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#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/45/7114503.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_7114503
loop_
_publ_author_name
'Gibson (née Thomas), Susan E.'
'Jones, Jerome O.'
'Kalindjian, S. Barret'
'Knight, Jamie D.'
'Steed, Jonathan W.'
'Tozer, Matthew J.'
_publ_section_title
;
 Synthesis and structural analysis of dehydrophenylalanine cyclophanes
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1938
_journal_paper_doi               10.1039/b205752m
_journal_year                    2002
_chemical_formula_sum            'C52 H78.1 Cl3.9 N2 O8.7'
_chemical_formula_weight         1008.72
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.52(4)
_cell_angle_beta                 91.999(4)
_cell_angle_gamma                113.079(3)
_cell_formula_units_Z            1
_cell_length_a                   8.1987(4)
_cell_length_b                   8.8260(6)
_cell_length_c                   20.8707(13)
_cell_measurement_temperature    100(2)
_cell_volume                     1350.6(3)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'XSeed (Barbour, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_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  0.0937
_diffrn_reflns_av_sigmaI/netI    0.1472
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7441
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9484
_exptl_absorpt_correction_type   Scalepack
_exptl_absorpt_process_details   'Otwinowski & Minor, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4708
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.1299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0633P)²+10.5529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2724
_refine_ls_wR_factor_ref         0.2976
_reflns_number_gt                3141
_reflns_number_total             4708
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b205752m.txt
_cod_data_source_block           jk150a
_cod_original_cell_volume        1350.58(14)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C52 H78.10 Cl3.90 N2 O8.70'
_cod_database_code               7114503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.9802(6) 0.8122(6) 0.2134(2) 0.0275(11) Uani 1 1 d U A .
O2 O 1.0496(6) 0.7425(5) 0.3054(2) 0.0222(10) Uani 1 1 d U A .
O3 O 0.7153(6) 0.3616(6) 0.3694(2) 0.0299(12) Uani 1 1 d U . .
O4 O 0.6311(6) 0.5389(5) 0.32450(19) 0.0201(10) Uani 1 1 d U . .
N1 N 0.8029(6) 0.4262(6) 0.2726(2) 0.0153(11) Uani 1 1 d U . .
C1 C -0.9292(8) -1.3439(8) -0.2694(3) 0.0210(14) Uani 1 1 d U . .
H1A H -1.0480 -1.4258 -0.2634 0.025 Uiso 1 1 calc R . .
H1B H -0.9414 -1.3131 -0.3118 0.025 Uiso 1 1 calc R . .
C2 C -0.8712(8) -1.1864(8) -0.2140(3) 0.0213(14) Uani 1 1 d U . .
H2A H -0.8452 -1.2150 -0.1724 0.026 Uiso 1 1 calc R . .
H2B H -0.9718 -1.1514 -0.2091 0.026 Uiso 1 1 calc R . .
C3 C -0.7070(8) -1.0369(7) -0.2241(3) 0.0184(13) Uani 1 1 d U . .
H3A H -0.6178 -1.0783 -0.2419 0.022 Uiso 1 1 calc R . .
H3B H -0.7423 -0.9845 -0.2568 0.022 Uiso 1 1 calc R . .
C4 C -0.6223(8) -0.9035(8) -0.1597(3) 0.0202(14) Uani 1 1 d U . .
H4A H -0.5904 -0.9583 -0.1272 0.024 Uiso 1 1 calc R . .
H4B H -0.7131 -0.8638 -0.1423 0.024 Uiso 1 1 calc R . .
C5 C -0.4553(8) -0.7486(8) -0.1645(3) 0.0203(14) Uani 1 1 d U . .
H5A H -0.3660 -0.7863 -0.1847 0.024 Uiso 1 1 calc R . .
H5B H -0.4875 -0.6851 -0.1931 0.024 Uiso 1 1 calc R . .
C6 C -0.3748(8) -0.6335(8) -0.0964(3) 0.0210(14) Uani 1 1 d U . .
H6A H -0.3489 -0.7009 -0.0681 0.025 Uiso 1 1 calc R . .
H6B H -0.4661 -0.5972 -0.0773 0.025 Uiso 1 1 calc R . .
C7 C -0.2043(8) -0.4753(7) -0.0932(3) 0.0171(13) Uani 1 1 d U . .
H7A H -0.1116 -0.5085 -0.1129 0.021 Uiso 1 1 calc R . .
H7B H -0.2290 -0.4023 -0.1191 0.021 Uiso 1 1 calc R . .
C8 C -0.1364(8) -0.3775(8) -0.0222(3) 0.0181(13) Uani 1 1 d U . .
H8A H -0.1185 -0.4548 0.0030 0.022 Uiso 1 1 calc R . .
H8B H -0.2311 -0.3456 -0.0038 0.022 Uiso 1 1 calc R . .
C9 C 0.0369(8) -0.2172(7) -0.0103(3) 0.0160(13) Uani 1 1 d U . .
H9A H 0.1357 -0.2462 -0.0263 0.019 Uiso 1 1 calc R . .
H9B H 0.0227 -0.1369 -0.0348 0.019 Uiso 1 1 calc R . .
C10 C 0.0798(8) -0.1361(8) 0.0633(3) 0.0177(13) Uani 1 1 d U A .
H10A H 0.0858 -0.2220 0.0863 0.021 Uiso 1 1 calc R . .
H10B H -0.0222 -0.1102 0.0776 0.021 Uiso 1 1 calc R . .
C11 C 0.2501(7) 0.0246(7) 0.0876(3) 0.0145(13) Uani 1 1 d U . .
C12 C 0.2894(8) 0.0936(7) 0.1553(3) 0.0158(13) Uani 1 1 d U A 1
H12 H 0.2102 0.0392 0.1838 0.019 Uiso 1 1 calc R . .
C13 C 0.4386(8) 0.2370(7) 0.1820(3) 0.0165(13) Uani 1 1 d U . .
H13 H 0.4620 0.2787 0.2284 0.020 Uiso 1 1 calc R A 1
C14 C 0.5575(8) 0.3238(7) 0.1420(3) 0.0162(13) Uani 1 1 d U A .
C15 C 0.5160(8) 0.2577(8) 0.0740(3) 0.0184(14) Uani 1 1 d U . .
H15 H 0.5919 0.3156 0.0454 0.022 Uiso 1 1 calc R A .
C16 C 0.3673(7) 0.1103(7) 0.0472(3) 0.0148(13) Uani 1 1 d U A .
H16 H 0.3446 0.0668 0.0008 0.018 Uiso 1 1 calc R . .
C17 C 0.7140(8) 0.4826(8) 0.1694(3) 0.0188(14) Uani 1 1 d U . .
H17 H 0.7475 0.5612 0.1420 0.023 Uiso 1 1 calc R A .
C18 C 0.8158(8) 0.5319(7) 0.2274(3) 0.0149(13) Uani 1 1 d U A .
C19 C 0.9565(8) 0.7090(8) 0.2466(3) 0.0179(13) Uani 1 1 d U . .
C20 C 1.1820(9) 0.9149(8) 0.3276(3) 0.0305(17) Uani 1 1 d U . .
H20A H 1.2760 0.9355 0.2986 0.046 Uiso 1 1 calc R A .
H20B H 1.2347 0.9324 0.3728 0.046 Uiso 1 1 calc R . .
H20C H 1.1251 0.9936 0.3265 0.046 Uiso 1 1 calc R . .
C21 C 0.7170(8) 0.4360(8) 0.3268(3) 0.0176(13) Uani 1 1 d U . .
C22 C 0.5147(9) 0.5610(9) 0.3746(3) 0.0273(16) Uani 1 1 d U . .
C23 C 0.4452(10) 0.6782(9) 0.3506(3) 0.0318(17) Uani 1 1 d U . .
H23A H 0.5457 0.7848 0.3501 0.048 Uiso 1 1 calc R . .
H23B H 0.3633 0.7013 0.3803 0.048 Uiso 1 1 calc R . .
H23C H 0.3816 0.6245 0.3060 0.048 Uiso 1 1 calc R . .
C24 C 0.6244(11) 0.6443(10) 0.4425(3) 0.0381(19) Uani 1 1 d U . .
H24A H 0.6656 0.5650 0.4571 0.057 Uiso 1 1 calc R . .
H24B H 0.5501 0.6746 0.4740 0.057 Uiso 1 1 calc R . .
H24C H 0.7278 0.7466 0.4399 0.057 Uiso 1 1 calc R . .
C25 C 0.3617(9) 0.3903(9) 0.3736(3) 0.0332(17) Uani 1 1 d U . .
H25A H 0.2943 0.3418 0.3294 0.050 Uiso 1 1 calc R . .
H25B H 0.2821 0.4070 0.4056 0.050 Uiso 1 1 calc R . .
H25C H 0.4108 0.3130 0.3852 0.050 Uiso 1 1 calc R . .
Cl1S Cl 0.6089(5) 0.0518(5) 0.48748(17) 0.0555(10) Uiso 0.65 1 d P . 1
Cl3S Cl 0.9345(6) 0.0973(5) 0.4277(2) 0.0681(11) Uiso 0.65 1 d P B 1
Cl2S Cl 0.9364(6) 0.3440(5) 0.5411(2) 0.0681(11) Uiso 0.65 1 d P B 1
C1S C 0.792(3) 0.185(2) 0.4666(9) 0.065(5) Uiso 0.65 1 d P B 1
H1S H 0.7581 0.2461 0.4367 0.078 Uiso 0.65 1 calc PR B 1
O1S O 0.717(2) 0.238(2) 0.4844(9) 0.058(5) Uiso 0.35 1 d P C 2
H1S1 H 0.7313 0.3266 0.5123 0.070 Uiso 0.35 1 calc PR C 2
C2S C 0.873(4) 0.221(3) 0.4828(13) 0.040(6) Uiso 0.35 1 d P C 2
H2S1 H 0.9717 0.3332 0.4969 0.060 Uiso 0.35 1 calc PR C 2
H2S2 H 0.8810 0.1683 0.4379 0.060 Uiso 0.35 1 calc PR C 2
H2S3 H 0.8786 0.1503 0.5127 0.060 Uiso 0.35 1 calc PR C 2
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'
Cl Cl 0.1484 0.1585 '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
C19 O2 C20 114.6(5) . .
C21 O4 C22 120.9(5) . .
C21 N1 C18 121.8(5) . .
C21 N1 C1 119.2(5) . 2_545
C18 N1 C1 116.5(5) . 2_545
N1 C1 C2 113.1(5) 2_545 .
C1 C2 C3 114.3(5) . .
C4 C3 C2 111.7(5) . .
C3 C4 C5 115.7(5) . .
C6 C5 C4 110.5(5) . .
C5 C6 C7 116.4(5) . .
C8 C7 C6 110.3(5) . .
C7 C8 C9 116.9(5) . .
C10 C9 C8 108.8(5) . .
C9 C10 C11 118.5(5) . .
C12 C11 C16 117.4(5) . .
C12 C11 C10 117.5(5) . .
C16 C11 C10 125.0(5) . .
C13 C12 C11 122.0(5) . .
C12 C13 C14 121.2(5) . .
C15 C14 C13 117.0(5) . .
C15 C14 C17 120.8(5) . .
C13 C14 C17 122.1(5) . .
C16 C15 C14 121.7(5) . .
C15 C16 C11 120.7(5) . .
C18 C17 C14 129.0(6) . .
C17 C18 N1 124.8(5) . .
C17 C18 C19 118.2(5) . .
N1 C18 C19 117.0(5) . .
O1 C19 O2 123.7(6) . .
O1 C19 C18 123.8(6) . .
O2 C19 C18 112.4(5) . .
O3 C21 O4 125.7(6) . .
O3 C21 N1 124.7(6) . .
O4 C21 N1 109.5(5) . .
O4 C22 C23 101.9(5) . .
O4 C22 C24 110.2(5) . .
C23 C22 C24 111.2(6) . .
O4 C22 C25 110.0(5) . .
C23 C22 C25 110.9(6) . .
C24 C22 C25 112.1(6) . .
C1S Cl1S Cl1S 165.9(8) . 2_656
Cl1S C1S Cl3S 116.6(11) . .
Cl1S C1S Cl2S 110.4(10) . .
Cl3S C1S Cl2S 104.3(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C19 1.212(7) .
O2 C19 1.338(7) .
O2 C20 1.448(7) .
O3 C21 1.203(7) .
O4 C21 1.356(7) .
O4 C22 1.475(7) .
N1 C21 1.360(7) .
N1 C18 1.432(7) .
N1 C1 1.476(8) 2_545
C1 N1 1.476(8) 2_545
C1 C2 1.516(9) .
C2 C3 1.529(8) .
C3 C4 1.529(8) .
C4 C5 1.533(8) .
C5 C6 1.523(9) .
C6 C7 1.528(8) .
C7 C8 1.519(8) .
C8 C9 1.530(8) .
C9 C10 1.525(8) .
C10 C11 1.526(8) .
C11 C12 1.393(8) .
C11 C16 1.396(8) .
C12 C13 1.365(8) .
C13 C14 1.399(8) .
C14 C15 1.397(8) .
C14 C17 1.468(9) .
C15 C16 1.382(8) .
C17 C18 1.337(8) .
C18 C19 1.496(8) .
C22 C23 1.515(9) .
C22 C24 1.527(10) .
C22 C25 1.532(10) .
Cl1S C1S 1.642(19) .
Cl1S Cl1S 1.809(7) 2_656
Cl3S C1S 1.77(2) .
Cl2S C1S 1.867(19) .
O1S C2S 1.34(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1S H1S O3 1.00 1.99 2.98(2) 171.8
