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.6(2) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
O2 C3 C2 112.2(2) . . ?
O2 C3 C8 105.9(2) . . ?
O3 C3 O2 110.7(2) . . ?
O3 C3 C2 107.4(2) . . ?
O3 C3 C8 107.7(2) . . ?
C8 C3 C2 112.9(2) . . ?
O2 C4 P1 115.08(18) . . ?
O2 C4 C5 107.7(2) . . ?
O2 C4 C9 106.2(2) . . ?
C5 C4 P1 104.31(19) . . ?
C9 C4 P1 112.52(19) . . ?
C9 C4 C5 111.0(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.5(2) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
O1 C6 C5 111.5(2) . . ?
O1 C6 C10 106.1(2) . . ?
O3 C6 O1 110.6(2) . . ?
O3 C6 C5 108.1(2) . . ?
O3 C6 C10 107.3(2) . . ?
C10 C6 C5 113.2(2) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 P1 109.7(2) . . ?
N2 C11 C12 122.0(3) . . ?
C12 C11 P1 128.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
N2 C15 Si1 115.1(2) . . ?
N2 C15 C14 121.1(3) . . ?
C14 C15 Si1 123.7(2) . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
P1 C1 C2 C3 -64.7(3) . . . . ?
P1 C4 C5 C6 -69.9(2) . . . . ?
P1 C11 C12 C13 179.0(2) . . . . ?
O1 C1 C2 C3 52.0(3) . . . . ?
O2 C4 C5 C6 52.8(3) . . . . ?
N2 C11 C12 C13 -0.4(4) . . . . ?
C1 P1 C4 O2 -52.6(2) . . . . ?
C1 P1 C4 C5 65.18(18) . . . . ?
C1 P1 C4 C9 -174.4(2) . . . . ?
C1 P1 C11 N2 -90.6(2) . . . . ?
C1 P1 C11 C12 89.9(3) . . . . ?
C1 O1 C6 O3 55.9(3) . . . . ?
C1 O1 C6 C5 -64.4(3) . . . . ?
C1 O1 C6 C10 172.0(2) . . . . ?
C1 C2 C3 O2 63.8(3) . . . . ?
C1 C2 C3 O3 -58.1(3) . . . . ?
C1 C2 C3 C8 -176.6(2) . . . . ?
C3 O2 C4 P1 62.6(3) . . . . ?
C3 O2 C4 C5 -53.2(3) . . . . ?
C3 O2 C4 C9 -172.2(2) . . . . ?
C3 O3 C6 O1 -61.2(3) . . . . ?
C3 O3 C6 C5 61.1(3) . . . . ?
C3 O3 C6 C10 -176.5(2) . . . . ?
C4 P1 C1 O1 -64.04(19) . . . . ?
C4 P1 C1 C2 54.1(2) . . . . ?
C4 P1 C1 C7 -178.3(2) . . . . ?
C4 P1 C11 N2 172.83(17) . . . . ?
C4 P1 C11 C12 -6.7(3) . . . . ?
C4 O2 C3 O3 57.4(3) . . . . ?
C4 O2 C3 C2 -62.6(3) . . . . ?
C4 O2 C3 C8 173.8(2) . . . . ?
C4 C5 C6 O1 64.1(3) . . . . ?
C4 C5 C6 O3 -57.7(3) . . . . ?
C4 C5 C6 C10 -176.4(2) . . . . ?
C6 O1 C1 P1 68.7(2) . . . . ?
C6 O1 C1 C2 -51.5(3) . . . . ?
C6 O1 C1 C7 -173.6(2) . . . . ?
C6 O3 C3 O2 -60.6(3) . . . . ?
C6 O3 C3 C2 62.2(3) . . . . ?
C6 O3 C3 C8 -175.9(2) . . . . ?
C7 C1 C2 C3 169.2(2) . . . . ?
C9 C4 C5 C6 168.7(2) . . . . ?
C11 P1 C1 O1 -172.12(17) . . . . ?
C11 P1 C1 C2 -54.0(2) . . . . ?
C11 P1 C1 C7 73.6(2) . . . . ?
C11 P1 C4 O2 50.1(2) . . . . ?
C11 P1 C4 C5 167.90(16) . . . . ?
C11 P1 C4 C9 -71.7(2) . . . . ?
C11 N2 C15 Si1 -178.35(18) . . . . ?
C11 N2 C15 C14 2.0(4) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C13 C14 C15 Si1 179.7(2) . . . . ?
C13 C14 C15 N2 -0.7(4) . . . . ?
C15 N2 C11 P1 179.02(19) . . . . ?
C15 N2 C11 C12 -1.5(4) . . . . ?
C16 Si1 C15 N2 -68.4(2) . . . . ?
C16 Si1 C15 C14 111.3(3) . . . . ?
C17 Si1 C15 N2 171.1(2) . . . . ?
C17 Si1 C15 C14 -9.3(3) . . . . ?
C18 Si1 C15 N2 50.7(2) . . . . ?
C18 Si1 C15 C14 -129.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
