#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:49:31 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178918 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/47/4114725.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_4114725
loop_
_publ_author_name
'Christopher P. McArdle'
'Steve Van'
'Michael C. Jennings'
'Richard J. Puddephatt'
_publ_section_title
;
 Gold(I) Macrocycles and Topologically Chiral [2]Catenanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3959
_journal_page_last               3965
_journal_paper_doi               10.1021/ja012006+
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C28 H24 Br O2'
_chemical_formula_weight         472.38
_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                 102.925(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8604(4)
_cell_length_b                   18.4059(8)
_cell_length_c                   9.3622(3)
_cell_measurement_temperature    200(2)
_cell_volume                     2327.91(14)
_computing_cell_refinement       'Nonius DENZO'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'phi/omega scans'
_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  0.071
_diffrn_reflns_av_sigmaI/netI    0.0913
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24120
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    1.787
_exptl_absorpt_correction_T_max  0.8075
_exptl_absorpt_correction_T_min  0.7219
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.158
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2678
_reflns_number_total             5310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0120062B_1.cif
_cod_data_source_block           compound1
_cod_database_code               4114725
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
Br1 Br 0.09383(2) 0.250399(17) 0.25585(3) 0.05990(13) Uani 1 1 d .
C2 C -0.01148(19) 0.29848(15) 0.1243(3) 0.0423(7) Uani 1 1 d .
C3 C 0.00961(19) 0.35819(15) 0.0499(3) 0.0442(7) Uani 1 1 d .
H3A H 0.0759 0.3744 0.0609 0.053 Uiso 1 1 calc R
C4 C -0.06734(18) 0.39447(15) -0.0416(3) 0.0438(7) Uani 1 1 d .
H4A H -0.0531 0.4365 -0.0920 0.053 Uiso 1 1 calc R
C5 C -0.16497(18) 0.37135(14) -0.0621(3) 0.0341(6) Uani 1 1 d .
C6 C -0.18249(19) 0.31119(15) 0.0151(3) 0.0497(8) Uani 1 1 d .
H6A H -0.2486 0.2944 0.0042 0.060 Uiso 1 1 calc R
C7 C -0.1066(2) 0.27415(15) 0.1085(3) 0.0529(8) Uani 1 1 d .
H7A H -0.1205 0.2326 0.1606 0.063 Uiso 1 1 calc R
C8 C -0.24466(17) 0.41524(14) -0.1641(3) 0.0359(6) Uani 1 1 d .
H8A H -0.2260 0.4163 -0.2613 0.043 Uiso 1 1 calc R
C9 C -0.24805(17) 0.49386(13) -0.1157(3) 0.0330(6) Uani 1 1 d .
C10 C -0.23076(17) 0.51344(14) 0.0308(3) 0.0366(6) Uani 1 1 d .
H10A H -0.2088 0.4777 0.1041 0.044 Uiso 1 1 calc R
C11 C -0.24509(17) 0.58462(14) 0.0723(3) 0.0386(7) Uani 1 1 d .
H11A H -0.2340 0.5969 0.1732 0.046 Uiso 1 1 calc R
C12 C -0.27530(17) 0.63720(14) -0.0328(3) 0.0348(6) Uani 1 1 d .
C13 C -0.28920(18) 0.61899(15) -0.1798(3) 0.0415(7) Uani 1 1 d .
H13A H -0.3079 0.6553 -0.2530 0.050 Uiso 1 1 calc R
C14 C -0.27583(17) 0.54798(15) -0.2198(3) 0.0402(7) Uani 1 1 d .
H14A H -0.2859 0.5360 -0.3207 0.048 Uiso 1 1 calc R
O15 O -0.29099(12) 0.70637(9) 0.01391(18) 0.0410(4) Uani 1 1 d .
H15A H -0.3072 0.7340 -0.0590 0.062 Uiso 1 1 calc R
C16 C -0.34835(17) 0.38219(13) -0.1909(3) 0.0350(6) Uani 1 1 d .
C17 C -0.39035(19) 0.35001(14) -0.3226(3) 0.0434(7) Uani 1 1 d .
H17A H -0.3540 0.3478 -0.3973 0.052 Uiso 1 1 calc R
C18 C -0.4853(2) 0.32061(15) -0.3482(3) 0.0486(8) Uani 1 1 d .
H18A H -0.5135 0.2990 -0.4402 0.058 Uiso 1 1 calc R
C19 C -0.53777(19) 0.32288(14) -0.2405(3) 0.0404(7) Uani 1 1 d .
C20 C -0.49812(19) 0.35588(14) -0.1091(3) 0.0433(7) Uani 1 1 d .
H20A H -0.5348 0.3582 -0.0347 0.052 Uiso 1 1 calc R
C21 C -0.40390(19) 0.38587(15) -0.0857(3) 0.0430(7) Uani 1 1 d .
H21A H -0.3771 0.4094 0.0048 0.052 Uiso 1 1 calc R
O22 O -0.63190(13) 0.29298(11) -0.27040(19) 0.0504(5) Uani 1 1 d .
H22A H -0.6518 0.2894 -0.1923 0.076 Uiso 1 1 calc R
C31 C 0.5604(3) 0.0482(3) 0.8159(4) 0.0774(11) Uani 1 1 d .
H31A H 0.4976 0.0251 0.7986 0.093 Uiso 1 1 calc R
C32 C 0.5664(3) 0.1209(2) 0.7877(3) 0.0689(10) Uani 1 1 d .
H32A H 0.5077 0.1484 0.7535 0.083 Uiso 1 1 calc R
C33 C 0.6561(3) 0.15346(19) 0.8085(3) 0.0655(9) Uani 1 1 d .
H33A H 0.6600 0.2036 0.7862 0.079 Uiso 1 1 calc R
C34 C 0.7413(2) 0.1153(2) 0.8612(3) 0.0608(9) Uani 1 1 d .
H34A H 0.8038 0.1388 0.8765 0.073 Uiso 1 1 calc R
C35 C 0.7356(2) 0.0426(2) 0.8917(3) 0.0628(9) Uani 1 1 d .
H35A H 0.7944 0.0157 0.9285 0.075 Uiso 1 1 calc R
C36 C 0.6446(3) 0.00851(18) 0.8690(3) 0.0698(10) Uani 1 1 d .
H36A H 0.6404 -0.0418 0.8898 0.084 Uiso 1 1 calc R
C42 C 1.0184(2) 0.07091(18) 0.9705(4) 0.0632(9) Uani 1 1 d .
H42A H 1.0310 0.1201 0.9498 0.076 Uiso 1 1 calc R
C41 C 1.0069(2) 0.0198(2) 0.8618(4) 0.0703(10) Uani 1 1 d .
H41A H 1.0119 0.0336 0.7659 0.105 Uiso 1 1 calc R
C43 C 1.0118(2) 0.05118(19) 1.1088(4) 0.0661(9) Uani 1 1 d .
H43A H 1.0202 0.0866 1.1845 0.099 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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'
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_3
C3 C2 C7 121.2(2) .
C3 C2 Br1 118.9(2) .
C7 C2 Br1 119.9(2) .
C2 C3 C4 118.7(2) .
C3 C4 C5 122.0(3) .
C6 C5 C4 117.1(2) .
C6 C5 C8 124.7(2) .
C4 C5 C8 118.2(2) .
C5 C6 C7 122.0(3) .
C2 C7 C6 118.9(3) .
C5 C8 C9 112.6(2) .
C5 C8 C16 114.6(2) .
C9 C8 C16 109.7(2) .
C10 C9 C14 117.9(2) .
C10 C9 C8 122.2(2) .
C14 C9 C8 119.8(2) .
C9 C10 C11 121.1(2) .
C12 C11 C10 120.1(2) .
C11 C12 O15 117.8(2) .
C11 C12 C13 119.4(2) .
O15 C12 C13 122.7(2) .
C14 C13 C12 119.9(2) .
C13 C14 C9 121.5(2) .
C17 C16 C21 118.0(2) .
C17 C16 C8 120.9(2) .
C21 C16 C8 121.1(2) .
C16 C17 C18 121.1(3) .
C19 C18 C17 119.9(2) .
C18 C19 C20 120.1(2) .
C18 C19 O22 118.1(2) .
C20 C19 O22 121.8(3) .
C19 C20 C21 119.4(3) .
C16 C21 C20 121.5(2) .
C32 C31 C36 120.5(3) .
C33 C32 C31 119.8(3) .
C32 C33 C34 121.0(3) .
C33 C34 C35 119.4(3) .
C34 C35 C36 120.2(3) .
C31 C36 C35 119.1(3) .
C41 C42 C43 120.0(3) .
C42 C41 C43 120.1(3) 3_757
C42 C43 C41 119.9(3) 3_757
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.904(2) .
C2 C3 1.367(4) .
C2 C7 1.369(4) .
C3 C4 1.382(3) .
C4 C5 1.390(3) .
C5 C6 1.373(3) .
C5 C8 1.521(3) .
C6 C7 1.387(4) .
C8 C9 1.520(3) .
C8 C16 1.529(3) .
C9 C10 1.386(3) .
C9 C14 1.386(3) .
C10 C11 1.393(3) .
C11 C12 1.377(3) .
C12 O15 1.379(3) .
C12 C13 1.388(3) .
C13 C14 1.383(3) .
C16 C17 1.374(3) .
C16 C21 1.381(3) .
C17 C18 1.393(4) .
C18 C19 1.370(4) .
C19 C20 1.372(3) .
C19 O22 1.386(3) .
C20 C21 1.389(3) .
C31 C32 1.370(5) .
C31 C36 1.373(5) .
C32 C33 1.355(5) .
C33 C34 1.367(4) .
C34 C35 1.374(4) .
C35 C36 1.381(4) .
C42 C41 1.368(4) .
C42 C43 1.368(4) .
C41 C43 1.372(4) 3_757
C43 C41 1.372(4) 3_757
