#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/76/7107642.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_7107642
loop_
_publ_author_name
'Noriko Fujimoto'
'Mio Matsumura'
'Isao Azumaya'
'Shizuka Nishiyama'
'Hyuma Masu'
'Hiroyuki Kagechika'
'Aya Tanatani'
_publ_section_title
;
 Molecular chirality and chiral capsule-type dimer formation of cyclic
 triamides via hydrogen-bonding interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              4809
_journal_paper_doi               10.1039/c2cc18177k
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C39 H45 N3 O9, 1.5(C2N)'
_chemical_formula_sum            'C42 H45 N4.5 O9'
_chemical_formula_weight         756.83
_chemical_name_systematic
;
?
;
_space_group_IT_number           176
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 6c'
_symmetry_space_group_name_H-M   'P 63/m'
_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            4
_cell_length_a                   16.5789(8)
_cell_length_b                   16.5789(8)
_cell_length_c                   19.1248(9)
_cell_measurement_reflns_used    6239
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.56
_cell_measurement_theta_min      2.56
_cell_volume                     4552.4(4)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22648
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1602
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_platon_squeeze_details
;
;
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0797
_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)+(0.1822P)²+1.9114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2654
_refine_ls_wR_factor_ref         0.2769
_reflns_number_gt                2574
_reflns_number_total             3351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc18177k.txt
_cod_data_source_block           2d(a0808281mas)
_cod_original_sg_symbol_H-M      'P6(3)/m '
_cod_original_formula_sum        'C42 H45 N4.50 O9'
_cod_database_code               7107642
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'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
C15A C 0.9902(6) 0.4096(9) 0.7500 0.090(4) Uani 0.327(6) 1 d PU A 1
C14A C 0.9016(7) 0.4033(11) 0.7500 0.097(4) Uani 0.327(6) 1 d PU A 1
N2A N 0.8318(12) 0.3955(17) 0.7500 0.163(9) Uani 0.327(6) 1 d PU A 1
N2B N 0.7438(8) 0.3540(8) 0.7500 0.061(4) Uani 0.173(6) 1 d PDU A 2
C14B C 0.8158(15) 0.342(3) 0.7500 0.134(12) Uani 0.173(6) 1 d PDU A 2
C15B C 0.911(2) 0.348(4) 0.7500 0.177(16) Uani 0.173(6) 1 d PDU A 2
C1 C 0.90159(15) 0.45012(16) 0.56903(11) 0.0303(5) Uani 1 1 d . . .
C2 C 0.83590(15) 0.36162(16) 0.53150(12) 0.0299(5) Uani 1 1 d . . .
C3 C 0.84269(14) 0.35329(16) 0.45969(12) 0.0308(5) Uani 1 1 d . . .
H3 H 0.8881 0.4046 0.4334 0.037 Uiso 1 1 calc R . .
C4 C 0.78278(16) 0.26957(16) 0.42645(12) 0.0324(5) Uani 1 1 d . . .
C5 C 0.71695(16) 0.19323(16) 0.46445(13) 0.0340(5) Uani 1 1 d . . .
H5 H 0.6778 0.1355 0.4419 0.041 Uiso 1 1 calc R . .
C6 C 0.70964(15) 0.20310(16) 0.53587(12) 0.0327(5) Uani 1 1 d . . .
C7 C 0.76865(16) 0.28660(16) 0.56967(12) 0.0331(6) Uani 1 1 d . . .
H7 H 0.7630 0.2924 0.6186 0.040 Uiso 1 1 calc R . .
C8 C 0.78710(16) 0.26441(16) 0.34925(12) 0.0354(6) Uani 1 1 d . . .
C9 C 0.9266(2) 0.5993(2) 0.61832(17) 0.0539(8) Uani 1 1 d U . .
H9A H 0.9773 0.5957 0.6429 0.065 Uiso 1 1 calc R . .
H9B H 0.8839 0.5997 0.6543 0.065 Uiso 1 1 calc R . .
C10 C 0.9678(2) 0.6884(2) 0.5792(2) 0.0694(10) Uani 1 1 d U . .
H10A H 0.9175 0.6916 0.5536 0.083 Uiso 1 1 calc R . .
H10B H 1.0120 0.6891 0.5441 0.083 Uiso 1 1 calc R . .
C11 C 1.0187(3) 0.7748(3) 0.6255(4) 0.1019(18) Uani 1 1 d U . .
H11A H 0.9729 0.7785 0.6565 0.122 Uiso 1 1 calc R . .
H11B H 1.0637 0.7680 0.6555 0.122 Uiso 1 1 calc R . .
C12 C 1.0700(5) 0.8640(3) 0.5850(5) 0.140(3) Uani 1 1 d U . .
H12A H 1.0250 0.8726 0.5565 0.168 Uiso 1 1 calc R . .
H12B H 1.1146 0.8600 0.5528 0.168 Uiso 1 1 calc R . .
C13 C 1.1238(7) 0.9495(5) 0.6341(8) 0.238(6) Uani 1 1 d U . .
H13A H 1.1036 0.9949 0.6250 0.357 Uiso 1 1 calc R . .
H13B H 1.1908 0.9783 0.6253 0.357 Uiso 1 1 calc R . .
H13C H 1.1107 0.9291 0.6830 0.357 Uiso 1 1 calc R . .
N1 N 0.87481(13) 0.51471(15) 0.57494(10) 0.0364(5) Uani 1 1 d . . .
O1 O 0.97385(11) 0.45947(12) 0.59468(9) 0.0391(5) Uani 1 1 d . . .
O2 O 0.84318(13) 0.33827(14) 0.31713(9) 0.0499(6) Uani 1 1 d . . .
H2 H 0.8401 0.3275 0.2740 0.075 Uiso 0.50 1 calc PR . .
O3 O 0.73560(14) 0.18732(14) 0.31901(9) 0.0506(6) Uani 1 1 d . . .
H3A H 0.7448 0.1938 0.2757 0.076 Uiso 0.50 1 calc PR . .
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'
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
N2A C14A C15A 177.7(19) . .
N2B C14B C15B 169(4) . .
O1 C1 N1 123.4(2) . .
O1 C1 C2 119.9(2) . .
N1 C1 C2 116.64(18) . .
C3 C2 C7 119.9(2) . .
C3 C2 C1 120.92(19) . .
C7 C2 C1 119.2(2) . .
C2 C3 C4 119.8(2) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C3 C4 C5 120.8(2) . .
C3 C4 C8 118.8(2) . .
C5 C4 C8 120.4(2) . .
C6 C5 C4 118.8(2) . .
C6 C5 H5 120.6 . .
C4 C5 H5 120.6 . .
C5 C6 C7 121.0(2) . .
C5 C6 N1 118.9(2) . 3_665
C7 C6 N1 120.1(2) . 3_665
C2 C7 C6 119.7(2) . .
C2 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
O2 C8 O3 123.6(2) . .
O2 C8 C4 117.4(2) . .
O3 C8 C4 119.0(2) . .
N1 C9 C10 114.9(3) . .
N1 C9 H9A 108.5 . .
C10 C9 H9A 108.5 . .
N1 C9 H9B 108.5 . .
C10 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C9 C10 C11 113.9(4) . .
C9 C10 H10A 108.8 . .
C11 C10 H10A 108.8 . .
C9 C10 H10B 108.8 . .
C11 C10 H10B 108.8 . .
H10A C10 H10B 107.7 . .
C12 C11 C10 113.6(6) . .
C12 C11 H11A 108.9 . .
C10 C11 H11A 108.9 . .
C12 C11 H11B 108.9 . .
C10 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
C11 C12 C13 111.8(8) . .
C11 C12 H12A 109.3 . .
C13 C12 H12A 109.3 . .
C11 C12 H12B 109.3 . .
C13 C12 H12B 109.3 . .
H12A C12 H12B 107.9 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C1 N1 C6 121.09(19) . 2_655
C1 N1 C9 122.1(2) . .
C6 N1 C9 116.7(2) 2_655 .
C8 O2 H2 109.5 . .
C8 O3 H3A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C15A C14A 1.420(12) .
C14A N2A 1.097(17) .
N2B C14B 1.311(18) .
C14B C15B 1.528(18) .
C1 O1 1.231(3) .
C1 N1 1.353(3) .
C1 C2 1.502(3) .
C2 C3 1.390(3) .
C2 C7 1.391(3) .
C3 C4 1.392(3) .
C3 H3 0.9500 .
C4 C5 1.393(3) .
C4 C8 1.483(3) .
C5 C6 1.388(3) .
C5 H5 0.9500 .
C6 C7 1.392(3) .
C6 N1 1.439(3) 3_665
C7 H7 0.9500 .
C8 O2 1.266(3) .
C8 O3 1.267(3) .
C9 N1 1.479(3) .
C9 C10 1.483(5) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.529(6) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.499(9) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.557(10) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
N1 C6 1.439(3) 2_655
O2 H2 0.8400 .
O3 H3A 0.8400 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 14 0 ' '
2 0.000 0.000 0.250 191 26 ' '
3 0.000 0.000 0.500 14 0 ' '
4 0.000 0.000 0.750 191 26 ' '
5 0.333 0.666 0.750 24 1 ' '
6 0.667 0.333 0.250 24 1 ' '
