# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1406955'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_date             2015-08-20T15:30:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21  H32  N  O  P  Sn'
_chemical_formula_sum            'C21 H32 N O P Sn'
_chemical_formula_weight         464.16
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9935(14)
_cell_length_b                   14.054(2)
_cell_length_c                   15.830(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2223.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2124
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.81
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.135
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7776
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker AXS Smart Apex'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_number            9380
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_coverage         0.751
_reflns_number_total             3811
_reflns_number_gt                3480
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Ortep for Windows(Farrugia,2012)and Mercury (Macrae, 2008).'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+1.8062P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3936
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_diff_density_max         0.829
_refine_diff_density_min         -1.14
_refine_diff_density_rms         0.106

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Sn1 Sn 0.93811(5) 0.11362(4) 0.23862(3) 0.01891(17) Uani 1 1 d . . . . .
P1 P 0.60648(19) 0.20245(17) 0.22377(13) 0.0174(5) Uani 1 1 d . . . . .
C20 C 1.0928(8) 0.0194(7) 0.2855(5) 0.025(2) Uani 1 1 d . . . . .
H20A H 1.0691 -0.0453 0.2731 0.037 Uiso 1 1 calc R U . . .
H20B H 1.1763 0.0345 0.2586 0.037 Uiso 1 1 calc R U . . .
H20C H 1.1016 0.0272 0.3455 0.037 Uiso 1 1 calc R U . . .
O1 O 0.7404(5) 0.2364(4) 0.1949(3) 0.0191(14) Uani 1 1 d . . . . .
C19 C 0.9293(9) 0.0860(7) 0.1052(5) 0.026(2) Uani 1 1 d . . . . .
H19A H 0.8944 0.0232 0.0958 0.039 Uiso 1 1 calc R U . . .
H19B H 0.872 0.1319 0.0786 0.039 Uiso 1 1 calc R U . . .
H19C H 1.0175 0.0904 0.0816 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3447(9) 0.3981(8) 0.3875(6) 0.034(2) Uani 1 1 d . . . . .
H17A H 0.3119 0.3737 0.3348 0.051 Uiso 1 1 calc R U . . .
H17B H 0.271 0.4081 0.4254 0.051 Uiso 1 1 calc R U . . .
H17C H 0.39 0.4573 0.3779 0.051 Uiso 1 1 calc R U . . .
N1 N 0.5126(6) 0.2715(5) 0.2835(4) 0.0180(16) Uani 1 1 d . . . . .
C2 C 0.7586(8) 0.0582(7) 0.2988(5) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.5311(8) -0.0333(7) 0.3675(5) 0.023(2) Uani 1 1 d . . . . .
H5 H 0.4567 -0.0636 0.3904 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3602(8) 0.1689(7) 0.1422(6) 0.025(2) Uani 1 1 d . . . . .
H12 H 0.3203 0.1691 0.1953 0.03 Uiso 1 1 calc R U . . .
C4 C 0.6584(9) -0.0685(7) 0.3804(5) 0.020(2) Uani 1 1 d . . . . .
H4 H 0.6699 -0.1233 0.4124 0.024 Uiso 1 1 calc R U . . .
C1 C 0.6293(8) 0.0944(6) 0.2847(4) 0.018(2) Uani 1 1 d . . . . .
C14 C 0.6557(9) 0.3914(8) 0.3546(5) 0.030(2) Uani 1 1 d . . . . .
H14A H 0.6861 0.4135 0.4087 0.045 Uiso 1 1 calc R U . . .
H14B H 0.7312 0.3719 0.3213 0.045 Uiso 1 1 calc R U . . .
H14C H 0.6092 0.4418 0.3261 0.045 Uiso 1 1 calc R U . . .
C21 C 1.0137(8) 0.2508(6) 0.2736(6) 0.030(2) Uani 1 1 d . . . . .
H21A H 1.0139 0.2565 0.334 0.044 Uiso 1 1 calc R U . . .
H21B H 1.1034 0.2579 0.2527 0.044 Uiso 1 1 calc R U . . .
H21C H 0.9578 0.2994 0.2497 0.044 Uiso 1 1 calc R U . . .
C13 C 0.5617(9) 0.3075(6) 0.3667(5) 0.0206(19) Uani 1 1 d . . . . .
H13 H 0.6143 0.2562 0.3924 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5565(10) 0.1784(6) 0.0549(5) 0.024(2) Uani 1 1 d . . . . .
H8 H 0.6487 0.1851 0.0498 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7696(9) -0.0237(7) 0.3464(5) 0.022(2) Uani 1 1 d . . . . .
H3 H 0.854 -0.0495 0.3559 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4419(9) 0.3269(6) 0.4263(5) 0.025(2) Uani 1 1 d . . . . .
C9 C 0.4787(9) 0.1656(7) -0.0165(6) 0.029(2) Uani 1 1 d . . . . .
H9 H 0.5189 0.1643 -0.0695 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3431(9) 0.1549(7) -0.0095(6) 0.031(2) Uani 1 1 d . . . . .
H10 H 0.2914 0.1468 -0.0578 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4975(8) 0.1814(7) 0.1341(6) 0.021(2) Uani 1 1 d . . . . .
C11 C 0.2826(10) 0.1562(7) 0.0691(6) 0.034(3) Uani 1 1 d . . . . .
H11 H 0.1904 0.1486 0.0736 0.041 Uiso 1 1 calc R U . . .
C6 C 0.5177(8) 0.0492(7) 0.3191(5) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.433 0.0744 0.3096 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4921(9) 0.3670(7) 0.5092(6) 0.035(3) Uani 1 1 d . . . . .
H16A H 0.5536 0.323 0.5345 0.052 Uiso 1 1 calc R U . . .
H16B H 0.5368 0.4264 0.4991 0.052 Uiso 1 1 calc R U . . .
H16C H 0.4178 0.3772 0.5466 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3670(10) 0.2345(7) 0.4443(6) 0.038(3) Uani 1 1 d . . . . .
H18A H 0.3345 0.2081 0.3922 0.057 Uiso 1 1 calc R U . . .
H18B H 0.4264 0.1899 0.4708 0.057 Uiso 1 1 calc R U . . .
H18C H 0.2928 0.2472 0.4812 0.057 Uiso 1 1 calc R U . . .
H1 H 0.477(7) 0.319(5) 0.257(5) 0.01(2) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Sn1 C21 2.143(9) . ?
Sn1 C19 2.149(7) . ?
Sn1 C20 2.167(8) . ?
Sn1 C2 2.176(8) . ?
P1 O1 1.492(6) . ?
P1 N1 1.648(7) . ?
P1 C1 1.813(8) . ?
P1 C7 1.814(9) . ?
C17 C15 1.523(13) . ?
N1 C13 1.494(10) . ?
C2 C3 1.379(12) . ?
C2 C1 1.406(11) . ?
C5 C4 1.380(12) . ?
C5 C6 1.397(13) . ?
C12 C7 1.388(11) . ?
C12 C11 1.405(13) . ?
C4 C3 1.386(12) . ?
C1 C6 1.394(11) . ?
C14 C13 1.519(13) . ?
C13 C15 1.548(12) . ?
C8 C9 1.383(12) . ?
C8 C7 1.385(12) . ?
C15 C16 1.515(12) . ?
C15 C18 1.526(13) . ?
C9 C10 1.368(13) . ?
C10 C11 1.384(13) . ?

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
C21 Sn1 C19 115.5(4) . . ?
C21 Sn1 C20 102.1(3) . . ?
C19 Sn1 C20 104.8(3) . . ?
C21 Sn1 C2 120.0(3) . . ?
C19 Sn1 C2 109.4(3) . . ?
C20 Sn1 C2 102.7(3) . . ?
O1 P1 N1 119.9(4) . . ?
O1 P1 C1 108.5(4) . . ?
N1 P1 C1 105.1(4) . . ?
O1 P1 C7 110.5(4) . . ?
N1 P1 C7 101.7(4) . . ?
C1 P1 C7 110.8(4) . . ?
C13 N1 P1 121.3(5) . . ?
C3 C2 C1 117.5(8) . . ?
C3 C2 Sn1 118.1(6) . . ?
C1 C2 Sn1 123.9(6) . . ?
C4 C5 C6 117.8(8) . . ?
C7 C12 C11 119.0(9) . . ?
C5 C4 C3 121.3(8) . . ?
C6 C1 C2 120.5(8) . . ?
C6 C1 P1 119.2(6) . . ?
C2 C1 P1 120.2(6) . . ?
N1 C13 C14 110.7(6) . . ?
N1 C13 C15 110.0(7) . . ?
C14 C13 C15 114.8(7) . . ?
C9 C8 C7 120.2(9) . . ?
C2 C3 C4 121.8(8) . . ?
C16 C15 C17 108.4(7) . . ?
C16 C15 C18 108.5(7) . . ?
C17 C15 C18 108.8(8) . . ?
C16 C15 C13 109.7(7) . . ?
C17 C15 C13 111.3(7) . . ?
C18 C15 C13 110.1(7) . . ?
C10 C9 C8 120.3(9) . . ?
C9 C10 C11 120.3(9) . . ?
C8 C7 C12 120.1(9) . . ?
C8 C7 P1 117.2(6) . . ?
C12 C7 P1 122.8(8) . . ?
C10 C11 C12 120.1(9) . . ?
C1 C6 C5 121.1(8) . . ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate:hexane'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1406956'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_publcif_datablock.id            {5a205740-5491-4371-b787-cae9e39dd455}

_audit_creation_date             2015-08-20T15:32:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18  H23  I N O P'
_chemical_formula_sum            'C18 H23 I N O P'
_chemical_formula_weight         427.24
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.1337(7)
_cell_length_b                   10.2928(7)
_cell_length_c                   18.6620(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1946.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_wavelength     0.71073
_cell_measurement_reflns_used    5287
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      24.06

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.325
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker AXS Smart Apex'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_number            9653
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         24.475
_diffrn_reflns_theta_full        24.475
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_coverage         0.728
_reflns_number_total             3222
_reflns_number_gt                3062
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 2012) and Mercury (Macrae, 2008).'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3176
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(11)
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
I1 I 0.88280(4) 0.98692(4) 0.92941(2) 0.06469(17) Uani 1 1 d . . . . .
P1 P 1.18489(14) 1.15600(13) 0.97131(7) 0.0424(3) Uani 1 1 d . . . . .
O1 O 1.3218(4) 1.1923(4) 0.9874(2) 0.0553(10) Uani 1 1 d . . . . .
C16 C 1.1306(9) 1.1102(11) 1.2371(4) 0.100(3) Uani 1 1 d . . . . .
H16A H 1.2251 1.1162 1.2357 0.149 Uiso 1 1 calc R U . . .
H16B H 1.0947 1.1895 1.2559 0.149 Uiso 1 1 calc R U . . .
H16C H 1.1053 1.0389 1.2673 0.149 Uiso 1 1 calc R U . . .
N1 N 1.0836(5) 1.1848(5) 1.0372(2) 0.0455(11) Uani 1 1 d . . . . .
C17 C 1.1351(9) 0.9611(8) 1.1338(4) 0.092(2) Uani 1 1 d . . . . .
H17A H 1.2296 0.9679 1.1324 0.138 Uiso 1 1 calc R U . . .
H17B H 1.1102 0.8918 1.1655 0.138 Uiso 1 1 calc R U . . .
H17C H 1.1023 0.9435 1.0866 0.138 Uiso 1 1 calc R U . . .
C7 C 1.1192(6) 1.2381(5) 0.8939(3) 0.0455(12) Uani 1 1 d . . . . .
C13 C 1.1245(6) 1.2015(6) 1.1123(3) 0.0547(14) Uani 1 1 d . . . . .
H13 H 1.2212 1.202 1.1133 0.066 Uiso 1 1 calc R U . . .
C1 C 1.1846(5) 0.9836(5) 0.9474(3) 0.0477(12) Uani 1 1 d . . . . .
C5 C 1.3177(8) 0.7924(7) 0.9299(5) 0.081(2) Uani 1 1 d . . . . .
H5 H 1.4003 0.753 0.9288 0.097 Uiso 1 1 calc R U . . .
C10 C 1.0444(7) 1.3778(7) 0.7741(4) 0.0690(18) Uani 1 1 d . . . . .
H10 H 1.0189 1.4248 0.7339 0.083 Uiso 1 1 calc R U . . .
C6 C 1.3071(7) 0.9226(6) 0.9454(3) 0.0631(16) Uani 1 1 d . . . . .
H6 H 1.383 0.9706 0.9546 0.076 Uiso 1 1 calc R U . . .
C15 C 1.0773(7) 1.0875(7) 1.1607(3) 0.0654(17) Uani 1 1 d . . . . .
C2 C 1.0738(6) 0.9085(5) 0.9319(3) 0.0524(13) Uani 1 1 d . . . . .
C9 C 1.1057(9) 1.2596(8) 0.7666(3) 0.076(2) Uani 1 1 d . . . . .
H9 H 1.1217 1.2261 0.7211 0.092 Uiso 1 1 calc R U . . .
C4 C 1.2068(10) 0.7206(7) 0.9160(5) 0.088(2) Uani 1 1 d . . . . .
H4 H 1.2144 0.6324 0.906 0.106 Uiso 1 1 calc R U . . .
C3 C 1.0841(9) 0.7778(6) 0.9168(4) 0.076(2) Uani 1 1 d . . . . .
H3 H 1.009 0.729 0.9071 0.091 Uiso 1 1 calc R U . . .
C8 C 1.1435(7) 1.1908(6) 0.8263(3) 0.0616(16) Uani 1 1 d . . . . .
H8 H 1.186 1.1113 0.8209 0.074 Uiso 1 1 calc R U . . .
C11 C 1.0213(7) 1.4253(6) 0.8407(4) 0.0659(17) Uani 1 1 d . . . . .
H11 H 0.9801 1.5056 0.8457 0.079 Uiso 1 1 calc R U . . .
C12 C 1.0572(6) 1.3579(6) 0.9006(3) 0.0555(14) Uani 1 1 d . . . . .
H12 H 1.0402 1.3921 0.9458 0.067 Uiso 1 1 calc R U . . .
C14 C 1.0777(7) 1.3349(7) 1.1373(4) 0.0736(19) Uani 1 1 d . . . . .
H14A H 1.1034 1.3479 1.1863 0.11 Uiso 1 1 calc R U . . .
H14B H 1.1169 1.401 1.1079 0.11 Uiso 1 1 calc R U . . .
H14C H 0.9834 1.3397 1.1336 0.11 Uiso 1 1 calc R U . . .
C18 C 0.9303(7) 1.0781(10) 1.1632(4) 0.089(3) Uani 1 1 d . . . . .
H18A H 0.8943 1.1586 1.1803 0.134 Uiso 1 1 calc R U . . .
H18B H 0.8971 1.0607 1.116 0.134 Uiso 1 1 calc R U . . .
H18C H 0.9049 1.0089 1.1948 0.134 Uiso 1 1 calc R U . . .
H1 H 1.010(5) 1.202(5) 1.034(3) 0.024(13) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
I1 C2 2.098(6) . ?
P1 O1 1.467(4) . ?
P1 N1 1.629(5) . ?
P1 C7 1.801(6) . ?
P1 C1 1.830(6) . ?
C16 C15 1.542(9) . ?
N1 C13 1.471(7) . ?
C17 C15 1.512(11) . ?
C7 C8 1.374(8) . ?
C7 C12 1.390(8) . ?
C13 C14 1.526(10) . ?
C13 C15 1.557(9) . ?
C1 C6 1.392(8) . ?
C1 C2 1.393(8) . ?
C5 C4 1.370(12) . ?
C5 C6 1.375(10) . ?
C10 C11 1.357(10) . ?
C10 C9 1.374(11) . ?
C15 C18 1.494(10) . ?
C2 C3 1.378(8) . ?
C9 C8 1.374(10) . ?
C4 C3 1.375(12) . ?
C11 C12 1.365(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 113.3(2) . . ?
O1 P1 C7 113.2(3) . . ?
N1 P1 C7 106.7(3) . . ?
O1 P1 C1 107.4(3) . . ?
N1 P1 C1 111.0(3) . . ?
C7 P1 C1 105.0(2) . . ?
C13 N1 P1 124.2(4) . . ?
C8 C7 C12 118.6(5) . . ?
C8 C7 P1 120.3(4) . . ?
C12 C7 P1 120.7(4) . . ?
N1 C13 C14 108.0(5) . . ?
N1 C13 C15 112.2(5) . . ?
C14 C13 C15 113.9(5) . . ?
C6 C1 C2 117.6(5) . . ?
C6 C1 P1 116.3(5) . . ?
C2 C1 P1 126.1(4) . . ?
C4 C5 C6 120.1(7) . . ?
C11 C10 C9 119.5(6) . . ?
C5 C6 C1 121.0(7) . . ?
C18 C15 C17 109.9(7) . . ?
C18 C15 C16 109.3(6) . . ?
C17 C15 C16 107.5(6) . . ?
C18 C15 C13 111.9(6) . . ?
C17 C15 C13 109.7(5) . . ?
C16 C15 C13 108.4(6) . . ?
C3 C2 C1 121.5(6) . . ?
C3 C2 I1 116.1(5) . . ?
C1 C2 I1 122.3(4) . . ?
C8 C9 C10 119.9(6) . . ?
C5 C4 C3 120.6(6) . . ?
C4 C3 C2 119.2(7) . . ?
C9 C8 C7 120.8(6) . . ?
C10 C11 C12 121.4(6) . . ?
C11 C12 C7 119.8(6) . . ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate:hexane'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1406957'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_date             2015-08-20T15:23:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C30 H33 Cl2 N O2 P2 Zn'
_chemical_formula_moiety         'C30 H33 Cl2 N O2 P2 Zn'
_chemical_formula_weight         637.80
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.8384(2)
_cell_length_b                   17.1397(4)
_cell_length_c                   17.4704(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2945.99(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      72.16
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          1.13
_exptl_crystal_size_mid          0.951
_exptl_crystal_size_min          0.256
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3425
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_number            17913
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_max         72.149
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.96
_reflns_Friedel_coverage         0.749
_reflns_number_total             5809
_reflns_number_gt                5285
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and and Mercury (Macrae, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_data_collection       'Bruker Instrument Service v4.2.2'
_computing_cell_refinement       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+1.1057P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00080(10)
_refine_ls_number_reflns         5809
_refine_ls_number_parameters     348
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2121 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(9)
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Zn1 Zn 0.75475(5) 0.48196(2) 0.93454(3) 0.01205(12) Uani 1 1 d . . . . .
P1 P 0.91101(9) 0.58729(5) 0.80973(5) 0.01054(18) Uani 1 1 d . . . . .
Cl2 Cl 0.65599(9) 0.51679(5) 1.04310(5) 0.0215(2) Uani 1 1 d . . . . .
Cl1 Cl 0.64121(9) 0.41557(5) 0.84671(5) 0.0198(2) Uani 1 1 d . . . . .
P2 P 1.07255(9) 0.46046(5) 0.93879(5) 0.01172(19) Uani 1 1 d . . . . .
O2 O 0.9328(2) 0.43153(14) 0.95963(15) 0.0146(5) Uani 1 1 d . . . . .
O1 O 0.8516(2) 0.57207(13) 0.88747(14) 0.0134(5) Uani 1 1 d . . . . .
N1 N 0.8077(3) 0.59180(17) 0.73750(17) 0.0127(6) Uani 1 1 d D . . . .
C2 C 1.1034(3) 0.46386(19) 0.8358(2) 0.0129(7) Uani 1 1 d . . . . .
C1 C 1.0339(3) 0.5129(2) 0.7831(2) 0.0122(7) Uani 1 1 d . . . . .
C7 C 0.9954(3) 0.6803(2) 0.8130(2) 0.0117(7) Uani 1 1 d . . . . .
C19 C 1.1123(3) 0.5545(2) 0.9778(2) 0.0125(7) Uani 1 1 d . . . . .
C8 C 0.9876(4) 0.7253(2) 0.8790(2) 0.0148(8) Uani 1 1 d . . . . .
H8 H 0.9386 0.7068 0.9222 0.018 Uiso 1 1 calc R U . . .
C30 C 1.1404(4) 0.3265(2) 1.0152(2) 0.0130(7) Uani 1 1 d . . . . .
H30 H 1.0451 0.3175 1.0149 0.016 Uiso 1 1 calc R U . . .
C3 C 1.2000(4) 0.4120(2) 0.8073(2) 0.0196(8) Uani 1 1 d . . . . .
H3 H 1.2459 0.3783 0.8419 0.023 Uiso 1 1 calc R U . . .
C25 C 1.1936(4) 0.3936(2) 0.9807(2) 0.0138(8) Uani 1 1 d . . . . .
C12 C 1.0682(4) 0.7077(2) 0.7498(2) 0.0162(8) Uani 1 1 d . . . . .
H12 H 1.0749 0.6767 0.7049 0.019 Uiso 1 1 calc R U . . .
C6 C 1.0653(4) 0.5076(2) 0.7053(2) 0.0158(7) Uani 1 1 d . . . . .
H6 H 1.0188 0.5401 0.6699 0.019 Uiso 1 1 calc R U . . .
C26 C 1.3329(4) 0.4072(2) 0.9827(2) 0.0194(8) Uani 1 1 d . . . . .
H26 H 1.3694 0.4531 0.9603 0.023 Uiso 1 1 calc R U . . .
C29 C 1.2262(4) 0.2732(2) 1.0498(2) 0.0150(7) Uani 1 1 d . . . . .
H29 H 1.1903 0.2273 1.0726 0.018 Uiso 1 1 calc R U . . .
C13 C 0.7237(3) 0.6604(2) 0.7169(2) 0.0132(7) Uani 1 1 d . . . . .
H13 H 0.7531 0.7041 0.7509 0.016 Uiso 1 1 calc R U . . .
C11 C 1.1306(4) 0.7801(2) 0.7526(2) 0.0192(8) Uani 1 1 d . . . . .
H11 H 1.1786 0.7993 0.7093 0.023 Uiso 1 1 calc R U . . .
C15 C 0.5697(4) 0.6475(2) 0.7319(2) 0.0159(8) Uani 1 1 d . . . . .
C20 C 1.0329(4) 0.5844(2) 1.0375(2) 0.0160(7) Uani 1 1 d . . . . .
H20 H 0.9566 0.556 1.0558 0.019 Uiso 1 1 calc R U . . .
C23 C 1.2587(4) 0.6674(2) 0.9856(2) 0.0222(8) Uani 1 1 d . . . . .
H23 H 1.3358 0.6959 0.9685 0.027 Uiso 1 1 calc R U . . .
C24 C 1.2257(4) 0.5963(2) 0.9521(2) 0.0167(8) Uani 1 1 d . . . . .
H24 H 1.2801 0.5761 0.9117 0.02 Uiso 1 1 calc R U . . .
C4 C 1.2311(4) 0.4081(2) 0.7298(2) 0.0238(9) Uani 1 1 d . . . . .
H4 H 1.2988 0.3729 0.712 0.029 Uiso 1 1 calc R U . . .
C28 C 1.3650(4) 0.2872(2) 1.0512(2) 0.0159(7) Uani 1 1 d . . . . .
H28 H 1.4241 0.2508 1.0753 0.019 Uiso 1 1 calc R U . . .
C21 C 1.0665(4) 0.6559(2) 1.0699(2) 0.0203(8) Uani 1 1 d . . . . .
H21 H 1.0123 0.6768 1.1099 0.024 Uiso 1 1 calc R U . . .
C14 C 0.7582(4) 0.6846(2) 0.6351(2) 0.0214(8) Uani 1 1 d . . . . .
H14A H 0.7033 0.73 0.6207 0.032 Uiso 1 1 calc R U . . .
H14B H 0.8549 0.6981 0.6319 0.032 Uiso 1 1 calc R U . . .
H14C H 0.7388 0.6413 0.6001 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0515(4) 0.7975(2) 0.8815(2) 0.0199(8) Uani 1 1 d . . . . .
H9 H 1.0462 0.8283 0.9266 0.024 Uiso 1 1 calc R U . . .
C10 C 1.1226(4) 0.8246(2) 0.8189(2) 0.0191(8) Uani 1 1 d . . . . .
H10 H 1.1663 0.874 0.8211 0.023 Uiso 1 1 calc R U . . .
C5 C 1.1627(4) 0.4558(2) 0.6784(2) 0.0200(8) Uani 1 1 d . . . . .
H5 H 1.1825 0.4531 0.6252 0.024 Uiso 1 1 calc R U . . .
C17 C 0.5145(4) 0.5802(2) 0.6836(3) 0.0271(9) Uani 1 1 d . . . . .
H17A H 0.5301 0.5913 0.6292 0.041 Uiso 1 1 calc R U . . .
H17B H 0.5613 0.5318 0.6976 0.041 Uiso 1 1 calc R U . . .
H17C H 0.4168 0.5744 0.6929 0.041 Uiso 1 1 calc R U . . .
C27 C 1.4181(4) 0.3538(2) 1.0176(2) 0.0200(8) Uani 1 1 d . . . . .
H27 H 1.5133 0.3628 1.0186 0.024 Uiso 1 1 calc R U . . .
C18 C 0.4943(4) 0.7233(2) 0.7120(3) 0.0243(9) Uani 1 1 d . . . . .
H18A H 0.5085 0.7357 0.6578 0.036 Uiso 1 1 calc R U . . .
H18B H 0.3969 0.7165 0.7218 0.036 Uiso 1 1 calc R U . . .
H18C H 0.5294 0.7659 0.7437 0.036 Uiso 1 1 calc R U . . .
C22 C 1.1783(4) 0.6965(2) 1.0442(3) 0.0250(9) Uani 1 1 d . . . . .
H22 H 1.2006 0.7452 1.0669 0.03 Uiso 1 1 calc R U . . .
C16 C 0.5454(4) 0.6300(3) 0.8163(3) 0.0252(9) Uani 1 1 d . . . . .
H16A H 0.5807 0.6731 0.8474 0.038 Uiso 1 1 calc R U . . .
H16B H 0.4477 0.6242 0.8255 0.038 Uiso 1 1 calc R U . . .
H16C H 0.5922 0.5816 0.8302 0.038 Uiso 1 1 calc R U . . .
H1 H 0.787(5) 0.5511(19) 0.714(2) 0.029(13) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Zn1 O1 1.992(2) . ?
Zn1 O2 2.002(2) . ?
Zn1 Cl1 2.2129(10) . ?
Zn1 Cl2 2.2130(10) . ?
P1 O1 1.502(3) . ?
P1 N1 1.622(3) . ?
P1 C7 1.798(4) . ?
P1 C1 1.817(4) . ?
P2 O2 1.506(3) . ?
P2 C19 1.793(4) . ?
P2 C25 1.808(4) . ?
P2 C2 1.826(4) . ?
N1 C13 1.481(4) . ?
N1 H1 0.83(2) . ?
C2 C3 1.393(5) . ?
C2 C1 1.422(5) . ?
C1 C6 1.397(5) . ?
C7 C8 1.389(5) . ?
C7 C12 1.397(5) . ?
C19 C20 1.400(5) . ?
C19 C24 1.401(5) . ?
C8 C9 1.388(5) . ?
C8 H8 0.95 . ?
C30 C29 1.383(5) . ?
C30 C25 1.401(5) . ?
C30 H30 0.95 . ?
C3 C4 1.390(5) . ?
C3 H3 0.95 . ?
C25 C26 1.391(5) . ?
C12 C11 1.386(5) . ?
C12 H12 0.95 . ?
C6 C5 1.387(5) . ?
C6 H6 0.95 . ?
C26 C27 1.383(6) . ?
C26 H26 0.95 . ?
C29 C28 1.387(5) . ?
C29 H29 0.95 . ?
C13 C14 1.526(5) . ?
C13 C15 1.553(5) . ?
C13 H13 1 . ?
C11 C10 1.389(6) . ?
C11 H11 0.95 . ?
C15 C16 1.524(6) . ?
C15 C17 1.528(5) . ?
C15 C18 1.536(5) . ?
C20 C21 1.390(5) . ?
C20 H20 0.95 . ?
C23 C22 1.387(6) . ?
C23 C24 1.391(5) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C4 C5 1.389(5) . ?
C4 H4 0.95 . ?
C28 C27 1.385(5) . ?
C28 H28 0.95 . ?
C21 C22 1.377(6) . ?
C21 H21 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C9 C10 1.380(6) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C5 H5 0.95 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C27 H27 0.95 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C22 H22 0.95 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?

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 Zn1 O2 90.38(10) . . ?
O1 Zn1 Cl1 110.72(8) . . ?
O2 Zn1 Cl1 111.81(8) . . ?
O1 Zn1 Cl2 110.77(7) . . ?
O2 Zn1 Cl2 108.24(8) . . ?
Cl1 Zn1 Cl2 120.75(4) . . ?
O1 P1 N1 117.89(15) . . ?
O1 P1 C7 107.76(16) . . ?
N1 P1 C7 105.77(17) . . ?
O1 P1 C1 111.65(15) . . ?
N1 P1 C1 104.55(16) . . ?
C7 P1 C1 108.81(16) . . ?
O2 P2 C19 113.76(15) . . ?
O2 P2 C25 107.15(16) . . ?
C19 P2 C25 105.80(17) . . ?
O2 P2 C2 113.62(15) . . ?
C19 P2 C2 108.05(16) . . ?
C25 P2 C2 108.03(16) . . ?
P2 O2 Zn1 127.13(14) . . ?
P1 O1 Zn1 133.96(15) . . ?
C13 N1 P1 125.2(2) . . ?
C13 N1 H1 114(3) . . ?
P1 N1 H1 119(3) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 P2 116.4(3) . . ?
C1 C2 P2 125.2(3) . . ?
C6 C1 C2 119.0(3) . . ?
C6 C1 P1 116.3(3) . . ?
C2 C1 P1 124.7(3) . . ?
C8 C7 C12 119.8(3) . . ?
C8 C7 P1 119.6(3) . . ?
C12 C7 P1 120.6(3) . . ?
C20 C19 C24 119.7(3) . . ?
C20 C19 P2 119.4(3) . . ?
C24 C19 P2 120.8(3) . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C29 C30 C25 120.1(3) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
C4 C3 C2 121.9(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C26 C25 C30 119.7(4) . . ?
C26 C25 P2 123.6(3) . . ?
C30 C25 P2 116.7(3) . . ?
C11 C12 C7 120.0(4) . . ?
C11 C12 H12 120 . . ?
C7 C12 H12 120 . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C30 C29 C28 119.7(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
N1 C13 C14 108.7(3) . . ?
N1 C13 C15 113.0(3) . . ?
C14 C13 C15 114.5(3) . . ?
N1 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C15 C13 H13 106.8 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C16 C15 C17 109.3(3) . . ?
C16 C15 C18 108.0(3) . . ?
C17 C15 C18 110.0(3) . . ?
C16 C15 C13 110.2(3) . . ?
C17 C15 C13 111.1(3) . . ?
C18 C15 C13 108.2(3) . . ?
C21 C20 C19 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C19 120.0(4) . . ?
C23 C24 H24 120 . . ?
C19 C24 H24 120 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C27 C28 C29 120.4(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C22 C21 C20 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C27 C28 120.3(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 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
C19 P2 O2 Zn1 60.7(2) . . . . ?
C25 P2 O2 Zn1 177.25(18) . . . . ?
C2 P2 O2 Zn1 -63.5(2) . . . . ?
N1 P1 O1 Zn1 65.2(2) . . . . ?
C7 P1 O1 Zn1 -175.26(19) . . . . ?
C1 P1 O1 Zn1 -55.8(2) . . . . ?
O1 P1 N1 C13 79.7(3) . . . . ?
C7 P1 N1 C13 -40.8(3) . . . . ?
C1 P1 N1 C13 -155.6(3) . . . . ?
O2 P2 C2 C3 -113.0(3) . . . . ?
C19 P2 C2 C3 119.8(3) . . . . ?
C25 P2 C2 C3 5.8(3) . . . . ?
O2 P2 C2 C1 64.8(3) . . . . ?
C19 P2 C2 C1 -62.4(3) . . . . ?
C25 P2 C2 C1 -176.5(3) . . . . ?
C3 C2 C1 C6 -0.3(5) . . . . ?
P2 C2 C1 C6 -178.0(3) . . . . ?
C3 C2 C1 P1 -176.9(3) . . . . ?
P2 C2 C1 P1 5.4(5) . . . . ?
O1 P1 C1 C6 161.7(3) . . . . ?
N1 P1 C1 C6 33.2(3) . . . . ?
C7 P1 C1 C6 -79.5(3) . . . . ?
O1 P1 C1 C2 -21.6(3) . . . . ?
N1 P1 C1 C2 -150.1(3) . . . . ?
C7 P1 C1 C2 97.3(3) . . . . ?
O1 P1 C7 C8 -4.4(3) . . . . ?
N1 P1 C7 C8 122.5(3) . . . . ?
C1 P1 C7 C8 -125.7(3) . . . . ?
O1 P1 C7 C12 175.8(3) . . . . ?
N1 P1 C7 C12 -57.2(3) . . . . ?
C1 P1 C7 C12 54.6(3) . . . . ?
O2 P2 C19 C20 16.0(3) . . . . ?
C25 P2 C19 C20 -101.3(3) . . . . ?
C2 P2 C19 C20 143.2(3) . . . . ?
O2 P2 C19 C24 -167.3(3) . . . . ?
C25 P2 C19 C24 75.3(3) . . . . ?
C2 P2 C19 C24 -40.2(3) . . . . ?
C12 C7 C8 C9 0.3(5) . . . . ?
P1 C7 C8 C9 -179.4(3) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
P2 C2 C3 C4 179.0(3) . . . . ?
C29 C30 C25 C26 -1.4(6) . . . . ?
C29 C30 C25 P2 -178.8(3) . . . . ?
O2 P2 C25 C26 -170.6(3) . . . . ?
C19 P2 C25 C26 -48.9(4) . . . . ?
C2 P2 C25 C26 66.6(4) . . . . ?
O2 P2 C25 C30 6.6(3) . . . . ?
C19 P2 C25 C30 128.3(3) . . . . ?
C2 P2 C25 C30 -116.1(3) . . . . ?
C8 C7 C12 C11 -1.0(5) . . . . ?
P1 C7 C12 C11 178.8(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
P1 C1 C6 C5 176.7(3) . . . . ?
C30 C25 C26 C27 1.2(6) . . . . ?
P2 C25 C26 C27 178.4(3) . . . . ?
C25 C30 C29 C28 1.0(5) . . . . ?
P1 N1 C13 C14 122.6(3) . . . . ?
P1 N1 C13 C15 -109.2(3) . . . . ?
C7 C12 C11 C10 1.2(6) . . . . ?
N1 C13 C15 C16 59.5(4) . . . . ?
C14 C13 C15 C16 -175.4(3) . . . . ?
N1 C13 C15 C17 -61.8(4) . . . . ?
C14 C13 C15 C17 63.3(4) . . . . ?
N1 C13 C15 C18 177.4(3) . . . . ?
C14 C13 C15 C18 -57.5(4) . . . . ?
C24 C19 C20 C21 0.9(5) . . . . ?
P2 C19 C20 C21 177.5(3) . . . . ?
C22 C23 C24 C19 -0.3(6) . . . . ?
C20 C19 C24 C23 -0.3(5) . . . . ?
P2 C19 C24 C23 -176.9(3) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C30 C29 C28 C27 -0.5(6) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C12 C11 C10 C9 -0.8(6) . . . . ?
C1 C6 C5 C4 0.0(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C25 C26 C27 C28 -0.7(6) . . . . ?
C29 C28 C27 C26 0.3(6) . . . . ?
C20 C21 C22 C23 0.3(6) . . . . ?
C24 C23 C22 C21 0.3(6) . . . . ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: slow diffusion of Et2O into a dichloromethane:acetonitrile (1:1)'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1409186'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_date             2015-08-20T15:35:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C21 H32 N O P Sn'
_chemical_formula_moiety         'C21 H32 N O P Sn'
_chemical_formula_weight         464.16
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_Int_Tables_number      96
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/4'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'y+1/2, -x+1/2, z+1/4'
'-y+1/2, x+1/2, z+3/4'
'-y, -x, -z+1/2'

_cell_length_a                   9.3648(2)
_cell_length_b                   9.3648(2)
_cell_length_c                   51.2257(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4492.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      58.99

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1904

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4517
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1292
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_number            13912
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         3.451
_diffrn_reflns_theta_max         58.986
_diffrn_reflns_theta_full        58.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.608
_reflns_number_total             3243
_reflns_number_gt                3196
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Ortep for Windows(Farrugia,2012)and Mercury (Macrae, 2008).'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²+8.9613P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3241
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1147 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(9)
_refine_diff_density_max         3.125
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.148

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.296 0.433 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.026 5.459 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.1368(6) 0.7230(6) 0.94789(9) 0.0196(12) Uani 1 1 d . . . . .
C21 C -0.0180(10) 1.0075(10) 0.96177(15) 0.0308(19) Uani 1 1 d . . . . .
H21A H 0.0434 1.0916 0.9638 0.046 Uiso 1 1 calc R U . . .
H21B H -0.1168 1.0333 0.966 0.046 Uiso 1 1 calc R U . . .
H21C H 0.0143 0.9321 0.9736 0.046 Uiso 1 1 calc R U . . .
C19 C -0.1118(11) 1.1023(11) 0.8999(2) 0.045(3) Uani 1 1 d . . . . .
H19A H -0.0609 1.1926 0.9025 0.068 Uiso 1 1 calc R U . . .
H19B H -0.1105 1.0773 0.8813 0.068 Uiso 1 1 calc R U . . .
H19C H -0.2109 1.1125 0.9058 0.068 Uiso 1 1 calc R U . . .
C20 C -0.1326(10) 0.7506(11) 0.91400(18) 0.036(2) Uani 1 1 d . . . . .
H20A H -0.1204 0.7246 0.8956 0.054 Uiso 1 1 calc R U . . .
H20B H -0.1022 0.6709 0.9251 0.054 Uiso 1 1 calc R U . . .
H20C H -0.2333 0.7721 0.9174 0.054 Uiso 1 1 calc R U . . .
Sn1 Sn -0.00679(5) 0.93281(6) 0.92247(2) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.2582(12) 0.3835(13) 0.9573(3) 0.078(5) Uani 1 1 d . . . . .
H14A H 0.2757 0.3051 0.9695 0.117 Uiso 1 1 calc R U . . .
H14B H 0.1904 0.451 0.965 0.117 Uiso 1 1 calc R U . . .
H14C H 0.2184 0.3451 0.941 0.117 Uiso 1 1 calc R U . . .
P1 P 0.2921(2) 0.7279(2) 0.94110(3) 0.0166(5) Uani 1 1 d . . . . .
C1 C 0.3167(8) 0.8424(9) 0.91291(14) 0.0193(18) Uani 1 1 d . . . . .
C2 C 0.2055(8) 0.9323(9) 0.90554(14) 0.0197(17) Uani 1 1 d . . . . .
N1 N 0.3748(7) 0.5783(7) 0.93307(12) 0.0202(14) Uani 1 1 d . . . . .
H1 H 0.4067 0.569 0.917 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2323(9) 1.0276(9) 0.88484(14) 0.0251(19) Uani 1 1 d . . . . .
H3 H 0.1588 1.0909 0.8794 0.03 Uiso 1 1 calc R U . . .
C8 C 0.5436(10) 0.8091(9) 0.96710(16) 0.026(2) Uani 1 1 d . . . . .
H8 H 0.5941 0.7707 0.9526 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5164(9) 0.3578(10) 0.94152(17) 0.029(2) Uani 1 1 d . . . . .
C17 C 0.6525(11) 0.4465(12) 0.9374(3) 0.057(3) Uani 1 1 d . . . . .
H17A H 0.6783 0.4942 0.9538 0.086 Uiso 1 1 calc R U . . .
H17B H 0.7306 0.3836 0.9319 0.086 Uiso 1 1 calc R U . . .
H17C H 0.6353 0.5184 0.9238 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4707(9) 0.9412(9) 0.87955(15) 0.0238(19) Uani 1 1 d . . . . .
H5 H 0.5594 0.9439 0.8706 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3977(10) 0.4597(9) 0.95147(17) 0.032(2) Uani 1 1 d . . . . .
H13 H 0.4321 0.5023 0.9682 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6172(9) 0.8736(9) 0.98700(15) 0.027(2) Uani 1 1 d . . . . .
H9 H 0.7183 0.8803 0.9862 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3947(8) 0.7994(8) 0.96795(14) 0.0175(16) Uani 1 1 d . . . . .
C12 C 0.3215(9) 0.8551(9) 0.98928(15) 0.0239(19) Uani 1 1 d . . . . .
H12 H 0.2204 0.8493 0.9901 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3971(10) 0.9188(10) 1.00933(16) 0.031(2) Uani 1 1 d . . . . .
H11 H 0.3474 0.956 1.024 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3616(9) 1.0313(9) 0.87227(15) 0.0255(19) Uani 1 1 d . . . . .
H4 H 0.3761 1.097 0.8584 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5447(10) 0.9290(10) 1.00824(16) 0.030(2) Uani 1 1 d . . . . .
H10 H 0.5958 0.9738 1.022 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4505(9) 0.8460(9) 0.90011(14) 0.0212(18) Uani 1 1 d . . . . .
H6 H 0.5256 0.7844 0.9055 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4772(14) 0.2852(14) 0.9166(2) 0.059(3) Uani 1 1 d . . . . .
H16A H 0.4563 0.3572 0.9033 0.088 Uiso 1 1 calc R U . . .
H16B H 0.5568 0.2252 0.9108 0.088 Uiso 1 1 calc R U . . .
H16C H 0.3925 0.2256 0.9194 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5485(14) 0.2449(12) 0.9621(2) 0.058(3) Uani 1 1 d . . . . .
H18A H 0.5744 0.2918 0.9786 0.087 Uiso 1 1 calc R U . . .
H18B H 0.4638 0.1853 0.9649 0.087 Uiso 1 1 calc R U . . .
H18C H 0.628 0.185 0.9563 0.087 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 P1 1.496(6) . ?
C21 Sn1 2.134(8) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C19 Sn1 2.196(8) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 Sn1 2.118(10) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
Sn1 C2 2.169(8) . ?
C14 C13 1.519(15) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
P1 N1 1.653(6) . ?
P1 C7 1.807(8) . ?
P1 C1 1.813(8) . ?
C1 C2 1.392(12) . ?
C1 C6 1.414(11) . ?
C2 C3 1.408(12) . ?
N1 C13 1.472(11) . ?
N1 H1 0.88 . ?
C3 C4 1.372(12) . ?
C3 H3 0.95 . ?
C8 C9 1.371(12) . ?
C8 C7 1.397(12) . ?
C8 H8 0.95 . ?
C15 C16 1.491(14) . ?
C15 C18 1.525(13) . ?
C15 C17 1.536(14) . ?
C15 C13 1.551(13) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C5 C4 1.376(14) . ?
C5 C6 1.393(12) . ?
C5 H5 0.95 . ?
C13 H13 1 . ?
C9 C10 1.384(12) . ?
C9 H9 0.95 . ?
C7 C12 1.391(11) . ?
C12 C11 1.383(12) . ?
C12 H12 0.95 . ?
C11 C10 1.386(14) . ?
C11 H11 0.95 . ?
C4 H4 0.95 . ?
C10 H10 0.95 . ?
C6 H6 0.95 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?

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
Sn1 C21 H21A 109.5 . . ?
Sn1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Sn1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Sn1 C19 H19A 109.5 . . ?
Sn1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Sn1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Sn1 C20 H20A 109.5 . . ?
Sn1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Sn1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 Sn1 C21 115.5(4) . . ?
C20 Sn1 C2 115.2(3) . . ?
C21 Sn1 C2 115.0(3) . . ?
C20 Sn1 C19 103.0(4) . . ?
C21 Sn1 C19 103.7(4) . . ?
C2 Sn1 C19 101.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 P1 N1 119.2(3) . . ?
O1 P1 C7 110.6(3) . . ?
N1 P1 C7 104.8(4) . . ?
O1 P1 C1 109.1(3) . . ?
N1 P1 C1 104.1(4) . . ?
C7 P1 C1 108.6(4) . . ?
C2 C1 C6 121.5(7) . . ?
C2 C1 P1 118.6(6) . . ?
C6 C1 P1 119.7(6) . . ?
C1 C2 C3 117.1(8) . . ?
C1 C2 Sn1 125.3(6) . . ?
C3 C2 Sn1 117.6(6) . . ?
C13 N1 P1 123.3(5) . . ?
C13 N1 H1 118.4 . . ?
P1 N1 H1 118.4 . . ?
C4 C3 C2 121.8(8) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C9 C8 C7 120.5(8) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C16 C15 C18 109.0(9) . . ?
C16 C15 C17 109.5(9) . . ?
C18 C15 C17 107.9(9) . . ?
C16 C15 C13 112.6(8) . . ?
C18 C15 C13 109.9(8) . . ?
C17 C15 C13 107.8(8) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 119.8(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C13 C14 110.8(9) . . ?
N1 C13 C15 111.0(7) . . ?
C14 C13 C15 113.1(8) . . ?
N1 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C15 C13 H13 107.2 . . ?
C8 C9 C10 120.2(8) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C12 C7 C8 119.4(8) . . ?
C12 C7 P1 118.4(6) . . ?
C8 C7 P1 122.1(6) . . ?
C11 C12 C7 119.5(8) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C12 C11 C10 120.7(8) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C3 C4 C5 120.8(8) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C9 C10 C11 119.7(8) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C5 C6 C1 119.1(8) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 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
O1 P1 C1 C2 14.7(7) . . . . ?
N1 P1 C1 C2 142.9(6) . . . . ?
C7 P1 C1 C2 -105.8(7) . . . . ?
O1 P1 C1 C6 -169.7(6) . . . . ?
N1 P1 C1 C6 -41.5(7) . . . . ?
C7 P1 C1 C6 69.7(7) . . . . ?
C6 C1 C2 C3 -0.3(12) . . . . ?
P1 C1 C2 C3 175.2(6) . . . . ?
C6 C1 C2 Sn1 177.7(6) . . . . ?
P1 C1 C2 Sn1 -6.9(10) . . . . ?
O1 P1 N1 C13 -66.0(8) . . . . ?
C7 P1 N1 C13 58.3(7) . . . . ?
C1 P1 N1 C13 172.3(7) . . . . ?
C1 C2 C3 C4 0.5(12) . . . . ?
Sn1 C2 C3 C4 -177.6(6) . . . . ?
P1 N1 C13 C14 71.5(10) . . . . ?
P1 N1 C13 C15 -162.0(6) . . . . ?
C16 C15 C13 N1 -64.0(11) . . . . ?
C18 C15 C13 N1 174.3(8) . . . . ?
C17 C15 C13 N1 56.9(10) . . . . ?
C16 C15 C13 C14 61.2(12) . . . . ?
C18 C15 C13 C14 -60.6(12) . . . . ?
C17 C15 C13 C14 -177.9(10) . . . . ?
C7 C8 C9 C10 0.5(13) . . . . ?
C9 C8 C7 C12 -0.4(13) . . . . ?
C9 C8 C7 P1 175.1(6) . . . . ?
O1 P1 C7 C12 -7.5(7) . . . . ?
N1 P1 C7 C12 -137.0(6) . . . . ?
C1 P1 C7 C12 112.2(7) . . . . ?
O1 P1 C7 C8 176.9(7) . . . . ?
N1 P1 C7 C8 47.4(8) . . . . ?
C1 P1 C7 C8 -63.4(8) . . . . ?
C8 C7 C12 C11 -0.1(12) . . . . ?
P1 C7 C12 C11 -175.8(7) . . . . ?
C7 C12 C11 C10 0.6(14) . . . . ?
C2 C3 C4 C5 0.0(13) . . . . ?
C6 C5 C4 C3 -0.8(13) . . . . ?
C8 C9 C10 C11 0.1(14) . . . . ?
C12 C11 C10 C9 -0.6(15) . . . . ?
C4 C5 C6 C1 1.0(12) . . . . ?
C2 C1 C6 C5 -0.5(12) . . . . ?
P1 C1 C6 C5 -175.9(6) . . . . ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate:hexane'
