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#$Date: 2018-02-08 02:18:44 +0200 (Thu, 08 Feb 2018) $
#$Revision: 206274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127170.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_4127170
loop_
_publ_author_name
'Kiel, Gavin R.'
'Samkian, Adrian E.'
'Nicolay, Amélie'
'Witzke, Ryan J.'
'Tilley, T. Don'
_publ_section_title
;
 Titanocene-Mediated Dinitrile Coupling: A Divergent Route to
 Nitrogen-Containing Polycyclic Aromatic Hydrocarbons.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b13823
_journal_year                    2018
_chemical_formula_sum            'C19 H22 Cl4 N2 Sn2'
_chemical_formula_weight         657.56
_chemical_name_common            GK2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.066(2)
_cell_angle_beta                 78.635(2)
_cell_angle_gamma                84.963(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2579(3)
_cell_length_b                   12.5778(5)
_cell_length_c                   12.8986(5)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.58
_cell_volume                     1123.94(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (SIR-2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25445
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.557
_diffrn_reflns_theta_min         1.648
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.705
_exptl_absorpt_correction_T_max  0.4403
_exptl_absorpt_correction_T_min  0.3698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.646
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0299
_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)+(0.0351P)²+2.2295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3628
_reflns_number_total             4181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b13823_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4127170
_shelx_shelxl_version_number     2014/7
_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   0.855
_shelx_estimated_absorpt_t_max   0.948
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
C1 C 1.0465(6) 0.4385(3) 0.7486(3) 0.0234(9) Uani 1 1 d . .
H1A H 0.9715 0.4168 0.8213 0.035 Uiso 1 1 calc R U
H1B H 1.1176 0.5023 0.7452 0.035 Uiso 1 1 calc R U
H1C H 1.1340 0.3780 0.7324 0.035 Uiso 1 1 calc R U
C2 C 0.6276(6) 0.4019(3) 0.6148(3) 0.0222(9) Uani 1 1 d . .
H2A H 0.6601 0.3696 0.5508 0.033 Uiso 1 1 calc R U
H2B H 0.5236 0.4564 0.6060 0.033 Uiso 1 1 calc R U
H2C H 0.5893 0.3446 0.6791 0.033 Uiso 1 1 calc R U
C3 C 0.6680(6) 0.6917(3) 0.5901(3) 0.0149(8) Uani 1 1 d . .
C4 C 0.4973(6) 0.7583(3) 0.5726(3) 0.0143(8) Uani 1 1 d . .
C5 C 0.3263(6) 0.7289(3) 0.6412(3) 0.0172(8) Uani 1 1 d . .
H5 H 0.3250 0.6698 0.7019 0.021 Uiso 1 1 calc R U
C6 C 0.1591(6) 0.7847(3) 0.6219(3) 0.0205(9) Uani 1 1 d . .
H6 H 0.0438 0.7657 0.6696 0.025 Uiso 1 1 calc R U
C7 C 0.1635(6) 0.8690(3) 0.5310(3) 0.0214(9) Uani 1 1 d . .
H7 H 0.0497 0.9078 0.5170 0.026 Uiso 1 1 calc R U
C8 C 0.3305(6) 0.8975(3) 0.4606(3) 0.0191(9) Uani 1 1 d . .
H8 H 0.3294 0.9554 0.3992 0.023 Uiso 1 1 calc R U
C9 C 0.4992(6) 0.8424(3) 0.4787(3) 0.0158(8) Uani 1 1 d . .
C10 C 0.6790(6) 0.8662(3) 0.4030(3) 0.0161(8) Uani 1 1 d . .
C11 C 0.7030(6) 0.9652(3) 0.3276(3) 0.0201(9) Uani 1 1 d . .
H11 H 0.6015 1.0182 0.3243 0.024 Uiso 1 1 calc R U
C12 C 0.8725(6) 0.9868(3) 0.2575(3) 0.0221(9) Uani 1 1 d . .
H12 H 0.8868 1.0550 0.2076 0.027 Uiso 1 1 calc R U
C13 C 1.0222(6) 0.9099(3) 0.2596(3) 0.0208(9) Uani 1 1 d . .
H13 H 1.1382 0.9255 0.2114 0.025 Uiso 1 1 calc R U
C14 C 1.0014(6) 0.8100(3) 0.3324(3) 0.0186(9) Uani 1 1 d . .
H14 H 1.1025 0.7566 0.3332 0.022 Uiso 1 1 calc R U
C15 C 0.8305(6) 0.7882(3) 0.4046(3) 0.0155(8) Uani 1 1 d . .
C16 C 0.8165(5) 0.6866(3) 0.4886(3) 0.0142(8) Uani 1 1 d . .
C17 C 0.8425(6) 0.6163(3) 0.9178(3) 0.0207(9) Uani 1 1 d . .
H17A H 0.8295 0.6576 0.9751 0.031 Uiso 1 1 calc R U
H17B H 0.9554 0.6380 0.8637 0.031 Uiso 1 1 calc R U
H17C H 0.8537 0.5380 0.9491 0.031 Uiso 1 1 calc R U
C18 C 0.3296(6) 0.7051(3) 0.9066(3) 0.0239(9) Uani 1 1 d . .
H18A H 0.2470 0.6433 0.9310 0.036 Uiso 1 1 calc R U
H18B H 0.2805 0.7596 0.8503 0.036 Uiso 1 1 calc R U
H18C H 0.3347 0.7381 0.9679 0.036 Uiso 1 1 calc R U
C19 C 0.7227(7) 0.9192(4) 0.0297(4) 0.0314(11) Uani 1 1 d . .
H19A H 0.6923 0.9388 -0.0440 0.038 Uiso 1 1 calc R U
H19B H 0.7251 0.9876 0.0551 0.038 Uiso 1 1 calc R U
N1 N 0.7010(5) 0.6314(2) 0.6794(2) 0.0156(7) Uani 1 1 d . .
N2 N 0.9255(5) 0.6011(2) 0.4889(2) 0.0153(7) Uani 1 1 d . .
Cl1 Cl 0.52332(16) 0.45407(7) 0.86470(8) 0.0250(2) Uani 1 1 d . .
Cl2 Cl 0.69182(14) 0.84999(7) 0.76992(8) 0.0205(2) Uani 1 1 d . .
Cl3 Cl 0.5461(2) 0.83702(10) 0.11703(11) 0.0445(3) Uani 1 1 d . .
Cl4 Cl 0.94638(17) 0.85139(9) 0.02454(9) 0.0319(3) Uani 1 1 d . .
Sn1 Sn 0.86553(4) 0.47824(2) 0.63369(2) 0.01441(9) Uani 1 1 d . .
Sn2 Sn 0.60309(4) 0.64951(2) 0.84319(2) 0.01480(9) Uani 1 1 d . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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
Sn1 C1 H1A 109.5 . .
Sn1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
Sn1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
Sn1 C2 H2A 109.5 . .
Sn1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
Sn1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 C4 127.1(3) . .
N1 C3 C16 116.7(3) . .
C4 C3 C16 116.0(3) . .
C5 C4 C9 119.8(4) . .
C5 C4 C3 119.3(3) . .
C9 C4 C3 120.2(3) . .
C6 C5 C4 120.9(4) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C7 118.6(4) . .
C5 C6 H6 120.7 . .
C7 C6 H6 120.7 . .
C8 C7 C6 121.4(4) . .
C8 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
C7 C8 C9 120.8(4) . .
C7 C8 H8 119.6 . .
C9 C8 H8 119.6 . .
C8 C9 C4 118.3(4) . .
C8 C9 C10 122.7(3) . .
C4 C9 C10 118.9(4) . .
C11 C10 C15 118.4(4) . .
C11 C10 C9 121.4(4) . .
C15 C10 C9 120.2(3) . .
C12 C11 C10 120.9(4) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C13 120.6(3) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C14 C13 C12 119.8(4) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C13 C14 C15 119.8(4) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C14 C15 C10 120.6(3) . .
C14 C15 C16 119.2(4) . .
C10 C15 C16 120.1(3) . .
N2 C16 C15 126.7(3) . .
N2 C16 C3 118.1(3) . .
C15 C16 C3 114.8(3) . .
Sn2 C17 H17A 109.5 . .
Sn2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
Sn2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
Sn2 C18 H18A 109.5 . .
Sn2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
Sn2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
Cl4 C19 Cl3 111.6(2) . .
Cl4 C19 H19A 109.3 . .
Cl3 C19 H19A 109.3 . .
Cl4 C19 H19B 109.3 . .
Cl3 C19 H19B 109.3 . .
H19A C19 H19B 108.0 . .
C3 N1 Sn2 130.2(3) . .
C3 N1 Sn1 105.6(2) . .
Sn2 N1 Sn1 123.73(14) . .
C16 N2 Sn1 113.7(2) . .
C16 N2 Sn1 138.2(3) . 2_766
Sn1 N2 Sn1 106.73(13) . 2_766
C1 Sn1 C2 132.44(16) . .
C1 Sn1 N2 122.65(15) . .
C2 Sn1 N2 104.26(14) . .
C1 Sn1 N2 91.82(14) . 2_766
C2 Sn1 N2 94.62(14) . 2_766
N2 Sn1 N2 73.27(13) . 2_766
C1 Sn1 N1 101.89(14) . .
C2 Sn1 N1 95.82(14) . .
N2 Sn1 N1 76.43(11) . .
N2 Sn1 N1 149.53(10) 2_766 .
C18 Sn2 C17 128.73(16) . .
C18 Sn2 N1 125.63(15) . .
C17 Sn2 N1 105.36(14) . .
C18 Sn2 Cl1 96.02(12) . .
C17 Sn2 Cl1 96.87(11) . .
N1 Sn2 Cl1 80.97(8) . .
C18 Sn2 Cl2 88.96(12) . .
C17 Sn2 Cl2 90.55(11) . .
N1 Sn2 Cl2 85.03(8) . .
Cl1 Sn2 Cl2 165.47(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 Sn1 2.120(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 Sn1 2.127(4) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 N1 1.283(5) .
C3 C4 1.459(5) .
C3 C16 1.532(5) .
C4 C5 1.401(5) .
C4 C9 1.417(5) .
C5 C6 1.385(6) .
C5 H5 0.9500 .
C6 C7 1.390(6) .
C6 H6 0.9500 .
C7 C8 1.385(6) .
C7 H7 0.9500 .
C8 C9 1.388(6) .
C8 H8 0.9500 .
C9 C10 1.477(5) .
C10 C11 1.398(5) .
C10 C15 1.408(6) .
C11 C12 1.384(6) .
C11 H11 0.9500 .
C12 C13 1.390(6) .
C12 H12 0.9500 .
C13 C14 1.390(5) .
C13 H13 0.9500 .
C14 C15 1.405(5) .
C14 H14 0.9500 .
C15 C16 1.476(5) .
C16 N2 1.278(5) .
C17 Sn2 2.114(4) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 Sn2 2.114(4) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 Cl4 1.763(5) .
C19 Cl3 1.767(5) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
N1 Sn2 2.149(3) .
N1 Sn1 2.304(3) .
N2 Sn1 2.138(3) .
N2 Sn1 2.300(3) 2_766
Cl1 Sn2 2.5171(9) .
Cl2 Sn2 2.5778(9) .
Sn1 N2 2.300(3) 2_766
