#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/72/2217263.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2217263
loop_
_publ_author_name
'Wu Zhang'
'Qingxia Cui'
'Zhaowen Yu'
_publ_section_title
;
 2,2'-Bis(prop-2-ynyloxy)-1,1'-binaphthyl
;
_journal_coeditor_code           RK2069
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o317
_journal_page_last               o317
_journal_paper_doi               10.1107/S1600536807066718
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C26 H18 O2'
_chemical_formula_moiety         'C26 H18 O2'
_chemical_formula_sum            'C26 H18 O2'
_chemical_formula_weight         362.40
_chemical_name_systematic
;
2,2'-Bis(prop-2-ynyloxy)-1,1'-binaphthyl
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.317(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.866(2)
_cell_length_b                   8.8591(14)
_cell_length_c                   15.255(2)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.732
_cell_measurement_theta_min      5.374
_cell_volume                     1862.6(5)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2005)'
_computing_publication_material  'SHELXTL (Bruker, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ- and 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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6053
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0520
_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)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                1321
_reflns_number_total             2298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2069.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217263
_cod_database_fobs_code          2217263
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.53783(11) 0.02688(17) 0.28936(9) 0.0337(4) Uani d . 1
C C2 0.53225(11) -0.07606(18) 0.36043(9) 0.0351(4) Uani d . 1
C C3 0.45901(12) -0.18646(19) 0.36016(11) 0.0445(4) Uani d . 1
H H3 0.4137 -0.1965 0.3108 0.053 Uiso calc R 1
C C4 0.45339(14) -0.2796(2) 0.43149(12) 0.0541(5) Uani d . 1
H H4 0.4044 -0.3516 0.4299 0.065 Uiso calc R 1
C C5 0.52108(14) -0.2670(2) 0.50676(12) 0.0548(5) Uani d . 1
H H5 0.5161 -0.3290 0.5552 0.066 Uiso calc R 1
C C6 0.59366(13) -0.1641(2) 0.50849(10) 0.0483(5) Uani d . 1
H H6 0.6385 -0.1570 0.5584 0.058 Uiso calc R 1
C C7 0.60280(12) -0.06741(18) 0.43620(10) 0.0378(4) Uani d . 1
C C8 0.67634(12) 0.04140(19) 0.43727(10) 0.0422(4) Uani d . 1
H H8 0.7230 0.0469 0.4859 0.051 Uiso calc R 1
C C9 0.68140(12) 0.13914(19) 0.36920(10) 0.0416(4) Uani d . 1
H H9 0.7308 0.2105 0.3716 0.050 Uiso calc R 1
C C10 0.61115(12) 0.13157(18) 0.29481(9) 0.0364(4) Uani d . 1
O O1 0.61167(9) 0.22689(14) 0.22387(7) 0.0499(4) Uani d . 1
C C11 0.68206(13) 0.3446(2) 0.22703(11) 0.0506(5) Uani d . 1
H H11A 0.6807 0.3895 0.1689 0.061 Uiso calc R 1
H H11B 0.7460 0.3014 0.2421 0.061 Uiso calc R 1
C C12 0.66649(14) 0.4617(2) 0.29005(12) 0.0520(5) Uani d . 1
C C13 0.65408(17) 0.5555(3) 0.34144(16) 0.0713(6) Uani d . 1
H H13 0.6442 0.6302 0.3823 0.086 Uiso calc R 1
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'
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_site_symmetry_3
_geom_angle
C10 C1 C2 . 119.23(13)
C10 C1 C1 2_655 119.68(13)
C2 C1 C1 2_655 121.03(13)
C3 C2 C1 . 122.77(14)
C3 C2 C7 . 117.86(14)
C1 C2 C7 . 119.37(14)
C4 C3 C2 . 121.19(15)
C4 C3 H3 . 119.4
C2 C3 H3 . 119.4
C3 C4 C5 . 120.53(17)
C3 C4 H4 . 119.7
C5 C4 H4 . 119.7
C6 C5 C4 . 119.80(17)
C6 C5 H5 . 120.1
C4 C5 H5 . 120.1
C5 C6 C7 . 121.50(16)
C5 C6 H6 . 119.3
C7 C6 H6 . 119.3
C8 C7 C6 . 122.37(15)
C8 C7 C2 . 118.53(14)
C6 C7 C2 . 119.05(16)
C9 C8 C7 . 121.84(14)
C9 C8 H8 . 119.1
C7 C8 H8 . 119.1
C8 C9 C10 . 119.60(15)
C8 C9 H9 . 120.2
C10 C9 H9 . 120.2
C1 C10 O1 . 115.85(13)
C1 C10 C9 . 121.43(14)
O1 C10 C9 . 122.72(14)
C10 O1 C11 . 119.09(12)
O1 C11 C12 . 113.29(15)
O1 C11 H11A . 108.9
C12 C11 H11A . 108.9
O1 C11 H11B . 108.9
C12 C11 H11B . 108.9
H11A C11 H11B . 107.7
C13 C12 C11 . 179.5(2)
C12 C13 H13 . 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C10 . 1.372(2)
C1 C2 . 1.425(2)
C1 C1 2_655 1.505(3)
C2 C3 . 1.410(2)
C2 C7 . 1.432(2)
C3 C4 . 1.375(2)
C3 H3 . 0.9300
C4 C5 . 1.405(3)
C4 H4 . 0.9300
C5 C6 . 1.356(3)
C5 H5 . 0.9300
C6 C7 . 1.413(2)
C6 H6 . 0.9300
C7 C8 . 1.402(2)
C8 C9 . 1.360(2)
C8 H8 . 0.9300
C9 C10 . 1.413(2)
C9 H9 . 0.9300
C10 O1 . 1.3734(18)
O1 C11 . 1.425(2)
C11 C12 . 1.447(2)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C13 . 1.168(3)
C13 H13 . 0.9300
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_site_symmetry_1
_geom_torsion
C10 C1 C2 C3 . 179.70(15)
C1 C1 C2 C3 2_655 2.5(2)
C10 C1 C2 C7 . 0.4(2)
C1 C1 C2 C7 2_655 -176.80(14)
C1 C2 C3 C4 . -177.15(16)
C7 C2 C3 C4 . 2.1(2)
C2 C3 C4 C5 . -0.1(3)
C3 C4 C5 C6 . -1.3(3)
C4 C5 C6 C7 . 0.5(3)
C5 C6 C7 C8 . 178.90(17)
C5 C6 C7 C2 . 1.6(3)
C3 C2 C7 C8 . 179.73(15)
C1 C2 C7 C8 . -0.9(2)
C3 C2 C7 C6 . -2.8(2)
C1 C2 C7 C6 . 176.48(15)
C6 C7 C8 C9 . -176.48(15)
C2 C7 C8 C9 . 0.9(2)
C7 C8 C9 C10 . -0.2(2)
C2 C1 C10 O1 . -179.93(13)
C1 C1 C10 O1 2_655 -2.7(2)
C2 C1 C10 C9 . 0.2(2)
C1 C1 C10 C9 2_655 177.49(15)
C8 C9 C10 C1 . -0.4(2)
C8 C9 C10 O1 . 179.83(15)
C1 C10 O1 C11 . 176.21(15)
C9 C10 O1 C11 . -4.0(2)
C10 O1 C11 C12 . -68.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11175897
