 
data_cif of 3b 

_publ_contact_author   'Naoki Kise' 

_publ_contact_author_email   'kise@bio.tottori-u.ac.jp'

loop_ 
_publ_author_name 
'Naoki Kise'
'Toshihiko Sakurai'

_journal_name_full    'Beilstein Journal of Organic Chemistry'   
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
1-Hydroxy-7-methoxy-2-naphthonitrile
; 
_chemical_name_common             ? 
_chemical_melting_point           454-456
_chemical_formula_moiety          'C12 H9 N O2'  
_chemical_formula_sum 
 'C12 H9 N O2' 
_chemical_formula_weight          199.20 
 
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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    'P 21/n'
_symmetry_space_group_name_Hall   '-P 2yn'
 
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' 
 
_cell_length_a                    7.4001(16) 
_cell_length_b                    11.026(4) 
_cell_length_c                    12.309(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.868(14) 
_cell_angle_gamma                 90.00 
_cell_volume                      997.1(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     2335 
_cell_measurement_theta_min       3.1 
_cell_measurement_theta_max       27.5 
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'yellow'
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.25 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.327 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              416 
_exptl_absorpt_coefficient_mu     0.092 
_exptl_absorpt_correction_type    multi-scan   
_exptl_absorpt_correction_T_min   0.9557 
_exptl_absorpt_correction_T_max   0.9819 
_exptl_absorpt_process_details    
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
 
_diffrn_ambient_temperature       298(2) 
_diffrn_radiation_wavelength      0.71075 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Rigaku RAXIS-RAPID' 
_diffrn_measurement_method        ω 
_diffrn_detector_area_resol_mean  10.00 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             9596 
_diffrn_reflns_av_R_equivalents   0.0443 
_diffrn_reflns_av_sigmaI/netI     0.0396 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.33 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              2274 
_reflns_number_gt                 1497 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'PROCESS-AUTO'
_computing_cell_refinement        'PROCESS-AUTO'
_computing_data_reduction         'PROCESS-AUTO'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   'yadokari-XG' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2274 
_refine_ls_number_parameters      138 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0732 
_refine_ls_R_factor_gt            0.0414 
_refine_ls_wR_factor_ref          0.1074 
_refine_ls_wR_factor_gt           0.0990 
_refine_ls_goodness_of_fit_ref    0.979 
_refine_ls_restrained_S_all       0.979 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
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 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.22343(16) 0.15132(10) 1.07472(10) 0.0414(3) Uani 1 1 d . . . 
O1 O 0.29040(13) 0.13672(8) 1.18073(7) 0.0547(3) Uani 1 1 d . . . 
H1 H 0.3057 0.0643 1.1939 0.082 Uiso 1 1 calc R . . 
C2 C 0.15651(17) 0.26489(11) 1.04523(10) 0.0459(3) Uani 1 1 d . . . 
C3 C 0.1554(2) 0.35554(12) 1.12792(12) 0.0575(4) Uani 1 1 d . . . 
N1 N 0.1529(2) 0.42844(11) 1.19326(11) 0.0820(5) Uani 1 1 d . . . 
C4 C 0.08526(17) 0.29096(12) 0.93660(11) 0.0506(3) Uani 1 1 d . . . 
H2 H 0.0417 0.3683 0.9180 0.061 Uiso 1 1 calc R . . 
C5 C 0.08018(17) 0.20374(12) 0.85958(11) 0.0493(3) Uani 1 1 d . . . 
H3 H 0.0316 0.2208 0.7880 0.059 Uiso 1 1 calc R . . 
C6 C 0.14825(15) 0.08645(11) 0.88687(9) 0.0436(3) Uani 1 1 d . . . 
C7 C 0.14395(18) -0.00672(13) 0.80778(11) 0.0562(4) Uani 1 1 d . . . 
H4 H 0.0983 0.0098 0.7356 0.067 Uiso 1 1 calc R . . 
C8 C 0.20485(19) -0.11927(14) 0.83506(11) 0.0594(4) Uani 1 1 d . . . 
H5 H 0.1986 -0.1795 0.7818 0.071 Uiso 1 1 calc R . . 
C9 C 0.27734(17) -0.14646(11) 0.94250(11) 0.0486(3) Uani 1 1 d . . . 
O2 O 0.33352(14) -0.26421(8) 0.95812(8) 0.0652(3) Uani 1 1 d . . . 
C10 C 0.4068(2) -0.29879(13) 1.06500(13) 0.0692(4) Uani 1 1 d . . . 
H6 H 0.5125 -0.2506 1.0880 0.104 Uiso 1 1 calc R . . 
H7 H 0.4402 -0.3829 1.0652 0.104 Uiso 1 1 calc R . . 
H8 H 0.3173 -0.2863 1.1143 0.104 Uiso 1 1 calc R . . 
C11 C 0.28740(16) -0.06014(11) 1.02154(10) 0.0428(3) Uani 1 1 d . . . 
H9 H 0.3373 -0.0786 1.0926 0.051 Uiso 1 1 calc R . . 
C12 C 0.22145(15) 0.05841(10) 0.99543(9) 0.0391(3) Uani 1 1 d . . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
C1 0.0429(6) 0.0443(7) 0.0357(7) 0.0024(5) -0.0008(5) -0.0070(5) 
O1 0.0797(6) 0.0418(5) 0.0385(5) -0.0002(4) -0.0101(4) -0.0022(4) 
C2 0.0500(7) 0.0421(7) 0.0442(7) 0.0015(6) 0.0005(6) -0.0052(6) 
C3 0.0753(9) 0.0416(7) 0.0526(9) 0.0049(7) -0.0057(7) 0.0008(7) 
N1 0.1287(13) 0.0492(7) 0.0624(9) -0.0087(7) -0.0114(8) 0.0090(7) 
C4 0.0502(8) 0.0473(7) 0.0530(8) 0.0111(6) 0.0009(6) -0.0007(6) 
C5 0.0463(7) 0.0606(8) 0.0396(7) 0.0112(6) -0.0011(6) -0.0023(6) 
C6 0.0368(6) 0.0567(7) 0.0373(7) 0.0023(6) 0.0038(5) -0.0049(6) 
C7 0.0581(8) 0.0734(10) 0.0359(7) -0.0044(7) 0.0010(6) 0.0003(7) 
C8 0.0632(9) 0.0683(10) 0.0471(8) -0.0171(7) 0.0076(7) 0.0033(7) 
C9 0.0428(7) 0.0509(7) 0.0524(8) -0.0063(6) 0.0075(6) 0.0023(6) 
O2 0.0736(6) 0.0533(6) 0.0675(7) -0.0100(5) 0.0039(5) 0.0138(5) 
C10 0.0699(10) 0.0562(9) 0.0806(12) 0.0060(8) 0.0052(9) 0.0102(7) 
C11 0.0403(6) 0.0486(7) 0.0388(7) 0.0002(5) 0.0015(5) -0.0023(5) 
C12 0.0340(6) 0.0459(7) 0.0371(7) 0.0007(5) 0.0031(5) -0.0054(5) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 O1 1.3488(14) . ? 
C1 C2 1.3791(17) . ? 
C1 C12 1.4138(16) . ? 
O1 H1 0.8200 . ? 
C2 C4 1.4071(18) . ? 
C2 C3 1.4272(18) . ? 
C3 N1 1.1388(17) . ? 
C4 C5 1.3477(18) . ? 
C4 H2 0.9300 . ? 
C5 C6 1.4137(18) . ? 
C5 H3 0.9300 . ? 
C6 C7 1.4130(18) . ? 
C6 C12 1.4147(16) . ? 
C7 C8 1.349(2) . ? 
C7 H4 0.9300 . ? 
C8 C9 1.399(2) . ? 
C8 H5 0.9300 . ? 
C9 C11 1.3567(17) . ? 
C9 O2 1.3697(16) . ? 
O2 C10 1.4139(18) . ? 
C10 H6 0.9600 . ? 
C10 H7 0.9600 . ? 
C10 H8 0.9600 . ? 
C11 C12 1.4185(18) . ? 
C11 H9 0.9300 . ? 
 
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 
 _geom_angle_publ_flag 
O1 C1 C2 116.22(11) . . ? 
O1 C1 C12 123.61(10) . . ? 
C2 C1 C12 120.17(11) . . ? 
C1 O1 H1 109.5 . . ? 
C1 C2 C4 121.17(12) . . ? 
C1 C2 C3 118.73(12) . . ? 
C4 C2 C3 120.08(12) . . ? 
N1 C3 C2 179.26(16) . . ? 
C5 C4 C2 119.90(12) . . ? 
C5 C4 H2 120.1 . . ? 
C2 C4 H2 120.1 . . ? 
C4 C5 C6 120.43(12) . . ? 
C4 C5 H3 119.8 . . ? 
C6 C5 H3 119.8 . . ? 
C7 C6 C5 121.56(12) . . ? 
C7 C6 C12 117.80(11) . . ? 
C5 C6 C12 120.64(11) . . ? 
C8 C7 C6 121.20(13) . . ? 
C8 C7 H4 119.4 . . ? 
C6 C7 H4 119.4 . . ? 
C7 C8 C9 120.76(13) . . ? 
C7 C8 H5 119.6 . . ? 
C9 C8 H5 119.6 . . ? 
C11 C9 O2 125.07(12) . . ? 
C11 C9 C8 120.63(12) . . ? 
O2 C9 C8 114.30(12) . . ? 
C9 O2 C10 117.54(11) . . ? 
O2 C10 H6 109.5 . . ? 
O2 C10 H7 109.5 . . ? 
H6 C10 H7 109.5 . . ? 
O2 C10 H8 109.5 . . ? 
H6 C10 H8 109.5 . . ? 
H7 C10 H8 109.5 . . ? 
C9 C11 C12 119.74(12) . . ? 
C9 C11 H9 120.1 . . ? 
C12 C11 H9 120.1 . . ? 
C1 C12 C6 117.70(11) . . ? 
C1 C12 C11 122.44(11) . . ? 
C6 C12 C11 119.86(11) . . ? 
 
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_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
O1 C1 C2 C4 179.25(11) . . . . ? 
C12 C1 C2 C4 0.01(18) . . . . ? 
O1 C1 C2 C3 -2.67(17) . . . . ? 
C12 C1 C2 C3 178.09(11) . . . . ? 
C1 C2 C3 N1 -152(14) . . . . ? 
C4 C2 C3 N1 26(14) . . . . ? 
C1 C2 C4 C5 0.61(19) . . . . ? 
C3 C2 C4 C5 -177.45(12) . . . . ? 
C2 C4 C5 C6 -0.84(18) . . . . ? 
C4 C5 C6 C7 179.77(11) . . . . ? 
C4 C5 C6 C12 0.48(18) . . . . ? 
C5 C6 C7 C8 -178.26(13) . . . . ? 
C12 C6 C7 C8 1.04(18) . . . . ? 
C6 C7 C8 C9 -1.2(2) . . . . ? 
C7 C8 C9 C11 0.2(2) . . . . ? 
C7 C8 C9 O2 179.96(12) . . . . ? 
C11 C9 O2 C10 0.38(19) . . . . ? 
C8 C9 O2 C10 -179.39(11) . . . . ? 
O2 C9 C11 C12 -178.86(12) . . . . ? 
C8 C9 C11 C12 0.90(18) . . . . ? 
O1 C1 C12 C6 -179.54(10) . . . . ? 
C2 C1 C12 C6 -0.36(16) . . . . ? 
O1 C1 C12 C11 1.26(18) . . . . ? 
C2 C1 C12 C11 -179.56(12) . . . . ? 
C7 C6 C12 C1 -179.19(10) . . . . ? 
C5 C6 C12 C1 0.12(16) . . . . ? 
C7 C6 C12 C11 0.03(16) . . . . ? 
C5 C6 C12 C11 179.34(11) . . . . ? 
C9 C11 C12 C1 178.19(10) . . . . ? 
C9 C11 C12 C6 -0.99(17) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.148 
_refine_diff_density_min   -0.119 
_refine_diff_density_rms    0.027 
