# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ti
_database_code_depnum_ccdc_archive 'CCDC 1050370'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        Ti

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C19 H33 Cl4 N O Ti '

_chemical_formula_sum            'C19 H33 Cl4 N O Ti'

_chemical_formula_weight         481.16



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'
O O 0.0106 0.0060 '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'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   C2/c

_symmetry_space_group_name_Hall  '-C 2yc '

loop_

_symmetry_equiv_pos_as_xyz








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



_cell_length_a                   11.0722(3)

_cell_length_b                   22.8910(7)

_cell_length_c                   19.0774(6)

_cell_angle_alpha                90.00

_cell_angle_beta                 98.0330(10)

_cell_angle_gamma                90.00

_cell_volume                     4787.8(2)

_cell_formula_units_Z            8

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    7976

_cell_measurement_theta_min      2.44

_cell_measurement_theta_max      28.40



_exptl_crystal_description       Rectangular

_exptl_crystal_colour            white

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.335

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             2016

_exptl_absorpt_coefficient_mu    0.813

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.7112

_exptl_absorpt_correction_T_max  0.9232

_exptl_absorpt_process_details   'SADABS (Bruker 2012)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      173(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  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            15513

_diffrn_reflns_av_R_equivalents  0.0230

_diffrn_reflns_av_sigmaI/netI    0.0267

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       14

_diffrn_reflns_limit_k_min       -30

_diffrn_reflns_limit_k_max       27

_diffrn_reflns_limit_l_min       -25

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         1.78

_diffrn_reflns_theta_max         28.43

_reflns_number_total             5095

_reflns_number_gt                4184

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker APEXII'

_computing_cell_refinement       'Bruker APEXII'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_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.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+10.9591P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         5095

_refine_ls_number_parameters     247

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0482

_refine_ls_R_factor_gt           0.0367

_refine_ls_wR_factor_ref         0.0994

_refine_ls_wR_factor_gt          0.0923

_refine_ls_goodness_of_fit_ref   1.052

_refine_ls_restrained_S_all      1.052

_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 0.25213(19) 0.33028(10) 0.21663(11) 0.0195(4) Uani 1 1 d . . .
C2 C 0.20457(19) 0.27367(10) 0.20468(11) 0.0195(4) Uani 1 1 d . . .
C3 C 0.2483(2) 0.23188(10) 0.25537(11) 0.0208(4) Uani 1 1 d . . .
H3 H 0.2196 0.1929 0.2484 0.025 Uiso 1 1 calc R . .
C4 C 0.3309(2) 0.24375(10) 0.31529(11) 0.0216(5) Uani 1 1 d . . .
C5 C 0.3666(2) 0.30143(10) 0.32741(11) 0.0228(5) Uani 1 1 d . . .
H5 H 0.4191 0.3110 0.3695 0.027 Uiso 1 1 calc R . .
C6 C 0.32738(19) 0.34546(10) 0.27956(11) 0.0219(5) Uani 1 1 d . . .
C7 C 0.10848(19) 0.25792(10) 0.14141(11) 0.0222(5) Uani 1 1 d . . .
C8 C 0.0608(2) 0.19534(11) 0.14630(14) 0.0338(6) Uani 1 1 d . . .
H8A H 0.1281 0.1677 0.1455 0.051 Uiso 1 1 calc R . .
H8B H -0.0023 0.1877 0.1060 0.051 Uiso 1 1 calc R . .
H8C H 0.0261 0.1907 0.1905 0.051 Uiso 1 1 calc R . .
C9 C 0.1621(2) 0.26251(12) 0.07137(12) 0.0309(6) Uani 1 1 d . . .
H9A H 0.1929 0.3022 0.0662 0.046 Uiso 1 1 calc R . .
H9B H 0.0985 0.2538 0.0317 0.046 Uiso 1 1 calc R . .
H9C H 0.2291 0.2345 0.0717 0.046 Uiso 1 1 calc R . .
C10 C -0.00236(19) 0.29888(11) 0.14032(12) 0.0239(5) Uani 1 1 d . . .
H10A H -0.0355 0.2954 0.1852 0.036 Uiso 1 1 calc R . .
H10B H -0.0651 0.2879 0.1011 0.036 Uiso 1 1 calc R . .
H10C H 0.0232 0.3393 0.1340 0.036 Uiso 1 1 calc R . .
C11 C 0.3832(2) 0.19630(10) 0.36753(12) 0.0246(5) Uani 1 1 d . . .
C12 C 0.3357(3) 0.13572(12) 0.34549(16) 0.0473(8) Uani 1 1 d . . .
H12A H 0.2469 0.1348 0.3442 0.071 Uiso 1 1 calc R . .
H12B H 0.3733 0.1068 0.3797 0.071 Uiso 1 1 calc R . .
H12C H 0.3563 0.1265 0.2984 0.071 Uiso 1 1 calc R . .
C13 C 0.5227(2) 0.19676(14) 0.37215(15) 0.0408(7) Uani 1 1 d . . .
H13A H 0.5575 0.1667 0.4056 0.061 Uiso 1 1 calc R . .
H13B H 0.5541 0.2352 0.3884 0.061 Uiso 1 1 calc R . .
H13C H 0.5457 0.1887 0.3253 0.061 Uiso 1 1 calc R . .
C14 C 0.3481(2) 0.20991(12) 0.44083(12) 0.0326(6) Uani 1 1 d . . .
H14A H 0.2590 0.2103 0.4381 0.049 Uiso 1 1 calc R . .
H14B H 0.3807 0.2482 0.4567 0.049 Uiso 1 1 calc R . .
H14C H 0.3821 0.1799 0.4746 0.049 Uiso 1 1 calc R . .
C15 C 0.36577(19) 0.40726(10) 0.29625(12) 0.0223(5) Uani 1 1 d . . .
H15A H 0.3910 0.4253 0.2534 0.027 Uiso 1 1 calc R . .
H15B H 0.4377 0.4070 0.3335 0.027 Uiso 1 1 calc R . .
C16 C 0.2160(2) 0.42011(11) 0.38425(12) 0.0266(5) Uani 1 1 d . . .
H16A H 0.1935 0.3787 0.3746 0.032 Uiso 1 1 calc R . .
H16B H 0.1406 0.4416 0.3904 0.032 Uiso 1 1 calc R . .
C17 C 0.3031(3) 0.42342(15) 0.45231(14) 0.0450(7) Uani 1 1 d . . .
H17A H 0.3782 0.4024 0.4468 0.067 Uiso 1 1 calc R . .
H17B H 0.2653 0.4056 0.4906 0.067 Uiso 1 1 calc R . .
H17C H 0.3223 0.4644 0.4638 0.067 Uiso 1 1 calc R . .
C18 C 0.3108(2) 0.50693(11) 0.33145(14) 0.0308(5) Uani 1 1 d . . .
H18A H 0.3389 0.5208 0.2873 0.037 Uiso 1 1 calc R . .
H18B H 0.3813 0.5080 0.3695 0.037 Uiso 1 1 calc R . .
C19 C 0.2126(2) 0.54791(11) 0.35051(15) 0.0344(6) Uani 1 1 d . . .
H19A H 0.1401 0.5448 0.3148 0.052 Uiso 1 1 calc R . .
H19B H 0.2430 0.5882 0.3520 0.052 Uiso 1 1 calc R . .
H19C H 0.1912 0.5372 0.3970 0.052 Uiso 1 1 calc R . .
Cl1 Cl 0.35639(6) 0.39378(4) 0.03954(4) 0.04376(19) Uani 1 1 d . . .
Cl2 Cl 0.08911(5) 0.48035(3) 0.17825(3) 0.02775(14) Uani 1 1 d . . .
Cl3 Cl 0.35600(5) 0.50631(3) 0.13806(4) 0.03629(16) Uani 1 1 d . . .
Cl4 Cl 0.06661(5) 0.42754(3) 0.01896(3) 0.03265(15) Uani 1 1 d . . .
N1 N 0.26666(17) 0.44474(8) 0.32119(11) 0.0211(4) Uani 1 1 d . . .
O1 O 0.22732(14) 0.37277(7) 0.16675(8) 0.0243(3) Uani 1 1 d . . .
Ti1 Ti 0.22000(3) 0.432489(18) 0.10850(2) 0.02087(11) Uani 1 1 d . . .
H1N H 0.212(2) 0.4453(11) 0.2897(14) 0.021(7) Uiso 1 1 d . . .






_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 O1 1.361(3) . ?
C1 C2 1.405(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.398(3) . ?
C2 C7 1.536(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 C11 1.532(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C15 1.499(3) . ?
C7 C8 1.534(3) . ?
C7 C9 1.540(3) . ?
C7 C10 1.542(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.521(4) . ?
C11 C14 1.535(3) . ?
C11 C13 1.535(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N1 1.521(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N1 1.506(3) . ?
C16 C17 1.507(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.509(3) . ?
C18 C19 1.518(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Cl1 Ti1 2.3133(7) . ?
Cl2 Ti1 2.3687(6) . ?
Cl3 Ti1 2.2811(8) . ?
Cl4 Ti1 2.2371(7) . ?
N1 H1N 0.79(3) . ?
O1 Ti1 1.7564(16) . ?



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 C1 C2 120.73(19) . . ?
O1 C1 C6 117.2(2) . . ?
C2 C1 C6 122.0(2) . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 C7 121.2(2) . . ?
C1 C2 C7 123.13(19) . . ?
C4 C3 C2 124.1(2) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 C11 122.9(2) . . ?
C5 C4 C11 119.5(2) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C15 119.5(2) . . ?
C1 C6 C15 122.1(2) . . ?
C8 C7 C2 112.20(19) . . ?
C8 C7 C9 107.1(2) . . ?
C2 C7 C9 110.92(18) . . ?
C8 C7 C10 106.77(19) . . ?
C2 C7 C10 109.29(17) . . ?
C9 C7 C10 110.45(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 112.5(2) . . ?
C12 C11 C14 108.4(2) . . ?
C4 C11 C14 109.14(19) . . ?
C12 C11 C13 109.2(2) . . ?
C4 C11 C13 108.56(19) . . ?
C14 C11 C13 109.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C15 N1 113.79(17) . . ?
C6 C15 H15A 108.8 . . ?
N1 C15 H15A 108.8 . . ?
C6 C15 H15B 108.8 . . ?
N1 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
N1 C16 C17 113.85(19) . . ?
N1 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 112.61(19) . . ?
N1 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 N1 C18 113.54(18) . . ?
C16 N1 C15 113.86(18) . . ?
C18 N1 C15 109.77(17) . . ?
C16 N1 H1N 106.5(19) . . ?
C18 N1 H1N 106.4(19) . . ?
C15 N1 H1N 106.2(19) . . ?
C1 O1 Ti1 170.10(15) . . ?
O1 Ti1 Cl4 114.00(6) . . ?
O1 Ti1 Cl3 116.72(6) . . ?
Cl4 Ti1 Cl3 129.10(3) . . ?
O1 Ti1 Cl1 94.91(6) . . ?
Cl4 Ti1 Cl1 91.87(3) . . ?
Cl3 Ti1 Cl1 87.91(3) . . ?
O1 Ti1 Cl2 88.99(5) . . ?
Cl4 Ti1 Cl2 89.63(2) . . ?
Cl3 Ti1 Cl2 87.31(3) . . ?
Cl1 Ti1 Cl2 174.83(3) . . ?



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 C1 C2 C3 172.21(18) . . . . ?
C6 C1 C2 C3 -7.3(3) . . . . ?
O1 C1 C2 C7 -9.2(3) . . . . ?
C6 C1 C2 C7 171.30(19) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C7 C2 C3 C4 -177.08(19) . . . . ?
C2 C3 C4 C5 3.9(3) . . . . ?
C2 C3 C4 C11 -176.1(2) . . . . ?
C3 C4 C5 C6 -3.8(3) . . . . ?
C11 C4 C5 C6 176.1(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C15 178.25(19) . . . . ?
O1 C1 C6 C5 -172.07(18) . . . . ?
C2 C1 C6 C5 7.4(3) . . . . ?
O1 C1 C6 C15 8.1(3) . . . . ?
C2 C1 C6 C15 -172.41(19) . . . . ?
C3 C2 C7 C8 5.8(3) . . . . ?
C1 C2 C7 C8 -172.7(2) . . . . ?
C3 C2 C7 C9 -113.9(2) . . . . ?
C1 C2 C7 C9 67.6(3) . . . . ?
C3 C2 C7 C10 124.1(2) . . . . ?
C1 C2 C7 C10 -54.5(3) . . . . ?
C3 C4 C11 C12 0.8(3) . . . . ?
C5 C4 C11 C12 -179.2(2) . . . . ?
C3 C4 C11 C14 -119.5(2) . . . . ?
C5 C4 C11 C14 60.5(3) . . . . ?
C3 C4 C11 C13 121.7(2) . . . . ?
C5 C4 C11 C13 -58.3(3) . . . . ?
C5 C6 C15 N1 -102.9(2) . . . . ?
C1 C6 C15 N1 76.9(3) . . . . ?
C17 C16 N1 C18 -55.3(3) . . . . ?
C17 C16 N1 C15 71.3(3) . . . . ?
C19 C18 N1 C16 -56.0(3) . . . . ?
C19 C18 N1 C15 175.3(2) . . . . ?
C6 C15 N1 C16 55.6(2) . . . . ?
C6 C15 N1 C18 -175.88(19) . . . . ?
C2 C1 O1 Ti1 -150.4(7) . . . . ?
C6 C1 O1 Ti1 29.1(9) . . . . ?
C1 O1 Ti1 Cl4 169.2(8) . . . . ?
C1 O1 Ti1 Cl3 -15.2(9) . . . . ?
C1 O1 Ti1 Cl1 74.9(8) . . . . ?
C1 O1 Ti1 Cl2 -101.7(8) . . . . ?



_diffrn_measured_fraction_theta_max 0.846

_diffrn_reflns_theta_full        25.242

_diffrn_measured_fraction_theta_full 1.000

_refine_diff_density_max         0.955

_refine_diff_density_min         -0.417

_refine_diff_density_rms         0.063

_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zr1
_database_code_depnum_ccdc_archive 'CCDC 1050371'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        zr1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H33 Cl4 N2 O Zr, C7 H8 '
_chemical_formula_sum            'C28 H41 Cl4 N2 O Zr'
_chemical_formula_weight         654.65

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   29.4978(15)
_cell_length_b                   11.1493(5)
_cell_length_c                   21.1407(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.578(2)
_cell_angle_gamma                90
_cell_volume                     6419.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5096
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.43

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             2712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.698
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       ' Phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18939
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.974
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5530
_reflns_number_gt                4623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER APEXII'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0607P)²+30.8205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5530
_refine_ls_number_parameters     371
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.81066(13) 0.5216(3) 0.68136(18) 0.0176(7) Uani 1 1 d . . . A 4
C2 C 0.76753(14) 0.5794(3) 0.67806(19) 0.0210(8) Uani 1 1 d . . . A 4
C3 C 0.72914(13) 0.5977(3) 0.61525(19) 0.0208(8) Uani 1 1 d . . . A 4
H3 H 0.7009 0.6365 0.6139 0.025 Uiso 1 1 calc R U . A 4
C4 C 0.73208(13) 0.5594(3) 0.55474(19) 0.0203(8) Uani 1 1 d . . . A 4
C5 C 0.77687(13) 0.5120(3) 0.55921(18) 0.0208(8) Uani 1 1 d . . . A 4
H5 H 0.7800 0.4903 0.5186 0.025 Uiso 1 1 calc R U . A 4
C6 C 0.81763(13) 0.4945(3) 0.62040(18) 0.0186(7) Uani 1 1 d . . . A 4
C7 C 0.76044(13) 0.6225(3) 0.74128(19) 0.0228(8) Uani 1 1 d . . . A 4
H7A H 0.7269 0.6505 0.7278 0.027 Uiso 1 1 calc R U . A 4
H7B H 0.7646 0.5546 0.7717 0.027 Uiso 1 1 calc R U . A 4
C8 C 0.81036(17) 0.8026(4) 0.7382(2) 0.0376(10) Uani 1 1 d . . . A 4
H8A H 0.7814 0.8380 0.7036 0.045 Uiso 1 1 calc R U . A 4
H8B H 0.8267 0.7555 0.7147 0.045 Uiso 1 1 calc R U . A 4
C9 C 0.8442(2) 0.9020(4) 0.7765(3) 0.0494(13) Uani 1 1 d . . . A 4
H9A H 0.8270 0.9560 0.7948 0.074 Uiso 1 1 calc R U . A 4
H9B H 0.8555 0.9448 0.7458 0.074 Uiso 1 1 calc R U . A 4
H9C H 0.8719 0.8687 0.8133 0.074 Uiso 1 1 calc R U . A 4
C10 C 0.77239(19) 0.7872(4) 0.8241(2) 0.0438(12) Uani 1 1 d . . . A 4
H10A H 0.7962 0.8451 0.8522 0.053 Uiso 1 1 calc R U . A 4
H10B H 0.7439 0.8314 0.7941 0.053 Uiso 1 1 calc R U . A 4
C11 C 0.7571(2) 0.7083(5) 0.8698(3) 0.0544(14) Uani 1 1 d . . . A 4
H11A H 0.7293 0.6611 0.8425 0.082 Uiso 1 1 calc R U . A 4
H11B H 0.7486 0.7571 0.9010 0.082 Uiso 1 1 calc R U . A 4
H11C H 0.7838 0.6561 0.8953 0.082 Uiso 1 1 calc R U . A 4
C12 C 0.68836(14) 0.5674(3) 0.4853(2) 0.0247(8) Uani 1 1 d . . . A 4
C13 C 0.64551(17) 0.6380(5) 0.4899(2) 0.0455(12) Uani 1 1 d . . . A 4
H13A H 0.6561 0.7179 0.5056 0.068 Uiso 1 1 calc R U . A 4
H13B H 0.6341 0.5991 0.5215 0.068 Uiso 1 1 calc R U . A 4
H13C H 0.6193 0.6415 0.4455 0.068 Uiso 1 1 calc R U . A 4
C14 C 0.67088(18) 0.4394(4) 0.4616(3) 0.0494(13) Uani 1 1 d . . . A 4
H14A H 0.6432 0.4424 0.4187 0.074 Uiso 1 1 calc R U . A 4
H14B H 0.6615 0.4006 0.4953 0.074 Uiso 1 1 calc R U . A 4
H14C H 0.6970 0.3952 0.4560 0.074 Uiso 1 1 calc R U . A 4
C15 C 0.70321(18) 0.6276(5) 0.4316(2) 0.0504(13) Uani 1 1 d . . . A 4
H15A H 0.6761 0.6254 0.3880 0.076 Uiso 1 1 calc R U . A 4
H15B H 0.7307 0.5859 0.4283 0.076 Uiso 1 1 calc R U . A 4
H15C H 0.7122 0.7094 0.4445 0.076 Uiso 1 1 calc R U . A 4
C16 C 0.86728(14) 0.4564(3) 0.61947(19) 0.0236(8) Uani 1 1 d . . . A 4
C17 C 0.86618(16) 0.4490(4) 0.5462(2) 0.0359(10) Uani 1 1 d . . . A 4
H17A H 0.8449 0.3848 0.5219 0.054 Uiso 1 1 calc R U . A 4
H17B H 0.8987 0.4342 0.5480 0.054 Uiso 1 1 calc R U . A 4
H17C H 0.8542 0.5234 0.5228 0.054 Uiso 1 1 calc R U . A 4
C18 C 0.88317(15) 0.3330(3) 0.6520(2) 0.0283(9) Uani 1 1 d . . . A 4
H18A H 0.8882 0.3363 0.6996 0.042 Uiso 1 1 calc R U . A 4
H18B H 0.9132 0.3099 0.6477 0.042 Uiso 1 1 calc R U . A 4
H18C H 0.8581 0.2752 0.6291 0.042 Uiso 1 1 calc R U . A 4
C19 C 0.90561(14) 0.5520(4) 0.6573(2) 0.0298(9) Uani 1 1 d . . . A 4
H19A H 0.8960 0.6279 0.6346 0.045 Uiso 1 1 calc R U . A 4
H19B H 0.9370 0.5293 0.6573 0.045 Uiso 1 1 calc R U . A 4
H19C H 0.9078 0.5587 0.7037 0.045 Uiso 1 1 calc R U . A 4
C20 C 0.94841(14) 0.3224(3) 1.0001(2) 0.0237(8) Uani 1 1 d . . . A 4
C21 C 0.97694(14) 0.2766(4) 1.0686(2) 0.0299(9) Uani 1 1 d . . . A 4
C22 C 1.0000 0.7558(8) 0.7500 0.0503(18) Uani 1 2 d S T P B 4
H22 H 1.0000 0.6724 0.7500 0.060 Uiso 1 2 calc R U P B 4
C23 C 0.9626(3) 0.8266(7) 0.7525(5) 0.110(3) Uani 1 1 d . . . B 4
H23 H 0.9348 0.7868 0.7520 0.132 Uiso 1 1 calc R U . B 4
C24 C 0.9616(3) 0.9543(7) 0.7556(5) 0.103(3) Uani 1 1 d . . . B 4
H24 H 0.9356 0.9936 0.7613 0.124 Uiso 1 1 calc R U . B 4
C25 C 1.0000 1.0188(10) 0.7500 0.081(3) Uani 1 2 d S T P B 4
C26 C 1.0000 1.1525(6) 0.7500 0.056(2) Uani 1 2 d S T P B 4
H26A H 1.0306 1.1812 0.7832 0.084 Uiso 0.5 1 calc R U P B 4
H26B H 0.9734 1.1812 0.7614 0.084 Uiso 0.5 1 calc R U P B 4
H26C H 0.9960 1.1812 0.7054 0.084 Uiso 0.5 1 calc R U P B 4
Cl1 Cl 0.96479(3) 0.43595(9) 0.83278(5) 0.0276(2) Uani 1 1 d . . . A 4
Cl2 Cl 0.87212(3) 0.21625(8) 0.80464(5) 0.0251(2) Uani 1 1 d . . . A 4
Cl3 Cl 0.81267(3) 0.40755(8) 0.87115(5) 0.0239(2) Uani 1 1 d . . . A 4
Cl4 Cl 0.89743(3) 0.62989(8) 0.89220(5) 0.0266(2) Uani 1 1 d . . . A 4
N1 N 0.92637(12) 0.3589(3) 0.94670(17) 0.0261(7) Uani 1 1 d . . . A 4
N2 N 0.79440(14) 0.7210(3) 0.78074(19) 0.0337(8) Uani 1 1 d . . . A 4
O1 O 0.84517(8) 0.4948(2) 0.74495(12) 0.0189(5) Uani 1 1 d . . . A 4
Zr1 Zr 0.88325(2) 0.42923(3) 0.83518(2) 0.01743(13) Uani 1 1 d . . . A 4
C27 C 1.0579(5) 1.0599(11) 0.0330(5) 0.048(3) Uani 0.5 1 d D . P C -1
H27 H 1.0900 1.0835 0.0585 0.058 Uiso 0.5 1 calc R U P C -1
C28 C 1.0331(7) 1.1097(19) -0.0300(8) 0.056(6) Uani 0.5 1 d D . P C -1
H28 H 1.0493 1.1639 -0.0475 0.067 Uiso 0.5 1 calc R U P C -1
C29 C 0.9854(6) 1.0820(13) -0.0678(7) 0.059(4) Uani 0.5 1 d D . P C -1
H29 H 0.9686 1.1179 -0.1101 0.070 Uiso 0.5 1 calc R U P C -1
C30 C 0.9628(6) 0.999(2) -0.0413(9) 0.032(4) Uani 0.5 1 d D . P C -1
H30 H 0.9302 0.9776 -0.0663 0.039 Uiso 0.5 1 calc R U P C -1
C31 C 0.9876(5) 0.9456(10) 0.0217(6) 0.047(3) Uani 0.5 1 d D . P C -1
C32 C 1.0359(7) 0.975(2) 0.0594(10) 0.038(4) Uani 0.5 1 d D . P C -1
H32 H 1.0531 0.9389 0.1015 0.045 Uiso 0.5 1 calc R U P C -1
C33 C 0.9625(9) 0.857(2) 0.0501(12) 0.069(6) Uani 0.5 1 d . . P C -1
H33A H 0.9293 0.8462 0.0182 0.103 Uiso 0.5 1 calc R U P C -1
H33B H 0.9797 0.7822 0.0577 0.103 Uiso 0.5 1 calc R U P C -1
H33C H 0.9624 0.8869 0.0927 0.103 Uiso 0.5 1 calc R U P C -1
H1N H 0.827(2) 0.686(5) 0.817(3) 0.060(16) Uiso 1 1 d . . . D 4


_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 O1 1.372(4) . ?
C1 C2 1.404(5) . ?
C1 C6 1.413(5) . ?
C2 C3 1.390(5) . ?
C2 C7 1.508(5) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 C12 1.540(5) . ?
C5 C6 1.401(5) . ?
C5 H5 0.9300 . ?
C6 C16 1.532(5) . ?
C7 N2 1.505(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.477(6) . ?
C8 C9 1.503(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.499(7) . ?
C10 N2 1.503(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.522(6) . ?
C12 C13 1.524(6) . ?
C12 C14 1.534(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.530(5) . ?
C16 C19 1.536(6) . ?
C16 C17 1.540(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.139(5) . ?
C20 C21 1.461(6) . ?
C22 C23 1.372(9) . ?
C22 C23 1.372(9) 2_756 ?
C22 H22 0.9300 . ?
C23 C24 1.427(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(9) . ?
C24 H24 0.9300 . ?
C25 C24 1.384(9) 2_756 ?
C25 C26 1.490(13) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
Cl1 Zr1 2.4265(10) . ?
Cl2 Zr1 2.4496(9) . ?
Cl3 Zr1 2.4876(9) . ?
Cl4 Zr1 2.4993(9) . ?
N1 Zr1 2.343(3) . ?
N2 H1N 1.04(6) . ?
O1 Zr1 1.946(2) . ?
C27 C28 1.368(15) . ?
C27 C32 1.381(14) . ?
C27 H27 0.9300 . ?
C28 C29 1.361(17) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(14) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(14) . ?
C30 H30 0.9300 . ?
C31 C32 1.377(16) . ?
C31 C33 1.489(19) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

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 C1 C2 117.8(3) . . ?
O1 C1 C6 122.3(3) . . ?
C2 C1 C6 119.9(3) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 C7 117.4(3) . . ?
C1 C2 C7 122.2(3) . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 116.7(3) . . ?
C3 C4 C12 122.5(3) . . ?
C5 C4 C12 120.8(3) . . ?
C4 C5 C6 124.8(3) . . ?
C4 C5 H5 117.6 . . ?
C6 C5 H5 117.6 . . ?
C5 C6 C1 116.0(3) . . ?
C5 C6 C16 120.8(3) . . ?
C1 C6 C16 123.0(3) . . ?
N2 C7 C2 115.7(3) . . ?
N2 C7 H7A 108.3 . . ?
C2 C7 H7A 108.3 . . ?
N2 C7 H7B 108.3 . . ?
C2 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N2 C8 C9 115.3(4) . . ?
N2 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
N2 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 114.3(4) . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
N2 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C13 107.7(4) . . ?
C15 C12 C14 108.9(4) . . ?
C13 C12 C14 108.6(4) . . ?
C15 C12 C4 111.2(3) . . ?
C13 C12 C4 112.3(3) . . ?
C14 C12 C4 108.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C6 111.9(3) . . ?
C18 C16 C19 110.7(3) . . ?
C6 C16 C19 108.5(3) . . ?
C18 C16 C17 106.8(3) . . ?
C6 C16 C17 112.1(3) . . ?
C19 C16 C17 106.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 179.5(5) . . ?
C23 C22 C23 109.8(9) . 2_756 ?
C23 C22 H22 125.1 . . ?
C23 C22 H22 125.1 2_756 . ?
C22 C23 C24 127.4(7) . . ?
C22 C23 H23 116.3 . . ?
C24 C23 H23 116.3 . . ?
C25 C24 C23 118.8(7) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C24 117.4(10) . 2_756 ?
C24 C25 C26 121.3(5) . . ?
C24 C25 C26 121.3(5) 2_756 . ?
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 . . ?
C20 N1 Zr1 177.5(3) . . ?
C8 N2 C10 112.4(3) . . ?
C8 N2 C7 114.3(3) . . ?
C10 N2 C7 110.2(3) . . ?
C8 N2 H1N 105(3) . . ?
C10 N2 H1N 103(3) . . ?
C7 N2 H1N 111(3) . . ?
C1 O1 Zr1 166.9(2) . . ?
O1 Zr1 N1 176.29(10) . . ?
O1 Zr1 Cl1 99.88(7) . . ?
N1 Zr1 Cl1 82.64(8) . . ?
O1 Zr1 Cl2 97.88(7) . . ?
N1 Zr1 Cl2 84.64(8) . . ?
Cl1 Zr1 Cl2 93.33(3) . . ?
O1 Zr1 Cl3 95.76(7) . . ?
N1 Zr1 Cl3 81.64(8) . . ?
Cl1 Zr1 Cl3 164.20(4) . . ?
Cl2 Zr1 Cl3 86.74(3) . . ?
O1 Zr1 Cl4 93.63(7) . . ?
N1 Zr1 Cl4 83.61(8) . . ?
Cl1 Zr1 Cl4 89.93(3) . . ?
Cl2 Zr1 Cl4 167.30(3) . . ?
Cl3 Zr1 Cl4 86.80(3) . . ?
C28 C27 C32 120.9(15) . . ?
C28 C27 H27 119.6 . . ?
C32 C27 H27 119.6 . . ?
C29 C28 C27 121.7(18) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C30 117.8(17) . . ?
C28 C29 H29 121.1 . . ?
C30 C29 H29 121.1 . . ?
C31 C30 C29 121.1(13) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C32 C31 C30 120.3(12) . . ?
C32 C31 C33 119.2(17) . . ?
C30 C31 C33 120.5(16) . . ?
C31 C32 C27 118.1(15) . . ?
C31 C32 H32 120.9 . . ?
C27 C32 H32 120.9 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -173.3(3) . . . . ?
C6 C1 C2 C3 7.5(5) . . . . ?
O1 C1 C2 C7 5.9(5) . . . . ?
C6 C1 C2 C7 -173.2(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C7 C2 C3 C4 -178.9(3) . . . . ?
C2 C3 C4 C5 -5.8(5) . . . . ?
C2 C3 C4 C12 173.9(3) . . . . ?
C3 C4 C5 C6 3.7(5) . . . . ?
C12 C4 C5 C6 -176.0(3) . . . . ?
C4 C5 C6 C1 3.7(5) . . . . ?
C4 C5 C6 C16 -172.3(3) . . . . ?
O1 C1 C6 C5 171.7(3) . . . . ?
C2 C1 C6 C5 -9.2(5) . . . . ?
O1 C1 C6 C16 -12.4(5) . . . . ?
C2 C1 C6 C16 166.7(3) . . . . ?
C3 C2 C7 N2 -115.7(4) . . . . ?
C1 C2 C7 N2 65.0(5) . . . . ?
C3 C4 C12 C15 129.4(4) . . . . ?
C5 C4 C12 C15 -50.9(5) . . . . ?
C3 C4 C12 C13 8.6(5) . . . . ?
C5 C4 C12 C13 -171.7(4) . . . . ?
C3 C4 C12 C14 -111.2(4) . . . . ?
C5 C4 C12 C14 68.6(5) . . . . ?
C5 C6 C16 C18 -116.5(4) . . . . ?
C1 C6 C16 C18 67.8(4) . . . . ?
C5 C6 C16 C19 121.2(4) . . . . ?
C1 C6 C16 C19 -54.6(4) . . . . ?
C5 C6 C16 C17 3.5(5) . . . . ?
C1 C6 C16 C17 -172.3(3) . . . . ?
C23 C22 C23 C24 -3.0(7) 2_756 . . . ?
C22 C23 C24 C25 5.9(14) . . . . ?
C23 C24 C25 C24 -2.6(6) . . . 2_756 ?
C23 C24 C25 C26 177.4(6) . . . . ?
C9 C8 N2 C10 53.3(5) . . . . ?
C9 C8 N2 C7 179.9(4) . . . . ?
C11 C10 N2 C8 -178.1(4) . . . . ?
C11 C10 N2 C7 53.1(5) . . . . ?
C2 C7 N2 C8 30.5(5) . . . . ?
C2 C7 N2 C10 158.3(3) . . . . ?
C2 C1 O1 Zr1 72.0(10) . . . . ?
C6 C1 O1 Zr1 -108.9(9) . . . . ?
C32 C27 C28 C29 3(3) . . . . ?
C27 C28 C29 C30 -2(3) . . . . ?
C28 C29 C30 C31 0(3) . . . . ?
C29 C30 C31 C32 0(4) . . . . ?
C29 C30 C31 C33 179(2) . . . . ?
C30 C31 C32 C27 1(4) . . . . ?
C33 C31 C32 C27 -178(2) . . . . ?
C28 C27 C32 C31 -3(3) . . . . ?

_refine_diff_density_max         1.242
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.094


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zr_mor
_database_code_depnum_ccdc_archive 'CCDC 1050372'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H32 Cl4 N2 O2 Zr'
_chemical_formula_weight         577.50

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'
O O 0.0106 0.0060 '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'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.5507(13)
_cell_length_b                   11.4122(6)
_cell_length_c                   10.7699(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.411(2)
_cell_angle_gamma                90
_cell_volume                     2637.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9405
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.33

_exptl_crystal_description       Square
_exptl_crystal_colour            mettalic
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.842
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17245
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.606
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_Laue_measured_fraction_full 1.00
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 1.00
_reflns_number_total             5463
_reflns_number_gt                4535
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0325P)²+8.0973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5463
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.009
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.34548(12) 0.5372(3) -0.1481(2) 0.0111(6) Uani 1 1 d . . . . .
N1 N 0.41530(13) 0.4128(3) 0.3654(3) 0.0161(6) Uani 1 1 d . . . . .
C015 C 0.45806(15) 0.3747(3) 0.4217(3) 0.0141(7) Uani 1 1 d . . . . .
C016 C 0.32632(16) 0.5171(3) -0.2840(3) 0.0165(8) Uani 1 1 d . . . . .
H01A H 0.3254 0.5912 -0.3281 0.020 Uiso 1 1 calc R U . . .
H01B H 0.2847 0.4839 -0.2940 0.020 Uiso 1 1 calc R U . . .
C017 C 0.30477(15) 0.6269(3) -0.0908(3) 0.0135(7) Uani 1 1 d . . . . .
H01C H 0.3208 0.6408 -0.0049 0.016 Uiso 1 1 calc R U . . .
H01D H 0.3064 0.7003 -0.1358 0.016 Uiso 1 1 calc R U . . .
C018 C 0.41273(15) 0.5734(3) -0.1311(3) 0.0150(7) Uani 1 1 d . . . . .
H00M H 0.4265 0.5769 -0.0428 0.018 Uiso 1 1 calc R U . . .
H00N H 0.4171 0.6510 -0.1659 0.018 Uiso 1 1 calc R U . . .
C019 C 0.45321(16) 0.4882(4) -0.1943(3) 0.0192(8) Uani 1 1 d . . . . .
H01E H 0.4962 0.5143 -0.1832 0.023 Uiso 1 1 calc R U . . .
H01F H 0.4509 0.4116 -0.1559 0.023 Uiso 1 1 calc R U . . .
C020 C 0.02896(19) 0.5597(5) -0.3302(4) 0.0399(12) Uani 1 1 d . . . . .
H02A H 0.0350 0.4768 -0.3382 0.060 Uiso 1 1 calc R U . . .
H02B H 0.0090 0.5753 -0.2559 0.060 Uiso 1 1 calc R U . . .
H02C H 0.0032 0.5881 -0.4014 0.060 Uiso 1 1 calc R U . . .
C021 C 0.1215(2) 0.5943(5) -0.4438(4) 0.0460(13) Uani 1 1 d . . . . .
H02D H 0.1274 0.5112 -0.4507 0.069 Uiso 1 1 calc R U . . .
H02E H 0.0945 0.6215 -0.5138 0.069 Uiso 1 1 calc R U . . .
H02F H 0.1611 0.6330 -0.4428 0.069 Uiso 1 1 calc R U . . .
C022 C 0.0824(3) 0.7533(5) -0.3094(6) 0.0567(16) Uani 1 1 d . . . . .
H02G H 0.1220 0.7922 -0.3043 0.085 Uiso 1 1 calc R U . . .
H02H H 0.0567 0.7816 -0.3807 0.085 Uiso 1 1 calc R U . . .
H02I H 0.0624 0.7688 -0.2351 0.085 Uiso 1 1 calc R U . . .
O2 O 0.43364(11) 0.4795(2) -0.3239(2) 0.0201(6) Uani 1 1 d . . . . .
C024 C 0.37149(16) 0.4345(3) -0.3388(3) 0.0196(8) Uani 1 1 d . . . . .
H00O H 0.3704 0.3589 -0.2979 0.024 Uiso 1 1 calc R U . . .
H00P H 0.3588 0.4233 -0.4268 0.024 Uiso 1 1 calc R U . . .
C001 C 0.51218(17) 0.3246(4) 0.4933(4) 0.0173(8) Uani 1 1 d . . . . .
H001 H 0.3423(17) 0.475(4) -0.111(4) 0.011(10) Uiso 1 1 d . . . . .
H00L H 0.503(3) 0.284(5) 0.562(5) 0.061(17) Uiso 1 1 d . . . . .
H00J H 0.529(2) 0.267(5) 0.447(5) 0.048(15) Uiso 1 1 d . . . . .
H00K H 0.537(3) 0.378(6) 0.534(6) 0.08(2) Uiso 1 1 d . . . . .
Zr1 Zr 0.32482(2) 0.45923(3) 0.23042(3) 0.01136(10) Uani 1 1 d . . . . .
Cl2 Cl 0.39057(4) 0.36086(8) 0.08110(7) 0.01463(18) Uani 1 1 d . . . . .
Cl3 Cl 0.38932(4) 0.64087(8) 0.20575(7) 0.01614(19) Uani 1 1 d . . . . .
Cl4 Cl 0.29128(4) 0.27645(8) 0.31756(8) 0.0191(2) Uani 1 1 d . . . . .
Cl5 Cl 0.27943(4) 0.56624(8) 0.39613(8) 0.0203(2) Uani 1 1 d . . . . .
O1 O 0.26039(10) 0.4833(2) 0.0967(2) 0.0139(5) Uani 1 1 d . . . . .
C002 C 0.15813(15) 0.4619(3) -0.0184(3) 0.0178(8) Uani 1 1 d . . . . .
C003 C 0.21881(15) 0.5094(3) -0.0043(3) 0.0147(7) Uani 1 1 d . . . . .
C004 C 0.23848(15) 0.5864(3) -0.0947(3) 0.0154(7) Uani 1 1 d . . . . .
C005 C 0.19682(16) 0.6216(3) -0.1951(3) 0.0181(8) Uani 1 1 d . . . . .
H005 H 0.2100 0.6748 -0.2525 0.022 Uiso 1 1 calc R U . . .
C006 C 0.17675(18) 0.2590(4) 0.0642(4) 0.0257(9) Uani 1 1 d . . . . .
H00A H 0.2194 0.2796 0.0878 0.039 Uiso 1 1 calc R U . . .
H00B H 0.1637 0.2006 0.1205 0.039 Uiso 1 1 calc R U . . .
H00C H 0.1729 0.2283 -0.0192 0.039 Uiso 1 1 calc R U . . .
C007 C 0.11926(16) 0.4994(4) -0.1226(3) 0.0206(8) Uani 1 1 d . . . . .
H007 H 0.0791 0.4689 -0.1333 0.025 Uiso 1 1 calc R U . . .
C008 C 0.13640(16) 0.5792(4) -0.2111(3) 0.0198(8) Uani 1 1 d . . . . .
C009 C 0.13675(17) 0.4165(4) 0.2041(3) 0.0226(8) Uani 1 1 d . . . . .
H00D H 0.1105 0.4845 0.2037 0.034 Uiso 1 1 calc R U . . .
H00E H 0.1216 0.3578 0.2576 0.034 Uiso 1 1 calc R U . . .
H00F H 0.1786 0.4375 0.2341 0.034 Uiso 1 1 calc R U . . .
C010 C 0.13590(16) 0.3673(4) 0.0698(3) 0.0214(8) Uani 1 1 d . . . . .
C011 C 0.09208(17) 0.6217(4) -0.3221(3) 0.0266(9) Uani 1 1 d . . . . .
C012 C 0.06839(18) 0.3287(4) 0.0311(4) 0.0317(10) Uani 1 1 d . . . . .
H01G H 0.0411 0.3950 0.0335 0.048 Uiso 1 1 calc R U . . .
H01H H 0.0656 0.2974 -0.0520 0.048 Uiso 1 1 calc R U . . .
H01I H 0.0564 0.2697 0.0877 0.048 Uiso 1 1 calc R U . . .


_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
N2 C016 1.501(4) . ?
N2 C018 1.502(4) . ?
N2 C017 1.517(4) . ?
N2 H001 0.81(4) . ?
N1 C015 1.140(4) . ?
N1 Zr1 2.380(3) . ?
C015 C001 1.454(5) . ?
C016 C024 1.514(5) . ?
C016 H01A 0.9700 . ?
C016 H01B 0.9700 . ?
C017 C004 1.498(5) . ?
C017 H01C 0.9700 . ?
C017 H01D 0.9700 . ?
C018 C019 1.510(5) . ?
C018 H00M 0.9700 . ?
C018 H00N 0.9700 . ?
C019 O2 1.423(4) . ?
C019 H01E 0.9700 . ?
C019 H01F 0.9700 . ?
C020 C011 1.528(6) . ?
C020 H02A 0.9600 . ?
C020 H02B 0.9600 . ?
C020 H02C 0.9600 . ?
C021 C011 1.541(6) . ?
C021 H02D 0.9600 . ?
C021 H02E 0.9600 . ?
C021 H02F 0.9600 . ?
C022 C011 1.524(7) . ?
C022 H02G 0.9600 . ?
C022 H02H 0.9600 . ?
C022 H02I 0.9600 . ?
O2 C024 1.429(4) . ?
C024 H00O 0.9700 . ?
C024 H00P 0.9700 . ?
C001 H00L 0.91(6) . ?
C001 H00J 0.92(6) . ?
C001 H00K 0.90(7) . ?
Zr1 O1 1.923(2) . ?
Zr1 Cl4 2.4254(9) . ?
Zr1 Cl5 2.4418(9) . ?
Zr1 Cl2 2.5068(8) . ?
Zr1 Cl3 2.5237(9) . ?
O1 C003 1.375(4) . ?
C002 C007 1.402(5) . ?
C002 C003 1.411(5) . ?
C002 C010 1.543(5) . ?
C003 C004 1.407(5) . ?
C004 C005 1.397(5) . ?
C005 C008 1.384(5) . ?
C005 H005 0.9300 . ?
C006 C010 1.523(6) . ?
C006 H00A 0.9600 . ?
C006 H00B 0.9600 . ?
C006 H00C 0.9600 . ?
C007 C008 1.394(5) . ?
C007 H007 0.9300 . ?
C008 C011 1.537(5) . ?
C009 C010 1.550(5) . ?
C009 H00D 0.9600 . ?
C009 H00E 0.9600 . ?
C009 H00F 0.9600 . ?
C010 C012 1.539(5) . ?
C012 H01G 0.9600 . ?
C012 H01H 0.9600 . ?
C012 H01I 0.9600 . ?

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
C016 N2 C018 109.5(2) . . ?
C016 N2 C017 112.6(3) . . ?
C018 N2 C017 110.7(3) . . ?
C016 N2 H001 108(3) . . ?
C018 N2 H001 108(3) . . ?
C017 N2 H001 108(3) . . ?
C015 N1 Zr1 169.8(3) . . ?
N1 C015 C001 179.2(4) . . ?
N2 C016 C024 110.3(3) . . ?
N2 C016 H01A 109.6 . . ?
C024 C016 H01A 109.6 . . ?
N2 C016 H01B 109.6 . . ?
C024 C016 H01B 109.6 . . ?
H01A C016 H01B 108.1 . . ?
C004 C017 N2 111.5(3) . . ?
C004 C017 H01C 109.3 . . ?
N2 C017 H01C 109.3 . . ?
C004 C017 H01D 109.3 . . ?
N2 C017 H01D 109.3 . . ?
H01C C017 H01D 108.0 . . ?
N2 C018 C019 111.1(3) . . ?
N2 C018 H00M 109.4 . . ?
C019 C018 H00M 109.4 . . ?
N2 C018 H00N 109.4 . . ?
C019 C018 H00N 109.4 . . ?
H00M C018 H00N 108.0 . . ?
O2 C019 C018 110.9(3) . . ?
O2 C019 H01E 109.5 . . ?
C018 C019 H01E 109.5 . . ?
O2 C019 H01F 109.5 . . ?
C018 C019 H01F 109.5 . . ?
H01E C019 H01F 108.0 . . ?
C011 C020 H02A 109.5 . . ?
C011 C020 H02B 109.5 . . ?
H02A C020 H02B 109.5 . . ?
C011 C020 H02C 109.5 . . ?
H02A C020 H02C 109.5 . . ?
H02B C020 H02C 109.5 . . ?
C011 C021 H02D 109.5 . . ?
C011 C021 H02E 109.5 . . ?
H02D C021 H02E 109.5 . . ?
C011 C021 H02F 109.5 . . ?
H02D C021 H02F 109.5 . . ?
H02E C021 H02F 109.5 . . ?
C011 C022 H02G 109.5 . . ?
C011 C022 H02H 109.5 . . ?
H02G C022 H02H 109.5 . . ?
C011 C022 H02I 109.5 . . ?
H02G C022 H02I 109.5 . . ?
H02H C022 H02I 109.5 . . ?
C019 O2 C024 108.9(2) . . ?
O2 C024 C016 111.3(3) . . ?
O2 C024 H00O 109.4 . . ?
C016 C024 H00O 109.4 . . ?
O2 C024 H00P 109.4 . . ?
C016 C024 H00P 109.4 . . ?
H00O C024 H00P 108.0 . . ?
C015 C001 H00L 113(4) . . ?
C015 C001 H00J 109(3) . . ?
H00L C001 H00J 102(5) . . ?
C015 C001 H00K 114(4) . . ?
H00L C001 H00K 97(5) . . ?
H00J C001 H00K 120(5) . . ?
O1 Zr1 N1 168.91(10) . . ?
O1 Zr1 Cl4 101.07(8) . . ?
N1 Zr1 Cl4 80.15(8) . . ?
O1 Zr1 Cl5 99.50(7) . . ?
N1 Zr1 Cl5 91.52(7) . . ?
Cl4 Zr1 Cl5 89.59(3) . . ?
O1 Zr1 Cl2 89.75(7) . . ?
N1 Zr1 Cl2 79.16(7) . . ?
Cl4 Zr1 Cl2 94.02(3) . . ?
Cl5 Zr1 Cl2 169.26(3) . . ?
O1 Zr1 Cl3 99.77(8) . . ?
N1 Zr1 Cl3 79.61(8) . . ?
Cl4 Zr1 Cl3 159.13(3) . . ?
Cl5 Zr1 Cl3 85.92(3) . . ?
Cl2 Zr1 Cl3 87.14(3) . . ?
C003 O1 Zr1 173.5(2) . . ?
C007 C002 C003 116.5(3) . . ?
C007 C002 C010 120.6(3) . . ?
C003 C002 C010 122.8(3) . . ?
O1 C003 C004 117.8(3) . . ?
O1 C003 C002 122.0(3) . . ?
C004 C003 C002 120.2(3) . . ?
C005 C004 C003 120.1(3) . . ?
C005 C004 C017 118.3(3) . . ?
C003 C004 C017 121.5(3) . . ?
C008 C005 C004 121.6(3) . . ?
C008 C005 H005 119.2 . . ?
C004 C005 H005 119.2 . . ?
C010 C006 H00A 109.5 . . ?
C010 C006 H00B 109.5 . . ?
H00A C006 H00B 109.5 . . ?
C010 C006 H00C 109.5 . . ?
H00A C006 H00C 109.5 . . ?
H00B C006 H00C 109.5 . . ?
C008 C007 C002 124.8(3) . . ?
C008 C007 H007 117.6 . . ?
C002 C007 H007 117.6 . . ?
C005 C008 C007 116.7(3) . . ?
C005 C008 C011 119.7(3) . . ?
C007 C008 C011 123.6(3) . . ?
C010 C009 H00D 109.5 . . ?
C010 C009 H00E 109.5 . . ?
H00D C009 H00E 109.5 . . ?
C010 C009 H00F 109.5 . . ?
H00D C009 H00F 109.5 . . ?
H00E C009 H00F 109.5 . . ?
C006 C010 C012 107.0(3) . . ?
C006 C010 C002 109.2(3) . . ?
C012 C010 C002 112.0(3) . . ?
C006 C010 C009 112.0(3) . . ?
C012 C010 C009 106.5(3) . . ?
C002 C010 C009 110.1(3) . . ?
C022 C011 C020 109.4(4) . . ?
C022 C011 C008 108.7(3) . . ?
C020 C011 C008 112.5(3) . . ?
C022 C011 C021 110.3(4) . . ?
C020 C011 C021 107.1(4) . . ?
C008 C011 C021 108.8(3) . . ?
C010 C012 H01G 109.5 . . ?
C010 C012 H01H 109.5 . . ?
H01G C012 H01H 109.5 . . ?
C010 C012 H01I 109.5 . . ?
H01G C012 H01I 109.5 . . ?
H01H C012 H01I 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
C018 N2 C016 C024 51.8(4) . . . . ?
C017 N2 C016 C024 175.4(3) . . . . ?
C016 N2 C017 C004 63.0(4) . . . . ?
C018 N2 C017 C004 -174.0(3) . . . . ?
C016 N2 C018 C019 -52.0(4) . . . . ?
C017 N2 C018 C019 -176.7(3) . . . . ?
N2 C018 C019 O2 58.1(4) . . . . ?
C018 C019 O2 C024 -62.5(4) . . . . ?
C019 O2 C024 C016 62.9(4) . . . . ?
N2 C016 C024 O2 -58.3(4) . . . . ?
C007 C002 C003 O1 177.2(3) . . . . ?
C010 C002 C003 O1 -6.8(5) . . . . ?
C007 C002 C003 C004 -2.6(5) . . . . ?
C010 C002 C003 C004 173.5(3) . . . . ?
O1 C003 C004 C005 -176.0(3) . . . . ?
C002 C003 C004 C005 3.8(5) . . . . ?
O1 C003 C004 C017 7.7(5) . . . . ?
C002 C003 C004 C017 -172.5(3) . . . . ?
N2 C017 C004 C005 -94.1(4) . . . . ?
N2 C017 C004 C003 82.2(4) . . . . ?
C003 C004 C005 C008 -2.4(6) . . . . ?
C017 C004 C005 C008 174.1(3) . . . . ?
C003 C002 C007 C008 -0.1(6) . . . . ?
C010 C002 C007 C008 -176.2(4) . . . . ?
C004 C005 C008 C007 -0.2(5) . . . . ?
C004 C005 C008 C011 179.2(3) . . . . ?
C002 C007 C008 C005 1.5(6) . . . . ?
C002 C007 C008 C011 -178.0(4) . . . . ?
C007 C002 C010 C006 115.7(4) . . . . ?
C003 C002 C010 C006 -60.1(4) . . . . ?
C007 C002 C010 C012 -2.6(5) . . . . ?
C003 C002 C010 C012 -178.5(3) . . . . ?
C007 C002 C010 C009 -120.9(4) . . . . ?
C003 C002 C010 C009 63.3(4) . . . . ?
C005 C008 C011 C022 -62.5(5) . . . . ?
C007 C008 C011 C022 116.9(5) . . . . ?
C005 C008 C011 C020 176.1(4) . . . . ?
C007 C008 C011 C020 -4.5(6) . . . . ?
C005 C008 C011 C021 57.6(5) . . . . ?
C007 C008 C011 C021 -122.9(4) . . . . ?

_refine_diff_density_max         1.279
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.104

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tbu_hf
_database_code_depnum_ccdc_archive 'CCDC 1050373'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        tbu_hf
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52.14 H80.16 Cl6 Hf N2 O2'
_chemical_formula_weight         1158.21

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'
O O 0.0106 0.0060 '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'
Hf Hf -0.5830 6.1852 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.6487(9)
_cell_length_b                   10.3507(4)
_cell_length_c                   14.0719(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.266(2)
_cell_angle_gamma                90
_cell_volume                     2968.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.207
_cell_measurement_theta_max      28.33

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.063
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.517
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_T_max  0.517
_exptl_absorpt_process_details   SADABS(Bruker,2014)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22537
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         0.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5234
_reflns_number_gt                4153
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0484P)²+6.6740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5234
_refine_ls_number_parameters     338
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7335(2) 0.4348(5) 0.3858(4) 0.0437(11) Uani 1 1 d . . . . .
C2 C 0.7911(2) 0.4778(5) 0.4431(4) 0.0448(12) Uani 1 1 d . . . . .
C3 C 0.8445(2) 0.4989(4) 0.3957(4) 0.0456(12) Uani 1 1 d . . . . .
H3 H 0.8835 0.5275 0.4321 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8435(3) 0.4801(5) 0.2979(4) 0.0493(13) Uani 1 1 d . . . . .
C5 C 0.7854(2) 0.4372(6) 0.2451(4) 0.0516(12) Uani 1 1 d . . . . .
H5 H 0.7831 0.4227 0.1794 0.062 Uiso 1 1 calc R U . . .
C6 C 0.7304(2) 0.4153(5) 0.2873(4) 0.0443(11) Uani 1 1 d . . . . .
C7 C 0.6688(2) 0.3621(5) 0.2295(4) 0.0527(13) Uani 1 1 d . . . . .
H7A H 0.6589 0.2797 0.2568 0.063 Uiso 1 1 calc R U . . .
H7B H 0.6765 0.3462 0.1643 0.063 Uiso 1 1 calc R U . . .
C8 C 0.5510(2) 0.3845(5) 0.1672(4) 0.0534(13) Uani 1 1 d . . . . .
H8A H 0.5445 0.3011 0.1957 0.064 Uiso 1 1 calc R U . . .
H8B H 0.5600 0.3695 0.1025 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4888(3) 0.4629(6) 0.1617(5) 0.0648(16) Uani 1 1 d . . . . .
H9A H 0.4828 0.4880 0.2253 0.097 Uiso 1 1 calc R U . . .
H9B H 0.4520 0.4118 0.1327 0.097 Uiso 1 1 calc R U . . .
H9C H 0.4920 0.5387 0.1234 0.097 Uiso 1 1 calc R U . . .
C10 C 0.6225(3) 0.5833(5) 0.1910(4) 0.0569(14) Uani 1 1 d . . . . .
H10A H 0.6597 0.6193 0.2335 0.068 Uiso 1 1 calc R U . . .
H10B H 0.5847 0.6370 0.1961 0.068 Uiso 1 1 calc R U . . .
C11 C 0.6361(4) 0.5907(9) 0.0893(5) 0.093(2) Uani 1 1 d . . . . .
H11A H 0.6770 0.5488 0.0853 0.140 Uiso 1 1 calc R U . . .
H11B H 0.6384 0.6796 0.0708 0.140 Uiso 1 1 calc R U . . .
H11C H 0.6014 0.5484 0.0469 0.140 Uiso 1 1 calc R U . . .
C12 C 0.7961(3) 0.4999(5) 0.5522(4) 0.0550(14) Uani 1 1 d . . . . .
C13 C 0.8663(3) 0.5346(9) 0.5988(5) 0.094(3) Uani 1 1 d . . . . .
H13A H 0.8952 0.4643 0.5904 0.140 Uiso 1 1 calc R U . . .
H13B H 0.8675 0.5502 0.6663 0.140 Uiso 1 1 calc R U . . .
H13C H 0.8802 0.6109 0.5689 0.140 Uiso 1 1 calc R U . . .
C14 C 0.7521(3) 0.6137(7) 0.5708(4) 0.0685(16) Uani 1 1 d . . . . .
H14A H 0.7665 0.6906 0.5424 0.103 Uiso 1 1 calc R U . . .
H14B H 0.7547 0.6262 0.6390 0.103 Uiso 1 1 calc R U . . .
H14C H 0.7075 0.5954 0.5428 0.103 Uiso 1 1 calc R U . . .
C15 C 0.7777(3) 0.3765(7) 0.6031(5) 0.082(2) Uani 1 1 d . . . . .
H15A H 0.7330 0.3537 0.5789 0.122 Uiso 1 1 calc R U . . .
H15B H 0.7825 0.3918 0.6712 0.122 Uiso 1 1 calc R U . . .
H15C H 0.8061 0.3072 0.5909 0.122 Uiso 1 1 calc R U . . .
C16 C 0.9048(3) 0.5019(6) 0.2494(5) 0.0629(16) Uani 1 1 d . . . . .
C17 C 0.9579(5) 0.5653(17) 0.3124(9) 0.195(7) Uani 1 1 d . . . . .
H17A H 0.9751 0.5080 0.3640 0.293 Uiso 1 1 calc R U . . .
H17B H 0.9417 0.6423 0.3385 0.293 Uiso 1 1 calc R U . . .
H17C H 0.9921 0.5875 0.2765 0.293 Uiso 1 1 calc R U . . .
C18 C 0.8869(5) 0.5938(17) 0.1663(9) 0.195(8) Uani 1 1 d . . . . .
H18A H 0.9262 0.6303 0.1491 0.292 Uiso 1 1 calc R U . . .
H18B H 0.8598 0.6616 0.1847 0.292 Uiso 1 1 calc R U . . .
H18C H 0.8635 0.5479 0.1122 0.292 Uiso 1 1 calc R U . . .
C19 C 0.9258(7) 0.3821(11) 0.2139(15) 0.253(11) Uani 1 1 d . . . . .
H19A H 0.9445 0.3287 0.2671 0.379 Uiso 1 1 calc R U . . .
H19B H 0.9582 0.3986 0.1735 0.379 Uiso 1 1 calc R U . . .
H19C H 0.8889 0.3388 0.1773 0.379 Uiso 1 1 calc R U . . .
Cl2 Cl 0.43450(6) 1.13198(13) 0.09387(10) 0.0516(3) Uani 1 1 d . . . . .
Cl3 Cl 0.47934(7) 0.81046(14) 0.09332(11) 0.0629(4) Uani 1 1 d . . . . .
Cl4 Cl 0.59938(6) 1.04783(17) 0.11481(10) 0.0608(4) Uani 1 1 d . . . . .
Hf1 Hf 0.5000 1.0000 0.0000 0.03868(13) Uani 1 2 d S . P . .
C20 C 0.7741(11) 0.558(2) 0.8757(12) 0.156(16) Uani 0.56(2) 1 d G . P A 1
C21 C 0.7791(10) 0.425(2) 0.8879(13) 0.111(14) Uani 0.56(2) 1 d G . P A 1
H21 H 0.7414 0.3757 0.8858 0.133 Uiso 0.56(2) 1 calc R U P A 1
C22 C 0.8404(13) 0.3666(13) 0.9032(16) 0.156(16) Uani 0.56(2) 1 d G . P A 1
H22 H 0.8437 0.2775 0.9113 0.188 Uiso 0.56(2) 1 calc R U P A 1
C23 C 0.8968(10) 0.441(2) 0.9063(16) 0.132(16) Uani 0.56(2) 1 d G . P A 1
H23 H 0.9378 0.4016 0.9165 0.158 Uiso 0.56(2) 1 calc R U P A 1
C24 C 0.8918(12) 0.574(2) 0.8941(14) 0.136(11) Uani 0.56(2) 1 d G . P A 1
H24 H 0.9295 0.6237 0.8962 0.163 Uiso 0.56(2) 1 calc R U P A 1
C25 C 0.8305(15) 0.6328(13) 0.8789(13) 0.18(2) Uani 0.56(2) 1 d G . P A 1
H25 H 0.8272 0.7218 0.8707 0.211 Uiso 0.56(2) 1 calc R U P A 1
C26 C 0.721(3) 0.601(3) 0.853(3) 0.22(3) Uani 0.56(2) 1 d . . P A 1
H26A H 0.7189 0.6505 0.7949 0.330 Uiso 0.56(2) 1 calc R U P A 1
H26B H 0.7102 0.6563 0.9034 0.330 Uiso 0.56(2) 1 calc R U P A 1
H26C H 0.6895 0.5319 0.8425 0.330 Uiso 0.56(2) 1 calc R U P A 1
C20A C 0.7070(6) 0.592(3) 0.8612(16) 0.15(2) Uani 0.45(2) 1 d G . P B 2
H20A H 0.6652 0.6280 0.8513 0.177 Uiso 0.45(2) 1 calc R U P B 2
C21A C 0.7148(12) 0.460(3) 0.8783(17) 0.16(2) Uani 0.45(2) 1 d G . P B 2
H21A H 0.6783 0.4080 0.8798 0.192 Uiso 0.45(2) 1 calc R U P B 2
C22A C 0.7772(16) 0.4060(16) 0.8931(15) 0.17(4) Uani 0.45(2) 1 d G . P B 2
H22A H 0.7825 0.3178 0.9045 0.202 Uiso 0.45(2) 1 calc R U P B 2
C23A C 0.8319(10) 0.484(2) 0.8908(12) 0.116(13) Uani 0.45(2) 1 d G . P B 2
C24A C 0.8240(7) 0.6155(19) 0.8738(14) 0.077(8) Uani 0.45(2) 1 d G . P B 2
H24A H 0.8606 0.6676 0.8723 0.092 Uiso 0.45(2) 1 calc R U P B 2
C25A C 0.7616(10) 0.6696(17) 0.8590(16) 0.121(12) Uani 0.45(2) 1 d G . P B 2
H25A H 0.7564 0.7578 0.8476 0.145 Uiso 0.45(2) 1 calc R U P B 2
C26A C 0.889(4) 0.427(5) 0.906(4) 0.24(5) Uani 0.45(2) 1 d . . P B 2
H26D H 0.8994 0.3941 0.8466 0.366 Uiso 0.45(2) 1 calc R U P B 2
H26E H 0.8878 0.3561 0.9504 0.366 Uiso 0.45(2) 1 calc R U P B 2
H26F H 0.9221 0.4873 0.9333 0.366 Uiso 0.45(2) 1 calc R U P B 2
N1 N 0.60966(19) 0.4500(4) 0.2256(3) 0.0438(9) Uani 1 1 d . . . . .
O1 O 0.67667(15) 0.4034(4) 0.4196(3) 0.0540(9) Uani 1 1 d . . . . .


_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 O1 1.374(6) . ?
C1 C6 1.392(7) . ?
C1 C2 1.397(7) . ?
C2 C3 1.396(8) . ?
C2 C12 1.540(8) . ?
C3 C4 1.386(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(8) . ?
C4 C16 1.549(8) . ?
C5 C6 1.382(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(7) . ?
C7 N1 1.517(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.510(6) . ?
C8 C9 1.511(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.501(7) . ?
C10 C11 1.503(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.535(8) . ?
C12 C13 1.535(8) . ?
C12 C15 1.542(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C19 1.430(12) . ?
C16 C17 1.451(12) . ?
C16 C18 1.507(13) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cl2 Hf1 2.4526(12) . ?
Cl3 Hf1 2.4364(14) . ?
Cl4 Hf1 2.4493(13) . ?
Hf1 Cl3 2.4364(14) 3_675 ?
Hf1 Cl4 2.4493(13) 3_675 ?
Hf1 Cl2 2.4526(12) 3_675 ?
C20 C26 1.19(5) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C20A C21A 1.3900 . ?
C20A C25A 1.3900 . ?
C20A H20A 0.9300 . ?
C21A C22A 1.3900 . ?
C21A H21A 0.9300 . ?
C22A C23A 1.3900 . ?
C22A H22A 0.9300 . ?
C23A C26A 1.31(7) . ?
C23A C24A 1.3900 . ?
C24A C25A 1.3900 . ?
C24A H24A 0.9300 . ?
C25A H25A 0.9300 . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 0.9600 . ?

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 C1 C6 113.9(4) . . ?
O1 C1 C2 124.8(5) . . ?
C6 C1 C2 121.3(4) . . ?
C3 C2 C1 116.0(5) . . ?
C3 C2 C12 121.5(5) . . ?
C1 C2 C12 122.5(5) . . ?
C4 C3 C2 124.4(5) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
C5 C4 C3 117.0(5) . . ?
C5 C4 C16 120.7(5) . . ?
C3 C4 C16 122.2(5) . . ?
C4 C5 C6 121.6(5) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 C7 120.7(5) . . ?
C1 C6 C7 119.5(4) . . ?
C6 C7 N1 114.0(4) . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 112.8(4) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 115.2(5) . . ?
N1 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 107.0(5) . . ?
C14 C12 C2 109.8(5) . . ?
C13 C12 C2 111.6(5) . . ?
C14 C12 C15 111.1(5) . . ?
C13 C12 C15 106.3(5) . . ?
C2 C12 C15 111.0(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C16 C17 111.3(10) . . ?
C19 C16 C18 109.0(11) . . ?
C17 C16 C18 104.8(10) . . ?
C19 C16 C4 110.1(6) . . ?
C17 C16 C4 112.8(6) . . ?
C18 C16 C4 108.6(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Cl3 Hf1 Cl3 180.0 . 3_675 ?
Cl3 Hf1 Cl4 90.46(6) . . ?
Cl3 Hf1 Cl4 89.54(6) 3_675 . ?
Cl3 Hf1 Cl4 89.54(6) . 3_675 ?
Cl3 Hf1 Cl4 90.46(6) 3_675 3_675 ?
Cl4 Hf1 Cl4 180.0 . 3_675 ?
Cl3 Hf1 Cl2 90.08(5) . 3_675 ?
Cl3 Hf1 Cl2 89.92(5) 3_675 3_675 ?
Cl4 Hf1 Cl2 89.52(5) . 3_675 ?
Cl4 Hf1 Cl2 90.48(5) 3_675 3_675 ?
Cl3 Hf1 Cl2 89.92(5) . . ?
Cl3 Hf1 Cl2 90.08(5) 3_675 . ?
Cl4 Hf1 Cl2 90.47(5) . . ?
Cl4 Hf1 Cl2 89.52(5) 3_675 . ?
Cl2 Hf1 Cl2 180.0 3_675 . ?
C26 C20 C21 117(3) . . ?
C26 C20 C25 123(3) . . ?
C21 C20 C25 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21A C20A C25A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C25A C20A H20A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C26A C23A C24A 123(3) . . ?
C26A C23A C22A 117(3) . . ?
C24A C23A C22A 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C24A C25A C20A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C20A C25A H25A 120.0 . . ?
C23A C26A H26D 109.5 . . ?
C23A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C23A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C10 N1 C8 113.8(4) . . ?
C10 N1 C7 112.3(4) . . ?
C8 N1 C7 108.7(4) . . ?

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 C1 C2 C3 177.1(5) . . . . ?
C6 C1 C2 C3 -0.3(7) . . . . ?
O1 C1 C2 C12 -2.5(8) . . . . ?
C6 C1 C2 C12 -179.9(5) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C12 C2 C3 C4 179.6(5) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C2 C3 C4 C16 -178.5(5) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C16 C4 C5 C6 179.0(5) . . . . ?
C4 C5 C6 C1 -1.0(8) . . . . ?
C4 C5 C6 C7 -176.8(5) . . . . ?
O1 C1 C6 C5 -176.9(5) . . . . ?
C2 C1 C6 C5 0.8(8) . . . . ?
O1 C1 C6 C7 -1.1(7) . . . . ?
C2 C1 C6 C7 176.6(5) . . . . ?
C5 C6 C7 N1 -119.8(5) . . . . ?
C1 C6 C7 N1 64.4(7) . . . . ?
C3 C2 C12 C14 113.5(6) . . . . ?
C1 C2 C12 C14 -67.0(7) . . . . ?
C3 C2 C12 C13 -4.9(8) . . . . ?
C1 C2 C12 C13 174.6(6) . . . . ?
C3 C2 C12 C15 -123.3(5) . . . . ?
C1 C2 C12 C15 56.2(7) . . . . ?
C5 C4 C16 C19 -63.8(12) . . . . ?
C3 C4 C16 C19 114.4(11) . . . . ?
C5 C4 C16 C17 171.2(10) . . . . ?
C3 C4 C16 C17 -10.6(11) . . . . ?
C5 C4 C16 C18 55.5(10) . . . . ?
C3 C4 C16 C18 -126.3(9) . . . . ?
C26 C20 C21 C22 172(3) . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C26 C20 C25 C24 -172(3) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C25A C20A C21A C22A 0.0 . . . . ?
C20A C21A C22A C23A 0.0 . . . . ?
C21A C22A C23A C26A 179(3) . . . . ?
C21A C22A C23A C24A 0.0 . . . . ?
C26A C23A C24A C25A -179(4) . . . . ?
C22A C23A C24A C25A 0.0 . . . . ?
C23A C24A C25A C20A 0.0 . . . . ?
C21A C20A C25A C24A 0.0 . . . . ?
C11 C10 N1 C8 -60.2(6) . . . . ?
C11 C10 N1 C7 63.8(6) . . . . ?
C9 C8 N1 C10 -55.9(6) . . . . ?
C9 C8 N1 C7 178.2(5) . . . . ?
C6 C7 N1 C10 54.2(6) . . . . ?
C6 C7 N1 C8 -178.9(5) . . . . ?

_refine_diff_density_max         1.403
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.161


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
