#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/18/4101873.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_4101873
loop_
_publ_author_name
'Stéphane Beaumont'
'Elizabeth A. Ilardi'
'Lucas R. Monroe'
'Armen Zakarian'
_publ_section_title
;
 Valence Tautomerism in Titanium Enolates: Catalytic Radical
 Haloalkylation and Application in the Total Synthesis of Neodysidenin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1482
_journal_page_last               1483
_journal_paper_doi               10.1021/ja910154f
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H14 Cl3 N O3'
_chemical_formula_weight         350.61
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.900(2)
_cell_length_b                   11.571(5)
_cell_length_c                   23.062(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1574.4(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12539
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  0.276
_exptl_absorpt_correction_T_min  0.216
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_coef       0.090(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          4.392
_refine_ls_shift/su_mean         0.051
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0580P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2763
_reflns_number_total             3191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910154f_si_003.cif
_cod_data_source_block           s102109m
_cod_original_cell_volume        1574.3(11)
_cod_database_code               4101873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1902(4) 0.64684(19) 0.72077(10) 0.0491(5) Uani 1 1 d . . .
C2 C 0.1099(4) 0.62709(18) 0.65789(9) 0.0445(5) Uani 1 1 d . . .
H2 H 0.232(5) 0.588(2) 0.6367(11) 0.053 Uiso 1 1 calc . . .
C3 C -0.1023(6) 0.5517(2) 0.65438(13) 0.0685(8) Uani 1 1 d . . .
H3A H -0.2256 0.5899 0.6736 0.103 Uiso 1 1 calc R . .
H3B H -0.0735 0.4788 0.6729 0.103 Uiso 1 1 calc R . .
H3C H -0.1411 0.5390 0.6145 0.103 Uiso 1 1 calc R . .
C4 C 0.0656(4) 0.74413(17) 0.62868(9) 0.0423(5) Uani 1 1 d . . .
C5 C 0.3909(5) 0.7280(2) 0.56000(9) 0.0503(5) Uani 1 1 d . . .
C6 C 0.4125(7) 0.9154(2) 0.53006(14) 0.0812(10) Uani 1 1 d . . .
H6A H 0.3611 0.9455 0.4931 0.097 Uiso 1 1 calc R . .
H6B H 0.5313 0.9655 0.5447 0.097 Uiso 1 1 calc R . .
C7 C 0.2175(5) 0.91041(18) 0.57258(9) 0.0444(5) Uani 1 1 d . . .
H7 H 0.074(5) 0.924(2) 0.5524(11) 0.053 Uiso 1 1 calc . . .
C8 C 0.2434(6) 0.99485(19) 0.62271(10) 0.0605(6) Uani 1 1 d . . .
H8A H 0.1167 0.9855 0.6491 0.073 Uiso 1 1 calc R . .
H8B H 0.3811 0.9769 0.6438 0.073 Uiso 1 1 calc R . .
C9 C 0.2528(5) 1.11942(18) 0.60239(9) 0.0518(6) Uani 1 1 d . . .
C10 C 0.0790(6) 1.1681(2) 0.57020(13) 0.0666(7) Uani 1 1 d . . .
H10 H -0.0449 1.1227 0.5600 0.080 Uiso 1 1 calc R . .
C11 C 0.0855(7) 1.2822(2) 0.55294(14) 0.0781(8) Uani 1 1 d . . .
H11 H -0.0320 1.3129 0.5309 0.094 Uiso 1 1 calc R . .
C12 C 0.2646(8) 1.3495(2) 0.56828(14) 0.0808(10) Uani 1 1 d . . .
H12 H 0.2684 1.4267 0.5570 0.097 Uiso 1 1 calc R . .
C13 C 0.4378(8) 1.3053(3) 0.59993(15) 0.0850(10) Uani 1 1 d . . .
H13 H 0.5600 1.3516 0.6103 0.102 Uiso 1 1 calc R . .
C14 C 0.4304(6) 1.1889(2) 0.61677(12) 0.0697(7) Uani 1 1 d . . .
H14 H 0.5496 1.1584 0.6383 0.084 Uiso 1 1 calc R . .
Cl1 Cl -0.02075(13) 0.70245(7) 0.76713(3) 0.0744(2) Uani 1 1 d . . .
Cl2 Cl 0.42353(12) 0.74298(7) 0.72172(3) 0.0772(3) Uani 1 1 d . . .
Cl3 Cl 0.28302(18) 0.51172(7) 0.74964(4) 0.0855(3) Uani 1 1 d . . .
N N 0.2311(3) 0.78910(14) 0.59159(7) 0.0417(4) Uani 1 1 d . . .
O1 O -0.1038(3) 0.79970(15) 0.63817(8) 0.0608(5) Uani 1 1 d . . .
O2 O 0.4335(4) 0.62714(15) 0.56112(8) 0.0698(5) Uani 1 1 d . . .
O3 O 0.4955(4) 0.80045(15) 0.52334(8) 0.0656(5) 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'
O O 0.0106 0.0060 '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'
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
C2 C1 Cl1 114.06(17) . . ?
C2 C1 Cl2 110.08(15) . . ?
Cl1 C1 Cl2 108.20(13) . . ?
C2 C1 Cl3 108.37(16) . . ?
Cl1 C1 Cl3 108.07(12) . . ?
Cl2 C1 Cl3 107.89(13) . . ?
C3 C2 C4 109.9(2) . . ?
C3 C2 C1 112.69(19) . . ?
C4 C2 C1 109.53(17) . . ?
C3 C2 H2 108.8(15) . . ?
C4 C2 H2 108.3(15) . . ?
C1 C2 H2 107.5(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N 119.36(19) . . ?
O1 C4 C2 122.1(2) . . ?
N C4 C2 118.54(19) . . ?
O2 C5 O3 121.9(2) . . ?
O2 C5 N 129.1(2) . . ?
O3 C5 N 109.0(2) . . ?
O3 C6 C7 107.2(2) . . ?
O3 C6 H6A 110.3 . . ?
C7 C6 H6A 110.3 . . ?
O3 C6 H6B 110.3 . . ?
C7 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
N C7 C6 100.86(19) . . ?
N C7 C8 112.36(17) . . ?
C6 C7 C8 113.1(2) . . ?
N C7 H7 102.7(16) . . ?
C6 C7 H7 117.1(16) . . ?
C8 C7 H7 109.9(16) . . ?
C9 C8 C7 112.29(18) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 117.4(2) . . ?
C14 C9 C8 120.9(3) . . ?
C10 C9 C8 121.6(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.5(3) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C5 N C4 127.35(18) . . ?
C5 N C7 111.53(17) . . ?
C4 N C7 119.92(18) . . ?
C5 O3 C6 110.9(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
C1 C2 1.543(3) . ?
C1 Cl1 1.762(2) . ?
C1 Cl2 1.770(2) . ?
C1 Cl3 1.785(2) . ?
C2 C3 1.528(4) . ?
C2 C4 1.535(3) . ?
C2 H2 0.97(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O1 1.209(3) . ?
C4 N 1.398(3) . ?
C5 O2 1.194(3) . ?
C5 O3 1.341(3) . ?
C5 N 1.386(3) . ?
C6 O3 1.426(3) . ?
C6 C7 1.512(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N 1.473(3) . ?
C7 C8 1.521(3) . ?
C7 H7 0.94(3) . ?
C8 C9 1.517(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.361(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
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
Cl1 C1 C2 C3 -54.0(2) . . . . ?
Cl2 C1 C2 C3 -175.82(18) . . . . ?
Cl3 C1 C2 C3 66.4(2) . . . . ?
Cl1 C1 C2 C4 68.7(2) . . . . ?
Cl2 C1 C2 C4 -53.1(2) . . . . ?
Cl3 C1 C2 C4 -170.89(16) . . . . ?
C3 C2 C4 O1 46.8(3) . . . . ?
C1 C2 C4 O1 -77.5(3) . . . . ?
C3 C2 C4 N -135.5(2) . . . . ?
C1 C2 C4 N 100.2(2) . . . . ?
O3 C6 C7 N 7.0(3) . . . . ?
O3 C6 C7 C8 127.2(3) . . . . ?
N C7 C8 C9 174.3(2) . . . . ?
C6 C7 C8 C9 61.0(3) . . . . ?
C7 C8 C9 C14 -124.2(3) . . . . ?
C7 C8 C9 C10 57.8(4) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 178.4(3) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C10 C9 C14 C13 0.2(4) . . . . ?
C8 C9 C14 C13 -177.8(3) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
O2 C5 N C4 -6.7(4) . . . . ?
O3 C5 N C4 170.8(2) . . . . ?
O2 C5 N C7 -174.0(3) . . . . ?
O3 C5 N C7 3.5(3) . . . . ?
O1 C4 N C5 -155.8(2) . . . . ?
C2 C4 N C5 26.4(3) . . . . ?
O1 C4 N C7 10.5(3) . . . . ?
C2 C4 N C7 -167.19(19) . . . . ?
C6 C7 N C5 -6.5(3) . . . . ?
C8 C7 N C5 -127.1(2) . . . . ?
C6 C7 N C4 -174.9(2) . . . . ?
C8 C7 N C4 64.5(3) . . . . ?
O2 C5 O3 C6 179.2(3) . . . . ?
N C5 O3 C6 1.5(3) . . . . ?
C7 C6 O3 C5 -5.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660084
