#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222038.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_2222038
loop_
_publ_author_name
'Dong, Wen-Kui'
'Wu, Jian-Chao'
'Sun, Yin-Xia'
'Yao, Jian'
'Tong, Jun-Feng'
_publ_section_title
;
 2,2'-{1,1'-[Butane-1,4-diylbis(oxynitrilo)]diethylidyne}di-1-naphthol
;
_journal_coeditor_code           HG2505
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1248
_journal_paper_doi               10.1107/S160053680901647X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C28 H28 N2 O4'
_chemical_formula_moiety         'C28 H28 N2 O4'
_chemical_formula_sum            'C28 H28 N2 O4'
_chemical_formula_weight         456.52
_chemical_name_systematic
;
2,2'-{1,1'-[Butane-1,4-diylbis(oxynitrilo)]diethylidyne}di-1-naphthol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                105.841(2)
_cell_angle_beta                 105.940(2)
_cell_angle_gamma                91.6890(10)
_cell_formula_units_Z            1
_cell_length_a                   6.9590(15)
_cell_length_b                   8.6598(18)
_cell_length_c                   10.596(2)
_cell_measurement_reflns_used    1246
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.614
_cell_measurement_theta_min      2.461
_cell_volume                     586.9(2)
_computing_cell_refinement       'SAINT (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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3020
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0536
_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)+(0.0960P)²+0.0813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                1350
_reflns_number_total             2026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2505.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2222038
_cod_database_fobs_code          2222038
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4299(3) 0.3289(2) 0.31934(16) 0.0435(5) Uani d . 1 . .
O O1 0.3505(2) 0.37340(18) 0.19981(14) 0.0515(5) Uani d . 1 . .
O O2 0.7182(2) 0.30688(18) 0.52155(15) 0.0505(5) Uani d . 1 . .
H H2 0.6665 0.3326 0.4519 0.076 Uiso calc R 1 . .
C C1 0.5112(3) 0.4251(3) 0.1562(2) 0.0455(6) Uani d . 1 . .
H H1A 0.5966 0.3396 0.1410 0.055 Uiso calc R 1 . .
H H1B 0.5923 0.5189 0.2259 0.055 Uiso calc R 1 . .
C C2 0.4211(3) 0.4667(3) 0.0252(2) 0.0449(6) Uani d . 1 . .
H H2A 0.3277 0.5459 0.0400 0.054 Uiso calc R 1 . .
H H2B 0.3460 0.3705 -0.0449 0.054 Uiso calc R 1 . .
C C3 0.2958(3) 0.2877(2) 0.3702(2) 0.0402(5) Uani d . 1 . .
C C4 0.0759(3) 0.2939(3) 0.3091(2) 0.0627(7) Uani d . 1 . .
H H4A 0.0578 0.3501 0.2408 0.094 Uiso calc R 1 . .
H H4B 0.0198 0.3496 0.3798 0.094 Uiso calc R 1 . .
H H4C 0.0091 0.1859 0.2673 0.094 Uiso calc R 1 . .
C C5 0.5732(3) 0.2467(2) 0.5630(2) 0.0372(5) Uani d . 1 . .
C C6 0.3690(3) 0.2344(2) 0.49419(19) 0.0365(5) Uani d . 1 . .
C C7 0.2306(3) 0.1639(2) 0.5453(2) 0.0433(5) Uani d . 1 . .
H H7 0.0937 0.1554 0.5009 0.052 Uiso calc R 1 . .
C C8 0.2912(3) 0.1088(2) 0.6565(2) 0.0438(6) Uani d . 1 . .
H H8 0.1961 0.0608 0.6851 0.053 Uiso calc R 1 . .
C C9 0.4976(3) 0.1238(2) 0.7294(2) 0.0386(5) Uani d . 1 . .
C C10 0.6397(3) 0.1961(2) 0.6838(2) 0.0370(5) Uani d . 1 . .
C C11 0.8449(3) 0.2185(3) 0.7606(2) 0.0506(6) Uani d . 1 . .
H H11 0.9400 0.2668 0.7321 0.061 Uiso calc R 1 . .
C C12 0.9047(4) 0.1696(3) 0.8761(3) 0.0600(7) Uani d . 1 . .
H H12 1.0397 0.1872 0.9270 0.072 Uiso calc R 1 . .
C C13 0.7640(4) 0.0933(3) 0.9182(2) 0.0564(7) Uani d . 1 . .
H H13 0.8068 0.0574 0.9955 0.068 Uiso calc R 1 . .
C C14 0.5661(3) 0.0711(3) 0.8475(2) 0.0479(6) Uani d . 1 . .
H H14 0.4743 0.0207 0.8770 0.057 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
C3 N1 O1 . . 113.72(17) ?
N1 O1 C1 . . 109.26(15) ?
C5 O2 H2 . . 109.5 ?
O1 C1 C2 . . 107.96(18) ?
O1 C1 H1A . . 110.1 ?
C2 C1 H1A . . 110.1 ?
O1 C1 H1B . . 110.1 ?
C2 C1 H1B . . 110.1 ?
H1A C1 H1B . . 108.4 ?
C1 C2 C2 . 2_665 112.2(2) ?
C1 C2 H2A . . 109.2 ?
C2 C2 H2A 2_665 . 109.2 ?
C1 C2 H2B . . 109.2 ?
C2 C2 H2B 2_665 . 109.2 ?
H2A C2 H2B . . 107.9 ?
N1 C3 C6 . . 116.56(18) ?
N1 C3 C4 . . 122.53(18) ?
C6 C3 C4 . . 120.91(18) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O2 C5 C6 . . 122.92(17) ?
O2 C5 C10 . . 116.22(18) ?
C6 C5 C10 . . 120.86(18) ?
C5 C6 C7 . . 117.71(18) ?
C5 C6 C3 . . 122.01(18) ?
C7 C6 C3 . . 120.26(18) ?
C8 C7 C6 . . 122.4(2) ?
C8 C7 H7 . . 118.8 ?
C6 C7 H7 . . 118.8 ?
C7 C8 C9 . . 120.59(19) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C10 C9 C14 . . 118.88(19) ?
C10 C9 C8 . . 118.87(17) ?
C14 C9 C8 . . 122.24(19) ?
C9 C10 C11 . . 118.88(18) ?
C9 C10 C5 . . 119.50(18) ?
C11 C10 C5 . . 121.61(19) ?
C12 C11 C10 . . 120.5(2) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.4(2) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.6(2) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C9 . . 120.8(2) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 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 C3 . 1.285(3) ?
N1 O1 . 1.398(2) ?
O1 C1 . 1.425(2) ?
O2 C5 . 1.350(2) ?
O2 H2 . 0.8200 ?
C1 C2 . 1.503(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C2 2_665 1.509(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C6 . 1.475(3) ?
C3 C4 . 1.498(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.394(3) ?
C5 C10 . 1.427(3) ?
C6 C7 . 1.423(3) ?
C7 C8 . 1.357(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.415(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.413(3) ?
C9 C14 . 1.414(3) ?
C10 C11 . 1.414(3) ?
C11 C12 . 1.365(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.400(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.354(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 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 2.557(2) 145.0 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
C3 N1 O1 C1 . . . . 176.83(17) ?
N1 O1 C1 C2 . . . . 178.10(15) ?
O1 C1 C2 C2 . . . 2_665 176.3(2) ?
O1 N1 C3 C6 . . . . 178.15(15) ?
O1 N1 C3 C4 . . . . -2.3(3) ?
O2 C5 C6 C7 . . . . 177.98(17) ?
C10 C5 C6 C7 . . . . -2.5(3) ?
O2 C5 C6 C3 . . . . -0.4(3) ?
C10 C5 C6 C3 . . . . 179.16(17) ?
N1 C3 C6 C5 . . . . 7.8(3) ?
C4 C3 C6 C5 . . . . -171.77(19) ?
N1 C3 C6 C7 . . . . -170.53(17) ?
C4 C3 C6 C7 . . . . 9.9(3) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
C3 C6 C7 C8 . . . . 178.04(18) ?
C6 C7 C8 C9 . . . . 1.8(3) ?
C7 C8 C9 C10 . . . . -0.4(3) ?
C7 C8 C9 C14 . . . . 178.56(19) ?
C14 C9 C10 C11 . . . . -2.1(3) ?
C8 C9 C10 C11 . . . . 176.85(18) ?
C14 C9 C10 C5 . . . . 178.64(16) ?
C8 C9 C10 C5 . . . . -2.4(3) ?
O2 C5 C10 C9 . . . . -176.58(16) ?
C6 C5 C10 C9 . . . . 3.8(3) ?
O2 C5 C10 C11 . . . . 4.2(3) ?
C6 C5 C10 C11 . . . . -175.34(18) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C5 C10 C11 C12 . . . . 179.74(19) ?
C10 C11 C12 C13 . . . . 1.5(4) ?
C11 C12 C13 C14 . . . . -2.0(4) ?
C12 C13 C14 C9 . . . . 0.3(3) ?
C10 C9 C14 C13 . . . . 1.7(3) ?
C8 C9 C14 C13 . . . . -177.2(2) ?
