#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/31/8103157.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_8103157
loop_
_publ_author_name
'Kwang Ha'
_publ_section_title
;
 Crystal structure of
 N,N'-bis(3-ethoxy-2-hydroxy-benzylidene)-octane-1,8-diamine, C26H36N2O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              327
_journal_volume                  226
_journal_year                    2011
_chemical_formula_moiety         'C26 H36 N2 O4'
_chemical_formula_sum            'C26 H36 N2 O4'
_chemical_formula_weight         440.57
_chemical_name_systematic
; 
N,N'-Bis(3-ethoxy-2-hydroxybenzylidene)octane-1,8-diamine
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.123(4)
_cell_angle_beta                 101.625(4)
_cell_angle_gamma                101.530(4)
_cell_formula_units_Z            1
_cell_length_a                   6.9046(12)
_cell_length_b                   6.9097(12)
_cell_length_c                   12.981(2)
_cell_measurement_reflns_used    1304
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.01
_cell_volume                     593.78(17)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3645
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0593
_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)+(0.0896P)²+0.0784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                1514
_reflns_number_total             2303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3422.cff
_cod_data_source_block           etosalon
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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        593.78(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8103157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.8686(2) 0.2066(3) 0.27558(14) 0.0385(5) Uani 1 1 d .
H1 H 0.891(5) 0.315(5) 0.239(3) 0.071(10) Uiso 1 1 d .
O2 O 0.9083(2) -0.1104(2) 0.38002(13) 0.0375(5) Uani 1 1 d .
N1 N 1.0187(3) 0.4985(3) 0.17339(15) 0.0355(5) Uani 1 1 d .
C1 C 1.2130(3) 0.2659(3) 0.25218(17) 0.0308(5) Uani 1 1 d .
C2 C 1.0519(3) 0.1573(3) 0.29068(17) 0.0291(5) Uani 1 1 d .
C3 C 1.0779(3) -0.0123(3) 0.34787(17) 0.0308(5) Uani 1 1 d .
C4 C 1.2636(3) -0.0671(3) 0.36711(18) 0.0342(6) Uani 1 1 d .
H4 H 1.2818 -0.1797 0.4069 0.041 Uiso 1 1 calc R
C5 C 1.4243(4) 0.0423(3) 0.32822(19) 0.0378(6) Uani 1 1 d .
H5 H 1.5514 0.0040 0.3413 0.045 Uiso 1 1 calc R
C6 C 1.3983(4) 0.2056(3) 0.27093(18) 0.0338(6) Uani 1 1 d .
H6 H 1.5075 0.2784 0.2437 0.041 Uiso 1 1 calc R
C7 C 0.9198(4) -0.2918(3) 0.43249(19) 0.0362(6) Uani 1 1 d .
H7A H 1.0172 -0.2662 0.5007 0.043 Uiso 1 1 calc R
H7B H 0.9641 -0.3849 0.3886 0.043 Uiso 1 1 calc R
C8 C 0.7105(4) -0.3766(4) 0.4495(2) 0.0456(7) Uani 1 1 d .
H8A H 0.6702 -0.2843 0.4945 0.068 Uiso 1 1 calc R
H8B H 0.7100 -0.5031 0.4836 0.068 Uiso 1 1 calc R
H8C H 0.6153 -0.3977 0.3815 0.068 Uiso 1 1 calc R
C9 C 1.1857(3) 0.4415(3) 0.19222(18) 0.0329(5) Uani 1 1 d .
H9 H 1.2966 0.5151 0.1666 0.039 Uiso 1 1 calc R
C10 C 0.9961(4) 0.6763(3) 0.11432(19) 0.0354(6) Uani 1 1 d .
H10A H 1.0304 0.6627 0.0446 0.043 Uiso 1 1 calc R
H10B H 1.0894 0.7933 0.1529 0.043 Uiso 1 1 calc R
C11 C 0.7806(4) 0.7036(3) 0.1005(2) 0.0378(6) Uani 1 1 d .
H11A H 0.7477 0.7134 0.1709 0.045 Uiso 1 1 calc R
H11B H 0.6893 0.5848 0.0625 0.045 Uiso 1 1 calc R
C12 C 0.7395(3) 0.8853(3) 0.04068(18) 0.0346(6) Uani 1 1 d .
H12A H 0.8302 1.0046 0.0785 0.042 Uiso 1 1 calc R
H12B H 0.7711 0.8757 -0.0300 0.042 Uiso 1 1 calc R
C13 C 0.5229(4) 0.9082(3) 0.0286(2) 0.0378(6) Uani 1 1 d .
H13A H 0.4909 0.9135 0.0994 0.045 Uiso 1 1 calc R
H13B H 0.4331 0.7898 -0.0105 0.045 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 H1 100(2) . .
C3 O2 C7 117.59(17) . .
C9 N1 C10 121.1(2) . .
C2 C1 C6 119.6(2) . .
C2 C1 C9 119.5(2) . .
C6 C1 C9 120.9(2) . .
O1 C2 C1 122.86(19) . .
O1 C2 C3 117.7(2) . .
C1 C2 C3 119.46(19) . .
O2 C3 C4 125.5(2) . .
O2 C3 C2 114.55(19) . .
C4 C3 C2 119.9(2) . .
C3 C4 C5 120.3(2) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 119.9(2) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C1 120.8(2) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
O2 C7 C8 106.47(18) . .
O2 C7 H7A 110.4 . .
C8 C7 H7A 110.4 . .
O2 C7 H7B 110.4 . .
C8 C7 H7B 110.4 . .
H7A C7 H7B 108.6 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 C1 122.1(2) . .
N1 C9 H9 118.9 . .
C1 C9 H9 118.9 . .
N1 C10 C11 109.43(19) . .
N1 C10 H10A 109.8 . .
C11 C10 H10A 109.8 . .
N1 C10 H10B 109.8 . .
C11 C10 H10B 109.8 . .
H10A C10 H10B 108.2 . .
C10 C11 C12 114.1(2) . .
C10 C11 H11A 108.7 . .
C12 C11 H11A 108.7 . .
C10 C11 H11B 108.7 . .
C12 C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
C13 C12 C11 112.7(2) . .
C13 C12 H12A 109.1 . .
C11 C12 H12A 109.1 . .
C13 C12 H12B 109.1 . .
C11 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
C12 C13 C13 114.2(3) . 2_675
C12 C13 H13A 108.7 . .
C13 C13 H13A 108.7 2_675 .
C12 C13 H13B 108.7 . .
C13 C13 H13B 108.7 2_675 .
H13A C13 H13B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.352(2) .
O1 H1 0.89(3) .
O2 C3 1.374(3) .
O2 C7 1.437(2) .
N1 C9 1.270(3) .
N1 C10 1.468(3) .
C1 C2 1.394(3) .
C1 C6 1.399(3) .
C1 C9 1.467(3) .
C2 C3 1.411(3) .
C3 C4 1.384(3) .
C4 C5 1.396(3) .
C4 H4 0.9500 .
C5 C6 1.374(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.507(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9 0.9500 .
C10 C11 1.512(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.523(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.512(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C13 1.526(4) 2_675
C13 H13A 0.9900 .
C13 H13B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.89(3) 1.73(3) 2.575(3) 159(3) .
C6 H6 O1 0.95 2.59 3.235(3) 125.3 1_655
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_4
C6 C1 C2 O1 -180.0(2) .
C9 C1 C2 O1 -0.2(3) .
C6 C1 C2 C3 -0.1(3) .
C9 C1 C2 C3 179.7(2) .
C7 O2 C3 C4 -4.0(3) .
C7 O2 C3 C2 175.89(19) .
O1 C2 C3 O2 1.2(3) .
C1 C2 C3 O2 -178.62(19) .
O1 C2 C3 C4 -178.8(2) .
C1 C2 C3 C4 1.3(3) .
O2 C3 C4 C5 178.6(2) .
C2 C3 C4 C5 -1.4(3) .
C3 C4 C5 C6 0.2(4) .
C4 C5 C6 C1 1.0(4) .
C2 C1 C6 C5 -1.0(3) .
C9 C1 C6 C5 179.2(2) .
C3 O2 C7 C8 -174.8(2) .
C10 N1 C9 C1 179.2(2) .
C2 C1 C9 N1 -0.4(3) .
C6 C1 C9 N1 179.4(2) .
C9 N1 C10 C11 177.9(2) .
N1 C10 C11 C12 179.6(2) .
C10 C11 C12 C13 -179.8(2) .
C11 C12 C13 C13 178.5(3) 2_675
