#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:35:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180306 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/20/7152078.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_7152078
loop_
_publ_author_name
'Martínez, R Fernando'
'Avalos, Martín'
'Babiano, Reyes'
'Cintas, Pedro'
'Jiménez, José L'
'Light, Mark E.'
'Palacios, Juan C.'
_publ_section_title
;
 Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and
 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8268
_journal_page_last               8275
_journal_paper_doi               10.1039/c1ob06073b
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'Pedro Cintas'
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39
_chemical_name_common            NAFTBU
_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                 103.012(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5131(2)
_cell_length_b                   12.4731(4)
_cell_length_c                   15.8417(5)
_cell_measurement_reflns_used    17297
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1638.95(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20079
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0571
_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)+(0.0830P)²+0.0946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1604
_reflns_number_gt                2486
_reflns_number_total             3746
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1ob06073b.txt
_cod_data_source_block           2010acc0779
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/n
_cod_database_code               7152078
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 0.4309(2) 0.24450(13) 0.05201(11) 0.0262(4) Uani 1 1 d .
C2 C 0.5448(2) 0.17770(14) 0.02176(11) 0.0276(4) Uani 1 1 d .
C3 C 0.7052(2) 0.16865(15) 0.07007(12) 0.0318(4) Uani 1 1 d .
H3 H 0.7365 0.2033 0.1247 0.038 Uiso 1 1 calc R
C4 C 0.8156(2) 0.11056(17) 0.03886(13) 0.0417(5) Uani 1 1 d .
H4 H 0.9239 0.1062 0.0710 0.050 Uiso 1 1 calc R
C5 C 0.7687(3) 0.05738(18) -0.04073(14) 0.0470(6) Uani 1 1 d .
H5 H 0.8457 0.0163 -0.0618 0.056 Uiso 1 1 calc R
C6 C 0.6137(3) 0.06362(16) -0.08861(13) 0.0410(5) Uani 1 1 d .
H6 H 0.5843 0.0266 -0.1422 0.049 Uiso 1 1 calc R
C7 C 0.4970(2) 0.12471(14) -0.05901(12) 0.0327(4) Uani 1 1 d .
C8 C 0.3354(2) 0.13578(15) -0.10852(12) 0.0361(5) Uani 1 1 d .
H8 H 0.3025 0.0989 -0.1620 0.043 Uiso 1 1 calc R
C9 C 0.2289(2) 0.19870(15) -0.07950(12) 0.0336(4) Uani 1 1 d .
H9 H 0.1217 0.2045 -0.1131 0.040 Uiso 1 1 calc R
C10 C 0.2730(2) 0.25665(14) 0.00031(11) 0.0274(4) Uani 1 1 d .
C11 C 0.1633(2) 0.32874(14) 0.02609(11) 0.0292(4) Uani 1 1 d .
H11 H 0.0582 0.3365 -0.0097 0.035 Uiso 1 1 calc R
C12 C 0.09236(19) 0.45215(14) 0.12785(11) 0.0261(4) Uani 1 1 d .
C13 C -0.0674(2) 0.41888(15) 0.11508(12) 0.0317(4) Uani 1 1 d .
H13 H -0.1002 0.3544 0.0842 0.038 Uiso 1 1 calc R
C14 C -0.1793(2) 0.47791(16) 0.14660(12) 0.0361(5) Uani 1 1 d .
H14 H -0.2885 0.4552 0.1366 0.043 Uiso 1 1 calc R
C15 C -0.1298(2) 0.57006(16) 0.19273(12) 0.0358(5) Uani 1 1 d .
H15 H -0.2050 0.6111 0.2153 0.043 Uiso 1 1 calc R
C16 C 0.0293(2) 0.60332(15) 0.20637(11) 0.0316(4) Uani 1 1 d .
H16 H 0.0604 0.6671 0.2386 0.038 Uiso 1 1 calc R
C17 C 0.14601(19) 0.54681(14) 0.17467(11) 0.0261(4) Uani 1 1 d .
C18 C 0.3218(2) 0.58776(14) 0.19119(11) 0.0293(4) Uani 1 1 d .
C19 C 0.4352(2) 0.50979(16) 0.25128(11) 0.0342(5) Uani 1 1 d .
H19A H 0.5435 0.5409 0.2675 0.051 Uiso 1 1 calc R
H19B H 0.4396 0.4417 0.2211 0.051 Uiso 1 1 calc R
H19C H 0.3945 0.4971 0.3036 0.051 Uiso 1 1 calc R
C20 C 0.3741(2) 0.60224(16) 0.10503(12) 0.0341(5) Uani 1 1 d .
H20A H 0.3013 0.6528 0.0682 0.051 Uiso 1 1 calc R
H20B H 0.3700 0.5329 0.0755 0.051 Uiso 1 1 calc R
H20C H 0.4845 0.6302 0.1165 0.051 Uiso 1 1 calc R
C21 C 0.3400(2) 0.69715(17) 0.23688(14) 0.0449(5) Uani 1 1 d .
H21A H 0.3139 0.6900 0.2938 0.067 Uiso 1 1 calc R
H21B H 0.2665 0.7489 0.2018 0.067 Uiso 1 1 calc R
H21C H 0.4513 0.7224 0.2442 0.067 Uiso 1 1 calc R
N1 N 0.20236(16) 0.38453(11) 0.09719(9) 0.0261(3) Uani 1 1 d .
H902 H 0.3021 0.3802 0.1279 0.031 Uiso 0.50 1 calc PR
O1 O 0.47903(13) 0.29526(10) 0.12595(7) 0.0306(3) Uani 1 1 d .
H901 H 0.3986 0.3204 0.1417 0.046 Uiso 0.50 1 calc PR
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
O1 C1 C10 121.94(15)
O1 C1 C2 118.55(15)
C10 C1 C2 119.48(15)
C3 C2 C7 119.94(16)
C3 C2 C1 120.49(16)
C7 C2 C1 119.51(15)
C4 C3 C2 120.46(18)
C3 C4 C5 119.85(18)
C6 C5 C4 121.06(18)
C5 C6 C7 120.60(19)
C6 C7 C2 118.08(17)
C6 C7 C8 122.13(17)
C2 C7 C8 119.78(16)
C9 C8 C7 120.32(17)
C8 C9 C10 121.97(17)
C1 C10 C11 120.08(15)
C1 C10 C9 118.87(16)
C11 C10 C9 121.00(15)
N1 C11 C10 122.04(15)
C13 C12 C17 120.96(16)
C13 C12 N1 118.01(16)
C17 C12 N1 120.91(14)
C14 C13 C12 121.23(17)
C15 C14 C13 118.88(16)
C14 C15 C16 120.28(17)
C15 C16 C17 122.74(17)
C16 C17 C12 115.89(15)
C16 C17 C18 120.72(16)
C12 C17 C18 123.39(15)
C21 C18 C20 107.17(16)
C21 C18 C19 106.69(14)
C20 C18 C19 110.89(14)
C21 C18 C17 111.35(15)
C20 C18 C17 110.54(14)
C19 C18 C17 110.11(14)
C11 N1 C12 123.50(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3131(19)
C1 C10 1.417(2)
C1 C2 1.440(2)
C2 C3 1.411(2)
C2 C7 1.416(2)
C3 C4 1.364(3)
C4 C5 1.401(3)
C5 C6 1.368(3)
C6 C7 1.414(3)
C7 C8 1.428(3)
C8 C9 1.356(3)
C9 C10 1.431(2)
C10 C11 1.421(2)
C11 N1 1.302(2)
C12 C13 1.393(2)
C12 C17 1.414(2)
C12 N1 1.425(2)
C13 C14 1.383(3)
C14 C15 1.376(3)
C15 C16 1.386(3)
C16 C17 1.401(2)
C17 C18 1.547(2)
C18 C21 1.536(3)
C18 C20 1.539(3)
C18 C19 1.539(2)
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
O1 H901 N1 0.84 1.84 2.5518(17) 141.1
