#------------------------------------------------------------------------------
#$Date: 2024-08-05 20:03:39 +0200 (Mon 05 de Aug de 2024) $
#$Revision: 293760 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/18/1571810.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_1571810
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         'C37 H57 N5 O2 Zr'
_chemical_formula_sum            'C37 H57 N5 O2 Zr'
_chemical_formula_weight         695.09
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-05-25 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                96.630(2)
_cell_angle_beta                 103.052(2)
_cell_angle_gamma                109.933(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4694(7)
_cell_length_b                   13.7275(10)
_cell_length_c                   14.5277(11)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.40
_cell_volume                     1869.4(2)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53872
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.639
_diffrn_reflns_theta_min         1.614
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0606 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8751.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       irregular
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         11493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0371
_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)+(0.0458P)²+0.1789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9331
_reflns_number_total             11493
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00636d2.cif
_cod_data_source_block           mo_ls933_0m
_cod_depositor_comments
'Adding full bibliography for 1571809--1571811.cif.'
_cod_database_code               1571810
_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   0.952
_shelx_estimated_absorpt_t_min   0.871
_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:
 C26(H26), C3(H3), C32(H32), C29(H29), C1(H1), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C5(H5A,H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C18(H18), C10(H10), C11(H11), C9(H9), C15(H15), C17(H17),
 C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C28(H28A,H28B,
 H28C), C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C24(H24A,H24B,H24C), C27(H27A,
 H27B,H27C), C37(H37A,H37B,H37C), C6(H6A,H6B,H6C), C36(H36A,H36B,H36C)
;
_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 0.37074(2) 0.31954(2) 0.76655(2) 0.01154(5) Uani 1 1 d . . . . .
O1 O 0.38043(12) 0.48555(9) 0.77607(9) 0.0163(2) Uani 1 1 d . . . . .
O2 O 0.42946(12) 0.17854(9) 0.76366(9) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.21533(14) 0.36994(10) 0.81883(10) 0.0128(3) Uani 1 1 d . . . . .
N3 N 0.24303(14) 0.17561(10) 0.80821(10) 0.0125(3) Uani 1 1 d . . . . .
N1 N 0.30139(14) 0.29126(11) 0.61251(11) 0.0148(3) Uani 1 1 d . . . . .
N5 N 0.28779(14) 0.01439(10) 0.77326(11) 0.0143(3) Uani 1 1 d . . . . .
N4 N 0.20256(14) 0.53959(10) 0.79134(11) 0.0144(3) Uani 1 1 d . . . . .
C19 C 0.26117(16) 0.46520(12) 0.79662(12) 0.0129(3) Uani 1 1 d . . . . .
C4 C 0.63696(17) 0.38095(13) 0.78351(15) 0.0198(4) Uani 1 1 d . . . . .
C21 C 0.09186(17) 0.31987(12) 0.85163(12) 0.0139(3) Uani 1 1 d . . . . .
H21A H 0.007042 0.287521 0.794952 0.017 Uiso 1 1 calc R U . . .
H21B H 0.077179 0.374697 0.893781 0.017 Uiso 1 1 calc R U . . .
C26 C 0.05423(17) 0.51838(12) 0.79133(13) 0.0163(3) Uani 1 1 d . . . . .
H26 H 0.006231 0.440127 0.784206 0.020 Uiso 1 1 calc R U . . .
C20 C 0.31598(16) 0.11950(12) 0.78273(12) 0.0122(3) Uani 1 1 d . . . . .
C34 C 0.08880(19) -0.14938(13) 0.67345(13) 0.0186(3) Uani 1 1 d . . . . .
H34A H 0.087086 -0.115157 0.617846 0.028 Uiso 1 1 calc R U . . .
H34B H -0.007612 -0.196917 0.668984 0.028 Uiso 1 1 calc R U . . .
H34C H 0.149419 -0.190276 0.673723 0.028 Uiso 1 1 calc R U . . .
C7 C 0.33168(18) 0.27763(14) 0.44619(14) 0.0195(3) Uani 1 1 d . . . . .
C30 C 0.42063(19) 0.70221(13) 0.86856(14) 0.0232(4) Uani 1 1 d . . . . .
H30A H 0.393340 0.702281 0.928801 0.035 Uiso 1 1 calc R U . . .
H30B H 0.469003 0.775397 0.863251 0.035 Uiso 1 1 calc R U . . .
H30C H 0.484488 0.664025 0.868694 0.035 Uiso 1 1 calc R U . . .
C23 C 0.10709(18) 0.23425(12) 0.90740(12) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.57509(17) 0.40710(13) 0.70097(14) 0.0173(3) Uani 1 1 d . . . . .
H3 H 0.599750 0.485245 0.708791 0.021 Uiso 1 1 calc R U . . .
C32 C 0.14686(17) -0.06542(12) 0.76605(12) 0.0138(3) Uani 1 1 d . . . . .
H32 H 0.080503 -0.027302 0.764277 0.017 Uiso 1 1 calc R U . . .
C31 C 0.32239(19) 0.65112(13) 0.68626(14) 0.0207(4) Uani 1 1 d . . . . .
H31A H 0.390148 0.617103 0.682788 0.031 Uiso 1 1 calc R U . . .
H31B H 0.363605 0.725018 0.680432 0.031 Uiso 1 1 calc R U . . .
H31C H 0.235110 0.613420 0.633457 0.031 Uiso 1 1 calc R U . . .
C22 C 0.11932(16) 0.14244(11) 0.84360(12) 0.0121(3) Uani 1 1 d . . . . .
H22A H 0.123755 0.087452 0.881318 0.014 Uiso 1 1 calc R U . . .
H22B H 0.033257 0.110211 0.787809 0.014 Uiso 1 1 calc R U . . .
C13 C 0.15722(18) 0.27828(14) 0.58407(13) 0.0172(3) Uani 1 1 d . . . . .
C28 C -0.02769(19) 0.54946(14) 0.70650(15) 0.0224(4) Uani 1 1 d . . . . .
H28A H 0.007884 0.626862 0.715780 0.034 Uiso 1 1 calc R U . . .
H28B H -0.128606 0.522116 0.702949 0.034 Uiso 1 1 calc R U . . .
H28C H -0.014930 0.519341 0.646304 0.034 Uiso 1 1 calc R U . . .
C29 C 0.28857(17) 0.64770(12) 0.78297(13) 0.0168(3) Uani 1 1 d . . . . .
H29 H 0.228336 0.690344 0.785770 0.020 Uiso 1 1 calc R U . . .
C8 C 0.2947(2) 0.16765(15) 0.42611(15) 0.0242(4) Uani 1 1 d . . . . .
H8 H 0.299363 0.131056 0.477651 0.029 Uiso 1 1 calc R U . . .
C25 C 0.2337(2) 0.28169(14) 0.99757(13) 0.0227(4) Uani 1 1 d . . . . .
H25A H 0.320619 0.312780 0.978645 0.034 Uiso 1 1 calc R U . . .
H25B H 0.240919 0.225928 1.032477 0.034 Uiso 1 1 calc R U . . .
H25C H 0.221034 0.336825 1.039497 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3212(2) 0.32846(15) 0.36968(14) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.343786 0.402754 0.382241 0.028 Uiso 1 1 calc R U . . .
C33 C 0.1507(2) -0.11385(13) 0.85565(13) 0.0216(4) Uani 1 1 d . . . . .
H33A H 0.219632 -0.148047 0.862155 0.032 Uiso 1 1 calc R U . . .
H33B H 0.056594 -0.166624 0.849209 0.032 Uiso 1 1 calc R U . . .
H33C H 0.178366 -0.057959 0.913095 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1094(2) 0.35162(15) 0.54189(14) 0.0226(4) Uani 1 1 d . . . . .
H18 H 0.174314 0.409143 0.524796 0.027 Uiso 1 1 calc R U . . .
C1 C 0.38661(18) 0.34022(13) 0.54978(13) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.384308 0.412368 0.549082 0.021 Uiso 1 1 calc R U . . .
C24 C -0.0302(2) 0.18691(13) 0.93562(15) 0.0225(4) Uani 1 1 d . . . . .
H24A H -0.042567 0.242504 0.977182 0.034 Uiso 1 1 calc R U . . .
H24B H -0.025048 0.130774 0.970543 0.034 Uiso 1 1 calc R U . . .
H24C H -0.110709 0.157169 0.877175 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2429(2) 0.16457(17) 0.25486(15) 0.0284(4) Uani 1 1 d . . . . .
H10 H 0.213473 0.126445 0.189964 0.034 Uiso 1 1 calc R U . . .
C35 C 0.39903(19) -0.02671(13) 0.76280(15) 0.0215(4) Uani 1 1 d . . . . .
H35 H 0.358329 -0.103911 0.763292 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2782(2) 0.27277(17) 0.27465(15) 0.0288(4) Uani 1 1 d . . . . .
H11 H 0.273015 0.309360 0.223126 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2511(2) 0.11180(16) 0.33109(16) 0.0284(4) Uani 1 1 d . . . . .
H9 H 0.226700 0.037301 0.318065 0.034 Uiso 1 1 calc R U . . .
C5 C 0.60766(18) 0.41075(14) 0.87206(14) 0.0211(4) Uani 1 1 d . . . . .
H5A H 0.635644 0.487841 0.895085 0.025 Uiso 1 1 calc R U . . .
H5B H 0.635538 0.375681 0.924622 0.025 Uiso 1 1 calc R U . . .
C27 C 0.0464(2) 0.57112(14) 0.88728(15) 0.0243(4) Uani 1 1 d . . . . .
H27A H 0.092709 0.545390 0.940116 0.036 Uiso 1 1 calc R U . . .
H27B H -0.053090 0.553658 0.885741 0.036 Uiso 1 1 calc R U . . .
H27C H 0.094474 0.648143 0.897554 0.036 Uiso 1 1 calc R U . . .
C2 C 0.54084(18) 0.35347(13) 0.59738(14) 0.0199(4) Uani 1 1 d . . . . .
H2A H 0.549406 0.283574 0.593300 0.024 Uiso 1 1 calc R U . . .
H2B H 0.605952 0.397420 0.564994 0.024 Uiso 1 1 calc R U . . .
C37 C 0.4324(2) -0.02066(15) 0.66587(17) 0.0312(5) Uani 1 1 d . . . . .
H37A H 0.343866 -0.050913 0.613232 0.047 Uiso 1 1 calc R U . . .
H37B H 0.492219 -0.060734 0.658090 0.047 Uiso 1 1 calc R U . . .
H37C H 0.482455 0.053556 0.664221 0.047 Uiso 1 1 calc R U . . .
C15 C -0.0851(2) 0.18316(19) 0.58582(14) 0.0313(5) Uani 1 1 d . . . . .
H15 H -0.151898 0.125109 0.600958 0.038 Uiso 1 1 calc R U . . .
C6 C 0.71142(19) 0.30436(15) 0.77922(18) 0.0307(5) Uani 1 1 d . . . . .
H6A H 0.705001 0.267529 0.832920 0.046 Uiso 1 1 calc R U . . .
H6B H 0.811268 0.343423 0.784158 0.046 Uiso 1 1 calc R U . . .
H6C H 0.666303 0.252459 0.717795 0.046 Uiso 1 1 calc R U . . .
C17 C -0.0306(2) 0.34107(17) 0.52499(15) 0.0294(4) Uani 1 1 d . . . . .
H17 H -0.060106 0.391942 0.497154 0.035 Uiso 1 1 calc R U . . .
C14 C 0.05591(19) 0.19122(16) 0.60252(14) 0.0241(4) Uani 1 1 d . . . . .
H14 H 0.082757 0.137398 0.626448 0.029 Uiso 1 1 calc R U . . .
C36 C 0.5309(2) 0.02155(15) 0.84909(18) 0.0318(5) Uani 1 1 d . . . . .
H36A H 0.578271 0.097019 0.850418 0.048 Uiso 1 1 calc R U . . .
H36B H 0.595668 -0.014761 0.843517 0.048 Uiso 1 1 calc R U . . .
H36C H 0.503676 0.013433 0.908869 0.048 Uiso 1 1 calc R U . . .
C16 C -0.1282(2) 0.25780(19) 0.54795(15) 0.0327(5) Uani 1 1 d . . . . .
H16 H -0.223518 0.252195 0.537728 0.039 Uiso 1 1 calc R U . . .
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
O1 Zr1 C19 28.99(4) . . ?
O1 Zr1 C4 91.28(5) . . ?
O1 Zr1 C20 165.66(5) . . ?
O1 Zr1 C3 76.58(5) . . ?
O1 Zr1 C5 81.32(5) . . ?
O2 Zr1 O1 163.00(4) . . ?
O2 Zr1 C19 165.84(5) . . ?
O2 Zr1 C4 71.73(5) . . ?
O2 Zr1 C20 29.19(4) . . ?
O2 Zr1 C3 88.63(5) . . ?
O2 Zr1 C5 83.87(5) . . ?
N2 Zr1 O1 58.57(4) . . ?
N2 Zr1 O2 135.99(4) . . ?
N2 Zr1 C19 30.02(5) . . ?
N2 Zr1 C4 141.31(5) . . ?
N2 Zr1 C20 107.50(5) . . ?
N2 Zr1 C3 135.09(5) . . ?
N2 Zr1 C5 111.92(6) . . ?
N3 Zr1 O1 135.87(5) . . ?
N3 Zr1 O2 58.91(4) . . ?
N3 Zr1 N2 77.47(5) . . ?
N3 Zr1 C19 107.43(5) . . ?
N3 Zr1 C4 125.43(5) . . ?
N3 Zr1 C20 30.03(5) . . ?
N3 Zr1 C3 147.44(5) . . ?
N3 Zr1 C5 114.81(6) . . ?
N1 Zr1 O1 90.25(5) . . ?
N1 Zr1 O2 92.38(5) . . ?
N1 Zr1 N2 106.15(5) . . ?
N1 Zr1 N3 106.50(5) . . ?
N1 Zr1 C19 95.54(5) . . ?
N1 Zr1 C4 96.78(6) . . ?
N1 Zr1 C20 97.59(5) . . ?
N1 Zr1 C3 69.50(6) . . ?
N1 Zr1 C5 128.26(6) . . ?
C4 Zr1 C19 118.74(5) . . ?
C4 Zr1 C20 99.64(5) . . ?
C20 Zr1 C19 137.43(5) . . ?
C3 Zr1 C19 105.13(5) . . ?
C3 Zr1 C4 31.37(6) . . ?
C3 Zr1 C20 117.41(5) . . ?
C5 Zr1 C19 100.23(6) . . ?
C5 Zr1 C4 33.35(6) . . ?
C5 Zr1 C20 102.78(5) . . ?
C5 Zr1 C3 58.85(6) . . ?
C19 O1 Zr1 94.28(9) . . ?
C20 O2 Zr1 94.38(9) . . ?
C19 N2 Zr1 93.90(10) . . ?
C19 N2 C21 129.16(14) . . ?
C21 N2 Zr1 136.33(10) . . ?
C20 N3 Zr1 93.76(9) . . ?
C20 N3 C22 129.19(13) . . ?
C22 N3 Zr1 136.93(10) . . ?
C13 N1 Zr1 108.36(10) . . ?
C13 N1 C1 115.68(14) . . ?
C1 N1 Zr1 125.93(11) . . ?
C20 N5 C32 123.54(13) . . ?
C20 N5 C35 119.79(13) . . ?
C32 N5 C35 116.54(12) . . ?
C19 N4 C26 123.35(13) . . ?
C19 N4 C29 119.51(13) . . ?
C26 N4 C29 117.12(12) . . ?
O1 C19 Zr1 56.73(7) . . ?
O1 C19 N2 111.63(13) . . ?
O1 C19 N4 117.62(13) . . ?
N2 C19 Zr1 56.08(8) . . ?
N2 C19 N4 130.74(15) . . ?
N4 C19 Zr1 167.56(12) . . ?
C3 C4 Zr1 72.60(9) . . ?
C3 C4 C5 119.12(16) . . ?
C3 C4 C6 121.17(18) . . ?
C5 C4 Zr1 67.25(9) . . ?
C5 C4 C6 118.67(17) . . ?
C6 C4 Zr1 122.43(11) . . ?
N2 C21 H21A 109.1 . . ?
N2 C21 H21B 109.1 . . ?
N2 C21 C23 112.54(13) . . ?
H21A C21 H21B 107.8 . . ?
C23 C21 H21A 109.1 . . ?
C23 C21 H21B 109.1 . . ?
N4 C26 H26 107.1 . . ?
N4 C26 C28 112.80(14) . . ?
N4 C26 C27 111.48(14) . . ?
C28 C26 H26 107.1 . . ?
C28 C26 C27 110.95(14) . . ?
C27 C26 H26 107.1 . . ?
O2 C20 Zr1 56.43(7) . . ?
O2 C20 N3 111.82(13) . . ?
O2 C20 N5 118.17(14) . . ?
N3 C20 Zr1 56.21(8) . . ?
N3 C20 N5 130.00(14) . . ?
N5 C20 Zr1 169.19(12) . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
C8 C7 C1 120.77(16) . . ?
C12 C7 C8 118.56(18) . . ?
C12 C7 C1 120.65(16) . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
C21 C23 C22 111.74(13) . . ?
C25 C23 C21 110.79(13) . . ?
C25 C23 C22 110.58(14) . . ?
C25 C23 C24 110.26(15) . . ?
C24 C23 C21 107.10(14) . . ?
C24 C23 C22 106.21(13) . . ?
Zr1 C3 H3 112.1 . . ?
C4 C3 Zr1 76.03(10) . . ?
C4 C3 H3 112.1 . . ?
C4 C3 C2 128.87(16) . . ?
C2 C3 Zr1 109.16(10) . . ?
C2 C3 H3 112.1 . . ?
N5 C32 C34 112.16(13) . . ?
N5 C32 H32 107.1 . . ?
N5 C32 C33 110.86(14) . . ?
C34 C32 H32 107.1 . . ?
C34 C32 C33 112.06(13) . . ?
C33 C32 H32 107.1 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
N3 C22 C23 112.87(12) . . ?
N3 C22 H22A 109.0 . . ?
N3 C22 H22B 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C18 C13 N1 123.38(16) . . ?
C14 C13 N1 119.15(16) . . ?
C14 C13 C18 117.39(16) . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N4 C29 C30 112.26(14) . . ?
N4 C29 C31 113.45(14) . . ?
N4 C29 H29 106.1 . . ?
C30 C29 C31 112.27(15) . . ?
C30 C29 H29 106.1 . . ?
C31 C29 H29 106.1 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.31(18) . . ?
C9 C8 H8 119.8 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C7 C12 H12 119.4 . . ?
C7 C12 C11 121.17(18) . . ?
C11 C12 H12 119.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.99(18) . . ?
C17 C18 H18 119.5 . . ?
N1 C1 C7 113.26(14) . . ?
N1 C1 H1 108.1 . . ?
N1 C1 C2 106.99(14) . . ?
C7 C1 H1 108.1 . . ?
C7 C1 C2 111.98(14) . . ?
C2 C1 H1 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C10 H10 120.3 . . ?
C11 C10 C9 119.31(19) . . ?
C9 C10 H10 120.3 . . ?
N5 C35 H35 105.8 . . ?
N5 C35 C37 113.33(15) . . ?
N5 C35 C36 112.27(16) . . ?
C37 C35 H35 105.8 . . ?
C36 C35 H35 105.8 . . ?
C36 C35 C37 112.99(17) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.28(19) . . ?
C10 C11 H11 119.9 . . ?
C8 C9 C10 120.35(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
Zr1 C5 H5A 115.4 . . ?
Zr1 C5 H5B 115.4 . . ?
C4 C5 Zr1 79.39(10) . . ?
C4 C5 H5A 115.4 . . ?
C4 C5 H5B 115.4 . . ?
H5A C5 H5B 112.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C3 C2 C1 105.79(14) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C16 C15 C14 121.15(19) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C13 C14 C15 120.31(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C15 C16 C17 118.93(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
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 O1 2.2330(11) . ?
Zr1 O2 2.2205(11) . ?
Zr1 N2 2.2153(14) . ?
Zr1 N3 2.2132(13) . ?
Zr1 N1 2.1353(15) . ?
Zr1 C19 2.6634(16) . ?
Zr1 C4 2.5650(16) . ?
Zr1 C20 2.6572(15) . ?
Zr1 C3 2.5222(16) . ?
Zr1 C5 2.4066(18) . ?
O1 C19 1.2946(19) . ?
O2 C20 1.2996(18) . ?
N2 C19 1.3356(19) . ?
N2 C21 1.455(2) . ?
N3 C20 1.333(2) . ?
N3 C22 1.4498(19) . ?
N1 C13 1.414(2) . ?
N1 C1 1.476(2) . ?
N5 C20 1.3540(19) . ?
N5 C32 1.480(2) . ?
N5 C35 1.485(2) . ?
N4 C19 1.3598(19) . ?
N4 C26 1.479(2) . ?
N4 C29 1.4860(19) . ?
C4 C3 1.376(3) . ?
C4 C5 1.435(3) . ?
C4 C6 1.511(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C23 1.534(2) . ?
C26 H26 1.0000 . ?
C26 C28 1.526(2) . ?
C26 C27 1.528(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34 C32 1.517(2) . ?
C7 C8 1.401(2) . ?
C7 C12 1.382(3) . ?
C7 C1 1.519(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 C29 1.523(3) . ?
C23 C22 1.536(2) . ?
C23 C25 1.526(3) . ?
C23 C24 1.532(2) . ?
C3 H3 1.0000 . ?
C3 C2 1.502(3) . ?
C32 H32 1.0000 . ?
C32 C33 1.527(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31 C29 1.526(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C13 C18 1.410(3) . ?
C13 C14 1.401(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29 1.0000 . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.391(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C17 1.384(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.544(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.380(3) . ?
C10 C9 1.394(3) . ?
C35 H35 1.0000 . ?
C35 C37 1.530(3) . ?
C35 C36 1.523(3) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C14 1.404(3) . ?
C15 C16 1.374(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C16 1.381(3) . ?
C14 H14 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C16 H16 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 O1 C19 N2 11.97(14) . . . . ?
Zr1 O1 C19 N4 -167.12(13) . . . . ?
Zr1 O2 C20 N3 -10.04(14) . . . . ?
Zr1 O2 C20 N5 169.08(13) . . . . ?
Zr1 N2 C19 O1 -12.06(14) . . . . ?
Zr1 N2 C19 N4 166.88(17) . . . . ?
Zr1 N2 C21 C23 34.8(2) . . . . ?
Zr1 N3 C20 O2 10.06(14) . . . . ?
Zr1 N3 C20 N5 -168.92(17) . . . . ?
Zr1 N3 C22 C23 -32.0(2) . . . . ?
Zr1 N1 C13 C18 111.77(16) . . . . ?
Zr1 N1 C13 C14 -64.96(18) . . . . ?
Zr1 N1 C1 C7 158.94(11) . . . . ?
Zr1 N1 C1 C2 35.07(18) . . . . ?
Zr1 C4 C3 C2 -103.52(17) . . . . ?
Zr1 C3 C2 C1 44.97(14) . . . . ?
N2 C21 C23 C22 -62.94(18) . . . . ?
N2 C21 C23 C25 60.85(18) . . . . ?
N2 C21 C23 C24 -178.86(14) . . . . ?
N1 C13 C18 C17 -172.94(17) . . . . ?
N1 C13 C14 C15 172.29(17) . . . . ?
N1 C1 C2 C3 -50.13(17) . . . . ?
C19 N2 C21 C23 -156.66(16) . . . . ?
C19 N4 C26 C28 -127.16(17) . . . . ?
C19 N4 C26 C27 107.23(18) . . . . ?
C19 N4 C29 C30 -60.0(2) . . . . ?
C19 N4 C29 C31 68.6(2) . . . . ?
C4 C3 C2 C1 132.20(17) . . . . ?
C21 N2 C19 Zr1 -172.1(2) . . . . ?
C21 N2 C19 O1 175.83(16) . . . . ?
C21 N2 C19 N4 -5.2(3) . . . . ?
C21 C23 C22 N3 61.71(18) . . . . ?
C26 N4 C19 Zr1 106.1(5) . . . . ?
C26 N4 C19 O1 165.97(15) . . . . ?
C26 N4 C19 N2 -12.9(3) . . . . ?
C26 N4 C29 C30 121.31(16) . . . . ?
C26 N4 C29 C31 -110.09(17) . . . . ?
C20 N3 C22 C23 153.25(16) . . . . ?
C20 N5 C32 C34 121.69(17) . . . . ?
C20 N5 C32 C33 -112.21(17) . . . . ?
C20 N5 C35 C37 -69.7(2) . . . . ?
C20 N5 C35 C36 59.8(2) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C12 C11 C10 0.9(3) . . . . ?
C7 C1 C2 C3 -174.78(13) . . . . ?
C3 C4 C5 Zr1 52.79(14) . . . . ?
C32 N5 C20 Zr1 -105.3(6) . . . . ?
C32 N5 C20 O2 -162.57(15) . . . . ?
C32 N5 C20 N3 16.4(3) . . . . ?
C32 N5 C35 C37 106.36(17) . . . . ?
C32 N5 C35 C36 -124.13(16) . . . . ?
C22 N3 C20 Zr1 176.42(19) . . . . ?
C22 N3 C20 O2 -173.52(15) . . . . ?
C22 N3 C20 N5 7.5(3) . . . . ?
C13 N1 C1 C7 -59.79(19) . . . . ?
C13 N1 C1 C2 176.34(14) . . . . ?
C13 C18 C17 C16 -0.7(3) . . . . ?
C29 N4 C19 Zr1 -72.5(6) . . . . ?
C29 N4 C19 O1 -12.6(2) . . . . ?
C29 N4 C19 N2 168.46(17) . . . . ?
C29 N4 C26 C28 51.5(2) . . . . ?
C29 N4 C26 C27 -74.11(18) . . . . ?
C8 C7 C12 C11 -1.5(3) . . . . ?
C8 C7 C1 N1 -46.6(2) . . . . ?
C8 C7 C1 C2 74.5(2) . . . . ?
C25 C23 C22 N3 -62.20(18) . . . . ?
C12 C7 C8 C9 1.2(3) . . . . ?
C12 C7 C1 N1 135.36(17) . . . . ?
C12 C7 C1 C2 -103.55(19) . . . . ?
C18 C13 C14 C15 -4.6(3) . . . . ?
C18 C17 C16 C15 -1.7(3) . . . . ?
C1 N1 C13 C18 -36.0(2) . . . . ?
C1 N1 C13 C14 147.30(16) . . . . ?
C1 C7 C8 C9 -176.84(17) . . . . ?
C1 C7 C12 C11 176.57(17) . . . . ?
C24 C23 C22 N3 178.17(14) . . . . ?
C35 N5 C20 Zr1 70.5(7) . . . . ?
C35 N5 C20 O2 13.2(2) . . . . ?
C35 N5 C20 N3 -167.89(17) . . . . ?
C35 N5 C32 C34 -54.2(2) . . . . ?
C35 N5 C32 C33 71.91(18) . . . . ?
C11 C10 C9 C8 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C5 C4 C3 Zr1 -50.32(14) . . . . ?
C5 C4 C3 C2 -153.85(16) . . . . ?
C6 C4 C3 Zr1 117.85(15) . . . . ?
C6 C4 C3 C2 14.3(3) . . . . ?
C6 C4 C5 Zr1 -115.68(14) . . . . ?
C14 C13 C18 C17 3.8(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C16 C15 C14 C13 2.4(3) . . . . ?
