#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/01/2220102.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_2220102
loop_
_publ_author_name
'Yang, Guo-Zhong'
'Li, Fu-An'
_publ_section_title
;
 2,3-Bis(prop-2-ynyloxy)naphthalene
;
_journal_coeditor_code           BV2111
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2383
_journal_paper_doi               10.1107/S1600536808037549
_journal_volume                  64
_journal_year                    2008
_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
;
2,3-bis(prop-2-ynyloxy)naphthalene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2921(12)
_cell_length_b                   9.0457(14)
_cell_length_c                   33.070(5)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.727
_cell_measurement_theta_min      2.748
_cell_volume                     2480.5(6)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12468
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0391
_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)+(0.0527P)²+0.338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                1782
_reflns_number_total             2182
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2111.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      ' P b c a'
_cod_database_code               2220102
_cod_database_fobs_code          2220102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 -0.1360(2) -0.0848(2) 0.32753(6) 0.0752(6) Uani d . 1
H H1 -0.1425 -0.1672 0.3108 0.090 Uiso calc R 1
C C2 -0.1277(2) 0.01867(18) 0.34856(5) 0.0574(4) Uani d . 1
C C3 -0.1181(2) 0.14633(16) 0.37505(5) 0.0554(4) Uani d . 1
H H3A -0.2249 0.1865 0.3798 0.066 Uiso calc R 1
H H3B -0.0720 0.1182 0.4009 0.066 Uiso calc R 1
C C4 0.00170(15) 0.38601(15) 0.37523(4) 0.0400(3) Uani d . 1
C C5 -0.05860(17) 0.42250(16) 0.41224(4) 0.0462(4) Uani d . 1
H H5 -0.1182 0.3532 0.4267 0.055 Uiso calc R 1
C C6 -0.03174(17) 0.56457(16) 0.42903(4) 0.0451(4) Uani d . 1
C C7 -0.0984(2) 0.60874(19) 0.46649(4) 0.0586(4) Uani d . 1
H H7 -0.1609 0.5422 0.4811 0.070 Uiso calc R 1
C C8 -0.0727(3) 0.7468(2) 0.48143(5) 0.0703(5) Uani d . 1
H H8 -0.1182 0.7741 0.5060 0.084 Uiso calc R 1
C C9 0.0218(2) 0.8480(2) 0.45997(5) 0.0696(5) Uani d . 1
H H9 0.0401 0.9417 0.4706 0.084 Uiso calc R 1
C C10 0.0875(2) 0.80997(18) 0.42353(5) 0.0577(4) Uani d . 1
H H10 0.1500 0.8782 0.4095 0.069 Uiso calc R 1
C C11 0.06147(17) 0.66812(16) 0.40699(4) 0.0443(3) Uani d . 1
C C12 0.12274(17) 0.62803(15) 0.36856(4) 0.0436(3) Uani d . 1
H H12 0.1830 0.6959 0.3538 0.052 Uiso calc R 1
C C13 0.09452(16) 0.49128(15) 0.35298(4) 0.0391(3) Uani d . 1
C C14 0.24207(18) 0.53826(15) 0.29190(4) 0.0447(3) Uani d . 1
H H14A 0.3080 0.4809 0.2735 0.054 Uiso calc R 1
H H14B 0.3139 0.5947 0.3092 0.054 Uiso calc R 1
C C15 0.14206(18) 0.64031(16) 0.26860(4) 0.0448(4) Uani d . 1
C C16 0.0667(2) 0.71916(18) 0.24743(5) 0.0575(4) Uani d . 1
H H16 0.0073 0.7814 0.2307 0.069 Uiso calc R 1
O O1 -0.01832(12) 0.25415(10) 0.35571(3) 0.0479(3) Uani d . 1
O O2 0.14871(12) 0.43928(10) 0.31646(3) 0.0471(3) Uani d . 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
C2 C1 H1 180.0
C1 C2 C3 179.39(17)
O1 C3 C2 107.72(12)
O1 C3 H3A 110.2
C2 C3 H3A 110.2
O1 C3 H3B 110.2
C2 C3 H3B 110.2
H3A C3 H3B 108.5
C5 C4 O1 126.24(12)
C5 C4 C13 119.93(13)
O1 C4 C13 113.83(11)
C4 C5 C6 120.91(13)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C11 118.51(14)
C7 C6 C5 122.53(14)
C11 C6 C5 118.93(12)
C8 C7 C6 121.10(16)
C8 C7 H7 119.4
C6 C7 H7 119.4
C7 C8 C9 120.29(16)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 120.41(17)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 120.64(16)
C9 C10 H10 119.7
C11 C10 H10 119.7
C10 C11 C12 121.72(14)
C10 C11 C6 119.03(13)
C12 C11 C6 119.23(13)
C13 C12 C11 120.74(13)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 O2 126.08(12)
C12 C13 C4 120.25(12)
O2 C13 C4 113.67(11)
O2 C14 C15 112.73(12)
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 175.37(15)
C15 C16 H16 180.0
C4 O1 C3 117.03(11)
C13 O2 C14 117.45(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.168(2)
C1 H1 0.9300
C2 C3 1.452(2)
C3 O1 1.4299(16)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.363(2)
C4 O1 1.3663(16)
C4 C13 1.4285(18)
C5 C6 1.418(2)
C5 H5 0.9300
C6 C7 1.414(2)
C6 C11 1.416(2)
C7 C8 1.360(2)
C7 H7 0.9300
C8 C9 1.399(3)
C8 H8 0.9300
C9 C10 1.367(2)
C9 H9 0.9300
C10 C11 1.412(2)
C10 H10 0.9300
C11 C12 1.416(2)
C12 C13 1.3603(19)
C12 H12 0.9300
C13 O2 1.3718(15)
C14 O2 1.4354(16)
C14 C15 1.461(2)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.179(2)
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
C16 H16 O2 3 0.93 2.48 3.409(2) 177
C3 H3A Cg1 8 0.97 2.95 3.634(2) 129
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
O1 C4 C5 C6 -178.85(12)
C13 C4 C5 C6 0.5(2)
C4 C5 C6 C7 177.07(13)
C4 C5 C6 C11 -1.0(2)
C11 C6 C7 C8 -0.7(2)
C5 C6 C7 C8 -178.81(15)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C10 0.9(3)
C8 C9 C10 C11 -0.2(3)
C9 C10 C11 C12 177.43(15)
C9 C10 C11 C6 -1.0(2)
C7 C6 C11 C10 1.4(2)
C5 C6 C11 C10 179.60(13)
C7 C6 C11 C12 -177.05(13)
C5 C6 C11 C12 1.1(2)
C10 C11 C12 C13 -179.18(14)
C6 C11 C12 C13 -0.7(2)
C11 C12 C13 O2 -179.26(12)
C11 C12 C13 C4 0.2(2)
C5 C4 C13 C12 -0.1(2)
O1 C4 C13 C12 179.33(12)
C5 C4 C13 O2 179.43(12)
O1 C4 C13 O2 -1.12(16)
C5 C4 O1 C3 3.1(2)
C13 C4 O1 C3 -176.35(12)
C2 C3 O1 C4 177.75(12)
C12 C13 O2 C14 -1.0(2)
C4 C13 O2 C14 179.51(11)
C15 C14 O2 C13 -81.84(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741175
