#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:54:59 +0100 (mar 22 de mar de 2016) $
#$Revision: 178923 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/52/4115278.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_4115278
loop_
_publ_author_name
'Peter R. Schreiner'
'Andrey A. Fokin'
'Oliver Lauenstein'
'Yoshio Okamoto'
'Tsuneki Wakita'
'Christopher Rinderspacher'
'Gregory H. Robinson'
'Jason K. Vohs'
'Charles F. Campana'
_publ_section_title
;
 Pseudotetrahedral Polyhaloadamantanes as Chirality Probes: Synthesis,
 Separation, and Absolute Configuration
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13348
_journal_page_last               13349
_journal_paper_doi               10.1021/ja0274195
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C10 H12 Br Cl F I'
_chemical_formula_sum            'C10 H12 Br Cl F I'
_chemical_formula_weight         393.46
_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_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                 90.0120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4234(6)
_cell_length_b                   12.3944(6)
_cell_length_c                   7.8787(3)
_cell_measurement_temperature    301(2)
_cell_volume                     1213.17(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL 6.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8135
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    6.127
_exptl_absorpt_correction_T_max  0.378
_exptl_absorpt_correction_T_min  0.153
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.154
_exptl_crystal_description       cubic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.967
_refine_diff_density_min         -1.473
_refine_diff_density_rms         0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.321
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0879
_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)+(0.0924P)²+22.7206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2226
_reflns_number_gt                2399
_reflns_number_total             2761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0274195-2_s1.cif
_cod_data_source_block           ps6x
_cod_database_code               4115278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
_atom_site_refinement_flags
I1 I 0.55375(8) 0.18094(9) 0.05412(14) 0.0689(4) Uani 1 1 d .
Br2 Br 0.96661(10) 0.19454(12) 0.40003(19) 0.0557(4) Uani 1 1 d .
Cl3 Cl 0.6568(2) -0.1158(2) 0.5834(3) 0.0404(6) Uani 1 1 d .
F4 F 0.8564(7) -0.1297(8) 0.0074(12) 0.078(3) Uani 1 1 d .
C1 C 0.6767(8) 0.0854(10) 0.1671(14) 0.042(2) Uani 1 1 d .
C2 C 0.8501(8) 0.0943(9) 0.3171(14) 0.038(2) Uani 1 1 d .
C3 C 0.7158(9) -0.0438(9) 0.3982(14) 0.041(2) Uani 1 1 d .
C4 C 0.8104(10) -0.0576(10) 0.1268(18) 0.053(3) Uani 1 1 d .
C5 C 0.7247(10) 0.0058(11) 0.0376(15) 0.051(3) Uani 1 1 d .
H5A H 0.6691 -0.0421 -0.0048 0.061 Uiso 1 1 calc R
H5B H 0.7553 0.0448 -0.0577 0.061 Uiso 1 1 calc R
C6 C 0.7615(10) -0.1223(9) 0.2712(18) 0.051(3) Uani 1 1 d .
H6A H 0.7050 -0.1690 0.2284 0.062 Uiso 1 1 calc R
H6B H 0.8161 -0.1669 0.3244 0.062 Uiso 1 1 calc R
C7 C 0.8994(9) 0.0166(11) 0.1889(16) 0.049(3) Uani 1 1 d .
H7A H 0.9299 0.0563 0.0944 0.059 Uiso 1 1 calc R
H7B H 0.9562 -0.0253 0.2419 0.059 Uiso 1 1 calc R
C8 C 0.8002(9) 0.0285(10) 0.4692(14) 0.044(2) Uani 1 1 d .
H8A H 0.8556 -0.0137 0.5250 0.053 Uiso 1 1 calc R
H8B H 0.7690 0.0773 0.5518 0.053 Uiso 1 1 calc R
C9 C 0.7632(8) 0.1627(9) 0.2275(14) 0.041(2) Uani 1 1 d .
H9A H 0.7330 0.2150 0.3057 0.049 Uiso 1 1 calc R
H9B H 0.7942 0.2011 0.1319 0.049 Uiso 1 1 calc R
C10 C 0.6264(8) 0.0236(9) 0.3125(14) 0.040(2) Uani 1 1 d .
H10A H 0.5700 -0.0234 0.2704 0.048 Uiso 1 1 calc R
H10B H 0.5951 0.0733 0.3937 0.048 Uiso 1 1 calc R
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
I1 0.0530(6) 0.0789(7) 0.0749(7) 0.0293(5) -0.0141(4) -0.0071(4)
Br2 0.0422(6) 0.0605(8) 0.0644(8) -0.0129(6) -0.0083(5) -0.0033(5)
Cl3 0.0442(13) 0.0363(12) 0.0406(13) 0.0178(10) 0.0053(10) -0.0043(10)
F4 0.067(5) 0.082(6) 0.084(6) -0.046(5) 0.002(5) 0.018(5)
C1 0.033(5) 0.051(6) 0.042(6) 0.000(5) -0.004(4) 0.003(4)
C2 0.030(5) 0.043(6) 0.043(5) -0.004(4) 0.001(4) 0.000(4)
C3 0.041(5) 0.038(5) 0.044(6) 0.007(5) 0.004(4) 0.003(4)
C4 0.050(6) 0.046(7) 0.063(7) -0.026(6) 0.009(6) 0.005(5)
C5 0.048(6) 0.062(8) 0.042(6) -0.006(6) 0.001(5) 0.003(6)
C6 0.053(7) 0.026(5) 0.075(8) -0.007(5) 0.000(6) 0.008(5)
C7 0.032(5) 0.060(7) 0.055(7) -0.018(6) 0.003(5) 0.009(5)
C8 0.045(6) 0.048(6) 0.040(6) -0.004(5) -0.001(5) 0.002(5)
C9 0.035(5) 0.042(6) 0.046(6) 0.000(5) 0.003(4) 0.005(4)
C10 0.031(5) 0.040(6) 0.049(6) 0.002(5) -0.004(4) 0.002(4)
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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C10 C1 C9 111.3(9)
C10 C1 C5 110.0(10)
C9 C1 C5 109.8(9)
C10 C1 I1 107.8(7)
C9 C1 I1 106.6(7)
C5 C1 I1 111.2(7)
C7 C2 C9 110.0(9)
C7 C2 C8 109.3(9)
C9 C2 C8 110.7(8)
C7 C2 Br2 108.5(7)
C9 C2 Br2 107.9(7)
C8 C2 Br2 110.4(7)
C8 C3 C6 111.5(10)
C8 C3 C10 109.8(9)
C6 C3 C10 109.7(9)
C8 C3 Cl3 105.7(8)
C6 C3 Cl3 111.1(8)
C10 C3 Cl3 108.9(7)
F4 C4 C5 107.4(10)
F4 C4 C7 107.7(9)
C5 C4 C7 110.4(11)
F4 C4 C6 109.5(10)
C5 C4 C6 110.2(10)
C7 C4 C6 111.5(11)
C4 C5 C1 107.8(9)
C3 C6 C4 107.8(9)
C4 C7 C2 107.7(9)
C3 C8 C2 107.7(9)
C1 C9 C2 106.8(9)
C1 C10 C3 108.4(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.125(10)
Br2 C2 2.024(10)
Cl3 C3 1.856(11)
F4 C4 1.416(13)
C1 C10 1.512(15)
C1 C9 1.529(14)
C1 C5 1.527(16)
C2 C7 1.520(14)
C2 C9 1.535(14)
C2 C8 1.579(15)
C3 C8 1.494(15)
C3 C6 1.502(16)
C3 C10 1.542(14)
C4 C5 1.505(18)
C4 C7 1.514(16)
C4 C6 1.526(19)
