# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_EH020
_database_code_depnum_ccdc_archive 'CCDC 2068313'
loop_
_audit_author_name
_audit_author_address
'Alexander F. R. Kilpatrick'
;University of Leicester
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_EH020               
;
PROBLEM: Hirshfeld Test Diff for    C15      --C19      .        9.7 s.u.
RESPONSE: Some disorder in the Cp ring resulted in Level B  alerts  PLAT230 - Hirshfeld Test Diff for atoms atoms  C15, C18, C19 in the CIFcheck.  They have negligible effects on the gross structure or metrical data  of the core part of the molecular structure.
;
_vrf_PLAT910_EH020               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         28 Note
RESPONSE: 28 low-order reflections have been Omitted from  the final least-squares refinement.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 N Zr'
_chemical_formula_sum            'C21 H29 N Zr'
_chemical_formula_weight         386.67

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.1033(2)
_cell_length_b                   8.7177(2)
_cell_length_c                   13.9689(4)
_cell_angle_alpha                97.7980(10)
_cell_angle_beta                 92.9060(10)
_cell_angle_gamma                105.1750(10)
_cell_volume                     939.73(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    45278
_cell_measurement_theta_min      5.1
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             404
_exptl_crystal_preparation       'synthesis as described'
_exptl_crystal_recrystallization_method 
'grown by slow evapouration of a concentrated benzene solution at RT'

_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.585
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91640
_exptl_absorpt_correction_T_max  0.98710
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26527
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.143
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4290
_reflns_number_gt                3665
_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_cell_refinement       'COLLECT (Nonius)'
_computing_data_collection       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  
;
WinGX publication routines (Farrugia, 2012)and Olex2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;

_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)+(0.0481P)²+0.7353P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4290
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
Zr1 Zr 0.66141(3) 0.77176(3) 0.24577(2) 0.02814(10) Uani 1 1 d . . . . .
N1 N 0.5126(3) 0.5269(4) 0.2311(2) 0.0459(6) Uani 1 1 d . . . . .
C11 C 0.7411(4) 0.5344(4) 0.4338(2) 0.0376(6) Uani 1 1 d . . . . .
H9A H 0.6546 0.5410 0.4795 0.056 Uiso 1 1 calc R U . . .
H9B H 0.8409 0.5144 0.4672 0.056 Uiso 1 1 calc R U . . .
H9C H 0.6922 0.4463 0.3803 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8626(4) 1.1387(3) 0.4070(2) 0.0431(7) Uani 1 1 d . . . . .
H8A H 0.8721 1.1896 0.3484 0.065 Uiso 1 1 calc R U . . .
H8B H 0.9645 1.1897 0.4524 0.065 Uiso 1 1 calc R U . . .
H8C H 0.7599 1.1517 0.4376 0.065 Uiso 1 1 calc R U . . .
C14 C 1.0193(4) 1.0553(4) 0.1637(3) 0.0423(7) Uani 1 1 d . . . . .
H12A H 0.9611 1.0423 0.0987 0.063 Uiso 1 1 calc R U . . .
H12B H 1.1433 1.0761 0.1593 0.063 Uiso 1 1 calc R U . . .
H12C H 0.9957 1.1460 0.2049 0.063 Uiso 1 1 calc R U . . .
C19 C 0.5980(5) 0.9977(5) 0.1666(4) 0.0684(12) Uani 1 1 d . . . . .
H17 H 0.6970 1.0766 0.1544 0.082 Uiso 1 1 calc R U . . .
C3 C 0.7958(3) 0.6900(3) 0.39429(19) 0.0269(5) Uani 1 1 d . . . . .
C12 C 0.8784(4) 0.4543(3) 0.1961(2) 0.0369(6) Uani 1 1 d . . . . .
H10A H 0.7849 0.3961 0.2303 0.055 Uiso 1 1 calc R U . . .
H10B H 0.9854 0.4304 0.2164 0.055 Uiso 1 1 calc R U . . .
H10C H 0.8515 0.4205 0.1260 0.055 Uiso 1 1 calc R U . . .
C20 C 0.3808(5) 0.4883(6) 0.2935(3) 0.0673(11) Uani 1 1 d . . . . .
H18A H 0.4172 0.5547 0.3573 0.101 Uiso 1 1 calc R U . . .
H18B H 0.3574 0.3744 0.3004 0.101 Uiso 1 1 calc R U . . .
H18C H 0.2765 0.5090 0.2661 0.101 Uiso 1 1 calc R U . . .
C13 C 0.9504(4) 0.7106(4) 0.0493(2) 0.0382(7) Uani 1 1 d . . . . .
H11A H 0.8865 0.7697 0.0139 0.057 Uiso 1 1 calc R U . . .
H11B H 0.9044 0.5949 0.0267 0.057 Uiso 1 1 calc R U . . .
H11C H 1.0720 0.7442 0.0376 0.057 Uiso 1 1 calc R U . . .
C10 C 0.6724(4) 0.8650(4) 0.5206(2) 0.0423(7) Uani 1 1 d . . . . .
H0AA H 0.5825 0.7665 0.5246 0.063 Uiso 1 1 calc R U . . .
H0AB H 0.6200 0.9532 0.5154 0.063 Uiso 1 1 calc R U . . .
H0AC H 0.7527 0.8923 0.5791 0.063 Uiso 1 1 calc R U . . .
C7 C 0.9544(3) 0.9043(3) 0.2068(2) 0.0300(6) Uani 1 1 d . . . . .
C2 C 0.7674(4) 0.8387(3) 0.43283(19) 0.0302(6) Uani 1 1 d . . . . .
C4 C 0.9008(3) 0.7204(3) 0.31521(19) 0.0253(5) Uani 1 1 d . . . . .
C8 C 0.9378(3) 0.8903(3) 0.30761(19) 0.0278(5) Uani 1 1 d . . . . .
C6 C 0.9327(3) 0.7459(3) 0.1563(2) 0.0289(5) Uani 1 1 d . . . . .
C21 C 0.4726(5) 0.4288(5) 0.1391(3) 0.0625(10) Uani 1 1 d . . . . .
H19A H 0.3641 0.4380 0.1094 0.094 Uiso 1 1 calc R U . . .
H19B H 0.4614 0.3166 0.1469 0.094 Uiso 1 1 calc R U . . .
H19C H 0.5645 0.4639 0.0975 0.094 Uiso 1 1 calc R U . . .
C1 C 0.8489(4) 0.9628(3) 0.3803(2) 0.0309(6) Uani 1 1 d . . . . .
C5 C 0.8993(3) 0.6324(3) 0.22036(19) 0.0271(5) Uani 1 1 d . . . . .
C15 C 0.5124(5) 1.0038(5) 0.2505(3) 0.0553(9) Uani 1 1 d . . . . .
H13 H 0.5379 1.0893 0.3036 0.066 Uiso 1 1 calc R U . . .
C16 C 0.3838(5) 0.8620(6) 0.2418(4) 0.0715(12) Uani 1 1 d . . . . .
H14 H 0.3092 0.8314 0.2903 0.086 Uiso 1 1 calc R U . . .
C17 C 0.3791(6) 0.7717(6) 0.1529(4) 0.0807(15) Uani 1 1 d . . . . .
H15 H 0.3000 0.6706 0.1287 0.097 Uiso 1 1 calc R U . . .
C18 C 0.5150(8) 0.8575(8) 0.1035(3) 0.0869(19) Uani 1 1 d . . . . .
H16 H 0.5434 0.8254 0.0401 0.104 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
Zr1 N1 2.136(3) . ?
Zr1 C8 2.276(2) . ?
Zr1 C4 2.299(2) . ?
Zr1 C7 2.477(3) . ?
Zr1 C1 2.480(3) . ?
Zr1 C19 2.536(4) . ?
Zr1 C5 2.549(2) . ?
Zr1 C18 2.558(4) . ?
Zr1 C3 2.564(3) . ?
Zr1 C16 2.571(4) . ?
Zr1 C17 2.571(4) . ?
Zr1 C15 2.608(4) . ?
N1 C20 1.414(5) . ?
N1 C21 1.415(5) . ?
C11 C3 1.501(4) . ?
C11 H9A 0.9800 . ?
C11 H9B 0.9800 . ?
C11 H9C 0.9800 . ?
C9 C1 1.502(4) . ?
C9 H8A 0.9800 . ?
C9 H8B 0.9800 . ?
C9 H8C 0.9800 . ?
C14 C7 1.502(4) . ?
C14 H12A 0.9800 . ?
C14 H12B 0.9800 . ?
C14 H12C 0.9800 . ?
C19 C18 1.393(7) . ?
C19 C15 1.393(6) . ?
C19 H17 0.9500 . ?
C3 C2 1.415(4) . ?
C3 C4 1.439(4) . ?
C12 C5 1.506(4) . ?
C12 H10A 0.9800 . ?
C12 H10B 0.9800 . ?
C12 H10C 0.9800 . ?
C20 H18A 0.9800 . ?
C20 H18B 0.9800 . ?
C20 H18C 0.9800 . ?
C13 C6 1.506(4) . ?
C13 H11A 0.9800 . ?
C13 H11B 0.9800 . ?
C13 H11C 0.9800 . ?
C10 C2 1.504(4) . ?
C10 H0AA 0.9800 . ?
C10 H0AB 0.9800 . ?
C10 H0AC 0.9800 . ?
C7 C6 1.426(4) . ?
C7 C8 1.440(4) . ?
C2 C1 1.427(4) . ?
C4 C5 1.436(4) . ?
C4 C8 1.452(4) . ?
C8 C1 1.445(4) . ?
C6 C5 1.407(4) . ?
C21 H19A 0.9800 . ?
C21 H19B 0.9800 . ?
C21 H19C 0.9800 . ?
C15 C16 1.379(6) . ?
C15 H13 0.9500 . ?
C16 C17 1.370(7) . ?
C16 H14 0.9500 . ?
C17 C18 1.427(8) . ?
C17 H15 0.9500 . ?
C18 H16 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 C8 130.40(10) . . ?
N1 Zr1 C4 93.40(10) . . ?
C8 Zr1 C4 37.00(9) . . ?
N1 Zr1 C7 133.81(10) . . ?
C8 Zr1 C7 34.94(9) . . ?
C4 Zr1 C7 58.17(9) . . ?
N1 Zr1 C1 133.94(10) . . ?
C8 Zr1 C1 35.04(9) . . ?
C4 Zr1 C1 58.34(9) . . ?
C7 Zr1 C1 64.35(9) . . ?
N1 Zr1 C19 128.38(13) . . ?
C8 Zr1 C19 100.13(12) . . ?
C4 Zr1 C19 136.16(12) . . ?
C7 Zr1 C19 80.59(11) . . ?
C1 Zr1 C19 92.34(13) . . ?
N1 Zr1 C5 80.52(10) . . ?
C8 Zr1 C5 57.76(9) . . ?
C4 Zr1 C5 33.96(9) . . ?
C7 Zr1 C5 55.23(8) . . ?
C1 Zr1 C5 88.95(9) . . ?
C19 Zr1 C5 129.81(12) . . ?
N1 Zr1 C18 99.21(17) . . ?
C8 Zr1 C18 123.93(18) . . ?
C4 Zr1 C18 149.12(15) . . ?
C7 Zr1 C18 93.65(17) . . ?
C1 Zr1 C18 124.01(16) . . ?
C19 Zr1 C18 31.74(16) . . ?
C5 Zr1 C18 121.05(12) . . ?
N1 Zr1 C3 80.68(9) . . ?
C8 Zr1 C3 57.60(9) . . ?
C4 Zr1 C3 33.87(9) . . ?
C7 Zr1 C3 88.66(9) . . ?
C1 Zr1 C3 55.25(8) . . ?
C19 Zr1 C3 147.11(13) . . ?
C5 Zr1 C3 62.10(8) . . ?
C18 Zr1 C3 176.82(12) . . ?
N1 Zr1 C16 89.84(14) . . ?
C8 Zr1 C16 134.57(14) . . ?
C4 Zr1 C16 156.59(14) . . ?
C7 Zr1 C16 131.25(13) . . ?
C1 Zr1 C16 103.74(14) . . ?
C19 Zr1 C16 51.71(14) . . ?
C5 Zr1 C16 167.28(14) . . ?
C18 Zr1 C16 52.10(16) . . ?
C3 Zr1 C16 124.74(13) . . ?
N1 Zr1 C17 76.65(14) . . ?
C8 Zr1 C17 152.60(14) . . ?
C4 Zr1 C17 168.88(13) . . ?
C7 Zr1 C17 125.94(16) . . ?
C1 Zr1 C17 132.47(13) . . ?
C19 Zr1 C17 52.48(16) . . ?
C5 Zr1 C17 137.14(14) . . ?
C18 Zr1 C17 32.30(18) . . ?
C3 Zr1 C17 145.27(16) . . ?
C16 Zr1 C17 30.89(16) . . ?
N1 Zr1 C15 120.71(12) . . ?
C8 Zr1 C15 105.81(11) . . ?
C4 Zr1 C15 139.51(11) . . ?
C7 Zr1 C15 102.14(12) . . ?
C1 Zr1 C15 81.47(11) . . ?
C19 Zr1 C15 31.39(14) . . ?
C5 Zr1 C15 157.29(12) . . ?
C18 Zr1 C15 52.12(13) . . ?
C3 Zr1 C15 125.24(10) . . ?
C16 Zr1 C15 30.86(14) . . ?
C17 Zr1 C15 51.57(14) . . ?
C20 N1 C21 112.5(3) . . ?
C20 N1 Zr1 117.8(3) . . ?
C21 N1 Zr1 120.9(2) . . ?
C3 C11 H9A 109.5 . . ?
C3 C11 H9B 109.5 . . ?
H9A C11 H9B 109.5 . . ?
C3 C11 H9C 109.5 . . ?
H9A C11 H9C 109.5 . . ?
H9B C11 H9C 109.5 . . ?
C1 C9 H8A 109.5 . . ?
C1 C9 H8B 109.5 . . ?
H8A C9 H8B 109.5 . . ?
C1 C9 H8C 109.5 . . ?
H8A C9 H8C 109.5 . . ?
H8B C9 H8C 109.5 . . ?
C7 C14 H12A 109.5 . . ?
C7 C14 H12B 109.5 . . ?
H12A C14 H12B 109.5 . . ?
C7 C14 H12C 109.5 . . ?
H12A C14 H12C 109.5 . . ?
H12B C14 H12C 109.5 . . ?
C18 C19 C15 109.1(4) . . ?
C18 C19 Zr1 75.0(2) . . ?
C15 C19 Zr1 77.2(2) . . ?
C18 C19 H17 125.5 . . ?
C15 C19 H17 125.5 . . ?
Zr1 C19 H17 114.5 . . ?
C2 C3 C4 106.6(2) . . ?
C2 C3 C11 126.7(2) . . ?
C4 C3 C11 126.5(2) . . ?
C2 C3 Zr1 77.47(15) . . ?
C4 C3 Zr1 62.90(13) . . ?
C11 C3 Zr1 128.26(19) . . ?
C5 C12 H10A 109.5 . . ?
C5 C12 H10B 109.5 . . ?
H10A C12 H10B 109.5 . . ?
C5 C12 H10C 109.5 . . ?
H10A C12 H10C 109.5 . . ?
H10B C12 H10C 109.5 . . ?
N1 C20 H18A 109.5 . . ?
N1 C20 H18B 109.5 . . ?
H18A C20 H18B 109.5 . . ?
N1 C20 H18C 109.5 . . ?
H18A C20 H18C 109.5 . . ?
H18B C20 H18C 109.5 . . ?
C6 C13 H11A 109.5 . . ?
C6 C13 H11B 109.5 . . ?
H11A C13 H11B 109.5 . . ?
C6 C13 H11C 109.5 . . ?
H11A C13 H11C 109.5 . . ?
H11B C13 H11C 109.5 . . ?
C2 C10 H0AA 109.5 . . ?
C2 C10 H0AB 109.5 . . ?
H0AA C10 H0AB 109.5 . . ?
C2 C10 H0AC 109.5 . . ?
H0AA C10 H0AC 109.5 . . ?
H0AB C10 H0AC 109.5 . . ?
C6 C7 C8 106.9(2) . . ?
C6 C7 C14 124.3(3) . . ?
C8 C7 C14 127.6(3) . . ?
C6 C7 Zr1 79.73(15) . . ?
C8 C7 Zr1 64.90(14) . . ?
C14 C7 Zr1 130.1(2) . . ?
C3 C2 C1 110.9(2) . . ?
C3 C2 C10 124.7(3) . . ?
C1 C2 C10 124.3(3) . . ?
C3 C2 Zr1 71.08(14) . . ?
C1 C2 Zr1 67.52(14) . . ?
C10 C2 Zr1 131.06(19) . . ?
C5 C4 C3 133.1(2) . . ?
C5 C4 C8 108.4(2) . . ?
C3 C4 C8 108.5(2) . . ?
C5 C4 Zr1 82.60(15) . . ?
C3 C4 Zr1 83.23(15) . . ?
C8 C4 Zr1 70.65(14) . . ?
C7 C8 C1 132.4(2) . . ?
C7 C8 C4 107.1(2) . . ?
C1 C8 C4 107.4(2) . . ?
C7 C8 Zr1 80.16(15) . . ?
C1 C8 Zr1 80.21(15) . . ?
C4 C8 Zr1 72.34(14) . . ?
C5 C6 C7 110.7(2) . . ?
C5 C6 C13 126.1(2) . . ?
C7 C6 C13 123.2(2) . . ?
C5 C6 Zr1 71.15(14) . . ?
C7 C6 Zr1 68.01(14) . . ?
C13 C6 Zr1 129.49(18) . . ?
N1 C21 H19A 109.5 . . ?
N1 C21 H19B 109.5 . . ?
H19A C21 H19B 109.5 . . ?
N1 C21 H19C 109.5 . . ?
H19A C21 H19C 109.5 . . ?
H19B C21 H19C 109.5 . . ?
C2 C1 C8 106.6(2) . . ?
C2 C1 C9 125.8(3) . . ?
C8 C1 C9 126.9(3) . . ?
C2 C1 Zr1 80.37(16) . . ?
C8 C1 Zr1 64.75(14) . . ?
C9 C1 Zr1 127.15(19) . . ?
C6 C5 C4 106.8(2) . . ?
C6 C5 C12 126.9(2) . . ?
C4 C5 C12 126.2(2) . . ?
C6 C5 Zr1 77.37(15) . . ?
C4 C5 Zr1 63.43(13) . . ?
C12 C5 Zr1 126.99(18) . . ?
C16 C15 C19 106.9(4) . . ?
C16 C15 Zr1 73.1(2) . . ?
C19 C15 Zr1 71.4(2) . . ?
C16 C15 H13 126.5 . . ?
C19 C15 H13 126.5 . . ?
Zr1 C15 H13 120.8 . . ?
C17 C16 C15 110.2(4) . . ?
C17 C16 Zr1 74.6(2) . . ?
C15 C16 Zr1 76.1(2) . . ?
C17 C16 H14 124.9 . . ?
C15 C16 H14 124.9 . . ?
Zr1 C16 H14 116.3 . . ?
C16 C17 C18 107.3(4) . . ?
C16 C17 Zr1 74.5(2) . . ?
C18 C17 Zr1 73.3(2) . . ?
C16 C17 H15 126.4 . . ?
C18 C17 H15 126.4 . . ?
Zr1 C17 H15 117.8 . . ?
C19 C18 C17 106.4(4) . . ?
C19 C18 Zr1 73.3(2) . . ?
C17 C18 Zr1 74.4(2) . . ?
C19 C18 H16 126.8 . . ?
C17 C18 H16 126.8 . . ?
Zr1 C18 H16 117.7 . . ?

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
C4 C3 C2 C1 0.7(3) . . . . ?
C11 C3 C2 C1 175.6(3) . . . . ?
Zr1 C3 C2 C1 -55.7(2) . . . . ?
C4 C3 C2 C10 -176.2(3) . . . . ?
C11 C3 C2 C10 -1.3(4) . . . . ?
Zr1 C3 C2 C10 127.4(3) . . . . ?
C4 C3 C2 Zr1 56.42(17) . . . . ?
C11 C3 C2 Zr1 -128.7(3) . . . . ?
C2 C3 C4 C5 -139.2(3) . . . . ?
C11 C3 C4 C5 45.9(4) . . . . ?
Zr1 C3 C4 C5 -73.2(3) . . . . ?
C2 C3 C4 C8 1.0(3) . . . . ?
C11 C3 C4 C8 -173.9(3) . . . . ?
Zr1 C3 C4 C8 66.96(17) . . . . ?
C2 C3 C4 Zr1 -66.00(19) . . . . ?
C11 C3 C4 Zr1 119.1(3) . . . . ?
C6 C7 C8 C1 -136.6(3) . . . . ?
C14 C7 C8 C1 55.6(5) . . . . ?
Zr1 C7 C8 C1 -66.9(3) . . . . ?
C6 C7 C8 C4 -1.7(3) . . . . ?
C14 C7 C8 C4 -169.5(3) . . . . ?
Zr1 C7 C8 C4 67.93(17) . . . . ?
C6 C7 C8 Zr1 -69.64(19) . . . . ?
C14 C7 C8 Zr1 122.5(3) . . . . ?
C5 C4 C8 C7 1.5(3) . . . . ?
C3 C4 C8 C7 -149.0(2) . . . . ?
Zr1 C4 C8 C7 -73.39(18) . . . . ?
C5 C4 C8 C1 148.2(2) . . . . ?
C3 C4 C8 C1 -2.2(3) . . . . ?
Zr1 C4 C8 C1 73.34(18) . . . . ?
C5 C4 C8 Zr1 74.89(18) . . . . ?
C3 C4 C8 Zr1 -75.58(18) . . . . ?
C8 C7 C6 C5 1.3(3) . . . . ?
C14 C7 C6 C5 169.7(3) . . . . ?
Zr1 C7 C6 C5 -58.3(2) . . . . ?
C8 C7 C6 C13 -176.6(2) . . . . ?
C14 C7 C6 C13 -8.3(4) . . . . ?
Zr1 C7 C6 C13 123.7(2) . . . . ?
C8 C7 C6 Zr1 59.63(17) . . . . ?
C14 C7 C6 Zr1 -132.0(3) . . . . ?
C3 C2 C1 C8 -2.1(3) . . . . ?
C10 C2 C1 C8 174.8(3) . . . . ?
Zr1 C2 C1 C8 -59.85(17) . . . . ?
C3 C2 C1 C9 -173.0(3) . . . . ?
C10 C2 C1 C9 3.9(5) . . . . ?
Zr1 C2 C1 C9 129.2(3) . . . . ?
C3 C2 C1 Zr1 57.8(2) . . . . ?
C10 C2 C1 Zr1 -125.3(3) . . . . ?
C7 C8 C1 C2 137.4(3) . . . . ?
C4 C8 C1 C2 2.6(3) . . . . ?
Zr1 C8 C1 C2 70.50(19) . . . . ?
C7 C8 C1 C9 -51.9(4) . . . . ?
C4 C8 C1 C9 173.4(3) . . . . ?
Zr1 C8 C1 C9 -118.7(3) . . . . ?
C7 C8 C1 Zr1 66.9(3) . . . . ?
C4 C8 C1 Zr1 -67.88(17) . . . . ?
C7 C6 C5 C4 -0.4(3) . . . . ?
C13 C6 C5 C4 177.5(2) . . . . ?
Zr1 C6 C5 C4 -56.87(17) . . . . ?
C7 C6 C5 C12 -176.5(3) . . . . ?
C13 C6 C5 C12 1.4(4) . . . . ?
Zr1 C6 C5 C12 127.1(3) . . . . ?
C7 C6 C5 Zr1 56.48(19) . . . . ?
C13 C6 C5 Zr1 -125.6(3) . . . . ?
C3 C4 C5 C6 139.5(3) . . . . ?
C8 C4 C5 C6 -0.7(3) . . . . ?
Zr1 C4 C5 C6 66.02(19) . . . . ?
C3 C4 C5 C12 -44.4(4) . . . . ?
C8 C4 C5 C12 175.4(2) . . . . ?
Zr1 C4 C5 C12 -117.9(3) . . . . ?
C3 C4 C5 Zr1 73.5(3) . . . . ?
C8 C4 C5 Zr1 -66.71(17) . . . . ?
C18 C19 C15 C16 3.9(5) . . . . ?
Zr1 C19 C15 C16 -65.0(3) . . . . ?
C18 C19 C15 Zr1 68.9(3) . . . . ?
C19 C15 C16 C17 -3.6(5) . . . . ?
Zr1 C15 C16 C17 -67.5(3) . . . . ?
C19 C15 C16 Zr1 63.9(3) . . . . ?
C15 C16 C17 C18 1.9(5) . . . . ?
Zr1 C16 C17 C18 -66.6(3) . . . . ?
C15 C16 C17 Zr1 68.4(3) . . . . ?
C15 C19 C18 C17 -2.8(5) . . . . ?
Zr1 C19 C18 C17 67.6(3) . . . . ?
C15 C19 C18 Zr1 -70.4(3) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
Zr1 C17 C18 C19 -66.8(3) . . . . ?
C16 C17 C18 Zr1 67.4(3) . . . . ?

_refine_diff_density_max         0.882
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.080


####################################################################### 
# 
# 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_EH075
_database_code_depnum_ccdc_archive 'CCDC 2068315'
loop_
_audit_author_name
_audit_author_address
'Alexander F. R. Kilpatrick'
;University of Leicester
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_EH075               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         22 Note
RESPONSE: 22 low-order reflections have been ?Omitted' from  the final least-squares refinement. 
;
# Added during the CSD deposition process: Friday 05 March 2021 04:13 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H38 N2 Zr'
_chemical_formula_sum            'C38 H38 N2 Zr'
_chemical_formula_weight         613.92

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P c a n'
_space_group_name_Hall           '-P 2n 2c'

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

_cell_length_a                   7.33130(10)
_cell_length_b                   19.9253(3)
_cell_length_c                   20.0116(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2923.26(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3787
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.406
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97186
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6234
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         5.102
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3331
_reflns_number_gt                2367
_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       DENZO/SCALEPACK
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
Superflip (Platinus & Capuis, 2007)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0680P)²+2.0036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3331
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_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
Zr1 Zr 0.45980(4) 0.0000 0.2500 0.01807(14) Uani 1 2 d S T P . .
C10 C 0.6319(4) 0.04333(15) 0.07708(14) 0.0321(7) Uani 1 1 d . . . . .
H7A H 0.6193 0.0019 0.0511 0.048 Uiso 1 1 calc R U . . .
H7B H 0.5173 0.0685 0.0755 0.048 Uiso 1 1 calc R U . . .
H7C H 0.7303 0.0707 0.0582 0.048 Uiso 1 1 calc R U . . .
N1 N 0.2835(3) 0.08794(11) 0.26059(10) 0.0215(5) Uani 1 1 d . . . . .
C15 C 0.2375(4) 0.10360(14) 0.19353(13) 0.0251(6) Uani 1 1 d . . . . .
C26 C 0.2730(4) 0.11585(12) 0.37820(14) 0.0247(6) Uani 1 1 d . . . . .
H15 H 0.3463 0.0775 0.3869 0.030 Uiso 1 1 calc R U . . .
C20 C 0.2688(4) 0.16655(15) 0.16388(15) 0.0320(7) Uani 1 1 d . . . . .
H9 H 0.3166 0.2024 0.1898 0.038 Uiso 1 1 calc R U . . .
C25 C 0.2181(4) 0.15622(14) 0.43121(14) 0.0283(6) Uani 1 1 d . . . . .
H16 H 0.2572 0.1459 0.4753 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1642(5) 0.12447(19) 0.05747(17) 0.0460(9) Uani 1 1 d . . . . .
H11 H 0.1393 0.1316 0.0114 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7080(4) 0.14779(13) 0.19202(15) 0.0311(6) Uani 1 1 d . . . . .
H5A H 0.7296 0.1690 0.2355 0.047 Uiso 1 1 calc R U . . .
H5B H 0.8060 0.1602 0.1611 0.047 Uiso 1 1 calc R U . . .
H5C H 0.5908 0.1631 0.1741 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7543(3) 0.03544(13) 0.25872(12) 0.0211(6) Uani 1 1 d . . . . .
C14 C 0.7151(4) 0.10234(14) 0.37104(15) 0.0310(6) Uani 1 1 d . . . . .
H6A H 0.7332 0.1419 0.3427 0.047 Uiso 1 1 calc R U . . .
H6B H 0.6019 0.1074 0.3966 0.047 Uiso 1 1 calc R U . . .
H6C H 0.8181 0.0978 0.4019 0.047 Uiso 1 1 calc R U . . .
C2 C 0.6765(4) 0.02614(14) 0.14859(13) 0.0237(5) Uani 1 1 d . . . . .
C1 C 0.7043(4) 0.07294(13) 0.20022(13) 0.0235(6) Uani 1 1 d . . . . .
C7 C 0.7028(4) 0.04081(13) 0.32795(13) 0.0227(6) Uani 1 1 d . . . . .
C21 C 0.2224(4) 0.13033(12) 0.31201(13) 0.0218(5) Uani 1 1 d . . . . .
C17 C 0.1355(4) 0.06257(18) 0.08601(16) 0.0399(8) Uani 1 1 d . . . . .
H12 H 0.0930 0.0265 0.0591 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1677(4) 0.05192(15) 0.15381(14) 0.0301(6) Uani 1 1 d . . . . .
H13 H 0.1422 0.0094 0.1731 0.036 Uiso 1 1 calc R U . . .
C23 C 0.0497(4) 0.22519(14) 0.35567(15) 0.0256(6) Uani 1 1 d . . . . .
H18 H -0.0285 0.2623 0.3476 0.031 Uiso 1 1 calc R U . . .
C22 C 0.1052(4) 0.18535(13) 0.30261(14) 0.0244(6) Uani 1 1 d . . . . .
H19 H 0.0631 0.1955 0.2589 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1064(4) 0.21165(13) 0.42010(15) 0.0284(6) Uani 1 1 d . . . . .
H17 H 0.0698 0.2396 0.4562 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2300(5) 0.17629(18) 0.09690(16) 0.0418(8) Uani 1 1 d . . . . .
H10 H 0.2487 0.2193 0.0776 0.050 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
Zr1 N1 2.188(2) 3 ?
Zr1 N1 2.188(2) . ?
Zr1 C8 2.279(3) . ?
Zr1 C8 2.279(3) 3 ?
Zr1 C7 2.504(3) 3 ?
Zr1 C7 2.504(3) . ?
Zr1 C1 2.513(3) 3 ?
Zr1 C1 2.513(3) . ?
Zr1 C2 2.629(3) 3 ?
Zr1 C2 2.629(3) . ?
C10 C2 1.507(4) . ?
C10 H7A 0.9800 . ?
C10 H7B 0.9800 . ?
C10 H7C 0.9800 . ?
N1 C21 1.404(3) . ?
N1 C15 1.418(3) . ?
C15 C16 1.398(4) . ?
C15 C20 1.406(4) . ?
C26 C25 1.391(4) . ?
C26 C21 1.405(4) . ?
C26 H15 0.9500 . ?
C20 C19 1.384(4) . ?
C20 H9 0.9500 . ?
C25 C24 1.393(4) . ?
C25 H16 0.9500 . ?
C18 C17 1.375(5) . ?
C18 C19 1.386(5) . ?
C18 H11 0.9500 . ?
C9 C1 1.501(4) . ?
C9 H5A 0.9800 . ?
C9 H5B 0.9800 . ?
C9 H5C 0.9800 . ?
C8 C1 1.436(4) . ?
C8 C7 1.440(4) . ?
C8 C8 1.455(5) 3 ?
C14 C7 1.502(4) . ?
C14 H6A 0.9800 . ?
C14 H6B 0.9800 . ?
C14 H6C 0.9800 . ?
C2 C1 1.407(4) . ?
C2 C7 1.427(4) 3 ?
C7 C2 1.427(4) 3 ?
C21 C22 1.406(4) . ?
C17 C16 1.394(4) . ?
C17 H12 0.9500 . ?
C16 H13 0.9500 . ?
C23 C24 1.381(4) . ?
C23 C22 1.387(4) . ?
C23 H18 0.9500 . ?
C22 H19 0.9500 . ?
C24 H17 0.9500 . ?
C19 H10 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 N1 107.57(12) 3 . ?
N1 Zr1 C8 144.64(9) 3 . ?
N1 Zr1 C8 107.71(9) . . ?
N1 Zr1 C8 107.71(9) 3 3 ?
N1 Zr1 C8 144.65(9) . 3 ?
C8 Zr1 C8 37.24(13) . 3 ?
N1 Zr1 C7 95.73(8) 3 3 ?
N1 Zr1 C7 137.81(8) . 3 ?
C8 Zr1 C7 58.27(9) . 3 ?
C8 Zr1 C7 34.65(9) 3 3 ?
N1 Zr1 C7 137.81(8) 3 . ?
N1 Zr1 C7 95.73(8) . . ?
C8 Zr1 C7 34.65(9) . . ?
C8 Zr1 C7 58.27(9) 3 . ?
C7 Zr1 C7 89.28(12) 3 . ?
N1 Zr1 C1 89.80(8) 3 3 ?
N1 Zr1 C1 147.79(8) . 3 ?
C8 Zr1 C1 58.20(9) . 3 ?
C8 Zr1 C1 34.44(9) 3 3 ?
C7 Zr1 C1 63.36(9) 3 3 ?
C7 Zr1 C1 55.49(8) . 3 ?
N1 Zr1 C1 147.79(8) 3 . ?
N1 Zr1 C1 89.80(8) . . ?
C8 Zr1 C1 34.44(9) . . ?
C8 Zr1 C1 58.20(9) 3 . ?
C7 Zr1 C1 55.49(8) 3 . ?
C7 Zr1 C1 63.37(9) . . ?
C1 Zr1 C1 89.02(12) 3 . ?
N1 Zr1 C2 105.85(8) 3 3 ?
N1 Zr1 C2 116.16(8) . 3 ?
C8 Zr1 C2 55.23(9) . 3 ?
C8 Zr1 C2 54.90(9) 3 3 ?
C7 Zr1 C2 89.23(9) 3 3 ?
C7 Zr1 C2 32.17(9) . 3 ?
C1 Zr1 C2 31.65(9) 3 3 ?
C1 Zr1 C2 89.40(9) . 3 ?
N1 Zr1 C2 116.16(8) 3 . ?
N1 Zr1 C2 105.85(8) . . ?
C8 Zr1 C2 54.91(9) . . ?
C8 Zr1 C2 55.23(9) 3 . ?
C7 Zr1 C2 32.17(9) 3 . ?
C7 Zr1 C2 89.23(9) . . ?
C1 Zr1 C2 89.40(9) 3 . ?
C1 Zr1 C2 31.65(9) . . ?
C2 Zr1 C2 105.65(12) 3 . ?
C2 C10 H7A 109.5 . . ?
C2 C10 H7B 109.5 . . ?
H7A C10 H7B 109.5 . . ?
C2 C10 H7C 109.5 . . ?
H7A C10 H7C 109.5 . . ?
H7B C10 H7C 109.5 . . ?
C21 N1 C15 119.0(2) . . ?
C21 N1 Zr1 137.82(17) . . ?
C15 N1 Zr1 103.00(16) . . ?
C16 C15 C20 118.5(3) . . ?
C16 C15 N1 117.6(2) . . ?
C20 C15 N1 123.8(3) . . ?
C25 C26 C21 121.6(2) . . ?
C25 C26 H15 119.2 . . ?
C21 C26 H15 119.2 . . ?
C19 C20 C15 120.0(3) . . ?
C19 C20 H9 120.0 . . ?
C15 C20 H9 120.0 . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H16 119.8 . . ?
C24 C25 H16 119.8 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H11 120.5 . . ?
C19 C18 H11 120.5 . . ?
C1 C9 H5A 109.5 . . ?
C1 C9 H5B 109.5 . . ?
H5A C9 H5B 109.5 . . ?
C1 C9 H5C 109.5 . . ?
H5A C9 H5C 109.5 . . ?
H5B C9 H5C 109.5 . . ?
C1 C8 C7 132.7(2) . . ?
C1 C8 C8 108.0(3) . 3 ?
C7 C8 C8 107.6(3) . 3 ?
C1 C8 Zr1 81.76(15) . . ?
C7 C8 Zr1 81.26(15) . . ?
C8 C8 Zr1 71.38(6) 3 . ?
C7 C14 H6A 109.5 . . ?
C7 C14 H6B 109.5 . . ?
H6A C14 H6B 109.5 . . ?
C7 C14 H6C 109.5 . . ?
H6A C14 H6C 109.5 . . ?
H6B C14 H6C 109.5 . . ?
C1 C2 C7 111.0(2) . 3 ?
C1 C2 C10 125.3(3) . . ?
C7 C2 C10 123.6(3) 3 . ?
C1 C2 Zr1 69.62(15) . . ?
C7 C2 Zr1 69.06(14) 3 . ?
C10 C2 Zr1 130.30(18) . . ?
C2 C1 C8 106.9(2) . . ?
C2 C1 C9 125.5(2) . . ?
C8 C1 C9 127.0(2) . . ?
C2 C1 Zr1 78.73(16) . . ?
C8 C1 Zr1 63.80(14) . . ?
C9 C1 Zr1 129.12(19) . . ?
C2 C7 C8 106.4(2) 3 . ?
C2 C7 C14 125.6(2) 3 . ?
C8 C7 C14 126.7(2) . . ?
C2 C7 Zr1 78.77(15) 3 . ?
C8 C7 Zr1 64.09(14) . . ?
C14 C7 Zr1 131.73(19) . . ?
N1 C21 C26 118.9(2) . . ?
N1 C21 C22 124.5(2) . . ?
C26 C21 C22 116.6(2) . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H12 119.5 . . ?
C16 C17 H12 119.5 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H13 119.9 . . ?
C15 C16 H13 119.9 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H18 119.5 . . ?
C22 C23 H18 119.5 . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H19 119.2 . . ?
C21 C22 H19 119.2 . . ?
C23 C24 C25 118.7(3) . . ?
C23 C24 H17 120.6 . . ?
C25 C24 H17 120.6 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H10 119.4 . . ?
C18 C19 H10 119.4 . . ?

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
C21 N1 C15 C16 -132.0(3) . . . . ?
Zr1 N1 C15 C16 51.9(3) . . . . ?
C21 N1 C15 C20 52.2(4) . . . . ?
Zr1 N1 C15 C20 -123.9(2) . . . . ?
C16 C15 C20 C19 0.2(4) . . . . ?
N1 C15 C20 C19 176.0(3) . . . . ?
C21 C26 C25 C24 1.8(4) . . . . ?
C7 C2 C1 C8 1.4(3) 3 . . . ?
C10 C2 C1 C8 -176.5(2) . . . . ?
Zr1 C2 C1 C8 57.92(17) . . . . ?
C7 C2 C1 C9 173.0(2) 3 . . . ?
C10 C2 C1 C9 -4.8(4) . . . . ?
Zr1 C2 C1 C9 -130.4(3) . . . . ?
C7 C2 C1 Zr1 -56.56(19) 3 . . . ?
C10 C2 C1 Zr1 125.6(3) . . . . ?
C7 C8 C1 C2 -137.8(3) . . . . ?
C8 C8 C1 C2 -0.6(2) 3 . . . ?
Zr1 C8 C1 C2 -67.84(19) . . . . ?
C7 C8 C1 C9 50.7(4) . . . . ?
C8 C8 C1 C9 -172.1(2) 3 . . . ?
Zr1 C8 C1 C9 120.6(3) . . . . ?
C7 C8 C1 Zr1 -70.0(3) . . . . ?
C8 C8 C1 Zr1 67.27(8) 3 . . . ?
C1 C8 C7 C2 138.5(3) . . . 3 ?
C8 C8 C7 C2 1.2(2) 3 . . 3 ?
Zr1 C8 C7 C2 68.37(18) . . . 3 ?
C1 C8 C7 C14 -54.0(4) . . . . ?
C8 C8 C7 C14 168.7(2) 3 . . . ?
Zr1 C8 C7 C14 -124.1(3) . . . . ?
C1 C8 C7 Zr1 70.2(3) . . . . ?
C8 C8 C7 Zr1 -67.18(8) 3 . . . ?
C15 N1 C21 C26 -178.0(2) . . . . ?
Zr1 N1 C21 C26 -3.7(4) . . . . ?
C15 N1 C21 C22 5.2(4) . . . . ?
Zr1 N1 C21 C22 179.6(2) . . . . ?
C25 C26 C21 N1 179.4(2) . . . . ?
C25 C26 C21 C22 -3.6(4) . . . . ?
C19 C18 C17 C16 1.4(5) . . . . ?
C18 C17 C16 C15 -2.7(4) . . . . ?
C20 C15 C16 C17 1.9(4) . . . . ?
N1 C15 C16 C17 -174.2(3) . . . . ?
C24 C23 C22 C21 -0.7(4) . . . . ?
N1 C21 C22 C23 179.8(2) . . . . ?
C26 C21 C22 C23 3.0(4) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C26 C25 C24 C23 0.7(4) . . . . ?
C15 C20 C19 C18 -1.5(5) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?

_refine_diff_density_max         1.175
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.083


####################################################################### 
# 
# 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_eh055
_database_code_depnum_ccdc_archive 'CCDC 2068314'
loop_
_audit_author_name
_audit_author_address
'Alexander F. R. Kilpatrick'
;University of Leicester
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_audit_creation_date             2016-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;

_chemical_name_common            EH055
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H33 N Zr'
_chemical_formula_sum            'C31 H33 N Zr'
_chemical_formula_weight         510.80
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1146(2)
_cell_length_b                   10.0804(3)
_cell_length_c                   16.0623(5)
_cell_angle_alpha                82.184(2)
_cell_angle_beta                 75.5580(10)
_cell_angle_gamma                70.8260(10)
_cell_volume                     1199.67(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4576
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      5.097
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.87197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9011
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         5.161
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4022
_reflns_number_total             5456
_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       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       DENZO/SCALEPACK
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Platinus & Capuis, 2007)
;
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.033
_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)+(0.0613P)²+0.1925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1286
_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.a Me refined with riding coordinates:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C9(H9A,H9B,
 H9C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C24(H24), C16(H16), C19(H19), C15(H15), C25(H25), C31(H31),
 C21(H21), C28(H28), C30(H30), C22(H22), C23(H23), C29(H29), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.43048(4) 0.78470(4) 0.29899(2) 0.01832(12) Uani 1 1 d . . . . .
N1 N 0.5561(4) 0.8877(3) 0.17909(17) 0.0195(6) Uani 1 1 d . . . . .
C11 C 0.1799(5) 1.1667(4) 0.2566(2) 0.0277(8) Uani 1 1 d . . . . .
H11A H 0.1489 1.1590 0.2039 0.042 Uiso 1 1 calc R . . . .
H11B H 0.0893 1.2424 0.2874 0.042 Uiso 1 1 calc R . . . .
H11C H 0.2927 1.1851 0.2437 0.042 Uiso 1 1 calc R . . . .
C12 C 0.1619(5) 0.9056(4) 0.1321(2) 0.0284(9) Uani 1 1 d . . . . .
H12A H 0.1413 1.0050 0.1320 0.043 Uiso 1 1 calc R . . . .
H12B H 0.2741 0.8641 0.0939 0.043 Uiso 1 1 calc R . . . .
H12C H 0.0673 0.8895 0.1131 0.043 Uiso 1 1 calc R . . . .
C13 C 0.2177(5) 0.5782(4) 0.1966(3) 0.0327(9) Uani 1 1 d . . . . .
H13A H 0.2334 0.4918 0.2317 0.049 Uiso 1 1 calc R . . . .
H13B H 0.1140 0.5969 0.1730 0.049 Uiso 1 1 calc R . . . .
H13C H 0.3213 0.5701 0.1505 0.049 Uiso 1 1 calc R . . . .
C9 C 0.2211(6) 0.8213(5) 0.5228(2) 0.0346(10) Uani 1 1 d . . . . .
H9A H 0.2022 0.7308 0.5343 0.052 Uiso 1 1 calc R . . . .
H9B H 0.3362 0.8139 0.5322 0.052 Uiso 1 1 calc R . . . .
H9C H 0.1298 0.8872 0.5607 0.052 Uiso 1 1 calc R . . . .
C10 C 0.2854(5) 1.1007(4) 0.4382(3) 0.0326(9) Uani 1 1 d . . . . .
H10A H 0.3087 1.0573 0.4929 0.049 Uiso 1 1 calc R . . . .
H10B H 0.3903 1.1208 0.4036 0.049 Uiso 1 1 calc R . . . .
H10C H 0.1882 1.1867 0.4471 0.049 Uiso 1 1 calc R . . . .
C26 C 0.5928(5) 1.0163(4) 0.1791(2) 0.0205(7) Uani 1 1 d . . . . .
C27 C 0.6455(5) 1.0468(4) 0.2484(2) 0.0236(8) Uani 1 1 d . . . . .
H27 H 0.6578 0.9820 0.2953 0.028 Uiso 1 1 calc R . . . .
C24 C 0.6921(5) 0.6125(4) 0.0223(2) 0.0267(8) Uani 1 1 d . . . . .
H24 H 0.6547 0.5383 0.0140 0.032 Uiso 1 1 calc R . . . .
C20 C 0.6494(5) 0.8082(4) 0.1069(2) 0.0203(7) Uani 1 1 d . . . . .
C3 C 0.1936(5) 1.0312(4) 0.3109(2) 0.0222(8) Uani 1 1 d . . . . .
C16 C 0.6087(5) 0.5347(4) 0.3373(2) 0.0271(8) Uani 1 1 d . . . . .
H16 H 0.5623 0.4627 0.3347 0.032 Uiso 1 1 calc R . . . .
C4 C 0.1397(4) 0.9160(4) 0.2966(2) 0.0196(7) Uani 1 1 d . . . . .
C19 C 0.7656(5) 0.6915(4) 0.3009(3) 0.0308(9) Uani 1 1 d . . . . .
H19 H 0.8418 0.7413 0.2700 0.037 Uiso 1 1 calc R . . . .
C15 C 0.7269(5) 0.5844(4) 0.2702(2) 0.0273(8) Uani 1 1 d . . . . .
H15 H 0.7715 0.5515 0.2151 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2365(5) 1.0023(4) 0.3928(2) 0.0237(8) Uani 1 1 d . . . . .
C14 C 0.1802(6) 0.5465(5) 0.3956(3) 0.0365(10) Uani 1 1 d . . . . .
H14A H 0.1757 0.5594 0.4544 0.055 Uiso 1 1 calc R . . . .
H14B H 0.0759 0.5238 0.3926 0.055 Uiso 1 1 calc R . . . .
H14C H 0.2854 0.4712 0.3743 0.055 Uiso 1 1 calc R . . . .
C5 C 0.1666(4) 0.8402(4) 0.2220(2) 0.0193(7) Uani 1 1 d . . . . .
C8 C 0.1446(5) 0.8181(4) 0.3718(2) 0.0222(8) Uani 1 1 d . . . . .
C25 C 0.5960(5) 0.6984(4) 0.0893(2) 0.0254(8) Uani 1 1 d . . . . .
H25 H 0.4927 0.6828 0.1237 0.031 Uiso 1 1 calc R . . . .
C31 C 0.5741(5) 1.1166(4) 0.1103(2) 0.0245(8) Uani 1 1 d . . . . .
H31 H 0.5366 1.0991 0.0639 0.029 Uiso 1 1 calc R . . . .
C1 C 0.2136(5) 0.8715(4) 0.4307(2) 0.0239(8) Uani 1 1 d . . . . .
C7 C 0.1858(5) 0.6793(4) 0.3421(2) 0.0240(8) Uani 1 1 d . . . . .
C21 C 0.8054(5) 0.8281(4) 0.0508(2) 0.0249(8) Uani 1 1 d . . . . .
H21 H 0.8464 0.9000 0.0594 0.030 Uiso 1 1 calc R . . . .
C6 C 0.1931(5) 0.6982(4) 0.2512(2) 0.0228(8) Uani 1 1 d . . . . .
C28 C 0.6805(5) 1.1743(4) 0.2485(2) 0.0262(8) Uani 1 1 d . . . . .
H28 H 0.7142 1.1937 0.2956 0.031 Uiso 1 1 calc R . . . .
C30 C 0.6104(5) 1.2415(4) 0.1099(2) 0.0294(9) Uani 1 1 d . . . . .
H30 H 0.5983 1.3065 0.0631 0.035 Uiso 1 1 calc R . . . .
C22 C 0.8975(5) 0.7423(4) -0.0164(2) 0.0301(9) Uani 1 1 d . . . . .
H22 H 0.9999 0.7575 -0.0521 0.036 Uiso 1 1 calc R . . . .
C23 C 0.8419(5) 0.6345(4) -0.0322(2) 0.0291(9) Uani 1 1 d . . . . .
H23 H 0.9040 0.5783 -0.0784 0.035 Uiso 1 1 calc R . . . .
C29 C 0.6650(5) 1.2709(4) 0.1792(2) 0.0288(9) Uani 1 1 d . . . . .
H29 H 0.6906 1.3545 0.1786 0.035 Uiso 1 1 calc R . . . .
C18 C 0.6702(6) 0.7110(4) 0.3859(3) 0.0359(10) Uani 1 1 d . . . . .
H18 H 0.6703 0.7767 0.4213 0.043 Uiso 1 1 calc R . . . .
C17 C 0.5740(6) 0.6133(4) 0.4083(2) 0.0347(10) Uani 1 1 d . . . . .
H17 H 0.4997 0.6029 0.4615 0.042 Uiso 1 1 calc R . . . .


_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 2.236(3) . ?
Zr1 C3 2.591(4) . ?
Zr1 C16 2.540(4) . ?
Zr1 C4 2.302(3) . ?
Zr1 C19 2.576(4) . ?
Zr1 C15 2.567(4) . ?
Zr1 C5 2.603(3) . ?
Zr1 C8 2.259(3) . ?
Zr1 C1 2.444(3) . ?
Zr1 C7 2.460(3) . ?
Zr1 C18 2.532(4) . ?
Zr1 C17 2.509(4) . ?
N1 C26 1.422(4) . ?
N1 C20 1.406(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C3 1.505(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C5 1.508(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C6 1.522(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C1 1.507(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C2 1.507(5) . ?
C26 C27 1.391(5) . ?
C26 C31 1.395(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.404(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(5) . ?
C24 C23 1.374(5) . ?
C20 C25 1.398(5) . ?
C20 C21 1.415(5) . ?
C3 C4 1.431(5) . ?
C3 C2 1.412(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.409(5) . ?
C16 C17 1.397(5) . ?
C4 C5 1.441(5) . ?
C4 C8 1.451(5) . ?
C19 H19 0.9300 . ?
C19 C15 1.397(5) . ?
C19 C18 1.395(6) . ?
C15 H15 0.9300 . ?
C2 C1 1.425(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C7 1.497(5) . ?
C5 C6 1.407(5) . ?
C8 C1 1.449(5) . ?
C8 C7 1.447(5) . ?
C25 H25 0.9300 . ?
C31 H31 0.9300 . ?
C31 C30 1.384(5) . ?
C7 C6 1.435(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.377(5) . ?
C30 H30 0.9300 . ?
C30 C29 1.393(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(5) . ?
C23 H23 0.9300 . ?
C29 H29 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.406(6) . ?
C17 H17 0.9300 . ?

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 C3 82.31(11) . . ?
N1 Zr1 C16 115.78(12) . . ?
N1 Zr1 C4 96.11(12) . . ?
N1 Zr1 C19 76.94(12) . . ?
N1 Zr1 C15 84.20(12) . . ?
N1 Zr1 C5 83.78(11) . . ?
N1 Zr1 C8 133.19(12) . . ?
N1 Zr1 C1 134.27(12) . . ?
N1 Zr1 C7 136.46(11) . . ?
N1 Zr1 C18 102.76(13) . . ?
N1 Zr1 C17 129.69(13) . . ?
C3 Zr1 C5 61.13(11) . . ?
C16 Zr1 C3 161.39(12) . . ?
C16 Zr1 C19 52.74(13) . . ?
C16 Zr1 C15 32.02(12) . . ?
C16 Zr1 C5 122.31(12) . . ?
C4 Zr1 C3 33.35(11) . . ?
C4 Zr1 C16 139.43(13) . . ?
C4 Zr1 C19 167.28(12) . . ?
C4 Zr1 C15 159.78(12) . . ?
C4 Zr1 C5 33.47(11) . . ?
C4 Zr1 C1 58.55(12) . . ?
C4 Zr1 C7 58.56(13) . . ?
C4 Zr1 C18 145.26(12) . . ?
C4 Zr1 C17 133.47(13) . . ?
C19 Zr1 C3 134.07(12) . . ?
C19 Zr1 C5 152.06(12) . . ?
C15 Zr1 C3 163.16(12) . . ?
C15 Zr1 C19 31.54(12) . . ?
C15 Zr1 C5 127.20(11) . . ?
C8 Zr1 C3 57.47(12) . . ?
C8 Zr1 C16 107.35(13) . . ?
C8 Zr1 C4 37.09(12) . . ?
C8 Zr1 C19 148.20(13) . . ?
C8 Zr1 C15 138.91(13) . . ?
C8 Zr1 C5 57.36(12) . . ?
C8 Zr1 C1 35.61(12) . . ?
C8 Zr1 C7 35.38(12) . . ?
C8 Zr1 C18 117.54(14) . . ?
C8 Zr1 C17 96.64(13) . . ?
C1 Zr1 C3 55.20(12) . . ?
C1 Zr1 C16 106.25(13) . . ?
C1 Zr1 C19 119.12(12) . . ?
C1 Zr1 C15 133.07(12) . . ?
C1 Zr1 C5 88.82(11) . . ?
C1 Zr1 C7 65.46(12) . . ?
C1 Zr1 C18 87.83(13) . . ?
C1 Zr1 C17 80.21(13) . . ?
C7 Zr1 C3 88.75(12) . . ?
C7 Zr1 C16 80.88(13) . . ?
C7 Zr1 C19 133.42(13) . . ?
C7 Zr1 C15 108.01(12) . . ?
C7 Zr1 C5 55.15(12) . . ?
C7 Zr1 C18 118.06(14) . . ?
C7 Zr1 C17 86.53(14) . . ?
C18 Zr1 C3 121.06(12) . . ?
C18 Zr1 C16 53.31(13) . . ?
C18 Zr1 C19 31.70(13) . . ?
C18 Zr1 C15 52.73(12) . . ?
C18 Zr1 C5 173.21(13) . . ?
C17 Zr1 C3 132.47(12) . . ?
C17 Zr1 C16 32.11(13) . . ?
C17 Zr1 C19 52.78(14) . . ?
C17 Zr1 C15 52.88(13) . . ?
C17 Zr1 C5 141.00(13) . . ?
C17 Zr1 C18 32.39(14) . . ?
C26 N1 Zr1 122.3(2) . . ?
C20 N1 Zr1 119.6(2) . . ?
C20 N1 C26 115.5(3) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
C27 C26 N1 121.0(3) . . ?
C27 C26 C31 118.0(3) . . ?
C31 C26 N1 121.0(3) . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.8(3) . . ?
C28 C27 H27 119.6 . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.2(3) . . ?
N1 C20 C21 123.2(3) . . ?
C25 C20 N1 120.7(3) . . ?
C25 C20 C21 116.0(3) . . ?
C11 C3 Zr1 132.6(2) . . ?
C4 C3 Zr1 62.18(18) . . ?
C4 C3 C11 126.9(3) . . ?
C2 C3 Zr1 76.6(2) . . ?
C2 C3 C11 126.1(3) . . ?
C2 C3 C4 106.4(3) . . ?
Zr1 C16 H16 117.9 . . ?
C15 C16 Zr1 75.0(2) . . ?
C15 C16 H16 126.3 . . ?
C17 C16 Zr1 72.7(2) . . ?
C17 C16 H16 126.3 . . ?
C17 C16 C15 107.4(3) . . ?
C3 C4 Zr1 84.5(2) . . ?
C3 C4 C5 133.7(3) . . ?
C3 C4 C8 109.2(3) . . ?
C5 C4 Zr1 84.8(2) . . ?
C5 C4 C8 108.9(3) . . ?
C8 C4 Zr1 69.85(19) . . ?
Zr1 C19 H19 119.7 . . ?
C15 C19 Zr1 73.9(2) . . ?
C15 C19 H19 125.8 . . ?
C18 C19 Zr1 72.4(2) . . ?
C18 C19 H19 125.8 . . ?
C18 C19 C15 108.3(4) . . ?
Zr1 C15 H15 118.4 . . ?
C16 C15 Zr1 72.9(2) . . ?
C16 C15 H15 125.9 . . ?
C19 C15 Zr1 74.6(2) . . ?
C19 C15 C16 108.1(3) . . ?
C19 C15 H15 125.9 . . ?
C10 C2 Zr1 132.7(2) . . ?
C3 C2 Zr1 72.16(19) . . ?
C3 C2 C10 125.2(3) . . ?
C3 C2 C1 110.9(3) . . ?
C1 C2 Zr1 66.02(18) . . ?
C1 C2 C10 123.7(3) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
C12 C5 Zr1 126.4(2) . . ?
C4 C5 Zr1 61.75(18) . . ?
C4 C5 C12 125.2(3) . . ?
C6 C5 Zr1 76.8(2) . . ?
C6 C5 C12 128.6(3) . . ?
C6 C5 C4 106.3(3) . . ?
C4 C8 Zr1 73.06(19) . . ?
C1 C8 Zr1 79.2(2) . . ?
C1 C8 C4 106.5(3) . . ?
C7 C8 Zr1 79.9(2) . . ?
C7 C8 C4 107.2(3) . . ?
C7 C8 C1 132.6(3) . . ?
C24 C25 C20 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C20 C25 H25 119.0 . . ?
C26 C31 H31 119.4 . . ?
C30 C31 C26 121.2(3) . . ?
C30 C31 H31 119.4 . . ?
C9 C1 Zr1 128.7(3) . . ?
C2 C1 Zr1 81.8(2) . . ?
C2 C1 C9 123.8(3) . . ?
C2 C1 C8 106.8(3) . . ?
C8 C1 Zr1 65.22(18) . . ?
C8 C1 C9 128.0(3) . . ?
C14 C7 Zr1 128.9(3) . . ?
C8 C7 Zr1 64.71(18) . . ?
C8 C7 C14 127.6(3) . . ?
C6 C7 Zr1 81.6(2) . . ?
C6 C7 C14 124.8(3) . . ?
C6 C7 C8 106.2(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.5 . . ?
C13 C6 Zr1 131.2(2) . . ?
C5 C6 Zr1 72.20(19) . . ?
C5 C6 C13 125.9(3) . . ?
C5 C6 C7 111.3(3) . . ?
C7 C6 Zr1 66.13(18) . . ?
C7 C6 C13 122.8(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C31 C30 H30 119.7 . . ?
C31 C30 C29 120.5(4) . . ?
C29 C30 H30 119.7 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.8(4) . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 118.0(3) . . ?
C24 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
C28 C29 C30 119.0(3) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
Zr1 C18 H18 117.1 . . ?
C19 C18 Zr1 75.9(2) . . ?
C19 C18 H18 126.2 . . ?
C19 C18 C17 107.6(3) . . ?
C17 C18 Zr1 72.9(2) . . ?
C17 C18 H18 126.2 . . ?
Zr1 C17 H17 116.5 . . ?
C16 C17 Zr1 75.1(2) . . ?
C16 C17 C18 108.5(4) . . ?
C16 C17 H17 125.7 . . ?
C18 C17 Zr1 74.7(2) . . ?
C18 C17 H17 125.7 . . ?

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
Zr1 N1 C26 C27 35.1(4) . . . . ?
Zr1 N1 C26 C31 -143.8(3) . . . . ?
Zr1 N1 C20 C25 32.8(4) . . . . ?
Zr1 N1 C20 C21 -143.9(3) . . . . ?
Zr1 C3 C4 C5 -77.4(4) . . . . ?
Zr1 C3 C4 C8 66.4(2) . . . . ?
Zr1 C3 C2 C10 130.2(3) . . . . ?
Zr1 C3 C2 C1 -54.6(3) . . . . ?
Zr1 C16 C15 C19 66.9(3) . . . . ?
Zr1 C16 C17 C18 -67.8(3) . . . . ?
Zr1 C4 C5 C12 -116.4(3) . . . . ?
Zr1 C4 C5 C6 64.7(2) . . . . ?
Zr1 C4 C8 C1 72.8(2) . . . . ?
Zr1 C4 C8 C7 -73.4(2) . . . . ?
Zr1 C19 C15 C16 -65.8(3) . . . . ?
Zr1 C19 C18 C17 66.6(3) . . . . ?
Zr1 C2 C1 C9 131.6(4) . . . . ?
Zr1 C2 C1 C8 -60.9(2) . . . . ?
Zr1 C5 C6 C13 -128.4(3) . . . . ?
Zr1 C5 C6 C7 54.5(3) . . . . ?
Zr1 C8 C1 C9 -120.9(4) . . . . ?
Zr1 C8 C1 C2 72.3(2) . . . . ?
Zr1 C8 C7 C14 120.8(4) . . . . ?
Zr1 C8 C7 C6 -72.2(2) . . . . ?
Zr1 C7 C6 C13 124.8(3) . . . . ?
Zr1 C7 C6 C5 -57.9(3) . . . . ?
Zr1 C18 C17 C16 68.1(3) . . . . ?
N1 C26 C27 C28 -179.5(3) . . . . ?
N1 C26 C31 C30 -179.7(3) . . . . ?
N1 C20 C25 C24 -175.5(4) . . . . ?
N1 C20 C21 C22 176.4(4) . . . . ?
C11 C3 C4 Zr1 124.1(3) . . . . ?
C11 C3 C4 C5 46.8(6) . . . . ?
C11 C3 C4 C8 -169.4(3) . . . . ?
C11 C3 C2 Zr1 -133.4(4) . . . . ?
C11 C3 C2 C10 -3.2(6) . . . . ?
C11 C3 C2 C1 172.0(3) . . . . ?
C12 C5 C6 Zr1 126.3(4) . . . . ?
C12 C5 C6 C13 -2.1(6) . . . . ?
C12 C5 C6 C7 -179.2(3) . . . . ?
C10 C2 C1 Zr1 -126.6(3) . . . . ?
C10 C2 C1 C9 5.0(6) . . . . ?
C10 C2 C1 C8 172.5(3) . . . . ?
C26 N1 C20 C25 -165.1(3) . . . . ?
C26 N1 C20 C21 18.3(5) . . . . ?
C26 C27 C28 C29 -0.7(5) . . . . ?
C26 C31 C30 C29 -0.7(6) . . . . ?
C27 C26 C31 C30 1.4(5) . . . . ?
C27 C28 C29 C30 1.4(6) . . . . ?
C20 N1 C26 C27 -126.5(4) . . . . ?
C20 N1 C26 C31 54.6(4) . . . . ?
C20 C21 C22 C23 0.3(6) . . . . ?
C3 C4 C5 Zr1 77.2(4) . . . . ?
C3 C4 C5 C12 -39.2(6) . . . . ?
C3 C4 C5 C6 142.0(4) . . . . ?
C3 C4 C8 Zr1 -76.3(2) . . . . ?
C3 C4 C8 C1 -3.5(4) . . . . ?
C3 C4 C8 C7 -149.7(3) . . . . ?
C3 C2 C1 Zr1 58.1(3) . . . . ?
C3 C2 C1 C9 -170.3(3) . . . . ?
C3 C2 C1 C8 -2.8(4) . . . . ?
C4 C3 C2 Zr1 55.2(2) . . . . ?
C4 C3 C2 C10 -174.6(3) . . . . ?
C4 C3 C2 C1 0.7(4) . . . . ?
C4 C5 C6 Zr1 -54.9(2) . . . . ?
C4 C5 C6 C13 176.7(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C4 C8 C1 Zr1 -68.5(2) . . . . ?
C4 C8 C1 C9 170.6(3) . . . . ?
C4 C8 C1 C2 3.8(4) . . . . ?
C4 C8 C7 Zr1 68.6(2) . . . . ?
C4 C8 C7 C14 -170.6(4) . . . . ?
C4 C8 C7 C6 -3.6(4) . . . . ?
C19 C18 C17 Zr1 -68.6(3) . . . . ?
C19 C18 C17 C16 -0.4(4) . . . . ?
C15 C16 C17 Zr1 67.6(3) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C15 C19 C18 Zr1 -65.7(3) . . . . ?
C15 C19 C18 C17 0.9(4) . . . . ?
C2 C3 C4 Zr1 -64.6(2) . . . . ?
C2 C3 C4 C5 -142.0(4) . . . . ?
C2 C3 C4 C8 1.8(4) . . . . ?
C14 C7 C6 Zr1 -132.1(4) . . . . ?
C14 C7 C6 C13 -7.3(6) . . . . ?
C14 C7 C6 C5 170.0(3) . . . . ?
C5 C4 C8 Zr1 76.8(2) . . . . ?
C5 C4 C8 C1 149.7(3) . . . . ?
C5 C4 C8 C7 3.5(4) . . . . ?
C8 C4 C5 Zr1 -66.6(2) . . . . ?
C8 C4 C5 C12 176.9(3) . . . . ?
C8 C4 C5 C6 -1.9(4) . . . . ?
C8 C7 C6 Zr1 60.5(2) . . . . ?
C8 C7 C6 C13 -174.7(3) . . . . ?
C8 C7 C6 C5 2.6(4) . . . . ?
C25 C24 C23 C22 2.2(6) . . . . ?
C25 C20 C21 C22 -0.4(5) . . . . ?
C31 C26 C27 C28 -0.6(5) . . . . ?
C31 C30 C29 C28 -0.7(6) . . . . ?
C1 C8 C7 Zr1 -65.0(4) . . . . ?
C1 C8 C7 C14 55.9(6) . . . . ?
C1 C8 C7 C6 -137.2(4) . . . . ?
C7 C8 C1 Zr1 65.3(4) . . . . ?
C7 C8 C1 C9 -55.6(6) . . . . ?
C7 C8 C1 C2 137.6(4) . . . . ?
C21 C20 C25 C24 1.4(6) . . . . ?
C21 C22 C23 C24 -1.1(6) . . . . ?
C23 C24 C25 C20 -2.4(6) . . . . ?
C18 C19 C15 Zr1 64.7(3) . . . . ?
C18 C19 C15 C16 -1.0(4) . . . . ?
C17 C16 C15 Zr1 -66.1(3) . . . . ?
C17 C16 C15 C19 0.8(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_eh-082
_database_code_depnum_ccdc_archive 'CCDC 2068316'
loop_
_audit_author_name
_audit_author_address
'Alexander F. R. Kilpatrick'
;University of Leicester
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_audit_creation_date             2016-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H38 N2 O4 Zr'
_chemical_formula_sum            'C40 H38 N2 O4 Zr'
_chemical_formula_weight         701.94
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H50 N2 O4 Zr1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -0.1862 2.2449 '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/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                   9.02400(19)
_cell_length_b                   21.6398(5)
_cell_length_c                   18.9459(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.045(2)
_cell_angle_gamma                90
_cell_volume                     3679.13(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5678
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      76.0980
_cell_measurement_theta_min      4.6600
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.732
_exptl_absorpt_coefficient_mu    2.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -1 1 0.0525
6 1 -1 0.0525
0 -14 0 0.0151
-1 14 0 0.0164
4 -10 -2 0.0434
-4 10 2 0.0434
0 9 9 0.0183
0 -9 -9 0.0161

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.034
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.0000 -1.0000 1.0003 0.1553 0.7988 0.6264
6.0000 1.0000 -1.0003 -0.1553 -0.7988 -0.6264
-0.0000 -14.0000 -0.0000 0.1910 0.6355 -0.7439
-1.0000 14.0000 0.0001 -0.1541 -0.5129 0.8581
4.0000 -10.0000 -2.0002 0.1482 -0.0713 -0.9770
-4.0000 10.0000 2.0002 -0.1482 0.0713 0.9770
0.0000 9.0000 9.0000 -0.8403 -0.2533 0.4280
-0.0000 -9.0000 -9.0000 0.8403 0.2533 -0.4280

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14982
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         6.408
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5035
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  -6.00   1.00   20.00    --  -41.90 -19.00-120.00  114
  2  ω    -49.00  30.00   1.00   20.00    --  -41.90  37.00  60.00   79
  3  ω     89.00 178.00   1.00   97.50    --  111.00  45.00-180.00   89
  4  ω     41.00  99.00   1.00   97.50    --  111.00 -45.00  90.00   58
  5  ω     40.00  84.00   1.00   97.50    --  111.00 -45.00-150.00   44
  6  ω     87.00 178.00   1.00   97.50    --  111.00  30.00-120.00   91
  7  ω    100.00 177.00   1.00   97.50    --  111.00 111.00  60.00   77
  8  ω     40.00  84.00   1.00   97.50    --  111.00 -45.00   0.00   44
  9  ω     44.00  98.00   1.00   97.50    --  111.00 -45.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369068000
_diffrn_orient_matrix_UB_12      -0.0136398000
_diffrn_orient_matrix_UB_13      -0.0797283000
_diffrn_orient_matrix_UB_21      -0.1226933000
_diffrn_orient_matrix_UB_22      -0.0453960000
_diffrn_orient_matrix_UB_23      0.0172545000
_diffrn_orient_matrix_UB_31      -0.1141916000
_diffrn_orient_matrix_UB_32      0.0531362000
_diffrn_orient_matrix_UB_33      -0.0055784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6272
_reflns_number_total             7386
_reflns_odcompleteness_completeness 98.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    "'Superflip (Palatinus and Chapuis, 2007)"
_refine_diff_density_max         2.321
_refine_diff_density_min         -2.195
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0747
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+24.9216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.1992
_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.a Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
  C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C0AA C 0.0434(6) 0.0639(3) 0.0933(3) 0.0193(10) Uani 1 1 d . . . . .
C1AA C 0.1422(6) 0.1149(3) 0.1006(3) 0.0219(11) Uani 1 1 d . . . . .
C3 C 0.2866(6) 0.0959(3) 0.0890(3) 0.0233(11) Uani 1 1 d . . . . .
C4 C 0.2799(6) 0.0315(3) 0.0704(3) 0.0198(11) Uani 1 1 d . . . . .
C2AA C 0.3749(6) -0.0200(3) 0.0915(3) 0.0227(11) Uani 1 1 d . . . . .
C6 C 0.2779(7) -0.0707(3) 0.1000(3) 0.0242(11) Uani 1 1 d . . . . .
C7 C 0.1282(7) -0.0523(3) 0.0902(3) 0.0230(11) Uani 1 1 d . . . . .
C8 C 0.1262(6) 0.0124(3) 0.0710(2) 0.0180(10) Uani 1 1 d . . . . .
C9 C -0.1222(6) 0.0665(3) 0.0981(3) 0.0261(12) Uani 1 1 d . . . . .
H9A H -0.1646 0.0250 0.0911 0.039 Uiso 1 1 calc R . . . .
H9B H -0.1408 0.0820 0.1449 0.039 Uiso 1 1 calc R . . . .
H9C H -0.1687 0.0943 0.0613 0.039 Uiso 1 1 calc R . . . .
C10 C 0.0999(7) 0.1792(3) 0.1205(4) 0.0307(13) Uani 1 1 d . . . . .
H10A H -0.0070 0.1806 0.1256 0.046 Uiso 1 1 calc R . . . .
H10B H 0.1563 0.1907 0.1656 0.046 Uiso 1 1 calc R . . . .
H10C H 0.1227 0.2081 0.0834 0.046 Uiso 1 1 calc R . . . .
C11 C 0.4226(7) 0.1375(3) 0.0915(4) 0.0307(13) Uani 1 1 d . . . . .
H11A H 0.5094 0.1130 0.0816 0.046 Uiso 1 1 calc R . . . .
H11B H 0.4048 0.1702 0.0558 0.046 Uiso 1 1 calc R . . . .
H11C H 0.4413 0.1561 0.1388 0.046 Uiso 1 1 calc R . . . .
C12 C 0.5409(6) -0.0223(3) 0.0959(3) 0.0304(13) Uani 1 1 d . . . . .
H12A H 0.5796 0.0191 0.0880 0.046 Uiso 1 1 calc R . . . .
H12B H 0.5809 -0.0370 0.1431 0.046 Uiso 1 1 calc R . . . .
H12C H 0.5711 -0.0506 0.0596 0.046 Uiso 1 1 calc R . . . .
C13 C 0.3295(7) -0.1355(3) 0.1184(4) 0.0315(13) Uani 1 1 d . . . . .
H13A H 0.4386 -0.1370 0.1225 0.047 Uiso 1 1 calc R . . . .
H13B H 0.2946 -0.1477 0.1636 0.047 Uiso 1 1 calc R . . . .
H13C H 0.2887 -0.1639 0.0810 0.047 Uiso 1 1 calc R . . . .
C15 C -0.0054(7) -0.0940(3) 0.0935(3) 0.0289(13) Uani 1 1 d . . . . .
H15A H -0.0970 -0.0695 0.0847 0.043 Uiso 1 1 calc R . . . .
H15B H -0.0048 -0.1262 0.0572 0.043 Uiso 1 1 calc R . . . .
H15C H -0.0011 -0.1131 0.1405 0.043 Uiso 1 1 calc R . . . .
C16 C 0.3895(6) 0.0960(3) 0.2679(3) 0.0224(11) Uani 1 1 d . . . . .
C17 C 0.3872(6) 0.1823(3) 0.3469(3) 0.0215(11) Uani 1 1 d . . . . .
C18 C 0.3438(7) 0.2380(3) 0.3154(4) 0.0315(13) Uani 1 1 d . . . . .
H18 H 0.3645 0.2469 0.2684 0.038 Uiso 1 1 calc R . . . .
C19 C 0.2697(7) 0.2808(3) 0.3536(4) 0.0387(16) Uani 1 1 d . . . . .
H19 H 0.2377 0.3188 0.3322 0.046 Uiso 1 1 calc R . . . .
C20 C 0.2423(7) 0.2682(4) 0.4223(4) 0.0429(18) Uani 1 1 d . . . . .
H20 H 0.1936 0.2980 0.4486 0.051 Uiso 1 1 calc R . . . .
C21 C 0.2855(8) 0.2124(4) 0.4528(4) 0.0442(18) Uani 1 1 d . . . . .
H21 H 0.2636 0.2033 0.4996 0.053 Uiso 1 1 calc R . . . .
C22 C 0.3608(7) 0.1696(3) 0.4158(3) 0.0330(14) Uani 1 1 d . . . . .
H22 H 0.3938 0.1318 0.4375 0.040 Uiso 1 1 calc R . . . .
C23 C 0.6321(6) 0.1462(3) 0.3137(3) 0.0247(12) Uani 1 1 d . . . . .
C24 C 0.6942(7) 0.1954(3) 0.3534(4) 0.0322(14) Uani 1 1 d . . . . .
H24 H 0.6324 0.2229 0.3762 0.039 Uiso 1 1 calc R . . . .
C25 C 0.8480(7) 0.2040(3) 0.3595(4) 0.0350(15) Uani 1 1 d . . . . .
H25 H 0.8895 0.2377 0.3870 0.042 Uiso 1 1 calc R . . . .
C26 C 0.9404(7) 0.1664(4) 0.3280(4) 0.0372(15) Uani 1 1 d . . . . .
H26 H 1.0453 0.1721 0.3345 0.045 Uiso 1 1 calc R . . . .
C27 C 0.8769(7) 0.1192(4) 0.2857(5) 0.050(2) Uani 1 1 d . . . . .
H27 H 0.9388 0.0937 0.2605 0.060 Uiso 1 1 calc R . . . .
C28 C 0.7238(8) 0.1083(4) 0.2795(5) 0.049(2) Uani 1 1 d . . . . .
H28 H 0.6828 0.0747 0.2517 0.059 Uiso 1 1 calc R . . . .
C29 C 0.1053(6) -0.0540(3) 0.2663(3) 0.0197(10) Uani 1 1 d . . . . .
C30 C 0.1403(6) -0.1429(3) 0.3405(3) 0.0235(11) Uani 1 1 d . . . . .
C31 C 0.1903(8) -0.1315(4) 0.4101(4) 0.0405(16) Uani 1 1 d . . . . .
H31 H 0.1635 -0.0946 0.4328 0.049 Uiso 1 1 calc R . . . .
C32 C 0.2821(10) -0.1758(5) 0.4472(5) 0.057(2) Uani 1 1 d . . . . .
H32 H 0.3192 -0.1685 0.4952 0.069 Uiso 1 1 calc R . . . .
C33 C 0.3185(9) -0.2291(4) 0.4146(5) 0.057(3) Uani 1 1 d . . . . .
H33 H 0.3780 -0.2593 0.4407 0.069 Uiso 1 1 calc R . . . .
C34 C 0.2700(9) -0.2394(4) 0.3451(5) 0.050(2) Uani 1 1 d . . . . .
H34 H 0.2991 -0.2759 0.3222 0.060 Uiso 1 1 calc R . . . .
C35 C 0.1774(7) -0.1963(3) 0.3074(4) 0.0326(14) Uani 1 1 d . . . . .
H35 H 0.1404 -0.2039 0.2594 0.039 Uiso 1 1 calc R . . . .
C36 C -0.1170(6) -0.1072(3) 0.3059(3) 0.0211(11) Uani 1 1 d . . . . .
C37 C -0.1645(6) -0.1581(3) 0.3409(3) 0.0272(12) Uani 1 1 d . . . . .
H37 H -0.0936 -0.1870 0.3617 0.033 Uiso 1 1 calc R . . . .
C38 C -0.3153(7) -0.1676(3) 0.3461(4) 0.0323(14) Uani 1 1 d . . . . .
H38 H -0.3460 -0.2032 0.3701 0.039 Uiso 1 1 calc R . . . .
C39 C -0.4214(6) -0.1262(3) 0.3171(4) 0.0338(14) Uani 1 1 d . . . . .
H39 H -0.5242 -0.1322 0.3217 0.041 Uiso 1 1 calc R . . . .
C40 C -0.3735(8) -0.0764(4) 0.2816(5) 0.046(2) Uani 1 1 d . . . . .
H40 H -0.4449 -0.0478 0.2607 0.056 Uiso 1 1 calc R . . . .
C41 C -0.2232(8) -0.0662(3) 0.2750(4) 0.0395(16) Uani 1 1 d . . . . .
H41 H -0.1934 -0.0314 0.2494 0.047 Uiso 1 1 calc R . . . .
N1 N 0.4720(5) 0.1390(2) 0.3086(3) 0.0230(10) Uani 1 1 d . . . . .
N2 N 0.0393(5) -0.0992(2) 0.3024(2) 0.0203(9) Uani 1 1 d . . . . .
O1 O 0.2486(4) 0.09639(19) 0.2673(2) 0.0224(8) Uani 1 1 d . . . . .
O2 O 0.4503(4) 0.05623(18) 0.2307(2) 0.0192(8) Uani 1 1 d . . . . .
O3 O 0.2468(4) -0.05383(18) 0.2656(2) 0.0199(8) Uani 1 1 d . . . . .
O4 O 0.0294(4) -0.01230(17) 0.2306(2) 0.0199(8) Uani 1 1 d . . . . .
Zr1 Zr 0.22974(4) 0.02173(2) 0.18357(2) 0.01588(15) 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
C0AA C1AA 1.415(8) . ?
C0AA C8 1.430(8) . ?
C0AA C9 1.508(7) . ?
C0AA Zr1 2.446(5) . ?
C1AA C3 1.405(8) . ?
C1AA C10 1.502(8) . ?
C1AA Zr1 2.626(6) . ?
C3 C4 1.438(8) . ?
C3 C11 1.519(7) . ?
C3 Zr1 2.499(6) . ?
C4 C2AA 1.437(8) . ?
C4 C8 1.449(7) . ?
C4 Zr1 2.248(5) . ?
C2AA C6 1.422(8) . ?
C2AA C12 1.492(7) . ?
C2AA Zr1 2.460(5) . ?
C6 C7 1.402(8) . ?
C6 C13 1.507(8) . ?
C6 Zr1 2.614(6) . ?
C7 C8 1.446(8) . ?
C7 C15 1.512(8) . ?
C7 Zr1 2.488(5) . ?
C8 Zr1 2.246(5) . ?
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 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N1 1.376(8) . ?
C16 O1 1.270(7) . ?
C16 O2 1.273(7) . ?
C16 Zr1 2.594(6) . ?
C17 C18 1.382(9) . ?
C17 C22 1.378(9) . ?
C17 N1 1.452(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(12) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(12) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(8) . ?
C23 C28 1.374(9) . ?
C23 N1 1.446(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.349(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(10) . ?
C27 H27 0.9500 . ?
C27 C28 1.394(9) . ?
C28 H28 0.9500 . ?
C29 N2 1.366(8) . ?
C29 O3 1.278(6) . ?
C29 O4 1.281(7) . ?
C29 Zr1 2.601(6) . ?
C30 C31 1.372(9) . ?
C30 C35 1.372(9) . ?
C30 N2 1.451(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.405(10) . ?
C32 H32 0.9500 . ?
C32 C33 1.366(14) . ?
C33 H33 0.9500 . ?
C33 C34 1.362(14) . ?
C34 H34 0.9500 . ?
C34 C35 1.398(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.378(8) . ?
C36 C41 1.388(9) . ?
C36 N2 1.430(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.389(8) . ?
C38 H38 0.9500 . ?
C38 C39 1.383(9) . ?
C39 H39 0.9500 . ?
C39 C40 1.364(10) . ?
C40 H40 0.9500 . ?
C40 C41 1.393(10) . ?
C41 H41 0.9500 . ?
O1 Zr1 2.258(4) . ?
O2 Zr1 2.223(3) . ?
O3 Zr1 2.251(4) . ?
O4 Zr1 2.223(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1AA C0AA C8 107.0(5) . . ?
C1AA C0AA C9 125.7(5) . . ?
C1AA C0AA Zr1 80.9(3) . . ?
C8 C0AA C9 126.8(5) . . ?
C8 C0AA Zr1 64.7(3) . . ?
C9 C0AA Zr1 125.8(4) . . ?
C0AA C1AA C10 124.9(5) . . ?
C0AA C1AA Zr1 66.9(3) . . ?
C3 C1AA C0AA 110.0(5) . . ?
C3 C1AA C10 125.1(5) . . ?
C3 C1AA Zr1 69.2(3) . . ?
C10 C1AA Zr1 129.0(4) . . ?
C1AA C3 C4 107.8(5) . . ?
C1AA C3 C11 125.6(5) . . ?
C1AA C3 Zr1 79.1(3) . . ?
C4 C3 C11 126.5(5) . . ?
C4 C3 Zr1 63.0(3) . . ?
C11 C3 Zr1 125.7(4) . . ?
C3 C4 C8 106.8(5) . . ?
C3 C4 Zr1 82.2(3) . . ?
C2AA C4 C3 132.5(5) . . ?
C2AA C4 C8 108.6(5) . . ?
C2AA C4 Zr1 80.5(3) . . ?
C8 C4 Zr1 71.1(3) . . ?
C4 C2AA C12 127.4(6) . . ?
C4 C2AA Zr1 64.3(3) . . ?
C6 C2AA C4 105.9(5) . . ?
C6 C2AA C12 126.4(6) . . ?
C6 C2AA Zr1 79.8(3) . . ?
C12 C2AA Zr1 125.4(4) . . ?
C2AA C6 C13 124.4(5) . . ?
C2AA C6 Zr1 67.8(3) . . ?
C7 C6 C2AA 111.3(5) . . ?
C7 C6 C13 124.4(5) . . ?
C7 C6 Zr1 69.1(3) . . ?
C13 C6 Zr1 129.7(4) . . ?
C6 C7 C8 107.1(5) . . ?
C6 C7 C15 126.0(5) . . ?
C6 C7 Zr1 79.1(3) . . ?
C8 C7 C15 126.8(5) . . ?
C8 C7 Zr1 63.2(3) . . ?
C15 C7 Zr1 126.2(4) . . ?
C0AA C8 C4 108.1(5) . . ?
C0AA C8 C7 132.3(5) . . ?
C0AA C8 Zr1 80.1(3) . . ?
C4 C8 Zr1 71.3(3) . . ?
C7 C8 C4 107.0(5) . . ?
C7 C8 Zr1 81.6(3) . . ?
C0AA C9 H9A 109.5 . . ?
C0AA C9 H9B 109.5 . . ?
C0AA C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1AA C10 H10A 109.5 . . ?
C1AA C10 H10B 109.5 . . ?
C1AA 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 . . ?
C2AA C12 H12A 109.5 . . ?
C2AA C12 H12B 109.5 . . ?
C2AA C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 Zr1 175.4(4) . . ?
O1 C16 N1 118.9(5) . . ?
O1 C16 O2 119.2(5) . . ?
O1 C16 Zr1 60.5(3) . . ?
O2 C16 N1 121.9(5) . . ?
O2 C16 Zr1 58.9(3) . . ?
C18 C17 N1 119.1(5) . . ?
C22 C17 C18 120.9(6) . . ?
C22 C17 N1 119.8(5) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.1(7) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(7) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(6) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(7) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 119.3(7) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 N1 117.5(5) . . ?
C28 C23 C24 119.0(6) . . ?
C28 C23 N1 123.5(5) . . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.3(6) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 118.7 . . ?
C26 C25 C24 122.7(6) . . ?
C26 C25 H25 118.7 . . ?
C25 C26 H26 121.2 . . ?
C25 C26 C27 117.6(6) . . ?
C27 C26 H26 121.2 . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C28 121.3(7) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 C27 120.0(6) . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
N2 C29 Zr1 172.4(4) . . ?
O3 C29 N2 119.7(5) . . ?
O3 C29 O4 118.2(5) . . ?
O3 C29 Zr1 59.9(3) . . ?
O4 C29 N2 122.1(5) . . ?
O4 C29 Zr1 58.7(3) . . ?
C31 C30 C35 121.3(6) . . ?
C31 C30 N2 119.2(6) . . ?
C35 C30 N2 119.5(6) . . ?
C30 C31 H31 120.8 . . ?
C30 C31 C32 118.3(8) . . ?
C32 C31 H31 120.8 . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(8) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.5(7) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 119.9(8) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 119.4(7) . . ?
C30 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C37 C36 C41 118.5(5) . . ?
C37 C36 N2 118.5(5) . . ?
C41 C36 N2 122.9(5) . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.6(5) . . ?
C38 C37 H37 119.7 . . ?
C37 C38 H38 119.4 . . ?
C39 C38 C37 121.2(6) . . ?
C39 C38 H38 119.4 . . ?
C38 C39 H39 121.1 . . ?
C40 C39 C38 117.7(6) . . ?
C40 C39 H39 121.1 . . ?
C39 C40 H40 119.0 . . ?
C39 C40 C41 122.1(6) . . ?
C41 C40 H40 119.0 . . ?
C36 C41 C40 119.8(6) . . ?
C36 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?
C16 N1 C17 115.7(4) . . ?
C16 N1 C23 126.0(5) . . ?
C23 N1 C17 118.2(4) . . ?
C29 N2 C30 115.6(4) . . ?
C29 N2 C36 126.5(5) . . ?
C36 N2 C30 118.0(5) . . ?
C16 O1 Zr1 90.2(3) . . ?
C16 O2 Zr1 91.7(3) . . ?
C29 O3 Zr1 90.7(3) . . ?
C29 O4 Zr1 91.9(3) . . ?
C0AA Zr1 C3 55.69(17) . . ?
C0AA Zr1 C2AA 91.10(18) . . ?
C0AA Zr1 C7 64.44(19) . . ?
C0AA Zr1 C16 119.73(18) . . ?
C0AA Zr1 C29 110.36(17) . . ?
C3 Zr1 C16 84.30(18) . . ?
C3 Zr1 C29 166.04(17) . . ?
C4 Zr1 C0AA 59.35(18) . . ?
C4 Zr1 C3 34.7(2) . . ?
C4 Zr1 C2AA 35.2(2) . . ?
C4 Zr1 C7 58.58(19) . . ?
C4 Zr1 C16 111.99(19) . . ?
C4 Zr1 C29 140.96(19) . . ?
C4 Zr1 O1 126.52(18) . . ?
C4 Zr1 O3 136.17(18) . . ?
C2AA Zr1 C3 64.1(2) . . ?
C2AA Zr1 C7 56.19(19) . . ?
C2AA Zr1 C16 111.18(18) . . ?
C2AA Zr1 C29 119.42(19) . . ?
C7 Zr1 C3 89.54(19) . . ?
C7 Zr1 C16 167.36(18) . . ?
C7 Zr1 C29 82.68(17) . . ?
C8 Zr1 C0AA 35.17(19) . . ?
C8 Zr1 C3 58.19(19) . . ?
C8 Zr1 C4 37.61(19) . . ?
C8 Zr1 C2AA 59.54(18) . . ?
C8 Zr1 C7 35.11(19) . . ?
C8 Zr1 C16 142.10(19) . . ?
C8 Zr1 C29 110.65(18) . . ?
C8 Zr1 O1 136.43(18) . . ?
C8 Zr1 O3 125.61(17) . . ?
C16 Zr1 C29 105.46(17) . . ?
O1 Zr1 C0AA 102.70(17) . . ?
O1 Zr1 C3 92.19(18) . . ?
O1 Zr1 C2AA 138.96(17) . . ?
O1 Zr1 C7 162.70(17) . . ?
O1 Zr1 C16 29.32(16) . . ?
O1 Zr1 C29 91.89(16) . . ?
O2 Zr1 C0AA 132.54(16) . . ?
O2 Zr1 C3 80.20(16) . . ?
O2 Zr1 C4 95.16(17) . . ?
O2 Zr1 C2AA 83.53(16) . . ?
O2 Zr1 C7 138.50(17) . . ?
O2 Zr1 C8 132.62(17) . . ?
O2 Zr1 C16 29.36(16) . . ?
O2 Zr1 C29 113.22(15) . . ?
O2 Zr1 O1 58.62(13) . . ?
O2 Zr1 O3 88.46(14) . . ?
O3 Zr1 C0AA 138.29(16) . . ?
O3 Zr1 C3 163.32(16) . . ?
O3 Zr1 C2AA 102.71(17) . . ?
O3 Zr1 C7 90.95(17) . . ?
O3 Zr1 C16 91.82(16) . . ?
O3 Zr1 C29 29.42(15) . . ?
O3 Zr1 O1 92.29(15) . . ?
O4 Zr1 C0AA 82.87(15) . . ?
O4 Zr1 C3 137.47(16) . . ?
O4 Zr1 C4 131.85(17) . . ?
O4 Zr1 C2AA 132.70(17) . . ?
O4 Zr1 C7 79.46(17) . . ?
O4 Zr1 C8 94.36(17) . . ?
O4 Zr1 C16 112.42(16) . . ?
O4 Zr1 C29 29.49(15) . . ?
O4 Zr1 O1 87.71(14) . . ?
O4 Zr1 O2 132.98(14) . . ?
O4 Zr1 O3 58.80(13) . . ?

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
C0AA C1AA C3 C4 2.7(6) . . . . ?
C0AA C1AA C3 C11 179.4(5) . . . . ?
C0AA C1AA C3 Zr1 -54.2(4) . . . . ?
C1AA C0AA C8 C4 4.5(6) . . . . ?
C1AA C0AA C8 C7 139.9(6) . . . . ?
C1AA C0AA C8 Zr1 70.9(4) . . . . ?
C1AA C3 C4 C2AA -136.7(6) . . . . ?
C1AA C3 C4 C8 0.2(6) . . . . ?
C1AA C3 C4 Zr1 -67.3(4) . . . . ?
C3 C4 C2AA C6 140.2(6) . . . . ?
C3 C4 C2AA C12 -46.0(9) . . . . ?
C3 C4 C2AA Zr1 70.2(6) . . . . ?
C3 C4 C8 C0AA -2.9(6) . . . . ?
C3 C4 C8 C7 -150.1(5) . . . . ?
C3 C4 C8 Zr1 -75.3(4) . . . . ?
C4 C2AA C6 C7 -4.2(6) . . . . ?
C4 C2AA C6 C13 176.7(5) . . . . ?
C4 C2AA C6 Zr1 -59.4(3) . . . . ?
C2AA C4 C8 C0AA 145.0(5) . . . . ?
C2AA C4 C8 C7 -2.2(6) . . . . ?
C2AA C4 C8 Zr1 72.6(4) . . . . ?
C2AA C6 C7 C8 2.9(6) . . . . ?
C2AA C6 C7 C15 178.4(5) . . . . ?
C2AA C6 C7 Zr1 -54.5(4) . . . . ?
C6 C7 C8 C0AA -136.2(6) . . . . ?
C6 C7 C8 C4 -0.4(6) . . . . ?
C6 C7 C8 Zr1 -67.9(4) . . . . ?
C8 C0AA C1AA C3 -4.5(6) . . . . ?
C8 C0AA C1AA C10 177.6(5) . . . . ?
C8 C0AA C1AA Zr1 -60.0(3) . . . . ?
C8 C4 C2AA C6 3.8(6) . . . . ?
C8 C4 C2AA C12 177.6(5) . . . . ?
C8 C4 C2AA Zr1 -66.2(3) . . . . ?
C9 C0AA C1AA C3 -176.6(5) . . . . ?
C9 C0AA C1AA C10 5.5(9) . . . . ?
C9 C0AA C1AA Zr1 127.9(6) . . . . ?
C9 C0AA C8 C4 176.6(5) . . . . ?
C9 C0AA C8 C7 -48.0(9) . . . . ?
C9 C0AA C8 Zr1 -117.0(5) . . . . ?
C10 C1AA C3 C4 -179.4(5) . . . . ?
C10 C1AA C3 C11 -2.7(9) . . . . ?
C10 C1AA C3 Zr1 123.7(6) . . . . ?
C11 C3 C4 C2AA 46.6(9) . . . . ?
C11 C3 C4 C8 -176.5(5) . . . . ?
C11 C3 C4 Zr1 116.0(6) . . . . ?
C12 C2AA C6 C7 -178.1(5) . . . . ?
C12 C2AA C6 C13 2.8(9) . . . . ?
C12 C2AA C6 Zr1 126.7(6) . . . . ?
C13 C6 C7 C8 -178.0(5) . . . . ?
C13 C6 C7 C15 -2.5(9) . . . . ?
C13 C6 C7 Zr1 124.6(6) . . . . ?
C15 C7 C8 C0AA 48.3(9) . . . . ?
C15 C7 C8 C4 -175.9(5) . . . . ?
C15 C7 C8 Zr1 116.7(5) . . . . ?
C17 C18 C19 C20 1.2(10) . . . . ?
C18 C17 C22 C21 2.1(9) . . . . ?
C18 C17 N1 C16 -91.8(7) . . . . ?
C18 C17 N1 C23 85.6(7) . . . . ?
C18 C19 C20 C21 -1.5(11) . . . . ?
C19 C20 C21 C22 2.1(11) . . . . ?
C20 C21 C22 C17 -2.4(11) . . . . ?
C22 C17 C18 C19 -1.5(9) . . . . ?
C22 C17 N1 C16 93.0(6) . . . . ?
C22 C17 N1 C23 -89.5(7) . . . . ?
C23 C24 C25 C26 0.3(12) . . . . ?
C24 C23 C28 C27 0.7(13) . . . . ?
C24 C23 N1 C16 175.2(6) . . . . ?
C24 C23 N1 C17 -2.0(8) . . . . ?
C24 C25 C26 C27 2.7(12) . . . . ?
C25 C26 C27 C28 -4.0(14) . . . . ?
C26 C27 C28 C23 2.4(15) . . . . ?
C28 C23 C24 C25 -2.0(11) . . . . ?
C28 C23 N1 C16 -2.5(10) . . . . ?
C28 C23 N1 C17 -179.7(7) . . . . ?
C30 C31 C32 C33 -1.0(13) . . . . ?
C31 C30 C35 C34 -1.2(10) . . . . ?
C31 C30 N2 C29 91.9(7) . . . . ?
C31 C30 N2 C36 -88.1(7) . . . . ?
C31 C32 C33 C34 2.0(14) . . . . ?
C32 C33 C34 C35 -2.6(12) . . . . ?
C33 C34 C35 C30 2.2(11) . . . . ?
C35 C30 C31 C32 0.6(11) . . . . ?
C35 C30 N2 C29 -91.7(7) . . . . ?
C35 C30 N2 C36 88.4(7) . . . . ?
C36 C37 C38 C39 -0.6(11) . . . . ?
C37 C36 C41 C40 1.8(11) . . . . ?
C37 C36 N2 C29 175.5(6) . . . . ?
C37 C36 N2 C30 -4.5(8) . . . . ?
C37 C38 C39 C40 1.6(12) . . . . ?
C38 C39 C40 C41 -0.9(13) . . . . ?
C39 C40 C41 C36 -0.8(14) . . . . ?
C41 C36 C37 C38 -1.1(10) . . . . ?
C41 C36 N2 C29 -3.7(10) . . . . ?
C41 C36 N2 C30 176.2(6) . . . . ?
N1 C16 O1 Zr1 174.8(5) . . . . ?
N1 C16 O2 Zr1 -174.7(5) . . . . ?
N1 C17 C18 C19 -176.6(5) . . . . ?
N1 C17 C22 C21 177.2(6) . . . . ?
N1 C23 C24 C25 -179.8(6) . . . . ?
N1 C23 C28 C27 178.4(8) . . . . ?
N2 C29 O3 Zr1 171.2(5) . . . . ?
N2 C29 O4 Zr1 -171.1(5) . . . . ?
N2 C30 C31 C32 176.9(7) . . . . ?
N2 C30 C35 C34 -177.5(6) . . . . ?
N2 C36 C37 C38 179.6(6) . . . . ?
N2 C36 C41 C40 -179.0(7) . . . . ?
O1 C16 N1 C17 -0.9(8) . . . . ?
O1 C16 N1 C23 -178.1(5) . . . . ?
O1 C16 O2 Zr1 4.9(5) . . . . ?
O2 C16 N1 C17 178.7(5) . . . . ?
O2 C16 N1 C23 1.5(9) . . . . ?
O2 C16 O1 Zr1 -4.9(5) . . . . ?
O3 C29 N2 C30 2.6(7) . . . . ?
O3 C29 N2 C36 -177.4(5) . . . . ?
O3 C29 O4 Zr1 6.6(5) . . . . ?
O4 C29 N2 C30 -179.8(5) . . . . ?
O4 C29 N2 C36 0.2(9) . . . . ?
O4 C29 O3 Zr1 -6.5(5) . . . . ?
Zr1 C0AA C1AA C3 55.5(4) . . . . ?
Zr1 C0AA C1AA C10 -122.4(6) . . . . ?
Zr1 C0AA C8 C4 -66.4(3) . . . . ?
Zr1 C0AA C8 C7 69.0(5) . . . . ?
Zr1 C1AA C3 C4 56.9(4) . . . . ?
Zr1 C1AA C3 C11 -126.4(6) . . . . ?
Zr1 C3 C4 C2AA -69.4(6) . . . . ?
Zr1 C3 C4 C8 67.5(3) . . . . ?
Zr1 C4 C2AA C6 70.1(4) . . . . ?
Zr1 C4 C2AA C12 -116.2(6) . . . . ?
Zr1 C4 C8 C0AA 72.4(4) . . . . ?
Zr1 C4 C8 C7 -74.7(3) . . . . ?
Zr1 C2AA C6 C7 55.2(4) . . . . ?
Zr1 C2AA C6 C13 -123.9(6) . . . . ?
Zr1 C6 C7 C8 57.4(3) . . . . ?
Zr1 C6 C7 C15 -127.1(6) . . . . ?
Zr1 C7 C8 C0AA -68.4(5) . . . . ?
Zr1 C7 C8 C4 67.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.698 0.000 0.500 252.0 68.9 ?
2 -0.102 0.500 0.000 252.0 68.9 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.796

#===END

