#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:03:39 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293760 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571809.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571809
loop_
_publ_author_name
'Nuñez Bahena, Erick'
'Hosseini, Kimia'
'Curto, Sheila Galván'
'Schafer, Laurel L.'
_publ_section_title
;
 Understanding mechanism driven regioselectivity in zirconium-catalysed
 hydroaminoalkylation: homoallylic amines from conjugated dienes.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10571
_journal_page_last               10576
_journal_paper_doi               10.1039/d4sc00636d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C42 H59 N5 O2 Zr'
_chemical_formula_sum            'C42 H59 N5 O2 Zr'
_chemical_formula_weight         757.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-05-25 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                79.490(2)
_cell_angle_beta                 72.182(2)
_cell_angle_gamma                67.933(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6003(6)
_cell_length_b                   13.7655(7)
_cell_length_c                   15.6971(8)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.18
_cell_volume                     2014.97(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            59696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_min         1.601
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7222
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.9680.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         12351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0303P)²+0.7671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10307
_reflns_number_total             12351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00636d2.cif
_cod_data_source_block           ls926
_cod_depositor_comments
'Adding full bibliography for 1571809--1571811.cif.'
_cod_database_code               1571809
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1), C34(H34), C31(H31), C37(H37), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C26(H26A,H26B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C23(H23), C11(H11), C17(H17), C9(H9), C19(H19), C20(H20),
 C7(H7), C8(H8), C21(H21), C22(H22), C14(H14), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C36(H36A,H36B,H36C), C42(H42A,H42B,H42C), C38(H38A,H38B,
 H38C), C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C29(H29A,
 H29B,H29C), C41(H41A,H41B,H41C), C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.43244(2) 0.79138(2) 0.71691(2) 0.00860(4) Uani 1 1 d . . . . .
O2 O 0.27304(10) 0.95070(7) 0.73398(7) 0.01280(19) Uani 1 1 d . . . . .
O1 O 0.64059(10) 0.66112(7) 0.70232(7) 0.01183(19) Uani 1 1 d . . . . .
N3 N 0.21826(12) 0.81340(9) 0.80290(8) 0.0116(2) Uani 1 1 d . . . . .
N2 N 0.44470(12) 0.63132(9) 0.77271(8) 0.0108(2) Uani 1 1 d . . . . .
N1 N 0.43175(12) 0.79183(9) 0.58153(8) 0.0111(2) Uani 1 1 d . . . . .
N5 N 0.03757(12) 0.98580(9) 0.79725(8) 0.0117(2) Uani 1 1 d . . . . .
N4 N 0.66105(12) 0.48721(9) 0.72365(8) 0.0113(2) Uani 1 1 d . . . . .
C12 C 0.57867(15) 0.76803(11) 0.42349(10) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.62524(14) 0.86656(10) 0.68918(9) 0.0117(2) Uani 1 1 d . . . . .
H4 H 0.724320 0.816094 0.678042 0.014 Uiso 1 1 calc R U . . .
C25 C 0.17103(14) 0.91654(10) 0.77983(9) 0.0103(2) Uani 1 1 d . . . . .
C18 C 0.30585(14) 0.78771(10) 0.57104(9) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.56904(14) 0.90333(10) 0.61667(9) 0.0117(2) Uani 1 1 d . . . . .
C27 C 0.14233(14) 0.74849(10) 0.86398(9) 0.0125(3) Uani 1 1 d . . . . .
H27A H 0.095487 0.724145 0.830667 0.015 Uiso 1 1 calc R U . . .
H27B H 0.068272 0.791314 0.911784 0.015 Uiso 1 1 calc R U . . .
C24 C 0.58238(14) 0.58969(10) 0.73430(9) 0.0103(2) Uani 1 1 d . . . . .
C1 C 0.51501(14) 0.83729(10) 0.50162(9) 0.0118(2) Uani 1 1 d . . . . .
H1 H 0.451048 0.906684 0.482086 0.014 Uiso 1 1 calc R U . . .
C34 C 0.59783(15) 0.40912(11) 0.71972(10) 0.0140(3) Uani 1 1 d . . . . .
H34 H 0.493665 0.446046 0.731160 0.017 Uiso 1 1 calc R U . . .
C31 C 0.81701(14) 0.45234(11) 0.70055(10) 0.0147(3) Uani 1 1 d . . . . .
H31 H 0.850846 0.374210 0.699097 0.018 Uiso 1 1 calc R U . . .
C10 C 0.57360(17) 0.82059(13) 1.01890(10) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.518196 0.844931 1.076102 0.025 Uiso 1 1 calc R U . . .
C26 C 0.35245(14) 0.57960(10) 0.83534(9) 0.0121(3) Uani 1 1 d . . . . .
H26A H 0.409784 0.515967 0.865150 0.015 Uiso 1 1 calc R U . . .
H26B H 0.304021 0.557030 0.801881 0.015 Uiso 1 1 calc R U . . .
C13 C 0.64435(16) 0.66055(12) 0.43810(12) 0.0223(3) Uani 1 1 d . . . . .
H13 H 0.643291 0.629816 0.497524 0.027 Uiso 1 1 calc R U . . .
C23 C 0.22643(15) 0.86020(11) 0.51484(10) 0.0158(3) Uani 1 1 d . . . . .
H23 H 0.260503 0.912876 0.478405 0.019 Uiso 1 1 calc R U . . .
C5 C 0.54622(14) 0.88032(10) 0.78000(9) 0.0118(2) Uani 1 1 d . . . . .
C11 C 0.52548(15) 0.86608(12) 0.94329(10) 0.0157(3) Uani 1 1 d . . . . .
H11 H 0.437115 0.921460 0.949656 0.019 Uiso 1 1 calc R U . . .
C17 C 0.57995(18) 0.81117(13) 0.33604(10) 0.0211(3) Uani 1 1 d . . . . .
H17 H 0.533493 0.884404 0.325389 0.025 Uiso 1 1 calc R U . . .
C9 C 0.70260(18) 0.73951(13) 1.01141(10) 0.0225(3) Uani 1 1 d . . . . .
H9 H 0.735516 0.707779 1.063180 0.027 Uiso 1 1 calc R U . . .
C37 C -0.08776(14) 0.95469(11) 0.81368(10) 0.0132(3) Uani 1 1 d . . . . .
H37 H -0.053781 0.876341 0.814054 0.016 Uiso 1 1 calc R U . . .
C19 C 0.25199(15) 0.70963(11) 0.62118(10) 0.0155(3) Uani 1 1 d . . . . .
H19 H 0.304976 0.657220 0.657510 0.019 Uiso 1 1 calc R U . . .
C40 C 0.01435(15) 1.10026(10) 0.78829(10) 0.0154(3) Uani 1 1 d . . . . .
H40 H -0.090066 1.136561 0.806941 0.019 Uiso 1 1 calc R U . . .
C28 C 0.24145(14) 0.65230(10) 0.90713(9) 0.0124(3) Uani 1 1 d . . . . .
C39 C -0.16018(16) 0.99962(12) 0.73774(11) 0.0191(3) Uani 1 1 d . . . . .
H39A H -0.194878 1.076587 0.735416 0.029 Uiso 1 1 calc R U . . .
H39B H -0.239571 0.974880 0.748439 0.029 Uiso 1 1 calc R U . . .
H39C H -0.092618 0.976263 0.680575 0.029 Uiso 1 1 calc R U . . .
C36 C 0.62260(17) 0.31946(11) 0.79264(12) 0.0224(3) Uani 1 1 d . . . . .
H36A H 0.724158 0.283848 0.785217 0.034 Uiso 1 1 calc R U . . .
H36B H 0.580220 0.269181 0.787799 0.034 Uiso 1 1 calc R U . . .
H36C H 0.579330 0.347765 0.851761 0.034 Uiso 1 1 calc R U . . .
C20 C 0.12309(16) 0.70729(12) 0.61888(11) 0.0195(3) Uani 1 1 d . . . . .
H20 H 0.087813 0.655168 0.655293 0.023 Uiso 1 1 calc R U . . .
C6 C 0.60417(14) 0.83233(11) 0.85724(9) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.63211(15) 0.85625(11) 0.52760(9) 0.0130(3) Uani 1 1 d . . . . .
H2A H 0.710029 0.789034 0.531932 0.016 Uiso 1 1 calc R U . . .
H2B H 0.670298 0.904758 0.481554 0.016 Uiso 1 1 calc R U . . .
C42 C 0.06461(17) 1.14468(12) 0.69236(11) 0.0220(3) Uani 1 1 d . . . . .
H42A H 0.167891 1.117934 0.673353 0.033 Uiso 1 1 calc R U . . .
H42B H 0.030899 1.221603 0.690327 0.033 Uiso 1 1 calc R U . . .
H42C H 0.027234 1.122927 0.651982 0.033 Uiso 1 1 calc R U . . .
C38 C -0.18912(15) 0.98425(12) 0.90511(10) 0.0197(3) Uani 1 1 d . . . . .
H38A H -0.139203 0.952410 0.952002 0.030 Uiso 1 1 calc R U . . .
H38B H -0.267479 0.958470 0.915411 0.030 Uiso 1 1 calc R U . . .
H38C H -0.225884 1.060896 0.906720 0.030 Uiso 1 1 calc R U . . .
C33 C 0.86634(16) 0.47252(13) 0.77497(11) 0.0231(3) Uani 1 1 d . . . . .
H33A H 0.836741 0.548439 0.779026 0.035 Uiso 1 1 calc R U . . .
H33B H 0.969367 0.442007 0.761587 0.035 Uiso 1 1 calc R U . . .
H33C H 0.824674 0.440100 0.832204 0.035 Uiso 1 1 calc R U . . .
C7 C 0.73513(15) 0.75138(11) 0.85119(10) 0.0156(3) Uani 1 1 d . . . . .
H7 H 0.792190 0.727551 0.794122 0.019 Uiso 1 1 calc R U . . .
C32 C 0.88623(16) 0.49384(13) 0.60796(11) 0.0231(3) Uani 1 1 d . . . . .
H32A H 0.847261 0.482765 0.562873 0.035 Uiso 1 1 calc R U . . .
H32B H 0.988210 0.456231 0.593452 0.035 Uiso 1 1 calc R U . . .
H32C H 0.867581 0.569138 0.608198 0.035 Uiso 1 1 calc R U . . .
C8 C 0.78264(16) 0.70557(12) 0.92719(10) 0.0196(3) Uani 1 1 d . . . . .
H8 H 0.871037 0.650307 0.921459 0.024 Uiso 1 1 calc R U . . .
C30 C 0.31143(16) 0.68604(12) 0.96289(10) 0.0182(3) Uani 1 1 d . . . . .
H30A H 0.369508 0.726131 0.923816 0.027 Uiso 1 1 calc R U . . .
H30B H 0.371011 0.623575 0.991214 0.027 Uiso 1 1 calc R U . . .
H30C H 0.238633 0.730058 1.009371 0.027 Uiso 1 1 calc R U . . .
C29 C 0.15184(15) 0.58835(11) 0.96837(10) 0.0177(3) Uani 1 1 d . . . . .
H29A H 0.075720 0.632983 1.013137 0.027 Uiso 1 1 calc R U . . .
H29B H 0.211309 0.528144 0.998834 0.027 Uiso 1 1 calc R U . . .
H29C H 0.111344 0.563156 0.932169 0.027 Uiso 1 1 calc R U . . .
C21 C 0.04541(15) 0.78016(12) 0.56405(11) 0.0198(3) Uani 1 1 d . . . . .
H21 H -0.042427 0.778359 0.562210 0.024 Uiso 1 1 calc R U . . .
C41 C 0.07386(17) 1.12761(13) 0.85411(12) 0.0238(3) Uani 1 1 d . . . . .
H41A H 0.033047 1.102895 0.915206 0.036 Uiso 1 1 calc R U . . .
H41B H 0.050192 1.203987 0.850569 0.036 Uiso 1 1 calc R U . . .
H41C H 0.176562 1.093528 0.838833 0.036 Uiso 1 1 calc R U . . .
C22 C 0.09907(16) 0.85580(12) 0.51193(11) 0.0199(3) Uani 1 1 d . . . . .
H22 H 0.047588 0.905614 0.473438 0.024 Uiso 1 1 calc R U . . .
C14 C 0.71184(18) 0.59752(14) 0.36602(14) 0.0309(4) Uani 1 1 d . . . . .
H14 H 0.756064 0.523930 0.376477 0.037 Uiso 1 1 calc R U . . .
C35 C 0.65095(18) 0.36836(13) 0.62623(11) 0.0254(3) Uani 1 1 d . . . . .
H35A H 0.632414 0.427843 0.581264 0.038 Uiso 1 1 calc R U . . .
H35B H 0.601868 0.321512 0.623874 0.038 Uiso 1 1 calc R U . . .
H35C H 0.752568 0.329621 0.613686 0.038 Uiso 1 1 calc R U . . .
C16 C 0.64838(19) 0.74846(15) 0.26399(11) 0.0284(4) Uani 1 1 d . . . . .
H16 H 0.649510 0.778924 0.204490 0.034 Uiso 1 1 calc R U . . .
C15 C 0.71460(18) 0.64191(16) 0.27917(13) 0.0326(4) Uani 1 1 d . . . . .
H15 H 0.762108 0.598969 0.230051 0.039 Uiso 1 1 calc R U . . .
H3 H 0.4796(19) 0.9598(14) 0.6217(12) 0.019(4) Uiso 1 1 d . . . . .
H5 H 0.4641(17) 0.9418(13) 0.7913(11) 0.012(4) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 Zr1 O1 159.93(4) . . ?
O2 Zr1 C4 90.05(4) . . ?
O2 Zr1 C25 29.40(4) . . ?
O2 Zr1 C3 78.57(4) . . ?
O2 Zr1 C24 165.89(4) . . ?
O2 Zr1 C5 77.73(4) . . ?
O1 Zr1 C4 70.29(4) . . ?
O1 Zr1 C25 163.56(4) . . ?
O1 Zr1 C3 86.13(4) . . ?
O1 Zr1 C24 29.39(4) . . ?
O1 Zr1 C5 83.31(4) . . ?
N3 Zr1 O2 59.43(4) . . ?
N3 Zr1 O1 134.84(4) . . ?
N3 Zr1 C4 139.31(4) . . ?
N3 Zr1 C25 30.33(4) . . ?
N3 Zr1 C3 137.97(4) . . ?
N3 Zr1 C24 107.38(4) . . ?
N3 Zr1 C5 108.87(4) . . ?
N2 Zr1 O2 136.51(4) . . ?
N2 Zr1 O1 59.14(4) . . ?
N2 Zr1 N3 77.20(4) . . ?
N2 Zr1 C4 125.15(4) . . ?
N2 Zr1 C25 107.49(4) . . ?
N2 Zr1 C3 144.80(4) . . ?
N2 Zr1 C24 30.25(4) . . ?
N2 Zr1 C5 116.70(4) . . ?
N1 Zr1 O2 93.72(4) . . ?
N1 Zr1 O1 93.25(4) . . ?
N1 Zr1 N3 108.71(4) . . ?
N1 Zr1 N2 103.68(4) . . ?
N1 Zr1 C4 98.73(4) . . ?
N1 Zr1 C25 99.69(4) . . ?
N1 Zr1 C3 70.31(4) . . ?
N1 Zr1 C24 95.67(4) . . ?
N1 Zr1 C5 129.42(4) . . ?
C4 Zr1 C25 117.13(4) . . ?
C4 Zr1 C3 31.66(4) . . ?
C4 Zr1 C24 98.89(4) . . ?
C25 Zr1 C24 137.70(4) . . ?
C3 Zr1 C25 107.70(4) . . ?
C3 Zr1 C24 114.57(4) . . ?
C5 Zr1 C4 32.97(4) . . ?
C5 Zr1 C25 96.03(4) . . ?
C5 Zr1 C3 59.12(4) . . ?
C5 Zr1 C24 104.03(4) . . ?
C25 O2 Zr1 94.00(8) . . ?
C24 O1 Zr1 92.89(7) . . ?
C25 N3 Zr1 93.60(8) . . ?
C25 N3 C27 128.98(11) . . ?
C27 N3 Zr1 137.42(8) . . ?
C24 N2 Zr1 94.04(8) . . ?
C24 N2 C26 128.13(11) . . ?
C26 N2 Zr1 137.57(8) . . ?
C18 N1 Zr1 114.45(8) . . ?
C18 N1 C1 114.72(11) . . ?
C1 N1 Zr1 125.92(8) . . ?
C25 N5 C37 123.11(11) . . ?
C25 N5 C40 119.17(11) . . ?
C37 N5 C40 117.24(10) . . ?
C24 N4 C34 121.67(11) . . ?
C24 N4 C31 120.61(11) . . ?
C31 N4 C34 116.98(11) . . ?
C13 C12 C1 119.95(13) . . ?
C13 C12 C17 118.88(14) . . ?
C17 C12 C1 121.06(13) . . ?
Zr1 C4 H4 117.3 . . ?
C3 C4 Zr1 74.39(8) . . ?
C3 C4 H4 117.3 . . ?
C3 C4 C5 124.52(13) . . ?
C5 C4 Zr1 72.74(8) . . ?
C5 C4 H4 117.3 . . ?
O2 C25 Zr1 56.60(6) . . ?
O2 C25 N3 111.90(11) . . ?
O2 C25 N5 118.55(12) . . ?
N3 C25 Zr1 56.07(7) . . ?
N3 C25 N5 129.55(12) . . ?
N5 C25 Zr1 170.27(10) . . ?
C23 C18 N1 123.85(12) . . ?
C19 C18 N1 119.33(12) . . ?
C19 C18 C23 116.78(13) . . ?
Zr1 C3 H3 86.8(10) . . ?
C4 C3 Zr1 73.95(8) . . ?
C4 C3 C2 124.40(13) . . ?
C4 C3 H3 120.6(10) . . ?
C2 C3 Zr1 106.21(8) . . ?
C2 C3 H3 114.8(10) . . ?
N3 C27 H27A 109.3 . . ?
N3 C27 H27B 109.3 . . ?
N3 C27 C28 111.80(11) . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 H27A 109.3 . . ?
C28 C27 H27B 109.3 . . ?
O1 C24 Zr1 57.72(6) . . ?
O1 C24 N2 112.12(11) . . ?
O1 C24 N4 119.61(12) . . ?
N2 C24 Zr1 55.70(7) . . ?
N2 C24 N4 128.23(12) . . ?
N4 C24 Zr1 167.27(10) . . ?
N1 C1 C12 112.69(11) . . ?
N1 C1 H1 108.3 . . ?
N1 C1 C2 109.11(11) . . ?
C12 C1 H1 108.3 . . ?
C12 C1 C2 110.05(11) . . ?
C2 C1 H1 108.3 . . ?
N4 C34 H34 107.4 . . ?
N4 C34 C36 111.64(12) . . ?
N4 C34 C35 111.03(12) . . ?
C36 C34 H34 107.4 . . ?
C36 C34 C35 111.70(13) . . ?
C35 C34 H34 107.4 . . ?
N4 C31 H31 105.9 . . ?
N4 C31 C33 110.73(12) . . ?
N4 C31 C32 115.11(12) . . ?
C33 C31 H31 105.9 . . ?
C33 C31 C32 112.46(13) . . ?
C32 C31 H31 105.9 . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.28(14) . . ?
C9 C10 H10 119.9 . . ?
N2 C26 H26A 109.2 . . ?
N2 C26 H26B 109.2 . . ?
N2 C26 C28 111.92(11) . . ?
H26A C26 H26B 107.9 . . ?
C28 C26 H26A 109.2 . . ?
C28 C26 H26B 109.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.32(16) . . ?
C14 C13 H13 119.8 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.98(14) . . ?
C22 C23 H23 119.5 . . ?
Zr1 C5 H5 93.3(10) . . ?
C4 C5 Zr1 74.29(8) . . ?
C4 C5 C6 124.16(12) . . ?
C4 C5 H5 116.9(10) . . ?
C6 C5 Zr1 121.39(9) . . ?
C6 C5 H5 115.1(10) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C6 121.72(14) . . ?
C6 C11 H11 119.1 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.83(16) . . ?
C16 C17 H17 119.6 . . ?
C10 C9 H9 120.5 . . ?
C8 C9 C10 119.05(14) . . ?
C8 C9 H9 120.5 . . ?
N5 C37 H37 107.3 . . ?
N5 C37 C39 110.98(11) . . ?
N5 C37 C38 111.64(12) . . ?
C39 C37 H37 107.3 . . ?
C38 C37 H37 107.3 . . ?
C38 C37 C39 112.07(12) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.59(13) . . ?
C20 C19 H19 119.2 . . ?
N5 C40 H40 106.2 . . ?
N5 C40 C42 114.53(12) . . ?
N5 C40 C41 111.01(12) . . ?
C42 C40 H40 106.2 . . ?
C41 C40 H40 106.2 . . ?
C41 C40 C42 112.13(13) . . ?
C26 C28 C27 110.91(11) . . ?
C30 C28 C27 111.20(11) . . ?
C30 C28 C26 111.11(11) . . ?
C30 C28 C29 109.36(12) . . ?
C29 C28 C27 107.55(11) . . ?
C29 C28 C26 106.51(11) . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.77(14) . . ?
C21 C20 H20 119.6 . . ?
C11 C6 C5 119.56(13) . . ?
C7 C6 C5 123.48(12) . . ?
C7 C6 C11 116.95(13) . . ?
C3 C2 C1 107.86(11) . . ?
C3 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.16(13) . . ?
C8 C7 H7 119.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C9 C8 C7 120.83(14) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.41(14) . . ?
C22 C21 H21 120.8 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C23 C22 H22 119.3 . . ?
C21 C22 C23 121.40(14) . . ?
C21 C22 H22 119.3 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.14(17) . . ?
C15 C14 H14 119.9 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.82(17) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.00(16) . . ?
C16 C15 H15 120.0 . . ?
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 O2 2.2112(9) . ?
Zr1 O1 2.2369(9) . ?
Zr1 N3 2.1966(11) . ?
Zr1 N2 2.1885(11) . ?
Zr1 N1 2.1262(12) . ?
Zr1 C4 2.5134(13) . ?
Zr1 C25 2.6422(13) . ?
Zr1 C3 2.5189(13) . ?
Zr1 C24 2.6424(13) . ?
Zr1 C5 2.4934(14) . ?
O2 C25 1.3002(16) . ?
O1 C24 1.2984(16) . ?
N3 C25 1.3367(16) . ?
N3 C27 1.4564(17) . ?
N2 C24 1.3345(17) . ?
N2 C26 1.4523(17) . ?
N1 C18 1.4165(17) . ?
N1 C1 1.4816(17) . ?
N5 C25 1.3528(17) . ?
N5 C37 1.4807(17) . ?
N5 C40 1.4872(17) . ?
N4 C24 1.3529(16) . ?
N4 C34 1.4830(17) . ?
N4 C31 1.4817(17) . ?
C12 C1 1.5181(19) . ?
C12 C13 1.388(2) . ?
C12 C17 1.391(2) . ?
C4 H4 1.0000 . ?
C4 C3 1.3728(19) . ?
C4 C5 1.4208(19) . ?
C18 C23 1.4087(19) . ?
C18 C19 1.4064(19) . ?
C3 C2 1.5016(19) . ?
C3 H3 0.966(18) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.5424(19) . ?
C1 H1 1.0000 . ?
C1 C2 1.5386(19) . ?
C34 H34 1.0000 . ?
C34 C36 1.526(2) . ?
C34 C35 1.531(2) . ?
C31 H31 1.0000 . ?
C31 C33 1.522(2) . ?
C31 C32 1.529(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C10 C9 1.390(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C28 1.5399(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.389(2) . ?
C5 C6 1.4636(19) . ?
C5 H5 0.955(16) . ?
C11 H11 0.9500 . ?
C11 C6 1.4087(19) . ?
C17 H17 0.9500 . ?
C17 C16 1.391(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.388(2) . ?
C37 H37 1.0000 . ?
C37 C39 1.526(2) . ?
C37 C38 1.523(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C40 H40 1.0000 . ?
C40 C42 1.531(2) . ?
C40 C41 1.525(2) . ?
C28 C30 1.529(2) . ?
C28 C29 1.5368(19) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C6 C7 1.4048(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.389(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C8 H8 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C22 H22 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C15 1.379(3) . ?
C15 H15 0.9500 . ?
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 O2 C25 N3 9.74(11) . . . . ?
Zr1 O2 C25 N5 -170.16(11) . . . . ?
Zr1 O1 C24 N2 -12.55(11) . . . . ?
Zr1 O1 C24 N4 165.48(11) . . . . ?
Zr1 N3 C25 O2 -9.81(11) . . . . ?
Zr1 N3 C25 N5 170.09(13) . . . . ?
Zr1 N3 C27 C28 28.26(19) . . . . ?
Zr1 N2 C24 O1 12.85(11) . . . . ?
Zr1 N2 C24 N4 -164.97(13) . . . . ?
Zr1 N2 C26 C28 -29.27(19) . . . . ?
Zr1 N1 C18 C23 126.69(12) . . . . ?
Zr1 N1 C18 C19 -51.02(15) . . . . ?
Zr1 N1 C1 C12 138.31(10) . . . . ?
Zr1 N1 C1 C2 15.76(15) . . . . ?
Zr1 C4 C3 C2 -98.91(12) . . . . ?
Zr1 C4 C5 C6 117.59(13) . . . . ?
Zr1 C3 C2 C1 47.94(12) . . . . ?
Zr1 C5 C6 C11 -100.07(13) . . . . ?
Zr1 C5 C6 C7 78.58(15) . . . . ?
N3 C27 C28 C26 -62.73(15) . . . . ?
N3 C27 C28 C30 61.46(15) . . . . ?
N3 C27 C28 C29 -178.83(11) . . . . ?
N2 C26 C28 C27 63.27(15) . . . . ?
N2 C26 C28 C30 -60.96(15) . . . . ?
N2 C26 C28 C29 -179.98(11) . . . . ?
N1 C18 C23 C22 -175.82(13) . . . . ?
N1 C18 C19 C20 174.71(13) . . . . ?
N1 C1 C2 C3 -43.20(14) . . . . ?
C12 C1 C2 C3 -167.33(11) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C12 C17 C16 C15 0.7(2) . . . . ?
C4 C3 C2 C1 129.32(14) . . . . ?
C4 C5 C6 C11 168.16(13) . . . . ?
C4 C5 C6 C7 -13.2(2) . . . . ?
C25 N3 C27 C28 -152.28(13) . . . . ?
C25 N5 C37 C39 -112.50(14) . . . . ?
C25 N5 C37 C38 121.70(14) . . . . ?
C25 N5 C40 C42 65.93(17) . . . . ?
C25 N5 C40 C41 -62.30(17) . . . . ?
C18 N1 C1 C12 -68.03(15) . . . . ?
C18 N1 C1 C2 169.42(11) . . . . ?
C18 C23 C22 C21 0.0(2) . . . . ?
C18 C19 C20 C21 2.4(2) . . . . ?
C3 C4 C5 Zr1 56.24(12) . . . . ?
C3 C4 C5 C6 173.82(13) . . . . ?
C27 N3 C25 Zr1 -179.64(16) . . . . ?
C27 N3 C25 O2 170.56(13) . . . . ?
C27 N3 C25 N5 -9.6(2) . . . . ?
C24 N2 C26 C28 143.27(13) . . . . ?
C24 N4 C34 C36 -121.99(14) . . . . ?
C24 N4 C34 C35 112.65(14) . . . . ?
C24 N4 C31 C33 63.10(17) . . . . ?
C24 N4 C31 C32 -65.84(17) . . . . ?
C1 N1 C18 C23 -30.06(18) . . . . ?
C1 N1 C18 C19 152.23(12) . . . . ?
C1 C12 C13 C14 -175.38(14) . . . . ?
C1 C12 C17 C16 174.75(14) . . . . ?
C34 N4 C24 Zr1 -77.8(5) . . . . ?
C34 N4 C24 O1 -152.01(12) . . . . ?
C34 N4 C24 N2 25.7(2) . . . . ?
C34 N4 C31 C33 -126.59(13) . . . . ?
C34 N4 C31 C32 104.47(15) . . . . ?
C31 N4 C24 Zr1 92.1(4) . . . . ?
C31 N4 C24 O1 17.84(19) . . . . ?
C31 N4 C24 N2 -164.48(13) . . . . ?
C31 N4 C34 C36 67.81(15) . . . . ?
C31 N4 C34 C35 -57.55(16) . . . . ?
C10 C11 C6 C5 177.74(13) . . . . ?
C10 C11 C6 C7 -1.0(2) . . . . ?
C10 C9 C8 C7 -0.2(2) . . . . ?
C26 N2 C24 Zr1 -174.96(16) . . . . ?
C26 N2 C24 O1 -162.11(13) . . . . ?
C26 N2 C24 N4 20.1(2) . . . . ?
C13 C12 C1 N1 -45.00(18) . . . . ?
C13 C12 C1 C2 77.03(16) . . . . ?
C13 C12 C17 C16 -1.4(2) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C23 C18 C19 C20 -3.2(2) . . . . ?
C5 C4 C3 Zr1 -55.52(12) . . . . ?
C5 C4 C3 C2 -154.43(13) . . . . ?
C5 C6 C7 C8 -177.31(13) . . . . ?
C11 C10 C9 C8 0.5(2) . . . . ?
C11 C6 C7 C8 1.4(2) . . . . ?
C17 C12 C1 N1 138.88(14) . . . . ?
C17 C12 C1 C2 -99.09(16) . . . . ?
C17 C12 C13 C14 0.8(2) . . . . ?
C17 C16 C15 C14 0.5(3) . . . . ?
C9 C10 C11 C6 0.1(2) . . . . ?
C37 N5 C25 O2 154.02(12) . . . . ?
C37 N5 C25 N3 -25.9(2) . . . . ?
C37 N5 C40 C42 -106.40(14) . . . . ?
C37 N5 C40 C41 125.36(13) . . . . ?
C19 C18 C23 C22 1.9(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C40 N5 C25 O2 -17.85(19) . . . . ?
C40 N5 C25 N3 162.27(14) . . . . ?
C40 N5 C37 C39 59.50(16) . . . . ?
C40 N5 C37 C38 -66.30(16) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
