#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/66/1506686.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_1506686
loop_
_publ_author_name
'Gallant, Amanda J.'
'Yun, Michael'
'Sauer, Marc'
'Yeung, Charles S.'
'MacLachlan, Mark J.'
_publ_section_title
;
 Tautomerization in naphthalenediimines: a keto-enamine Schiff base
 macrocycle.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4827
_journal_page_last               4830
_journal_paper_doi               10.1021/ol051511z
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.46
_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                 103.823(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.649(5)
_cell_length_b                   7.4767(16)
_cell_length_c                   23.829(8)
_cell_measurement_reflns_used    22536
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.881
_cell_measurement_theta_min      2.8195
_cell_volume                     2015.3(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21437
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0558P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                2319
_reflns_number_total             3569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051511zsi20050628_064610.cif
_cod_data_source_block           mm030
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1506686
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
O3 O 1.11023(10) 0.18290(15) 1.14900(5) 0.0369(3) Uani 1 1 d
O2 O 0.19360(11) 0.31929(16) 0.98433(5) 0.0424(3) Uani 1 1 d
O4 O -0.44723(10) 0.49484(16) 0.79829(5) 0.0428(4) Uani 1 1 d
O1 O 0.42592(11) 0.29623(18) 1.03345(5) 0.0522(4) Uani 1 1 d
N2 N 0.02149(13) 0.30621(18) 0.89378(6) 0.0303(4) Uani 1 1 d
N1 N 0.63933(13) 0.23423(18) 1.02647(6) 0.0325(4) Uani 1 1 d
C4 C 0.46999(15) 0.19606(19) 0.94657(7) 0.0292(4) Uani 1 1 d
C3 C 0.22003(14) 0.2163(2) 0.89374(7) 0.0278(4) Uani 1 1 d
C25 C -0.16317(15) 0.4272(2) 0.90395(8) 0.0296(4) Uani 1 1 d
C26 C -0.51677(18) 0.5703(3) 0.83466(9) 0.0401(5) Uani 1 1 d
C5 C 0.30229(15) 0.14614(19) 0.86063(7) 0.0278(4) Uani 1 1 d
C21 C -0.15385(17) 0.3102(2) 0.81132(7) 0.0343(4) Uani 1 1 d
C13 C 0.76139(15) 0.2232(2) 1.05471(7) 0.0289(4) Uani 1 1 d
C6 C 0.42458(14) 0.14059(19) 0.88580(7) 0.0268(4) Uani 1 1 d
C16 C 0.99768(15) 0.1952(2) 1.11530(7) 0.0281(4) Uani 1 1 d
C15 C 0.96523(16) 0.1567(2) 1.05687(7) 0.0326(4) Uani 1 1 d
C8 C 0.50060(17) 0.0830(2) 0.85147(8) 0.0352(4) Uani 1 1 d
C11 C 0.59130(16) 0.1890(2) 0.97236(8) 0.0310(4) Uani 1 1 d
C7 C 0.26144(17) 0.0829(2) 0.80360(7) 0.0325(4) Uani 1 1 d
C14 C 0.84777(16) 0.1696(2) 1.02725(8) 0.0346(5) Uani 1 1 d
C23 C -0.33383(14) 0.4449(2) 0.82491(7) 0.0311(4) Uani 1 1 d
C17 C 0.91168(16) 0.2505(2) 1.14319(8) 0.0349(4) Uani 1 1 d
C22 C -0.27033(17) 0.3586(2) 0.78985(8) 0.0378(5) Uani 1 1 d
C12 C 0.10077(16) 0.2429(2) 0.86710(8) 0.0303(4) Uani 1 1 d
C20 C -0.09819(14) 0.3471(2) 0.86882(7) 0.0276(4) Uani 1 1 d
C18 C 0.79514(16) 0.2655(2) 1.11305(7) 0.0331(4) Uani 1 1 d
C24 C -0.28121(15) 0.4745(2) 0.88284(7) 0.0294(4) Uani 1 1 d
C19 C 1.19999(17) 0.1098(3) 1.12361(9) 0.0364(5) Uani 1 1 d
C2 C 0.39111(16) 0.2529(2) 0.98043(7) 0.0346(4) Uani 1 1 d
C10 C 0.45903(17) 0.0294(2) 0.79493(7) 0.0356(5) Uani 1 1 d
C9 C 0.33827(17) 0.0261(2) 0.77114(8) 0.0343(4) Uani 1 1 d
C1 C 0.26178(16) 0.2643(2) 0.95319(7) 0.0324(4) Uani 1 1 d
H17 H 0.9349(15) 0.276(2) 1.1832(8) 0.040(5) Uiso 1 1 d
H7 H 0.1783(15) 0.076(2) 0.7850(7) 0.034(5) Uiso 1 1 d
H19A H 1.1820(14) -0.017(2) 1.1110(7) 0.040(5) Uiso 1 1 d
H18 H 0.7353(15) 0.3038(19) 1.1322(7) 0.033(5) Uiso 1 1 d
H19C H 1.2087(14) 0.175(2) 1.0890(8) 0.041(5) Uiso 1 1 d
H25 H -0.1253(14) 0.452(2) 0.9427(7) 0.036(5) Uiso 1 1 d
H1 H 0.5779(18) 0.273(2) 1.0478(9) 0.065(6) Uiso 1 1 d
H15 H 1.0254(15) 0.126(2) 1.0388(7) 0.040(5) Uiso 1 1 d
H12 H 0.0717(13) 0.2195(19) 0.8265(7) 0.028(4) Uiso 1 1 d
H10 H 0.5173(15) -0.0080(19) 0.7718(7) 0.039(5) Uiso 1 1 d
H8 H 0.5876(16) 0.082(2) 0.8675(7) 0.046(5) Uiso 1 1 d
H26A H -0.5245(15) 0.485(2) 0.8652(8) 0.047(5) Uiso 1 1 d
H24 H -0.3235(14) 0.532(2) 0.9094(7) 0.036(5) Uiso 1 1 d
H9 H 0.3070(14) -0.012(2) 0.7334(7) 0.036(5) Uiso 1 1 d
H11 H 0.6490(16) 0.148(2) 0.9507(8) 0.049(5) Uiso 1 1 d
H19B H 1.2765(17) 0.118(2) 1.1554(8) 0.049(5) Uiso 1 1 d
H21 H -0.1146(16) 0.245(2) 0.7856(7) 0.045(5) Uiso 1 1 d
H14 H 0.8293(14) 0.1432(19) 0.9891(8) 0.034(5) Uiso 1 1 d
H2 H 0.0614(17) 0.332(2) 0.9339(9) 0.062(6) Uiso 1 1 d
H22 H -0.3095(16) 0.334(2) 0.7497(8) 0.046(5) Uiso 1 1 d
H26B H -0.5956(18) 0.592(3) 0.8084(9) 0.064(6) Uiso 1 1 d
H26C H -0.4759(17) 0.684(2) 0.8543(8) 0.059(6) Uiso 1 1 d
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
C16 O3 C19 118.10(13)
C23 O4 C26 116.57(14)
C12 N2 C20 127.25(15)
C11 N1 C13 126.09(15)
C11 C4 C2 118.84(16)
C11 C4 C6 120.44(15)
C2 C4 C6 120.69(15)
C12 C3 C1 118.74(15)
C12 C3 C5 120.66(15)
C1 C3 C5 120.57(15)
C20 C25 C24 121.63(16)
C6 C5 C7 118.34(15)
C6 C5 C3 120.20(14)
C7 C5 C3 121.46(15)
C22 C21 C20 119.82(17)
C14 C13 C18 118.40(16)
C14 C13 N1 123.40(16)
C18 C13 N1 118.19(15)
C5 C6 C8 118.31(15)
C5 C6 C4 119.87(14)
C8 C6 C4 121.82(15)
O3 C16 C15 124.78(15)
O3 C16 C17 116.01(15)
C15 C16 C17 119.21(17)
C16 C15 C14 119.85(17)
C10 C8 C6 122.26(17)
N1 C11 C4 124.47(17)
C9 C7 C5 121.87(17)
C13 C14 C15 121.36(17)
O4 C23 C24 124.30(15)
O4 C23 C22 115.92(15)
C24 C23 C22 119.78(16)
C18 C17 C16 120.45(17)
C21 C22 C23 120.88(17)
N2 C12 C3 124.28(17)
C25 C20 C21 118.93(16)
C25 C20 N2 117.65(15)
C21 C20 N2 123.42(15)
C17 C18 C13 120.69(17)
C23 C24 C25 118.83(16)
O1 C2 C4 122.83(16)
O1 C2 C1 117.77(15)
C4 C2 C1 119.40(15)
C8 C10 C9 119.38(17)
C7 C9 C10 119.69(18)
O2 C1 C3 123.02(16)
O2 C1 C2 117.93(15)
C3 C1 C2 119.05(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C16 1.367(2)
O3 C19 1.435(2)
O2 C1 1.2775(19)
O4 C23 1.373(2)
O4 C26 1.436(2)
O1 C2 1.273(2)
N2 C12 1.327(2)
N2 C20 1.412(2)
N1 C11 1.321(2)
N1 C13 1.423(2)
C4 C11 1.401(2)
C4 C2 1.425(2)
C4 C6 1.478(2)
C3 C12 1.397(2)
C3 C1 1.429(2)
C3 C5 1.476(2)
C25 C20 1.391(2)
C25 C24 1.392(2)
C5 C6 1.408(2)
C5 C7 1.410(2)
C21 C22 1.379(3)
C21 C20 1.396(2)
C13 C14 1.384(2)
C13 C18 1.388(2)
C6 C8 1.409(2)
C16 C15 1.383(2)
C16 C17 1.391(2)
C15 C14 1.385(3)
C8 C10 1.378(2)
C7 C9 1.382(2)
C23 C24 1.388(2)
C23 C22 1.399(2)
C17 C18 1.380(3)
C2 C1 1.494(3)
C10 C9 1.386(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651742
