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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/18/4101874.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_4101874
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            'C11 H15 Cl6 N O3'
_chemical_formula_weight         421.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 98.187(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.887(4)
_cell_length_b                   11.304(7)
_cell_length_c                   13.230(8)
_cell_measurement_temperature    293(2)
_cell_volume                     871.4(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6504
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  0.319
_exptl_absorpt_correction_T_min  0.215
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2448
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910154f_si_004.cif
_cod_data_source_block           s112509
_cod_original_cell_volume        871.4(9)
_cod_database_code               4101874
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 -0.0235(7) 0.8544(4) 0.3147(3) 0.0443(10) Uani 1 1 d . . .
C2 C 0.0367(7) 0.9834(4) 0.3366(3) 0.0415(9) Uani 1 1 d . . .
H2 H 0.195(7) 0.995(4) 0.324(3) 0.050 Uiso 1 1 calc . . .
C3 C 0.0272(7) 1.0168(4) 0.4491(3) 0.0416(9) Uani 1 1 d . . .
H3A H -0.0220 1.0984 0.4523 0.050 Uiso 1 1 calc R . .
H3B H -0.0860 0.9675 0.4754 0.050 Uiso 1 1 calc R . .
C4 C -0.1168(10) 1.0666(5) 0.2651(3) 0.0739(16) Uani 1 1 d . . .
H4A H -0.1091 1.0452 0.1955 0.111 Uiso 1 1 calc R . .
H4B H -0.0649 1.1466 0.2767 0.111 Uiso 1 1 calc R . .
H4C H -0.2724 1.0601 0.2785 0.111 Uiso 1 1 calc R . .
C5 C 0.2559(7) 1.0020(3) 0.5164(3) 0.0364(9) Uani 1 1 d . . .
C6 C 0.4757(6) 0.9209(3) 0.6703(3) 0.0354(8) Uani 1 1 d . . .
H6 H 0.572(7) 0.992(4) 0.672(3) 0.042 Uiso 1 1 calc . . .
C7 C 0.6029(6) 0.8192(4) 0.6298(2) 0.0374(8) Uani 1 1 d . . .
C8 C 0.4370(7) 0.8926(3) 0.7794(3) 0.0385(8) Uani 1 1 d . . .
H8A H 0.3250 0.8294 0.7773 0.046 Uiso 1 1 calc R . .
H8B H 0.5798 0.8637 0.8169 0.046 Uiso 1 1 calc R . .
C9 C 0.3540(7) 0.9972(3) 0.8371(3) 0.0396(9) Uani 1 1 d . . .
H9 H 0.217(7) 1.030(4) 0.795(3) 0.048 Uiso 1 1 calc . . .
C10 C 0.2845(7) 0.9578(4) 0.9394(3) 0.0432(9) Uani 1 1 d . . .
C11 C 0.5325(9) 1.0943(4) 0.8523(3) 0.0583(12) Uani 1 1 d . . .
H11A H 0.6734 1.0630 0.8877 0.088 Uiso 1 1 calc R . .
H11B H 0.4791 1.1571 0.8917 0.088 Uiso 1 1 calc R . .
H11C H 0.5583 1.1243 0.7870 0.088 Uiso 1 1 calc R . .
Cl1 Cl -0.3102(2) 0.82103(15) 0.33181(11) 0.0813(4) Uani 1 1 d . . .
Cl2 Cl 0.1599(2) 0.75925(9) 0.39606(8) 0.0573(3) Uani 1 1 d . . .
Cl3 Cl 0.0122(2) 0.81676(12) 0.18701(8) 0.0622(3) Uani 1 1 d . . .
Cl4 Cl 0.1665(3) 1.07687(11) 1.00170(9) 0.0742(4) Uani 1 1 d . . .
Cl5 Cl 0.5210(2) 0.90117(11) 1.02272(8) 0.0621(3) Uani 1 1 d . . .
Cl6 Cl 0.0720(2) 0.84494(12) 0.92171(9) 0.0722(4) Uani 1 1 d . . .
N N 0.2586(5) 0.9450(3) 0.6051(2) 0.0356(7) Uani 1 1 d . . .
H0 H 0.1316 0.9224 0.6239 0.043 Uiso 1 1 calc R . .
O1 O 0.4344(5) 1.0427(2) 0.49160(19) 0.0492(7) Uani 1 1 d . . .
O2 O 0.8062(5) 0.8194(3) 0.6261(2) 0.0587(8) Uani 1 1 d . . .
O3 O 0.4671(5) 0.7290(3) 0.6043(2) 0.0541(8) Uani 1 1 d . . .
H3 H 0.522(16) 0.669(9) 0.581(7) 0.18(4) 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
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 112.4(3) . . ?
C2 C1 Cl2 111.1(3) . . ?
Cl1 C1 Cl2 107.5(2) . . ?
C2 C1 Cl3 110.8(3) . . ?
Cl1 C1 Cl3 108.2(2) . . ?
Cl2 C1 Cl3 106.6(2) . . ?
C1 C2 C4 111.7(4) . . ?
C1 C2 C3 112.3(3) . . ?
C4 C2 C3 110.3(3) . . ?
C1 C2 H2 107(2) . . ?
C4 C2 H2 108(2) . . ?
C3 C2 H2 108(2) . . ?
C5 C3 C2 112.9(3) . . ?
C5 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C5 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N 120.6(3) . . ?
O1 C5 C3 121.5(3) . . ?
N C5 C3 117.9(3) . . ?
N C6 C7 111.6(3) . . ?
N C6 C8 111.2(3) . . ?
C7 C6 C8 108.9(3) . . ?
N C6 H6 108(2) . . ?
C7 C6 H6 108(2) . . ?
C8 C6 H6 108(2) . . ?
O2 C7 O3 124.4(4) . . ?
O2 C7 C6 123.9(4) . . ?
O3 C7 C6 111.6(3) . . ?
C9 C8 C6 114.4(3) . . ?
C9 C8 H8A 108.7 . . ?
C6 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C6 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C11 C9 C8 111.2(3) . . ?
C11 C9 C10 111.2(3) . . ?
C8 C9 C10 111.2(3) . . ?
C11 C9 H9 108(2) . . ?
C8 C9 H9 108(2) . . ?
C10 C9 H9 108(2) . . ?
C9 C10 Cl5 111.7(3) . . ?
C9 C10 Cl4 111.2(3) . . ?
Cl5 C10 Cl4 108.1(2) . . ?
C9 C10 Cl6 111.3(3) . . ?
Cl5 C10 Cl6 107.4(2) . . ?
Cl4 C10 Cl6 106.9(2) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 N C6 120.5(3) . . ?
C5 N H0 119.7 . . ?
C6 N H0 119.7 . . ?
C7 O3 H3 118(7) . . ?
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 1.519(6) . ?
C1 Cl1 1.775(4) . ?
C1 Cl2 1.775(4) . ?
C1 Cl3 1.784(4) . ?
C2 C4 1.534(6) . ?
C2 C3 1.544(5) . ?
C2 H2 0.98(4) . ?
C3 C5 1.513(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 O1 1.234(5) . ?
C5 N 1.336(4) . ?
C6 N 1.462(5) . ?
C6 C7 1.511(5) . ?
C6 C8 1.527(5) . ?
C6 H6 0.98(4) . ?
C7 O2 1.204(4) . ?
C7 O3 1.310(5) . ?
C8 C9 1.526(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.513(6) . ?
C9 C10 1.534(5) . ?
C9 H9 0.98(4) . ?
C10 Cl5 1.768(4) . ?
C10 Cl4 1.771(4) . ?
C10 Cl6 1.779(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N H0 0.8600 . ?
O3 H3 0.83(10) . ?
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 C4 -60.8(4) . . . . ?
Cl2 C1 C2 C4 178.6(3) . . . . ?
Cl3 C1 C2 C4 60.3(4) . . . . ?
Cl1 C1 C2 C3 63.6(4) . . . . ?
Cl2 C1 C2 C3 -56.9(4) . . . . ?
Cl3 C1 C2 C3 -175.3(3) . . . . ?
C1 C2 C3 C5 91.6(4) . . . . ?
C4 C2 C3 C5 -143.2(4) . . . . ?
C2 C3 C5 O1 48.8(5) . . . . ?
C2 C3 C5 N -132.4(4) . . . . ?
N C6 C7 O2 136.5(4) . . . . ?
C8 C6 C7 O2 -100.4(4) . . . . ?
N C6 C7 O3 -46.7(4) . . . . ?
C8 C6 C7 O3 76.4(4) . . . . ?
N C6 C8 C9 -68.3(4) . . . . ?
C7 C6 C8 C9 168.3(3) . . . . ?
C6 C8 C9 C11 -64.1(4) . . . . ?
C6 C8 C9 C10 171.4(3) . . . . ?
C11 C9 C10 Cl5 -60.7(4) . . . . ?
C8 C9 C10 Cl5 63.8(4) . . . . ?
C11 C9 C10 Cl4 60.2(4) . . . . ?
C8 C9 C10 Cl4 -175.3(3) . . . . ?
C11 C9 C10 Cl6 179.3(3) . . . . ?
C8 C9 C10 Cl6 -56.2(4) . . . . ?
O1 C5 N C6 -5.3(5) . . . . ?
C3 C5 N C6 175.9(3) . . . . ?
C7 C6 N C5 -76.5(4) . . . . ?
C8 C6 N C5 161.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660085
