#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/23/7022363.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_7022363
loop_
_publ_author_name
'Kreye, Markus'
'Glöckner, Andreas'
'Daniliuc, Constantin G.'
'Freytag, Matthias'
'Jones, Peter G.'
'Tamm, Matthias'
'Walter, Marc D.'
_publ_section_title
;
 Sterically encumbered pyrrolyl ligands and their incorporation into the
 cycloheptatrienyl zirconium coordination sphere.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2192
_journal_page_last               2200
_journal_paper_doi               10.1039/c2dt32433d
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C48 H52 Li N3'
_chemical_formula_weight         677.87
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.377(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.6834(4)
_cell_length_b                   17.2623(2)
_cell_length_c                   11.8317(2)
_cell_measurement_reflns_used    16466
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8881
_cell_measurement_theta_min      3.4251
_cell_volume                     3960.07(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26512
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.08
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0628P)²+3.0547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                3761
_reflns_number_total             4114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt32433d.txt
_cod_data_source_block           mwal15
_cod_original_cell_volume        3960.07(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7022363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Li Li 0.5000 0.45664(18) 0.2500 0.0389(8) Uani 1 2 d S . .
N1 N 0.5000 0.56832(8) 0.2500 0.0259(3) Uani 1 2 d S . .
N2 N 0.47910(8) 0.37290(8) 0.35627(12) 0.0460(3) Uani 1 1 d . . .
C1 C 0.55637(6) 0.61584(7) 0.28122(11) 0.0248(3) Uani 1 1 d . . .
C2 C 0.53680(6) 0.69389(7) 0.27041(11) 0.0232(3) Uani 1 1 d . . .
C3 C 0.62491(6) 0.57893(7) 0.31324(11) 0.0267(3) Uani 1 1 d . . .
C4 C 0.64097(7) 0.51521(8) 0.39090(12) 0.0321(3) Uani 1 1 d . . .
H4 H 0.6088 0.4986 0.4269 0.038 Uiso 1 1 calc R . .
C5 C 0.70296(8) 0.47549(8) 0.41673(14) 0.0387(3) Uani 1 1 d . . .
H5 H 0.7127 0.4323 0.4697 0.046 Uiso 1 1 calc R . .
C6 C 0.75030(8) 0.49890(9) 0.36524(15) 0.0414(4) Uani 1 1 d . . .
H6 H 0.7925 0.4717 0.3820 0.050 Uiso 1 1 calc R . .
C7 C 0.73557(7) 0.56240(9) 0.28887(14) 0.0391(3) Uani 1 1 d . . .
H7 H 0.7681 0.5788 0.2537 0.047 Uiso 1 1 calc R . .
C8 C 0.67381(7) 0.60231(8) 0.26314(13) 0.0324(3) Uani 1 1 d . . .
H8 H 0.6647 0.6459 0.2110 0.039 Uiso 1 1 calc R . .
C9 C 0.58368(6) 0.76119(7) 0.29425(11) 0.0231(3) Uani 1 1 d . . .
C10 C 0.64381(6) 0.76351(7) 0.39603(12) 0.0297(3) Uani 1 1 d . . .
H10 H 0.6539 0.7217 0.4517 0.036 Uiso 1 1 calc R . .
C11 C 0.68919(7) 0.82576(8) 0.41739(13) 0.0336(3) Uani 1 1 d . . .
H11 H 0.7300 0.8258 0.4867 0.040 Uiso 1 1 calc R . .
C12 C 0.67522(7) 0.88770(7) 0.33793(13) 0.0312(3) Uani 1 1 d . . .
H12 H 0.7064 0.9301 0.3520 0.037 Uiso 1 1 calc R . .
C13 C 0.61539(7) 0.88713(8) 0.23787(13) 0.0304(3) Uani 1 1 d . . .
H13 H 0.6050 0.9298 0.1838 0.037 Uiso 1 1 calc R . .
C14 C 0.57029(6) 0.82460(7) 0.21572(11) 0.0262(3) Uani 1 1 d . . .
H14 H 0.5297 0.8249 0.1461 0.031 Uiso 1 1 calc R . .
C15 C 0.47496(16) 0.30515(11) 0.2801(2) 0.0809(8) Uani 1 1 d . . .
H15A H 0.4816 0.2579 0.3304 0.097 Uiso 1 1 calc R . .
H15B H 0.4281 0.3027 0.2184 0.097 Uiso 1 1 calc R . .
C16 C 0.41153(15) 0.3811(2) 0.3700(3) 0.0965(9) Uani 1 1 d . . .
H16A H 0.3757 0.3865 0.2904 0.145 Uiso 1 1 calc R . .
H16B H 0.4117 0.4272 0.4185 0.145 Uiso 1 1 calc R . .
H16C H 0.4021 0.3351 0.4104 0.145 Uiso 1 1 calc R . .
C17 C 0.53176(14) 0.36497(16) 0.4739(2) 0.0868(9) Uani 1 1 d . . .
H17A H 0.5330 0.4119 0.5212 0.130 Uiso 1 1 calc R . .
H17B H 0.5767 0.3575 0.4649 0.130 Uiso 1 1 calc R . .
H17C H 0.5213 0.3201 0.5154 0.130 Uiso 1 1 calc R . .
C91 C 0.47431(11) -0.02444(11) -0.0175(2) 0.0344(6) Uani 0.50 1 d PGDU A -1
C92 C 0.45953(11) 0.01157(13) 0.0757(2) 0.0433(11) Uani 0.50 1 d PGDU A -1
H92 H 0.4233 -0.0075 0.1000 0.052 Uiso 0.50 1 calc PR A -1
C93 C 0.49779(13) 0.07544(13) 0.1335(2) 0.0442(7) Uani 0.50 1 d PGDU A -1
H93 H 0.4877 0.1001 0.1972 0.053 Uiso 0.50 1 calc PR A -1
C94 C 0.55083(12) 0.10330(12) 0.0980(2) 0.0438(15) Uani 0.50 1 d PGDU A -1
H94 H 0.5770 0.1469 0.1375 0.053 Uiso 0.50 1 calc PR A -1
C95 C 0.56562(10) 0.06728(13) 0.0047(2) 0.0364(6) Uani 0.50 1 d PGDU A -1
H95 H 0.6019 0.0863 -0.0195 0.044 Uiso 0.50 1 calc PR A -1
C96 C 0.52736(10) 0.00342(12) -0.05302(19) 0.0341(8) Uani 0.50 1 d PGDU A -1
H96 H 0.5375 -0.0212 -0.1168 0.041 Uiso 0.50 1 calc PR A -1
C97 C 0.4329(3) -0.0925(3) -0.0826(5) 0.0471(11) Uani 0.50 1 d PDU A -1
H97A H 0.4011 -0.1087 -0.0420 0.071 Uiso 0.50 1 calc PR A -1
H97B H 0.4640 -0.1354 -0.0822 0.071 Uiso 0.50 1 calc PR A -1
H97C H 0.4065 -0.0779 -0.1660 0.071 Uiso 0.50 1 calc PR A -1
C81 C 0.8029(3) 0.7094(3) 0.0211(4) 0.0460(11) Uani 0.50 1 d PGDU B -1
C82 C 0.7737(3) 0.7282(3) -0.1004(4) 0.0440(9) Uani 0.50 1 d PGDU B -1
H82 H 0.7944 0.7104 -0.1558 0.053 Uiso 0.50 1 calc PR B -1
C83 C 0.7142(3) 0.7730(4) -0.1409(3) 0.0560(14) Uani 0.50 1 d PGDU B -1
H83 H 0.6942 0.7858 -0.2239 0.067 Uiso 0.50 1 calc PR B -1
C84 C 0.6839(3) 0.7991(4) -0.0599(4) 0.077(2) Uani 0.50 1 d PGDU B -1
H84 H 0.6433 0.8297 -0.0875 0.092 Uiso 0.50 1 calc PR B -1
C85 C 0.7131(3) 0.7803(4) 0.0617(4) 0.090(3) Uani 0.50 1 d PGDU B -1
H85 H 0.6924 0.7981 0.1170 0.108 Uiso 0.50 1 calc PR B -1
C86 C 0.7726(3) 0.7355(4) 0.1022(3) 0.065(2) Uani 0.50 1 d PGDU B -1
H86 H 0.7926 0.7227 0.1852 0.078 Uiso 0.50 1 calc PR B -1
C87 C 0.8634(2) 0.6589(2) 0.0610(4) 0.0569(9) Uani 0.50 1 d PDU B -1
H87A H 0.8489 0.6058 0.0690 0.085 Uiso 0.50 1 calc PR B -1
H87B H 0.8952 0.6769 0.1391 0.085 Uiso 0.50 1 calc PR B -1
H87C H 0.8866 0.6602 0.0016 0.085 Uiso 0.50 1 calc PR B -1
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'
Li Li 0.0008 0.0003 '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'
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
N1 Li N2 134.62(7) . .
N1 Li N2 134.61(7) . 2_655
N2 Li N2 90.77(15) . 2_655
N1 Li C15 164.54(6) . 2_655
N2 Li C15 59.57(10) . 2_655
N2 Li C15 32.08(7) 2_655 2_655
N1 Li C15 164.54(6) . .
N2 Li C15 32.08(7) . .
N2 Li C15 59.57(10) 2_655 .
C15 Li C15 30.92(11) 2_655 .
C1 N1 C1 106.24(14) . 2_655
C1 N1 Li 126.88(7) . .
C1 N1 Li 126.88(7) 2_655 .
C17 N2 C15 112.4(2) . .
C17 N2 C16 109.25(18) . .
C15 N2 C16 107.0(2) . .
C17 N2 Li 114.00(12) . .
C15 N2 Li 99.49(12) . .
C16 N2 Li 114.22(14) . .
N1 C1 C2 111.14(11) . .
N1 C1 C3 117.52(11) . .
C2 C1 C3 131.25(11) . .
C1 C2 C2 105.74(7) . 2_655
C1 C2 C9 126.18(11) . .
C2 C2 C9 128.07(6) 2_655 .
C4 C3 C8 117.69(12) . .
C4 C3 C1 119.67(12) . .
C8 C3 C1 122.53(12) . .
C5 C4 C3 121.49(13) . .
C6 C5 C4 119.97(14) . .
C5 C6 C7 119.38(13) . .
C6 C7 C8 120.80(14) . .
C7 C8 C3 120.66(13) . .
C10 C9 C14 117.41(11) . .
C10 C9 C2 121.01(11) . .
C14 C9 C2 121.58(11) . .
C11 C10 C9 121.34(12) . .
C12 C11 C10 120.30(12) . .
C13 C12 C11 119.22(12) . .
C12 C13 C14 120.56(12) . .
C13 C14 C9 121.15(12) . .
C15 C15 N2 113.91(19) 2_655 .
C15 C15 Li 74.54(6) 2_655 .
N2 C15 Li 48.43(7) . .
C92 C91 C96 120.0 . .
C92 C91 C97 120.9(3) . .
C96 C91 C97 119.1(3) . .
C91 C92 C93 120.0 . .
C94 C93 C92 120.0 . .
C95 C94 C93 120.0 . .
C96 C95 C94 120.0 . .
C95 C96 C91 120.0 . .
C82 C81 C86 120.0 . .
C82 C81 C87 119.2(3) . .
C86 C81 C87 120.7(3) . .
C83 C82 C81 120.0 . .
C84 C83 C82 120.0 . .
C85 C84 C83 120.0 . .
C86 C85 C84 120.0 . .
C85 C86 C81 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li N1 1.928(4) .
Li N2 2.058(3) .
Li N2 2.058(3) 2_655
Li C15 2.713(4) 2_655
Li C15 2.713(4) .
N1 C1 1.3670(15) .
N1 C1 1.3670(15) 2_655
N2 C17 1.444(3) .
N2 C15 1.461(2) .
N2 C16 1.469(3) .
C1 C2 1.3997(17) .
C1 C3 1.4783(16) .
C2 C2 1.428(2) 2_655
C2 C9 1.4761(16) .
C3 C4 1.3971(18) .
C3 C8 1.3981(19) .
C4 C5 1.3910(19) .
C5 C6 1.381(2) .
C6 C7 1.385(2) .
C7 C8 1.3886(19) .
C9 C10 1.3984(17) .
C9 C14 1.3996(17) .
C10 C11 1.3910(18) .
C11 C12 1.386(2) .
C12 C13 1.383(2) .
C13 C14 1.3905(17) .
C15 C15 1.447(5) 2_655
C91 C92 1.3900 .
C91 C96 1.3900 .
C91 C97 1.499(4) .
C92 C93 1.3900 .
C93 C94 1.3900 .
C94 C95 1.3900 .
C95 C96 1.3900 .
C81 C82 1.3900 .
C81 C86 1.3900 .
C81 C87 1.462(6) .
C82 C83 1.3900 .
C83 C84 1.3900 .
C84 C85 1.3900 .
C85 C86 1.3900 .
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_4
N2 Li N1 C1 107.98(9) . .
N2 Li N1 C1 -72.02(9) 2_655 .
C15 Li N1 C1 -45.9(2) 2_655 .
C15 Li N1 C1 134.1(2) . .
N2 Li N1 C1 -72.03(9) . 2_655
N2 Li N1 C1 107.98(9) 2_655 2_655
C15 Li N1 C1 134.1(2) 2_655 2_655
C15 Li N1 C1 -45.9(2) . 2_655
N1 Li N2 C17 -72.92(18) . .
N2 Li N2 C17 107.08(18) 2_655 .
C15 Li N2 C17 99.25(19) 2_655 .
C15 Li N2 C17 119.8(2) . .
N1 Li N2 C15 167.24(13) . .
N2 Li N2 C15 -12.77(13) 2_655 .
C15 Li N2 C15 -20.6(2) 2_655 .
N1 Li N2 C16 53.67(19) . .
N2 Li N2 C16 -126.34(19) 2_655 .
C15 Li N2 C16 -134.2(2) 2_655 .
C15 Li N2 C16 -113.6(2) . .
C1 N1 C1 C2 0.01(6) 2_655 .
Li N1 C1 C2 -179.99(6) . .
C1 N1 C1 C3 -176.93(13) 2_655 .
Li N1 C1 C3 3.07(13) . .
N1 C1 C2 C2 -0.04(16) . 2_655
C3 C1 C2 C2 176.35(13) . 2_655
N1 C1 C2 C9 -178.79(10) . .
C3 C1 C2 C9 -2.4(2) . .
N1 C1 C3 C4 -45.67(16) . .
C2 C1 C3 C4 138.13(14) . .
N1 C1 C3 C8 130.44(12) . .
C2 C1 C3 C8 -45.8(2) . .
C8 C3 C4 C5 -0.8(2) . .
C1 C3 C4 C5 175.49(13) . .
C3 C4 C5 C6 0.1(2) . .
C4 C5 C6 C7 0.5(2) . .
C5 C6 C7 C8 -0.4(2) . .
C6 C7 C8 C3 -0.4(2) . .
C4 C3 C8 C7 1.0(2) . .
C1 C3 C8 C7 -175.21(13) . .
C1 C2 C9 C10 -44.04(18) . .
C2 C2 C9 C10 137.49(16) 2_655 .
C1 C2 C9 C14 135.25(13) . .
C2 C2 C9 C14 -43.2(2) 2_655 .
C14 C9 C10 C11 -1.10(19) . .
C2 C9 C10 C11 178.22(12) . .
C9 C10 C11 C12 0.6(2) . .
C10 C11 C12 C13 0.5(2) . .
C11 C12 C13 C14 -1.2(2) . .
C12 C13 C14 C9 0.69(19) . .
C10 C9 C14 C13 0.45(18) . .
C2 C9 C14 C13 -178.87(11) . .
C17 N2 C15 C15 -82.5(3) . 2_655
C16 N2 C15 C15 157.5(3) . 2_655
Li N2 C15 C15 38.5(3) . 2_655
C17 N2 C15 Li -121.00(17) . .
C16 N2 C15 Li 119.08(16) . .
N1 Li C15 C15 180.0 . 2_655
N2 Li C15 C15 -143.8(3) . 2_655
N2 Li C15 C15 21.31(19) 2_655 2_655
N1 Li C15 N2 -36.2(3) . .
N2 Li C15 N2 165.15(15) 2_655 .
C15 Li C15 N2 143.8(3) 2_655 .
C96 C91 C92 C93 0.0 . .
C97 C91 C92 C93 -178.9(3) . .
C91 C92 C93 C94 0.0 . .
C92 C93 C94 C95 0.0 . .
C93 C94 C95 C96 0.0 . .
C94 C95 C96 C91 0.0 . .
C92 C91 C96 C95 0.0 . .
C97 C91 C96 C95 178.9(3) . .
C86 C81 C82 C83 0.0 . .
C87 C81 C82 C83 176.8(3) . .
C81 C82 C83 C84 0.0 . .
C82 C83 C84 C85 0.0 . .
C83 C84 C85 C86 0.0 . .
C84 C85 C86 C81 0.0 . .
C82 C81 C86 C85 0.0 . .
C87 C81 C86 C85 -176.8(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139159975
