# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_n172

_audit_creation_date             2014-01-09T00:36:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H33 N O P2 S, C2 H3 N'
_chemical_formula_sum            'C32 H36 N2 O P2 S'
_chemical_formula_weight         558.63
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1412(13)
_cell_length_b                   9.8502(17)
_cell_length_c                   17.910(4)
_cell_angle_alpha                93.263(18)
_cell_angle_beta                 94.429(17)
_cell_angle_gamma                109.92(2)
_cell_volume                     1505.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10898
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      26
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.095
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 0 0.123
-1 0 0 0.099
0 0 1 0.066
0 0 -1 0.029
0 -3 -4 0.078
0 3 4 0.051

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS; Sheldrick, 1996
;
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.951

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_number            10185
_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       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.519
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             5486
_reflns_number_gt                3173
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5486
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   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'
S S 0.1246 0.1234 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
P2 P 0.85122(9) 0.65923(8) 0.86203(4) 0.0341(2) Uani 1 d . .
P1 P 1.08782(9) 0.71873(8) 0.71283(4) 0.0342(2) Uani 1 d . .
S1 S 0.74315(10) 0.75304(9) 0.79571(5) 0.0489(2) Uani 1 d . .
O1 O 0.9581(2) 0.5786(2) 0.70586(10) 0.0422(5) Uani 1 d . .
N1 N 1.2324(3) 0.7164(2) 0.66382(12) 0.0374(6) Uani 1 d . .
C1 C 1.1624(3) 0.7654(3) 0.81267(15) 0.0337(7) Uani 1 d . .
C2 C 1.0671(3) 0.7354(3) 0.87298(15) 0.0320(7) Uani 1 d . .
C3 C 1.1412(3) 0.7616(3) 0.94617(16) 0.0396(7) Uani 1 d . .
H3 H 1.0801 0.7409 0.9861 0.047 Uiso 1 calc . .
C4 C 1.3031(4) 0.8177(3) 0.96157(17) 0.0447(8) Uani 1 d . .
H4 H 1.3488 0.8342 1.011 0.054 Uiso 1 calc . .
C6 C 1.3230(3) 0.8229(3) 0.83026(16) 0.0442(8) Uani 1 d . .
H6 H 1.3861 0.8457 0.7912 0.053 Uiso 1 calc . .
C7 C 0.7956(3) 0.6755(3) 0.95706(15) 0.0349(7) Uani 1 d . .
C5 C 1.3944(4) 0.8483(3) 0.90379(17) 0.0485(8) Uani 1 d . .
H5 H 1.5028 0.8856 0.9133 0.058 Uiso 1 calc . .
C8 C 0.8057(4) 0.8113(3) 0.98856(18) 0.0530(9) Uani 1 d . .
H8 H 0.8447 0.8919 0.9618 0.064 Uiso 1 calc . .
C9 C 0.7590(4) 0.8282(4) 1.05897(19) 0.0635(10) Uani 1 d . .
H9 H 0.7669 0.9196 1.0795 0.076 Uiso 1 calc . .
C10 C 0.7006(4) 0.7091(4) 1.09835(19) 0.0603(10) Uani 1 d . .
H10 H 0.6696 0.7203 1.1459 0.072 Uiso 1 calc . .
C11 C 0.6877(4) 0.5740(4) 1.06840(18) 0.0547(9) Uani 1 d . .
H11 H 0.647 0.4936 1.0952 0.066 Uiso 1 calc . .
C12 C 0.7357(4) 0.5576(3) 0.99780(16) 0.0450(8) Uani 1 d . .
H12 H 0.7274 0.4658 0.9777 0.054 Uiso 1 calc . .
C13 C 0.8027(3) 0.4659(3) 0.84062(15) 0.0354(7) Uani 1 d . .
C14 C 0.9047(4) 0.3956(3) 0.86288(17) 0.0458(8) Uani 1 d . .
H14 H 1.0022 0.4492 0.8879 0.055 Uiso 1 calc . .
C15 C 0.8647(4) 0.2487(3) 0.84866(19) 0.0547(9) Uani 1 d . .
H15 H 0.9347 0.2038 0.8643 0.066 Uiso 1 calc . .
C16 C 0.7228(5) 0.1680(4) 0.8117(2) 0.0641(11) Uani 1 d . .
H16 H 0.6956 0.0682 0.8021 0.077 Uiso 1 calc . .
C17 C 0.6197(4) 0.2365(4) 0.7886(2) 0.0740(12) Uani 1 d . .
H17 H 0.5228 0.1823 0.7631 0.089 Uiso 1 calc . .
C18 C 0.6594(4) 0.3844(3) 0.80301(19) 0.0571(9) Uani 1 d . .
H18 H 0.5893 0.4293 0.7873 0.069 Uiso 1 calc . .
C19 C 1.0341(3) 0.8676(3) 0.68153(16) 0.0375(7) Uani 1 d . .
C20 C 0.9425(4) 0.8430(4) 0.61304(18) 0.0488(8) Uani 1 d . .
H20 H 0.9151 0.7537 0.5853 0.059 Uiso 1 calc . .
C21 C 0.8914(4) 0.9489(4) 0.5855(2) 0.0627(10) Uani 1 d . .
H21 H 0.8301 0.9311 0.5396 0.075 Uiso 1 calc . .
C22 C 0.9317(5) 1.0800(4) 0.6262(2) 0.0693(11) Uani 1 d . .
H22 H 0.8968 1.1514 0.6081 0.083 Uiso 1 calc . .
C23 C 1.0227(5) 1.1075(4) 0.6934(2) 0.0656(11) Uani 1 d . .
H23 H 1.0498 1.1975 0.7204 0.079 Uiso 1 calc . .
C24 C 1.0750(4) 1.0014(3) 0.72144(18) 0.0524(9) Uani 1 d . .
H24 H 1.1374 1.0207 0.767 0.063 Uiso 1 calc . .
C25 C 1.2607(4) 0.5772(3) 0.64655(17) 0.0460(8) Uani 1 d . .
H25 H 1.3585 0.6025 0.6229 0.055 Uiso 1 calc . .
C26 C 1.2867(4) 0.5074(3) 0.71767(19) 0.0603(10) Uani 1 d . .
H26A H 1.3675 0.5768 0.7516 0.09 Uiso 1 calc . .
H26B H 1.3175 0.4257 0.7049 0.09 Uiso 1 calc . .
H26C H 1.1915 0.4755 0.7413 0.09 Uiso 1 calc . .
C27 C 1.1341(4) 0.4721(4) 0.5896(2) 0.0685(11) Uani 1 d . .
H27A H 1.1215 0.5205 0.5458 0.103 Uiso 1 calc . .
H27B H 1.037 0.4391 0.6117 0.103 Uiso 1 calc . .
H27C H 1.1641 0.3906 0.5755 0.103 Uiso 1 calc . .
C28 C 1.3310(4) 0.8452(3) 0.62860(17) 0.0450(8) Uani 1 d . .
H28 H 1.308 0.929 0.6495 0.054 Uiso 1 calc . .
C29 C 1.2897(4) 0.8325(4) 0.54376(18) 0.0743(12) Uani 1 d . .
H29A H 1.1793 0.8116 0.533 0.111 Uiso 1 calc . .
H29B H 1.3178 0.7558 0.5207 0.111 Uiso 1 calc . .
H29C H 1.346 0.9222 0.5242 0.111 Uiso 1 calc . .
C30 C 1.5061(4) 0.8790(4) 0.6457(2) 0.0660(11) Uani 1 d . .
H30A H 1.5319 0.8863 0.6991 0.099 Uiso 1 calc . .
H30B H 1.5619 0.9692 0.6265 0.099 Uiso 1 calc . .
H30C H 1.5347 0.8028 0.6224 0.099 Uiso 1 calc . .
C2A C 0.3577(6) 0.5312(6) 0.3939(3) 0.130(2) Uani 1 d . .
H2A1 H 0.3712 0.475 0.3511 0.194 Uiso 1 calc . .
H2A2 H 0.2712 0.5632 0.382 0.194 Uiso 1 calc . .
H2A3 H 0.3374 0.4727 0.4356 0.194 Uiso 1 calc . .
C1A C 0.4884(7) 0.6468(8) 0.4122(4) 0.149(3) Uani 1 d . .
N1A N 0.5919(7) 0.7581(8) 0.4189(4) 0.224(4) Uani 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
P2 C13 1.812(3) . ?
P2 C7 1.828(3) . ?
P2 C2 1.847(3) . ?
P2 S1 1.9510(12) . ?
P1 O1 1.4732(19) . ?
P1 N1 1.648(2) . ?
P1 C19 1.802(3) . ?
P1 C1 1.838(3) . ?
N1 C28 1.489(3) . ?
N1 C25 1.499(4) . ?
C1 C6 1.384(4) . ?
C1 C2 1.421(4) . ?
C2 C3 1.396(4) . ?
C3 C4 1.391(4) . ?
C3 H3 0.93 . ?
C4 C5 1.362(4) . ?
C4 H4 0.93 . ?
C6 C5 1.393(4) . ?
C6 H6 0.93 . ?
C7 C12 1.381(4) . ?
C7 C8 1.391(4) . ?
C5 H5 0.93 . ?
C8 C9 1.381(4) . ?
C8 H8 0.93 . ?
C9 C10 1.373(4) . ?
C9 H9 0.93 . ?
C10 C11 1.369(4) . ?
C10 H10 0.93 . ?
C11 C12 1.389(4) . ?
C11 H11 0.93 . ?
C12 H12 0.93 . ?
C13 C18 1.378(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.93 . ?
C15 C16 1.363(5) . ?
C15 H15 0.93 . ?
C16 C17 1.386(5) . ?
C16 H16 0.93 . ?
C17 C18 1.380(4) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C24 1.380(4) . ?
C19 C20 1.391(4) . ?
C20 C21 1.380(4) . ?
C20 H20 0.93 . ?
C21 C22 1.365(5) . ?
C21 H21 0.93 . ?
C22 C23 1.366(5) . ?
C22 H22 0.93 . ?
C23 C24 1.391(5) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C26 1.522(4) . ?
C25 C27 1.527(4) . ?
C25 H25 0.98 . ?
C26 H26A 0.96 . ?
C26 H26B 0.96 . ?
C26 H26C 0.96 . ?
C27 H27A 0.96 . ?
C27 H27B 0.96 . ?
C27 H27C 0.96 . ?
C28 C30 1.522(4) . ?
C28 C29 1.525(4) . ?
C28 H28 0.98 . ?
C29 H29A 0.96 . ?
C29 H29B 0.96 . ?
C29 H29C 0.96 . ?
C30 H30A 0.96 . ?
C30 H30B 0.96 . ?
C30 H30C 0.96 . ?
C2A C1A 1.342(7) . ?
C2A H2A1 0.96 . ?
C2A H2A2 0.96 . ?
C2A H2A3 0.96 . ?
C1A N1A 1.171(7) . ?

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
C13 P2 C7 104.10(13) . . ?
C13 P2 C2 105.31(13) . . ?
C7 P2 C2 104.65(13) . . ?
C13 P2 S1 115.92(10) . . ?
C7 P2 S1 108.85(10) . . ?
C2 P2 S1 116.74(9) . . ?
O1 P1 N1 113.06(12) . . ?
O1 P1 C19 114.47(13) . . ?
N1 P1 C19 104.79(12) . . ?
O1 P1 C1 108.21(12) . . ?
N1 P1 C1 109.10(13) . . ?
C19 P1 C1 106.94(13) . . ?
C28 N1 C25 116.5(2) . . ?
C28 N1 P1 123.1(2) . . ?
C25 N1 P1 120.22(19) . . ?
C6 C1 C2 117.9(3) . . ?
C6 C1 P1 117.6(2) . . ?
C2 C1 P1 124.3(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 P2 117.0(2) . . ?
C1 C2 P2 124.9(2) . . ?
C4 C3 C2 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C1 C6 C5 123.0(3) . . ?
C1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C12 C7 C8 118.1(3) . . ?
C12 C7 P2 122.9(2) . . ?
C8 C7 P2 118.9(2) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 121.0(3) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 P2 119.9(2) . . ?
C14 C13 P2 121.7(2) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C24 C19 C20 118.6(3) . . ?
C24 C19 P1 124.5(2) . . ?
C20 C19 P1 116.9(2) . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 119.9(3) . . ?
C19 C24 H24 120 . . ?
C23 C24 H24 120 . . ?
N1 C25 C26 111.9(3) . . ?
N1 C25 C27 112.7(3) . . ?
C26 C25 C27 112.3(3) . . ?
N1 C25 H25 106.5 . . ?
C26 C25 H25 106.5 . . ?
C27 C25 H25 106.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 C30 114.0(3) . . ?
N1 C28 C29 112.1(3) . . ?
C30 C28 C29 109.5(3) . . ?
N1 C28 H28 106.9 . . ?
C30 C28 H28 106.9 . . ?
C29 C28 H28 106.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
N1A C1A C2A 168.7(10) . . ?

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 N1 C28 147.4(2) . . . . ?
C19 P1 N1 C28 22.1(3) . . . . ?
C1 P1 N1 C28 -92.2(2) . . . . ?
O1 P1 N1 C25 -26.7(2) . . . . ?
C19 P1 N1 C25 -152.0(2) . . . . ?
C1 P1 N1 C25 93.7(2) . . . . ?
O1 P1 C1 C6 138.0(2) . . . . ?
N1 P1 C1 C6 14.6(3) . . . . ?
C19 P1 C1 C6 -98.2(2) . . . . ?
O1 P1 C1 C2 -36.6(3) . . . . ?
N1 P1 C1 C2 -160.0(2) . . . . ?
C19 P1 C1 C2 87.1(3) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
P1 C1 C2 C3 172.7(2) . . . . ?
C6 C1 C2 P2 179.9(2) . . . . ?
P1 C1 C2 P2 -5.5(4) . . . . ?
C13 P2 C2 C3 -97.9(2) . . . . ?
C7 P2 C2 C3 11.5(2) . . . . ?
S1 P2 C2 C3 131.9(2) . . . . ?
C13 P2 C2 C1 80.3(3) . . . . ?
C7 P2 C2 C1 -170.3(2) . . . . ?
S1 P2 C2 C1 -49.9(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
P2 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C2 C1 C6 C5 2.0(4) . . . . ?
P1 C1 C6 C5 -173.0(3) . . . . ?
C13 P2 C7 C12 1.7(3) . . . . ?
C2 P2 C7 C12 -108.6(3) . . . . ?
S1 P2 C7 C12 125.9(2) . . . . ?
C13 P2 C7 C8 -174.7(2) . . . . ?
C2 P2 C7 C8 75.0(3) . . . . ?
S1 P2 C7 C8 -50.5(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C1 C6 C5 C4 -1.1(5) . . . . ?
C12 C7 C8 C9 0.7(5) . . . . ?
P2 C7 C8 C9 177.3(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C8 C7 C12 C11 -0.3(5) . . . . ?
P2 C7 C12 C11 -176.8(2) . . . . ?
C10 C11 C12 C7 -0.4(5) . . . . ?
C7 P2 C13 C18 93.8(3) . . . . ?
C2 P2 C13 C18 -156.3(3) . . . . ?
S1 P2 C13 C18 -25.7(3) . . . . ?
C7 P2 C13 C14 -84.4(3) . . . . ?
C2 P2 C13 C14 25.4(3) . . . . ?
S1 P2 C13 C14 156.1(2) . . . . ?
C18 C13 C14 C15 -0.6(5) . . . . ?
P2 C13 C14 C15 177.7(2) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C14 C13 C18 C17 0.4(5) . . . . ?
P2 C13 C18 C17 -178.0(3) . . . . ?
C16 C17 C18 C13 0.1(6) . . . . ?
O1 P1 C19 C24 132.6(3) . . . . ?
N1 P1 C19 C24 -102.9(3) . . . . ?
C1 P1 C19 C24 12.8(3) . . . . ?
O1 P1 C19 C20 -46.0(3) . . . . ?
N1 P1 C19 C20 78.4(2) . . . . ?
C1 P1 C19 C20 -165.9(2) . . . . ?
C24 C19 C20 C21 -0.8(5) . . . . ?
P1 C19 C20 C21 178.0(3) . . . . ?
C19 C20 C21 C22 0.0(5) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
C20 C19 C24 C23 0.9(5) . . . . ?
P1 C19 C24 C23 -177.7(3) . . . . ?
C22 C23 C24 C19 -0.4(5) . . . . ?
C28 N1 C25 C26 128.4(3) . . . . ?
P1 N1 C25 C26 -57.1(3) . . . . ?
C28 N1 C25 C27 -104.0(3) . . . . ?
P1 N1 C25 C27 70.5(3) . . . . ?
C25 N1 C28 C30 -55.5(3) . . . . ?
P1 N1 C28 C30 130.1(3) . . . . ?
C25 N1 C28 C29 69.6(3) . . . . ?
P1 N1 C28 C29 -104.7(3) . . . . ?

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
C6 H6 N1 0.93 2.6 3.057(4) 110.9 .
C18 H18 S1 0.93 3 3.459(3) 111.8 .
C27 H27B O1 0.96 2.42 3.073(4) 125.1 .
C2A H2A2 O1 0.96 2.46 3.091(5) 122.9 2_666

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 989179'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_n178

_audit_creation_date             2013-12-10T22:51:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H33 Cl2 N1 O2 P2 Zn1'
_chemical_formula_sum            'C30 H33 Cl2 N1 O2 P2 Zn1'
_chemical_formula_weight         637.78
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7651(4)
_cell_length_b                   15.5932(5)
_cell_length_c                   17.9816(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.666(3)
_cell_angle_gamma                90
_cell_volume                     3017.16(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3769
_cell_measurement_theta_min      1.8887
_cell_measurement_theta_max      29.4913
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1287
_exptl_crystal_size_mid          0.0933
_exptl_crystal_size_min          0.0537
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0269
-1 0 0 0.0269
0 -1 1 0.04
0 1 -1 0.0533
0 1 1 0.0701
0 -1 -1 0.043
1 2 0 0.06
-1 -2 0 0.0394

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.88704
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4186
_diffrn_orient_matrix_ub_11      -0.0547252
_diffrn_orient_matrix_ub_12      0.025377
_diffrn_orient_matrix_ub_13      -0.0002164
_diffrn_orient_matrix_ub_21      0.0165074
_diffrn_orient_matrix_ub_22      0.0182532
_diffrn_orient_matrix_ub_23      -0.0344643
_diffrn_orient_matrix_ub_31      -0.0328654
_diffrn_orient_matrix_ub_32      -0.0330287
_diffrn_orient_matrix_ub_33      -0.0192111
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.1466
_diffrn_reflns_number            12064
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             5516
_reflns_number_gt                4050
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SUPERFLIP(Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury(Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5516
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.69
_refine_diff_density_rms         0.204

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.32202(4) 0.62850(3) 0.21985(2) 0.01964(16) Uani 1 d . .
Cl2 Cl 0.51917(11) 0.63631(7) 0.19112(7) 0.0377(3) Uani 1 d . .
Cl1 Cl 0.18955(12) 0.62448(7) 0.12336(6) 0.0366(3) Uani 1 d . .
P1 P 0.26950(9) 0.75979(6) 0.36741(5) 0.0162(2) Uani 1 d . .
P2 P 0.20089(10) 0.53831(6) 0.35739(5) 0.0174(2) Uani 1 d . .
O1 O 0.2777(2) 0.71593(17) 0.29372(14) 0.0206(6) Uani 1 d . .
O2 O 0.2819(2) 0.53625(16) 0.29064(13) 0.0207(6) Uani 1 d . .
N1 N 0.3727(3) 0.8355(2) 0.38547(17) 0.0187(7) Uani 1 d . .
C1 C 0.2901(3) 0.6831(2) 0.4439(2) 0.0177(9) Uani 1 d . .
C2 C 0.2681(4) 0.5937(3) 0.4389(2) 0.0190(9) Uani 1 d . .
C3 C 0.2868(4) 0.5437(3) 0.5023(2) 0.0286(10) Uani 1 d . .
H3 H 0.2722 0.485 0.4994 0.034 Uiso 1 calc . .
C4 C 0.3268(5) 0.5791(3) 0.5698(2) 0.0352(12) Uani 1 d . .
H4 H 0.3412 0.5441 0.611 0.042 Uiso 1 calc . .
C5 C 0.3448(4) 0.6659(3) 0.5750(2) 0.0322(11) Uani 1 d . .
H5 H 0.3688 0.6905 0.6203 0.039 Uiso 1 calc . .
C6 C 0.3270(4) 0.7170(3) 0.5126(2) 0.0231(9) Uani 1 d . .
H6 H 0.34 0.7758 0.5168 0.028 Uiso 1 calc . .
C7 C 0.1749(4) 0.4278(2) 0.3815(2) 0.0205(9) Uani 1 d . .
C8 C 0.2742(4) 0.3710(3) 0.3776(2) 0.0289(10) Uani 1 d . .
H8 H 0.3533 0.3915 0.368 0.035 Uiso 1 calc . .
C9 C 0.2554(5) 0.2838(3) 0.3880(3) 0.0415(13) Uani 1 d . .
H9 H 0.3218 0.2458 0.386 0.05 Uiso 1 calc . .
C10 C 0.1374(6) 0.2539(3) 0.4013(3) 0.0458(15) Uani 1 d . .
H10 H 0.125 0.1954 0.4079 0.055 Uiso 1 calc . .
C11 C 0.0379(5) 0.3090(3) 0.4051(2) 0.0391(12) Uani 1 d . .
H11 H -0.0412 0.2879 0.4137 0.047 Uiso 1 calc . .
C12 C 0.0567(4) 0.3965(3) 0.3958(2) 0.0277(10) Uani 1 d . .
H12 H -0.0098 0.4342 0.3992 0.033 Uiso 1 calc . .
C13 C 0.0493(4) 0.5842(2) 0.3429(2) 0.0183(9) Uani 1 d . .
C14 C -0.0164(4) 0.6160(2) 0.4022(2) 0.0245(10) Uani 1 d . .
H14 H 0.022 0.6195 0.4491 0.029 Uiso 1 calc . .
C15 C -0.1391(4) 0.6425(3) 0.3922(3) 0.0315(11) Uani 1 d . .
H15 H -0.1826 0.6636 0.4322 0.038 Uiso 1 calc . .
C16 C -0.1955(4) 0.6373(3) 0.3229(3) 0.0352(12) Uani 1 d . .
H16 H -0.278 0.654 0.316 0.042 Uiso 1 calc . .
C17 C -0.1303(4) 0.6074(3) 0.2632(3) 0.0319(11) Uani 1 d . .
H17 H -0.1686 0.6058 0.2162 0.038 Uiso 1 calc . .
C18 C -0.0082(4) 0.5797(3) 0.2724(2) 0.0266(10) Uani 1 d . .
H18 H 0.0346 0.5584 0.2322 0.032 Uiso 1 calc . .
C19 C 0.1185(4) 0.8072(2) 0.3736(2) 0.0167(9) Uani 1 d . .
C20 C 0.0439(4) 0.8133(2) 0.3096(2) 0.0208(9) Uani 1 d . .
H20 H 0.0694 0.7888 0.2655 0.025 Uiso 1 calc . .
C21 C -0.0682(4) 0.8559(3) 0.3115(2) 0.0286(10) Uani 1 d . .
H21 H -0.1175 0.8603 0.2683 0.034 Uiso 1 calc . .
C22 C -0.1081(4) 0.8923(3) 0.3766(3) 0.0287(10) Uani 1 d . .
H22 H -0.1826 0.9224 0.377 0.034 Uiso 1 calc . .
C23 C -0.0364(4) 0.8835(3) 0.4416(2) 0.0282(10) Uani 1 d . .
H23 H -0.0639 0.9063 0.4859 0.034 Uiso 1 calc . .
C24 C 0.0756(4) 0.8409(3) 0.4401(2) 0.0211(9) Uani 1 d . .
H24 H 0.1231 0.8345 0.4838 0.025 Uiso 1 calc . .
C25 C 0.5056(4) 0.8085(3) 0.3959(3) 0.0310(11) Uani 1 d . .
H25 H 0.506 0.7476 0.4093 0.037 Uiso 1 calc . .
C26 C 0.5672(4) 0.8574(3) 0.4603(3) 0.0456(14) Uani 1 d . .
H26A H 0.5179 0.8519 0.5037 0.068 Uiso 1 calc . .
H26B H 0.574 0.9169 0.4473 0.068 Uiso 1 calc . .
H26C H 0.6486 0.8344 0.4706 0.068 Uiso 1 calc . .
C27 C 0.5780(4) 0.8180(3) 0.3251(3) 0.0400(12) Uani 1 d . .
H27A H 0.5354 0.7882 0.2852 0.06 Uiso 1 calc . .
H27B H 0.6596 0.7942 0.3326 0.06 Uiso 1 calc . .
H27C H 0.5847 0.8777 0.3126 0.06 Uiso 1 calc . .
C28 C 0.3587(4) 0.9257(2) 0.3570(2) 0.0204(9) Uani 1 d . .
H28 H 0.4423 0.9506 0.361 0.025 Uiso 1 calc . .
C29 C 0.3221(4) 0.9301(3) 0.2744(2) 0.0284(10) Uani 1 d . .
H29A H 0.3738 0.892 0.2471 0.043 Uiso 1 calc . .
H29B H 0.3326 0.9877 0.2568 0.043 Uiso 1 calc . .
H29C H 0.2367 0.9134 0.2675 0.043 Uiso 1 calc . .
C30 C 0.2784(4) 0.9825(3) 0.4049(2) 0.0310(11) Uani 1 d . .
H30A H 0.305 0.9771 0.4562 0.046 Uiso 1 calc . .
H30B H 0.1931 0.965 0.3994 0.046 Uiso 1 calc . .
H30C H 0.2863 1.0411 0.3895 0.046 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 1.972(3) . ?
Zn1 O2 1.977(3) . ?
Zn1 Cl2 2.2023(13) . ?
Zn1 Cl1 2.2146(11) . ?
P1 O1 1.496(3) . ?
P1 N1 1.647(3) . ?
P1 C19 1.792(4) . ?
P1 C1 1.832(4) . ?
P2 O2 1.504(3) . ?
P2 C13 1.794(4) . ?
P2 C7 1.800(4) . ?
P2 C2 1.832(4) . ?
N1 C25 1.498(5) . ?
N1 C28 1.502(5) . ?
C1 C6 1.390(5) . ?
C1 C2 1.416(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.390(5) . ?
C3 H3 0.93 . ?
C4 C5 1.371(6) . ?
C4 H4 0.93 . ?
C5 C6 1.384(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.392(6) . ?
C7 C12 1.395(6) . ?
C8 C9 1.388(6) . ?
C8 H8 0.93 . ?
C9 C10 1.380(7) . ?
C9 H9 0.93 . ?
C10 C11 1.377(7) . ?
C10 H10 0.93 . ?
C11 C12 1.390(6) . ?
C11 H11 0.93 . ?
C12 H12 0.93 . ?
C13 C14 1.388(6) . ?
C13 C18 1.396(5) . ?
C14 C15 1.391(6) . ?
C14 H14 0.93 . ?
C15 C16 1.374(6) . ?
C15 H15 0.93 . ?
C16 C17 1.380(7) . ?
C16 H16 0.93 . ?
C17 C18 1.388(6) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C20 1.387(5) . ?
C19 C24 1.398(5) . ?
C20 C21 1.378(6) . ?
C20 H20 0.93 . ?
C21 C22 1.381(6) . ?
C21 H21 0.93 . ?
C22 C23 1.388(6) . ?
C22 H22 0.93 . ?
C23 C24 1.377(6) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C27 1.521(6) . ?
C25 C26 1.523(6) . ?
C25 H25 0.98 . ?
C26 H26A 0.96 . ?
C26 H26B 0.96 . ?
C26 H26C 0.96 . ?
C27 H27A 0.96 . ?
C27 H27B 0.96 . ?
C27 H27C 0.96 . ?
C28 C30 1.523(6) . ?
C28 C29 1.527(5) . ?
C28 H28 0.98 . ?
C29 H29A 0.96 . ?
C29 H29B 0.96 . ?
C29 H29C 0.96 . ?
C30 H30A 0.96 . ?
C30 H30B 0.96 . ?
C30 H30C 0.96 . ?

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 90.44(11) . . ?
O1 Zn1 Cl2 111.93(9) . . ?
O2 Zn1 Cl2 114.92(9) . . ?
O1 Zn1 Cl1 112.62(8) . . ?
O2 Zn1 Cl1 109.65(8) . . ?
Cl2 Zn1 Cl1 114.88(5) . . ?
O1 P1 N1 116.47(17) . . ?
O1 P1 C19 108.69(16) . . ?
N1 P1 C19 107.45(17) . . ?
O1 P1 C1 110.98(16) . . ?
N1 P1 C1 104.68(16) . . ?
C19 P1 C1 108.24(18) . . ?
O2 P2 C13 116.02(16) . . ?
O2 P2 C7 105.62(17) . . ?
C13 P2 C7 105.66(19) . . ?
O2 P2 C2 115.07(17) . . ?
C13 P2 C2 105.31(18) . . ?
C7 P2 C2 108.63(17) . . ?
P1 O1 Zn1 159.14(17) . . ?
P2 O2 Zn1 129.85(16) . . ?
C25 N1 C28 113.0(3) . . ?
C25 N1 P1 117.3(3) . . ?
C28 N1 P1 123.0(2) . . ?
C6 C1 C2 118.3(3) . . ?
C6 C1 P1 116.4(3) . . ?
C2 C1 P1 125.3(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 P2 115.8(3) . . ?
C1 C2 P2 125.2(3) . . ?
C4 C3 C2 121.8(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 122.0(4) . . ?
C5 C6 H6 119 . . ?
C1 C6 H6 119 . . ?
C8 C7 C12 119.6(4) . . ?
C8 C7 P2 118.2(3) . . ?
C12 C7 P2 121.9(3) . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.4(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 119.5(4) . . ?
C14 C13 P2 120.8(3) . . ?
C18 C13 P2 119.3(3) . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.1(4) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
C20 C19 C24 119.1(4) . . ?
C20 C19 P1 118.8(3) . . ?
C24 C19 P1 122.1(3) . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H20 120 . . ?
C19 C20 H20 120 . . ?
C20 C21 C22 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.6(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
N1 C25 C27 112.2(3) . . ?
N1 C25 C26 110.4(4) . . ?
C27 C25 C26 111.5(4) . . ?
N1 C25 H25 107.5 . . ?
C27 C25 H25 107.5 . . ?
C26 C25 H25 107.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 C30 113.9(3) . . ?
N1 C28 C29 113.2(3) . . ?
C30 C28 C29 112.9(3) . . ?
N1 C28 H28 105.3 . . ?
C30 C28 H28 105.3 . . ?
C29 C28 H28 105.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N1 P1 O1 Zn1 96.7(5) . . . . ?
C19 P1 O1 Zn1 -141.8(5) . . . . ?
C1 P1 O1 Zn1 -22.9(6) . . . . ?
C13 P2 O2 Zn1 49.3(3) . . . . ?
C7 P2 O2 Zn1 165.9(2) . . . . ?
C2 P2 O2 Zn1 -74.3(2) . . . . ?
O1 P1 N1 C25 -67.6(3) . . . . ?
C19 P1 N1 C25 170.3(3) . . . . ?
C1 P1 N1 C25 55.3(3) . . . . ?
O1 P1 N1 C28 81.7(3) . . . . ?
C19 P1 N1 C28 -40.4(3) . . . . ?
C1 P1 N1 C28 -155.3(3) . . . . ?
O1 P1 C1 C6 158.6(3) . . . . ?
N1 P1 C1 C6 32.2(4) . . . . ?
C19 P1 C1 C6 -82.2(3) . . . . ?
O1 P1 C1 C2 -23.4(4) . . . . ?
N1 P1 C1 C2 -149.8(3) . . . . ?
C19 P1 C1 C2 95.8(4) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
P1 C1 C2 C3 -179.4(3) . . . . ?
C6 C1 C2 P2 172.0(3) . . . . ?
P1 C1 C2 P2 -6.0(5) . . . . ?
O2 P2 C2 C3 -118.1(3) . . . . ?
C13 P2 C2 C3 112.9(3) . . . . ?
C7 P2 C2 C3 0.1(4) . . . . ?
O2 P2 C2 C1 68.4(4) . . . . ?
C13 P2 C2 C1 -60.7(4) . . . . ?
C7 P2 C2 C1 -173.5(3) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
P2 C2 C3 C4 -174.2(4) . . . . ?
C2 C3 C4 C5 2.0(7) . . . . ?
C3 C4 C5 C6 -2.1(7) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C2 C1 C6 C5 1.3(6) . . . . ?
P1 C1 C6 C5 179.5(3) . . . . ?
O2 P2 C7 C8 40.6(3) . . . . ?
C13 P2 C7 C8 164.0(3) . . . . ?
C2 P2 C7 C8 -83.4(3) . . . . ?
O2 P2 C7 C12 -132.4(3) . . . . ?
C13 P2 C7 C12 -8.9(4) . . . . ?
C2 P2 C7 C12 103.7(3) . . . . ?
C12 C7 C8 C9 -0.1(6) . . . . ?
P2 C7 C8 C9 -173.2(3) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C8 C9 C10 C11 -0.5(7) . . . . ?
C9 C10 C11 C12 -0.5(7) . . . . ?
C10 C11 C12 C7 1.2(6) . . . . ?
C8 C7 C12 C11 -0.9(6) . . . . ?
P2 C7 C12 C11 172.0(3) . . . . ?
O2 P2 C13 C14 -158.1(3) . . . . ?
C7 P2 C13 C14 85.3(3) . . . . ?
C2 P2 C13 C14 -29.6(4) . . . . ?
O2 P2 C13 C18 28.7(4) . . . . ?
C7 P2 C13 C18 -87.9(3) . . . . ?
C2 P2 C13 C18 157.2(3) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
P2 C13 C14 C15 -172.6(3) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C15 C16 C17 -1.1(7) . . . . ?
C15 C16 C17 C18 1.9(7) . . . . ?
C16 C17 C18 C13 -1.4(6) . . . . ?
C14 C13 C18 C17 0.2(6) . . . . ?
P2 C13 C18 C17 173.5(3) . . . . ?
O1 P1 C19 C20 -12.8(4) . . . . ?
N1 P1 C19 C20 114.0(3) . . . . ?
C1 P1 C19 C20 -133.4(3) . . . . ?
O1 P1 C19 C24 169.6(3) . . . . ?
N1 P1 C19 C24 -63.5(4) . . . . ?
C1 P1 C19 C24 49.0(4) . . . . ?
C24 C19 C20 C21 3.1(6) . . . . ?
P1 C19 C20 C21 -174.5(3) . . . . ?
C19 C20 C21 C22 -0.5(6) . . . . ?
C20 C21 C22 C23 -2.0(6) . . . . ?
C21 C22 C23 C24 1.9(6) . . . . ?
C22 C23 C24 C19 0.7(6) . . . . ?
C20 C19 C24 C23 -3.2(6) . . . . ?
P1 C19 C24 C23 174.3(3) . . . . ?
C28 N1 C25 C27 -56.0(4) . . . . ?
P1 N1 C25 C27 96.3(4) . . . . ?
C28 N1 C25 C26 69.0(4) . . . . ?
P1 N1 C25 C26 -138.7(3) . . . . ?
C25 N1 C28 C30 -125.6(4) . . . . ?
P1 N1 C28 C30 83.8(4) . . . . ?
C25 N1 C28 C29 103.7(4) . . . . ?
P1 N1 C28 C29 -46.9(4) . . . . ?

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
C18 H18 Cl1 0.93 2.8 3.541(5) 136.9 .
C24 H24 Cl1 0.93 2.67 3.524(4) 153.5 4_576
C27 H27A Cl2 0.96 2.91 3.761(5) 147.9 .
C29 H29B Cl2 0.96 2.95 3.685(4) 134.3 2_655
C30 H30C Cl2 0.96 2.98 3.702(5) 133.3 2_655
C6 H6 Cl1 0.93 2.98 3.526(4) 118.8 4_576
C18 H18 Cl1 0.93 2.8 3.541(5) 136.9 .
C24 H24 Cl1 0.93 2.67 3.524(4) 153.5 4_576
C27 H27A Cl2 0.96 2.91 3.761(5) 147.9 .
C29 H29B Cl2 0.96 2.95 3.685(4) 134.3 2_655
C30 H30C Cl2 0.96 2.98 3.702(5) 133.3 2_655

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 989180'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nbe156_s

_audit_creation_date             2014-01-08T23:58:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C30 H33 Cl2 N O P2 Se Zn'
_chemical_formula_weight         700.74

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.780(3)
_cell_length_b                   15.617(4)
_cell_length_c                   18.356(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.696(7)
_cell_angle_gamma                90
_cell_volume                     3083.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             1424
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    2.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS
;
_exptl_absorpt_correction_T_min  0.719867
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Smart 1000 CCD'
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_number            16631
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             5446
_reflns_number_gt                4201
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SUPERFLIP(Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury(Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+1.9635P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5446
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.101
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.101

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.34150(5) 0.63319(4) 0.71462(3) 0.01926(16) Uani 1 d . .
Cl1 Cl 0.19857(13) 0.63283(9) 0.62165(7) 0.0330(3) Uani 1 d . .
Cl2 Cl 0.52824(13) 0.66369(9) 0.67572(7) 0.0361(4) Uani 1 d . .
P1 P 0.28370(12) 0.74799(8) 0.86934(6) 0.0165(3) Uani 1 d . .
P2 P 0.21652(12) 0.52378(8) 0.86228(6) 0.0168(3) Uani 1 d . .
Se1 Se 0.35064(5) 0.49727(3) 0.78290(3) 0.02314(15) Uani 1 d . .
O1 O 0.2913(3) 0.7008(2) 0.79877(16) 0.0205(8) Uani 1 d . .
N1 N 0.3901(4) 0.8217(2) 0.8884(2) 0.0172(9) Uani 1 d . .
C1 C 0.3007(4) 0.6729(3) 0.9461(2) 0.0184(11) Uani 1 d . .
C2 C 0.2783(4) 0.5827(3) 0.9430(2) 0.0183(11) Uani 1 d . .
C3 C 0.2996(5) 0.5343(3) 1.0059(3) 0.0248(12) Uani 1 d . .
H3 H 0.2852 0.4756 1.0037 0.03 Uiso 1 calc . .
C4 C 0.3417(5) 0.5705(3) 1.0718(3) 0.0298(13) Uani 1 d . .
H4 H 0.3576 0.5362 1.1128 0.036 Uiso 1 calc . .
C5 C 0.3598(5) 0.6575(3) 1.0762(3) 0.0257(12) Uani 1 d . .
H5 H 0.3857 0.6828 1.1205 0.031 Uiso 1 calc . .
C6 C 0.3391(4) 0.7075(3) 1.0137(2) 0.0207(11) Uani 1 d . .
H6 H 0.3513 0.7664 1.0173 0.025 Uiso 1 calc . .
C7 C 0.1680(5) 0.4175(3) 0.8915(2) 0.0192(11) Uani 1 d . .
C8 C 0.2499(5) 0.3487(3) 0.8896(3) 0.0266(12) Uani 1 d . .
H8 H 0.3329 0.3582 0.8812 0.032 Uiso 1 calc . .
C9 C 0.2086(5) 0.2668(3) 0.9001(3) 0.0277(13) Uani 1 d . .
H9 H 0.2639 0.2212 0.8993 0.033 Uiso 1 calc . .
C10 C 0.0859(5) 0.2520(3) 0.9117(3) 0.0289(13) Uani 1 d . .
H10 H 0.058 0.1962 0.9172 0.035 Uiso 1 calc . .
C11 C 0.0041(5) 0.3188(3) 0.9154(3) 0.0287(13) Uani 1 d . .
H11 H -0.0784 0.3086 0.9247 0.034 Uiso 1 calc . .
C12 C 0.0449(5) 0.4014(3) 0.9051(3) 0.0259(12) Uani 1 d . .
H12 H -0.0106 0.4468 0.9073 0.031 Uiso 1 calc . .
C13 C 0.0724(5) 0.5742(3) 0.8330(2) 0.0203(11) Uani 1 d . .
C14 C -0.0003(5) 0.6110(3) 0.8855(3) 0.0227(12) Uani 1 d . .
H14 H 0.0321 0.6173 0.9334 0.027 Uiso 1 calc . .
C15 C -0.1198(5) 0.6378(3) 0.8661(3) 0.0277(13) Uani 1 d . .
H15 H -0.1672 0.6627 0.901 0.033 Uiso 1 calc . .
C16 C -0.1703(5) 0.6280(3) 0.7947(3) 0.0310(13) Uani 1 d . .
H16 H -0.2517 0.6445 0.7821 0.037 Uiso 1 calc . .
C17 C -0.0968(5) 0.5930(3) 0.7431(3) 0.0272(13) Uani 1 d . .
H17 H -0.1288 0.5881 0.695 0.033 Uiso 1 calc . .
C18 C 0.0224(5) 0.5654(3) 0.7615(2) 0.0199(11) Uani 1 d . .
H18 H 0.0695 0.541 0.7262 0.024 Uiso 1 calc . .
C19 C 0.1339(4) 0.7986(3) 0.8695(2) 0.0151(10) Uani 1 d . .
C20 C 0.0589(5) 0.8026(3) 0.8043(3) 0.0200(11) Uani 1 d . .
H20 H 0.0847 0.7768 0.7622 0.024 Uiso 1 calc . .
C21 C -0.0530(5) 0.8451(3) 0.8031(3) 0.0251(12) Uani 1 d . .
H21 H -0.1026 0.8475 0.7597 0.03 Uiso 1 calc . .
C22 C -0.0934(5) 0.8840(3) 0.8646(3) 0.0265(12) Uani 1 d . .
H22 H -0.1678 0.9143 0.8625 0.032 Uiso 1 calc . .
C23 C -0.0214(5) 0.8772(3) 0.9297(3) 0.0292(13) Uani 1 d . .
H23 H -0.0491 0.9017 0.9719 0.035 Uiso 1 calc . .
C24 C 0.0910(4) 0.8346(3) 0.9325(3) 0.0209(11) Uani 1 d . .
H24 H 0.1381 0.8299 0.9766 0.025 Uiso 1 calc . .
C25 C 0.5215(5) 0.7929(3) 0.9037(3) 0.0279(13) Uani 1 d . .
H25 H 0.5185 0.7334 0.9205 0.033 Uiso 1 calc . .
C26 C 0.5864(5) 0.8452(4) 0.9659(3) 0.0442(16) Uani 1 d . .
H26A H 0.5377 0.8433 1.0079 0.066 Uiso 1 calc . .
H26B H 0.5947 0.9036 0.9505 0.066 Uiso 1 calc . .
H26C H 0.6672 0.8216 0.9783 0.066 Uiso 1 calc . .
C27 C 0.5964(5) 0.7939(4) 0.8374(3) 0.0380(15) Uani 1 d . .
H27A H 0.5549 0.7603 0.7994 0.057 Uiso 1 calc . .
H27B H 0.6773 0.7704 0.8496 0.057 Uiso 1 calc . .
H27C H 0.6047 0.8518 0.8208 0.057 Uiso 1 calc . .
C28 C 0.3798(5) 0.9122(3) 0.8604(3) 0.0229(12) Uani 1 d . .
H28 H 0.4651 0.9343 0.8635 0.027 Uiso 1 calc . .
C29 C 0.3358(5) 0.9191(3) 0.7796(3) 0.0317(13) Uani 1 d . .
H29A H 0.3841 0.8813 0.7514 0.047 Uiso 1 calc . .
H29B H 0.346 0.9769 0.7632 0.047 Uiso 1 calc . .
H29C H 0.2497 0.9034 0.7734 0.047 Uiso 1 calc . .
C30 C 0.3086(6) 0.9712(3) 0.9082(3) 0.0435(16) Uani 1 d . .
H30A H 0.3401 0.9655 0.9581 0.065 Uiso 1 calc . .
H30B H 0.222 0.9562 0.9042 0.065 Uiso 1 calc . .
H30C H 0.3184 1.0294 0.8927 0.065 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 1.976(3) . ?
Zn1 Cl1 2.2242(14) . ?
Zn1 Cl2 2.2304(15) . ?
Zn1 Se1 2.4639(9) . ?
P1 O1 1.497(3) . ?
P1 N1 1.646(4) . ?
P1 C19 1.798(5) . ?
P1 C1 1.833(5) . ?
P2 C13 1.793(5) . ?
P2 C7 1.831(5) . ?
P2 C2 1.833(5) . ?
P2 Se1 2.1580(14) . ?
N1 C25 1.495(6) . ?
N1 C28 1.507(6) . ?
C1 C6 1.392(6) . ?
C1 C2 1.429(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.386(7) . ?
C3 H3 0.93 . ?
C4 C5 1.375(7) . ?
C4 H4 0.93 . ?
C5 C6 1.394(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C12 1.389(7) . ?
C7 C8 1.393(7) . ?
C8 C9 1.371(7) . ?
C8 H8 0.93 . ?
C9 C10 1.373(7) . ?
C9 H9 0.93 . ?
C10 C11 1.371(7) . ?
C10 H10 0.93 . ?
C11 C12 1.380(7) . ?
C11 H11 0.93 . ?
C12 H12 0.93 . ?
C13 C18 1.393(6) . ?
C13 C14 1.404(6) . ?
C14 C15 1.379(7) . ?
C14 H14 0.93 . ?
C15 C16 1.395(7) . ?
C15 H15 0.93 . ?
C16 C17 1.386(7) . ?
C16 H16 0.93 . ?
C17 C18 1.377(7) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C24 1.392(6) . ?
C19 C20 1.402(6) . ?
C20 C21 1.376(7) . ?
C20 H20 0.93 . ?
C21 C22 1.377(7) . ?
C21 H21 0.93 . ?
C22 C23 1.387(7) . ?
C22 H22 0.93 . ?
C23 C24 1.381(7) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C27 1.504(7) . ?
C25 C26 1.535(7) . ?
C25 H25 0.98 . ?
C26 H26A 0.96 . ?
C26 H26B 0.96 . ?
C26 H26C 0.96 . ?
C27 H27A 0.96 . ?
C27 H27B 0.96 . ?
C27 H27C 0.96 . ?
C28 C30 1.515(7) . ?
C28 C29 1.533(6) . ?
C28 H28 0.98 . ?
C29 H29A 0.96 . ?
C29 H29B 0.96 . ?
C29 H29C 0.96 . ?
C30 H30A 0.96 . ?
C30 H30B 0.96 . ?
C30 H30C 0.96 . ?

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 Cl1 112.95(10) . . ?
O1 Zn1 Cl2 115.76(11) . . ?
Cl1 Zn1 Cl2 110.47(6) . . ?
O1 Zn1 Se1 93.84(9) . . ?
Cl1 Zn1 Se1 113.02(4) . . ?
Cl2 Zn1 Se1 109.85(4) . . ?
O1 P1 N1 116.8(2) . . ?
O1 P1 C19 108.5(2) . . ?
N1 P1 C19 107.8(2) . . ?
O1 P1 C1 110.0(2) . . ?
N1 P1 C1 104.5(2) . . ?
C19 P1 C1 109.0(2) . . ?
C13 P2 C7 103.2(2) . . ?
C13 P2 C2 106.5(2) . . ?
C7 P2 C2 108.3(2) . . ?
C13 P2 Se1 119.12(16) . . ?
C7 P2 Se1 103.92(16) . . ?
C2 P2 Se1 114.69(16) . . ?
P2 Se1 Zn1 99.88(4) . . ?
P1 O1 Zn1 166.6(2) . . ?
C25 N1 C28 113.3(4) . . ?
C25 N1 P1 117.9(3) . . ?
C28 N1 P1 123.3(3) . . ?
C6 C1 C2 117.3(4) . . ?
C6 C1 P1 116.5(4) . . ?
C2 C1 P1 126.3(3) . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 P2 115.5(4) . . ?
C1 C2 P2 125.4(3) . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.4(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 122.6(5) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C12 C7 C8 118.6(5) . . ?
C12 C7 P2 120.7(4) . . ?
C8 C7 P2 119.9(4) . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.5(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 120.7(5) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 119.2(5) . . ?
C18 C13 P2 121.0(4) . . ?
C14 C13 P2 119.0(4) . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C14 C15 C16 120.7(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.8(5) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 119.9(5) . . ?
C17 C18 H18 120 . . ?
C13 C18 H18 120 . . ?
C24 C19 C20 119.2(4) . . ?
C24 C19 P1 121.7(4) . . ?
C20 C19 P1 119.1(4) . . ?
C21 C20 C19 119.5(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 121.5(5) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 119.0(5) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C19 120.1(5) . . ?
C23 C24 H24 120 . . ?
C19 C24 H24 120 . . ?
N1 C25 C27 113.3(4) . . ?
N1 C25 C26 111.1(4) . . ?
C27 C25 C26 110.7(4) . . ?
N1 C25 H25 107.1 . . ?
C27 C25 H25 107.1 . . ?
C26 C25 H25 107.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 C30 113.7(4) . . ?
N1 C28 C29 114.0(4) . . ?
C30 C28 C29 112.4(5) . . ?
N1 C28 H28 105.2 . . ?
C30 C28 H28 105.2 . . ?
C29 C28 H28 105.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N1 P1 O1 Zn1 54.0(10) . . . . ?
C19 P1 O1 Zn1 176.1(9) . . . . ?
C1 P1 O1 Zn1 -64.8(10) . . . . ?
O1 P1 N1 C25 -67.6(4) . . . . ?
C19 P1 N1 C25 170.0(3) . . . . ?
C1 P1 N1 C25 54.1(4) . . . . ?
O1 P1 N1 C28 84.3(4) . . . . ?
C19 P1 N1 C28 -38.1(4) . . . . ?
C1 P1 N1 C28 -153.9(3) . . . . ?
O1 P1 C1 C6 158.1(4) . . . . ?
N1 P1 C1 C6 32.0(4) . . . . ?
C19 P1 C1 C6 -83.1(4) . . . . ?
O1 P1 C1 C2 -21.9(5) . . . . ?
N1 P1 C1 C2 -148.1(4) . . . . ?
C19 P1 C1 C2 96.9(4) . . . . ?
C6 C1 C2 C3 -2.2(7) . . . . ?
P1 C1 C2 C3 177.9(4) . . . . ?
C6 C1 C2 P2 175.2(4) . . . . ?
P1 C1 C2 P2 -4.7(6) . . . . ?
C13 P2 C2 C3 122.2(4) . . . . ?
C7 P2 C2 C3 11.7(4) . . . . ?
Se1 P2 C2 C3 -103.8(4) . . . . ?
C13 P2 C2 C1 -55.3(5) . . . . ?
C7 P2 C2 C1 -165.7(4) . . . . ?
Se1 P2 C2 C1 78.7(4) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
P2 C2 C3 C4 -177.5(4) . . . . ?
C2 C3 C4 C5 1.9(8) . . . . ?
C3 C4 C5 C6 -1.9(8) . . . . ?
C2 C1 C6 C5 2.2(7) . . . . ?
P1 C1 C6 C5 -177.8(4) . . . . ?
C4 C5 C6 C1 -0.2(8) . . . . ?
C13 P2 C7 C12 -16.5(4) . . . . ?
C2 P2 C7 C12 96.1(4) . . . . ?
Se1 P2 C7 C12 -141.5(4) . . . . ?
C13 P2 C7 C8 153.6(4) . . . . ?
C2 P2 C7 C8 -93.7(4) . . . . ?
Se1 P2 C7 C8 28.6(4) . . . . ?
C12 C7 C8 C9 0.8(7) . . . . ?
P2 C7 C8 C9 -169.6(4) . . . . ?
C7 C8 C9 C10 0.8(8) . . . . ?
C8 C9 C10 C11 -2.1(8) . . . . ?
C9 C10 C11 C12 1.9(8) . . . . ?
C10 C11 C12 C7 -0.3(8) . . . . ?
C8 C7 C12 C11 -1.0(7) . . . . ?
P2 C7 C12 C11 169.3(4) . . . . ?
C7 P2 C13 C18 -87.9(4) . . . . ?
C2 P2 C13 C18 158.2(4) . . . . ?
Se1 P2 C13 C18 26.5(4) . . . . ?
C7 P2 C13 C14 81.6(4) . . . . ?
C2 P2 C13 C14 -32.3(4) . . . . ?
Se1 P2 C13 C14 -164.0(3) . . . . ?
C18 C13 C14 C15 0.1(7) . . . . ?
P2 C13 C14 C15 -169.6(4) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C14 C15 C16 C17 -1.9(8) . . . . ?
C15 C16 C17 C18 2.2(8) . . . . ?
C16 C17 C18 C13 -1.5(7) . . . . ?
C14 C13 C18 C17 0.3(7) . . . . ?
P2 C13 C18 C17 169.7(4) . . . . ?
O1 P1 C19 C24 168.6(4) . . . . ?
N1 P1 C19 C24 -64.0(4) . . . . ?
C1 P1 C19 C24 48.9(4) . . . . ?
O1 P1 C19 C20 -12.0(4) . . . . ?
N1 P1 C19 C20 115.4(4) . . . . ?
C1 P1 C19 C20 -131.8(4) . . . . ?
C24 C19 C20 C21 2.7(7) . . . . ?
P1 C19 C20 C21 -176.7(3) . . . . ?
C19 C20 C21 C22 0.1(7) . . . . ?
C20 C21 C22 C23 -2.5(7) . . . . ?
C21 C22 C23 C24 2.1(8) . . . . ?
C22 C23 C24 C19 0.7(8) . . . . ?
C20 C19 C24 C23 -3.1(7) . . . . ?
P1 C19 C24 C23 176.3(4) . . . . ?
C28 N1 C25 C27 -60.9(5) . . . . ?
P1 N1 C25 C27 93.8(4) . . . . ?
C28 N1 C25 C26 64.5(5) . . . . ?
P1 N1 C25 C26 -140.8(4) . . . . ?
C25 N1 C28 C30 -120.3(5) . . . . ?
P1 N1 C28 C30 86.6(5) . . . . ?
C25 N1 C28 C29 109.0(5) . . . . ?
P1 N1 C28 C29 -44.1(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
C18 H18 Cl1 0.93 2.83 3.454(5) 125.3 .
C24 H24 Cl1 0.93 2.76 3.624(5) 154.7 4_576
C27 H27A Cl2 0.96 2.73 3.633(6) 158 .
C27 H27C Se1 0.96 3.02 3.930(6) 158.4 2_656
C18 H18 Cl1 0.93 2.83 3.454(5) 125.3 .
C24 H24 Cl1 0.93 2.76 3.624(5) 154.7 4_576
C27 H27A Cl2 0.96 2.73 3.633(6) 158 .
C27 H27C Se1 0.96 3.02 3.930(6) 158.4 2_656

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 989181'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_n157

_audit_creation_date             2013-12-10T22:44:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H33 Cl2 N1 O1 P2 S1 Zn1'
_chemical_formula_sum            'C30 H33 Cl2 N1 O1 P2 S1 Zn1'
_chemical_formula_weight         653.84
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7119(3)
_cell_length_b                   15.7322(7)
_cell_length_c                   18.1799(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.429(3)
_cell_angle_gamma                90
_cell_volume                     3058.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5926
_cell_measurement_theta_min      1.9012
_cell_measurement_theta_max      28.7578
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0791
-1 -1 0 0.0791
-3 1 0 0.0662
3 -1 0 0.0662
0 0 -1 0.206
0 0 1 0.206

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.85938
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.638
_shelx_estimated_absorpt_T_max   0.862

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4186
_diffrn_orient_matrix_ub_11      -0.0621635
_diffrn_orient_matrix_ub_12      -0.0146944
_diffrn_orient_matrix_ub_13      -0.007105
_diffrn_orient_matrix_ub_21      0.0231878
_diffrn_orient_matrix_ub_22      -0.0396859
_diffrn_orient_matrix_ub_23      -0.0117281
_diffrn_orient_matrix_ub_31      -0.0003919
_diffrn_orient_matrix_ub_32      -0.0155852
_diffrn_orient_matrix_ub_33      0.0366071
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_number            12335
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             5572
_reflns_number_gt                4748
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SUPERFLIP(Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury(Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.9423P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5572
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.081
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.13

#----------------------------------------------------------------------------#
#                   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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'

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
Zn1 Zn 0.33748(3) 0.63187(2) 0.21352(2) 0.01766(10) Uani 1 d . .
Cl2 Cl 0.52694(6) 0.65421(5) 0.17386(4) 0.03131(18) Uani 1 d . .
Cl1 Cl 0.19352(7) 0.63343(5) 0.12056(3) 0.03289(18) Uani 1 d . .
S1 S 0.33743(6) 0.50504(4) 0.28305(3) 0.02159(16) Uani 1 d . .
P1 P 0.28477(6) 0.75037(4) 0.36753(3) 0.01452(15) Uani 1 d . .
P2 P 0.21666(6) 0.52785(4) 0.36035(3) 0.01532(15) Uani 1 d . .
O1 O 0.29223(15) 0.70444(11) 0.29593(8) 0.0200(4) Uani 1 d . .
N1 N 0.39081(18) 0.82372(13) 0.38637(10) 0.0177(4) Uani 1 d . .
C1 C 0.3025(2) 0.67534(16) 0.44462(12) 0.0157(5) Uani 1 d . .
C2 C 0.2800(2) 0.58625(16) 0.44112(12) 0.0169(5) Uani 1 d . .
C3 C 0.3024(3) 0.53765(18) 0.50428(13) 0.0261(6) Uani 1 d . .
H3 H 0.2881 0.4781 0.5019 0.031 Uiso 1 calc . .
C4 C 0.3453(3) 0.57375(19) 0.57086(13) 0.0303(7) Uani 1 d . .
H4 H 0.3618 0.5389 0.613 0.036 Uiso 1 calc . .
C5 C 0.3637(3) 0.66004(18) 0.57539(13) 0.0254(6) Uani 1 d . .
H5 H 0.391 0.6854 0.621 0.03 Uiso 1 calc . .
C6 C 0.3421(2) 0.71015(17) 0.51283(12) 0.0192(5) Uani 1 d . .
H6 H 0.3546 0.7698 0.5166 0.023 Uiso 1 calc . .
C7 C 0.1698(2) 0.42242(16) 0.38958(12) 0.0189(5) Uani 1 d . .
C8 C 0.2538(2) 0.35501(17) 0.38750(14) 0.0231(6) Uani 1 d . .
H8 H 0.3389 0.3659 0.3786 0.028 Uiso 1 calc . .
C9 C 0.2149(3) 0.27239(18) 0.39820(14) 0.0278(6) Uani 1 d . .
H9 H 0.2728 0.2268 0.3966 0.033 Uiso 1 calc . .
C10 C 0.0909(3) 0.25648(18) 0.41129(14) 0.0288(6) Uani 1 d . .
H10 H 0.0634 0.1997 0.4178 0.035 Uiso 1 calc . .
C11 C 0.0078(3) 0.32247(18) 0.41491(14) 0.0285(6) Uani 1 d . .
H11 H -0.0767 0.3112 0.4248 0.034 Uiso 1 calc . .
C12 C 0.0459(2) 0.40522(18) 0.40427(13) 0.0231(6) Uani 1 d . .
H12 H -0.0123 0.4505 0.4069 0.028 Uiso 1 calc . .
C13 C 0.0699(2) 0.57758(16) 0.33294(12) 0.0173(5) Uani 1 d . .
C14 C -0.0007(2) 0.61454(16) 0.38638(14) 0.0213(6) Uani 1 d . .
H14 H 0.0346 0.6224 0.4351 0.026 Uiso 1 calc . .
C15 C -0.1218(3) 0.63963(17) 0.36839(16) 0.0279(6) Uani 1 d . .
H15 H -0.1705 0.664 0.4049 0.034 Uiso 1 calc . .
C16 C -0.1726(3) 0.62945(18) 0.29728(17) 0.0314(7) Uani 1 d . .
H16 H -0.2562 0.6468 0.2851 0.038 Uiso 1 calc . .
C17 C -0.1025(3) 0.59428(19) 0.24382(15) 0.0288(6) Uani 1 d . .
H17 H -0.1377 0.5883 0.1949 0.035 Uiso 1 calc . .
C18 C 0.0189(2) 0.56769(17) 0.26103(13) 0.0214(6) Uani 1 d . .
H18 H 0.0669 0.543 0.2243 0.026 Uiso 1 calc . .
C19 C 0.1335(2) 0.79931(16) 0.36905(12) 0.0165(5) Uani 1 d . .
C20 C 0.0596(2) 0.80476(17) 0.30309(13) 0.0206(6) Uani 1 d . .
H20 H 0.0869 0.7791 0.2596 0.025 Uiso 1 calc . .
C21 C -0.0526(2) 0.84730(18) 0.30149(14) 0.0260(6) Uani 1 d . .
H21 H -0.1025 0.8512 0.2566 0.031 Uiso 1 calc . .
C22 C -0.0935(2) 0.88451(18) 0.36460(15) 0.0268(6) Uani 1 d . .
H22 H -0.1699 0.9154 0.3627 0.032 Uiso 1 calc . .
C23 C -0.0232(3) 0.87666(18) 0.43060(15) 0.0262(6) Uani 1 d . .
H23 H -0.0524 0.901 0.4742 0.031 Uiso 1 calc . .
C24 C 0.0895(2) 0.83354(17) 0.43332(13) 0.0208(6) Uani 1 d . .
H24 H 0.1368 0.8273 0.4789 0.025 Uiso 1 calc . .
C25 C 0.5238(2) 0.79404(19) 0.39795(14) 0.0261(6) Uani 1 d . .
H25 H 0.5213 0.7327 0.4124 0.031 Uiso 1 calc . .
C26 C 0.5922(3) 0.8419(2) 0.46147(16) 0.0448(9) Uani 1 d . .
H26A H 0.5446 0.8373 0.5057 0.067 Uiso 1 calc . .
H26B H 0.6005 0.9019 0.4481 0.067 Uiso 1 calc . .
H26C H 0.6755 0.8172 0.4714 0.067 Uiso 1 calc . .
C27 C 0.5950(3) 0.7996(2) 0.32794(16) 0.0327(7) Uani 1 d . .
H27A H 0.5492 0.7685 0.2882 0.049 Uiso 1 calc . .
H27B H 0.6783 0.7746 0.3369 0.049 Uiso 1 calc . .
H27C H 0.6033 0.8593 0.3137 0.049 Uiso 1 calc . .
C28 C 0.3794(2) 0.91454(16) 0.36098(13) 0.0218(6) Uani 1 d . .
H28 H 0.4667 0.9374 0.3645 0.026 Uiso 1 calc . .
C29 C 0.3345(3) 0.92466(19) 0.28040(14) 0.0312(7) Uani 1 d . .
H29A H 0.3837 0.8876 0.2499 0.047 Uiso 1 calc . .
H29B H 0.345 0.9839 0.2653 0.047 Uiso 1 calc . .
H29C H 0.246 0.909 0.2741 0.047 Uiso 1 calc . .
C30 C 0.3067(3) 0.97055(19) 0.41171(17) 0.0411(8) Uani 1 d . .
H30A H 0.3386 0.962 0.4628 0.062 Uiso 1 calc . .
H30B H 0.2179 0.9553 0.4069 0.062 Uiso 1 calc . .
H30C H 0.3169 1.0303 0.3981 0.062 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 1.9672(16) . ?
Zn1 Cl1 2.2187(7) . ?
Zn1 Cl2 2.2220(7) . ?
Zn1 S1 2.3620(7) . ?
S1 P2 1.9987(8) . ?
P1 O1 1.4950(17) . ?
P1 N1 1.641(2) . ?
P1 C19 1.796(2) . ?
P1 C1 1.833(2) . ?
P2 C13 1.800(2) . ?
P2 C7 1.821(3) . ?
P2 C2 1.828(2) . ?
N1 C25 1.502(3) . ?
N1 C28 1.504(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.423(4) . ?
C2 C3 1.388(3) . ?
C3 C4 1.390(4) . ?
C3 H3 0.95 . ?
C4 C5 1.374(4) . ?
C4 H4 0.95 . ?
C5 C6 1.392(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.393(4) . ?
C7 C12 1.396(3) . ?
C8 C9 1.382(4) . ?
C8 H8 0.95 . ?
C9 C10 1.386(4) . ?
C9 H9 0.95 . ?
C10 C11 1.372(4) . ?
C10 H10 0.95 . ?
C11 C12 1.382(4) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.394(3) . ?
C13 C18 1.395(3) . ?
C14 C15 1.376(4) . ?
C14 H14 0.95 . ?
C15 C16 1.382(4) . ?
C15 H15 0.95 . ?
C16 C17 1.379(4) . ?
C16 H16 0.95 . ?
C17 C18 1.384(4) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C19 C24 1.394(3) . ?
C19 C20 1.399(3) . ?
C20 C21 1.374(4) . ?
C20 H20 0.95 . ?
C21 C22 1.383(4) . ?
C21 H21 0.95 . ?
C22 C23 1.384(4) . ?
C22 H22 0.95 . ?
C23 C24 1.382(4) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C25 C27 1.525(4) . ?
C25 C26 1.529(4) . ?
C25 H25 1 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 C29 1.523(3) . ?
C28 C30 1.523(4) . ?
C28 H28 1 . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 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 Cl1 112.46(5) . . ?
O1 Zn1 Cl2 115.27(5) . . ?
Cl1 Zn1 Cl2 110.96(3) . . ?
O1 Zn1 S1 94.29(5) . . ?
Cl1 Zn1 S1 113.24(3) . . ?
Cl2 Zn1 S1 109.67(3) . . ?
P2 S1 Zn1 104.21(3) . . ?
O1 P1 N1 116.69(10) . . ?
O1 P1 C19 108.41(10) . . ?
N1 P1 C19 108.02(11) . . ?
O1 P1 C1 110.23(11) . . ?
N1 P1 C1 104.73(10) . . ?
C19 P1 C1 108.47(11) . . ?
C13 P2 C7 103.02(11) . . ?
C13 P2 C2 106.27(11) . . ?
C7 P2 C2 108.59(11) . . ?
C13 P2 S1 118.35(8) . . ?
C7 P2 S1 104.05(8) . . ?
C2 P2 S1 115.48(8) . . ?
P1 O1 Zn1 166.41(11) . . ?
C25 N1 C28 113.40(19) . . ?
C25 N1 P1 116.71(17) . . ?
C28 N1 P1 124.17(16) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 P1 115.97(19) . . ?
C2 C1 P1 126.18(17) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 P2 115.2(2) . . ?
C1 C2 P2 125.78(17) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 122.0(2) . . ?
C5 C6 H6 119 . . ?
C1 C6 H6 119 . . ?
C8 C7 C12 118.8(2) . . ?
C8 C7 P2 119.71(19) . . ?
C12 C7 P2 120.9(2) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 120.1(2) . . ?
C14 C13 P2 119.34(18) . . ?
C18 C13 P2 119.84(19) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C24 C19 C20 119.5(2) . . ?
C24 C19 P1 121.95(18) . . ?
C20 C19 P1 118.54(18) . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 119.9(2) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
N1 C25 C27 112.5(2) . . ?
N1 C25 C26 111.1(2) . . ?
C27 C25 C26 111.2(2) . . ?
N1 C25 H25 107.2 . . ?
C27 C25 H25 107.2 . . ?
C26 C25 H25 107.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 C29 114.2(2) . . ?
N1 C28 C30 113.5(2) . . ?
C29 C28 C30 112.2(2) . . ?
N1 C28 H28 105.3 . . ?
C29 C28 H28 105.3 . . ?
C30 C28 H28 105.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N1 P1 O1 Zn1 70.9(5) . . . . ?
C19 P1 O1 Zn1 -166.9(5) . . . . ?
C1 P1 O1 Zn1 -48.3(5) . . . . ?
O1 P1 N1 C25 -65.60(19) . . . . ?
C19 P1 N1 C25 172.04(16) . . . . ?
C1 P1 N1 C25 56.58(18) . . . . ?
O1 P1 N1 C28 85.9(2) . . . . ?
C19 P1 N1 C28 -36.5(2) . . . . ?
C1 P1 N1 C28 -151.92(18) . . . . ?
O1 P1 C1 C6 157.81(18) . . . . ?
N1 P1 C1 C6 31.5(2) . . . . ?
C19 P1 C1 C6 -83.6(2) . . . . ?
O1 P1 C1 C2 -22.2(2) . . . . ?
N1 P1 C1 C2 -148.5(2) . . . . ?
C19 P1 C1 C2 96.4(2) . . . . ?
C6 C1 C2 C3 -2.3(3) . . . . ?
P1 C1 C2 C3 177.63(19) . . . . ?
C6 C1 C2 P2 174.99(18) . . . . ?
P1 C1 C2 P2 -5.0(3) . . . . ?
C13 P2 C2 C3 121.5(2) . . . . ?
C7 P2 C2 C3 11.3(2) . . . . ?
S1 P2 C2 C3 -105.07(19) . . . . ?
C13 P2 C2 C1 -55.9(2) . . . . ?
C7 P2 C2 C1 -166.1(2) . . . . ?
S1 P2 C2 C1 77.5(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
P2 C2 C3 C4 -177.1(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
P1 C1 C6 C5 -177.7(2) . . . . ?
C13 P2 C7 C8 155.0(2) . . . . ?
C2 P2 C7 C8 -92.6(2) . . . . ?
S1 P2 C7 C8 30.9(2) . . . . ?
C13 P2 C7 C12 -15.9(2) . . . . ?
C2 P2 C7 C12 96.5(2) . . . . ?
S1 P2 C7 C12 -140.03(18) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
P2 C7 C8 C9 -169.8(2) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
P2 C7 C12 C11 169.7(2) . . . . ?
C7 P2 C13 C14 82.9(2) . . . . ?
C2 P2 C13 C14 -31.2(2) . . . . ?
S1 P2 C13 C14 -162.98(17) . . . . ?
C7 P2 C13 C18 -87.3(2) . . . . ?
C2 P2 C13 C18 158.6(2) . . . . ?
S1 P2 C13 C18 26.8(2) . . . . ?
C18 C13 C14 C15 1.4(4) . . . . ?
P2 C13 C14 C15 -168.9(2) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C14 C13 C18 C17 -0.6(4) . . . . ?
P2 C13 C18 C17 169.6(2) . . . . ?
O1 P1 C19 C24 168.1(2) . . . . ?
N1 P1 C19 C24 -64.6(2) . . . . ?
C1 P1 C19 C24 48.4(2) . . . . ?
O1 P1 C19 C20 -13.5(2) . . . . ?
N1 P1 C19 C20 113.8(2) . . . . ?
C1 P1 C19 C20 -133.2(2) . . . . ?
C24 C19 C20 C21 3.2(4) . . . . ?
P1 C19 C20 C21 -175.3(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 -2.1(4) . . . . ?
C21 C22 C23 C24 1.6(4) . . . . ?
C22 C23 C24 C19 1.3(4) . . . . ?
C20 C19 C24 C23 -3.7(4) . . . . ?
P1 C19 C24 C23 174.8(2) . . . . ?
C28 N1 C25 C27 -59.7(3) . . . . ?
P1 N1 C25 C27 94.8(2) . . . . ?
C28 N1 C25 C26 65.6(3) . . . . ?
P1 N1 C25 C26 -139.8(2) . . . . ?
C25 N1 C28 C29 107.2(2) . . . . ?
P1 N1 C28 C29 -45.2(3) . . . . ?
C25 N1 C28 C30 -122.5(2) . . . . ?
P1 N1 C28 C30 85.2(3) . . . . ?

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
C18 H18 Cl1 0.95 2.78 3.415(3) 125 .
C24 H24 Cl1 0.95 2.68 3.556(2) 153.1 4_576
C27 H27A Cl2 0.98 2.75 3.656(3) 154.4 .
C27 H27C S1 0.98 2.98 3.900(3) 156.8 2_655
C30 H30C Cl2 0.98 2.93 3.778(3) 145.8 2_655
C18 H18 Cl1 0.95 2.78 3.415(3) 125 .
C24 H24 Cl1 0.95 2.68 3.556(2) 153.1 4_576
C27 H27A Cl2 0.98 2.75 3.656(3) 154.4 .
C27 H27C S1 0.98 2.98 3.900(3) 156.8 2_655
C30 H30C Cl2 0.98 2.93 3.778(3) 145.8 2_655

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 989182'
