# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'T. Keith Hollis'
'Joon Cho.'
'Theodore R Helgert'
'Edward J Valente'

_publ_contact_author_name        'T. Keith Hollis'
_publ_contact_author_email       HOLLIS@OLEMISS.EDU

_publ_section_title              
;
An improved method for the synthesis of zirconiuim
(CCC-N-heterocyclic carbene) pincer complexes and applications in
hydroamination
;

# Attachment 'mc074a1.cif'

data_mc074a
_database_code_depnum_ccdc_archive 'CCDC 684720'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H31 I2 N5 Zr1'
_chemical_formula_sum            'C22 H31 I2 N5 Zr'
_chemical_formula_weight         710.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9670 0.5600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1754(2)
_cell_length_b                   23.4958(4)
_cell_length_c                   10.8780(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.495(2)
_cell_angle_gamma                90.00
_cell_volume                     2572.17(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    12058
_cell_measurement_theta_min      3.0812
_cell_measurement_theta_max      30.4998

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5239
_exptl_crystal_size_mid          0.3841
_exptl_crystal_size_min          0.2732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    2.846
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.318
_exptl_absorpt_correction_T_max  0.506
_exptl_absorpt_process_details   'CrysAlis (Oxford Diffraction)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20493
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         30.64
_reflns_number_total             7719
_reflns_number_gt                6112
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WinGX
_computing_publication_material  WinGX

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+6.6851P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0
_refine_ls_number_reflns         7719
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1407(4) 0.25331(14) 1.0188(3) 0.0304(8) Uani 1 1 d . . .
H1A H 0.0843 0.2824 1.0420 0.036 Uiso 1 1 calc R . .
C2 C 0.2737(4) 0.24964(15) 1.0506(3) 0.0310(8) Uani 1 1 d . . .
H2A H 0.3293 0.2758 1.1006 0.037 Uiso 1 1 calc R . .
C3 C 0.2094(3) 0.17350(14) 0.9315(3) 0.0234(6) Uani 1 1 d . . .
C4 C -0.0144(3) 0.03937(13) 0.7105(3) 0.0210(6) Uani 1 1 d . . .
C5 C -0.1737(3) -0.01666(15) 0.6071(3) 0.0272(7) Uani 1 1 d . . .
H5A H -0.2146 -0.0481 0.5618 0.033 Uiso 1 1 calc R . .
C6 C -0.2356(3) 0.02991(15) 0.6434(3) 0.0259(7) Uani 1 1 d . . .
H6A H -0.3281 0.0379 0.6283 0.031 Uiso 1 1 calc R . .
C7 C -0.1462(3) 0.11660(14) 0.7703(3) 0.0229(6) Uani 1 1 d . . .
C8 C -0.2662(4) 0.14436(16) 0.7760(3) 0.0293(7) Uani 1 1 d . . .
H8A H -0.3482 0.1291 0.7367 0.035 Uiso 1 1 calc R . .
C9 C -0.2611(4) 0.19530(16) 0.8413(3) 0.0320(8) Uani 1 1 d . . .
H9A H -0.3414 0.2152 0.8468 0.038 Uiso 1 1 calc R . .
C10 C -0.1416(4) 0.21783(15) 0.8988(3) 0.0291(7) Uani 1 1 d . . .
H10A H -0.1390 0.2528 0.9431 0.035 Uiso 1 1 calc R . .
C11 C -0.0257(3) 0.18777(14) 0.8898(3) 0.0241(6) Uani 1 1 d . . .
C12 C -0.0237(3) 0.13685(13) 0.8263(3) 0.0215(6) Uani 1 1 d . . .
C13 C 0.4503(4) 0.17840(17) 1.0169(4) 0.0329(8) Uani 1 1 d . . .
H13A H 0.5129 0.2104 1.0381 0.039 Uiso 1 1 calc R . .
H13B H 0.4702 0.1611 0.9387 0.039 Uiso 1 1 calc R . .
C14 C 0.4718(4) 0.13454(16) 1.1192(4) 0.0339(8) Uani 1 1 d . . .
H14A H 0.5647 0.1209 1.1275 0.041 Uiso 1 1 calc R . .
H14B H 0.4130 0.1016 1.0949 0.041 Uiso 1 1 calc R . .
C15 C 0.4452(4) 0.15612(17) 1.2452(4) 0.0380(9) Uani 1 1 d . . .
H15A H 0.5044 0.1889 1.2700 0.046 Uiso 1 1 calc R . .
H15B H 0.3524 0.1699 1.2370 0.046 Uiso 1 1 calc R . .
C16 C 0.4663(5) 0.1117(2) 1.3472(4) 0.0473(11) Uani 1 1 d . . .
H16A H 0.4479 0.1285 1.4253 0.057 Uiso 1 1 calc R . .
H16B H 0.5585 0.0983 1.3573 0.057 Uiso 1 1 calc R . .
H16C H 0.4062 0.0796 1.3248 0.057 Uiso 1 1 calc R . .
C17 C 0.0603(3) -0.05314(14) 0.6312(3) 0.0257(7) Uani 1 1 d . . .
H17A H 0.1498 -0.0357 0.6469 0.031 Uiso 1 1 calc R . .
H17B H 0.0451 -0.0665 0.5439 0.031 Uiso 1 1 calc R . .
C18 C 0.0565(4) -0.10352(15) 0.7164(3) 0.0280(7) Uani 1 1 d . . .
H18A H -0.0346 -0.1194 0.7060 0.034 Uiso 1 1 calc R . .
H18B H 0.0801 -0.0911 0.8038 0.034 Uiso 1 1 calc R . .
C19 C 0.1527(4) -0.14902(18) 0.6877(4) 0.0367(9) Uani 1 1 d . . .
H19A H 0.1338 -0.1587 0.5982 0.044 Uiso 1 1 calc R . .
H19B H 0.2443 -0.1338 0.7047 0.044 Uiso 1 1 calc R . .
C20 C 0.1441(8) -0.2017(2) 0.7623(5) 0.0747(18) Uani 1 1 d . . .
H20A H 0.2087 -0.2297 0.7412 0.090 Uiso 1 1 calc R . .
H20B H 0.0543 -0.2177 0.7439 0.090 Uiso 1 1 calc R . .
H20C H 0.1636 -0.1926 0.8510 0.090 Uiso 1 1 calc R . .
C21 C 0.2802(6) -0.0146(2) 0.9942(4) 0.0518(12) Uani 1 1 d . A 1
H21A H 0.3435 -0.0069 1.0693 0.062 Uiso 1 1 calc R A 1
H21B H 0.3286 -0.0271 0.9274 0.062 Uiso 1 1 calc R A 1
H21C H 0.2186 -0.0446 1.0115 0.062 Uiso 1 1 calc R A 1
C22 C 0.1323(4) 0.0529(2) 1.0583(4) 0.0398(9) Uani 1 1 d . A 1
H22A H 0.0782 0.0207 1.0782 0.048 Uiso 1 1 calc R A 1
H22B H 0.0744 0.0855 1.0326 0.048 Uiso 1 1 calc R A 1
H22C H 0.1954 0.0633 1.1319 0.048 Uiso 1 1 calc R A 1
N1 N 0.1032(3) 0.20635(11) 0.9459(2) 0.0243(6) Uani 1 1 d . . .
N2 N 0.3140(3) 0.20058(12) 0.9968(3) 0.0265(6) Uani 1 1 d . . .
N3 N -0.1366(3) 0.06369(11) 0.7072(2) 0.0215(5) Uani 1 1 d . . .
N4 N -0.0395(3) -0.00991(11) 0.6483(2) 0.0232(5) Uani 1 1 d . . .
N5 N 0.2059(3) 0.03698(14) 0.9560(3) 0.0324(7) Uani 1 1 d . A 1
Zr Zr 0.17222(3) 0.089430(12) 0.81153(3) 0.01836(6) Uani 1 1 d . . .
I1 I 0.15614(2) 0.165672(9) 0.58815(2) 0.02848(5) Uani 1 1 d . A .
I2 I 0.40006(3) 0.045827(14) 0.72051(3) 0.03911(8) Uani 0.9372(7) 1 d P A 1
I2A I 0.1862(5) 0.0269(2) 1.0124(5) 0.039 Uiso 0.0628(7) 1 d P A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.050(2) 0.0178(14) 0.0241(15) -0.0060(12) 0.0075(14) -0.0016(14)
C2 0.047(2) 0.0207(15) 0.0251(15) -0.0056(12) 0.0066(15) -0.0068(15)
C3 0.0310(16) 0.0207(14) 0.0187(13) -0.0033(11) 0.0041(12) -0.0046(12)
C4 0.0272(14) 0.0169(13) 0.0194(13) 0.0026(11) 0.0049(11) -0.0037(12)
C5 0.0275(16) 0.0270(16) 0.0267(15) -0.0022(13) 0.0029(13) -0.0086(13)
C6 0.0234(14) 0.0281(16) 0.0258(15) 0.0021(13) 0.0020(12) -0.0063(13)
C7 0.0278(15) 0.0192(14) 0.0225(13) 0.0055(11) 0.0066(12) -0.0004(12)
C8 0.0275(16) 0.0276(16) 0.0336(17) 0.0087(14) 0.0079(14) 0.0011(14)
C9 0.0320(17) 0.0309(17) 0.0365(18) 0.0113(14) 0.0160(14) 0.0078(14)
C10 0.0418(18) 0.0234(15) 0.0253(15) 0.0040(12) 0.0155(14) 0.0062(14)
C11 0.0331(16) 0.0205(14) 0.0199(13) 0.0008(11) 0.0083(12) 0.0000(13)
C12 0.0285(15) 0.0193(14) 0.0175(12) 0.0009(11) 0.0056(11) 0.0009(12)
C13 0.0316(17) 0.0339(19) 0.0347(17) -0.0121(15) 0.0099(14) -0.0094(15)
C14 0.0285(17) 0.0284(17) 0.044(2) -0.0116(15) 0.0020(15) -0.0012(14)
C15 0.045(2) 0.0323(19) 0.0373(19) -0.0032(16) 0.0063(17) 0.0017(17)
C16 0.049(2) 0.043(2) 0.051(2) 0.008(2) 0.011(2) -0.003(2)
C17 0.0276(15) 0.0226(15) 0.0281(15) -0.0043(12) 0.0078(12) -0.0053(13)
C18 0.0342(17) 0.0270(16) 0.0235(15) -0.0003(12) 0.0061(13) 0.0005(14)
C19 0.039(2) 0.040(2) 0.0310(18) -0.0021(16) 0.0025(15) 0.0122(17)
C20 0.127(5) 0.041(3) 0.059(3) 0.015(2) 0.022(3) 0.040(3)
C21 0.080(3) 0.038(2) 0.039(2) 0.0137(18) 0.011(2) 0.012(2)
C22 0.040(2) 0.047(2) 0.0335(18) 0.0172(17) 0.0102(16) -0.0015(18)
N1 0.0372(15) 0.0159(12) 0.0207(12) -0.0018(10) 0.0067(11) 0.0002(11)
N2 0.0375(15) 0.0211(13) 0.0215(12) -0.0042(10) 0.0066(11) -0.0068(12)
N3 0.0238(12) 0.0176(12) 0.0230(12) 0.0028(10) 0.0033(10) -0.0036(10)
N4 0.0290(13) 0.0179(12) 0.0230(12) -0.0018(10) 0.0043(10) -0.0060(11)
N5 0.0483(18) 0.0357(16) 0.0147(12) 0.0084(11) 0.0102(12) -0.0057(14)
Zr 0.02366(13) 0.01483(12) 0.01678(12) -0.00079(10) 0.00361(10) -0.00183(11)
I1 0.04340(13) 0.02007(9) 0.02228(9) 0.00284(8) 0.00594(8) -0.00322(9)
I2 0.02731(12) 0.04901(17) 0.04238(15) -0.00144(12) 0.00967(10) 0.00679(11)

_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
C1 C2 1.349(6) . ?
C1 N1 1.380(4) . ?
C1 H1A 0.9500 . ?
C2 N2 1.382(4) . ?
C2 H2A 0.9500 . ?
C3 N2 1.348(4) . ?
C3 N1 1.356(4) . ?
C3 Zr 2.367(3) . ?
C4 N4 1.347(4) . ?
C4 N3 1.364(4) . ?
C4 Zr 2.362(3) . ?
C5 C6 1.351(5) . ?
C5 N4 1.381(4) . ?
C5 H5A 0.9500 . ?
C6 N3 1.386(4) . ?
C6 H6A 0.9500 . ?
C7 C12 1.388(5) . ?
C7 C8 1.394(5) . ?
C7 N3 1.431(4) . ?
C8 C9 1.389(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.388(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.391(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(4) . ?
C11 N1 1.430(4) . ?
C12 Zr 2.310(3) . ?
C13 N2 1.467(5) . ?
C13 C14 1.509(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N4 1.468(4) . ?
C17 C18 1.507(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.513(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.491(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N5 1.456(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N5 1.479(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N5 Zr 1.986(3) . ?
Zr I2A 2.620(5) . ?
Zr I2 2.8431(4) . ?
Zr I1 3.0038(4) . ?

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
C2 C1 N1 106.2(3) . . ?
C2 C1 H1A 126.9 . . ?
N1 C1 H1A 126.9 . . ?
C1 C2 N2 107.1(3) . . ?
C1 C2 H2A 126.5 . . ?
N2 C2 H2A 126.5 . . ?
N2 C3 N1 104.5(3) . . ?
N2 C3 Zr 137.2(2) . . ?
N1 C3 Zr 118.2(2) . . ?
N4 C4 N3 104.0(3) . . ?
N4 C4 Zr 137.9(2) . . ?
N3 C4 Zr 118.1(2) . . ?
C6 C5 N4 107.1(3) . . ?
C6 C5 H5A 126.5 . . ?
N4 C5 H5A 126.5 . . ?
C5 C6 N3 105.9(3) . . ?
C5 C6 H6A 127.0 . . ?
N3 C6 H6A 127.0 . . ?
C12 C7 C8 123.8(3) . . ?
C12 C7 N3 112.8(3) . . ?
C8 C7 N3 123.4(3) . . ?
C9 C8 C7 117.3(3) . . ?
C9 C8 H8A 121.3 . . ?
C7 C8 H8A 121.3 . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 H10A 121.0 . . ?
C11 C10 H10A 121.0 . . ?
C12 C11 C10 123.3(3) . . ?
C12 C11 N1 113.4(3) . . ?
C10 C11 N1 123.3(3) . . ?
C11 C12 C7 115.9(3) . . ?
C11 C12 Zr 121.9(2) . . ?
C7 C12 Zr 122.2(2) . . ?
N2 C13 C14 112.5(3) . . ?
N2 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 114.3(3) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 113.9(4) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 112.6(3) . . ?
N4 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 110.6(3) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 112.5(4) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 H21A 109.5 . . ?
N5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 N1 C1 111.3(3) . . ?
C3 N1 C11 118.2(3) . . ?
C1 N1 C11 130.4(3) . . ?
C3 N2 C2 110.9(3) . . ?
C3 N2 C13 124.4(3) . . ?
C2 N2 C13 124.5(3) . . ?
C4 N3 C6 111.5(3) . . ?
C4 N3 C7 118.6(3) . . ?
C6 N3 C7 129.9(3) . . ?
C4 N4 C5 111.5(3) . . ?
C4 N4 C17 125.1(3) . . ?
C5 N4 C17 123.3(3) . . ?
C21 N5 C22 107.2(3) . . ?
C21 N5 Zr 139.8(3) . . ?
C22 N5 Zr 113.0(3) . . ?
N5 Zr C12 107.11(12) . . ?
N5 Zr C4 95.28(12) . . ?
C12 Zr C4 68.28(11) . . ?
N5 Zr C3 94.99(12) . . ?
C12 Zr C3 68.20(11) . . ?
C4 Zr C3 136.40(11) . . ?
N5 Zr I2A 8.29(14) . . ?
C12 Zr I2A 98.84(13) . . ?
C4 Zr I2A 92.82(12) . . ?
C3 Zr I2A 91.38(13) . . ?
N5 Zr I2 89.85(10) . . ?
C12 Zr I2 162.66(7) . . ?
C4 Zr I2 107.42(8) . . ?
C3 Zr I2 114.86(8) . . ?
I2A Zr I2 98.14(11) . . ?
N5 Zr I1 172.85(10) . . ?
C12 Zr I1 79.88(7) . . ?
C4 Zr I1 88.67(7) . . ?
C3 Zr I1 86.18(8) . . ?
I2A Zr I1 177.53(11) . . ?
I2 Zr I1 83.278(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.2(4) . . . . ?
N4 C5 C6 N3 -0.6(4) . . . . ?
C12 C7 C8 C9 0.3(5) . . . . ?
N3 C7 C8 C9 179.5(3) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C9 C10 C11 N1 -179.4(3) . . . . ?
C10 C11 C12 C7 0.1(5) . . . . ?
N1 C11 C12 C7 179.7(3) . . . . ?
C10 C11 C12 Zr 179.0(2) . . . . ?
N1 C11 C12 Zr -1.4(4) . . . . ?
C8 C7 C12 C11 -0.3(5) . . . . ?
N3 C7 C12 C11 -179.6(3) . . . . ?
C8 C7 C12 Zr -179.2(2) . . . . ?
N3 C7 C12 Zr 1.5(4) . . . . ?
N2 C13 C14 C15 -59.2(4) . . . . ?
C13 C14 C15 C16 179.7(3) . . . . ?
N4 C17 C18 C19 175.1(3) . . . . ?
C17 C18 C19 C20 -175.1(4) . . . . ?
N2 C3 N1 C1 0.1(4) . . . . ?
Zr C3 N1 C1 179.4(2) . . . . ?
N2 C3 N1 C11 -178.1(3) . . . . ?
Zr C3 N1 C11 1.2(4) . . . . ?
C2 C1 N1 C3 0.0(4) . . . . ?
C2 C1 N1 C11 178.0(3) . . . . ?
C12 C11 N1 C3 0.1(4) . . . . ?
C10 C11 N1 C3 179.7(3) . . . . ?
C12 C11 N1 C1 -177.7(3) . . . . ?
C10 C11 N1 C1 1.9(5) . . . . ?
N1 C3 N2 C2 -0.2(4) . . . . ?
Zr C3 N2 C2 -179.3(3) . . . . ?
N1 C3 N2 C13 174.8(3) . . . . ?
Zr C3 N2 C13 -4.2(5) . . . . ?
C1 C2 N2 C3 0.3(4) . . . . ?
C1 C2 N2 C13 -174.8(3) . . . . ?
C14 C13 N2 C3 -79.9(4) . . . . ?
C14 C13 N2 C2 94.5(4) . . . . ?
N4 C4 N3 C6 -0.2(3) . . . . ?
Zr C4 N3 C6 179.0(2) . . . . ?
N4 C4 N3 C7 177.6(3) . . . . ?
Zr C4 N3 C7 -3.2(3) . . . . ?
C5 C6 N3 C4 0.5(4) . . . . ?
C5 C6 N3 C7 -177.0(3) . . . . ?
C12 C7 N3 C4 1.2(4) . . . . ?
C8 C7 N3 C4 -178.1(3) . . . . ?
C12 C7 N3 C6 178.5(3) . . . . ?
C8 C7 N3 C6 -0.8(5) . . . . ?
N3 C4 N4 C5 -0.2(3) . . . . ?
Zr C4 N4 C5 -179.2(3) . . . . ?
N3 C4 N4 C17 -176.9(3) . . . . ?
Zr C4 N4 C17 4.1(5) . . . . ?
C6 C5 N4 C4 0.5(4) . . . . ?
C6 C5 N4 C17 177.3(3) . . . . ?
C18 C17 N4 C4 102.7(4) . . . . ?
C18 C17 N4 C5 -73.7(4) . . . . ?
C21 N5 Zr C12 158.5(5) . . . . ?
C22 N5 Zr C12 -19.8(3) . . . . ?
C21 N5 Zr C4 89.6(5) . . . . ?
C22 N5 Zr C4 -88.7(3) . . . . ?
C21 N5 Zr C3 -132.8(5) . . . . ?
C22 N5 Zr C3 48.9(3) . . . . ?
C21 N5 Zr I2A 162.7(13) . . . . ?
C22 N5 Zr I2A -15.6(9) . . . . ?
C21 N5 Zr I2 -17.9(5) . . . . ?
C22 N5 Zr I2 163.9(3) . . . . ?
C21 N5 Zr I1 -33.7(11) . . . . ?
C22 N5 Zr I1 148.0(6) . . . . ?
C11 C12 Zr N5 90.0(3) . . . . ?
C7 C12 Zr N5 -91.2(3) . . . . ?
C11 C12 Zr C4 178.9(3) . . . . ?
C7 C12 Zr C4 -2.3(2) . . . . ?
C11 C12 Zr C3 1.5(2) . . . . ?
C7 C12 Zr C3 -179.7(3) . . . . ?
C11 C12 Zr I2A 89.4(3) . . . . ?
C7 C12 Zr I2A -91.8(3) . . . . ?
C11 C12 Zr I2 -102.3(3) . . . . ?
C7 C12 Zr I2 76.5(4) . . . . ?
C11 C12 Zr I1 -88.5(2) . . . . ?
C7 C12 Zr I1 90.3(2) . . . . ?
N4 C4 Zr N5 -72.0(3) . . . . ?
N3 C4 Zr N5 109.1(2) . . . . ?
N4 C4 Zr C12 -178.3(4) . . . . ?
N3 C4 Zr C12 2.8(2) . . . . ?
N4 C4 Zr C3 -174.9(3) . . . . ?
N3 C4 Zr C3 6.2(3) . . . . ?
N4 C4 Zr I2A -79.9(3) . . . . ?
N3 C4 Zr I2A 101.2(2) . . . . ?
N4 C4 Zr I2 19.5(3) . . . . ?
N3 C4 Zr I2 -159.4(2) . . . . ?
N4 C4 Zr I1 102.0(3) . . . . ?
N3 C4 Zr I1 -76.8(2) . . . . ?
N2 C3 Zr N5 71.2(3) . . . . ?
N1 C3 Zr N5 -107.8(3) . . . . ?
N2 C3 Zr C12 177.6(4) . . . . ?
N1 C3 Zr C12 -1.3(2) . . . . ?
N2 C3 Zr C4 174.2(3) . . . . ?
N1 C3 Zr C4 -4.8(3) . . . . ?
N2 C3 Zr I2A 78.7(3) . . . . ?
N1 C3 Zr I2A -100.3(3) . . . . ?
N2 C3 Zr I2 -21.0(4) . . . . ?
N1 C3 Zr I2 160.1(2) . . . . ?
N2 C3 Zr I1 -101.8(3) . . . . ?
N1 C3 Zr I1 79.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        30.64
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         2.620
_refine_diff_density_min         -2.273
_refine_diff_density_rms         0.133