#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/12/2231250.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_2231250
loop_
_publ_author_name
'Yang, Qin-wan'
'Shi, Jingu'
'Pang, Tao'
_publ_section_title
;
 1,6-Bis(prop-2-yn-1-yloxy)naphthalene
;
_journal_coeditor_code           PK2330
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2054
_journal_paper_doi               10.1107/S1600536811027310
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 O2'
_chemical_formula_moiety         'C16 H12 O2'
_chemical_formula_sum            'C16 H12 O2'
_chemical_formula_weight         236.26
_chemical_name_systematic
;
1,6-Bis(prop-2-yn-1-yloxy)naphthalene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 95.459(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1472(9)
_cell_length_b                   10.3788(19)
_cell_length_c                   23.409(4)
_cell_measurement_reflns_used    1759
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.63
_cell_volume                     1244.9(4)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1180
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7491
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0446P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                1636
_reflns_number_total             2306
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2330.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231250
_cod_database_fobs_code          2231250
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_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
_atom_site_symmetry_multiplicity
C C1 0.6519(3) 0.40676(17) 0.23456(7) 0.0423(4) Uani d . 1 1
C C2 0.8336(3) 0.30562(16) 0.23889(8) 0.0466(5) Uani d . 1 1
H H2 0.8254 0.2419 0.2108 0.056 Uiso calc R 1 1
C C3 1.0218(3) 0.29989(16) 0.28383(8) 0.0449(5) Uani d . 1 1
H H3 1.1412 0.2324 0.2859 0.054 Uiso calc R 1 1
C C4 1.0385(3) 0.39506(15) 0.32738(7) 0.0398(4) Uani d . 1 1
C C5 1.2313(4) 0.39288(17) 0.37514(8) 0.0457(5) Uani d . 1 1
C C6 1.2356(4) 0.48592(18) 0.41649(8) 0.0548(5) Uani d . 1 1
H H6 1.3595 0.4829 0.4481 0.066 Uiso calc R 1 1
C C7 1.0524(4) 0.58592(19) 0.41099(8) 0.0605(6) Uani d . 1 1
H H7 1.0583 0.6494 0.4391 0.073 Uiso calc R 1 1
C C8 0.8668(4) 0.59320(18) 0.36603(8) 0.0532(5) Uani d . 1 1
H H8 0.7474 0.6607 0.3635 0.064 Uiso calc R 1 1
C C9 0.8560(3) 0.49704(16) 0.32270(7) 0.0420(5) Uani d . 1 1
C C10 0.6626(3) 0.50095(16) 0.27556(7) 0.0442(5) Uani d . 1 1
H H10 0.5421 0.5680 0.2724 0.053 Uiso calc R 1 1
C C11 0.2933(4) 0.50677(18) 0.18126(8) 0.0514(5) Uani d . 1 1
H H11A 0.3888 0.5864 0.1775 0.062 Uiso calc R 1 1
H H11B 0.1976 0.5134 0.2149 0.062 Uiso calc R 1 1
C C12 0.1124(4) 0.48650(19) 0.13036(9) 0.0582(6) Uani d . 1 1
C C13 -0.0400(5) 0.4787(2) 0.09085(10) 0.0813(8) Uani d . 1 1
H H13 -0.1625 0.4725 0.0591 0.098 Uiso calc R 1 1
C C14 1.6025(4) 0.2831(2) 0.42217(8) 0.0543(5) Uani d . 1 1
H H14A 1.6820 0.3672 0.4288 0.065 Uiso calc R 1 1
H H14B 1.7370 0.2243 0.4119 0.065 Uiso calc R 1 1
C C15 1.5032(4) 0.23846(19) 0.47507(9) 0.0558(5) Uani d . 1 1
C C16 1.4286(5) 0.2017(2) 0.51684(11) 0.0820(8) Uani d . 1 1
H H16 1.3683 0.1719 0.5506 0.098 Uiso calc R 1 1
O O1 0.4707(2) 0.40117(12) 0.18760(5) 0.0510(4) Uani d . 1 1
O O2 1.4033(2) 0.29188(12) 0.37524(5) 0.0534(4) Uani d . 1 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
C10 C1 O1 124.83(16)
C10 C1 C2 120.12(17)
O1 C1 C2 115.05(15)
C3 C2 C1 120.58(16)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 121.04(16)
C2 C3 H3 119.5
C4 C3 H3 119.5
C9 C4 C3 118.18(16)
C9 C4 C5 118.81(16)
C3 C4 C5 123.01(16)
C6 C5 O2 124.88(17)
C6 C5 C4 120.59(17)
O2 C5 C4 114.53(15)
C5 C6 C7 119.56(18)
C5 C6 H6 120.2
C7 C6 H6 120.2
C8 C7 C6 122.14(18)
C8 C7 H7 118.9
C6 C7 H7 118.9
C7 C8 C9 119.51(18)
C7 C8 H8 120.2
C9 C8 H8 120.2
C4 C9 C10 119.71(15)
C4 C9 C8 119.37(17)
C10 C9 C8 120.91(16)
C1 C10 C9 120.37(16)
C1 C10 H10 119.8
C9 C10 H10 119.8
O1 C11 C12 109.13(15)
O1 C11 H11A 109.9
C12 C11 H11A 109.9
O1 C11 H11B 109.9
C12 C11 H11B 109.9
H11A C11 H11B 108.3
C13 C12 C11 175.0(2)
C12 C13 H13 180.0
O2 C14 C15 112.83(15)
O2 C14 H14A 109.0
C15 C14 H14A 109.0
O2 C14 H14B 109.0
C15 C14 H14B 109.0
H14A C14 H14B 107.8
C16 C15 C14 178.7(2)
C15 C16 H16 180.0
C1 O1 C11 115.49(13)
C5 O2 C14 117.69(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C10 1.368(2)
C1 O1 1.3732(19)
C1 C2 1.403(2)
C2 C3 1.362(2)
C2 H2 0.9300
C3 C4 1.416(2)
C3 H3 0.9300
C4 C9 1.413(2)
C4 C5 1.423(2)
C5 C6 1.366(2)
C5 O2 1.372(2)
C6 C7 1.400(3)
C6 H6 0.9300
C7 C8 1.354(2)
C7 H7 0.9300
C8 C9 1.420(2)
C8 H8 0.9300
C9 C10 1.415(2)
C10 H10 0.9300
C11 O1 1.425(2)
C11 C12 1.456(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.157(3)
C13 H13 0.9300
C14 O2 1.433(2)
C14 C15 1.459(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.149(3)
C16 H16 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11B Cg1 1_455 0.97 2.75 3.602(2) 147
C14 H14A Cg2 1_655 0.97 2.76 3.457(2) 130
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
C10 C1 C2 C3 0.1(3)
O1 C1 C2 C3 -179.48(14)
C1 C2 C3 C4 0.3(3)
C2 C3 C4 C9 -0.6(2)
C2 C3 C4 C5 179.87(15)
C9 C4 C5 C6 1.7(2)
C3 C4 C5 C6 -178.81(17)
C9 C4 C5 O2 -178.55(14)
C3 C4 C5 O2 1.0(2)
O2 C5 C6 C7 178.69(17)
C4 C5 C6 C7 -1.6(3)
C5 C6 C7 C8 0.8(3)
C6 C7 C8 C9 -0.1(3)
C3 C4 C9 C10 0.5(2)
C5 C4 C9 C10 -179.96(15)
C3 C4 C9 C8 179.46(16)
C5 C4 C9 C8 -1.0(2)
C7 C8 C9 C4 0.3(3)
C7 C8 C9 C10 179.20(17)
O1 C1 C10 C9 179.34(14)
C2 C1 C10 C9 -0.2(3)
C4 C9 C10 C1 -0.1(2)
C8 C9 C10 C1 -179.04(17)
C10 C1 O1 C11 3.4(2)
C2 C1 O1 C11 -177.02(14)
C12 C11 O1 C1 -179.26(14)
C6 C5 O2 C14 0.0(3)
C4 C5 O2 C14 -179.77(14)
C15 C14 O2 C5 74.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656868
