#------------------------------------------------------------------------------
#$Date: 2016-02-16 21:30:59 +0100 (mar 16 de feb de 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/52/4105247.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_4105247
loop_
_publ_author_name
'Christian Nilewski'
'Roger W. Geisser'
'Marc-Olivier Ebert'
'Erick M. Carreira'
_publ_contact_author_address
;ETH Zurich
Laboratory of Organic Chemistry
HCI H330
Wolfgang-Pauli-Strasse 10
8093 Zurich
;
_publ_contact_author_email       Christian
_publ_contact_author_fax         '+41 44 632 13 28'
_publ_contact_author_name        Nilewski
_publ_contact_author_phone       '+41 44 632 29 43'
_publ_section_title
;
 Conformational and Configurational Analysis in the Study and Synthesis of
 Chlorinated Natural Products
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15866
_journal_page_last               15876
_journal_paper_doi               10.1021/ja906461h
_journal_volume                  131
_journal_year                    2009
_chemical_compound_source        'Carreira laboratory'
_chemical_formula_moiety         'C6 H11 Cl3 O2 '
_chemical_formula_sum            'C6 H11 Cl3 O2'
_chemical_formula_weight         221.511
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 104.045(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.400(2)
_cell_length_b                   5.6769(8)
_cell_length_c                   10.0838(13)
_cell_measurement_reflns_used    4829
_cell_measurement_temperature    22
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.425
_cell_volume                     910.7(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Altomare et al., J. Appl. Cryst.,1999)'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.09813
_diffrn_orient_matrix_UB_12      -0.00363
_diffrn_orient_matrix_UB_13      0.02840
_diffrn_orient_matrix_UB_21      0.03588
_diffrn_orient_matrix_UB_22      -0.13554
_diffrn_orient_matrix_UB_23      0.10664
_diffrn_orient_matrix_UB_31      -0.00292
_diffrn_orient_matrix_UB_32      0.03835
_diffrn_orient_matrix_UB_33      0.04972
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2727
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       Cube
_exptl_crystal_F_000             456.0
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .08
_exptl_crystal_size_min          .02
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+ (0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                1068
_reflns_number_total             1602
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja906461h_si_003.cif
_cod_data_source_block           publication_text
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C6 H11 Cl3 O2 '
_cod_database_code               4105247
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+Y+ 1/2,-Z+ 1/2'
'+X,-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_symmetry_multiplicity
_atom_site_calc_flag
Cl9 Cl 0.22417(8) 0.7718(2) -0.15797(13) 0.0313(4) Uani 1 1 d
Cl10 Cl 0.26050(8) 0.2071(2) 0.13934(14) 0.0312(4) Uani 1 1 d
Cl11 Cl 0.43138(8) 0.2156(3) 0.02519(16) 0.0439(5) Uani 1 1 d
O7 O 0.0028(3) 0.3073(9) -0.1610(5) 0.0385(12) Uani 1 1 d
O8 O 0.0708(2) 0.7375(7) -0.0571(4) 0.0315(9) Uani 1 1 d
C1 C 0.0892(3) 0.3557(11) -0.1522(7) 0.0308(14) Uani 1 1 d
C2 C 0.1194(3) 0.5268(10) -0.0354(6) 0.0263(12) Uani 1 1 d
C3 C 0.2124(3) 0.5939(9) -0.0143(5) 0.0226(11) Uani 1 1 d
C4 C 0.2753(3) 0.3915(10) 0.0014(5) 0.0253(12) Uani 1 1 d
C5 C 0.3676(3) 0.4738(10) 0.0305(6) 0.0294(12) Uani 1 1 d
C6 C 0.4010(4) 0.6045(13) 0.1604(7) 0.0375(15) Uani 1 1 d
H1A H 0.099(3) 0.405(10) -0.237(6) 0.033(16) Uiso 1 1 d
H1B H 0.112(4) 0.220(12) -0.127(7) 0.05(2) Uiso 1 1 d
H2 H 0.115(2) 0.455(8) 0.038(5) 0.004(11) Uiso 1 1 d
H3 H 0.227(3) 0.698(9) 0.061(5) 0.019(13) Uiso 1 1 d
H4 H 0.265(4) 0.297(11) -0.082(6) 0.051(19) Uiso 1 1 d
H5 H 0.375(3) 0.558(9) -0.043(5) 0.015(12) Uiso 1 1 d
H6A H 0.457(4) 0.651(13) 0.159(7) 0.07(2) Uiso 1 1 d
H6B H 0.373(4) 0.745(13) 0.172(7) 0.07(2) Uiso 1 1 d
H6C H 0.404(3) 0.532(12) 0.242(7) 0.047(19) Uiso 1 1 d
H7 H -0.016(4) 0.290(11) -0.220(6) 0.017(19) Uiso 1 1 d
H8 H 0.050(4) 0.730(11) 0.001(6) 0.04(2) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl9 0.0357(7) 0.0287(8) 0.0311(8) 0.0079(6) 0.0113(6) 0.0028(5)
Cl10 0.0352(8) 0.0286(8) 0.0306(8) 0.0070(6) 0.0094(6) 0.0031(5)
Cl11 0.0315(8) 0.0476(10) 0.0530(10) 0.0004(8) 0.0110(7) 0.0131(6)
O7 0.025(2) 0.054(3) 0.034(3) -0.006(2) 0.003(2) -0.0043(19)
O8 0.028(2) 0.031(2) 0.037(2) 0.0024(19) 0.0105(18) 0.0102(15)
C1 0.022(3) 0.030(3) 0.040(4) -0.006(3) 0.007(2) -0.001(2)
C2 0.029(3) 0.028(3) 0.022(3) 0.004(3) 0.006(2) 0.003(2)
C3 0.031(3) 0.020(3) 0.020(3) -0.002(2) 0.010(2) 0.000(2)
C4 0.028(3) 0.026(3) 0.022(3) 0.004(2) 0.005(2) 0.003(2)
C5 0.023(3) 0.031(3) 0.034(3) 0.006(3) 0.008(2) 0.002(2)
C6 0.030(3) 0.042(4) 0.039(4) -0.007(3) 0.005(3) -0.003(3)
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_diffrn_radiation_wavelength
0.71073
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O7 C1 C2 107.7(4)
O8 C2 C1 110.7(4)
O8 C2 C3 108.2(4)
C1 C2 C3 113.1(4)
C4 C3 C2 116.8(4)
C4 C3 Cl9 107.6(3)
C2 C3 Cl9 108.8(3)
C3 C4 C5 113.5(5)
C3 C4 Cl10 107.7(4)
C5 C4 Cl10 109.8(3)
C6 C5 C4 116.9(5)
C6 C5 Cl11 109.8(4)
C4 C5 Cl11 107.3(4)
C1 O7 H7 111(6)
C2 O8 H8 100(5)
O7 C1 H1A 113(3)
C2 C1 H1A 115(3)
O7 C1 H1B 102(4)
C2 C1 H1B 108(4)
H1A C1 H1B 112(5)
O8 C2 H2 111(3)
C1 C2 H2 107(3)
C3 C2 H2 107(3)
C4 C3 H3 111(3)
C2 C3 H3 109(3)
Cl9 C3 H3 104(3)
C3 C4 H4 110(3)
C5 C4 H4 107(4)
Cl10 C4 H4 108(4)
C6 C5 H5 111(3)
C4 C5 H5 109(3)
Cl11 C5 H5 102(3)
C5 C6 H6A 106(4)
C5 C6 H6B 116(4)
H6A C6 H6B 105(6)
C5 C6 H6C 120(4)
H6A C6 H6C 108(5)
H6B C6 H6C 101(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl9 C3 1.814(5)
Cl10 C4 1.804(5)
Cl11 C5 1.809(5)
O7 C1 1.424(7)
O8 C2 1.424(6)
C1 C2 1.514(8)
C2 C3 1.537(7)
C3 C4 1.526(7)
C4 C5 1.543(7)
C5 C6 1.489(8)
O7 H7 0.61(5)
O8 H8 0.75(6)
C1 H1A 0.95(6)
C1 H1B 0.87(6)
C2 H2 0.87(5)
C3 H3 0.95(5)
C4 H4 0.98(6)
C5 H5 0.92(5)
C6 H6A 0.95(7)
C6 H6B 0.94(7)
C6 H6C 0.92(7)
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
O7 C1 C2 O8 -58.4(6)
O7 C1 C2 C3 179.9(5)
O8 C2 C3 C4 -176.1(4)
C1 C2 C3 C4 -53.0(6)
O8 C2 C3 Cl9 -54.1(5)
C1 C2 C3 Cl9 69.0(5)
C2 C3 C4 C5 -176.6(4)
Cl9 C3 C4 C5 60.8(5)
C2 C3 C4 Cl10 -54.9(5)
Cl9 C3 C4 Cl10 -177.5(2)
C3 C4 C5 C6 63.1(7)
Cl10 C4 C5 C6 -57.4(6)
C3 C4 C5 Cl11 -173.2(4)
Cl10 C4 C5 Cl11 66.3(4)
