# 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_I
_chemical_name_systematic        ?
_chemical_name_common            MM67
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 I2 N P Pt'
_chemical_formula_iupac          ?
_chemical_formula_weight         770.27

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5189(7)
_cell_length_b                   10.9327(10)
_cell_length_c                   11.5197(10)
_cell_angle_alpha                84.048(4)
_cell_angle_beta                 81.976(4)
_cell_angle_gamma                86.335(4)
_cell_volume                     1179.20(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9235
_cell_measurement_theta_min      2.4677
_cell_measurement_theta_max      27.8259
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'light orange'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712

_exptl_absorpt_coefficient_mu    8.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_T_max  0.48


_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            51025
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

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

_reflns_number_total             5847
_reflns_number_gt                4953
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1129
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_number_reflns         5847
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0827P)²+0.3094P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.103
_refine_diff_density_min         -1.964
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'SHELXTL-97 (Sheldrick, 2008)'
_audit_creation_method           'SHELXTL-97 (Sheldrick, 2008)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pt Pt1 0.473091(18) 0.700733(16) 0.786607(16) 0.04039(9) Uani d . 1 . .
I I1 0.29665(5) 0.66118(5) 0.98164(3) 0.06425(13) Uani d . 1 . .
I I2 0.66762(4) 0.71489(5) 0.60498(4) 0.06161(13) Uani d . 1 . .
N N1 0.6417(5) 0.6676(5) 0.8900(5) 0.0619(13) Uani d . 1 . .
H H1A 0.6034 0.6402 0.9632 0.074 Uiso calc R 1 . .
H H1B 0.6976 0.6052 0.8611 0.074 Uiso calc R 1 . .
C C1 0.7359(7) 0.7681(7) 0.9014(6) 0.0703(18) Uani d . 1 . .
H H1 0.7778 0.7968 0.8214 0.084 Uiso calc R 1 . .
C C2 0.8584(8) 0.7146(8) 0.9667(7) 0.088(2) Uani d . 1 . .
H H2A 0.8221 0.6873 1.0465 0.133 Uiso calc R 1 . .
H H2B 0.9253 0.7767 0.9663 0.133 Uiso calc R 1 . .
H H2C 0.9047 0.6462 0.9283 0.133 Uiso calc R 1 . .
C C3 0.6561(8) 0.8752(8) 0.9517(8) 0.087(2) Uani d . 1 . .
H H3A 0.5797 0.9014 0.9073 0.13 Uiso calc R 1 . .
H H3B 0.7187 0.9413 0.9484 0.13 Uiso calc R 1 . .
H H3C 0.6184 0.8523 1.0322 0.13 Uiso calc R 1 . .
P P1 0.29311(13) 0.72668(11) 0.67827(11) 0.0353(2) Uani d . 1 . .
C C4 0.1662(5) 0.8536(4) 0.7104(4) 0.0392(10) Uani d . 1 . .
C C5 0.1757(6) 0.9251(5) 0.8018(5) 0.0542(13) Uani d . 1 . .
H H5 0.2494 0.9094 0.8472 0.065 Uiso calc R 1 . .
C C6 0.0743(8) 1.0206(6) 0.8253(7) 0.0732(19) Uani d . 1 . .
H H6 0.0824 1.0687 0.8858 0.088 Uiso calc R 1 . .
C C7 -0.0369(7) 1.0447(6) 0.7609(7) 0.0669(18) Uani d . 1 . .
H H7 -0.106 1.1062 0.7797 0.08 Uiso calc R 1 . .
C C8 -0.0452(6) 0.9764(6) 0.6675(6) 0.0645(16) Uani d . 1 . .
H H8 -0.1188 0.9933 0.6221 0.077 Uiso calc R 1 . .
C C9 0.0560(6) 0.8831(5) 0.6417(5) 0.0507(12) Uani d . 1 . .
H H9 0.0507 0.8391 0.5777 0.061 Uiso calc R 1 . .
C C10 0.3368(5) 0.7593(4) 0.5188(4) 0.0375(10) Uani d . 1 . .
C C11 0.3741(6) 0.8790(5) 0.4736(5) 0.0486(12) Uani d . 1 . .
H H11 0.3748 0.9397 0.5244 0.058 Uiso calc R 1 . .
C C12 0.4097(6) 0.9066(6) 0.3539(5) 0.0598(15) Uani d . 1 . .
H H12 0.437 0.9852 0.3241 0.072 Uiso calc R 1 . .
C C13 0.4045(6) 0.8165(7) 0.2778(5) 0.0617(16) Uani d . 1 . .
H H13 0.4258 0.8358 0.197 0.074 Uiso calc R 1 . .
C C14 0.3686(7) 0.7003(6) 0.3209(5) 0.0612(15) Uani d . 1 . .
H H14 0.3679 0.6404 0.2694 0.073 Uiso calc R 1 . .
C C15 0.3328(6) 0.6705(5) 0.4414(5) 0.0509(12) Uani d . 1 . .
H H15 0.3064 0.5914 0.4701 0.061 Uiso calc R 1 . .
C C16 0.1976(5) 0.5853(4) 0.6920(4) 0.0411(10) Uani d . 1 . .
C C17 0.0540(7) 0.5834(6) 0.6868(7) 0.0659(17) Uani d . 1 . .
H H17 -0.0023 0.6562 0.6857 0.079 Uiso calc R 1 . .
C C18 -0.0059(9) 0.4704(7) 0.6833(8) 0.093(3) Uani d . 1 . .
H H18 -0.102 0.4692 0.6763 0.112 Uiso calc R 1 . .
C C19 0.0725(10) 0.3629(6) 0.6899(7) 0.082(2) Uani d . 1 . .
H H19 0.0299 0.2886 0.6899 0.098 Uiso calc R 1 . .
C C20 0.2140(8) 0.3639(5) 0.6965(6) 0.0659(17) Uani d . 1 . .
H H20 0.2686 0.2903 0.6999 0.079 Uiso calc R 1 . .
C C21 0.2772(7) 0.4752(5) 0.6981(5) 0.0539(13) Uani d . 1 . .
H H21 0.3739 0.4753 0.7033 0.065 Uiso calc R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pt1 N1 . 2.120(4) ?
Pt1 P1 . 2.2438(12) ?
Pt1 I2 . 2.5920(5) ?
Pt1 I1 . 2.6255(5) ?
N1 C1 . 1.489(8) ?
N1 H1A . 0.9 ?
N1 H1B . 0.9 ?
C1 C3 . 1.480(11) ?
C1 C2 . 1.528(10) ?
C1 H1 . 0.98 ?
C2 H2A . 0.96 ?
C2 H2B . 0.96 ?
C2 H2C . 0.96 ?
C3 H3A . 0.96 ?
C3 H3B . 0.96 ?
C3 H3C . 0.96 ?
P1 C4 . 1.814(5) ?
P1 C16 . 1.825(5) ?
P1 C10 . 1.829(5) ?
C4 C5 . 1.391(7) ?
C4 C9 . 1.402(7) ?
C5 C6 . 1.396(9) ?
C5 H5 . 0.93 ?
C6 C7 . 1.373(10) ?
C6 H6 . 0.93 ?
C7 C8 . 1.385(10) ?
C7 H7 . 0.93 ?
C8 C9 . 1.383(8) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
C10 C15 . 1.391(7) ?
C10 C11 . 1.406(7) ?
C11 C12 . 1.380(8) ?
C11 H11 . 0.93 ?
C12 C13 . 1.392(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.361(9) ?
C13 H13 . 0.93 ?
C14 C15 . 1.392(8) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 C17 . 1.378(8) ?
C16 C21 . 1.381(8) ?
C17 C18 . 1.401(9) ?
C17 H17 . 0.93 ?
C18 C19 . 1.352(12) ?
C18 H18 . 0.93 ?
C19 C20 . 1.360(11) ?
C19 H19 . 0.93 ?
C20 C21 . 1.395(8) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Pt1 P1 . . 177.41(14) ?
N1 Pt1 I2 . . 86.52(16) ?
P1 Pt1 I2 . . 93.99(3) ?
N1 Pt1 I1 . . 87.76(15) ?
P1 Pt1 I1 . . 91.51(3) ?
I2 Pt1 I1 . . 172.327(16) ?
C1 N1 Pt1 . . 120.4(4) ?
C1 N1 H1A . . 107.2 ?
Pt1 N1 H1A . . 107.2 ?
C1 N1 H1B . . 107.2 ?
Pt1 N1 H1B . . 107.2 ?
H1A N1 H1B . . 106.9 ?
C3 C1 N1 . . 112.3(6) ?
C3 C1 C2 . . 114.7(6) ?
N1 C1 C2 . . 109.1(6) ?
C3 C1 H1 . . 106.7 ?
N1 C1 H1 . . 106.7 ?
C2 C1 H1 . . 106.7 ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C3 H3A . . 109.5 ?
C1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C4 P1 C16 . . 108.7(2) ?
C4 P1 C10 . . 100.4(2) ?
C16 P1 C10 . . 102.8(2) ?
C4 P1 Pt1 . . 115.95(16) ?
C16 P1 Pt1 . . 109.99(17) ?
C10 P1 Pt1 . . 117.84(15) ?
C5 C4 C9 . . 118.1(5) ?
C5 C4 P1 . . 121.6(4) ?
C9 C4 P1 . . 120.3(4) ?
C4 C5 C6 . . 120.0(6) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 121.3(6) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 C8 . . 119.2(6) ?
C6 C7 H7 . . 120.4 ?
C8 C7 H7 . . 120.4 ?
C9 C8 C7 . . 120.1(6) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C4 . . 121.2(6) ?
C8 C9 H9 . . 119.4 ?
C4 C9 H9 . . 119.4 ?
C15 C10 C11 . . 119.3(5) ?
C15 C10 P1 . . 122.3(4) ?
C11 C10 P1 . . 118.5(4) ?
C12 C11 C10 . . 120.1(5) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 119.7(6) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C14 C13 C12 . . 120.5(5) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.6(6) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C14 C15 C10 . . 119.7(5) ?
C14 C15 H15 . . 120.1 ?
C10 C15 H15 . . 120.1 ?
C17 C16 C21 . . 119.1(5) ?
C17 C16 P1 . . 123.5(4) ?
C21 C16 P1 . . 117.2(4) ?
C16 C17 C18 . . 119.0(7) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C19 C18 C17 . . 121.6(7) ?
C19 C18 H18 . . 119.2 ?
C17 C18 H18 . . 119.2 ?
C18 C19 C20 . . 119.6(6) ?
C18 C19 H19 . . 120.2 ?
C20 C19 H19 . . 120.2 ?
C19 C20 C21 . . 120.1(6) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C16 C21 C20 . . 120.5(6) ?
C16 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?

_database_code_depnum_ccdc_archive 'CCDC 982662'
