# 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. 
# 
#######################################################################

data_3_15srv015
_database_code_depnum_ccdc_archive 'CCDC 1457275'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_audit_creation_date             2015-01-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H25 Cl N O2 P Ru'
_chemical_formula_sum            'C22 H25 Cl N O2 P Ru'
_chemical_formula_weight         502.92
_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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.5685(6)
_cell_length_b                   8.1196(4)
_cell_length_c                   20.4312(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5345(16)
_cell_angle_gamma                90.00
_cell_volume                     2084.28(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.48
_cell_measurement_theta_min      2.54
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0940 before and 0.0502 after correction.
The Ratio of minimum to maximum transmission is 0.9219.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            43150
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         2.54
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4673
_reflns_number_total             5811
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.093
_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     257
_refine_ls_number_reflns         5811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0629
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ru1 Ru 0.928604(13) 0.65893(2) 0.394099(8) 0.01292(5) Uani 1 d . . .
Cl1 Cl 0.97770(4) 0.39756(7) 0.34719(3) 0.02024(12) Uani 1 d . . .
P1 P 0.69134(4) 0.54631(7) 0.40983(3) 0.01460(11) Uani 1 d . . .
O1 O 0.80512(12) 0.53096(19) 0.43724(7) 0.0165(3) Uani 1 d . . .
O2 O 0.61612(13) 0.6577(2) 0.44216(8) 0.0234(3) Uani 1 d . . .
N1 N 0.81601(13) 0.6616(2) 0.31557(8) 0.0149(3) Uani 1 d . . .
C1 C 0.71442(16) 0.6132(3) 0.32559(11) 0.0151(4) Uani 1 d . . .
C2 C 0.63686(18) 0.6190(3) 0.27567(12) 0.0201(5) Uani 1 d . . .
C3 C 0.66667(19) 0.6728(3) 0.21431(12) 0.0248(5) Uani 1 d . . .
H3 H 0.6154 0.6786 0.1794 0.030 Uiso 1 calc . . R
C4 C 0.7707(2) 0.7178(3) 0.20399(12) 0.0250(5) Uani 1 d . . .
H4 H 0.7919 0.7526 0.1619 0.030 Uiso 1 calc . . R
C5 C 0.84356(19) 0.7118(3) 0.25570(11) 0.0211(5) Uani 1 d . . .
H5 H 0.9151 0.7439 0.2488 0.025 Uiso 1 calc . . R
C6 C 0.52381(18) 0.5690(4) 0.28734(13) 0.0314(6) Uani 1 d . . .
H6A H 0.5158 0.4505 0.2796 0.047 Uiso 1 calc . . GR
H6B H 0.4759 0.6297 0.2574 0.047 Uiso 1 calc . . GR
H6C H 0.5061 0.5942 0.3327 0.047 Uiso 1 calc . . GR
C7 C 0.63784(16) 0.3413(3) 0.40404(10) 0.0163(4) Uani 1 d . . .
C8 C 0.54527(17) 0.3018(3) 0.43686(11) 0.0195(5) Uani 1 d . . .
H8 H 0.5093 0.3845 0.4606 0.023 Uiso 1 calc . . R
C9 C 0.50581(18) 0.1433(3) 0.43498(11) 0.0237(5) Uani 1 d . . .
H9 H 0.4436 0.1168 0.4582 0.028 Uiso 1 calc . . R
C10 C 0.55620(19) 0.0232(3) 0.39955(12) 0.0253(5) Uani 1 d . . .
H10 H 0.5286 -0.0857 0.3982 0.030 Uiso 1 calc . . R
C11 C 0.6476(2) 0.0616(3) 0.36572(12) 0.0254(5) Uani 1 d . . .
H11 H 0.6815 -0.0206 0.3406 0.031 Uiso 1 calc . . R
C12 C 0.68918(18) 0.2199(3) 0.36855(12) 0.0213(5) Uani 1 d . . .
H12 H 0.7525 0.2453 0.3463 0.026 Uiso 1 calc . . R
C13 C 1.09475(17) 0.7424(3) 0.39394(11) 0.0181(5) Uani 1 d . . .
C14 C 1.07028(17) 0.6870(3) 0.45825(11) 0.0186(5) Uani 1 d . . .
H14 H 1.1146 0.6075 0.4795 0.022 Uiso 1 calc . . R
C15 C 0.98212(18) 0.7485(3) 0.49011(11) 0.0197(5) Uani 1 d . . .
H15 H 0.9672 0.7090 0.5327 0.024 Uiso 1 calc . . R
C16 C 0.91387(18) 0.8687(3) 0.46079(11) 0.0207(5) Uani 1 d . . .
C17 C 0.93891(17) 0.9245(3) 0.39762(12) 0.0196(5) Uani 1 d . . .
H17 H 0.8950 1.0053 0.3769 0.024 Uiso 1 calc . . R
C18 C 1.02839(17) 0.8627(3) 0.36438(11) 0.0189(5) Uani 1 d . . .
H18 H 1.0436 0.9027 0.3219 0.023 Uiso 1 calc . . R
C19 C 0.81650(19) 0.9250(3) 0.49590(13) 0.0293(6) Uani 1 d . . .
H19A H 0.7850 1.0198 0.4729 0.044 Uiso 1 calc . . GR
H19B H 0.8366 0.9568 0.5408 0.044 Uiso 1 calc . . GR
H19C H 0.7646 0.8351 0.4968 0.044 Uiso 1 calc . . GR
C20 C 1.19123(18) 0.6689(3) 0.36258(12) 0.0244(5) Uani 1 d . . .
H20 H 1.1925 0.5486 0.3731 0.029 Uiso 1 calc . . R
C21 C 1.2916(2) 0.7478(4) 0.39516(16) 0.0428(8) Uani 1 d . . .
H21A H 1.2951 0.8644 0.3831 0.064 Uiso 1 calc . . GR
H21B H 1.3553 0.6909 0.3802 0.064 Uiso 1 calc . . GR
H21C H 1.2879 0.7380 0.4429 0.064 Uiso 1 calc . . GR
C22 C 1.1916(2) 0.6860(4) 0.28895(13) 0.0363(7) Uani 1 d . . .
H22A H 1.1258 0.6391 0.2700 0.054 Uiso 1 calc . . GR
H22B H 1.2530 0.6272 0.2718 0.054 Uiso 1 calc . . GR
H22C H 1.1961 0.8028 0.2773 0.054 Uiso 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
Ru1 Cl1 2.4155(6) . ?
Ru1 O1 2.0829(14) . ?
Ru1 N1 2.1109(17) . ?
Ru1 C13 2.195(2) . ?
Ru1 C14 2.194(2) . ?
Ru1 C15 2.181(2) . ?
Ru1 C16 2.192(2) . ?
Ru1 C17 2.161(2) . ?
Ru1 C18 2.172(2) . ?
P1 O1 1.5269(16) . ?
P1 O2 1.4769(16) . ?
P1 C1 1.835(2) . ?
P1 C7 1.798(2) . ?
N1 C1 1.357(3) . ?
N1 C5 1.343(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.389(3) . ?
C2 C6 1.503(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.396(3) . ?
C7 C12 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.430(3) . ?
C13 C18 1.410(3) . ?
C13 C20 1.509(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.421(3) . ?
C16 C17 1.411(3) . ?
C16 C19 1.506(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.421(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 1.0000 . ?
C20 C21 1.549(4) . ?
C20 C22 1.511(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O1 Ru1 Cl1 86.03(4) . . ?
O1 Ru1 N1 80.50(6) . . ?
O1 Ru1 C13 150.94(7) . . ?
O1 Ru1 C14 113.64(7) . . ?
O1 Ru1 C15 90.07(7) . . ?
O1 Ru1 C16 92.77(7) . . ?
O1 Ru1 C17 121.89(7) . . ?
O1 Ru1 C18 160.13(7) . . ?
N1 Ru1 Cl1 83.15(5) . . ?
N1 Ru1 C13 127.88(8) . . ?
N1 Ru1 C14 165.85(7) . . ?
N1 Ru1 C15 149.80(8) . . ?
N1 Ru1 C16 113.47(8) . . ?
N1 Ru1 C17 93.06(8) . . ?
N1 Ru1 C18 99.20(8) . . ?
C13 Ru1 Cl1 91.00(6) . . ?
C14 Ru1 Cl1 96.69(6) . . ?
C14 Ru1 C13 38.02(8) . . ?
C15 Ru1 Cl1 125.02(6) . . ?
C15 Ru1 C13 68.16(8) . . ?
C15 Ru1 C14 37.12(8) . . ?
C15 Ru1 C16 37.91(9) . . ?
C16 Ru1 Cl1 162.93(6) . . ?
C16 Ru1 C13 81.80(8) . . ?
C16 Ru1 C14 68.20(8) . . ?
C17 Ru1 Cl1 150.93(6) . . ?
C17 Ru1 C13 68.66(8) . . ?
C17 Ru1 C14 80.18(8) . . ?
C17 Ru1 C15 67.70(9) . . ?
C17 Ru1 C16 37.83(9) . . ?
C17 Ru1 C18 38.28(8) . . ?
C18 Ru1 Cl1 113.74(6) . . ?
C18 Ru1 C13 37.66(8) . . ?
C18 Ru1 C14 67.82(8) . . ?
C18 Ru1 C15 80.27(8) . . ?
C18 Ru1 C16 68.97(9) . . ?
O1 P1 C1 101.43(9) . . ?
O1 P1 C7 107.07(9) . . ?
O2 P1 O1 119.37(9) . . ?
O2 P1 C1 110.94(10) . . ?
O2 P1 C7 110.70(10) . . ?
C7 P1 C1 106.30(10) . . ?
P1 O1 Ru1 120.35(9) . . ?
C1 N1 Ru1 119.79(14) . . ?
C5 N1 Ru1 120.75(14) . . ?
C5 N1 C1 119.46(18) . . ?
N1 C1 P1 113.59(15) . . ?
N1 C1 C2 121.5(2) . . ?
C2 C1 P1 124.86(16) . . ?
C1 C2 C6 121.4(2) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 C6 120.5(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 P1 119.75(17) . . ?
C12 C7 P1 120.80(16) . . ?
C12 C7 C8 119.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C14 C13 Ru1 70.96(12) . . ?
C14 C13 C20 117.4(2) . . ?
C18 C13 Ru1 70.28(12) . . ?
C18 C13 C14 118.2(2) . . ?
C18 C13 C20 124.4(2) . . ?
C20 C13 Ru1 130.82(16) . . ?
Ru1 C14 H14 131.2 . . ?
C13 C14 Ru1 71.03(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 Ru1 70.94(12) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
Ru1 C15 H15 130.3 . . ?
C14 C15 Ru1 71.95(13) . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.9(2) . . ?
C16 C15 Ru1 71.44(13) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 Ru1 70.64(13) . . ?
C15 C16 C19 119.8(2) . . ?
C17 C16 Ru1 69.92(13) . . ?
C17 C16 C15 117.3(2) . . ?
C17 C16 C19 122.8(2) . . ?
C19 C16 Ru1 127.98(16) . . ?
Ru1 C17 H17 129.8 . . ?
C16 C17 Ru1 72.26(13) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.5(2) . . ?
C18 C17 Ru1 71.27(13) . . ?
C18 C17 H17 119.3 . . ?
Ru1 C18 H18 130.3 . . ?
C13 C18 Ru1 72.06(13) . . ?
C13 C18 C17 120.5(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 Ru1 70.45(12) . . ?
C17 C18 H18 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20 107.7 . . ?
C13 C20 C21 108.0(2) . . ?
C13 C20 C22 114.2(2) . . ?
C21 C20 H20 107.7 . . ?
C22 C20 H20 107.7 . . ?
C22 C20 C21 111.5(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O2 P1 O1 Ru1 -99.90(12) . . . . ?
N1 C1 P1 O1 -12.68(17) . . . . ?
N1 C1 P1 O2 115.13(16) . . . . ?
C1 P1 O1 Ru1 22.25(12) . . . . ?
C2 C1 P1 O1 168.64(19) . . . . ?
C2 C1 P1 O2 -63.5(2) . . . . ?
C2 C1 P1 C7 56.9(2) . . . . ?
C7 P1 O1 Ru1 133.45(10) . . . . ?
C7 P1 C1 N1 -124.46(16) . . . . ?
C8 C7 P1 O1 122.35(18) . . . . ?
C8 C7 P1 O2 -9.3(2) . . . . ?
C8 C7 P1 C1 -129.85(18) . . . . ?
C12 C7 P1 O1 -56.0(2) . . . . ?
C12 C7 P1 O2 172.39(18) . . . . ?
C12 C7 P1 C1 51.8(2) . . . . ?
C14 C13 C20 C21 -75.3(3) . . . . ?
C14 C13 C20 C22 160.1(2) . . . . ?
C18 C13 C20 C21 103.9(3) . . . . ?
C18 C13 C20 C22 -20.6(3) . . . . ?
C21 C20 C13 Ru1 -163.2(2) . . . . ?
C22 C20 C13 Ru1 72.3(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_15srv069
_database_code_depnum_ccdc_archive 'CCDC 1457276'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H24 Cl Ir N O2 P, H2 O'
_chemical_formula_sum            'C17 H26 Cl Ir N O3 P'
_chemical_formula_weight         551.01
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.7318(2)
_cell_length_b                   16.6565(2)
_cell_length_c                   8.34330(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.664(2)
_cell_angle_gamma                90.00
_cell_volume                     1950.75(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.55
_cell_measurement_theta_min      2.45
_exptl_absorpt_coefficient_mu    7.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1357 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.5083.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20026
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.81
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                5436
_reflns_number_total             5620
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.033(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5620
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.9500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0497
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ir1 Ir 0.25093(2) 0.303665(5) 0.75587(3) 0.01057(3) Uani 1 d . . .
Cl2 Cl 0.31335(8) 0.33278(7) 0.52358(13) 0.01485(19) Uani 1 d . . .
P1 P 0.34493(6) 0.13297(6) 0.74173(11) 0.01357(17) Uani 1 d . . .
O1 O 0.35891(19) 0.21462(16) 0.8297(3) 0.0163(5) Uani 1 d . . .
O2 O 0.3468(2) 0.06054(16) 0.8488(4) 0.0238(6) Uani 1 d . . .
N1 N 0.1797(2) 0.21137(18) 0.5921(4) 0.0125(6) Uani 1 d . . .
C1 C 0.2298(2) 0.1431(2) 0.5811(4) 0.0127(6) Uani 1 d . . .
C2 C 0.1953(3) 0.0881(2) 0.4535(5) 0.0171(7) Uani 1 d . . .
H2 H 0.2314 0.0414 0.4487 0.021 Uiso 1 calc . . R
C3 C 0.1085(3) 0.1005(2) 0.3322(5) 0.0184(7) Uani 1 d . . .
C4 C 0.0565(3) 0.1685(2) 0.3494(5) 0.0185(7) Uani 1 d . . .
H4 H -0.0047 0.1781 0.2719 0.022 Uiso 1 calc . . R
C5 C 0.0944(2) 0.2215(2) 0.4793(5) 0.0153(6) Uani 1 d . . .
H5 H 0.0581 0.2674 0.4888 0.018 Uiso 1 calc . . R
C6 C 0.0726(3) 0.0444(3) 0.1861(6) 0.0304(10) Uani 1 d . . .
H6A H 0.1152 0.0464 0.1159 0.046 Uiso 1 calc . . GR
H6B H 0.0083 0.0605 0.1192 0.046 Uiso 1 calc . . GR
H6C H 0.0709 -0.0104 0.2277 0.046 Uiso 1 calc . . GR
C7 C 0.4295(3) 0.1232(3) 0.6276(5) 0.0243(8) Uani 1 d . . .
H7A H 0.4238 0.1692 0.5520 0.036 Uiso 1 calc . . GR
H7B H 0.4170 0.0736 0.5614 0.036 Uiso 1 calc . . GR
H7C H 0.4941 0.1214 0.7068 0.036 Uiso 1 calc . . GR
C8 C 0.1987(4) 0.3197(3) 0.9708(6) 0.0123(9) Uani 1 d . . .
C9 C 0.1368(2) 0.3608(2) 0.8265(5) 0.0176(7) Uani 1 d . . .
C10 C 0.1889(3) 0.4193(2) 0.7659(5) 0.0168(7) Uani 1 d . . .
C11 C 0.2866(2) 0.4179(2) 0.8761(5) 0.0150(7) Uani 1 d . . .
C12 C 0.2927(2) 0.3573(2) 1.0011(4) 0.0181(7) Uani 1 d . . .
C13 C 0.1732(4) 0.2585(3) 1.0763(6) 0.0314(10) Uani 1 d . . .
H13A H 0.1145 0.2314 1.0116 0.047 Uiso 1 calc . . GR
H13B H 0.1633 0.2842 1.1753 0.047 Uiso 1 calc . . GR
H13C H 0.2248 0.2192 1.1125 0.047 Uiso 1 calc . . GR
C14 C 0.0318(3) 0.3475(3) 0.7588(6) 0.0331(11) Uani 1 d . . .
H14A H 0.0104 0.3591 0.6379 0.050 Uiso 1 calc . . GR
H14B H -0.0011 0.3831 0.8165 0.050 Uiso 1 calc . . GR
H14C H 0.0172 0.2915 0.7773 0.050 Uiso 1 calc . . GR
C15 C 0.1511(4) 0.4769(3) 0.6258(7) 0.0311(13) Uani 1 d . . .
H15A H 0.1941 0.4791 0.5565 0.047 Uiso 1 calc . . GR
H15B H 0.1463 0.5303 0.6718 0.047 Uiso 1 calc . . GR
H15C H 0.0879 0.4593 0.5566 0.047 Uiso 1 calc . . GR
C16 C 0.3641(4) 0.4716(3) 0.8602(8) 0.0276(11) Uani 1 d . . .
H16A H 0.4259 0.4461 0.9131 0.041 Uiso 1 calc . . GR
H16B H 0.3610 0.5228 0.9162 0.041 Uiso 1 calc . . GR
H16C H 0.3564 0.4812 0.7409 0.041 Uiso 1 calc . . GR
C17 C 0.3805(3) 0.3319(3) 1.1356(5) 0.0281(9) Uani 1 d . . .
H17A H 0.3802 0.2735 1.1488 0.042 Uiso 1 calc . . GR
H17B H 0.3820 0.3577 1.2419 0.042 Uiso 1 calc . . GR
H17C H 0.4368 0.3480 1.1042 0.042 Uiso 1 calc . . GR
O3 O 0.3078(3) 0.0893(2) 1.1640(5) 0.0369(8) Uani 1 d . . .
H3A H 0.3215 0.0419 1.2087 0.055 Uiso 1 d . . G
H3B H 0.3125 0.0888 1.0626 0.055 Uiso 1 d . . G


_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
Ir1 Cl2 2.4328(11) . ?
Ir1 O1 2.125(3) . ?
Ir1 N1 2.112(3) . ?
Ir1 C8 2.171(5) . ?
Ir1 C9 2.164(4) . ?
Ir1 C10 2.144(4) . ?
Ir1 C11 2.140(4) . ?
Ir1 C12 2.144(3) . ?
P1 O1 1.530(3) . ?
P1 O2 1.497(3) . ?
P1 C1 1.823(3) . ?
P1 C7 1.791(4) . ?
N1 C1 1.374(4) . ?
N1 C5 1.332(4) . ?
C1 C2 1.379(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(6) . ?
C3 C4 1.400(5) . ?
C3 C6 1.499(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.443(6) . ?
C8 C12 1.469(6) . ?
C8 C13 1.468(7) . ?
C9 C10 1.426(5) . ?
C9 C14 1.493(5) . ?
C10 C11 1.453(5) . ?
C10 C15 1.484(6) . ?
C11 C12 1.434(5) . ?
C11 C16 1.488(6) . ?
C12 C17 1.493(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 H3A 0.8701 . ?
O3 H3B 0.8700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ir1 Cl2 86.53(8) . . ?
O1 Ir1 C8 105.54(15) . . ?
O1 Ir1 C9 143.44(13) . . ?
O1 Ir1 C10 154.96(12) . . ?
O1 Ir1 C11 115.40(12) . . ?
O1 Ir1 C12 92.37(12) . . ?
N1 Ir1 Cl2 82.15(9) . . ?
N1 Ir1 O1 82.00(11) . . ?
N1 Ir1 C8 113.13(16) . . ?
N1 Ir1 C9 102.80(13) . . ?
N1 Ir1 C10 123.03(13) . . ?
N1 Ir1 C11 162.39(13) . . ?
N1 Ir1 C12 149.63(14) . . ?
C8 Ir1 Cl2 161.36(12) . . ?
C9 Ir1 Cl2 129.96(11) . . ?
C9 Ir1 C8 38.90(16) . . ?
C10 Ir1 Cl2 96.91(10) . . ?
C10 Ir1 C8 66.15(16) . . ?
C10 Ir1 C9 38.65(14) . . ?
C10 Ir1 C12 65.85(14) . . ?
C11 Ir1 Cl2 95.62(10) . . ?
C11 Ir1 C8 66.53(16) . . ?
C11 Ir1 C9 65.29(14) . . ?
C11 Ir1 C10 39.66(13) . . ?
C11 Ir1 C12 39.11(14) . . ?
C12 Ir1 Cl2 127.50(11) . . ?
C12 Ir1 C8 39.80(17) . . ?
C12 Ir1 C9 65.07(13) . . ?
O1 P1 C1 103.33(15) . . ?
O1 P1 C7 108.79(18) . . ?
O2 P1 O1 117.05(17) . . ?
O2 P1 C1 110.94(16) . . ?
O2 P1 C7 110.8(2) . . ?
C7 P1 C1 105.07(18) . . ?
P1 O1 Ir1 120.10(15) . . ?
C1 N1 Ir1 118.3(2) . . ?
C5 N1 Ir1 122.8(3) . . ?
C5 N1 C1 117.9(3) . . ?
N1 C1 P1 115.2(2) . . ?
N1 C1 C2 121.5(3) . . ?
C2 C1 P1 123.3(3) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 117.3(3) . . ?
C2 C3 C6 121.4(4) . . ?
C4 C3 C6 121.3(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
P1 C7 H7A 109.5 . . ?
P1 C7 H7B 109.5 . . ?
P1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 Ir1 70.3(2) . . ?
C9 C8 C12 105.4(4) . . ?
C9 C8 C13 128.1(4) . . ?
C12 C8 Ir1 69.1(2) . . ?
C13 C8 Ir1 129.0(3) . . ?
C13 C8 C12 126.3(4) . . ?
C8 C9 Ir1 70.8(2) . . ?
C8 C9 C14 124.5(4) . . ?
C10 C9 Ir1 69.9(2) . . ?
C10 C9 C8 110.3(3) . . ?
C10 C9 C14 125.1(4) . . ?
C14 C9 Ir1 129.3(3) . . ?
C9 C10 Ir1 71.4(2) . . ?
C9 C10 C11 107.5(3) . . ?
C9 C10 C15 127.4(4) . . ?
C11 C10 Ir1 70.0(2) . . ?
C11 C10 C15 124.9(4) . . ?
C15 C10 Ir1 127.8(3) . . ?
C10 C11 Ir1 70.3(2) . . ?
C10 C11 C16 124.9(4) . . ?
C12 C11 Ir1 70.6(2) . . ?
C12 C11 C10 107.7(3) . . ?
C12 C11 C16 127.4(4) . . ?
C16 C11 Ir1 125.3(3) . . ?
C8 C12 Ir1 71.1(2) . . ?
C8 C12 C17 124.4(4) . . ?
C11 C12 Ir1 70.3(2) . . ?
C11 C12 C8 109.1(3) . . ?
C11 C12 C17 126.5(4) . . ?
C17 C12 Ir1 122.1(3) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H3A O3 H3B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.87 2.04 2.897(5) 169.6 2
O3 H3B O2 0.87 2.05 2.896(5) 164.0 .

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
N1 C1 P1 O1 -8.9(3) . . . . ?
N1 C1 P1 O2 117.3(3) . . . . ?
C2 C1 P1 O1 169.2(3) . . . . ?
C2 C1 P1 O2 -64.6(4) . . . . ?
C2 C1 P1 C7 55.2(4) . . . . ?
C7 P1 C1 N1 -122.9(3) . . . . ?


