#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222341.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_2222341
loop_
_publ_author_name
'Dong, Wen-Kui'
'Wu, Jian-chao'
'Yao, Jian'
'Li, Li'
'Gong, Shang-sheng'
_publ_section_title
;
 2,2'-[1,1'-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphthol
;
_journal_coeditor_code           HG2524
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1598
_journal_paper_doi               10.1107/S1600536809022508
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C26 H24 N2 O4'
_chemical_formula_moiety         'C26 H24 N2 O4'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47
_chemical_name_systematic
;
2,2'-[1,1'-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphthol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.478(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6682(18)
_cell_length_b                   9.3728(15)
_cell_length_c                   18.335(2)
_cell_measurement_reflns_used    1610
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.697
_cell_measurement_theta_min      2.241
_cell_volume                     2158.5(5)
_computing_cell_refinement       'SMART (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5220
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block-shaped
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0445
_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)+(0.037P)²+1.5505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                1027
_reflns_number_total             1894
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2524.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        2158.6(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222341
_cod_database_fobs_code          2222341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
N N1 0.97510(17) 0.0879(2) 0.61829(11) 0.0528(6) Uani d . 1 . .
O O1 1.04967(14) 0.11327(19) 0.68140(9) 0.0610(5) Uani d . 1 . .
O O2 0.84279(14) -0.06506(17) 0.53429(9) 0.0620(6) Uani d . 1 . .
H H2 0.8831 -0.0456 0.5717 0.093 Uiso calc R 1 . .
C C1 1.0479(2) -0.0049(3) 0.73030(14) 0.0567(7) Uani d . 1 . .
H H1A 1.1113 -0.0024 0.7661 0.068 Uiso calc R 1 . .
H H1B 1.0493 -0.0929 0.7025 0.068 Uiso calc R 1 . .
C C2 0.9707(2) 0.1902(3) 0.57048(14) 0.0500(7) Uani d . 1 . .
C C3 1.0376(2) 0.3226(3) 0.58230(16) 0.0714(9) Uani d . 1 . .
H H3A 1.0938 0.3072 0.6220 0.107 Uiso calc R 1 . .
H H3B 0.9941 0.4009 0.5942 0.107 Uiso calc R 1 . .
H H3C 1.0678 0.3444 0.5382 0.107 Uiso calc R 1 . .
C C4 0.83740(19) 0.0469(3) 0.48738(13) 0.0464(6) Uani d . 1 . .
C C5 0.89572(19) 0.1710(2) 0.50274(12) 0.0469(6) Uani d . 1 . .
C C6 0.8818(2) 0.2819(3) 0.44918(15) 0.0610(8) Uani d . 1 . .
H H6 0.9202 0.3660 0.4582 0.073 Uiso calc R 1 . .
C C7 0.8146(2) 0.2692(3) 0.38547(16) 0.0676(8) Uani d . 1 . .
H H7 0.8065 0.3454 0.3527 0.081 Uiso calc R 1 . .
C C8 0.7568(2) 0.1424(3) 0.36816(14) 0.0552(7) Uani d . 1 . .
C C9 0.7676(2) 0.0289(3) 0.42035(13) 0.0490(7) Uani d . 1 . .
C C10 0.7106(2) -0.0991(3) 0.40331(15) 0.0632(8) Uani d . 1 . .
H H10 0.7163 -0.1737 0.4370 0.076 Uiso calc R 1 . .
C C11 0.6470(2) -0.1137(4) 0.33734(18) 0.0774(9) Uani d . 1 . .
H H11 0.6097 -0.1982 0.3266 0.093 Uiso calc R 1 . .
C C12 0.6378(2) -0.0025(4) 0.28598(17) 0.0794(10) Uani d . 1 . .
H H12 0.5957 -0.0146 0.2409 0.095 Uiso calc R 1 . .
C C13 0.6896(2) 0.1227(4) 0.30122(15) 0.0707(9) Uani d . 1 . .
H H13 0.6807 0.1966 0.2671 0.085 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 O1 . . 113.2(2) ?
N1 O1 C1 . . 108.64(18) ?
C4 O2 H2 . . 109.5 ?
O1 C1 C1 . 2_756 112.64(18) ?
O1 C1 H1A . . 109.1 ?
C1 C1 H1A 2_756 . 109.1 ?
O1 C1 H1B . . 109.1 ?
C1 C1 H1B 2_756 . 109.1 ?
H1A C1 H1B . . 107.8 ?
N1 C2 C5 . . 116.6(2) ?
N1 C2 C3 . . 122.7(2) ?
C5 C2 C3 . . 120.8(2) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O2 C4 C5 . . 122.7(2) ?
O2 C4 C9 . . 115.4(2) ?
C5 C4 C9 . . 121.9(2) ?
C4 C5 C6 . . 117.2(2) ?
C4 C5 C2 . . 122.8(2) ?
C6 C5 C2 . . 120.1(2) ?
C7 C6 C5 . . 122.5(3) ?
C7 C6 H6 . . 118.8 ?
C5 C6 H6 . . 118.8 ?
C6 C7 C8 . . 121.1(3) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C7 C8 C13 . . 122.9(3) ?
C7 C8 C9 . . 118.4(2) ?
C13 C8 C9 . . 118.7(3) ?
C10 C9 C8 . . 118.9(2) ?
C10 C9 C4 . . 122.1(2) ?
C8 C9 C4 . . 118.9(2) ?
C11 C10 C9 . . 120.3(3) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.5(3) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 120.7(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.9(3) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.295(3) ?
N1 O1 . 1.415(2) ?
O1 C1 . 1.427(3) ?
O2 C4 . 1.353(3) ?
O2 H2 . 0.8200 ?
C1 C1 2_756 1.490(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C5 . 1.473(3) ?
C2 C3 . 1.504(3) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.387(3) ?
C4 C9 . 1.428(3) ?
C5 C6 . 1.425(3) ?
C6 C7 . 1.358(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.410(4) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.412(4) ?
C8 C9 . 1.426(3) ?
C9 C10 . 1.413(3) ?
C10 C11 . 1.370(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.400(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.355(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 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
_geom_hbond_publ_flag
O2 H2 N1 . 0.82 1.84 2.562(3) 145.7 y
C10 H10 O2 7_646 0.93 2.63 3.446(3) 146.3 y
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 O1 C1 . . . . 179.8(2) ?
N1 O1 C1 C1 . . . 2_756 -75.0(3) ?
O1 N1 C2 C5 . . . . 179.31(19) ?
O1 N1 C2 C3 . . . . -0.8(3) ?
O2 C4 C5 C6 . . . . -179.2(2) ?
C9 C4 C5 C6 . . . . 1.1(3) ?
O2 C4 C5 C2 . . . . 1.7(4) ?
C9 C4 C5 C2 . . . . -178.1(2) ?
N1 C2 C5 C4 . . . . -4.3(3) ?
C3 C2 C5 C4 . . . . 175.8(2) ?
N1 C2 C5 C6 . . . . 176.6(2) ?
C3 C2 C5 C6 . . . . -3.3(4) ?
C4 C5 C6 C7 . . . . 0.2(4) ?
C2 C5 C6 C7 . . . . 179.3(2) ?
C5 C6 C7 C8 . . . . -1.8(4) ?
C6 C7 C8 C13 . . . . -177.2(3) ?
C6 C7 C8 C9 . . . . 2.2(4) ?
C7 C8 C9 C10 . . . . -179.5(2) ?
C13 C8 C9 C10 . . . . -0.1(4) ?
C7 C8 C9 C4 . . . . -0.9(3) ?
C13 C8 C9 C4 . . . . 178.5(2) ?
O2 C4 C9 C10 . . . . -1.9(3) ?
C5 C4 C9 C10 . . . . 177.9(2) ?
O2 C4 C9 C8 . . . . 179.6(2) ?
C5 C4 C9 C8 . . . . -0.7(3) ?
C8 C9 C10 C11 . . . . 0.6(4) ?
C4 C9 C10 C11 . . . . -177.9(2) ?
C9 C10 C11 C12 . . . . 0.1(4) ?
C10 C11 C12 C13 . . . . -1.5(5) ?
C11 C12 C13 C8 . . . . 2.1(5) ?
C7 C8 C13 C12 . . . . 178.1(3) ?
C9 C8 C13 C12 . . . . -1.3(4) ?
