# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_jms23002
_database_code_depnum_ccdc_archive 'CCDC 2339708'
loop_
_audit_author_name
_audit_author_address
'Theo F. N. Tanner'
;University of York
United Kingdom
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2023-01-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 F3 N Zr'
_chemical_formula_sum            'C21 H20 F3 N Zr'
_chemical_formula_weight         434.60
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'Sara Bonfante SB36c'
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'
F F 0.0727 0.0534 '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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.17660(10)
_cell_length_b                   15.5546(2)
_cell_length_c                   14.6671(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.4290(10)
_cell_angle_gamma                90
_cell_volume                     1840.21(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8675
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      76.2160
_cell_measurement_theta_min      4.1470
_shelx_estimated_absorpt_T_max   0.652
_shelx_estimated_absorpt_T_min   0.357
_exptl_absorpt_coefficient_mu    5.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -2 -1 0.0385
2 2 1 0.0505
0 2 -1 0.0997
0 -2 1 0.1284
0 -1 -2 0.0506
-1 4 9 0.0289
2 -1 -2 0.0655
2 1 2 0.0666
-2 -1 0 0.0399
0 -1 2 0.1037

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
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
-1.9995 -1.9978 -0.9973 -0.0375 -0.1477 0.4317
1.9995 1.9978 0.9973 0.0375 0.1477 -0.4317
0.0015 1.9990 -1.0012 0.0756 0.2097 0.0290
-0.0015 -1.9990 1.0012 -0.0756 -0.2097 -0.0290
-0.0009 -1.0005 -1.9976 -0.1825 0.0618 0.1339
-1.0187 4.2805 8.6143 0.8633 -0.3056 -0.4018
1.9969 -1.0024 -1.9977 -0.3363 0.1332 -0.2081
1.9987 0.9985 1.9976 0.0286 0.0095 -0.4758
-1.9986 -0.9977 0.0010 0.0871 -0.1429 0.3571
-0.0007 -0.9990 1.9996 0.0490 -0.2049 -0.1035

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.951
_diffrn_reflns_theta_min         4.173
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -56.00   0.50    0.40    --  -48.70 165.00-121.00  114
  2  ω    -68.00 -29.00   0.50    0.40    --  -48.70 116.00  90.00   78
  3  ω   -108.00 -83.00   0.50    0.40    --  -48.70-165.00-145.00   50
  4  ω     34.00  59.00   0.50    0.40    --   48.70-116.00   2.00   50
  5  ω     65.00  90.00   0.50    0.40    --   48.70-165.00-145.00   50
  6  ω     69.00 118.00   0.50    1.61    --  107.75 165.00-121.00   98
  7  ω     96.00 125.00   0.50    1.61    --  107.75-165.00-145.00   58
  8  ω     79.00 105.00   0.50    1.61    --  107.75-116.00   2.00   52
  9  ω    106.00 167.00   0.50    1.61    --  107.75 116.00  90.00  122
 10  ω   -118.00 -74.00   0.50    0.40    --  -48.70-125.00  60.00   88
 11  ω    -61.00  24.00   0.50    0.40    --  -48.70  19.00-120.00  170
 12  ω   -105.00 -73.00   0.50    0.40    --  -48.70-125.00  30.00   64
 13  ω   -118.00 -90.00   0.50    0.40    --  -48.70-125.00 150.00   56
 14  ω     12.00  37.00   0.50    0.40    --   48.70 -99.00-180.00   50
 15  ω     43.00  99.00   0.50    1.61    --  107.75-125.00 -60.00  112
 16  ω     48.00  73.00   0.50    1.61    --  107.75 -77.00-180.00   50
 17  ω     39.00 106.00   0.50    1.61    --  107.75 -99.00-180.00  134
 18  ω     40.00 100.00   0.50    1.61    --  107.75 -99.00  60.00  120
 19  ω     89.00 114.00   0.50    1.61    --  107.75 -19.00 -60.00   50
 20  ω    132.00 171.00   0.50    1.61    --  107.75  57.00 150.00   78
 21  ω     91.00 130.00   0.50    1.61    --  107.75 -77.00-180.00   78
 22  ω     32.00  57.00   0.50    1.61    --  107.75 -19.00 -60.00   50
 23  ω     94.00 124.00   0.50    1.61    --  107.75  57.00 150.00   60
 24  ω     97.00 164.00   0.50    1.61    --  107.75  57.00-180.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0769238000
_diffrn_orient_matrix_UB_12      0.0668839000
_diffrn_orient_matrix_UB_13      0.0578794000
_diffrn_orient_matrix_UB_21      0.0357759000
_diffrn_orient_matrix_UB_22      0.0714525000
_diffrn_orient_matrix_UB_23      -0.0667467000
_diffrn_orient_matrix_UB_31      -0.1711812000
_diffrn_orient_matrix_UB_32      -0.0151058000
_diffrn_orient_matrix_UB_33      -0.0593791000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3429
_reflns_number_total             3722
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.095
_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)+(0.0180P)²+1.1752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0621
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C17(H17), C18(H18), C19(H19), C13(H13), C21(H21), C15(H15),
 C20(H20), C14(H14), C12(H12), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr1 Zr 0.45883(2) 0.19836(2) 0.57383(2) 0.01561(7) Uani 1 1 d . . . . .
F1 F 0.57605(16) 0.16492(8) 0.46910(9) 0.0285(3) Uani 1 1 d . . . . .
F2 F 0.38837(17) 0.48761(9) 0.89064(9) 0.0322(3) Uani 1 1 d . . . . .
F3 F 0.23270(18) 0.22446(9) 0.75244(10) 0.0338(3) Uani 1 1 d . . . . .
N1 N 0.4157(2) 0.30577(11) 0.69250(12) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.3948(3) 0.42833(14) 0.82430(15) 0.0234(4) Uani 1 1 d . . . . .
C8 C 0.4959(2) 0.44349(13) 0.76016(15) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.557331 0.495396 0.761034 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3198(3) 0.29817(14) 0.75631(16) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.3005(3) 0.35530(15) 0.82525(15) 0.0252(4) Uani 1 1 d . . . . .
H10 H 0.229169 0.345304 0.869157 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6083(2) 0.38879(13) 0.62127(15) 0.0201(4) Uani 1 1 d . . . . .
C17 C 0.4625(3) 0.08218(15) 0.69853(15) 0.0268(5) Uani 1 1 d . . . . .
H17 H 0.358812 0.066805 0.715089 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7106(3) 0.47035(14) 0.62256(17) 0.0271(5) Uani 1 1 d . . . . .
H5A H 0.770566 0.480326 0.685972 0.033 Uiso 1 1 calc R U . . .
H5B H 0.635715 0.519827 0.605377 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5059(2) 0.38023(13) 0.69316(13) 0.0173(4) Uani 1 1 d . . . . .
C18 C 0.5358(3) 0.04473(14) 0.62728(16) 0.0275(5) Uani 1 1 d . . . . .
H18 H 0.490226 -0.000520 0.587549 0.033 Uiso 1 1 calc R U . . .
C1 C 0.6036(2) 0.32453(14) 0.55864(14) 0.0200(4) Uani 1 1 d . . . . .
C19 C 0.6876(3) 0.08613(16) 0.62554(18) 0.0315(5) Uani 1 1 d . . . . .
H19 H 0.763975 0.073083 0.585170 0.038 Uiso 1 1 calc R U . . .
C13 C 0.1675(3) 0.26619(16) 0.53947(18) 0.0315(5) Uani 1 1 d . . . . .
H13 H 0.137847 0.310817 0.577858 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5701(3) 0.14605(15) 0.74036(16) 0.0292(5) Uani 1 1 d . . . . .
H21 H 0.553203 0.180573 0.791430 0.035 Uiso 1 1 calc R U . . .
C2 C 0.6968(3) 0.33498(15) 0.47859(16) 0.0277(5) Uani 1 1 d . . . . .
H2A H 0.624352 0.316032 0.421326 0.033 Uiso 1 1 calc R U . . .
H2B H 0.794676 0.296593 0.488521 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2031(3) 0.13414(15) 0.47915(16) 0.0261(5) Uani 1 1 d . . . . .
H15 H 0.204305 0.073625 0.470508 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8352(3) 0.46505(16) 0.55606(19) 0.0334(5) Uani 1 1 d . . . . .
H4A H 0.877434 0.523312 0.545815 0.040 Uiso 1 1 calc R U . . .
H4B H 0.930368 0.428951 0.583489 0.040 Uiso 1 1 calc R U . . .
C20 C 0.7072(3) 0.15044(15) 0.69411(18) 0.0317(5) Uani 1 1 d . . . . .
H20 H 0.797078 0.189714 0.706767 0.038 Uiso 1 1 calc R U . . .
C14 C 0.1466(3) 0.17769(15) 0.55266(16) 0.0265(5) Uani 1 1 d . . . . .
H14 H 0.102559 0.151792 0.602049 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2397(3) 0.27737(16) 0.46005(18) 0.0347(6) Uani 1 1 d . . . . .
H12 H 0.271494 0.330560 0.436378 0.042 Uiso 1 1 calc R U . . .
C3 C 0.7553(3) 0.42692(17) 0.46447(18) 0.0345(5) Uani 1 1 d . . . . .
H3A H 0.836274 0.426425 0.421125 0.041 Uiso 1 1 calc R U . . .
H3B H 0.659647 0.462720 0.437139 0.041 Uiso 1 1 calc R U . . .
C16 C 0.2565(3) 0.19564(16) 0.42164(17) 0.0315(5) Uani 1 1 d . . . . .
H16 H 0.297438 0.184313 0.365842 0.038 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 F1 2.0078(13) . ?
Zr1 N1 2.4791(17) . ?
Zr1 C17 2.568(2) . ?
Zr1 C18 2.561(2) . ?
Zr1 C1 2.321(2) . ?
Zr1 C19 2.580(2) . ?
Zr1 C13 2.578(2) . ?
Zr1 C15 2.520(2) . ?
Zr1 C20 2.573(2) . ?
Zr1 C14 2.541(2) . ?
Zr1 C12 2.555(2) . ?
Zr1 C16 2.552(2) . ?
F2 C9 1.348(2) . ?
F3 C11 1.346(3) . ?
N1 C11 1.321(3) . ?
N1 C7 1.372(3) . ?
C9 C8 1.370(3) . ?
C9 C10 1.374(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.403(3) . ?
C11 C10 1.374(3) . ?
C10 H10 0.9500 . ?
C6 C5 1.518(3) . ?
C6 C7 1.456(3) . ?
C6 C1 1.354(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.413(3) . ?
C17 C21 1.400(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.524(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.403(4) . ?
C1 C2 1.510(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.409(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.405(3) . ?
C13 C12 1.400(4) . ?
C21 H21 0.9500 . ?
C21 C20 1.404(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.533(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.413(3) . ?
C15 C16 1.392(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.515(4) . ?
C20 H20 0.9500 . ?
C14 H14 0.9500 . ?
C12 H12 0.9500 . ?
C12 C16 1.406(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C16 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
F1 Zr1 N1 148.46(6) . . ?
F1 Zr1 C17 114.28(7) . . ?
F1 Zr1 C18 82.43(7) . . ?
F1 Zr1 C1 80.26(6) . . ?
F1 Zr1 C19 68.63(7) . . ?
F1 Zr1 C13 119.87(7) . . ?
F1 Zr1 C15 86.14(7) . . ?
F1 Zr1 C20 91.57(7) . . ?
F1 Zr1 C14 118.01(7) . . ?
F1 Zr1 C12 89.80(8) . . ?
F1 Zr1 C16 69.44(7) . . ?
N1 Zr1 C17 87.74(7) . . ?
N1 Zr1 C18 118.03(7) . . ?
N1 Zr1 C19 115.41(7) . . ?
N1 Zr1 C13 68.19(7) . . ?
N1 Zr1 C15 116.97(7) . . ?
N1 Zr1 C20 84.31(7) . . ?
N1 Zr1 C14 85.16(7) . . ?
N1 Zr1 C12 88.24(8) . . ?
N1 Zr1 C16 118.62(7) . . ?
C17 Zr1 C19 52.50(8) . . ?
C17 Zr1 C13 109.26(8) . . ?
C17 Zr1 C20 52.55(8) . . ?
C18 Zr1 C17 31.97(7) . . ?
C18 Zr1 C19 31.66(8) . . ?
C18 Zr1 C13 127.91(8) . . ?
C18 Zr1 C20 52.63(7) . . ?
C1 Zr1 N1 68.34(7) . . ?
C1 Zr1 C17 135.78(7) . . ?
C1 Zr1 C18 135.62(7) . . ?
C1 Zr1 C19 104.10(8) . . ?
C1 Zr1 C13 96.00(8) . . ?
C1 Zr1 C15 132.26(7) . . ?
C1 Zr1 C20 87.31(7) . . ?
C1 Zr1 C14 127.81(7) . . ?
C1 Zr1 C12 81.07(7) . . ?
C1 Zr1 C16 101.41(7) . . ?
C13 Zr1 C19 159.47(8) . . ?
C15 Zr1 C17 91.45(7) . . ?
C15 Zr1 C18 86.49(7) . . ?
C15 Zr1 C19 112.96(8) . . ?
C15 Zr1 C13 52.97(7) . . ?
C15 Zr1 C20 138.92(8) . . ?
C15 Zr1 C14 32.43(8) . . ?
C15 Zr1 C12 53.18(7) . . ?
C15 Zr1 C16 31.86(8) . . ?
C20 Zr1 C19 31.73(8) . . ?
C20 Zr1 C13 148.53(9) . . ?
C14 Zr1 C17 83.82(7) . . ?
C14 Zr1 C18 96.36(8) . . ?
C14 Zr1 C19 128.01(8) . . ?
C14 Zr1 C13 31.84(7) . . ?
C14 Zr1 C20 135.37(8) . . ?
C14 Zr1 C12 52.98(8) . . ?
C14 Zr1 C16 52.89(8) . . ?
C12 Zr1 C17 136.79(8) . . ?
C12 Zr1 C18 139.43(7) . . ?
C12 Zr1 C19 156.16(9) . . ?
C12 Zr1 C13 31.65(9) . . ?
C12 Zr1 C20 167.90(8) . . ?
C16 Zr1 C17 122.80(8) . . ?
C16 Zr1 C18 110.11(7) . . ?
C16 Zr1 C19 125.51(8) . . ?
C16 Zr1 C13 52.41(8) . . ?
C16 Zr1 C20 157.05(8) . . ?
C16 Zr1 C12 31.97(8) . . ?
C11 N1 Zr1 127.31(14) . . ?
C11 N1 C7 116.83(18) . . ?
C7 N1 Zr1 115.83(13) . . ?
F2 C9 C8 118.5(2) . . ?
F2 C9 C10 118.0(2) . . ?
C8 C9 C10 123.5(2) . . ?
C9 C8 H8 120.9 . . ?
C9 C8 C7 118.1(2) . . ?
C7 C8 H8 120.9 . . ?
F3 C11 C10 117.3(2) . . ?
N1 C11 F3 114.70(18) . . ?
N1 C11 C10 128.0(2) . . ?
C9 C10 C11 113.3(2) . . ?
C9 C10 H10 123.4 . . ?
C11 C10 H10 123.4 . . ?
C7 C6 C5 116.65(18) . . ?
C1 C6 C5 125.4(2) . . ?
C1 C6 C7 117.92(18) . . ?
Zr1 C17 H17 116.9 . . ?
C18 C17 Zr1 73.75(13) . . ?
C18 C17 H17 126.1 . . ?
C21 C17 Zr1 75.29(13) . . ?
C21 C17 H17 126.1 . . ?
C21 C17 C18 107.7(2) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C6 C5 C4 111.83(19) . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
N1 C7 C8 120.26(19) . . ?
N1 C7 C6 116.37(18) . . ?
C8 C7 C6 123.37(19) . . ?
Zr1 C18 H18 116.8 . . ?
C17 C18 Zr1 74.27(12) . . ?
C17 C18 H18 126.0 . . ?
C19 C18 Zr1 74.92(13) . . ?
C19 C18 C17 107.9(2) . . ?
C19 C18 H18 126.0 . . ?
C6 C1 Zr1 121.15(15) . . ?
C6 C1 C2 119.11(19) . . ?
C2 C1 Zr1 119.73(15) . . ?
Zr1 C19 H19 118.7 . . ?
C18 C19 Zr1 73.41(12) . . ?
C18 C19 H19 126.0 . . ?
C18 C19 C20 108.1(2) . . ?
C20 C19 Zr1 73.84(13) . . ?
C20 C19 H19 126.0 . . ?
Zr1 C13 H13 120.1 . . ?
C14 C13 Zr1 72.62(12) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 Zr1 73.25(13) . . ?
C12 C13 H13 125.9 . . ?
C12 C13 C14 108.3(2) . . ?
Zr1 C21 H21 119.4 . . ?
C17 C21 Zr1 73.24(12) . . ?
C17 C21 H21 125.8 . . ?
C17 C21 C20 108.5(2) . . ?
C20 C21 Zr1 73.41(13) . . ?
C20 C21 H21 125.8 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 C3 114.5(2) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
Zr1 C15 H15 116.1 . . ?
C14 C15 Zr1 74.61(12) . . ?
C14 C15 H15 126.1 . . ?
C16 C15 Zr1 75.34(13) . . ?
C16 C15 H15 126.1 . . ?
C16 C15 C14 107.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C3 C4 C5 110.64(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
Zr1 C20 H20 116.5 . . ?
C19 C20 Zr1 74.43(13) . . ?
C19 C20 H20 126.2 . . ?
C21 C20 Zr1 75.06(13) . . ?
C21 C20 C19 107.7(2) . . ?
C21 C20 H20 126.2 . . ?
Zr1 C14 H14 117.4 . . ?
C13 C14 Zr1 75.54(13) . . ?
C13 C14 C15 107.6(2) . . ?
C13 C14 H14 126.2 . . ?
C15 C14 Zr1 72.96(12) . . ?
C15 C14 H14 126.2 . . ?
Zr1 C12 H12 116.9 . . ?
C13 C12 Zr1 75.09(13) . . ?
C13 C12 H12 126.2 . . ?
C13 C12 C16 107.7(2) . . ?
C16 C12 Zr1 73.90(13) . . ?
C16 C12 H12 126.2 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 C2 110.1(2) . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
Zr1 C16 H16 119.2 . . ?
C15 C16 Zr1 72.80(12) . . ?
C15 C16 C12 108.5(2) . . ?
C15 C16 H16 125.7 . . ?
C12 C16 Zr1 74.13(13) . . ?
C12 C16 H16 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 C11 F3 -2.6(3) . . . . ?
Zr1 N1 C11 C10 176.62(17) . . . . ?
Zr1 N1 C7 C8 -177.25(14) . . . . ?
Zr1 N1 C7 C6 3.2(2) . . . . ?
Zr1 C17 C18 C19 67.96(16) . . . . ?
Zr1 C17 C21 C20 -65.47(16) . . . . ?
Zr1 C18 C19 C20 66.25(16) . . . . ?
Zr1 C1 C2 C3 167.54(16) . . . . ?
Zr1 C19 C20 C21 68.30(16) . . . . ?
Zr1 C13 C14 C15 -66.46(15) . . . . ?
Zr1 C13 C12 C16 67.30(16) . . . . ?
Zr1 C21 C20 C19 -67.87(16) . . . . ?
Zr1 C15 C14 C13 68.20(15) . . . . ?
Zr1 C15 C16 C12 -66.08(16) . . . . ?
Zr1 C12 C16 C15 65.20(16) . . . . ?
F2 C9 C8 C7 177.99(17) . . . . ?
F2 C9 C10 C11 -178.29(18) . . . . ?
F3 C11 C10 C9 179.57(19) . . . . ?
N1 C11 C10 C9 0.3(3) . . . . ?
C9 C8 C7 N1 0.3(3) . . . . ?
C9 C8 C7 C6 179.82(18) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C11 N1 C7 C8 0.9(3) . . . . ?
C11 N1 C7 C6 -178.63(18) . . . . ?
C10 C9 C8 C7 -1.4(3) . . . . ?
C6 C5 C4 C3 43.9(3) . . . . ?
C6 C1 C2 C3 -13.5(3) . . . . ?
C17 C18 C19 Zr1 -67.52(15) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?
C17 C21 C20 Zr1 65.36(16) . . . . ?
C17 C21 C20 C19 -2.5(3) . . . . ?
C5 C6 C7 N1 -179.00(18) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C5 C6 C1 Zr1 174.46(16) . . . . ?
C5 C6 C1 C2 -4.5(3) . . . . ?
C5 C4 C3 C2 -61.9(3) . . . . ?
C7 N1 C11 F3 179.45(17) . . . . ?
C7 N1 C11 C10 -1.3(3) . . . . ?
C7 C6 C5 C4 169.57(19) . . . . ?
C7 C6 C1 Zr1 -6.2(3) . . . . ?
C7 C6 C1 C2 174.80(18) . . . . ?
C18 C17 C21 Zr1 67.19(15) . . . . ?
C18 C17 C21 C20 1.7(3) . . . . ?
C18 C19 C20 Zr1 -65.96(16) . . . . ?
C18 C19 C20 C21 2.3(3) . . . . ?
C1 C6 C5 C4 -11.1(3) . . . . ?
C1 C6 C7 N1 1.6(3) . . . . ?
C1 C6 C7 C8 -177.89(19) . . . . ?
C1 C2 C3 C4 46.3(3) . . . . ?
C13 C12 C16 Zr1 -68.11(15) . . . . ?
C13 C12 C16 C15 -2.9(3) . . . . ?
C21 C17 C18 Zr1 -68.23(15) . . . . ?
C21 C17 C18 C19 -0.3(2) . . . . ?
C14 C13 C12 Zr1 -64.67(15) . . . . ?
C14 C13 C12 C16 2.6(2) . . . . ?
C14 C15 C16 Zr1 68.13(15) . . . . ?
C14 C15 C16 C12 2.1(3) . . . . ?
C12 C13 C14 Zr1 65.08(15) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
C16 C15 C14 Zr1 -68.62(15) . . . . ?
C16 C15 C14 C13 -0.4(2) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.802
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
