#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/73/2207393.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207393
loop_
_publ_author_name
'Liu, Xin-Gang'
'Feng, Ya-Qing'
'Liang, Zu-Pei'
'Wang, Wei'
_publ_section_title
;
 1-[(4-Formylphenyl)hydrazono]naphthalen-2(1H)-one--2-naphthol
 (1/1)
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3857
_journal_page_last               o3858
_journal_paper_doi               10.1107/S1600536805033957
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H12 N2 O2, C10 H8 O'
_chemical_formula_moiety         'C17 H12 N2 O2, C10 H8 O'
_chemical_formula_sum            'C27 H20 N2 O3'
_chemical_formula_weight         420.45
_chemical_melting_point          410.0(10)
_chemical_name_systematic
;
1-[(4-formylphenyl)hydrazono]naphthalen-2(1H)-one--2-naphthol (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                86.421(3)
_cell_angle_beta                 89.184(3)
_cell_angle_gamma                83.715(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9088(12)
_cell_length_b                   10.7469(16)
_cell_length_c                   12.3067(19)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.59
_cell_volume                     1037.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5880
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0551
_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)+(0.0904P)²+0.3211P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1912
_reflns_number_gt                2436
_reflns_number_total             4168
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6391.cif
_cod_data_source_block           I
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2207393
_cod_database_fobs_code          2207393
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.3434(2) 0.50515(19) 0.40980(15) 0.0479(5) Uani d . 1 . . N
N2 0.2751(2) 0.6010(2) 0.46135(16) 0.0519(5) Uani d . 1 . . N
H2 0.289(4) 0.679(3) 0.432(2) 0.080(9) Uiso d . 1 . . H
O1 0.4007(3) 0.7432(2) 0.31120(18) 0.0900(7) Uani d . 1 . . O
O2 -0.1270(3) 0.4370(2) 0.89404(16) 0.0832(7) Uani d . 1 . . O
C1 0.4294(3) 0.5225(2) 0.31792(18) 0.0487(6) Uani d . 1 . . C
C2 0.4554(3) 0.6449(3) 0.2673(2) 0.0619(7) Uani d . 1 . . C
C3 0.5456(3) 0.6480(3) 0.1647(2) 0.0687(8) Uani d . 1 . . C
H3 0.5602 0.7250 0.1291 0.082 Uiso calc R 1 . . H
C4 0.6087(3) 0.5428(3) 0.1198(2) 0.0639(7) Uani d . 1 . . C
H4 0.6672 0.5492 0.0540 0.077 Uiso calc R 1 . . H
C5 0.5904(3) 0.4204(3) 0.16836(19) 0.0547(6) Uani d . 1 . . C
C6 0.4992(3) 0.4093(2) 0.26695(18) 0.0490(6) Uani d . 1 . . C
C7 0.4819(3) 0.2895(3) 0.3130(2) 0.0585(7) Uani d . 1 . . C
H7 0.4202 0.2804 0.3774 0.070 Uiso calc R 1 . . H
C8 0.5547(4) 0.1847(3) 0.2648(2) 0.0683(8) Uani d . 1 . . C
H8 0.5426 0.1056 0.2972 0.082 Uiso calc R 1 . . H
C9 0.6462(4) 0.1955(3) 0.1681(2) 0.0723(8) Uani d . 1 . . C
H9 0.6962 0.1242 0.1362 0.087 Uiso calc R 1 . . H
C10 0.6622(3) 0.3119(3) 0.1202(2) 0.0675(8) Uani d . 1 . . C
H10 0.7215 0.3192 0.0547 0.081 Uiso calc R 1 . . H
C11 0.1791(3) 0.5810(2) 0.55579(17) 0.0441(5) Uani d . 1 . . C
C12 0.1043(3) 0.6856(2) 0.6061(2) 0.0545(6) Uani d . 1 . . C
H12 0.1177 0.7657 0.5767 0.065 Uiso calc R 1 . . H
C13 0.0101(3) 0.6699(2) 0.6999(2) 0.0545(6) Uani d . 1 . . C
H13 -0.0408 0.7398 0.7334 0.065 Uiso calc R 1 . . H
C14 -0.0096(3) 0.5509(2) 0.74492(18) 0.0463(5) Uani d . 1 . . C
C15 0.0644(3) 0.4473(2) 0.69288(18) 0.0478(6) Uani d . 1 . . C
H15 0.0501 0.3673 0.7222 0.057 Uiso calc R 1 . . H
C16 0.1580(3) 0.4607(2) 0.59915(18) 0.0467(5) Uani d . 1 . . C
H16 0.2068 0.3905 0.5650 0.056 Uiso calc R 1 . . H
C17 -0.1049(3) 0.5354(3) 0.8472(2) 0.0601(7) Uani d . 1 . . C
H17 -0.1523 0.6079 0.8784 0.072 Uiso calc R 1 . . H
C18 0.8446(4) 1.0972(2) 0.9089(2) 0.0607(7) Uani d D 1 . . C
H18 0.8291 1.1773 0.8748 0.073 Uiso calc R 1 . . H
C19 0.7280(4) 1.0168(3) 0.8958(2) 0.0648(7) Uani d D 1 . . C
H19A 0.6347 1.0409 0.8512 0.078 Uiso calc PR 0.50 A 2 H
C20 0.7468(4) 0.8965(3) 0.9492(2) 0.0721(8) Uani d D 1 B . C
H20 0.6640 0.8427 0.9413 0.087 Uiso calc R 1 . . H
C21 0.8847(4) 0.8580(3) 1.0125(2) 0.0668(7) Uani d . 1 . . C
H21 0.8959 0.7779 1.0467 0.080 Uiso calc R 1 B . H
C22 1.0103(3) 0.9384(2) 1.02654(18) 0.0546(6) Uani d . 1 . . C
O3 0.6013(5) 1.0485(3) 0.8288(3) 0.0664(10) Uani d PD 0.50 B 1 O
H3A 0.6182 1.1126 0.7926 0.100 Uiso calc PR 0.50 B 1 H
O4 0.7492(9) 0.8641(6) 0.3000(6) 0.141(2) Uani d PD 0.50 C 1 O
H4A 0.6483 0.8444 0.3073 0.169 Uiso d PR 0.50 C 1 H
C23 0.9748(6) 0.9409(3) 0.3636(3) 0.0955(12) Uani d D 1 . . C
H23 1.0344 0.9309 0.2985 0.115 Uiso calc R 1 . . H
C24 0.8175(7) 0.9060(4) 0.3755(4) 0.1079(14) Uani d D 1 . . C
H24A 0.7727 0.8713 0.3163 0.130 Uiso calc PR 0.50 C 2 H
C25 0.7151(6) 0.9168(3) 0.4678(4) 0.1136(15) Uani d D 1 C . C
H25 0.6064 0.8913 0.4718 0.136 Uiso calc R 1 . . H
C26 0.7874(5) 0.9682(3) 0.5524(3) 0.0974(12) Uani d . 1 . . C
H26 0.7243 0.9779 0.6163 0.117 Uiso calc R 1 C . H
C27 0.9516(5) 1.0071(3) 0.5482(3) 0.0807(10) Uani d . 1 . . C
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N2 N1 C1 . . 120.5(2)
N1 N2 C11 . . 119.7(2)
N1 N2 H2 . . 118.0(19)
C11 N2 H2 . . 122.2(19)
N1 C1 C2 . . 124.2(2)
N1 C1 C6 . . 115.9(2)
C2 C1 C6 . . 119.9(2)
O1 C2 C3 . . 121.6(3)
O1 C2 C1 . . 120.9(2)
C3 C2 C1 . . 117.5(3)
C4 C3 C2 . . 121.4(3)
C4 C3 H3 . . 119.3
C2 C3 H3 . . 119.3
C3 C4 C5 . . 123.0(2)
C3 C4 H4 . . 118.5
C5 C4 H4 . . 118.5
C10 C5 C6 . . 119.5(3)
C10 C5 C4 . . 121.4(2)
C6 C5 C4 . . 119.1(2)
C7 C6 C5 . . 118.4(2)
C7 C6 C1 . . 122.5(2)
C5 C6 C1 . . 119.1(2)
C8 C7 C6 . . 121.0(2)
C8 C7 H7 . . 119.5
C6 C7 H7 . . 119.5
C7 C8 C9 . . 120.7(3)
C7 C8 H8 . . 119.7
C9 C8 H8 . . 119.7
C10 C9 C8 . . 119.5(3)
C10 C9 H9 . . 120.3
C8 C9 H9 . . 120.3
C9 C10 C5 . . 120.9(2)
C9 C10 H10 . . 119.5
C5 C10 H10 . . 119.5
C12 C11 C16 . . 120.4(2)
C12 C11 N2 . . 117.8(2)
C16 C11 N2 . . 121.8(2)
C13 C12 C11 . . 119.6(2)
C13 C12 H12 . . 120.2
C11 C12 H12 . . 120.2
C12 C13 C14 . . 120.7(2)
C12 C13 H13 . . 119.7
C14 C13 H13 . . 119.7
C13 C14 C15 . . 119.0(2)
C13 C14 C17 . . 120.2(2)
C15 C14 C17 . . 120.8(2)
C16 C15 C14 . . 121.3(2)
C16 C15 H15 . . 119.3
C14 C15 H15 . . 119.3
C15 C16 C11 . . 119.0(2)
C15 C16 H16 . . 120.5
C11 C16 H16 . . 120.5
O2 C17 C14 . . 125.6(3)
O2 C17 H17 . . 117.2
C14 C17 H17 . . 117.2
C19 C18 C22 . 2_777 120.9(2)
C19 C18 H18 . . 119.5
C22 C18 H18 2_777 . 119.5
O3 C19 C18 . . 119.8(3)
O3 C19 C20 . . 119.8(3)
C18 C19 C20 . . 120.4(3)
O3 C19 H19A . . 2.9
C18 C19 H19A . . 119.8
C20 C19 H19A . . 119.8
C21 C20 C19 . . 120.8(3)
C21 C20 H20 . . 119.6
C19 C20 H20 . . 119.6
C20 C21 C22 . . 120.5(3)
C20 C21 H21 . . 119.8
C22 C21 H21 . . 119.8
C21 C22 C18 . 2_777 122.5(2)
C21 C22 C22 . 2_777 118.7(3)
C18 C22 C22 2_777 2_777 118.7(3)
C19 O3 H3A . . 109.5
C24 O4 H4A . . 119.9
C24 C23 C27 . 2_776 118.9(4)
C24 C23 H23 . . 120.6
C27 C23 H23 2_776 . 120.6
O4 C24 C23 . . 120.3(6)
O4 C24 C25 . . 113.5(6)
C23 C24 C25 . . 126.2(5)
O4 C24 H24A . . 4.0
C23 C24 H24A . . 116.9
C25 C24 H24A . . 116.9
C26 C25 C24 . . 114.4(5)
C26 C25 H25 . . 122.8
C24 C25 H25 . . 122.8
C25 C26 C27 . . 123.7(4)
C25 C26 H26 . . 118.1
C27 C26 H26 . . 118.1
C26 C27 C27 . 2_776 118.7(5)
C26 C27 C23 . 2_776 123.2(3)
C27 C27 C23 2_776 2_776 118.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 N2 . 1.306(3)
N1 C1 . 1.325(3)
N2 C11 . 1.397(3)
N2 H2 . 0.91(3)
O1 C2 . 1.250(3)
O2 C17 . 1.200(3)
C1 C2 . 1.454(4)
C1 C6 . 1.455(3)
C2 C3 . 1.441(4)
C3 C4 . 1.334(4)
C3 H3 . 0.9300
C4 C5 . 1.431(4)
C4 H4 . 0.9300
C5 C10 . 1.402(4)
C5 C6 . 1.408(3)
C6 C7 . 1.394(4)
C7 C8 . 1.372(4)
C7 H7 . 0.9300
C8 C9 . 1.390(4)
C8 H8 . 0.9300
C9 C10 . 1.367(4)
C9 H9 . 0.9300
C10 H10 . 0.9300
C11 C12 . 1.388(3)
C11 C16 . 1.394(3)
C12 C13 . 1.376(3)
C12 H12 . 0.9300
C13 C14 . 1.385(3)
C13 H13 . 0.9300
C14 C15 . 1.388(3)
C14 C17 . 1.468(3)
C15 C16 . 1.370(3)
C15 H15 . 0.9300
C16 H16 . 0.9300
C17 H17 . 0.9300
C18 C19 . 1.349(4)
C18 C22 2_777 1.410(4)
C18 H18 . 0.9300
C19 O3 . 1.309(4)
C19 C20 . 1.407(4)
C19 H19A . 0.9300
C20 C21 . 1.361(4)
C20 H20 . 0.9300
C21 C22 . 1.405(4)
C21 H21 . 0.9300
C22 C18 2_777 1.410(4)
C22 C22 2_777 1.433(5)
O3 H3A . 0.8200
O4 C24 . 1.215(7)
O4 H4A . 0.8500
C23 C24 . 1.342(6)
C23 C27 2_776 1.412(5)
C23 H23 . 0.9300
C24 C25 . 1.390(6)
C24 H24A . 0.9300
C25 C26 . 1.369(6)
C25 H25 . 0.9300
C26 C27 . 1.407(5)
C26 H26 . 0.9300
C27 C27 2_776 1.411(6)
C27 C23 2_776 1.412(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 . 0.91(3) 1.86(3) 2.582(3) 135(3) y
O3 H3A O1 2_676 0.82 1.94 2.737(4) 164 y
O4 H4A O1 . 0.85 2.34 3.171(8) 166 y
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C1 N1 N2 C11 . . 177.44(19)
N2 N1 C1 C2 . . 0.0(3)
N2 N1 C1 C6 . . -179.60(19)
N1 C1 C2 O1 . . 2.4(4)
C6 C1 C2 O1 . . -178.0(2)
N1 C1 C2 C3 . . -177.3(2)
C6 C1 C2 C3 . . 2.3(3)
O1 C2 C3 C4 . . 177.8(3)
C1 C2 C3 C4 . . -2.5(4)
C2 C3 C4 C5 . . 0.8(4)
C3 C4 C5 C10 . . -178.3(3)
C3 C4 C5 C6 . . 1.2(4)
C10 C5 C6 C7 . . -0.7(3)
C4 C5 C6 C7 . . 179.8(2)
C10 C5 C6 C1 . . 178.2(2)
C4 C5 C6 C1 . . -1.3(3)
N1 C1 C6 C7 . . -1.9(3)
C2 C1 C6 C7 . . 178.4(2)
N1 C1 C6 C5 . . 179.23(19)
C2 C1 C6 C5 . . -0.4(3)
C5 C6 C7 C8 . . 1.2(4)
C1 C6 C7 C8 . . -177.6(2)
C6 C7 C8 C9 . . -0.6(4)
C7 C8 C9 C10 . . -0.7(4)
C8 C9 C10 C5 . . 1.3(4)
C6 C5 C10 C9 . . -0.6(4)
C4 C5 C10 C9 . . 179.0(3)
N1 N2 C11 C12 . . -178.04(19)
N1 N2 C11 C16 . . 2.0(3)
C16 C11 C12 C13 . . 0.6(3)
N2 C11 C12 C13 . . -179.4(2)
C11 C12 C13 C14 . . 0.5(4)
C12 C13 C14 C15 . . -1.2(4)
C12 C13 C14 C17 . . 177.7(2)
C13 C14 C15 C16 . . 0.9(3)
C17 C14 C15 C16 . . -178.0(2)
C14 C15 C16 C11 . . 0.1(3)
C12 C11 C16 C15 . . -0.8(3)
N2 C11 C16 C15 . . 179.1(2)
C13 C14 C17 O2 . . -178.6(3)
C15 C14 C17 O2 . . 0.3(4)
C22 C18 C19 O3 2_777 . -174.7(3)
C22 C18 C19 C20 2_777 . 1.9(4)
O3 C19 C20 C21 . . 174.8(3)
C18 C19 C20 C21 . . -1.8(4)
C19 C20 C21 C22 . . 0.7(4)
C20 C21 C22 C18 . 2_777 -179.9(3)
C20 C21 C22 C22 . 2_777 0.3(4)
C27 C23 C24 O4 2_776 . 178.0(5)
C27 C23 C24 C25 2_776 . 0.6(6)
O4 C24 C25 C26 . . -177.7(5)
C23 C24 C25 C26 . . -0.1(6)
C24 C25 C26 C27 . . -0.2(5)
C25 C26 C27 C27 . 2_776 0.1(5)
C25 C26 C27 C23 . 2_776 -179.6(3)
