#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/60/7106034.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_7106034
loop_
_publ_author_name
'Xiaopeng Chen'
'Hongbo Wang'
'Xiaohan Jin'
'Jinwu Feng'
'Yanguang Wang'
'Ping Lu'
_publ_section_title
;
 Palladium catalyzed bicyclization of 1,8-diiodonaphthalene and tertiary
 propargylic alcohols to phenalenones and their applications as
 fluorescent chemosensor for fluoride ions
;
_journal_name_full               Chem.Commun.
_journal_page_first              2628
_journal_paper_doi               10.1039/c0cc04875e
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C17 H12 O4 '
_chemical_formula_sum            'C17 H12 O4'
_chemical_formula_weight         280.28
_chemical_melting_point          507.1(12)
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_audit_creation_date             2008-06-26
_audit_creation_method           'by CrystalStructure 3.7.0'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   19.8142(12)
_cell_length_b                   6.9536(4)
_cell_length_c                   19.0019(12)
_cell_measurement_reflns_used    15045
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     2618.1(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.139
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            39855
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3225
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0001Fo² + 0.2380σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                1351
_reflns_number_total             3225
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            C0CC04875E.TXT
_cod_data_source_block           General
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '505.95-508.35' was changed to
'507.1(12)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_formula_sum        'C17 H12 O4 '
_cod_database_code               7106034
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2+Z
3 +X,1/2-Y,+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,1/2-Z
7 -X,1/2+Y,-Z
8 1/2+X,+Y,1/2-Z
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
O11 O 0.52167(12) 0.2500 0.45184(12) 0.0677(10) Uani 1.00 2 d S . .
O12 O 0.44660(12) 0.2500 0.36593(13) 0.0761(10) Uani 1.00 2 d S . .
O13 O 0.45700(12) 0.250000(10) 0.23147(13) 0.0727(10) Uani 1.00 2 d S . .
O14 O 0.73690(12) 0.2500 0.40591(12) 0.0713(9) Uani 1.00 2 d S . .
O21 O 0.37094(12) 0.7500 0.20509(16) 0.0744(10) Uani 1.00 2 d S . .
O22 O 0.41213(12) 0.7500 0.31352(14) 0.0893(11) Uani 1.00 2 d S . .
O23 O 0.53371(12) 0.750000(10) 0.36208(12) 0.0783(10) Uani 1.00 2 d S . .
O24 O 0.50425(14) 0.7500 0.02268(12) 0.0870(11) Uani 1.00 2 d S . .
C1 C 0.5058(2) 0.2500 0.3837(2) 0.0590(14) Uani 1.00 2 d S . .
C2 C 0.56749(18) 0.2500 0.34024(19) 0.0459(12) Uani 1.00 2 d S . .
C3 C 0.57479(18) 0.2500 0.26485(19) 0.0429(12) Uani 1.00 2 d S . .
C4 C 0.5229(2) 0.2500 0.2160(2) 0.0534(13) Uani 1.00 2 d S . .
C5 C 0.5369(2) 0.250000(10) 0.1433(2) 0.0598(15) Uani 1.00 2 d S . .
C6 C 0.6010(2) 0.250000(10) 0.1197(2) 0.0613(14) Uani 1.00 2 d S . .
C7 C 0.6562(2) 0.2500 0.1665(2) 0.0530(13) Uani 1.00 2 d S . .
C8 C 0.7229(2) 0.250000(10) 0.1419(2) 0.0695(15) Uani 1.00 2 d S . .
C9 C 0.7766(2) 0.250000(10) 0.1883(2) 0.0747(16) Uani 1.00 2 d S . .
C10 C 0.7648(2) 0.250000(10) 0.2597(2) 0.0613(14) Uani 1.00 2 d S . .
C11 C 0.69943(19) 0.2500 0.28655(19) 0.0475(12) Uani 1.00 2 d S . .
C12 C 0.64335(19) 0.2500 0.23987(18) 0.0450(12) Uani 1.00 2 d S . .
C13 C 0.68960(18) 0.2500 0.3630(2) 0.0525(13) Uani 1.00 2 d S . .
C14 C 0.61983(18) 0.2500 0.38582(18) 0.0443(11) Uani 1.00 2 d S . .
C15 C 0.59590(19) 0.2500 0.46099(19) 0.0550(14) Uani 1.00 2 d S . .
C16 C 0.61414(12) 0.4327(3) 0.50054(12) 0.0715(9) Uani 1.00 1 d . . .
C21 C 0.4224(2) 0.7500 0.2499(2) 0.0645(15) Uani 1.00 2 d S . .
C22 C 0.48723(19) 0.7500 0.2110(2) 0.0490(12) Uani 1.00 2 d S . .
C23 C 0.55605(19) 0.7500 0.23640(19) 0.0441(12) Uani 1.00 2 d S . .
C24 C 0.5762(2) 0.7500 0.3053(2) 0.0591(14) Uani 1.00 2 d S . .
C25 C 0.6445(2) 0.750000(10) 0.3243(2) 0.0642(15) Uani 1.00 2 d S . .
C26 C 0.6928(2) 0.750000(10) 0.2741(2) 0.0634(15) Uani 1.00 2 d S . .
C27 C 0.6761(2) 0.7500 0.2020(2) 0.0568(14) Uani 1.00 2 d S . .
C28 C 0.7266(2) 0.750000(10) 0.1506(2) 0.0728(16) Uani 1.00 2 d S . .
C29 C 0.7089(2) 0.750000(10) 0.0802(2) 0.0762(17) Uani 1.00 2 d S . .
C30 C 0.6421(2) 0.750000(10) 0.0612(2) 0.0645(14) Uani 1.00 2 d S . .
C31 C 0.5905(2) 0.7500 0.1100(2) 0.0528(13) Uani 1.00 2 d S . .
C32 C 0.60650(19) 0.7500 0.1826(2) 0.0473(12) Uani 1.00 2 d S . .
C33 C 0.5202(2) 0.7500 0.0858(2) 0.0598(14) Uani 1.00 2 d S . .
C34 C 0.47036(18) 0.7500 0.1422(2) 0.0495(13) Uani 1.00 2 d S . .
C35 C 0.3959(2) 0.7500 0.1308(2) 0.0608(14) Uani 1.00 2 d S . .
C36 C 0.36982(12) 0.5687(3) 0.09652(13) 0.0814(10) Uani 1.00 1 d . . .
H5 H 0.5014 0.2500 0.1112 0.072 Uiso 1.00 2 c R . .
H6 H 0.6090 0.2500 0.0714 0.074 Uiso 1.00 2 c R . .
H8 H 0.7312 0.2500 0.0937 0.083 Uiso 1.00 2 c R . .
H9 H 0.8206 0.2500 0.1713 0.090 Uiso 1.00 2 c R . .
H10 H 0.8012 0.2500 0.2906 0.074 Uiso 1.00 2 c R . .
H25 H 0.6567 0.7500 0.3715 0.077 Uiso 1.00 2 c R . .
H26 H 0.7380 0.7500 0.2874 0.076 Uiso 1.00 2 c R . .
H28 H 0.7718 0.7500 0.1637 0.087 Uiso 1.00 2 c R . .
H29 H 0.7422 0.7500 0.0458 0.091 Uiso 1.00 2 c R . .
H30 H 0.6311 0.7500 0.0136 0.077 Uiso 1.00 2 c R . .
H130 H 0.4503 0.2500 0.2814 0.087 Uiso 1.00 2 c R . .
H161 H 0.5921 0.5405 0.4789 0.086 Uiso 1.00 1 c R . .
H162 H 0.6621 0.4511 0.4991 0.086 Uiso 1.00 1 c R . .
H163 H 0.5997 0.4218 0.5486 0.086 Uiso 1.00 1 c R . .
H230 H 0.4887 0.7500 0.3446 0.094 Uiso 1.00 2 c R . .
H361 H 0.3847 0.4589 0.1229 0.098 Uiso 1.00 1 c R . .
H362 H 0.3214 0.5715 0.0956 0.098 Uiso 1.00 1 c R . .
H363 H 0.3868 0.5604 0.0493 0.098 Uiso 1.00 1 c R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 O11 C15 110.4(2) ? . . .
C21 O21 C35 110.5(3) ? . . .
O11 C1 O12 119.7(3) ? . . .
O11 C1 C2 110.4(3) ? . . .
O12 C1 C2 129.9(3) ? . . .
C1 C2 C3 129.8(3) ? . . .
C1 C2 C14 106.1(3) ? . . .
C3 C2 C14 124.1(3) ? . . .
C2 C3 C4 126.3(3) ? . . .
C2 C3 C12 115.0(3) ? . . .
C4 C3 C12 118.7(3) ? . . .
O13 C4 C3 125.2(3) ? . . .
O13 C4 C5 114.0(3) ? . . .
C3 C4 C5 120.7(3) ? . . .
C4 C5 C6 120.8(3) ? . . .
C5 C6 C7 121.4(3) ? . . .
C6 C7 C8 121.4(3) ? . . .
C6 C7 C12 118.8(3) ? . . .
C8 C7 C12 119.9(3) ? . . .
C7 C8 C9 120.9(3) ? . . .
C8 C9 C10 119.9(3) ? . . .
C9 C10 C11 121.3(3) ? . . .
C10 C11 C12 119.9(3) ? . . .
C10 C11 C13 119.1(3) ? . . .
C12 C11 C13 121.0(3) ? . . .
C3 C12 C7 119.6(3) ? . . .
C3 C12 C11 122.1(3) ? . . .
C7 C12 C11 118.2(3) ? . . .
O14 C13 C11 123.4(3) ? . . .
O14 C13 C14 121.6(3) ? . . .
C11 C13 C14 115.0(3) ? . . .
C2 C14 C13 122.8(3) ? . . .
C2 C14 C15 111.5(3) ? . . .
C13 C14 C15 125.7(3) ? . . .
O11 C15 C14 101.6(2) ? . . .
O11 C15 C16 107.11(19) ? . . .
O11 C15 C16 107.11(19) ? . . 3_555
C14 C15 C16 113.23(18) ? . . .
C14 C15 C16 113.23(18) ? . . 3_555
C16 C15 C16 113.4(2) ? . . 3_555
O21 C21 O22 120.3(3) ? . . .
O21 C21 C22 110.2(3) ? . . .
O22 C21 C22 129.5(3) ? . . .
C21 C22 C23 130.6(3) ? . . .
C21 C22 C34 105.6(3) ? . . .
C23 C22 C34 123.9(3) ? . . .
C22 C23 C24 126.5(3) ? . . .
C22 C23 C32 114.8(3) ? . . .
C24 C23 C32 118.7(3) ? . . .
O23 C24 C23 125.1(3) ? . . .
O23 C24 C25 113.0(3) ? . . .
C23 C24 C25 121.9(3) ? . . .
C24 C25 C26 120.2(3) ? . . .
C25 C26 C27 121.3(3) ? . . .
C26 C27 C28 120.7(3) ? . . .
C26 C27 C32 118.5(3) ? . . .
C28 C27 C32 120.8(4) ? . . .
C27 C28 C29 119.5(3) ? . . .
C28 C29 C30 120.0(4) ? . . .
C29 C30 C31 122.5(3) ? . . .
C30 C31 C32 119.3(3) ? . . .
C30 C31 C33 119.5(3) ? . . .
C32 C31 C33 121.2(3) ? . . .
C23 C32 C27 119.4(3) ? . . .
C23 C32 C31 122.7(3) ? . . .
C27 C32 C31 117.9(3) ? . . .
O24 C33 C31 123.0(3) ? . . .
O24 C33 C34 122.6(3) ? . . .
C31 C33 C34 114.4(3) ? . . .
C22 C34 C33 123.0(3) ? . . .
C22 C34 C35 112.7(3) ? . . .
C33 C34 C35 124.4(3) ? . . .
O21 C35 C34 101.0(2) ? . . .
O21 C35 C36 107.1(2) ? . . .
O21 C35 C36 107.1(2) ? . . 3_565
C34 C35 C36 113.64(19) ? . . .
C34 C35 C36 113.64(19) ? . . 3_565
C36 C35 C36 113.2(2) ? . . 3_565
C4 O13 H130 110.6 ? . . .
C24 O23 H230 107.5 ? . . .
C4 C5 H5 119.6 ? . . .
C6 C5 H5 119.6 ? . . .
C5 C6 H6 119.3 ? . . .
C7 C6 H6 119.3 ? . . .
C7 C8 H8 119.6 ? . . .
C9 C8 H8 119.6 ? . . .
C8 C9 H9 120.1 ? . . .
C10 C9 H9 120.1 ? . . .
C9 C10 H10 119.4 ? . . .
C11 C10 H10 119.4 ? . . .
C15 C16 H161 109.5 ? . . .
C15 C16 H162 109.5 ? . . .
C15 C16 H163 109.5 ? . . .
H161 C16 H162 109.5 ? . . .
H161 C16 H163 109.5 ? . . .
H162 C16 H163 109.5 ? . . .
C24 C25 H25 119.9 ? . . .
C26 C25 H25 119.9 ? . . .
C25 C26 H26 119.3 ? . . .
C27 C26 H26 119.3 ? . . .
C27 C28 H28 120.2 ? . . .
C29 C28 H28 120.2 ? . . .
C28 C29 H29 120.0 ? . . .
C30 C29 H29 120.0 ? . . .
C29 C30 H30 118.8 ? . . .
C31 C30 H30 118.8 ? . . .
C35 C36 H361 109.5 ? . . .
C35 C36 H362 109.5 ? . . .
C35 C36 H363 109.5 ? . . .
H361 C36 H362 109.5 ? . . .
H361 C36 H363 109.5 ? . . .
H362 C36 H363 109.5 ? . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O11 C1 1.333(4) ? . .
O11 C15 1.481(4) ? . .
O12 C1 1.220(5) ? . .
O13 C4 1.338(4) ? . .
O14 C13 1.242(4) ? . .
O21 C21 1.328(5) ? . .
O21 C35 1.495(4) ? . .
O22 C21 1.227(5) ? . .
O23 C24 1.369(4) ? . .
O24 C33 1.240(5) ? . .
C1 C2 1.475(5) ? . .
C2 C3 1.440(5) ? . .
C2 C14 1.351(5) ? . .
C3 C4 1.386(5) ? . .
C3 C12 1.439(5) ? . .
C4 C5 1.409(5) ? . .
C5 C6 1.348(5) ? . .
C6 C7 1.411(5) ? . .
C7 C8 1.402(5) ? . .
C7 C12 1.417(5) ? . .
C8 C9 1.381(6) ? . .
C9 C10 1.377(6) ? . .
C10 C11 1.392(5) ? . .
C11 C12 1.422(5) ? . .
C11 C13 1.467(5) ? . .
C13 C14 1.449(5) ? . .
C14 C15 1.505(4) ? . .
C15 C16 1.519(3) ? . .
C15 C16 1.519(3) ? . 3_555
C21 C22 1.482(5) ? . .
C22 C23 1.447(5) ? . .
C22 C34 1.349(5) ? . .
C23 C24 1.368(5) ? . .
C23 C32 1.430(5) ? . .
C24 C25 1.402(6) ? . .
C25 C26 1.350(6) ? . .
C26 C27 1.410(6) ? . .
C27 C28 1.397(6) ? . .
C27 C32 1.427(5) ? . .
C28 C29 1.384(6) ? . .
C29 C30 1.372(6) ? . .
C30 C31 1.380(5) ? . .
C31 C32 1.416(5) ? . .
C31 C33 1.467(5) ? . .
C33 C34 1.457(5) ? . .
C34 C35 1.491(5) ? . .
C35 C36 1.511(3) ? . .
C35 C36 1.511(3) ? . 3_565
O13 H130 0.958 ? . .
O23 H230 0.951 ? . .
C5 H5 0.930 ? . .
C6 H6 0.930 ? . .
C8 H8 0.930 ? . .
C9 H9 0.930 ? . .
C10 H10 0.930 ? . .
C16 H161 0.960 ? . .
C16 H162 0.960 ? . .
C16 H163 0.960 ? . .
C25 H25 0.930 ? . .
C26 H26 0.930 ? . .
C28 H28 0.930 ? . .
C29 H29 0.930 ? . .
C30 H30 0.930 ? . .
C36 H361 0.960 ? . .
C36 H362 0.960 ? . .
C36 H363 0.960 ? . .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O(13) H(130) O(12) . . . 2.563(3) 0.958 1.607 174.7 no
O(23) H(230) O(22) . . . 2.580(3) 0.951 1.629 179.1 no
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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 O11 C15 C16 118.99(18) ? . . . .
C1 O11 C15 C16 -118.99(18) ? . . . 3_555
C21 O21 C35 C36 119.2(2) ? . . . .
C21 O21 C35 C36 -119.2(2) ? . . . 3_565
C2 C14 C15 C16 -114.5(2) ? . . . .
C2 C14 C15 C16 114.5(2) ? . . . 3_555
C13 C14 C15 C16 65.5(2) ? . . . .
C13 C14 C15 C16 -65.5(2) ? . . . 3_555
C22 C34 C35 C36 -114.3(2) ? . . . .
C22 C34 C35 C36 114.3(2) ? . . . 3_565
C33 C34 C35 C36 65.7(2) ? . . . .
C33 C34 C35 C36 -65.7(2) ? . . . 3_565
