#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/80/2208091.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_2208091
loop_
_publ_author_name
'Yu, Hai-Yan'
'Xue, Jin-Ping'
'Chen, Nai-Sheng'
'Huang, Jin-Ling'
_publ_section_title
;
 4-(Quinolin-4-yloxy)phthalonitrile
;
_journal_coeditor_code           IS6165
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o480
_journal_page_last               o481
_journal_paper_doi               10.1107/S1600536805042893
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H9 N3 O'
_chemical_formula_moiety         'C17 H9 N3 O'
_chemical_formula_sum            'C17 H9 N3 O'
_chemical_formula_weight         271.27
_chemical_melting_point          448.6(4)
_chemical_name_systematic
;
4-(Quinolin-4-yloxy)phthalonitrile
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.1044(5)
_cell_length_b                   15.5318(8)
_cell_length_c                   24.6393(2)
_cell_measurement_reflns_used    11450
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.55
_cell_volume                     2718.8(2)
_computing_cell_refinement       TEXRAY
_computing_data_collection
'TEXRAY (Molecular Structure Corporation, 1999)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2004)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotor target'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025636
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15500
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0414
_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)+(0.0573P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                1821
_reflns_number_total             3047
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6165.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '448.2-449 K' was changed to
'448.6(4)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '448.2-449 K' was changed to
'448.6(4)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208091
_cod_database_fobs_code          2208091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 0.16841(17) 0.43874(8) 0.43363(4) 0.0764(4) Uani d . 1 O
N1 -0.1471(2) 0.31440(10) 0.55325(6) 0.0685(4) Uani d . 1 N
N2 0.1413(3) 0.17152(11) 0.26510(7) 0.0970(6) Uani d . 1 N
N3 0.1379(2) 0.37628(11) 0.16446(6) 0.0868(5) Uani d . 1 N
C1 0.0313(2) 0.34363(10) 0.56280(6) 0.0590(4) Uani d . 1 C
C2 0.1081(3) 0.33231(14) 0.61487(7) 0.0819(6) Uani d . 1 C
H2 0.0369 0.3034 0.6419 0.098 Uiso calc R 1 H
C3 0.2812(3) 0.36192(17) 0.62689(9) 0.1022(8) Uani d . 1 C
H3 0.3301 0.3544 0.6625 0.123 Uiso calc R 1 H
C4 0.3894(3) 0.40345(17) 0.58767(9) 0.1001(7) Uani d . 1 C
H4 0.5111 0.4242 0.5968 0.120 Uiso calc R 1 H
C5 0.3227(3) 0.41475(13) 0.53634(8) 0.0770(5) Uani d . 1 C
H5 0.3985 0.4423 0.5097 0.092 Uiso calc R 1 H
C6 0.1408(2) 0.38546(10) 0.52284(6) 0.0550(4) Uani d . 1 C
C7 0.0597(2) 0.39446(9) 0.47104(6) 0.0555(4) Uani d . 1 C
C8 -0.1164(2) 0.36456(11) 0.46116(6) 0.0629(4) Uani d . 1 C
H8 -0.1723 0.3700 0.4263 0.075 Uiso calc R 1 H
C9 -0.2128(2) 0.32555(11) 0.50396(7) 0.0674(5) Uani d . 1 C
H9 -0.3365 0.3053 0.4968 0.081 Uiso calc R 1 H
C10 0.1516(2) 0.42115(10) 0.37898(6) 0.0573(4) Uani d . 1 C
C11 0.1525(2) 0.49150(11) 0.34465(6) 0.0651(5) Uani d . 1 C
H11 0.1563 0.5482 0.3591 0.078 Uiso calc R 1 H
C12 0.1480(2) 0.47901(10) 0.28949(6) 0.0641(4) Uani d . 1 C
H12 0.1481 0.5272 0.2658 0.077 Uiso calc R 1 H
C13 0.1432(2) 0.39662(10) 0.26827(6) 0.0523(4) Uani d . 1 C
C14 0.1491(2) 0.33802(10) 0.35933(6) 0.0569(4) Uani d . 1 C
H14 0.1506 0.2902 0.3834 0.068 Uiso calc R 1 H
C15 0.1445(2) 0.32601(9) 0.30356(6) 0.0514(4) Uani d . 1 C
C16 0.1437(2) 0.23993(12) 0.28210(6) 0.0657(5) Uani d . 1 C
C17 0.1402(2) 0.38431(11) 0.21025(7) 0.0623(4) Uani d . 1 C
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 0.1022(9) 0.0830(8) 0.0441(6) -0.0301(7) 0.0063(6) -0.0032(6)
N1 0.0749(10) 0.0706(9) 0.0602(9) -0.0024(8) 0.0116(7) 0.0026(7)
N2 0.1400(16) 0.0660(10) 0.0850(12) 0.0099(10) 0.0194(11) -0.0115(9)
N3 0.1006(12) 0.1108(13) 0.0490(8) -0.0053(10) 0.0088(9) 0.0006(9)
C1 0.0688(10) 0.0615(9) 0.0467(8) 0.0106(8) 0.0058(8) -0.0004(7)
C2 0.0880(14) 0.1058(15) 0.0520(10) 0.0224(12) 0.0033(10) 0.0124(10)
C3 0.0941(16) 0.155(2) 0.0573(11) 0.0318(15) -0.0120(12) 0.0022(13)
C4 0.0731(13) 0.151(2) 0.0766(14) 0.0041(13) -0.0195(12) -0.0208(14)
C5 0.0678(11) 0.0959(14) 0.0675(11) -0.0072(10) -0.0007(9) -0.0115(10)
C6 0.0613(9) 0.0560(8) 0.0476(8) 0.0041(7) 0.0018(7) -0.0081(7)
C7 0.0725(10) 0.0521(8) 0.0421(8) -0.0036(7) 0.0078(8) -0.0027(7)
C8 0.0714(11) 0.0705(10) 0.0467(8) -0.0026(8) -0.0044(8) -0.0069(8)
C9 0.0661(10) 0.0722(11) 0.0640(11) -0.0054(8) 0.0052(9) -0.0111(9)
C10 0.0646(9) 0.0673(10) 0.0400(8) -0.0058(8) 0.0041(7) -0.0010(7)
C11 0.0840(12) 0.0556(9) 0.0557(10) -0.0015(8) 0.0046(9) -0.0020(7)
C12 0.0802(11) 0.0577(9) 0.0544(9) -0.0002(8) 0.0022(8) 0.0093(7)
C13 0.0506(8) 0.0621(9) 0.0442(7) 0.0015(7) 0.0039(7) 0.0048(6)
C14 0.0671(10) 0.0564(9) 0.0471(8) 0.0007(7) 0.0038(7) 0.0064(7)
C15 0.0524(8) 0.0552(8) 0.0465(8) 0.0037(7) 0.0066(7) 0.0008(7)
C16 0.0787(11) 0.0638(10) 0.0545(10) 0.0077(9) 0.0121(8) 0.0012(8)
C17 0.0648(10) 0.0741(11) 0.0478(9) -0.0018(8) 0.0072(8) 0.0063(8)
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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C10 O1 C7 120.20(12) yes
C9 N1 C1 116.44(15) yes
N1 C1 C2 118.41(17) no
N1 C1 C6 122.91(15) no
C2 C1 C6 118.68(17) ?
C3 C2 C1 120.86(19) ?
C3 C2 H2 119.6 no
C1 C2 H2 119.6 no
C2 C3 C4 120.63(19) ?
C2 C3 H3 119.7 no
C4 C3 H3 119.7 no
C5 C4 C3 120.8(2) ?
C5 C4 H4 119.6 no
C3 C4 H4 119.6 no
C4 C5 C6 119.75(19) ?
C4 C5 H5 120.1 no
C6 C5 H5 120.1 no
C7 C6 C5 123.85(15) ?
C7 C6 C1 116.90(15) ?
C5 C6 C1 119.24(15) ?
C8 C7 O1 124.38(14) yes
C8 C7 C6 120.41(15) ?
O1 C7 C6 115.14(14) no
C7 C8 C9 117.75(15) ?
C7 C8 H8 121.1 no
C9 C8 H8 121.1 no
N1 C9 C8 125.59(16) no
N1 C9 H9 117.2 no
C8 C9 H9 117.2 no
O1 C10 C14 121.96(14) yes
O1 C10 C11 116.14(14) no
C14 C10 C11 121.70(14) ?
C12 C11 C10 119.60(15) ?
C12 C11 H11 120.2 no
C10 C11 H11 120.2 no
C11 C12 C13 120.36(14) ?
C11 C12 H12 119.8 no
C13 C12 H12 119.8 no
C12 C13 C15 119.36(14) ?
C12 C13 C17 119.85(14) ?
C15 C13 C17 120.79(14) ?
C10 C14 C15 118.30(14) ?
C10 C14 H14 120.9 no
C15 C14 H14 120.9 no
C14 C15 C13 120.67(13) ?
C14 C15 C16 119.31(13) ?
C13 C15 C16 120.01(13) ?
N2 C16 C15 179.38(19) ?
N3 C17 C13 178.69(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.3790(18) yes
O1 C7 1.3852(18) yes
N1 C9 1.313(2) yes
N1 C1 1.367(2) yes
N2 C16 1.142(2) yes
N3 C17 1.135(2) yes
C1 C2 1.405(2) ?
C1 C6 1.413(2) ?
C2 C3 1.346(3) ?
C2 H2 0.9500 no
C3 C4 1.393(3) ?
C3 H3 0.9500 no
C4 C5 1.362(3) ?
C4 H4 0.9500 no
C5 C6 1.410(2) ?
C5 H5 0.9500 no
C6 C7 1.407(2) ?
C7 C8 1.357(2) ?
C8 C9 1.396(2) ?
C8 H8 0.9500 no
C9 H9 0.9500 no
C10 C14 1.379(2) ?
C10 C11 1.382(2) ?
C11 C12 1.373(2) ?
C11 H11 0.9500 no
C12 C13 1.383(2) ?
C12 H12 0.9500 no
C13 C15 1.400(2) ?
C13 C17 1.443(2) ?
C14 C15 1.3872(19) ?
C14 H14 0.9500 no
C15 C16 1.438(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126533
