#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:17:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178464 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/85/4028586.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_4028586
loop_
_publ_author_name
'Hirohiko Houjou'
'Hajime Shingai'
'Keisuke Yagi'
'Isao Yoshikawa'
'Koji Araki'
_publ_section_title
;
 Mutual Interference between Intramolecular Proton Transfer Sites through
 the Adjoining π-Conjugated System in Schiff Bases of Double-Headed,
 Fused Salicylaldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9021
_journal_page_last               9031
_journal_paper_doi               10.1021/jo401108z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C22 H30 N2 O2'
_chemical_formula_sum            'C22 H30 N2 O2'
_chemical_formula_weight         354.48
_chemical_name_common
1,5-bis(pentyliminomethyl)-2,6-dihydroxynaphthalene
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.376(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.638(1)
_cell_length_b                   11.502(1)
_cell_length_c                   9.890(1)
_cell_measurement_reflns_used    9088
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      72.97
_cell_measurement_theta_min      5.97
_cell_volume                     963.31(17)
_computing_cell_refinement       Scalepack
_computing_data_collection       'MacScience Xpress'
_computing_data_reduction        'Denzo and Scalepack'
_computing_molecular_graphics    maXus
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9088
_diffrn_reflns_theta_full        69.97
_diffrn_reflns_theta_max         72.97
_diffrn_reflns_theta_min         5.97
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.8826
_exptl_absorpt_correction_T_min  0.8122
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0519
_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)+(0.0747P)²+0.4486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                1720
_reflns_number_total             1793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401108z_si_002.cif
_cod_data_source_block           15pen
_cod_database_code               4028586
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.04691(16) -0.05021(12) 0.51100(15) 0.0226(3) Uani 1 1 d .
C2 C 0.14001(17) -0.06818(13) 0.64594(15) 0.0249(3) Uani 1 1 d .
H1 H 0.2011 -0.1372 0.6636 0.030 Uiso 1 1 calc R
C3 C 0.14408(17) 0.00957(13) 0.74918(15) 0.0269(3) Uani 1 1 d .
H2 H 0.2076 -0.0068 0.8369 0.032 Uiso 1 1 calc R
C4 C 0.05598(17) 0.11568(13) 0.73083(15) 0.0253(3) Uani 1 1 d .
O1 O 0.06874(13) 0.18974(10) 0.82977(11) 0.0328(3) Uani 1 1 d .
C5 C -0.04542(16) 0.13326(12) 0.59979(15) 0.0237(3) Uani 1 1 d .
C6 C -0.14719(17) 0.23077(13) 0.58197(15) 0.0253(3) Uani 1 1 d .
H3 H -0.2178 0.2403 0.4960 0.030 Uiso 1 1 calc R
N1 N -0.14858(15) 0.30835(11) 0.67839(14) 0.0284(3) Uani 1 1 d .
H4 H -0.070(3) 0.2920(19) 0.761(2) 0.053(6) Uiso 1 1 d .
C7 C -0.25714(18) 0.40717(13) 0.66295(17) 0.0315(4) Uani 1 1 d .
H5 H -0.3137 0.4078 0.7408 0.038 Uiso 1 1 calc R
H6 H -0.3366 0.3981 0.5766 0.038 Uiso 1 1 calc R
C8 C -0.17149(19) 0.52214(14) 0.65931(17) 0.0317(4) Uani 1 1 d .
H7 H -0.1104 0.5191 0.5846 0.038 Uiso 1 1 calc R
H8 H -0.2509 0.5848 0.6365 0.038 Uiso 1 1 calc R
C9 C -0.06012(19) 0.55278(13) 0.79329(16) 0.0306(4) Uani 1 1 d .
H9 H 0.0168 0.4888 0.8186 0.037 Uiso 1 1 calc R
H10 H -0.1215 0.5600 0.8675 0.037 Uiso 1 1 calc R
C10 C 0.0292(2) 0.66568(13) 0.78383(17) 0.0327(4) Uani 1 1 d .
H11 H 0.0979 0.6560 0.7154 0.039 Uiso 1 1 calc R
H12 H -0.0476 0.7281 0.7502 0.039 Uiso 1 1 calc R
C11 C 0.1300(2) 0.70260(16) 0.92067(19) 0.0403(4) Uani 1 1 d .
H13 H 0.0617 0.7212 0.9859 0.060 Uiso 1 1 calc R
H14 H 0.1920 0.7714 0.9067 0.060 Uiso 1 1 calc R
H15 H 0.2015 0.6391 0.9578 0.060 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 C1 C2 117.70(16) 3_556 .
C1 C1 C5 120.38(16) 3_556 3_556
C2 C1 C5 121.91(13) . 3_556
C3 C2 C1 122.32(14) . .
C3 C2 H1 118.8 . .
C1 C2 H1 118.8 . .
C2 C3 C4 122.30(13) . .
C2 C3 H2 118.9 . .
C4 C3 H2 118.9 . .
O1 C4 C5 122.82(14) . .
O1 C4 C3 120.34(13) . .
C5 C4 C3 116.84(13) . .
C6 C5 C4 118.70(13) . .
C6 C5 C1 120.99(13) . 3_556
C4 C5 C1 120.28(13) . 3_556
N1 C6 C5 123.03(14) . .
N1 C6 H3 118.5 . .
C5 C6 H3 118.5 . .
C6 N1 C7 123.52(13) . .
C6 N1 H4 112.1(13) . .
C7 N1 H4 124.4(13) . .
N1 C7 C8 111.95(12) . .
N1 C7 H5 109.2 . .
C8 C7 H5 109.2 . .
N1 C7 H6 109.2 . .
C8 C7 H6 109.2 . .
H5 C7 H6 107.9 . .
C9 C8 C7 114.16(13) . .
C9 C8 H7 108.7 . .
C7 C8 H7 108.7 . .
C9 C8 H8 108.7 . .
C7 C8 H8 108.7 . .
H7 C8 H8 107.6 . .
C8 C9 C10 112.71(13) . .
C8 C9 H9 109.0 . .
C10 C9 H9 109.0 . .
C8 C9 H10 109.0 . .
C10 C9 H10 109.0 . .
H9 C9 H10 107.8 . .
C11 C10 C9 113.09(14) . .
C11 C10 H11 109.0 . .
C9 C10 H11 109.0 . .
C11 C10 H12 109.0 . .
C9 C10 H12 109.0 . .
H11 C10 H12 107.8 . .
C10 C11 H13 109.5 . .
C10 C11 H14 109.5 . .
H13 C11 H14 109.5 . .
C10 C11 H15 109.5 . .
H13 C11 H15 109.5 . .
H14 C11 H15 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.403(3) 3_556
C1 C2 1.431(2) .
C1 C5 1.452(2) 3_556
C2 C3 1.353(2) .
C2 H1 0.9500 .
C3 C4 1.431(2) .
C3 H2 0.9500 .
C4 O1 1.2856(18) .
C4 C5 1.428(2) .
C5 C6 1.414(2) .
C5 C1 1.452(2) 3_556
C6 N1 1.3078(19) .
C6 H3 0.9500 .
N1 C7 1.4622(19) .
N1 H4 0.97(2) .
C7 C8 1.519(2) .
C7 H5 0.9900 .
C7 H6 0.9900 .
C8 C9 1.517(2) .
C8 H7 0.9900 .
C8 H8 0.9900 .
C9 C10 1.523(2) .
C9 H9 0.9900 .
C9 H10 0.9900 .
C10 C11 1.518(2) .
C10 H11 0.9900 .
C10 H12 0.9900 .
C11 H13 0.9800 .
C11 H14 0.9800 .
C11 H15 0.9800 .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C1 C2 C3 -2.4(3) 3_556 .
C5 C1 C2 C3 178.94(13) 3_556 .
C1 C2 C3 C4 -0.2(2) . .
C2 C3 C4 O1 -176.79(14) . .
C2 C3 C4 C5 3.8(2) . .
O1 C4 C5 C6 -6.1(2) . .
C3 C4 C5 C6 173.30(13) . .
O1 C4 C5 C1 175.85(13) . 3_556
C3 C4 C5 C1 -4.7(2) . 3_556
C4 C5 C6 N1 2.7(2) . .
C1 C5 C6 N1 -179.24(13) 3_556 .
C5 C6 N1 C7 -177.70(13) . .
C6 N1 C7 C8 -112.48(16) . .
N1 C7 C8 C9 -65.82(18) . .
C7 C8 C9 C10 177.36(13) . .
C8 C9 C10 C11 174.94(14) . .
