# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cm246cms
_database_code_depnum_ccdc_archive 'CCDC 1970559'
loop_
_audit_author_name
_audit_author_address
'Jeffrey L. Petersen'
;West Virginia University
United States of America
;
_audit_update_record             
;
2019-12-06 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H58 N4 Zr'
_chemical_formula_iupac          ?
_chemical_formula_weight         974.36
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   19.5532(9)
_cell_length_b                   25.1205(11)
_cell_length_c                   20.2947(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9968.5(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      3.2440
_cell_measurement_theta_max      27.5738
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'dark brown'
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4080

_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine focus sealed tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Triumph

_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scan, PHOTON 100 CMOS'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            45692
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             11009
_reflns_number_gt                9687
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0843
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_number_reflns         11009
_refine_ls_number_parameters     616
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    riding
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0063P)²+26.7593P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.414
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 4183 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(12)

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

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr Zr1 0.66342(2) 0.69902(2) 0.52235(3) 0.01577(8) Uani d . . . 1 . .
N N1 0.71101(18) 0.66156(15) 0.61153(18) 0.0230(8) Uani d . . . 1 . .
N N2 0.76715(18) 0.66249(15) 0.48962(18) 0.0217(8) Uani d . . . 1 . .
N N3 0.61066(19) 0.65779(16) 0.43788(19) 0.0251(8) Uani d . . . 1 . .
N N4 0.55840(18) 0.66853(15) 0.55931(19) 0.0235(8) Uani d . . . 1 . .
C C1 0.7017(2) 0.6562(2) 0.6776(2) 0.0240(10) Uani d . . . 1 . .
C C2 0.7362(3) 0.61198(19) 0.7007(2) 0.0301(11) Uani d . . . 1 . .
H H2 0.7368 0.5999 0.7451 0.036 Uiso calc U . R 1 . .
C C3 0.7703(2) 0.58785(19) 0.6475(2) 0.0290(11) Uani d . . . 1 . .
C C4 0.7549(2) 0.61996(17) 0.5927(2) 0.0201(9) Uani d . . . 1 . .
C C5 0.78464(19) 0.62017(16) 0.5280(3) 0.0236(9) Uani d . . . 1 . .
C C6 0.8324(2) 0.5831(2) 0.5063(2) 0.0353(14) Uani d . . . 1 . .
H H6 0.8421 0.5526 0.5323 0.042 Uiso calc U . R 1 . .
C C7 0.8654(3) 0.5904(2) 0.4476(3) 0.0454(15) Uani d . . . 1 . .
H H7 0.8973 0.5646 0.4324 0.055 Uiso calc U . R 1 . .
C C8 0.8521(3) 0.6356(2) 0.4103(3) 0.0402(13) Uani d . . . 1 . .
H H8 0.8766 0.6425 0.3708 0.048 Uiso calc U . R 1 . .
C C9 0.8025(2) 0.6700(2) 0.4323(2) 0.0291(11) Uani d . . . 1 . .
H H9 0.7923 0.7005 0.4064 0.035 Uiso calc U . R 1 . .
C C10 0.8182(3) 0.5412(2) 0.6523(3) 0.0452(14) Uani d . . . 1 . .
H H10A 0.8157 0.5259 0.6967 0.068 Uiso calc U . R 1 . .
H H10B 0.865 0.553 0.6434 0.068 Uiso calc U . R 1 . .
H H10C 0.805 0.5141 0.6199 0.068 Uiso calc U . R 1 . .
C C11 0.6632(3) 0.6954(2) 0.7196(3) 0.0300(13) Uani d . . . 1 . .
H H11A 0.6497 0.726 0.6927 0.045 Uiso calc U . R 1 . .
H H11B 0.6925 0.7074 0.7558 0.045 Uiso calc U . R 1 . .
H H11C 0.6222 0.6782 0.7376 0.045 Uiso calc U . R 1 . .
C C12 0.6203(2) 0.6501(2) 0.3719(2) 0.0276(10) Uani d . . . 1 . .
C C13 0.5711(2) 0.61673(19) 0.3474(2) 0.0285(11) Uani d . . . 1 . .
H H13 0.5679 0.605 0.3031 0.034 Uiso calc U . R 1 . .
C C14 0.5259(2) 0.6026(2) 0.3989(3) 0.0326(11) Uani d . . . 1 . .
C C15 0.5517(2) 0.62886(18) 0.4554(2) 0.0251(10) Uani d . . . 1 . .
C C16 0.52451(19) 0.63395(16) 0.5198(3) 0.0262(9) Uani d . . . 1 . .
C C17 0.4648(3) 0.6097(2) 0.5426(3) 0.0374(13) Uani d . . . 1 . .
H H17 0.4417 0.5848 0.5153 0.045 Uiso calc U . R 1 . .
C C18 0.4389(3) 0.6212(3) 0.6033(3) 0.0450(14) Uani d . . . 1 . .
H H18 0.3973 0.6053 0.6175 0.054 Uiso calc U . R 1 . .
C C19 0.4735(2) 0.6560(2) 0.6439(3) 0.0349(12) Uani d . . . 1 . .
H H19 0.4571 0.6639 0.6868 0.042 Uiso calc U . R 1 . .
C C20 0.5321(2) 0.67860(19) 0.6206(2) 0.0293(10) Uani d . . . 1 . .
H H20 0.5559 0.7027 0.6485 0.035 Uiso calc U . R 1 . .
C C21 0.4634(3) 0.5683(2) 0.3923(3) 0.0481(15) Uani d . . . 1 . .
H H21A 0.4614 0.5534 0.3478 0.072 Uiso calc U . R 1 . .
H H21B 0.4225 0.5899 0.4004 0.072 Uiso calc U . R 1 . .
H H21C 0.4655 0.5393 0.4246 0.072 Uiso calc U . R 1 . .
C C22 0.6754(3) 0.6771(3) 0.3343(3) 0.0419(15) Uani d . . . 1 . .
H H22A 0.6828 0.7129 0.3522 0.063 Uiso calc U . R 1 . .
H H22B 0.6621 0.6798 0.2878 0.063 Uiso calc U . R 1 . .
H H22C 0.7178 0.6565 0.3379 0.063 Uiso calc U . R 1 . .
C C23 0.6341(2) 0.7835(2) 0.4814(2) 0.0171(10) Uani d . . . 1 . .
C C24 0.6214(2) 0.7878(2) 0.5522(2) 0.0183(10) Uani d . . . 1 . .
C C25 0.6934(2) 0.78773(19) 0.5663(2) 0.0182(10) Uani d . . . 1 . .
C C26 0.7079(2) 0.7858(2) 0.4959(2) 0.0174(10) Uani d . . . 1 . .
C C27 0.5949(2) 0.80599(18) 0.42512(19) 0.0165(9) Uani d . . . 1 . .
C C28 0.5524(2) 0.7764(2) 0.3839(2) 0.0272(11) Uani d . . . 1 . .
H H28 0.5483 0.739 0.3898 0.033 Uiso calc U . R 1 . .
C C29 0.5158(3) 0.8018(2) 0.3340(2) 0.0304(12) Uani d . . . 1 . .
H H29 0.4871 0.7813 0.306 0.036 Uiso calc U . R 1 . .
C C30 0.5206(2) 0.8561(2) 0.3242(2) 0.0279(11) Uani d . . . 1 . .
H H30 0.4953 0.8729 0.2901 0.033 Uiso calc U . R 1 . .
C C31 0.5629(2) 0.8857(2) 0.3651(2) 0.0309(11) Uani d . . . 1 . .
H H31 0.5668 0.9231 0.3592 0.037 Uiso calc U . R 1 . .
C C32 0.5994(2) 0.86046(19) 0.4146(2) 0.0273(10) Uani d . . . 1 . .
H H32 0.6284 0.8811 0.4421 0.033 Uiso calc U . R 1 . .
C C33 0.5584(2) 0.79910(17) 0.5887(2) 0.0173(8) Uani d . . . 1 . .
C C34 0.4946(2) 0.79973(19) 0.5568(2) 0.0228(9) Uani d . . . 1 . .
H H34 0.4926 0.7919 0.5111 0.027 Uiso calc U . R 1 . .
C C35 0.4349(2) 0.8113(2) 0.5897(2) 0.0295(11) Uani d . . . 1 . .
H H35 0.3928 0.8117 0.5664 0.035 Uiso calc U . R 1 . .
C C36 0.4358(2) 0.8223(2) 0.6566(2) 0.0310(11) Uani d . . . 1 . .
H H36 0.3945 0.8303 0.6793 0.037 Uiso calc U . R 1 . .
C C37 0.4979(3) 0.8216(2) 0.6901(2) 0.0268(11) Uani d . . . 1 . .
H H37 0.499 0.8288 0.7361 0.032 Uiso calc U . R 1 . .
C C38 0.5583(2) 0.81044(19) 0.6567(2) 0.0216(10) Uani d . . . 1 . .
H H38 0.6003 0.8104 0.6801 0.026 Uiso calc U . R 1 . .
C C39 0.7341(2) 0.80544(18) 0.6241(2) 0.0186(8) Uani d . . . 1 . .
C C40 0.7212(2) 0.8561(2) 0.6487(2) 0.0269(10) Uani d . . . 1 . .
H H40 0.6862 0.8772 0.6295 0.032 Uiso calc U . R 1 . .
C C41 0.7592(3) 0.8763(2) 0.7015(2) 0.0348(12) Uani d . . . 1 . .
H H41 0.7498 0.9109 0.7179 0.042 Uiso calc U . R 1 . .
C C42 0.8100(3) 0.8461(2) 0.7297(2) 0.0366(13) Uani d . . . 1 . .
H H42 0.8357 0.8597 0.7657 0.044 Uiso calc U . R 1 . .
C C43 0.8234(3) 0.7962(2) 0.7055(3) 0.0330(15) Uani d . . . 1 . .
H H43 0.8587 0.7755 0.7249 0.04 Uiso calc U . R 1 . .
C C44 0.7861(2) 0.7754(2) 0.6530(2) 0.0259(10) Uani d . . . 1 . .
H H44 0.796 0.7407 0.637 0.031 Uiso calc U . R 1 . .
C C45 0.7692(2) 0.79291(17) 0.4557(2) 0.0187(9) Uani d . . . 1 . .
C C46 0.8347(2) 0.79007(19) 0.4824(2) 0.0254(10) Uani d . . . 1 . .
H H46 0.8401 0.7848 0.5285 0.03 Uiso calc U . R 1 . .
C C47 0.8921(2) 0.7948(2) 0.4430(2) 0.0287(11) Uani d . . . 1 . .
H H47 0.9363 0.7925 0.4622 0.034 Uiso calc U . R 1 . .
C C48 0.8855(2) 0.8028(2) 0.3757(2) 0.0282(10) Uani d . . . 1 . .
H H48 0.9251 0.8057 0.3488 0.034 Uiso calc U . R 1 . .
C C49 0.8212(3) 0.8067(2) 0.3479(3) 0.0267(12) Uani d . . . 1 . .
H H49 0.8165 0.8126 0.3019 0.032 Uiso calc U . R 1 . .
C C50 0.7632(2) 0.80193(18) 0.3874(2) 0.0195(9) Uani d . . . 1 . .
H H50 0.7191 0.8048 0.3681 0.023 Uiso calc U . R 1 . .
C C51 0.7102(4) 0.4998(3) 0.3369(3) 0.0636(19) Uani d . . . 1 . .
H H51A 0.758 0.499 0.3226 0.095 Uiso calc U . R 1 . .
H H51B 0.6908 0.5351 0.328 0.095 Uiso calc U . R 1 . .
H H51C 0.6842 0.4728 0.3128 0.095 Uiso calc U . R 1 . .
C C52 0.7064(3) 0.4885(2) 0.4096(3) 0.0389(13) Uani d . . . 1 . .
C C53 0.6747(3) 0.5235(2) 0.4519(3) 0.0369(12) Uani d . . . 1 . .
H H53 0.6562 0.5556 0.4348 0.044 Uiso calc U . R 1 . .
C C54 0.6691(3) 0.5134(2) 0.5183(5) 0.0460(13) Uani d . . . 1 . .
H H54 0.646 0.5376 0.5466 0.055 Uiso calc U . R 1 . .
C C55 0.6980(3) 0.4668(3) 0.5430(3) 0.0521(17) Uani d . . . 1 . .
H H55 0.6961 0.4594 0.5889 0.063 Uiso calc U . R 1 . .
C C56 0.7293(3) 0.4316(2) 0.5011(3) 0.0565(19) Uani d . . . 1 . .
H H56 0.7487 0.3997 0.518 0.068 Uiso calc U . R 1 . .
C C57 0.7330(3) 0.4420(2) 0.4356(3) 0.0504(15) Uani d . . . 1 . .
H H57 0.7541 0.4169 0.4071 0.061 Uiso calc U . R 1 . .
C C58 0.9917(9) 0.4909(5) 0.6414(4) 0.043(5) Uani d . P G 0.5 A -1
C C59 0.9776(7) 0.4537(4) 0.5925(4) 0.035(4) Uani d . P G 0.5 A -1
H H59 0.9593 0.4199 0.6039 0.042 Uiso calc U P R 0.5 A -1
C C60 0.9905(8) 0.4660(3) 0.5268(4) 0.036(3) Uani d . P G 0.5 A -1
H H60 0.9809 0.4406 0.4934 0.043 Uiso calc U P R 0.5 A -1
C C61 1.0174(9) 0.5154(3) 0.5101(4) 0.047(4) Uani d . P G 0.5 A -1
H H61 1.0261 0.5238 0.4653 0.056 Uiso calc U P R 0.5 A -1
C C62 1.0314(6) 0.5525(3) 0.5591(5) 0.058(5) Uani d . P G 0.5 A -1
H H62 1.0498 0.5863 0.5476 0.069 Uiso calc U P R 0.5 A -1
C C63 1.0185(7) 0.5403(4) 0.6247(5) 0.055(5) Uani d . P G 0.5 A -1
H H63 1.0281 0.5657 0.6581 0.066 Uiso calc U P R 0.5 A -1
C C64 0.9763(8) 0.4773(6) 0.7118(6) 0.075(5) Uani d . P . 0.5 A -1
H H64A 0.9438 0.4476 0.7133 0.113 Uiso calc U P R 0.5 A -1
H H64B 0.9565 0.5084 0.7338 0.113 Uiso calc U P R 0.5 A -1
H H64C 1.0187 0.467 0.7342 0.113 Uiso calc U P R 0.5 A -1


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 N1 . 2.242(4) ?
Zr1 N3 . 2.253(4) ?
Zr1 N4 . 2.316(4) ?
Zr1 N2 . 2.323(4) ?
Zr1 C23 . 2.350(5) ?
Zr1 C26 . 2.407(5) ?
Zr1 C24 . 2.452(5) ?
Zr1 C25 . 2.471(5) ?
N1 C1 . 1.360(6) ?
N1 C4 . 1.406(6) ?
N2 C5 . 1.362(6) ?
N2 C9 . 1.366(6) ?
N3 C12 . 1.366(6) ?
N3 C15 . 1.408(6) ?
N4 C16 . 1.356(6) ?
N4 C20 . 1.371(6) ?
C1 C2 . 1.382(7) ?
C1 C11 . 1.504(7) ?
C2 C3 . 1.407(7) ?
C3 C4 . 1.407(6) ?
C3 C10 . 1.503(7) ?
C4 C5 . 1.435(7) ?
C5 C6 . 1.391(6) ?
C6 C7 . 1.367(7) ?
C7 C8 . 1.389(8) ?
C8 C9 . 1.374(7) ?
C12 C13 . 1.370(7) ?
C12 C22 . 1.485(7) ?
C13 C14 . 1.413(7) ?
C14 C15 . 1.416(7) ?
C14 C21 . 1.501(7) ?
C15 C16 . 1.417(8) ?
C16 C17 . 1.396(6) ?
C17 C18 . 1.362(7) ?
C18 C19 . 1.380(8) ?
C19 C20 . 1.362(7) ?
C23 C24 . 1.462(6) ?
C23 C26 . 1.473(6) ?
C23 C27 . 1.487(6) ?
C24 C25 . 1.438(7) ?
C24 C33 . 1.465(6) ?
C25 C26 . 1.457(6) ?
C25 C39 . 1.487(6) ?
C26 C45 . 1.461(6) ?
C27 C32 . 1.388(6) ?
C27 C28 . 1.394(6) ?
C28 C29 . 1.394(7) ?
C29 C30 . 1.382(7) ?
C30 C31 . 1.387(7) ?
C31 C32 . 1.385(7) ?
C33 C34 . 1.405(6) ?
C33 C38 . 1.408(6) ?
C34 C35 . 1.374(6) ?
C35 C36 . 1.386(7) ?
C36 C37 . 1.391(7) ?
C37 C38 . 1.391(6) ?
C39 C40 . 1.390(6) ?
C39 C44 . 1.395(6) ?
C40 C41 . 1.397(7) ?
C41 C42 . 1.375(8) ?
C42 C43 . 1.371(8) ?
C43 C44 . 1.392(7) ?
C45 C46 . 1.392(6) ?
C45 C50 . 1.409(6) ?
C46 C47 . 1.383(6) ?
C47 C48 . 1.387(7) ?
C48 C49 . 1.381(8) ?
C49 C50 . 1.394(7) ?
C51 C52 . 1.505(8) ?
C52 C53 . 1.377(7) ?
C52 C57 . 1.383(8) ?
C53 C54 . 1.374(10) ?
C54 C55 . 1.394(8) ?
C55 C56 . 1.371(9) ?
C56 C57 . 1.356(9) ?
C58 C59 . 1.39 ?
C58 C63 . 1.39 ?
C58 C64 . 1.498(14) ?
C59 C60 . 1.39 ?
C60 C61 . 1.39 ?
C61 C62 . 1.39 ?
C62 C63 . 1.39 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Zr1 N3 . . 127.69(13) ?
N1 Zr1 N4 . . 88.15(13) ?
N3 Zr1 N4 . . 71.85(14) ?
N1 Zr1 N2 . . 72.70(13) ?
N3 Zr1 N2 . . 90.04(13) ?
N4 Zr1 N2 . . 137.38(12) ?
N1 Zr1 C23 . . 139.98(15) ?
N3 Zr1 C23 . . 91.96(15) ?
N4 Zr1 C23 . . 101.37(14) ?
N2 Zr1 C23 . . 117.92(15) ?
N1 Zr1 C26 . . 114.22(14) ?
N3 Zr1 C26 . . 114.32(15) ?
N4 Zr1 C26 . . 133.76(14) ?
N2 Zr1 C26 . . 88.78(14) ?
C23 Zr1 C26 . . 36.04(16) ?
N1 Zr1 C24 . . 108.76(15) ?
N3 Zr1 C24 . . 116.88(14) ?
N4 Zr1 C24 . . 85.60(15) ?
N2 Zr1 C24 . . 136.26(15) ?
C23 Zr1 C24 . . 35.38(14) ?
C26 Zr1 C24 . . 49.67(13) ?
N1 Zr1 C25 . . 89.36(15) ?
N3 Zr1 C25 . . 142.92(15) ?
N4 Zr1 C25 . . 113.07(14) ?
N2 Zr1 C25 . . 104.60(14) ?
C23 Zr1 C25 . . 51.03(13) ?
C26 Zr1 C25 . . 34.72(15) ?
C24 Zr1 C25 . . 33.96(16) ?
C1 N1 C4 . . 106.0(4) ?
C1 N1 Zr1 . . 141.5(3) ?
C4 N1 Zr1 . . 110.2(3) ?
C5 N2 C9 . . 117.9(4) ?
C5 N2 Zr1 . . 111.3(3) ?
C9 N2 Zr1 . . 129.1(3) ?
C12 N3 C15 . . 106.7(4) ?
C12 N3 Zr1 . . 138.4(3) ?
C15 N3 Zr1 . . 114.9(3) ?
C16 N4 C20 . . 118.2(4) ?
C16 N4 Zr1 . . 117.0(3) ?
C20 N4 Zr1 . . 124.5(3) ?
N1 C1 C2 . . 110.5(4) ?
N1 C1 C11 . . 124.1(5) ?
C2 C1 C11 . . 125.3(4) ?
C1 C2 C3 . . 108.5(4) ?
C2 C3 C4 . . 105.0(4) ?
C2 C3 C10 . . 125.6(4) ?
C4 C3 C10 . . 129.1(5) ?
N1 C4 C3 . . 110.0(4) ?
N1 C4 C5 . . 119.6(4) ?
C3 C4 C5 . . 129.7(4) ?
N2 C5 C6 . . 120.7(5) ?
N2 C5 C4 . . 115.1(4) ?
C6 C5 C4 . . 124.0(4) ?
C7 C6 C5 . . 120.2(5) ?
C6 C7 C8 . . 119.7(5) ?
C9 C8 C7 . . 118.1(5) ?
N2 C9 C8 . . 123.1(5) ?
N3 C12 C13 . . 110.2(4) ?
N3 C12 C22 . . 122.7(5) ?
C13 C12 C22 . . 127.1(5) ?
C12 C13 C14 . . 109.0(4) ?
C13 C14 C15 . . 105.0(4) ?
C13 C14 C21 . . 126.0(5) ?
C15 C14 C21 . . 129.0(5) ?
N3 C15 C14 . . 109.1(4) ?
N3 C15 C16 . . 119.5(4) ?
C14 C15 C16 . . 131.0(4) ?
N4 C16 C17 . . 119.5(5) ?
N4 C16 C15 . . 114.9(4) ?
C17 C16 C15 . . 125.5(5) ?
C18 C17 C16 . . 121.3(5) ?
C17 C18 C19 . . 119.4(5) ?
C20 C19 C18 . . 118.1(5) ?
C19 C20 N4 . . 123.6(5) ?
C24 C23 C26 . . 88.1(4) ?
C24 C23 C27 . . 129.7(4) ?
C26 C23 C27 . . 130.1(4) ?
C24 C23 Zr1 . . 76.1(3) ?
C26 C23 Zr1 . . 74.1(3) ?
C27 C23 Zr1 . . 137.8(3) ?
C25 C24 C23 . . 91.6(4) ?
C25 C24 C33 . . 136.3(4) ?
C23 C24 C33 . . 130.9(4) ?
C25 C24 Zr1 . . 73.7(3) ?
C23 C24 Zr1 . . 68.5(3) ?
C33 C24 Zr1 . . 125.7(3) ?
C24 C25 C26 . . 89.7(4) ?
C24 C25 C39 . . 133.0(4) ?
C26 C25 C39 . . 132.9(4) ?
C24 C25 Zr1 . . 72.3(3) ?
C26 C25 Zr1 . . 70.3(3) ?
C39 C25 Zr1 . . 133.0(3) ?
C25 C26 C45 . . 134.6(4) ?
C25 C26 C23 . . 90.4(4) ?
C45 C26 C23 . . 134.2(4) ?
C25 C26 Zr1 . . 75.0(3) ?
C45 C26 Zr1 . . 122.1(3) ?
C23 C26 Zr1 . . 69.8(3) ?
C32 C27 C28 . . 118.1(4) ?
C32 C27 C23 . . 117.4(4) ?
C28 C27 C23 . . 124.5(4) ?
C27 C28 C29 . . 119.9(5) ?
C30 C29 C28 . . 121.4(5) ?
C29 C30 C31 . . 118.9(4) ?
C32 C31 C30 . . 119.7(5) ?
C31 C32 C27 . . 122.0(4) ?
C34 C33 C38 . . 116.5(4) ?
C34 C33 C24 . . 121.0(4) ?
C38 C33 C24 . . 122.4(4) ?
C35 C34 C33 . . 122.2(4) ?
C34 C35 C36 . . 120.5(4) ?
C35 C36 C37 . . 119.1(4) ?
C38 C37 C36 . . 120.3(4) ?
C37 C38 C33 . . 121.3(4) ?
C40 C39 C44 . . 118.5(4) ?
C40 C39 C25 . . 117.4(4) ?
C44 C39 C25 . . 124.1(4) ?
C39 C40 C41 . . 120.7(5) ?
C42 C41 C40 . . 120.2(5) ?
C43 C42 C41 . . 119.5(5) ?
C42 C43 C44 . . 121.2(6) ?
C43 C44 C39 . . 120.0(5) ?
C46 C45 C50 . . 117.9(4) ?
C46 C45 C26 . . 122.1(4) ?
C50 C45 C26 . . 120.0(4) ?
C47 C46 C45 . . 121.1(4) ?
C46 C47 C48 . . 120.5(4) ?
C49 C48 C47 . . 119.8(4) ?
C48 C49 C50 . . 120.0(5) ?
C49 C50 C45 . . 120.8(4) ?
C53 C52 C57 . . 118.1(5) ?
C53 C52 C51 . . 120.9(5) ?
C57 C52 C51 . . 121.0(6) ?
C54 C53 C52 . . 121.9(5) ?
C53 C54 C55 . . 118.4(6) ?
C56 C55 C54 . . 119.9(6) ?
C57 C56 C55 . . 120.5(6) ?
C56 C57 C52 . . 121.0(6) ?
C59 C58 C63 . . 120.0 ?
C59 C58 C64 . . 119.2(8) ?
C63 C58 C64 . . 120.7(8) ?
C58 C59 C60 . . 120.0 ?
C59 C60 C61 . . 120.0 ?
C62 C61 C60 . . 120.0 ?
C63 C62 C61 . . 120.0 ?
C62 C63 C58 . . 120.0 ?




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene, pentane'
_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_cm255cms
_database_code_depnum_ccdc_archive 'CCDC 1970560'
loop_
_audit_author_name
_audit_author_address
'Jeffrey L. Petersen'
;West Virginia University
United States of America
;
_audit_update_record             
;
2019-12-06 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Br2 N4 Zr'
_chemical_formula_iupac          ?
_chemical_formula_weight         593.47

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.8984(5)
_cell_length_b                   15.1436(9)
_cell_length_c                   16.4410(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.628(2)
_cell_angle_gamma                90
_cell_volume                     2204.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9755
_cell_measurement_theta_min      2.8441
_cell_measurement_theta_max      32.5561
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'intense red'
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.116
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168

_exptl_absorpt_coefficient_mu    4.139
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.65

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine focus sealed tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Triumph

_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scan, PHOTON 100 CMOS'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            41553
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             6431
_reflns_number_gt                5370
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1187
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_number_reflns         6431
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+24.8220P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.582
_refine_diff_density_min         -1.542
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr Zr1 0.30354(5) 0.63621(3) 0.28661(3) 0.00974(9) Uani d . . . 1 . .
Br Br1 0.09686(5) 0.53621(3) 0.21836(3) 0.01807(11) Uani d . . . 1 . .
Br Br2 0.42208(7) 0.53238(3) 0.39593(3) 0.02618(13) Uani d . . . 1 . .
N N1 0.4641(4) 0.6321(2) 0.1950(2) 0.0118(7) Uani d . . . 1 . .
N N2 0.2325(4) 0.7453(2) 0.1926(2) 0.0128(7) Uani d . . . 1 . .
N N3 0.1802(4) 0.7138(2) 0.3688(2) 0.0129(7) Uani d . . . 1 . .
N N4 0.4589(4) 0.7518(2) 0.3348(2) 0.0127(7) Uani d . . . 1 . .
C C1 0.6012(5) 0.5900(3) 0.1905(3) 0.0154(9) Uani d . . . 1 . .
C C2 0.6840(5) 0.6367(3) 0.1382(3) 0.0169(9) Uani d . . . 1 . .
H H2 0.7817 0.6211 0.1243 0.02 Uiso calc U . R 1 . .
C C3 0.6005(5) 0.7113(3) 0.1085(3) 0.0147(9) Uani d . . . 1 . .
C C4 0.4637(5) 0.7061(3) 0.1429(3) 0.0122(8) Uani d . . . 1 . .
C C5 0.3341(5) 0.7623(3) 0.1374(3) 0.0107(8) Uani d . . . 1 . .
C C6 0.3071(5) 0.8315(3) 0.0807(3) 0.0131(8) Uani d . . . 1 . .
H H6 0.3773 0.8437 0.0422 0.016 Uiso calc U . R 1 . .
C C7 0.1787(6) 0.8813(3) 0.0815(3) 0.0180(9) Uani d . . . 1 . .
H H7 0.1602 0.9284 0.0437 0.022 Uiso calc U . R 1 . .
C C8 0.0753(5) 0.8631(3) 0.1373(3) 0.0178(9) Uani d . . . 1 . .
H H8 -0.0146 0.8969 0.1378 0.021 Uiso calc U . R 1 . .
C C9 0.1065(5) 0.7948(3) 0.1919(3) 0.0150(9) Uani d . . . 1 . .
H H9 0.0366 0.7822 0.2305 0.018 Uiso calc U . R 1 . .
C C10 0.6540(6) 0.7812(3) 0.0545(3) 0.0193(10) Uani d . . . 1 . .
H H10A 0.7636 0.7764 0.0536 0.029 Uiso calc U . R 1 . .
H H10B 0.6288 0.8394 0.0754 0.029 Uiso calc U . R 1 . .
H H10C 0.6046 0.7738 -0.001 0.029 Uiso calc U . R 1 . .
C C11 0.6488(5) 0.5091(3) 0.2383(3) 0.0184(9) Uani d . . . 1 . .
H H11A 0.6834 0.5257 0.2946 0.028 Uiso calc U . R 1 . .
H H11B 0.7313 0.48 0.2132 0.028 Uiso calc U . R 1 . .
H H11C 0.563 0.4685 0.2382 0.028 Uiso calc U . R 1 . .
C C12 0.0407(5) 0.7083(3) 0.3980(3) 0.0140(8) Uani d . . . 1 . .
C C13 0.0195(6) 0.7806(3) 0.4473(3) 0.0167(9) Uani d . . . 1 . .
H H13 -0.0677 0.7921 0.4746 0.02 Uiso calc U . R 1 . .
C C14 0.1494(6) 0.8341(3) 0.4499(3) 0.0167(9) Uani d . . . 1 . .
C C15 0.2469(5) 0.7915(3) 0.4019(3) 0.0125(8) Uani d . . . 1 . .
C C16 0.3983(5) 0.8111(3) 0.3851(3) 0.0126(8) Uani d . . . 1 . .
C C17 0.4836(6) 0.8828(3) 0.4168(3) 0.0200(10) Uani d . . . 1 . .
H H17 0.4422 0.9228 0.4532 0.024 Uiso calc U . R 1 . .
C C18 0.6270(6) 0.8955(3) 0.3954(3) 0.0224(10) Uani d . . . 1 . .
H H18 0.6851 0.9444 0.4168 0.027 Uiso calc U . R 1 . .
C C19 0.6872(5) 0.8369(3) 0.3425(3) 0.0195(10) Uani d . . . 1 . .
H H19 0.7853 0.8457 0.3258 0.023 Uiso calc U . R 1 . .
C C20 0.6003(5) 0.7654(3) 0.3147(3) 0.0156(9) Uani d . . . 1 . .
H H20 0.6422 0.7239 0.28 0.019 Uiso calc U . R 1 . .
C C21 0.1733(6) 0.9175(3) 0.4987(3) 0.0209(10) Uani d . . . 1 . .
H H21A 0.2577 0.9094 0.541 0.031 Uiso calc U . R 1 . .
H H21B 0.0815 0.9315 0.5246 0.031 Uiso calc U . R 1 . .
H H21C 0.1963 0.966 0.4625 0.031 Uiso calc U . R 1 . .
C C22 -0.0659(6) 0.6337(4) 0.3806(3) 0.0216(10) Uani d . . . 1 . .
H H22A -0.1014 0.6332 0.3222 0.032 Uiso calc U . R 1 . .
H H22B -0.1523 0.6408 0.4127 0.032 Uiso calc U . R 1 . .
H H22C -0.0144 0.578 0.3954 0.032 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 N3 . 2.168(4) ?
Zr1 N1 . 2.177(4) ?
Zr1 N2 . 2.307(4) ?
Zr1 N4 . 2.321(4) ?
Zr1 Br2 . 2.5384(7) ?
Zr1 Br1 . 2.5554(6) ?
N1 C1 . 1.384(6) ?
N1 C4 . 1.411(6) ?
N2 C9 . 1.348(6) ?
N2 C5 . 1.368(6) ?
N3 C12 . 1.377(6) ?
N3 C15 . 1.404(5) ?
N4 C20 . 1.347(6) ?
N4 C16 . 1.368(6) ?
C1 C2 . 1.381(7) ?
C1 C11 . 1.495(7) ?
C2 C3 . 1.412(7) ?
C3 C4 . 1.394(6) ?
C3 C10 . 1.489(7) ?
C4 C5 . 1.429(6) ?
C5 C6 . 1.408(6) ?
C6 C7 . 1.370(7) ?
C7 C8 . 1.389(7) ?
C8 C9 . 1.381(7) ?
C12 C13 . 1.385(6) ?
C12 C22 . 1.485(7) ?
C13 C14 . 1.408(7) ?
C14 C15 . 1.388(6) ?
C14 C21 . 1.501(6) ?
C15 C16 . 1.432(6) ?
C16 C17 . 1.397(6) ?
C17 C18 . 1.370(8) ?
C18 C19 . 1.387(7) ?
C19 C20 . 1.382(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Zr1 N1 . . 148.62(14) ?
N3 Zr1 N2 . . 84.69(14) ?
N1 Zr1 N2 . . 73.28(13) ?
N3 Zr1 N4 . . 72.53(14) ?
N1 Zr1 N4 . . 81.27(14) ?
N2 Zr1 N4 . . 78.66(13) ?
N3 Zr1 Br2 . . 95.44(10) ?
N1 Zr1 Br2 . . 102.52(10) ?
N2 Zr1 Br2 . . 170.10(10) ?
N4 Zr1 Br2 . . 91.91(10) ?
N3 Zr1 Br1 . . 102.03(10) ?
N1 Zr1 Br1 . . 99.91(10) ?
N2 Zr1 Br1 . . 89.56(10) ?
N4 Zr1 Br1 . . 167.33(10) ?
Br2 Zr1 Br1 . . 100.08(2) ?
C1 N1 C4 . . 106.4(4) ?
C1 N1 Zr1 . . 133.8(3) ?
C4 N1 Zr1 . . 115.8(3) ?
C9 N2 C5 . . 119.5(4) ?
C9 N2 Zr1 . . 125.2(3) ?
C5 N2 Zr1 . . 115.1(3) ?
C12 N3 C15 . . 106.0(4) ?
C12 N3 Zr1 . . 135.5(3) ?
C15 N3 Zr1 . . 118.4(3) ?
C20 N4 C16 . . 118.8(4) ?
C20 N4 Zr1 . . 124.8(3) ?
C16 N4 Zr1 . . 116.4(3) ?
C2 C1 N1 . . 109.0(4) ?
C2 C1 C11 . . 127.3(4) ?
N1 C1 C11 . . 123.7(4) ?
C1 C2 C3 . . 109.2(4) ?
C4 C3 C2 . . 105.4(4) ?
C4 C3 C10 . . 128.6(4) ?
C2 C3 C10 . . 125.9(4) ?
C3 C4 N1 . . 109.9(4) ?
C3 C4 C5 . . 132.3(4) ?
N1 C4 C5 . . 117.8(4) ?
N2 C5 C6 . . 119.9(4) ?
N2 C5 C4 . . 115.3(4) ?
C6 C5 C4 . . 124.7(4) ?
C7 C6 C5 . . 119.5(4) ?
C6 C7 C8 . . 120.3(4) ?
C9 C8 C7 . . 118.3(4) ?
N2 C9 C8 . . 122.5(4) ?
N3 C12 C13 . . 109.6(4) ?
N3 C12 C22 . . 124.0(4) ?
C13 C12 C22 . . 126.3(4) ?
C12 C13 C14 . . 108.3(4) ?
C15 C14 C13 . . 105.8(4) ?
C15 C14 C21 . . 129.2(5) ?
C13 C14 C21 . . 125.0(4) ?
C14 C15 N3 . . 110.2(4) ?
C14 C15 C16 . . 131.8(4) ?
N3 C15 C16 . . 117.9(4) ?
N4 C16 C17 . . 120.3(4) ?
N4 C16 C15 . . 114.6(4) ?
C17 C16 C15 . . 125.1(4) ?
C18 C17 C16 . . 119.9(5) ?
C17 C18 C19 . . 119.9(5) ?
C20 C19 C18 . . 118.1(5) ?
N4 C20 C19 . . 123.0(5) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene, pentane'
_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_cm195cms
_database_code_depnum_ccdc_archive 'CCDC 1970561'
loop_
_audit_author_name
_audit_author_address
'Jeffrey L. Petersen'
;West Virginia University
United States of America
;
_audit_update_record             
;
2019-12-06 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 N4 Zr'
_chemical_formula_iupac          ?
_chemical_formula_weight         615.91

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   32.4207(13)
_cell_length_b                   11.5918(5)
_cell_length_c                   16.0701(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.6983(11)
_cell_angle_gamma                90
_cell_volume                     5841.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      3.0849
_cell_measurement_theta_max      32.5708
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       irregular
_exptl_crystal_colour            'intense orange'
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2560

_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Triumph

_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scan, PHOTON 100 CMOS'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            34862
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         32.62
_diffrn_reflns_theta_full        32.62
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             10660
_reflns_number_gt                8655
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0970
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_number_reflns         10660
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    riding
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+14.7152P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.106
_refine_diff_density_min         -0.772
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr Zr1 0.14287(2) 0.29842(2) 0.57260(2) 0.01407(4) Uani d . . . 1 . .
N N1 0.09674(5) 0.21662(14) 0.63495(10) 0.0193(3) Uani d . . . 1 . .
N N2 0.12877(5) 0.10712(14) 0.52070(10) 0.0196(3) Uani d . . . 1 . .
N N3 0.08846(5) 0.38399(14) 0.48245(10) 0.0191(3) Uani d . . . 1 . .
N N4 0.13621(5) 0.48948(13) 0.61992(9) 0.0162(3) Uani d . . . 1 . .
C C1 0.07962(6) 0.24742(18) 0.70119(12) 0.0216(3) Uani d . . . 1 . .
C C2 0.05251(6) 0.15929(19) 0.71513(13) 0.0245(4) Uani d . . . 1 . .
H H2 0.0371 0.159 0.7582 0.029 Uiso calc U . R 1 . .
C C3 0.05195(6) 0.07261(18) 0.65534(14) 0.0248(4) Uani d . . . 1 . .
C C4 0.07986(5) 0.10829(16) 0.60618(12) 0.0194(3) Uani d . . . 1 . .
C C5 0.09681(6) 0.05049(16) 0.54437(12) 0.0199(3) Uani d . . . 1 . .
C C6 0.08331(6) -0.05799(17) 0.50919(14) 0.0266(4) Uani d . . . 1 . .
H H6 0.0595 -0.0942 0.5225 0.032 Uiso calc U . R 1 . .
C C7 0.10400(8) -0.1123(2) 0.45601(16) 0.0332(5) Uani d . . . 1 . .
H H7 0.095 -0.1863 0.4329 0.04 Uiso calc U . R 1 . .
C C8 0.13850(7) -0.05721(19) 0.43630(14) 0.0299(4) Uani d . . . 1 . .
H H8 0.1541 -0.0939 0.4011 0.036 Uiso calc U . R 1 . .
C C9 0.14936(7) 0.05042(18) 0.46847(13) 0.0250(4) Uani d . . . 1 . .
H H9 0.1725 0.0882 0.4538 0.03 Uiso calc U . R 1 . .
C C10 0.02567(8) -0.0363(2) 0.64651(18) 0.0377(5) Uani d . . . 1 . .
H H10A 0.0445 -0.1026 0.6648 0.057 Uiso calc U . R 1 . .
H H10B 0.0098 -0.0463 0.5863 0.057 Uiso calc U . R 1 . .
H H10C 0.0056 -0.0306 0.6827 0.057 Uiso calc U . R 1 . .
C C11 0.08824(7) 0.3596(2) 0.74663(13) 0.0275(4) Uani d . . . 1 . .
H H11A 0.1191 0.3718 0.7662 0.041 Uiso calc U . R 1 . .
H H11B 0.0759 0.3593 0.7964 0.041 Uiso calc U . R 1 . .
H H11C 0.0754 0.422 0.7074 0.041 Uiso calc U . R 1 . .
C C12 0.06077(6) 0.35232(18) 0.40607(12) 0.0236(4) Uani d . . . 1 . .
C C13 0.03088(7) 0.4388(2) 0.37899(13) 0.0298(5) Uani d . . . 1 . .
H H13 0.0083 0.4373 0.3281 0.036 Uiso calc U . R 1 . .
C C14 0.03953(6) 0.52914(18) 0.43942(13) 0.0255(4) Uani d . . . 1 . .
C C15 0.07514(6) 0.49242(16) 0.50278(12) 0.0191(3) Uani d . . . 1 . .
C C16 0.10014(6) 0.54699(16) 0.57852(12) 0.0184(3) Uani d . . . 1 . .
C C17 0.08944(6) 0.65259(18) 0.61025(14) 0.0256(4) Uani d . . . 1 . .
H H17 0.0633 0.6894 0.5833 0.031 Uiso calc U . R 1 . .
C C18 0.11682(7) 0.70269(19) 0.68034(14) 0.0284(4) Uani d . . . 1 . .
H H18 0.1098 0.7742 0.7021 0.034 Uiso calc U . R 1 . .
C C19 0.15490(6) 0.64776(17) 0.71897(12) 0.0228(4) Uani d . . . 1 . .
H H19 0.1748 0.6823 0.766 0.027 Uiso calc U . R 1 . .
C C20 0.16311(6) 0.54203(16) 0.68755(12) 0.0196(3) Uani d . . . 1 . .
H H20 0.189 0.504 0.7147 0.024 Uiso calc U . R 1 . .
C C21 0.01484(7) 0.6396(2) 0.43259(17) 0.0361(5) Uani d . . . 1 . .
H H21A -0.0007 0.6419 0.4776 0.054 Uiso calc U . R 1 . .
H H21B -0.0055 0.644 0.376 0.054 Uiso calc U . R 1 . .
H H21C 0.0345 0.7051 0.4397 0.054 Uiso calc U . R 1 . .
C C22 0.06395(7) 0.2403(2) 0.36194(14) 0.0314(5) Uani d . . . 1 . .
H H22A 0.093 0.2307 0.3554 0.047 Uiso calc U . R 1 . .
H H22B 0.0438 0.2402 0.3051 0.047 Uiso calc U . R 1 . .
H H22C 0.0572 0.1767 0.3964 0.047 Uiso calc U . R 1 . .
C C23 0.19517(6) 0.29041(16) 0.70006(11) 0.0188(3) Uani d . . . 1 . .
H H23A 0.2211 0.3344 0.6979 0.023 Uiso calc U . R 1 . .
H H23B 0.1848 0.315 0.7502 0.023 Uiso calc U . R 1 . .
C C24 0.20123(5) 0.16478(16) 0.69710(11) 0.0170(3) Uani d . . . 1 . .
C C25 0.22953(5) 0.11464(17) 0.65394(11) 0.0196(3) Uani d . . . 1 . .
H H25 0.2472 0.1633 0.6301 0.024 Uiso calc U . R 1 . .
C C26 0.23230(6) -0.00410(18) 0.64543(12) 0.0235(4) Uani d . . . 1 . .
H H26 0.2516 -0.0355 0.6158 0.028 Uiso calc U . R 1 . .
C C27 0.20700(6) -0.07739(18) 0.68005(13) 0.0249(4) Uani d . . . 1 . .
H H27 0.2084 -0.1586 0.6734 0.03 Uiso calc U . R 1 . .
C C28 0.17957(6) -0.02953(17) 0.72467(12) 0.0230(4) Uani d . . . 1 . .
H H28 0.1628 -0.0788 0.7501 0.028 Uiso calc U . R 1 . .
C C29 0.17645(6) 0.08850(17) 0.73246(11) 0.0195(3) Uani d . . . 1 . .
H H29 0.1571 0.119 0.7624 0.023 Uiso calc U . R 1 . .
C C30 0.18488(6) 0.29694(16) 0.47559(11) 0.0186(3) Uani d . . . 1 . .
H H30A 0.2106 0.2481 0.4944 0.022 Uiso calc U . R 1 . .
H H30B 0.1689 0.2763 0.4164 0.022 Uiso calc U . R 1 . .
C C31 0.19417(5) 0.42196(16) 0.48668(11) 0.0172(3) Uani d . . . 1 . .
C C32 0.16679(6) 0.50467(16) 0.43716(11) 0.0185(3) Uani d . . . 1 . .
H H32 0.1433 0.4798 0.3923 0.022 Uiso calc U . R 1 . .
C C33 0.17338(6) 0.62158(17) 0.45251(13) 0.0221(3) Uani d . . . 1 . .
H H33 0.1546 0.6757 0.418 0.027 Uiso calc U . R 1 . .
C C34 0.20727(7) 0.66051(19) 0.51796(14) 0.0261(4) Uani d . . . 1 . .
H H34 0.2113 0.7408 0.5291 0.031 Uiso calc U . R 1 . .
C C35 0.23513(6) 0.58092(19) 0.56693(13) 0.0257(4) Uani d . . . 1 . .
H H35 0.2587 0.6068 0.6112 0.031 Uiso calc U . R 1 . .
C C36 0.22878(6) 0.46360(18) 0.55152(12) 0.0214(3) Uani d . . . 1 . .
H H36 0.2482 0.4102 0.5855 0.026 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 N3 . 2.2130(15) ?
Zr1 N1 . 2.2136(15) ?
Zr1 C23 . 2.3060(17) ?
Zr1 C30 . 2.3158(17) ?
Zr1 N4 . 2.3691(15) ?
Zr1 N2 . 2.3724(16) ?
Zr1 C31 . 2.8087(17) ?
Zr1 C24 . 2.8394(17) ?
N1 C1 . 1.367(2) ?
N1 C4 . 1.401(2) ?
N2 C5 . 1.360(2) ?
N2 C9 . 1.366(2) ?
N3 C12 . 1.374(2) ?
N3 C15 . 1.394(2) ?
N4 C20 . 1.353(2) ?
N4 C16 . 1.364(2) ?
C1 C2 . 1.402(3) ?
C1 C11 . 1.483(3) ?
C2 C3 . 1.387(3) ?
C3 C4 . 1.406(3) ?
C3 C10 . 1.509(3) ?
C4 C5 . 1.419(3) ?
C5 C6 . 1.402(3) ?
C6 C7 . 1.367(3) ?
C7 C8 . 1.392(3) ?
C8 C9 . 1.362(3) ?
C12 C13 . 1.385(3) ?
C12 C22 . 1.495(3) ?
C13 C14 . 1.407(3) ?
C14 C15 . 1.398(3) ?
C14 C21 . 1.499(3) ?
C15 C16 . 1.428(3) ?
C16 C17 . 1.403(3) ?
C17 C18 . 1.374(3) ?
C18 C19 . 1.388(3) ?
C19 C20 . 1.377(3) ?
C23 C24 . 1.472(3) ?
C24 C29 . 1.408(2) ?
C24 C25 . 1.408(3) ?
C25 C26 . 1.388(3) ?
C26 C27 . 1.391(3) ?
C27 C28 . 1.392(3) ?
C28 C29 . 1.380(3) ?
C30 C31 . 1.482(3) ?
C31 C32 . 1.408(3) ?
C31 C36 . 1.409(2) ?
C32 C33 . 1.384(3) ?
C33 C34 . 1.390(3) ?
C34 C35 . 1.388(3) ?
C35 C36 . 1.388(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Zr1 N1 . . 88.31(6) ?
N3 Zr1 C23 . . 152.12(6) ?
N1 Zr1 C23 . . 90.55(6) ?
N3 Zr1 C30 . . 94.01(6) ?
N1 Zr1 C30 . . 151.86(6) ?
C23 Zr1 C30 . . 99.91(6) ?
N3 Zr1 N4 . . 70.66(5) ?
N1 Zr1 N4 . . 97.36(6) ?
C23 Zr1 N4 . . 81.88(6) ?
C30 Zr1 N4 . . 109.88(6) ?
N3 Zr1 N2 . . 97.95(6) ?
N1 Zr1 N2 . . 70.53(6) ?
C23 Zr1 N2 . . 107.90(6) ?
C30 Zr1 N2 . . 81.38(6) ?
N4 Zr1 N2 . . 164.05(5) ?
N3 Zr1 C31 . . 85.57(5) ?
N1 Zr1 C31 . . 173.35(6) ?
C23 Zr1 C31 . . 93.64(6) ?
C30 Zr1 C31 . . 31.80(6) ?
N4 Zr1 C31 . . 78.15(5) ?
N2 Zr1 C31 . . 112.90(5) ?
N3 Zr1 C24 . . 169.67(5) ?
N1 Zr1 C24 . . 81.56(5) ?
C23 Zr1 C24 . . 31.10(6) ?
C30 Zr1 C24 . . 93.99(6) ?
N4 Zr1 C24 . . 112.49(5) ?
N2 Zr1 C24 . . 76.83(5) ?
C31 Zr1 C24 . . 104.64(5) ?
C1 N1 C4 . . 106.82(15) ?
C1 N1 Zr1 . . 134.03(13) ?
C4 N1 Zr1 . . 119.13(12) ?
C5 N2 C9 . . 117.73(16) ?
C5 N2 Zr1 . . 116.45(12) ?
C9 N2 Zr1 . . 125.81(13) ?
C12 N3 C15 . . 106.21(16) ?
C12 N3 Zr1 . . 134.15(14) ?
C15 N3 Zr1 . . 119.57(11) ?
C20 N4 C16 . . 118.02(16) ?
C20 N4 Zr1 . . 125.87(12) ?
C16 N4 Zr1 . . 115.91(11) ?
N1 C1 C2 . . 109.20(18) ?
N1 C1 C11 . . 123.33(18) ?
C2 C1 C11 . . 127.42(18) ?
C3 C2 C1 . . 108.40(17) ?
C2 C3 C4 . . 106.20(17) ?
C2 C3 C10 . . 125.35(18) ?
C4 C3 C10 . . 128.4(2) ?
N1 C4 C3 . . 109.36(17) ?
N1 C4 C5 . . 117.78(15) ?
C3 C4 C5 . . 132.30(18) ?
N2 C5 C6 . . 120.15(18) ?
N2 C5 C4 . . 115.19(16) ?
C6 C5 C4 . . 124.66(17) ?
C7 C6 C5 . . 120.82(19) ?
C6 C7 C8 . . 118.8(2) ?
C9 C8 C7 . . 118.6(2) ?
C8 C9 N2 . . 123.66(19) ?
N3 C12 C13 . . 109.49(18) ?
N3 C12 C22 . . 123.20(18) ?
C13 C12 C22 . . 127.31(18) ?
C12 C13 C14 . . 108.70(17) ?
C15 C14 C13 . . 105.01(18) ?
C15 C14 C21 . . 129.8(2) ?
C13 C14 C21 . . 125.16(19) ?
N3 C15 C14 . . 110.57(17) ?
N3 C15 C16 . . 117.17(16) ?
C14 C15 C16 . . 132.17(19) ?
N4 C16 C17 . . 120.64(17) ?
N4 C16 C15 . . 115.49(16) ?
C17 C16 C15 . . 123.86(17) ?
C18 C17 C16 . . 119.94(18) ?
C17 C18 C19 . . 119.29(19) ?
C20 C19 C18 . . 118.50(18) ?
N4 C20 C19 . . 123.37(17) ?
C24 C23 Zr1 . . 94.89(11) ?
C29 C24 C25 . . 116.70(17) ?
C29 C24 C23 . . 120.93(16) ?
C25 C24 C23 . . 122.22(16) ?
C29 C24 Zr1 . . 106.30(11) ?
C25 C24 Zr1 . . 106.21(11) ?
C23 C24 Zr1 . . 54.02(9) ?
C26 C25 C24 . . 121.61(17) ?
C25 C26 C27 . . 120.44(18) ?
C26 C27 C28 . . 118.77(19) ?
C29 C28 C27 . . 120.87(18) ?
C28 C29 C24 . . 121.58(18) ?
C31 C30 Zr1 . . 92.76(11) ?
C32 C31 C36 . . 117.03(17) ?
C32 C31 C30 . . 121.22(16) ?
C36 C31 C30 . . 121.57(17) ?
C32 C31 Zr1 . . 104.95(11) ?
C36 C31 Zr1 . . 105.73(11) ?
C30 C31 Zr1 . . 55.44(8) ?
C33 C32 C31 . . 121.28(17) ?
C32 C33 C34 . . 120.63(19) ?
C35 C34 C33 . . 119.29(19) ?
C34 C35 C36 . . 120.29(18) ?
C35 C36 C31 . . 121.45(18) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene, pentane'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive,Photo-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_cm299_a
_database_code_depnum_ccdc_archive 'CCDC 1992973'
loop_
_audit_author_name
_audit_author_address
'Brian S. Dolinar'
;West Virginia University
United States of America
;
_audit_update_record             
;
2020-03-26 deposited with the CCDC.	2020-04-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_cm299_a             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note
RESPONSE: Several reflections at low angles were affected by the beam stop
;
# Added during the CSD deposition process: Thursday 26 March 2020 03:21 PM
# end Validation Reply Form

_audit_creation_date             2020-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
loop_
_audit_author_email
pnd0003@mix.wvu.edu
?
camilsmann@mail.wvu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H42 N4 Zr, 1.5(C7 H8)'
_chemical_formula_sum            'C60.50 H54 N4 Zr'
_chemical_formula_weight         928.29
_chemical_melting_point          ?
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'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   15.9626(8)
_cell_length_b                   19.6034(9)
_cell_length_c                   16.6714(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.863(2)
_cell_angle_gamma                90
_cell_volume                     4733.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9119
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.506
_cell_measurement_theta_min      3.115
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0922 before and 0.0741 after correction. The Ratio of minimum to maximum transmission is 0.8164. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1940
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            94628
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.616
_diffrn_reflns_theta_min         2.887
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  WVU-Venture
_diffrn_measurement_method       '0.5\ ω and 0.5\ φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'TRIUMPH monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Mo sealed X-ray tube'
_diffrn_source_type              'Mo sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8198
_reflns_number_total             10870
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3(Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         10870
_refine_ls_number_restraints     799
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²+8.6480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57 \\sim C51A
\\sim C52A \\sim C53A \\sim C54A \\sim C55A \\sim C56A \\sim C57A \\sim C51B
\\sim C52B \\sim C53B \\sim C54B \\sim C55B \\sim C56B \\sim C57B: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C58A \\sim C59A \\sim C60A \\sim C61A \\sim C62A \\sim C63A \\sim C64A \\sim
C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Same fragment restrains
{C51A, C52A, C53A, C54A, C55A, C56A, C57A} sigma for 1-2: 0.01, 1-3: 0.02
{C51B, C52B, C53B, C54B, C55B, C56B, C57B} sigma for 1-2: 0.01, 1-3: 0.02
{C58, C59, C60, C61, C62, C63, C64} sigma for 1-2: 0.01, 1-3: 0.02
{C58A, C59A, C60A, C61A, C62A, C63A, C64A} sigma for 1-2: 0.01, 1-3: 0.02
as
{C51, C52, C53, C54, C55, C56, C57}
4. Others
 1*[Sof(C51)+Sof(H51A)+Sof(H51B)+Sof(H51C)+Sof(C52)+Sof(C53)+Sof(H53)+Sof(C54)+
 Sof(H54)+Sof(C55)+Sof(H55)+Sof(C56)+Sof(H56)+Sof(C57)+Sof(H57)]+1*[Sof(C51A)+
 Sof(H51D)+Sof(H51E)+Sof(H51F)+Sof(C52A)+Sof(C53A)+Sof(H53A)+Sof(C54A)+
 Sof(H54A)+Sof(C55A)+Sof(H55A)+Sof(C56A)+Sof(H56A)+Sof(C57A)+Sof(H57A)]+1*
 [Sof(C51B)+Sof(H51G)+Sof(H51H)+Sof(H51I)+Sof(C52B)+Sof(C53B)+Sof(H53B)+
 Sof(C54B)+Sof(H54B)+Sof(C55B)+Sof(H55B)+Sof(C56B)+Sof(H56B)+Sof(C57B)+
 Sof(H57B)]=1 with esd of 0
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52)=Sof(C53)=Sof(H53)=Sof(C54)=
 Sof(H54)=Sof(C55)=Sof(H55)=Sof(C56)=Sof(H56)=Sof(C57)=Sof(H57)=FVAR(1)
 Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C52A)=Sof(C53A)=Sof(H53A)=
 Sof(C54A)=Sof(H54A)=Sof(C55A)=Sof(H55A)=Sof(C56A)=Sof(H56A)=Sof(C57A)=
 Sof(H57A)=FVAR(2)
 Sof(C51B)=Sof(H51G)=Sof(H51H)=Sof(H51I)=Sof(C52B)=Sof(C53B)=Sof(H53B)=
 Sof(C54B)=Sof(H54B)=Sof(C55B)=Sof(H55B)=Sof(C56B)=Sof(H56B)=Sof(C57B)=
 Sof(H57B)=FVAR(3)
 Sof(C58A)=Sof(H58A)=Sof(H58B)=Sof(H58C)=Sof(C59A)=Sof(C60A)=Sof(H60A)=
 Sof(C61A)=Sof(H61A)=Sof(C62A)=Sof(H62A)=Sof(C63A)=Sof(H63A)=Sof(C64A)=
 Sof(H64A)=0.5*(1-FVAR(5))
 Sof(C58)=Sof(H58D)=Sof(H58E)=Sof(H58F)=Sof(C59)=Sof(C60)=Sof(H60)=Sof(C61)=
 Sof(H61)=Sof(C62)=Sof(H62)=Sof(C63)=Sof(H63)=Sof(C64)=Sof(H64)=0.5*FVAR(5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42),
 C43(H43), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C53(H53),
  C54(H54), C55(H55), C56(H56), C57(H57), C53A(H53A), C54A(H54A), C55A(H55A),
 C56A(H56A), C57A(H57A), C53B(H53B), C54B(H54B), C55B(H55B), C56B(H56B),
 C57B(H57B), C60A(H60A), C61A(H61A), C62A(H62A), C63A(H63A), C64A(H64A),
 C60(H60), C61(H61), C62(H62), C63(H63), C64(H64)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C51(H51A,H51B,H51C), C51A(H51D,H51E,H51F), C51B(H51G,H51H,H51I),
 C58A(H58A,H58B,H58C), C58(H58D,H58E,H58F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zr1 Zr 0.32773(2) 0.50949(2) 0.65187(2) 0.01877(7) Uani 1 1 d . . . . .
N1 N 0.36151(15) 0.51271(12) 0.53804(15) 0.0254(5) Uani 1 1 d . . . . .
N2 N 0.26545(15) 0.41117(12) 0.56881(16) 0.0261(5) Uani 1 1 d . . . . .
N3 N 0.22015(15) 0.50143(11) 0.70017(14) 0.0220(5) Uani 1 1 d . . . . .
N4 N 0.19218(15) 0.56802(12) 0.55214(15) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.4057(2) 0.55723(17) 0.5061(2) 0.0375(8) Uani 1 1 d . . . . .
C2 C 0.3874(3) 0.53973(18) 0.4194(2) 0.0450(9) Uani 1 1 d . . . . .
H2 H 0.4100 0.5629 0.3824 0.054 Uiso 1 1 calc R . . . .
C3 C 0.3305(3) 0.48256(18) 0.3960(2) 0.0438(8) Uani 1 1 d . . . . .
C4 C 0.3149(2) 0.46492(16) 0.46965(19) 0.0307(7) Uani 1 1 d . . . . .
C5 C 0.26739(19) 0.40959(15) 0.4889(2) 0.0295(6) Uani 1 1 d . . . . .
C6 C 0.2255(2) 0.35433(16) 0.4313(2) 0.0353(7) Uani 1 1 d . . . . .
H6 H 0.2247 0.3535 0.3740 0.042 Uiso 1 1 calc R . . . .
C7 C 0.1863(2) 0.30234(17) 0.4577(2) 0.0402(8) Uani 1 1 d . . . . .
H7 H 0.1592 0.2649 0.4193 0.048 Uiso 1 1 calc R . . . .
C8 C 0.1859(2) 0.30408(16) 0.5416(2) 0.0362(7) Uani 1 1 d . . . . .
H8 H 0.1591 0.2682 0.5612 0.043 Uiso 1 1 calc R . . . .
C9 C 0.2252(2) 0.35882(15) 0.5941(2) 0.0302(6) Uani 1 1 d . . . . .
H9 H 0.2247 0.3608 0.6508 0.036 Uiso 1 1 calc R . . . .
C10 C 0.4618(3) 0.6137(2) 0.5606(3) 0.0497(9) Uani 1 1 d . . . . .
H10A H 0.4211 0.6488 0.5668 0.075 Uiso 1 1 calc GR . . . .
H10B H 0.4987 0.6336 0.5321 0.075 Uiso 1 1 calc GR . . . .
H10C H 0.5029 0.5965 0.6192 0.075 Uiso 1 1 calc GR . . . .
C11 C 0.2918(4) 0.4495(2) 0.3058(3) 0.0717(14) Uani 1 1 d . . . . .
H11A H 0.3261 0.4075 0.3081 0.108 Uiso 1 1 calc GR . . . .
H11B H 0.2976 0.4809 0.2628 0.108 Uiso 1 1 calc GR . . . .
H11C H 0.2265 0.4385 0.2881 0.108 Uiso 1 1 calc GR . . . .
C12 C 0.21897(19) 0.47430(13) 0.77535(18) 0.0228(6) Uani 1 1 d . . . . .
C13 C 0.13125(18) 0.48246(14) 0.77299(18) 0.0239(6) Uani 1 1 d . . . . .
H13 H 0.1124 0.4677 0.8171 0.029 Uiso 1 1 calc R . . . .
C14 C 0.07572(18) 0.51606(14) 0.69453(19) 0.0247(6) Uani 1 1 d . . . . .
C15 C 0.13143(17) 0.52835(13) 0.64958(18) 0.0203(5) Uani 1 1 d . . . . .
C16 C 0.11733(18) 0.56417(14) 0.57078(18) 0.0232(6) Uani 1 1 d . . . . .
C17 C 0.03470(19) 0.59590(15) 0.51436(18) 0.0262(6) Uani 1 1 d . . . . .
H17 H -0.0182 0.5921 0.5265 0.031 Uiso 1 1 calc R . . . .
C18 C 0.0289(2) 0.63204(16) 0.4425(2) 0.0333(7) Uani 1 1 d . . . . .
H18 H -0.0272 0.6537 0.4050 0.040 Uiso 1 1 calc R . . . .
C19 C 0.1071(2) 0.63682(16) 0.4248(2) 0.0328(7) Uani 1 1 d . . . . .
H19 H 0.1053 0.6624 0.3756 0.039 Uiso 1 1 calc R . . . .
C20 C 0.1855(2) 0.60409(15) 0.47943(19) 0.0278(6) Uani 1 1 d . . . . .
H20 H 0.2380 0.6064 0.4665 0.033 Uiso 1 1 calc R . . . .
C21 C 0.30243(19) 0.44276(15) 0.84461(18) 0.0258(6) Uani 1 1 d . . . . .
H21A H 0.3138 0.3984 0.8238 0.039 Uiso 1 1 calc GR . . . .
H21B H 0.2930 0.4364 0.8985 0.039 Uiso 1 1 calc GR . . . .
H21C H 0.3557 0.4726 0.8573 0.039 Uiso 1 1 calc GR . . . .
C22 C -0.0242(2) 0.53522(17) 0.6666(2) 0.0343(7) Uani 1 1 d . . . . .
H22A H -0.0302 0.5850 0.6646 0.052 Uiso 1 1 calc GR . . . .
H22B H -0.0458 0.5168 0.7092 0.052 Uiso 1 1 calc GR . . . .
H22C H -0.0615 0.5163 0.6079 0.052 Uiso 1 1 calc GR . . . .
C23 C 0.42170(18) 0.57996(13) 0.75601(18) 0.0217(5) Uani 1 1 d . . . . .
C24 C 0.50090(17) 0.55202(13) 0.81732(18) 0.0191(5) Uani 1 1 d . . . . .
C25 C 0.51424(17) 0.47659(13) 0.81092(17) 0.0178(5) Uani 1 1 d . . . . .
C26 C 0.44872(17) 0.44092(13) 0.74281(17) 0.0182(5) Uani 1 1 d . . . . .
C27 C 0.39788(17) 0.65340(13) 0.74952(17) 0.0198(5) Uani 1 1 d . . . . .
C28 C 0.31087(18) 0.67337(14) 0.74293(17) 0.0222(6) Uani 1 1 d . . . . .
H28 H 0.2684 0.6396 0.7436 0.027 Uiso 1 1 calc R . . . .
C29 C 0.28585(19) 0.74165(14) 0.73550(19) 0.0276(6) Uani 1 1 d . . . . .
H29 H 0.2274 0.7545 0.7330 0.033 Uiso 1 1 calc R . . . .
C30 C 0.3459(2) 0.79105(14) 0.73173(19) 0.0294(6) Uani 1 1 d . . . . .
H30 H 0.3287 0.8378 0.7266 0.035 Uiso 1 1 calc R . . . .
C31 C 0.4310(2) 0.77234(14) 0.73548(18) 0.0254(6) Uani 1 1 d . . . . .
H31 H 0.4716 0.8063 0.7317 0.030 Uiso 1 1 calc R . . . .
C32 C 0.45718(19) 0.70472(14) 0.74459(18) 0.0238(6) Uani 1 1 d . . . . .
H32 H 0.5161 0.6926 0.7476 0.029 Uiso 1 1 calc R . . . .
C33 C 0.57276(18) 0.59489(13) 0.88679(17) 0.0210(5) Uani 1 1 d . . . . .
C34 C 0.5483(2) 0.64109(14) 0.93742(18) 0.0277(6) Uani 1 1 d . . . . .
H34 H 0.4872 0.6407 0.9336 0.033 Uiso 1 1 calc R . . . .
C35 C 0.6118(3) 0.68743(16) 0.9930(2) 0.0377(8) Uani 1 1 d . . . . .
H35 H 0.5937 0.7186 1.0264 0.045 Uiso 1 1 calc R . . . .
C36 C 0.7010(3) 0.68868(17) 1.0001(2) 0.0433(9) Uani 1 1 d . . . . .
H36 H 0.7438 0.7214 1.0369 0.052 Uiso 1 1 calc R . . . .
C37 C 0.7277(2) 0.64210(17) 0.9534(2) 0.0401(8) Uani 1 1 d . . . . .
H37 H 0.7897 0.6418 0.9598 0.048 Uiso 1 1 calc R . . . .
C38 C 0.66432(19) 0.59535(15) 0.89682(19) 0.0283(6) Uani 1 1 d . . . . .
H38 H 0.6835 0.5636 0.8649 0.034 Uiso 1 1 calc R . . . .
C39 C 0.59576(17) 0.44295(13) 0.88243(17) 0.0183(5) Uani 1 1 d . . . . .
C40 C 0.60568(18) 0.44430(14) 0.96967(18) 0.0222(6) Uani 1 1 d . . . . .
H40 H 0.5632 0.4698 0.9840 0.027 Uiso 1 1 calc R . . . .
C41 C 0.67641(19) 0.40903(14) 1.03569(19) 0.0274(6) Uani 1 1 d . . . . .
H41 H 0.6816 0.4098 1.0946 0.033 Uiso 1 1 calc R . . . .
C42 C 0.7394(2) 0.37266(15) 1.0156(2) 0.0322(7) Uani 1 1 d . . . . .
H42 H 0.7878 0.3482 1.0606 0.039 Uiso 1 1 calc R . . . .
C43 C 0.7318(2) 0.37197(16) 0.9298(2) 0.0316(7) Uani 1 1 d . . . . .
H43 H 0.7757 0.3477 0.9163 0.038 Uiso 1 1 calc R . . . .
C44 C 0.66030(18) 0.40652(14) 0.86336(18) 0.0234(6) Uani 1 1 d . . . . .
H44 H 0.6553 0.4054 0.8045 0.028 Uiso 1 1 calc R . . . .
C45 C 0.45556(17) 0.36556(13) 0.73653(18) 0.0203(5) Uani 1 1 d . . . . .
C46 C 0.46005(17) 0.32153(14) 0.80444(19) 0.0236(6) Uani 1 1 d . . . . .
H46 H 0.4632 0.3402 0.8582 0.028 Uiso 1 1 calc R . . . .
C47 C 0.45994(19) 0.25109(15) 0.7948(2) 0.0314(7) Uani 1 1 d . . . . .
H47 H 0.4623 0.2223 0.8415 0.038 Uiso 1 1 calc R . . . .
C48 C 0.4565(2) 0.22272(15) 0.7175(2) 0.0382(8) Uani 1 1 d . . . . .
H48 H 0.4560 0.1746 0.7109 0.046 Uiso 1 1 calc R . . . .
C49 C 0.4536(2) 0.26501(16) 0.6500(2) 0.0371(8) Uani 1 1 d . . . . .
H49 H 0.4522 0.2458 0.5971 0.044 Uiso 1 1 calc R . . . .
C50 C 0.45274(19) 0.33542(15) 0.65924(19) 0.0276(6) Uani 1 1 d . . . . .
H50 H 0.4502 0.3638 0.6121 0.033 Uiso 1 1 calc R . . . .
C51 C 0.7888(6) 0.7545(6) 0.7999(7) 0.090(3) Uani 0.512(3) 1 d D U P A 1
H51A H 0.8415 0.7703 0.7893 0.136 Uiso 0.512(3) 1 calc GR . P A 1
H51B H 0.7804 0.7054 0.7886 0.136 Uiso 0.512(3) 1 calc GR . P A 1
H51C H 0.8004 0.7637 0.8615 0.136 Uiso 0.512(3) 1 calc GR . P A 1
C52 C 0.7028(7) 0.7918(4) 0.7391(7) 0.0584(17) Uani 0.512(3) 1 d D U P A 1
C53 C 0.6898(13) 0.8600(6) 0.7525(14) 0.062(2) Uani 0.512(3) 1 d D U P A 1
H53 H 0.7327 0.8834 0.8029 0.075 Uiso 0.512(3) 1 calc R . P A 1
C54 C 0.6133(8) 0.8933(5) 0.6914(7) 0.063(2) Uani 0.512(3) 1 d D U P A 1
H54 H 0.6054 0.9404 0.6996 0.075 Uiso 0.512(3) 1 calc R . P A 1
C55 C 0.5457(6) 0.8593(4) 0.6161(6) 0.0630(17) Uani 0.512(3) 1 d D U P A 1
H55 H 0.4923 0.8824 0.5759 0.076 Uiso 0.512(3) 1 calc R . P A 1
C56 C 0.5606(7) 0.7933(5) 0.6043(7) 0.0536(18) Uani 0.512(3) 1 d D U P A 1
H56 H 0.5201 0.7704 0.5522 0.064 Uiso 0.512(3) 1 calc R . P A 1
C57 C 0.6363(12) 0.7573(6) 0.6692(12) 0.050(2) Uani 0.512(3) 1 d D U P A 1
H57 H 0.6410 0.7093 0.6643 0.060 Uiso 0.512(3) 1 calc R . P A 1
C51A C 0.8224(13) 0.7885(12) 0.8683(13) 0.060(5) Uani 0.176(3) 1 d D U P B 2
H51D H 0.8673 0.8246 0.8751 0.090 Uiso 0.176(3) 1 calc GR . P B 2
H51E H 0.8501 0.7440 0.8677 0.090 Uiso 0.176(3) 1 calc GR . P B 2
H51F H 0.8045 0.7903 0.9177 0.090 Uiso 0.176(3) 1 calc GR . P B 2
C52A C 0.7392(17) 0.7984(10) 0.7836(15) 0.058(3) Uani 0.176(3) 1 d D U P B 2
C53A C 0.702(3) 0.8636(12) 0.762(3) 0.061(3) Uani 0.176(3) 1 d D U P B 2
H53A H 0.7331 0.9026 0.7949 0.074 Uiso 0.176(3) 1 calc R . P B 2
C54A C 0.616(2) 0.8686(15) 0.692(2) 0.061(3) Uani 0.176(3) 1 d D U P B 2
H54A H 0.5804 0.9088 0.6857 0.073 Uiso 0.176(3) 1 calc R . P B 2
C55A C 0.578(2) 0.8152(16) 0.628(2) 0.055(3) Uani 0.176(3) 1 d D U P B 2
H55A H 0.5226 0.8216 0.5767 0.066 Uiso 0.176(3) 1 calc R . P B 2
C56A C 0.624(2) 0.7559(16) 0.6432(17) 0.053(3) Uani 0.176(3) 1 d D U P B 2
H56A H 0.6059 0.7215 0.5990 0.064 Uiso 0.176(3) 1 calc R . P B 2
C57A C 0.7011(17) 0.7450(9) 0.7267(15) 0.059(3) Uani 0.176(3) 1 d D U P B 2
H57A H 0.7259 0.7005 0.7429 0.070 Uiso 0.176(3) 1 calc R . P B 2
C51B C 0.4907(9) 0.8008(7) 0.5547(8) 0.068(3) Uani 0.312(3) 1 d D U P C 3
H51G H 0.4386 0.7930 0.5700 0.102 Uiso 0.312(3) 1 calc GR . P C 3
H51H H 0.4953 0.7628 0.5186 0.102 Uiso 0.312(3) 1 calc GR . P C 3
H51I H 0.4812 0.8434 0.5214 0.102 Uiso 0.312(3) 1 calc GR . P C 3
C52B C 0.5779(12) 0.8055(8) 0.6374(12) 0.052(2) Uani 0.312(3) 1 d D U P C 3
C53B C 0.5957(12) 0.8712(9) 0.6732(13) 0.060(2) Uani 0.312(3) 1 d D U P C 3
H53B H 0.5548 0.9082 0.6475 0.071 Uiso 0.312(3) 1 calc R . P C 3
C54B C 0.6765(14) 0.8784(8) 0.7483(15) 0.062(3) Uani 0.312(3) 1 d D U P C 3
H54B H 0.6891 0.9214 0.7772 0.074 Uiso 0.312(3) 1 calc R . P C 3
C55B C 0.7432(10) 0.8246(7) 0.7854(10) 0.063(2) Uani 0.312(3) 1 d D U P C 3
H55B H 0.7981 0.8322 0.8374 0.076 Uiso 0.312(3) 1 calc R . P C 3
C56B C 0.7263(10) 0.7638(7) 0.7452(11) 0.058(3) Uani 0.312(3) 1 d D U P C 3
H56B H 0.7678 0.7268 0.7692 0.070 Uiso 0.312(3) 1 calc R . P C 3
C57B C 0.6438(18) 0.7557(11) 0.665(2) 0.053(3) Uani 0.312(3) 1 d D U P C 3
H57B H 0.6352 0.7155 0.6305 0.064 Uiso 0.312(3) 1 calc R . P C 3
C58A C -0.0894(15) 0.5954(12) 0.8879(15) 0.094(6) Uani 0.229(6) 1 d D U P D -2
H58A H -0.0685 0.6404 0.9146 0.142 Uiso 0.229(6) 1 calc GR . P D -2
H58B H -0.1563 0.5916 0.8690 0.142 Uiso 0.229(6) 1 calc GR . P D -2
H58C H -0.0750 0.5900 0.8366 0.142 Uiso 0.229(6) 1 calc GR . P D -2
C59A C -0.0413(12) 0.5410(12) 0.9545(13) 0.070(3) Uani 0.229(6) 1 d D U P D -2
C60A C 0.0528(13) 0.5348(15) 0.9763(16) 0.074(4) Uani 0.229(6) 1 d D U P D -2
H60A H 0.0821 0.5615 0.9479 0.089 Uiso 0.229(6) 1 calc R . P D -2
C61A C 0.1012(14) 0.4882(17) 1.0406(19) 0.074(4) Uani 0.229(6) 1 d D U P D -2
H61A H 0.1636 0.4794 1.0518 0.089 Uiso 0.229(6) 1 calc R . P D -2
C62A C 0.0627(14) 0.4521(13) 1.0917(14) 0.074(4) Uani 0.229(6) 1 d D U P D -2
H62A H 0.1007 0.4255 1.1412 0.089 Uiso 0.229(6) 1 calc R . P D -2
C63A C -0.0286(14) 0.457(2) 1.068(2) 0.075(4) Uani 0.229(6) 1 d D U P D -2
H63A H -0.0573 0.4312 1.0976 0.090 Uiso 0.229(6) 1 calc R . P D -2
C64A C -0.0822(15) 0.502(3) 0.996(4) 0.073(4) Uani 0.229(6) 1 d D U P D -2
H64A H -0.1471 0.5045 0.9777 0.088 Uiso 0.229(6) 1 calc R . P D -2
C58 C -0.0003(16) 0.4268(12) 1.0967(14) 0.100(7) Uani 0.271(6) 1 d D U P D -1
H58D H -0.0267 0.4460 1.1352 0.150 Uiso 0.271(6) 1 calc GR . P D -1
H58E H 0.0643 0.4143 1.1322 0.150 Uiso 0.271(6) 1 calc GR . P D -1
H58F H -0.0353 0.3861 1.0670 0.150 Uiso 0.271(6) 1 calc GR . P D -1
C59 C -0.0052(10) 0.4787(9) 1.0289(11) 0.071(3) Uani 0.271(6) 1 d D U P D -1
C60 C -0.0933(14) 0.507(3) 0.985(3) 0.075(3) Uani 0.271(6) 1 d D U P D -1
H60 H -0.1407 0.4985 1.0039 0.090 Uiso 0.271(6) 1 calc R . P D -1
C61 C -0.1085(9) 0.5473(10) 0.9126(11) 0.068(3) Uani 0.271(6) 1 d D U P D -1
H61 H -0.1697 0.5628 0.8783 0.082 Uiso 0.271(6) 1 calc R . P D -1
C62 C -0.0381(12) 0.5675(12) 0.8860(13) 0.073(4) Uani 0.271(6) 1 d D U P D -1
H62 H -0.0515 0.5963 0.8362 0.087 Uiso 0.271(6) 1 calc R . P D -1
C63 C 0.0477(11) 0.5443(17) 0.9339(18) 0.068(3) Uani 0.271(6) 1 d D U P D -1
H63 H 0.0967 0.5569 0.9188 0.081 Uiso 0.271(6) 1 calc R . P D -1
C64 C 0.0652(10) 0.5001(17) 1.0085(18) 0.069(3) Uani 0.271(6) 1 d D U P D -1
H64 H 0.1266 0.4857 1.0440 0.083 Uiso 0.271(6) 1 calc R . P D -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zr1 N1 2.181(2) . ?
Zr1 N2 2.337(2) . ?
Zr1 N3 2.187(2) . ?
Zr1 N4 2.395(2) . ?
Zr1 C23 2.232(3) . ?
Zr1 C26 2.318(2) . ?
N1 C1 1.363(4) . ?
N1 C4 1.420(4) . ?
N2 C5 1.346(4) . ?
N2 C9 1.368(4) . ?
N3 C12 1.369(3) . ?
N3 C15 1.411(3) . ?
N4 C16 1.357(3) . ?
N4 C20 1.368(4) . ?
C1 C2 1.393(5) . ?
C1 C10 1.474(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(5) . ?
C3 C4 1.395(4) . ?
C3 C11 1.510(5) . ?
C4 C5 1.435(4) . ?
C5 C6 1.415(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.362(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.359(4) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.393(4) . ?
C12 C21 1.482(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(4) . ?
C14 C15 1.404(4) . ?
C14 C22 1.509(4) . ?
C15 C16 1.422(4) . ?
C16 C17 1.403(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.361(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.401(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.361(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.363(4) . ?
C23 C27 1.481(4) . ?
C24 C25 1.504(3) . ?
C24 C33 1.499(4) . ?
C25 C26 1.369(4) . ?
C25 C39 1.498(3) . ?
C26 C45 1.488(4) . ?
C27 C28 1.402(4) . ?
C27 C32 1.407(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.382(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.383(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.379(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.401(4) . ?
C33 C38 1.400(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.386(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.378(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.378(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.396(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(4) . ?
C39 C44 1.396(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.385(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.385(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.383(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.387(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.401(4) . ?
C45 C50 1.401(4) . ?
C46 H46 0.9500 . ?
C46 C47 1.390(4) . ?
C47 H47 0.9500 . ?
C47 C48 1.383(5) . ?
C48 H48 0.9500 . ?
C48 C49 1.384(5) . ?
C49 H49 0.9500 . ?
C49 C50 1.390(4) . ?
C50 H50 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C51 C52 1.508(11) . ?
C52 C53 1.386(11) . ?
C52 C57 1.379(13) . ?
C53 H53 0.9500 . ?
C53 C54 1.382(9) . ?
C54 H54 0.9500 . ?
C54 C55 1.430(11) . ?
C55 H55 0.9500 . ?
C55 C56 1.344(11) . ?
C56 H56 0.9500 . ?
C56 C57 1.424(15) . ?
C57 H57 0.9500 . ?
C51A H51D 0.9800 . ?
C51A H51E 0.9800 . ?
C51A H51F 0.9800 . ?
C51A C52A 1.490(13) . ?
C52A C53A 1.392(13) . ?
C52A C57A 1.370(14) . ?
C53A H53A 0.9500 . ?
C53A C54A 1.383(11) . ?
C54A H54A 0.9500 . ?
C54A C55A 1.432(13) . ?
C55A H55A 0.9500 . ?
C55A C56A 1.339(13) . ?
C56A H56A 0.9500 . ?
C56A C57A 1.434(16) . ?
C57A H57A 0.9500 . ?
C51B H51G 0.9800 . ?
C51B H51H 0.9800 . ?
C51B H51I 0.9800 . ?
C51B C52B 1.494(13) . ?
C52B C53B 1.397(12) . ?
C52B C57B 1.365(14) . ?
C53B H53B 0.9500 . ?
C53B C54B 1.376(11) . ?
C54B H54B 0.9500 . ?
C54B C55B 1.440(13) . ?
C55B H55B 0.9500 . ?
C55B C56B 1.340(12) . ?
C56B H56B 0.9500 . ?
C56B C57B 1.439(17) . ?
C57B H57B 0.9500 . ?
C58A H58A 0.9800 . ?
C58A H58B 0.9800 . ?
C58A H58C 0.9800 . ?
C58A C59A 1.498(13) . ?
C59A C60A 1.395(13) . ?
C59A C64A 1.372(14) . ?
C60A H60A 0.9500 . ?
C60A C61A 1.373(12) . ?
C61A H61A 0.9500 . ?
C61A C62A 1.428(13) . ?
C62A H62A 0.9500 . ?
C62A C63A 1.342(13) . ?
C63A H63A 0.9500 . ?
C63A C64A 1.439(16) . ?
C64A H64A 0.9500 . ?
C58 H58D 0.9800 . ?
C58 H58E 0.9800 . ?
C58 H58F 0.9800 . ?
C58 C59 1.499(13) . ?
C59 C60 1.399(13) . ?
C59 C64 1.370(14) . ?
C60 H60 0.9500 . ?
C60 C61 1.375(12) . ?
C61 H61 0.9500 . ?
C61 C62 1.426(13) . ?
C62 H62 0.9500 . ?
C62 C63 1.343(12) . ?
C63 H63 0.9500 . ?
C63 C64 1.442(16) . ?
C64 H64 0.9500 . ?

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
N1 Zr1 N2 72.99(9) . . ?
N1 Zr1 N3 147.34(8) . . ?
N1 Zr1 N4 82.17(8) . . ?
N1 Zr1 C23 109.13(9) . . ?
N1 Zr1 C26 98.23(8) . . ?
N2 Zr1 N4 87.06(8) . . ?
N3 Zr1 N2 87.38(8) . . ?
N3 Zr1 N4 70.75(8) . . ?
N3 Zr1 C23 97.66(9) . . ?
N3 Zr1 C26 106.53(8) . . ?
C23 Zr1 N2 161.89(9) . . ?
C23 Zr1 N4 111.03(9) . . ?
C23 Zr1 C26 75.38(9) . . ?
C26 Zr1 N2 86.51(8) . . ?
C26 Zr1 N4 173.13(8) . . ?
C1 N1 Zr1 135.7(2) . . ?
C1 N1 C4 106.9(2) . . ?
C4 N1 Zr1 116.22(18) . . ?
C5 N2 Zr1 115.11(19) . . ?
C5 N2 C9 119.8(3) . . ?
C9 N2 Zr1 125.05(19) . . ?
C12 N3 Zr1 132.86(18) . . ?
C12 N3 C15 107.2(2) . . ?
C15 N3 Zr1 119.93(17) . . ?
C16 N4 Zr1 116.08(18) . . ?
C16 N4 C20 118.9(2) . . ?
C20 N4 Zr1 125.00(18) . . ?
N1 C1 C2 109.3(3) . . ?
N1 C1 C10 121.4(3) . . ?
C2 C1 C10 129.3(3) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 C1 108.5(3) . . ?
C3 C2 H2 125.8 . . ?
C2 C3 C4 106.9(3) . . ?
C2 C3 C11 124.8(3) . . ?
C4 C3 C11 128.3(4) . . ?
N1 C4 C5 117.8(3) . . ?
C3 C4 N1 108.4(3) . . ?
C3 C4 C5 133.7(3) . . ?
N2 C5 C4 116.0(3) . . ?
N2 C5 C6 119.2(3) . . ?
C6 C5 C4 124.8(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 121.1 . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 H8 121.1 . . ?
N2 C9 H9 118.5 . . ?
C8 C9 N2 123.0(3) . . ?
C8 C9 H9 118.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 109.3(2) . . ?
N3 C12 C21 121.4(2) . . ?
C13 C12 C21 129.3(3) . . ?
C12 C13 H13 125.8 . . ?
C12 C13 C14 108.3(2) . . ?
C14 C13 H13 125.8 . . ?
C13 C14 C15 106.6(2) . . ?
C13 C14 C22 125.3(3) . . ?
C15 C14 C22 128.1(3) . . ?
N3 C15 C16 117.8(2) . . ?
C14 C15 N3 108.6(2) . . ?
C14 C15 C16 133.5(2) . . ?
N4 C16 C15 115.2(2) . . ?
N4 C16 C17 119.5(3) . . ?
C17 C16 C15 125.3(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 118.9(3) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 H19 120.7 . . ?
N4 C20 H20 118.5 . . ?
C19 C20 N4 123.0(3) . . ?
C19 C20 H20 118.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 Zr1 116.29(19) . . ?
C24 C23 C27 125.0(2) . . ?
C27 C23 Zr1 118.48(18) . . ?
C23 C24 C25 117.1(2) . . ?
C23 C24 C33 121.4(2) . . ?
C33 C24 C25 121.4(2) . . ?
C26 C25 C24 118.7(2) . . ?
C26 C25 C39 122.7(2) . . ?
C39 C25 C24 118.5(2) . . ?
C25 C26 Zr1 112.47(18) . . ?
C25 C26 C45 120.8(2) . . ?
C45 C26 Zr1 126.53(18) . . ?
C28 C27 C23 119.5(2) . . ?
C28 C27 C32 117.7(2) . . ?
C32 C27 C23 122.7(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.5(3) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 119.6 . . ?
C31 C32 C27 120.9(3) . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C24 120.8(2) . . ?
C38 C33 C24 121.2(2) . . ?
C38 C33 C34 117.7(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.0(3) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.5(3) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.6(3) . . ?
C38 C37 H37 119.7 . . ?
C33 C38 H38 119.7 . . ?
C37 C38 C33 120.5(3) . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C25 120.1(2) . . ?
C40 C39 C44 118.4(2) . . ?
C44 C39 C25 121.4(2) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 C39 121.1(3) . . ?
C41 C40 H40 119.5 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.8(3) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 H42 120.1 . . ?
C43 C42 C41 119.9(3) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 119.8 . . ?
C42 C43 C44 120.4(3) . . ?
C44 C43 H43 119.8 . . ?
C39 C44 H44 119.8 . . ?
C43 C44 C39 120.4(3) . . ?
C43 C44 H44 119.8 . . ?
C46 C45 C26 122.3(2) . . ?
C50 C45 C26 120.6(2) . . ?
C50 C45 C46 117.0(2) . . ?
C45 C46 H46 119.3 . . ?
C47 C46 C45 121.4(3) . . ?
C47 C46 H46 119.3 . . ?
C46 C47 H47 119.8 . . ?
C48 C47 C46 120.3(3) . . ?
C48 C47 H47 119.8 . . ?
C47 C48 H48 120.3 . . ?
C47 C48 C49 119.5(3) . . ?
C49 C48 H48 120.3 . . ?
C48 C49 H49 119.9 . . ?
C48 C49 C50 120.2(3) . . ?
C50 C49 H49 119.9 . . ?
C45 C50 H50 119.2 . . ?
C49 C50 C45 121.5(3) . . ?
C49 C50 H50 119.2 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C52 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
C52 C51 H51C 109.5 . . ?
C53 C52 C51 120.9(9) . . ?
C57 C52 C51 119.4(9) . . ?
C57 C52 C53 119.7(10) . . ?
C52 C53 H53 120.6 . . ?
C54 C53 C52 118.9(11) . . ?
C54 C53 H53 120.6 . . ?
C53 C54 H54 118.9 . . ?
C53 C54 C55 122.2(10) . . ?
C55 C54 H54 118.9 . . ?
C54 C55 H55 121.2 . . ?
C56 C55 C54 117.6(9) . . ?
C56 C55 H55 121.2 . . ?
C55 C56 H56 119.6 . . ?
C55 C56 C57 120.7(9) . . ?
C57 C56 H56 119.6 . . ?
C52 C57 C56 120.4(9) . . ?
C52 C57 H57 119.8 . . ?
C56 C57 H57 119.8 . . ?
H51D C51A H51E 109.5 . . ?
H51D C51A H51F 109.5 . . ?
H51E C51A H51F 109.5 . . ?
C52A C51A H51D 109.5 . . ?
C52A C51A H51E 109.5 . . ?
C52A C51A H51F 109.5 . . ?
C53A C52A C51A 118.5(13) . . ?
C57A C52A C51A 121.0(13) . . ?
C57A C52A C53A 120.5(13) . . ?
C52A C53A H53A 121.7 . . ?
C54A C53A C52A 116.6(16) . . ?
C54A C53A H53A 121.7 . . ?
C53A C54A H54A 118.9 . . ?
C53A C54A C55A 122.3(15) . . ?
C55A C54A H54A 118.9 . . ?
C54A C55A H55A 121.0 . . ?
C56A C55A C54A 118.1(13) . . ?
C56A C55A H55A 121.0 . . ?
C55A C56A H56A 120.4 . . ?
C55A C56A C57A 119.2(14) . . ?
C57A C56A H56A 120.4 . . ?
C52A C57A C56A 120.5(12) . . ?
C52A C57A H57A 119.7 . . ?
C56A C57A H57A 119.7 . . ?
H51G C51B H51H 109.5 . . ?
H51G C51B H51I 109.5 . . ?
H51H C51B H51I 109.5 . . ?
C52B C51B H51G 109.5 . . ?
C52B C51B H51H 109.5 . . ?
C52B C51B H51I 109.5 . . ?
C53B C52B C51B 113.2(12) . . ?
C57B C52B C51B 123.6(13) . . ?
C57B C52B C53B 121.7(12) . . ?
C52B C53B H53B 122.3 . . ?
C54B C53B C52B 115.3(14) . . ?
C54B C53B H53B 122.3 . . ?
C53B C54B H54B 118.1 . . ?
C53B C54B C55B 123.8(14) . . ?
C55B C54B H54B 118.1 . . ?
C54B C55B H55B 120.7 . . ?
C56B C55B C54B 118.7(11) . . ?
C56B C55B H55B 120.7 . . ?
C55B C56B H56B 120.8 . . ?
C55B C56B C57B 118.5(11) . . ?
C57B C56B H56B 120.8 . . ?
C52B C57B C56B 120.5(12) . . ?
C52B C57B H57B 119.7 . . ?
C56B C57B H57B 119.7 . . ?
H58A C58A H58B 109.5 . . ?
H58A C58A H58C 109.5 . . ?
H58B C58A H58C 109.5 . . ?
C59A C58A H58A 109.5 . . ?
C59A C58A H58B 109.5 . . ?
C59A C58A H58C 109.5 . . ?
C60A C59A C58A 114.6(12) . . ?
C64A C59A C58A 124.7(13) . . ?
C64A C59A C60A 120.6(12) . . ?
C59A C60A H60A 121.5 . . ?
C61A C60A C59A 116.9(14) . . ?
C61A C60A H60A 121.5 . . ?
C60A C61A H61A 118.2 . . ?
C60A C61A C62A 123.6(14) . . ?
C62A C61A H61A 118.2 . . ?
C61A C62A H62A 120.9 . . ?
C63A C62A C61A 118.3(12) . . ?
C63A C62A H62A 120.9 . . ?
C62A C63A H63A 120.6 . . ?
C62A C63A C64A 118.8(13) . . ?
C64A C63A H63A 120.6 . . ?
C59A C64A C63A 121.3(12) . . ?
C59A C64A H64A 119.4 . . ?
C63A C64A H64A 119.4 . . ?
H58D C58 H58E 109.5 . . ?
H58D C58 H58F 109.5 . . ?
H58E C58 H58F 109.5 . . ?
C59 C58 H58D 109.5 . . ?
C59 C58 H58E 109.5 . . ?
C59 C58 H58F 109.5 . . ?
C60 C59 C58 112.7(11) . . ?
C64 C59 C58 127.4(12) . . ?
C64 C59 C60 119.8(12) . . ?
C59 C60 H60 121.4 . . ?
C61 C60 C59 117.1(14) . . ?
C61 C60 H60 121.4 . . ?
C60 C61 H61 118.0 . . ?
C60 C61 C62 124.1(13) . . ?
C62 C61 H61 118.0 . . ?
C61 C62 H62 121.3 . . ?
C63 C62 C61 117.5(12) . . ?
C63 C62 H62 121.3 . . ?
C62 C63 H63 120.1 . . ?
C62 C63 C64 119.7(12) . . ?
C64 C63 H63 120.1 . . ?
C59 C64 C63 121.1(11) . . ?
C59 C64 H64 119.5 . . ?
C63 C64 H64 119.5 . . ?

