#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:51:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178629 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/40/4074093.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_4074093
loop_
_publ_author_name
'Wu, Chun Ji'
'Lee, Sang Hoon'
'Yun, Hoseop'
'Lee, Bun Yeoul'
_publ_section_title
;
 Ortho Lithiation of Tetrahydroquinoline Derivatives and Its Use for the
 Facile Construction of Polymerization Catalysts
;
_journal_issue                   27
_journal_name_full               Organometallics
_journal_page_first              6685
_journal_paper_doi               10.1021/om7010084
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C20 H27 N Ti'
_chemical_formula_weight         329.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2007-07-11 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.824(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.465(5)
_cell_length_b                   8.585(2)
_cell_length_c                   16.138(4)
_cell_measurement_reflns_used    12881
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.595
_cell_measurement_theta_min      3.15
_cell_volume                     1788.4(9)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 2005)'
_computing_data_reduction        RAPID-AUTO
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-axis Rapid'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16978
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.8007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                3088
_reflns_number_total             4103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om7010084-file001.cif
_cod_data_source_block           l
_cod_original_cell_volume        1788.3(9)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4074093
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
Ti1 Ti 0.36751(3) 0.25758(4) 0.69501(2) 0.01887(11) Uani 1 1 d
N1 N 0.37646(13) 0.41657(19) 0.78278(11) 0.0212(4) Uani 1 1 d
C1 C 0.54076(14) 0.3347(2) 0.76540(13) 0.0193(4) Uani 1 1 d
C2 C 0.50371(15) 0.3596(2) 0.66845(14) 0.0212(4) Uani 1 1 d
C3 C 0.47737(15) 0.2132(2) 0.62390(14) 0.0214(4) Uani 1 1 d
C4 C 0.49877(15) 0.0962(2) 0.69307(13) 0.0200(4) Uani 1 1 d
C5 C 0.53815(15) 0.1713(2) 0.78061(13) 0.0200(4) Uani 1 1 d
C6 C 0.4928(2) 0.5161(2) 0.62385(18) 0.0297(5) Uani 1 1 d
C7 C 0.44000(19) 0.1854(3) 0.52175(16) 0.0284(5) Uani 1 1 d
C8 C 0.48699(18) -0.0763(2) 0.67626(16) 0.0265(5) Uani 1 1 d
C9 C 0.56901(18) 0.0965(3) 0.87297(15) 0.0264(4) Uani 1 1 d
C10 C 0.55641(15) 0.4598(2) 0.83392(13) 0.0194(4) Uani 1 1 d
C11 C 0.64792(16) 0.5391(2) 0.88551(14) 0.0239(4) Uani 1 1 d
C12 C 0.65008(17) 0.6596(2) 0.94407(15) 0.0253(4) Uani 1 1 d
C13 C 0.56036(17) 0.7003(2) 0.94972(14) 0.0233(4) Uani 1 1 d
C14 C 0.46700(16) 0.6249(2) 0.89811(13) 0.0215(4) Uani 1 1 d
C15 C 0.46516(15) 0.5018(2) 0.83988(13) 0.0195(4) Uani 1 1 d
C16 C 0.28247(16) 0.4504(3) 0.79407(16) 0.0265(4) Uani 1 1 d
C17 C 0.27409(18) 0.6231(3) 0.81127(16) 0.0294(5) Uani 1 1 d
C18 C 0.36765(17) 0.6729(3) 0.90020(15) 0.0272(5) Uani 1 1 d
C19 C 0.2500(2) 0.3225(3) 0.56403(17) 0.0367(5) Uani 1 1 d
C20 C 0.3003(2) 0.0628(3) 0.7256(2) 0.0425(6) Uani 1 1 d
H1 H 0.5608(17) 0.785(2) 0.9895(15) 0.023(6) Uiso 1 1 d
H2 H 0.2693(17) 0.681(3) 0.7607(15) 0.022(6) Uiso 1 1 d
H3 H 0.2241(18) 0.413(2) 0.7381(15) 0.023(6) Uiso 1 1 d
H4 H 0.710(2) 0.711(3) 0.9769(17) 0.035(7) Uiso 1 1 d
H5 H 0.426(2) -0.097(3) 0.6252(17) 0.032(6) Uiso 1 1 d
H6 H 0.3650(17) 0.630(3) 0.9534(16) 0.028(6) Uiso 1 1 d
H7 H 0.7083(19) 0.511(3) 0.8812(15) 0.029(6) Uiso 1 1 d
H8 H 0.2855(19) 0.390(3) 0.8473(17) 0.036(7) Uiso 1 1 d
H9 H 0.4842(19) -0.133(3) 0.7277(17) 0.038(7) Uiso 1 1 d
H10 H 0.3674(18) 0.788(3) 0.9077(16) 0.029(6) Uiso 1 1 d
H11 H 0.211(2) 0.643(3) 0.8124(16) 0.034(6) Uiso 1 1 d
H12 H 0.395(2) 0.267(3) 0.4859(17) 0.031(6) Uiso 1 1 d
H13 H 0.239(2) 0.100(3) 0.7266(19) 0.052(8) Uiso 1 1 d
H14 H 0.5426(19) -0.123(3) 0.6653(15) 0.031(6) Uiso 1 1 d
H15 H 0.557(2) 0.161(3) 0.9131(18) 0.044(7) Uiso 1 1 d
H16 H 0.446(2) 0.517(3) 0.559(2) 0.046(8) Uiso 1 1 d
H17 H 0.234(2) 0.236(3) 0.520(2) 0.052(8) Uiso 1 1 d
H18 H 0.531(2) 0.005(3) 0.8672(19) 0.049(8) Uiso 1 1 d
H19 H 0.400(2) 0.095(3) 0.5012(18) 0.045(7) Uiso 1 1 d
H20 H 0.642(2) 0.066(3) 0.9031(17) 0.041(7) Uiso 1 1 d
H21 H 0.497(3) 0.177(3) 0.509(2) 0.060(9) Uiso 1 1 d
H22 H 0.473(2) 0.592(3) 0.6548(19) 0.050(8) Uiso 1 1 d
H23 H 0.188(2) 0.345(3) 0.5700(19) 0.056(8) Uiso 1 1 d
H24 H 0.260(3) 0.407(4) 0.536(2) 0.070(10) Uiso 1 1 d
H25 H 0.556(3) 0.550(4) 0.628(2) 0.066(9) Uiso 1 1 d
H26 H 0.281(3) -0.014(4) 0.676(2) 0.085(12) Uiso 1 1 d
H27 H 0.339(3) 0.016(4) 0.783(3) 0.082(12) 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
Ti Ti 0.2780 0.4460 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0030 0.0020 '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 0.0060 0.0030 '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
N1 Ti1 C20 105.97(10)
N1 Ti1 C19 107.84(9)
C20 Ti1 C19 101.38(13)
N1 Ti1 C1 74.94(7)
C20 Ti1 C1 128.36(10)
C19 Ti1 C1 128.14(9)
N1 Ti1 C5 95.00(7)
C20 Ti1 C5 94.94(10)
C19 Ti1 C5 146.73(9)
C1 Ti1 C5 35.58(6)
N1 Ti1 C4 129.55(7)
C20 Ti1 C4 89.80(9)
C19 Ti1 C4 115.59(9)
C1 Ti1 C4 58.63(7)
C5 Ti1 C4 35.09(7)
N1 Ti1 C2 94.91(7)
C20 Ti1 C2 148.06(9)
C19 Ti1 C2 94.65(10)
C1 Ti1 C2 35.25(7)
C5 Ti1 C2 58.74(7)
C4 Ti1 C2 58.30(7)
N1 Ti1 C3 129.12(7)
C20 Ti1 C3 117.88(9)
C19 Ti1 C3 88.30(9)
C1 Ti1 C3 58.29(7)
C5 Ti1 C3 58.43(7)
C4 Ti1 C3 35.10(7)
C2 Ti1 C3 34.68(6)
C15 N1 C16 115.85(16)
C15 N1 Ti1 126.19(12)
C16 N1 Ti1 117.93(13)
C2 C1 C5 108.12(16)
C2 C1 C10 124.43(17)
C5 C1 C10 126.18(17)
C2 C1 Ti1 73.64(11)
C5 C1 Ti1 72.48(11)
C10 C1 Ti1 109.72(12)
C3 C2 C1 107.88(17)
C3 C2 C6 127.41(19)
C1 C2 C6 124.69(18)
C3 C2 Ti1 72.98(11)
C1 C2 Ti1 71.11(10)
C6 C2 Ti1 120.23(14)
C2 C3 C4 108.33(17)
C2 C3 C7 125.48(18)
C4 C3 C7 126.07(18)
C2 C3 Ti1 72.34(11)
C4 C3 Ti1 72.01(10)
C7 C3 Ti1 124.58(15)
C5 C4 C3 107.88(16)
C5 C4 C8 126.18(18)
C3 C4 C8 125.86(18)
C5 C4 Ti1 71.58(11)
C3 C4 Ti1 72.89(11)
C8 C4 Ti1 123.68(14)
C4 C5 C1 107.78(17)
C4 C5 C9 127.12(18)
C1 C5 C9 125.08(18)
C4 C5 Ti1 73.32(11)
C1 C5 Ti1 71.94(11)
C9 C5 Ti1 119.07(14)
C11 C10 C15 120.22(18)
C11 C10 C1 125.96(17)
C15 C10 C1 113.72(17)
C10 C11 C12 119.76(19)
C13 C12 C11 119.8(2)
C12 C13 C14 122.01(19)
C13 C14 C15 118.16(18)
C13 C14 C18 122.54(18)
C15 C14 C18 119.27(18)
N1 C15 C14 124.56(17)
N1 C15 C10 115.37(16)
C14 C15 C10 120.04(18)
N1 C16 C17 111.50(17)
C16 C17 C18 109.57(18)
C14 C18 C17 110.61(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ti1 N1 1.9288(16)
Ti1 C20 2.102(2)
Ti1 C19 2.104(3)
Ti1 C1 2.332(2)
Ti1 C5 2.339(2)
Ti1 C4 2.3619(19)
Ti1 C2 2.365(2)
Ti1 C3 2.3734(19)
N1 C15 1.401(2)
N1 C16 1.480(2)
C1 C2 1.423(3)
C1 C5 1.427(3)
C1 C10 1.484(3)
C2 C3 1.412(3)
C2 C6 1.498(3)
C3 C4 1.428(3)
C3 C7 1.504(3)
C4 C5 1.418(3)
C4 C8 1.501(3)
C5 C9 1.494(3)
C10 C11 1.383(3)
C10 C15 1.413(3)
C11 C12 1.392(3)
C12 C13 1.386(3)
C13 C14 1.386(3)
C14 C15 1.406(3)
C14 C18 1.510(3)
C16 C17 1.523(3)
C17 C18 1.524(3)
