#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:34:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180227 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/13/7111342.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111342
loop_
_publ_author_name
'Haberhauer, Gebhard'
'Oeser, Thomas'
'Rominger, Frank'
_publ_section_title
;
 A C3-symmetric molecular scaffold for the construction of large receptors
;
_journal_issue                   18
_journal_name_full               'Chemical Communications'
_journal_page_first              2044
_journal_page_last               2045
_journal_paper_doi               10.1039/b406335j
_journal_year                    2004
_chemical_formula_sum            'C49 H59 Cl2 N9 O3'
_chemical_formula_weight         892.95
_chemical_name_systematic
;
(2a)
;
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   13.5462(4)
_cell_length_b                   13.5462(4)
_cell_length_c                   14.8813(9)
_cell_measurement_temperature    100(2)
_cell_volume                     2364.87(17)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'ω 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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20642
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9668
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.1258
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0002P)²+16.6790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.2532
_reflns_number_gt                2989
_reflns_number_total             3014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b406335jsup1.cif
_cod_data_source_block           gh24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2364.9(2)
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               7111342
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
C1 C 0.6744(8) 0.8298(8) 0.2364(6) 0.044(2) Uani 1 1 d .
H1 H 0.6203 0.8196 0.2860 0.052 Uiso 1 1 calc R
C2 C 0.7328(8) 0.7598(7) 0.2599(5) 0.0336(19) Uani 1 1 d .
N3 N 0.8402(6) 0.7973(6) 0.2458(4) 0.0323(15) Uani 1 1 d .
C4 C 0.8558(7) 0.7118(6) 0.2801(5) 0.0299(17) Uani 1 1 d .
C5 C 0.7593(7) 0.6244(7) 0.3115(5) 0.0315(16) Uani 1 1 d .
N6 N 0.6796(6) 0.6563(6) 0.2985(4) 0.0328(15) Uani 1 1 d .
C7 C 0.7272(8) 0.5117(7) 0.3534(6) 0.040(2) Uani 1 1 d .
H7A H 0.7953 0.5044 0.3595 0.060 Uiso 1 1 calc R
H7B H 0.6713 0.4501 0.3152 0.060 Uiso 1 1 calc R
H7C H 0.6940 0.5069 0.4129 0.060 Uiso 1 1 calc R
C9 C 0.9710(8) 0.7196(7) 0.2777(5) 0.040(2) Uani 1 1 d .
N9 N 1.0517(6) 0.8114(6) 0.2322(4) 0.0384(16) Uani 1 1 d .
H9 H 1.0308 0.8517 0.1993 0.046 Uiso 1 1 calc R
O9 O 0.9887(5) 0.6482(4) 0.3136(4) 0.0356(13) Uani 1 1 d .
C10 C 0.6024(11) 0.7793(10) 0.1467(7) 0.068(3) Uani 1 1 d .
H10 H 0.5558 0.6948 0.1545 0.082 Uiso 1 1 calc R
C11 C 0.5212(8) 0.8224(9) 0.1355(8) 0.054(3) Uani 1 1 d .
H11A H 0.4791 0.7933 0.0791 0.081 Uiso 1 1 calc R
H11B H 0.5636 0.9059 0.1341 0.081 Uiso 1 1 calc R
H11C H 0.4675 0.7964 0.1859 0.081 Uiso 1 1 calc R
C12 C 0.6763(12) 0.8007(11) 0.0677(7) 0.080(4) Uani 1 1 d .
H12A H 0.7102 0.8807 0.0496 0.120 Uiso 1 1 calc R
H12B H 0.6309 0.7513 0.0181 0.120 Uiso 1 1 calc R
H12C H 0.7370 0.7843 0.0831 0.120 Uiso 1 1 calc R
C13 C 0.5627(6) 0.6001(7) 0.3312(5) 0.0318(17) Uani 1 1 d .
H13A H 0.5278 0.5173 0.3200 0.038 Uiso 1 1 calc R
H13B H 0.5197 0.6276 0.2954 0.038 Uiso 1 1 calc R
C14 C 0.5478(7) 0.6174(7) 0.4301(5) 0.0307(17) Uani 1 1 d U
C15 C 0.4576(8) 0.5380(8) 0.4774(6) 0.048(2) Uani 1 1 d U
H15 H 0.4047 0.4682 0.4495 0.058 Uiso 1 1 calc R
C16 C 0.4417(8) 0.5577(11) 0.5662(8) 0.069(4) Uani 1 1 d .
H16 H 0.3777 0.5023 0.5990 0.083 Uiso 1 1 calc R
C17 C 0.5199(9) 0.6587(11) 0.6061(7) 0.062(3) Uani 1 1 d .
H17 H 0.5100 0.6720 0.6673 0.074 Uiso 1 1 calc R
C18 C 0.6105(7) 0.7394(8) 0.5600(6) 0.043(2) Uani 1 1 d .
H18 H 0.6633 0.8090 0.5882 0.051 Uiso 1 1 calc R
C19 C 0.6249(7) 0.7195(7) 0.4725(6) 0.0358(19) Uani 1 1 d .
H19 H 0.6883 0.7759 0.4398 0.043 Uiso 1 1 calc R
C50 C 0.9936(19) 1.0261(11) 0.4028(14) 0.031(6) Uani 0.33 1 d PDU
H50A H 1.0136 1.0181 0.3402 0.037 Uiso 0.33 1 calc PR
H50B H 0.9286 1.0402 0.4015 0.037 Uiso 0.33 1 calc PR
Cl51 Cl 0.9586(8) 0.9010(7) 0.4663(6) 0.070(3) Uani 0.33 1 d PD
Cl52 Cl 1.1122(8) 1.1389(7) 0.4582(6) 0.072(3) Uani 0.33 1 d PD
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
N9 C1 C2 108.8(7) 3_675 .
N9 C1 C10 115.0(9) 3_675 .
C2 C1 C10 108.5(7) . .
N9 C1 H1 108.1 3_675 .
C2 C1 H1 108.1 . .
C10 C1 H1 108.1 . .
N3 C2 N6 112.9(7) . .
N3 C2 C1 122.7(7) . .
N6 C2 C1 124.3(8) . .
C2 N3 C4 103.0(7) . .
C5 C4 N3 112.5(7) . .
C5 C4 C9 126.1(7) . .
N3 C4 C9 121.3(7) . .
C4 C5 N6 104.4(7) . .
C4 C5 C7 135.0(8) . .
N6 C5 C7 120.7(8) . .
C2 N6 C5 107.2(7) . .
C2 N6 C13 124.4(7) . .
C5 N6 C13 127.8(7) . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O9 C9 N9 123.6(9) . .
O9 C9 C4 122.4(8) . .
N9 C9 C4 114.0(8) . .
C9 N9 C1 121.9(8) . 2_765
C9 N9 H9 119.0 . .
C1 N9 H9 119.0 2_765 .
C12 C10 C11 113.3(10) . .
C12 C10 C1 111.9(10) . .
C11 C10 C1 109.8(8) . .
C12 C10 H10 107.2 . .
C11 C10 H10 107.2 . .
C1 C10 H10 107.2 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N6 C13 C14 115.9(6) . .
N6 C13 H13A 108.3 . .
C14 C13 H13A 108.3 . .
N6 C13 H13B 108.3 . .
C14 C13 H13B 108.3 . .
H13A C13 H13B 107.4 . .
C15 C14 C19 118.8(8) . .
C15 C14 C13 121.2(8) . .
C19 C14 C13 119.9(7) . .
C14 C15 C16 120.5(9) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C17 C16 C15 119.1(10) . .
C17 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
C18 C17 C16 121.3(10) . .
C18 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
C17 C18 C19 119.1(9) . .
C17 C18 H18 120.5 . .
C19 C18 H18 120.5 . .
C18 C19 C14 121.1(9) . .
C18 C19 H19 119.4 . .
C14 C19 H19 119.4 . .
Cl52 C50 Cl51 105.5(11) . .
Cl52 C50 H50A 110.6 . .
Cl51 C50 H50A 110.6 . .
Cl52 C50 H50B 110.6 . .
Cl51 C50 H50B 110.6 . .
H50A C50 H50B 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N9 1.435(12) 3_675
C1 C2 1.550(10) .
C1 C10 1.591(11) .
C1 H1 1.0000 .
C2 N3 1.297(12) .
C2 N6 1.343(10) .
N3 C4 1.374(9) .
C4 C5 1.335(12) .
C4 C9 1.511(12) .
C5 N6 1.363(10) .
C5 C7 1.498(11) .
N6 C13 1.456(10) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C9 O9 1.229(10) .
C9 N9 1.356(11) .
N9 C1 1.435(12) 2_765
N9 H9 0.8800 .
C10 C12 1.476(18) .
C10 C11 1.491(15) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.519(10) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.354(12) .
C14 C19 1.398(11) .
C15 C16 1.386(13) .
C15 H15 0.9500 .
C16 C17 1.378(15) .
C16 H16 0.9500 .
C17 C18 1.353(15) .
C17 H17 0.9500 .
C18 C19 1.364(12) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C50 Cl52 1.772(18) .
C50 Cl51 1.785(16) .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N9 C1 C2 N3 -22.2(11) 3_675 .
C10 C1 C2 N3 103.5(10) . .
N9 C1 C2 N6 156.3(8) 3_675 .
C10 C1 C2 N6 -78.0(11) . .
N6 C2 N3 C4 -1.5(8) . .
C1 C2 N3 C4 177.1(7) . .
C2 N3 C4 C5 1.7(8) . .
C2 N3 C4 C9 179.9(7) . .
N3 C4 C5 N6 -1.2(9) . .
C9 C4 C5 N6 -179.3(7) . .
N3 C4 C5 C7 178.8(8) . .
C9 C4 C5 C7 0.7(14) . .
N3 C2 N6 C5 0.9(9) . .
C1 C2 N6 C5 -177.8(7) . .
N3 C2 N6 C13 172.5(6) . .
C1 C2 N6 C13 -6.1(11) . .
C4 C5 N6 C2 0.3(8) . .
C7 C5 N6 C2 -179.8(7) . .
C4 C5 N6 C13 -171.0(7) . .
C7 C5 N6 C13 8.9(12) . .
C5 C4 C9 O9 -7.3(12) . .
N3 C4 C9 O9 174.7(7) . .
C5 C4 C9 N9 172.3(7) . .
N3 C4 C9 N9 -5.7(10) . .
O9 C9 N9 C1 -11.9(12) . 2_765
C4 C9 N9 C1 168.5(7) . 2_765
N9 C1 C10 C12 53.5(12) 3_675 .
C2 C1 C10 C12 -68.5(12) . .
N9 C1 C10 C11 -73.2(12) 3_675 .
C2 C1 C10 C11 164.8(10) . .
C2 N6 C13 C14 -93.8(9) . .
C5 N6 C13 C14 76.2(10) . .
N6 C13 C14 C15 -151.7(8) . .
N6 C13 C14 C19 31.7(10) . .
C19 C14 C15 C16 0.2(14) . .
C13 C14 C15 C16 -176.4(9) . .
C14 C15 C16 C17 -0.9(17) . .
C15 C16 C17 C18 1.1(17) . .
C16 C17 C18 C19 -0.6(14) . .
C17 C18 C19 C14 0.0(12) . .
C15 C14 C19 C18 0.2(12) . .
C13 C14 C19 C18 176.9(7) . .
