#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204574.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_7204574
loop_
_publ_author_name
'Guo, Fang'
'Guo, Wen Sheng'
'Toda, Fumio'
_publ_section_title
;
 Supramolecular stereoisomer -- the conformational isomer of
 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol in the different inclusion
 compounds
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              45
_journal_paper_doi               10.1039/b211416j
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C25 H37.5 N O2'
_chemical_formula_weight         384.06
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_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                 105.954(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.220(3)
_cell_length_b                   10.568(4)
_cell_length_c                   15.517(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2084.4(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4403
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             842
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                1870
_reflns_number_total             3469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211416j.txt
_cod_data_source_block           samp304
_cod_original_cell_volume        2084.3(10)
_cod_original_formula_sum        'C25 H37.50 N O2'
_cod_database_code               7204574
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
O1 O 0.74778(16) 0.86360(19) 0.19251(12) 0.0492(6) Uani 1 1 d . . .
H1O H 0.770(3) 0.939(4) 0.172(2) 0.090(12) Uiso 1 1 d . . .
C1 C 0.6823(2) 0.7972(2) 0.11812(16) 0.0395(7) Uani 1 1 d . . .
C2 C 0.6016(2) 0.8851(3) 0.06497(18) 0.0433(7) Uani 1 1 d . . .
C3 C 0.5376(2) 0.9571(3) 0.02394(19) 0.0450(7) Uani 1 1 d . . .
C7 C 0.6291(2) 0.6905(2) 0.15614(17) 0.0400(7) Uani 1 1 d . . .
C8 C 0.5345(3) 0.6400(3) 0.1078(2) 0.0567(9) Uani 1 1 d . . .
H8 H 0.506(2) 0.672(3) 0.0499(19) 0.068(10) Uiso 1 1 d . . .
C9 C 0.4866(3) 0.5431(4) 0.1420(3) 0.0719(11) Uani 1 1 d . . .
H9 H 0.421(3) 0.515(4) 0.108(2) 0.105(14) Uiso 1 1 d . . .
C10 C 0.5333(4) 0.4962(4) 0.2257(3) 0.0715(11) Uani 1 1 d . . .
H10 H 0.496(3) 0.427(4) 0.247(2) 0.096(12) Uiso 1 1 d . . .
C11 C 0.6271(4) 0.5434(3) 0.2735(3) 0.0736(11) Uani 1 1 d . . .
H11 H 0.661(2) 0.508(3) 0.333(2) 0.077(10) Uiso 1 1 d . . .
C12 C 0.6765(3) 0.6391(3) 0.2396(2) 0.0574(9) Uani 1 1 d . . .
H12 H 0.742(2) 0.674(2) 0.2736(16) 0.046(8) Uiso 1 1 d . . .
C13 C 0.7475(2) 0.7401(2) 0.05977(17) 0.0370(7) Uani 1 1 d . . .
C14 C 0.8522(2) 0.7117(3) 0.0975(2) 0.0515(8) Uani 1 1 d . . .
H14 H 0.881(2) 0.733(2) 0.1614(18) 0.054(8) Uiso 1 1 d . . .
C15 C 0.9106(3) 0.6554(3) 0.0474(3) 0.0648(10) Uani 1 1 d . . .
H15 H 0.982(3) 0.635(3) 0.076(2) 0.090(12) Uiso 1 1 d . . .
C16 C 0.8661(3) 0.6262(3) -0.0412(3) 0.0648(10) Uani 1 1 d . . .
H16 H 0.907(2) 0.587(3) -0.078(2) 0.077(10) Uiso 1 1 d . . .
C17 C 0.7614(3) 0.6535(3) -0.0798(2) 0.0575(9) Uani 1 1 d . . .
H17 H 0.728(2) 0.638(3) -0.1458(19) 0.065(9) Uiso 1 1 d . . .
C18 C 0.7029(3) 0.7112(3) -0.02951(19) 0.0466(8) Uani 1 1 d . . .
H18 H 0.630(2) 0.735(3) -0.0561(18) 0.055(9) Uiso 1 1 d . . .
C1A C 0.7675(2) 0.2132(3) 0.19226(19) 0.0499(8) Uani 1 1 d . . .
O2A O 0.81189(16) 0.10606(17) 0.15632(12) 0.0527(6) Uani 1 1 d . . .
C3A C 0.8692(2) 0.1410(3) 0.09157(19) 0.0494(8) Uani 1 1 d . . .
C4A C 0.9171(4) 0.3455(4) 0.1741(3) 0.0701(10) Uani 1 1 d . . .
H2A H 0.996(3) 0.328(4) 0.193(2) 0.104(13) Uiso 1 1 d . . .
H4A H 0.908(3) 0.437(4) 0.167(2) 0.103(14) Uiso 1 1 d . . .
C5A C 0.8571(3) 0.3013(4) 0.2391(2) 0.0675(10) Uani 1 1 d . . .
H5B H 0.904(3) 0.250(3) 0.284(2) 0.080(12) Uiso 1 1 d . . .
H5A H 0.823(3) 0.378(4) 0.266(2) 0.103(13) Uiso 1 1 d . . .
C6A C 0.6938(3) 0.2816(4) 0.1133(3) 0.0657(10) Uani 1 1 d . . .
H6A H 0.632(3) 0.216(3) 0.082(2) 0.096(12) Uiso 1 1 d . . .
H6B H 0.662(3) 0.354(3) 0.139(2) 0.084(11) Uiso 1 1 d . . .
C7A C 0.7548(3) 0.3313(4) 0.0500(3) 0.0690(10) Uani 1 1 d . . .
H7B H 0.755(3) 0.413(3) 0.056(2) 0.070(12) Uiso 1 1 d . . .
H7A H 0.720(3) 0.292(3) -0.015(2) 0.092(12) Uiso 1 1 d . . .
C8A C 0.8678(3) 0.2848(3) 0.0827(2) 0.0571(9) Uani 1 1 d . . .
H8A H 0.910(3) 0.305(3) 0.032(2) 0.104(12) Uiso 1 1 d . . .
C9A C 0.7122(4) 0.1588(4) 0.2561(3) 0.0811(13) Uani 1 1 d . . .
H9B H 0.771(3) 0.109(3) 0.308(2) 0.084(12) Uiso 1 1 d . . .
H9A H 0.650(3) 0.107(4) 0.219(2) 0.105(14) Uiso 1 1 d . . .
H9C H 0.675(3) 0.223(4) 0.280(2) 0.106(14) Uiso 1 1 d . . .
C10A C 0.8151(5) 0.0750(4) 0.0041(3) 0.0785(12) Uani 1 1 d . . .
H10A H 0.829(3) -0.019(4) 0.015(2) 0.101(13) Uiso 1 1 d . . .
H10C H 0.848(3) 0.097(3) -0.041(2) 0.086(12) Uiso 1 1 d . . .
H10B H 0.734(4) 0.091(4) -0.015(3) 0.128(18) Uiso 1 1 d . . .
C11A C 0.9800(4) 0.0880(5) 0.1266(4) 0.0858(13) Uani 1 1 d . . .
H11C H 1.012(3) 0.126(4) 0.185(3) 0.119(17) Uiso 1 1 d . . .
H11B H 1.029(4) 0.110(5) 0.085(3) 0.150(19) Uiso 1 1 d . . .
H11A H 0.974(3) -0.007(5) 0.128(3) 0.133(18) 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'
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
O1 C1 C2 109.1(2) . . ?
O1 C1 C7 107.0(2) . . ?
C2 C1 C7 109.8(2) . . ?
O1 C1 C13 110.9(2) . . ?
C2 C1 C13 110.7(2) . . ?
C7 C1 C13 109.2(2) . . ?
C3 C2 C1 178.6(3) . . ?
C2 C3 C3 179.5(4) . 3_675 ?
C8 C7 C12 117.8(3) . . ?
C8 C7 C1 121.4(2) . . ?
C12 C7 C1 120.8(3) . . ?
C7 C8 C9 121.4(3) . . ?
C10 C9 C8 119.8(4) . . ?
C11 C10 C9 119.6(4) . . ?
C10 C11 C12 121.2(4) . . ?
C11 C12 C7 120.2(4) . . ?
C14 C13 C18 118.6(3) . . ?
C14 C13 C1 119.7(2) . . ?
C18 C13 C1 121.6(3) . . ?
C15 C14 C13 120.6(3) . . ?
C16 C15 C14 120.8(4) . . ?
C15 C16 C17 119.4(4) . . ?
C16 C17 C18 119.8(3) . . ?
C17 C18 C13 120.8(3) . . ?
O2A C1A C9A 106.1(3) . . ?
O2A C1A C6A 107.3(2) . . ?
C9A C1A C6A 113.2(3) . . ?
O2A C1A C5A 108.4(3) . . ?
C9A C1A C5A 112.0(3) . . ?
C6A C1A C5A 109.6(3) . . ?
C1A O2A C3A 114.0(2) . . ?
O2A C3A C10A 107.0(3) . . ?
O2A C3A C11A 106.9(3) . . ?
C10A C3A C11A 108.7(4) . . ?
O2A C3A C8A 108.5(2) . . ?
C10A C3A C8A 112.7(3) . . ?
C11A C3A C8A 112.7(3) . . ?
C5A C4A C8A 108.6(3) . . ?
C4A C5A C1A 110.5(3) . . ?
C1A C6A C7A 110.3(3) . . ?
C8A C7A C6A 108.5(3) . . ?
C7A C8A C3A 109.8(3) . . ?
C7A C8A C4A 107.7(3) . . ?
C3A C8A C4A 110.1(3) . . ?
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
O1 C1 1.423(3) . ?
C1 C2 1.482(4) . ?
C1 C7 1.531(4) . ?
C1 C13 1.535(4) . ?
C2 C3 1.185(3) . ?
C3 C3 1.399(6) 3_675 ?
C7 C8 1.377(4) . ?
C7 C12 1.385(4) . ?
C8 C9 1.383(5) . ?
C9 C10 1.369(5) . ?
C10 C11 1.353(5) . ?
C11 C12 1.383(5) . ?
C13 C14 1.379(4) . ?
C13 C18 1.383(4) . ?
C14 C15 1.373(4) . ?
C15 C16 1.372(5) . ?
C16 C17 1.379(5) . ?
C17 C18 1.382(4) . ?
C1A O2A 1.455(3) . ?
C1A C9A 1.498(4) . ?
C1A C6A 1.521(4) . ?
C1A C5A 1.525(4) . ?
O2A C3A 1.462(3) . ?
C3A C10A 1.519(5) . ?
C3A C11A 1.522(5) . ?
C3A C8A 1.525(4) . ?
C4A C5A 1.518(5) . ?
C4A C8A 1.529(5) . ?
C6A C7A 1.526(5) . ?
C7A C8A 1.521(5) . ?
