#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/97/2219763.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_2219763
loop_
_publ_author_name
'Yao, Li'
'Tao, Ruo-Jie'
_publ_section_title
;
 2,6-Bis(prop-2-ynyloxy)naphthalene
;
_journal_coeditor_code           BG2213
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2081
_journal_paper_doi               10.1107/S1600536808031772
_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
;
2,6-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            4
_cell_length_a                   7.5783(11)
_cell_length_b                   8.0295(12)
_cell_length_c                   20.972(3)
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.229
_cell_measurement_theta_min      2.6875
_cell_volume                     1276.1(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6824
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0388
_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)+(0.0447P)²+0.1717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                952
_reflns_number_total             1250
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2213.cif
_cod_data_source_block           I
_cod_database_code               2219763
_cod_database_fobs_code          2219763
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
O O1 0.99206(12) 0.82529(11) 0.13702(4) 0.0551(3) Uani d . 1
C C1 0.9300(3) 1.1886(2) 0.21293(9) 0.0939(7) Uani d . 1
H H1 0.9416 1.2665 0.2455 0.113 Uiso calc R 1
C C2 0.9155(2) 1.09120(19) 0.17226(8) 0.0662(5) Uani d . 1
C C3 0.8995(2) 0.97311(17) 0.12002(7) 0.0600(4) Uani d . 1
H H3A 0.7762 0.9479 0.1123 0.072 Uiso calc R 1
H H3B 0.9492 1.0202 0.0814 0.072 Uiso calc R 1
C C4 1.00020(16) 0.70096(16) 0.09247(7) 0.0473(3) Uani d . 1
C C5 1.09064(17) 0.55721(17) 0.11300(7) 0.0532(4) Uani d . 1
H H5 1.1365 0.5528 0.1541 0.064 Uiso calc R 1
C C6 1.11120(18) 0.42548(16) 0.07337(7) 0.0525(4) Uani d . 1
H H6 1.1699 0.3313 0.0881 0.063 Uiso calc R 1
C C7 1.04565(15) 0.42735(15) 0.01009(7) 0.0458(3) Uani d . 1
C C8 0.93214(16) 0.70846(16) 0.03204(6) 0.0481(4) Uani d . 1
H H8 0.8713 0.8029 0.0187 0.058 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0576(6) 0.0521(6) 0.0555(6) 0.0050(5) -0.0035(5) 0.0030(5)
C1 0.145(2) 0.0720(11) 0.0651(12) 0.0012(12) 0.0035(12) -0.0069(10)
C2 0.0822(11) 0.0563(9) 0.0601(10) 0.0052(8) 0.0045(8) 0.0045(8)
C3 0.0666(10) 0.0526(8) 0.0609(9) 0.0060(7) -0.0028(7) 0.0032(7)
C4 0.0400(7) 0.0467(7) 0.0553(8) -0.0026(6) 0.0014(6) 0.0045(6)
C5 0.0497(8) 0.0572(8) 0.0525(8) 0.0020(7) -0.0072(6) 0.0088(7)
C6 0.0476(7) 0.0494(7) 0.0603(9) 0.0081(6) -0.0066(6) 0.0109(7)
C7 0.0364(6) 0.0465(7) 0.0546(8) -0.0008(5) -0.0014(6) 0.0103(6)
C8 0.0424(7) 0.0446(7) 0.0575(9) 0.0042(6) -0.0021(6) 0.0095(6)
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_1
_geom_angle_site_symmetry_3
_geom_angle
C4 O1 C3 . . 117.34(10)
C2 C1 H1 . . 180.0
C1 C2 C3 . . 178.25(18)
O1 C3 C2 . . 108.28(12)
O1 C3 H3A . . 110.0
C2 C3 H3A . . 110.0
O1 C3 H3B . . 110.0
C2 C3 H3B . . 110.0
H3A C3 H3B . . 108.4
O1 C4 C8 . . 125.63(12)
O1 C4 C5 . . 114.25(12)
C8 C4 C5 . . 120.11(13)
C6 C5 C4 . . 120.54(13)
C6 C5 H5 . . 119.7
C4 C5 H5 . . 119.7
C5 C6 C7 . . 121.74(12)
C5 C6 H6 . . 119.1
C7 C6 H6 . . 119.1
C8 C7 C6 5_765 . 122.38(12)
C8 C7 C7 5_765 5_765 120.34(15)
C6 C7 C7 . 5_765 117.28(16)
C4 C8 C7 . 5_765 119.98(12)
C4 C8 H8 . . 120.0
C7 C8 H8 5_765 . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C4 . 1.3687(16)
O1 C3 . 1.4240(16)
C1 C2 . 1.162(2)
C1 H1 . 0.9300
C2 C3 . 1.454(2)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 C8 . 1.3695(19)
C4 C5 . 1.4098(18)
C5 C6 . 1.3541(18)
C5 H5 . 0.9300
C6 C7 . 1.417(2)
C6 H6 . 0.9300
C7 C8 5_765 1.4136(18)
C7 C7 5_765 1.421(2)
C8 C7 5_765 1.4136(18)
C8 H8 . 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
C1 H1 O1 3_755 0.93 2.56 3.385(2) 148.1
C3 H3A Cg1 8_655 0.97 2.759 3.579(2) 142.66
C3 H3A Cg2 4_465 0.97 2.759 3.579(2) 142.66
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_4
_geom_torsion
C4 O1 C3 C2 . -176.80(12)
C3 O1 C4 C8 . 2.36(19)
C3 O1 C4 C5 . -178.77(11)
O1 C4 C5 C6 . -178.91(12)
C8 C4 C5 C6 . 0.02(19)
C4 C5 C6 C7 . 0.9(2)
C5 C6 C7 C8 5_765 179.27(12)
C5 C6 C7 C7 5_765 -1.0(2)
O1 C4 C8 C7 5_765 178.05(12)
C5 C4 C8 C7 5_765 -0.75(19)
