#------------------------------------------------------------------------------
#$Date: 2016-03-21 16:59:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178763 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/17/4101766.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_4101766
loop_
_publ_author_name
'Berryman, Orion B'
'Bryantsev, Vyacheslav S'
'Stay, David P'
'Johnson, Darren W'
'Hay, Benjamin P'
_publ_section_title
;
 Structural criteria for the design of anion receptors: the interaction of
 halides with electron-deficient arenes.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              48
_journal_page_last               58
_journal_paper_doi               10.1021/ja063460m
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C32 H28 Br K N8 O6'
_chemical_formula_weight         739.63
_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                 102.415(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.976(4)
_cell_length_b                   7.5295(19)
_cell_length_c                   27.347(7)
_cell_measurement_reflns_used    2096
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      2.81
_cell_volume                     3413.8(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0754
_diffrn_reflns_av_sigmaI/netI    0.1082
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20311
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.108
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+3.5696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                4427
_reflns_number_total             7805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja063460msi20060517_073913.cif
_cod_data_source_block           ob083
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4101766
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.19033(3) 0.91194(6) 0.01752(2) 0.04193(16) Uani 1 1 d . . .
K1 K 0.75201(6) 0.52536(12) 0.75917(3) 0.0262(2) Uani 1 1 d . . .
O1 O 0.74181(17) 0.2841(4) 0.67754(11) 0.0275(7) Uani 1 1 d . . .
O2 O 0.87026(17) 0.5330(4) 0.70337(11) 0.0291(7) Uani 1 1 d . . .
O3 O 0.85291(17) 0.8248(4) 0.76516(10) 0.0280(7) Uani 1 1 d . . .
O4 O 0.75880(18) 0.7674(4) 0.83647(11) 0.0313(7) Uani 1 1 d . . .
O5 O 0.62469(18) 0.5347(4) 0.81032(11) 0.0342(8) Uani 1 1 d . . .
O6 O 0.64052(17) 0.2446(4) 0.74668(11) 0.0315(7) Uani 1 1 d . . .
N1 N 0.6540(2) 0.6760(5) 0.67266(15) 0.0384(10) Uani 1 1 d . . .
N2 N 0.6429(2) 0.0802(5) 0.47662(14) 0.0339(9) Uani 1 1 d . . .
N3 N 0.5457(2) 0.4628(5) 0.38251(15) 0.0362(10) Uani 1 1 d . . .
N4 N 0.5560(2) 1.0300(5) 0.57822(14) 0.0339(9) Uani 1 1 d . . .
N5 N 0.8316(2) 0.3486(5) 0.84830(15) 0.0354(10) Uani 1 1 d . . .
N6 N 0.7774(2) 0.6587(5) 1.07528(14) 0.0333(9) Uani 1 1 d . . .
N7 N 0.9957(2) 0.9222(5) 1.09203(14) 0.0351(9) Uani 1 1 d . . .
N8 N 1.0376(2) 0.5641(5) 0.86718(15) 0.0376(10) Uani 1 1 d . . .
C1 C 0.6284(2) 0.5956(6) 0.57873(15) 0.0230(9) Uani 1 1 d . . .
C2 C 0.6459(2) 0.4306(6) 0.56158(17) 0.0259(10) Uani 1 1 d . . .
C3 C 0.6277(2) 0.3953(5) 0.51065(15) 0.0221(9) Uani 1 1 d . . .
C4 C 0.5924(2) 0.5268(5) 0.47694(15) 0.0219(9) Uani 1 1 d . . .
C5 C 0.5755(2) 0.6933(6) 0.49410(16) 0.0211(9) Uani 1 1 d . . .
C6 C 0.5932(2) 0.7273(5) 0.54495(16) 0.0219(9) Uani 1 1 d . . .
C7 C 0.6444(3) 0.6367(5) 0.63148(18) 0.0277(10) Uani 1 1 d . . .
C8 C 0.6401(2) 0.2199(6) 0.49202(16) 0.0255(10) Uani 1 1 d . . .
C9 C 0.5684(2) 0.4898(5) 0.42429(18) 0.0261(10) Uani 1 1 d . . .
C10 C 0.5736(2) 0.8972(6) 0.56352(15) 0.0255(10) Uani 1 1 d . . .
C11 C 0.8807(2) 0.5273(5) 0.92946(15) 0.0221(9) Uani 1 1 d . . .
C12 C 0.8359(3) 0.5408(6) 0.96612(16) 0.0229(9) Uani 1 1 d . . .
C13 C 0.8635(2) 0.6443(5) 1.00786(15) 0.0213(9) Uani 1 1 d . . .
C14 C 0.9375(2) 0.7359(5) 1.01361(15) 0.0221(9) Uani 1 1 d . . .
C15 C 0.9841(3) 0.7194(5) 0.97738(16) 0.0229(9) Uani 1 1 d . . .
C16 C 0.9552(2) 0.6158(5) 0.93550(15) 0.0221(9) Uani 1 1 d . . .
C17 C 0.8524(2) 0.4233(6) 0.88497(17) 0.0252(9) Uani 1 1 d . . .
C18 C 0.8160(2) 0.6562(6) 1.04570(17) 0.0259(10) Uani 1 1 d . . .
C19 C 0.9683(2) 0.8416(6) 1.05733(16) 0.0235(9) Uani 1 1 d . . .
C20 C 1.0025(3) 0.5906(6) 0.89776(17) 0.0285(10) Uani 1 1 d . . .
C21 C 0.6857(3) 0.7908(7) 0.8538(2) 0.0394(13) Uani 1 1 d . . .
C22 C 0.6481(3) 0.6151(7) 0.85866(19) 0.0384(12) Uani 1 1 d . . .
C23 C 0.5895(3) 0.3647(7) 0.8140(2) 0.0415(13) Uani 1 1 d . . .
C24 C 0.5680(3) 0.2831(7) 0.7629(2) 0.0418(13) Uani 1 1 d . . .
C25 C 0.6257(3) 0.1578(7) 0.6993(2) 0.0355(12) Uani 1 1 d . . .
C26 C 0.7046(3) 0.1199(6) 0.6857(2) 0.0320(11) Uani 1 1 d . . .
C27 C 0.8194(3) 0.2575(6) 0.6666(2) 0.0346(12) Uani 1 1 d . . .
C28 C 0.8549(3) 0.4330(6) 0.65788(18) 0.0324(11) Uani 1 1 d . . .
C29 C 0.9014(3) 0.7048(6) 0.69657(19) 0.0337(11) Uani 1 1 d . . .
C30 C 0.9236(3) 0.7945(7) 0.74638(19) 0.0323(11) Uani 1 1 d . . .
C31 C 0.8715(3) 0.9077(7) 0.81313(17) 0.0314(11) Uani 1 1 d . . .
C32 C 0.7953(3) 0.9367(6) 0.8310(2) 0.0353(12) Uani 1 1 d . . .
H2 H 0.666(2) 0.341(5) 0.5832(15) 0.023(11) Uiso 1 1 d . . .
H5 H 0.553(2) 0.778(5) 0.4717(15) 0.022(11) Uiso 1 1 d . . .
H12 H 0.783(3) 0.485(6) 0.9613(16) 0.039(13) Uiso 1 1 d . . .
H15 H 1.038(3) 0.782(7) 0.9837(19) 0.065(17) Uiso 1 1 d . . .
H21A H 0.646(3) 0.871(5) 0.8263(16) 0.034(12) Uiso 1 1 d . . .
H21B H 0.694(3) 0.855(6) 0.8840(19) 0.050(15) Uiso 1 1 d . . .
H22A H 0.595(3) 0.633(5) 0.8727(16) 0.039(13) Uiso 1 1 d . . .
H22B H 0.685(3) 0.540(6) 0.8823(17) 0.036(13) Uiso 1 1 d . . .
H23A H 0.536(3) 0.383(6) 0.8298(18) 0.054(15) Uiso 1 1 d . . .
H23B H 0.630(3) 0.289(6) 0.8344(16) 0.037(14) Uiso 1 1 d . . .
H24A H 0.533(3) 0.363(7) 0.7372(19) 0.057(17) Uiso 1 1 d . . .
H24B H 0.529(3) 0.167(8) 0.764(2) 0.083(19) Uiso 1 1 d . . .
H25A H 0.594(2) 0.233(5) 0.6719(16) 0.028(12) Uiso 1 1 d . . .
H25B H 0.597(2) 0.043(6) 0.7023(15) 0.034(13) Uiso 1 1 d . . .
H26A H 0.695(2) 0.050(5) 0.6526(17) 0.034(12) Uiso 1 1 d . . .
H26B H 0.737(3) 0.052(6) 0.7099(17) 0.033(13) Uiso 1 1 d . . .
H27A H 0.811(3) 0.179(6) 0.6348(17) 0.041(13) Uiso 1 1 d . . .
H27B H 0.852(2) 0.201(5) 0.6937(16) 0.026(12) Uiso 1 1 d . . .
H28A H 0.817(2) 0.500(5) 0.6324(16) 0.025(12) Uiso 1 1 d . . .
H28B H 0.904(2) 0.421(5) 0.6466(15) 0.026(11) Uiso 1 1 d . . .
H29A H 0.856(3) 0.778(5) 0.6737(16) 0.031(12) Uiso 1 1 d . . .
H29B H 0.949(2) 0.695(5) 0.6821(15) 0.025(11) Uiso 1 1 d . . .
H30A H 0.954(3) 0.905(6) 0.7437(17) 0.046(14) Uiso 1 1 d . . .
H30B H 0.961(3) 0.727(6) 0.7690(16) 0.029(13) Uiso 1 1 d . . .
H31A H 0.894(2) 1.024(6) 0.8121(16) 0.033(13) Uiso 1 1 d . . .
H31B H 0.907(3) 0.830(6) 0.8369(18) 0.048(15) Uiso 1 1 d . . .
H32A H 0.747(3) 1.020(6) 0.8030(18) 0.054(15) Uiso 1 1 d . . .
H32B H 0.802(2) 0.993(5) 0.8608(16) 0.024(12) 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'
K K 0.2009 0.2494 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 K1 O4 119.31(9) . . ?
O2 K1 O6 119.85(9) . . ?
O4 K1 O6 120.23(9) . . ?
O2 K1 O3 60.76(9) . . ?
O4 K1 O3 60.30(9) . . ?
O6 K1 O3 174.62(9) . . ?
O2 K1 O5 175.61(9) . . ?
O4 K1 O5 61.04(9) . . ?
O6 K1 O5 60.68(9) . . ?
O3 K1 O5 118.25(9) . . ?
O2 K1 N1 84.06(11) . . ?
O4 K1 N1 107.16(11) . . ?
O6 K1 N1 86.57(11) . . ?
O3 K1 N1 88.20(10) . . ?
O5 K1 N1 91.66(11) . . ?
O2 K1 N5 102.38(11) . . ?
O4 K1 N5 73.78(10) . . ?
O6 K1 N5 86.31(10) . . ?
O3 K1 N5 98.84(10) . . ?
O5 K1 N5 81.97(10) . . ?
N1 K1 N5 172.15(12) . . ?
O2 K1 O1 60.78(8) . . ?
O4 K1 O1 178.16(9) . . ?
O6 K1 O1 60.00(9) . . ?
O3 K1 O1 119.28(9) . . ?
O5 K1 O1 118.71(9) . . ?
N1 K1 O1 71.00(10) . . ?
N5 K1 O1 108.03(10) . . ?
C27 O1 C26 111.7(3) . . ?
C27 O1 K1 110.5(3) . . ?
C26 O1 K1 112.5(3) . . ?
C29 O2 C28 111.6(3) . . ?
C29 O2 K1 115.1(3) . . ?
C28 O2 K1 116.7(2) . . ?
C30 O3 C31 111.5(3) . . ?
C30 O3 K1 113.7(3) . . ?
C31 O3 K1 114.6(3) . . ?
C21 O4 C32 110.4(3) . . ?
C21 O4 K1 115.9(3) . . ?
C32 O4 K1 116.8(3) . . ?
C23 O5 C22 110.6(4) . . ?
C23 O5 K1 113.0(3) . . ?
C22 O5 K1 112.3(3) . . ?
C25 O6 C24 112.4(4) . . ?
C25 O6 K1 116.0(3) . . ?
C24 O6 K1 114.4(3) . . ?
C7 N1 K1 131.0(3) . . ?
C17 N5 K1 121.5(3) . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 C7 121.6(4) . . ?
C6 C1 C7 118.0(4) . . ?
C1 C2 C3 119.7(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 C8 120.7(4) . . ?
C4 C3 C8 119.2(4) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 C9 118.6(4) . . ?
C3 C4 C9 120.9(4) . . ?
C6 C5 C4 119.4(4) . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 C10 120.2(4) . . ?
C1 C6 C10 119.7(4) . . ?
N1 C7 C1 176.3(5) . . ?
N2 C8 C3 174.2(4) . . ?
N3 C9 C4 176.8(5) . . ?
N4 C10 C6 178.2(5) . . ?
C12 C11 C16 120.0(4) . . ?
C12 C11 C17 121.0(4) . . ?
C16 C11 C17 119.0(4) . . ?
C13 C12 C11 119.9(4) . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 C18 119.1(4) . . ?
C14 C13 C18 120.7(4) . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 C19 118.5(4) . . ?
C13 C14 C19 121.3(4) . . ?
C16 C15 C14 118.8(4) . . ?
C15 C16 C11 120.9(4) . . ?
C15 C16 C20 120.7(4) . . ?
C11 C16 C20 118.4(4) . . ?
N5 C17 C11 176.1(5) . . ?
N6 C18 C13 177.2(5) . . ?
N7 C19 C14 177.2(5) . . ?
N8 C20 C16 176.8(5) . . ?
O4 C21 C22 109.8(4) . . ?
O5 C22 C21 109.5(4) . . ?
O5 C23 C24 108.9(4) . . ?
O6 C24 C23 108.7(4) . . ?
O6 C25 C26 108.7(4) . . ?
O1 C26 C25 108.9(4) . . ?
O1 C27 C28 109.3(4) . . ?
O2 C28 C27 109.4(4) . . ?
O2 C29 C30 108.6(4) . . ?
O3 C30 C29 109.6(4) . . ?
O3 C31 C32 109.3(4) . . ?
O4 C32 C31 109.1(4) . . ?
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
K1 O2 2.771(3) . ?
K1 O4 2.775(3) . ?
K1 O6 2.809(3) . ?
K1 O3 2.815(3) . ?
K1 O5 2.817(3) . ?
K1 N1 2.821(4) . ?
K1 N5 2.850(4) . ?
K1 O1 2.854(3) . ?
O1 C27 1.427(5) . ?
O1 C26 1.428(5) . ?
O2 C29 1.425(5) . ?
O2 C28 1.430(5) . ?
O3 C30 1.421(5) . ?
O3 C31 1.426(5) . ?
O4 C21 1.432(6) . ?
O4 C32 1.439(5) . ?
O5 C23 1.426(6) . ?
O5 C22 1.430(6) . ?
O6 C25 1.423(6) . ?
O6 C24 1.425(6) . ?
N1 C7 1.142(5) . ?
N2 C8 1.138(5) . ?
N3 C9 1.143(5) . ?
N4 C10 1.141(5) . ?
N5 C17 1.138(5) . ?
N6 C18 1.146(5) . ?
N7 C19 1.138(5) . ?
N8 C20 1.143(5) . ?
C1 C2 1.382(6) . ?
C1 C6 1.399(6) . ?
C1 C7 1.443(6) . ?
C2 C3 1.386(6) . ?
C3 C4 1.397(6) . ?
C3 C8 1.447(6) . ?
C4 C5 1.390(6) . ?
C4 C9 1.437(6) . ?
C5 C6 1.382(6) . ?
C6 C10 1.441(6) . ?
C11 C12 1.387(6) . ?
C11 C16 1.406(5) . ?
C11 C17 1.440(6) . ?
C12 C13 1.378(6) . ?
C13 C14 1.412(5) . ?
C13 C18 1.444(6) . ?
C14 C15 1.399(6) . ?
C14 C19 1.438(6) . ?
C15 C16 1.386(6) . ?
C16 C20 1.450(6) . ?
C21 C22 1.487(7) . ?
C23 C24 1.497(7) . ?
C25 C26 1.494(7) . ?
C27 C28 1.492(7) . ?
C29 C30 1.494(7) . ?
C31 C32 1.494(7) . ?
