#------------------------------------------------------------------------------
#$Date: 2022-08-03 01:58:42 +0300 (Wed, 03 Aug 2022) $
#$Revision: 277050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/08/7710895.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_7710895
loop_
_publ_author_name
'Koneczny, Marvin'
'Erol, Arife Büsra'
'Mauduit, Marc'
'Eisen, Moris S.'
'Tamm, Matthias'
_publ_section_title
;
 Titanium complexes with unsymmetrically substituted imidazolin-2-iminato
 ligands.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11448
_journal_page_last               11456
_journal_paper_doi               10.1039/d2dt01740g
_journal_volume                  51
_journal_year                    2022
_chemical_formula_sum            'C25 H34 N2'
_chemical_formula_weight         362.54
_chemical_name_systematic
1-(Adamantyl)-3-(2,6-diisopropylphenyl)-imidazolin-2-yliden
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-25 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4134(2)
_cell_length_b                   12.3697(2)
_cell_length_c                   16.5809(2)
_cell_measurement_reflns_used    24652
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6570
_cell_measurement_theta_min      4.4630
_cell_volume                     2135.80(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a(Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a(Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a(Rigaku OD, 2018)'
_computing_publication_material
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'
_computing_structure_refinement
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_structure_solution
'SHELXT-2014/5 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.393
_diffrn_reflns_theta_min         4.460
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene/n-hexane -30°C'
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0444P)²+0.8191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2232
_reflns_number_total             2337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01740g2.cif
_cod_data_source_block           mk28mk
_cod_database_code               7710895
_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_min   0.848
_shelx_estimated_absorpt_t_max   0.958
_oxdiff_exptl_absorpt_empirical_full_min 0.482
_oxdiff_exptl_absorpt_empirical_full_max 1.721
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_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
N1 N 0.42991(11) 0.750000 0.25846(7) 0.0200(3) Uani 1 2 d S T P . .
N2 N 0.43885(11) 0.750000 0.38599(7) 0.0204(3) Uani 1 2 d S T P . .
C1 C 0.51738(13) 0.750000 0.32025(8) 0.0217(3) Uani 1 2 d S T P . .
C2 C 0.30336(13) 0.750000 0.28421(9) 0.0244(3) Uani 1 2 d S T P . .
H2 H 0.228367 0.750000 0.251587 0.029 Uiso 1 2 calc R U P . .
C3 C 0.30927(13) 0.750000 0.36509(9) 0.0260(3) Uani 1 2 d S T P . .
H3 H 0.238477 0.750000 0.401226 0.031 Uiso 1 2 calc R U P . .
C4 C 0.46399(13) 0.750000 0.17459(8) 0.0199(3) Uani 1 2 d S T P . .
C5 C 0.47826(9) 0.65084(8) 0.13507(6) 0.0227(2) Uani 1 1 d . . . . .
C6 C 0.50586(10) 0.65320(8) 0.05262(6) 0.0253(2) Uani 1 1 d . . . . .
H6 H 0.515835 0.587084 0.024153 0.030 Uiso 1 1 calc R U . . .
C7 C 0.51893(14) 0.750000 0.01166(8) 0.0254(3) Uani 1 2 d S T P . .
H7 H 0.536860 0.750000 -0.044521 0.030 Uiso 1 2 calc R U P . .
C8 C 0.46195(11) 0.54394(9) 0.17881(6) 0.0296(3) Uani 1 1 d . . . . .
H8 H 0.454723 0.559933 0.237753 0.036 Uiso 1 1 calc R U . . .
C9 C 0.57811(13) 0.47054(10) 0.16697(7) 0.0377(3) Uani 1 1 d . . . . .
H9A H 0.585762 0.451325 0.109835 0.057 Uiso 1 1 calc R U . . .
H9B H 0.567233 0.404679 0.199105 0.057 Uiso 1 1 calc R U . . .
H9C H 0.655959 0.508452 0.184371 0.057 Uiso 1 1 calc R U . . .
C10 C 0.33741(13) 0.48896(10) 0.15250(8) 0.0396(3) Uani 1 1 d . . . . .
H10A H 0.264580 0.536776 0.163849 0.059 Uiso 1 1 calc R U . . .
H10B H 0.326807 0.421077 0.182238 0.059 Uiso 1 1 calc R U . . .
H10C H 0.340960 0.473760 0.094535 0.059 Uiso 1 1 calc R U . . .
C11 C 0.48252(13) 0.750000 0.47071(8) 0.0200(3) Uani 1 2 d S T P . .
C12 C 0.62940(14) 0.750000 0.47480(9) 0.0308(4) Uani 1 2 d S T P . .
H12A H 0.663637 0.814860 0.447204 0.037 Uiso 0.5 1 calc R U P . .
H12B H 0.663637 0.685140 0.447204 0.037 Uiso 0.5 1 calc R U P . .
C13 C 0.67183(15) 0.750000 0.56375(9) 0.0329(4) Uani 1 2 d S T P . .
H13 H 0.767754 0.749999 0.566549 0.040 Uiso 1 2 calc R U P . .
C14 C 0.61993(12) 0.85122(10) 0.60597(7) 0.0345(3) Uani 1 1 d . . . . .
H14A H 0.648379 0.852052 0.662940 0.041 Uiso 1 1 calc R U . . .
H14B H 0.653815 0.916804 0.579172 0.041 Uiso 1 1 calc R U . . .
C15 C 0.47345(11) 0.85104(9) 0.60214(6) 0.0305(3) Uani 1 1 d . . . . .
H15 H 0.439274 0.916923 0.629725 0.037 Uiso 1 1 calc R U . . .
C16 C 0.43061(10) 0.85088(8) 0.51341(6) 0.0258(2) Uani 1 1 d . . . . .
H16A H 0.335659 0.851605 0.510481 0.031 Uiso 1 1 calc R U . . .
H16B H 0.463143 0.916604 0.486141 0.031 Uiso 1 1 calc R U . . .
C17 C 0.42152(17) 0.750000 0.64361(9) 0.0332(4) Uani 1 2 d S T P . .
H17A H 0.326523 0.750000 0.641253 0.040 Uiso 1 2 calc R U P . .
H17B H 0.447557 0.750001 0.701038 0.040 Uiso 1 2 calc R U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 N1 C2 113.68(11) . . ?
C1 N1 C4 124.04(11) . . ?
C2 N1 C4 122.27(11) . . ?
C1 N2 C3 112.47(11) . . ?
C1 N2 C11 125.18(11) . . ?
C3 N2 C11 122.35(11) . . ?
N2 C1 N1 101.48(11) . . ?
C3 C2 N1 105.33(12) . . ?
C3 C2 H2 127.3 . . ?
N1 C2 H2 127.3 . . ?
C2 C3 N2 107.03(12) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C5 C4 C5 122.57(12) 7_575 . ?
C5 C4 N1 118.70(6) 7_575 . ?
C5 C4 N1 118.70(6) . . ?
C6 C5 C4 117.51(9) . . ?
C6 C5 C8 120.59(9) . . ?
C4 C5 C8 121.89(9) . . ?
C7 C6 C5 121.25(10) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C6 119.90(13) . 7_575 ?
C6 C7 H7 120.1 . . ?
C6 C7 H7 120.1 7_575 . ?
C5 C8 C9 111.62(9) . . ?
C5 C8 C10 110.27(9) . . ?
C9 C8 C10 111.80(10) . . ?
C5 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C10 C8 H8 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 110.47(11) . . ?
N2 C11 C16 109.31(7) . . ?
C12 C11 C16 109.38(8) . . ?
N2 C11 C16 109.31(7) . 7_575 ?
C12 C11 C16 109.38(8) . 7_575 ?
C16 C11 C16 108.96(11) . 7_575 ?
C11 C12 C13 109.21(12) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C14 109.53(13) . 7_575 ?
C14 C13 C12 109.65(8) . . ?
C14 C13 C12 109.65(8) 7_575 . ?
C14 C13 H13 109.3 . . ?
C14 C13 H13 109.3 7_575 . ?
C12 C13 H13 109.3 . . ?
C15 C14 C13 109.39(10) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C17 C15 C14 109.67(10) . . ?
C17 C15 C16 109.11(10) . . ?
C14 C15 C16 109.25(9) . . ?
C17 C15 H15 109.6 . . ?
C14 C15 H15 109.6 . . ?
C16 C15 H15 109.6 . . ?
C11 C16 C15 109.91(9) . . ?
C11 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C11 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C15 C17 C15 110.02(13) . 7_575 ?
C15 C17 H17A 109.7 . . ?
C15 C17 H17A 109.7 7_575 . ?
C15 C17 H17B 109.7 . . ?
C15 C17 H17B 109.7 7_575 . ?
H17A C17 H17B 108.2 . . ?
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
N1 C1 1.3710(18) . ?
N1 C2 1.3852(17) . ?
N1 C4 1.4352(17) . ?
N2 C1 1.3627(18) . ?
N2 C3 1.3933(18) . ?
N2 C11 1.4765(17) . ?
C2 C3 1.342(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.3986(12) 7_575 ?
C4 C5 1.3986(12) . ?
C5 C6 1.3973(14) . ?
C5 C8 1.5176(14) . ?
C6 C7 1.3833(12) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.5251(17) . ?
C8 C10 1.5280(16) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5310(19) . ?
C11 C16 1.5332(12) . ?
C11 C16 1.5332(12) 7_575 ?
C12 C13 1.540(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5329(15) . ?
C13 C14 1.5329(15) 7_575 ?
C13 H13 1.0000 . ?
C14 C15 1.5266(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.5256(14) . ?
C15 C16 1.5374(14) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
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
C3 N2 C1 N1 0.000(0) . . . . ?
C11 N2 C1 N1 180.000(0) . . . . ?
C2 N1 C1 N2 0.000(0) . . . . ?
C4 N1 C1 N2 180.000(0) . . . . ?
C1 N1 C2 C3 0.000(0) . . . . ?
C4 N1 C2 C3 180.000(0) . . . . ?
N1 C2 C3 N2 0.000(0) . . . . ?
C1 N2 C3 C2 0.000(0) . . . . ?
C11 N2 C3 C2 180.000(0) . . . . ?
C1 N1 C4 C5 -90.85(10) . . . 7_575 ?
C2 N1 C4 C5 89.15(10) . . . 7_575 ?
C1 N1 C4 C5 90.84(10) . . . . ?
C2 N1 C4 C5 -89.16(10) . . . . ?
C5 C4 C5 C6 -1.0(2) 7_575 . . . ?
N1 C4 C5 C6 177.22(10) . . . . ?
C5 C4 C5 C8 -179.76(8) 7_575 . . . ?
N1 C4 C5 C8 -1.52(17) . . . . ?
C4 C5 C6 C7 0.18(16) . . . . ?
C8 C5 C6 C7 178.94(11) . . . . ?
C5 C6 C7 C6 0.6(2) . . . 7_575 ?
C6 C5 C8 C9 54.56(13) . . . . ?
C4 C5 C8 C9 -126.73(11) . . . . ?
C6 C5 C8 C10 -70.34(13) . . . . ?
C4 C5 C8 C10 108.37(12) . . . . ?
C1 N2 C11 C12 0.000(0) . . . . ?
C3 N2 C11 C12 180.000(0) . . . . ?
C1 N2 C11 C16 120.41(8) . . . . ?
C3 N2 C11 C16 -59.59(8) . . . . ?
C1 N2 C11 C16 -120.41(8) . . . 7_575 ?
C3 N2 C11 C16 59.59(8) . . . 7_575 ?
N2 C11 C12 C13 180.000(0) . . . . ?
C16 C11 C12 C13 59.63(7) . . . . ?
C16 C11 C12 C13 -59.63(7) 7_575 . . . ?
C11 C12 C13 C14 -60.15(9) . . . . ?
C11 C12 C13 C14 60.15(9) . . . 7_575 ?
C14 C13 C14 C15 -59.92(14) 7_575 . . . ?
C12 C13 C14 C15 60.44(13) . . . . ?
C13 C14 C15 C17 59.55(12) . . . . ?
C13 C14 C15 C16 -60.00(12) . . . . ?
N2 C11 C16 C15 179.06(9) . . . . ?
C12 C11 C16 C15 -59.87(12) . . . . ?
C16 C11 C16 C15 59.65(14) 7_575 . . . ?
C17 C15 C16 C11 -59.92(12) . . . . ?
C14 C15 C16 C11 59.97(12) . . . . ?
C14 C15 C17 C15 -59.46(15) . . . 7_575 ?
C16 C15 C17 C15 60.17(16) . . . 7_575 ?
