#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:46:32 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178977 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/00/4120081.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_4120081
loop_
_publ_author_name
'Jamie L. Culshaw'
'Ge Cheng'
'Marc Schmidtmann'
'Tom Hasell'
'Ming Liu'
'Dave J. Adams'
'Andrew I. Cooper'
_publ_contact_author_address
;
Department of Chemistry 
University of Liverpool
Crown Street
Liverpool, L69 7ZD, UK
;
_publ_contact_author_email       aicooper@liv.ac.uk
_publ_contact_author_name        'Andrew I. Cooper'
_publ_contact_author_phone       '+44 (0)151 794 3548'
_publ_section_title
;
 Dodecaamide Cages: Organic 12-Arm Building Blocks for Supramolecular
 Chemistry
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10007
_journal_page_last               10010
_journal_paper_doi               10.1021/ja403987j
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         '(C96 H132 Br12 N12 O12),12(CHCl3),H2O'
_chemical_formula_sum            'C108 H146 Br12 Cl36 N12 O13'
_chemical_formula_weight         4055.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           218
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  'P -4n 2 3'
_symmetry_space_group_name_H-M   'P -4 3 n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   20.3301(7)
_cell_length_b                   20.3301(7)
_cell_length_c                   20.3301(7)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.24
_cell_volume                     8402.7(5)
_computing_cell_refinement       'Bruker AXS SAINT V7.68A'
_computing_data_collection       'CrystalClear-SM Expert 2.0r6 (Rigaku, 2010)'
_computing_data_reduction        'Bruker AXS SAINT V7.68A'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            110955
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    3.485
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       'trigonal plate'
_exptl_crystal_F_000             4028
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
'refined as racemic twin BASF 0.40455 esd 0.01558'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0446
_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)+(0.0700P)²+11.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                2490
_reflns_number_total             2875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja403987j_si_005.cif
_cod_data_source_block           RC1d
_cod_database_code               4120081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, z+1/2, y+1/2'
'-x+1/2, z+1/2, -y+1/2'
'-x+1/2, -z+1/2, y+1/2'
'x+1/2, -z+1/2, -y+1/2'
'z+1/2, y+1/2, x+1/2'
'z+1/2, -y+1/2, -x+1/2'
'-z+1/2, y+1/2, -x+1/2'
'-z+1/2, -y+1/2, x+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
N1 N 0.52753(15) 0.23897(15) 0.56889(15) 0.0210(6) Uani 1 1 d . . .
O1 O 0.42670(15) 0.19652(17) 0.58145(15) 0.0392(7) Uani 1 1 d . . .
Br1 Br 0.57224(7) 0.08034(4) 0.57038(5) 0.0407(3) Uani 0.552(2) 1 d P A 1
Br2 Br 0.55757(12) 0.14643(10) 0.70133(8) 0.0446(4) Uani 0.448(2) 1 d P A 2
C1 C 0.59086(18) 0.32087(18) 0.66760(17) 0.0212(8) Uani 1 1 d . . .
H1 H 0.5531 0.2977 0.6826 0.025 Uiso 1 1 calc R . .
C2 C 0.62423(17) 0.29880(18) 0.61192(17) 0.0200(7) Uani 1 1 d . . .
C3 C 0.59942(19) 0.23985(18) 0.5730(2) 0.0232(8) Uani 1 1 d . . .
H3A H 0.6181 0.2413 0.5281 0.028 Uiso 1 1 calc R . .
H3B H 0.6148 0.1989 0.5944 0.028 Uiso 1 1 calc R . .
C4 C 0.4971(2) 0.29649(19) 0.5373(2) 0.0264(8) Uani 1 1 d . . .
H4A H 0.5181 0.3369 0.5547 0.032 Uiso 1 1 calc R . .
H4B H 0.4500 0.2979 0.5494 0.032 Uiso 1 1 calc R . .
C5 C 0.4864(2) 0.1909(2) 0.59013(19) 0.0278(9) Uani 1 1 d . A .
C6 C 0.5113(3) 0.1300(2) 0.6258(2) 0.0393(11) Uani 1 1 d D . .
C7 C 0.4524(3) 0.0873(2) 0.6453(3) 0.0573(16) Uani 1 1 d . A .
H7A H 0.4262 0.0773 0.6061 0.086 Uiso 1 1 calc R . .
H7B H 0.4251 0.1111 0.6772 0.086 Uiso 1 1 calc R . .
H7C H 0.4681 0.0463 0.6650 0.086 Uiso 1 1 calc R . .
C8 C 0.5483(12) 0.0872(12) 0.5731(11) 0.089(9) Uiso 0.448(2) 1 d PD A 2
H8A H 0.5653 0.0472 0.5939 0.134 Uiso 0.448(2) 1 calc PR A 2
H8B H 0.5849 0.1125 0.5546 0.134 Uiso 0.448(2) 1 calc PR A 2
H8C H 0.5177 0.0751 0.5378 0.134 Uiso 0.448(2) 1 calc PR A 2
C9 C 0.5515(14) 0.1389(15) 0.6932(10) 0.089(9) Uiso 0.552(2) 1 d PD A 1
H9A H 0.5647 0.0957 0.7099 0.134 Uiso 0.552(2) 1 calc PR A 1
H9B H 0.5235 0.1608 0.7258 0.134 Uiso 0.552(2) 1 calc PR A 1
H9C H 0.5907 0.1658 0.6851 0.134 Uiso 0.552(2) 1 calc PR A 1
C10 C 0.2804(3) 0.1860(3) 0.6072(3) 0.0572(15) Uani 1 1 d . . .
H10 H 0.3294 0.1826 0.6095 0.069 Uiso 1 1 calc R . .
Cl1 Cl 0.25986(9) 0.27049(9) 0.59785(8) 0.0693(5) Uani 1 1 d . . .
Cl2 Cl 0.24860(7) 0.15487(9) 0.68057(9) 0.0696(5) Uani 1 1 d . . .
Cl3 Cl 0.25457(11) 0.14202(12) 0.53858(10) 0.0926(6) Uani 1 1 d . . .
O2 O 0.5000 0.5000 0.5000 0.158(12) Uiso 1 12 d S . .
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'
Br Br -0.2901 2.4595 '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_
_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
C5 N1 C3 127.3(3) . .
C5 N1 C4 116.9(3) . .
C3 N1 C4 115.8(3) . .
C2 C1 C2 120.8(4) 6_566 .
C2 C1 H1 119.6 6_566 .
C2 C1 H1 119.6 . .
C1 C2 C1 119.2(4) 12_665 .
C1 C2 C3 119.9(3) 12_665 .
C1 C2 C3 120.9(3) . .
N1 C3 C2 111.7(3) . .
N1 C3 H3A 109.3 . .
C2 C3 H3A 109.3 . .
N1 C3 H3B 109.3 . .
C2 C3 H3B 109.3 . .
H3A C3 H3B 107.9 . .
N1 C4 C4 113.7(3) . 3_656
N1 C4 H4A 108.8 . .
C4 C4 H4A 108.8 3_656 .
N1 C4 H4B 108.8 . .
C4 C4 H4B 108.8 3_656 .
H4A C4 H4B 107.7 . .
O1 C5 N1 119.7(4) . .
O1 C5 C6 118.1(4) . .
N1 C5 C6 122.2(4) . .
C5 C6 C7 108.9(4) . .
C5 C6 C8 106.5(10) . .
C7 C6 C8 103.7(10) . .
C5 C6 C9 119.0(12) . .
C7 C6 C9 104.0(12) . .
C8 C6 C9 113.7(14) . .
C5 C6 Br2 115.0(3) . .
C7 C6 Br2 106.8(4) . .
C8 C6 Br2 115.3(10) . .
C9 C6 Br2 4.1(12) . .
C5 C6 Br1 110.8(3) . .
C7 C6 Br1 110.6(3) . .
C8 C6 Br1 11.0(9) . .
C9 C6 Br1 103.2(11) . .
Br2 C6 Br1 104.6(3) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
Cl3 C10 Cl2 112.9(3) . .
Cl3 C10 Cl1 109.9(3) . .
Cl2 C10 Cl1 110.8(4) . .
Cl3 C10 H10 107.7 . .
Cl2 C10 H10 107.7 . .
Cl1 C10 H10 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.357(5) .
N1 C3 1.464(5) .
N1 C4 1.470(5) .
O1 C5 1.231(5) .
Br1 C6 1.956(5) .
Br2 C6 1.831(6) .
C1 C2 1.377(5) 6_566
C1 C2 1.394(5) .
C1 H1 0.9500 .
C2 C1 1.377(5) 12_665
C2 C3 1.522(5) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C4 1.523(8) 3_656
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.522(6) .
C6 C7 1.531(7) .
C6 C8 1.573(16) .
C6 C9 1.606(16) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 Cl3 1.737(7) .
C10 Cl2 1.744(6) .
C10 Cl1 1.779(6) .
C10 H10 1.0000 .
