#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/06/2200609.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_2200609
loop_
_publ_author_name
'Yatsenko, A. V.'
'Paseshnichenko, K. A.'
_publ_section_title
;
 π--π Stacks and C--H···O bonded sheets in
 4-[(2-nitrophenyl)hydrazono]-4H-naphthalen-1-one
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1025
_journal_page_last               o1026
_journal_paper_doi               10.1107/S160053680101621X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C16 H11 N3 O3'
_chemical_formula_moiety         'C16 H11 N3 O3'
_chemical_formula_sum            'C16 H11 N3 O3'
_chemical_formula_weight         293.28
_chemical_melting_point          517
_chemical_name_systematic
;
4-[(2-nitrophenyl)hydrazono]-4H-naphthalen-1-one
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.33(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.328(2)
_cell_length_b                   16.366(4)
_cell_length_c                   11.131(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.3
_cell_measurement_theta_min      14.7
_cell_volume                     1317.3(6)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0175
_diffrn_reflns_av_sigmaI/netI    .0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3173
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          .55
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .09
_refine_diff_density_max         .201
_refine_diff_density_min         -.156
_refine_ls_extinction_coef       .0027(8)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.309
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.309
_refine_ls_R_factor_all          .0748
_refine_ls_R_factor_gt           .0450
_refine_ls_shift/su_max          .006
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.04P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1077
_reflns_number_gt                2041
_reflns_number_total             3025
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6106.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200609
_cod_database_fobs_code          2200609
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_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
O1 .60667(17) .57864(7) .93712(9) .0572(4) Uani d . 1 . . O
O2 .23492(18) .27875(7) .44880(11) .0656(4) Uani d . 1 . . O
O3 .1408(2) .20724(7) .28875(13) .0759(4) Uani d . 1 . . O
N1 .21431(17) .43700(7) .44329(10) .0401(3) Uani d . 1 . . N
N2 .23925(16) .51405(7) .48507(10) .0380(3) Uani d . 1 . . N
N3 .15886(19) .27320(8) .34107(13) .0498(4) Uani d . 1 . . N
C1 .5250(2) .56377(9) .83466(13) .0386(4) Uani d . 1 . . C
C2 .5072(2) .48104(9) .78856(14) .0425(4) Uani d . 1 . . C
C3 .4199(2) .46339(9) .67641(14) .0426(4) Uani d . 1 . . C
C4 .33440(19) .52586(8) .59335(12) .0336(3) Uani d . 1 . . C
C5 .2814(2) .67590(9) .55850(14) .0445(4) Uani d . 1 . . C
C6 .2949(2) .75520(10) .59902(16) .0517(4) Uani d . 1 . . C
C7 .3810(2) .77243(9) .71679(16) .0523(4) Uani d . 1 . . C
C8 .4546(2) .71045(10) .79169(15) .0469(4) Uani d . 1 . . C
C9 .4430(2) .62964(9) .75147(13) .0366(3) Uani d . 1 . . C
C10 .35333(19) .61141(8) .63376(12) .0352(3) Uani d . 1 . . C
C11 .11540(19) .42454(8) .32735(12) .0356(3) Uani d . 1 . . C
C12 .0890(2) .34606(9) .27546(13) .0390(4) Uani d . 1 . . C
C13 -.0090(2) .33540(11) .15852(15) .0478(4) Uani d . 1 . . C
C14 -.0833(2) .40066(11) .09289(15) .0523(5) Uani d . 1 . . C
C15 -.0601(2) .47837(11) .14233(15) .0491(4) Uani d . 1 . . C
C16 .0393(2) .49030(9) .25649(14) .0416(4) Uani d . 1 . . C
H2 .555(2) .4411(10) .8370(14) .053(5) Uiso d . 1 . . H
H3 .419(2) .4083(11) .6500(16) .069(5) Uiso d . 1 . . H
H5 .226(2) .6630(10) .4827(15) .051(5) Uiso d . 1 . . H
H6 .241(2) .7953(11) .5459(14) .061(5) Uiso d . 1 . . H
H7 .383(2) .8270(10) .7417(13) .055(5) Uiso d . 1 . . H
H8 .508(2) .7184(11) .8724(16) .062(5) Uiso d . 1 . . H
H13 -.022(3) .2800(12) .1302(16) .072(6) Uiso d . 1 . . H
H14 -.153(2) .3925(10) .0167(15) .060(5) Uiso d . 1 . . H
H15 -.114(2) .5221(10) .0985(14) .055(5) Uiso d . 1 . . H
H16 .054(2) .5419(10) .2910(13) .052(5) Uiso d . 1 . . H
H1 .257(2) .3828(10) .4895(13) .047(4) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
N2 N1 C11 118.67(12) yes
N2 N1 H1 127.6(8) no
C11 N1 H1 113.7(8) no
C4 N2 N1 118.69(12) yes
O3 N3 O2 121.44(14) no
O3 N3 C12 118.97(14) no
O2 N3 C12 119.59(13) no
O1 C1 C2 121.28(14) no
O1 C1 C9 121.65(14) no
C2 C1 C9 117.06(13) no
C3 C2 C1 122.32(14) no
C3 C2 H2 119.5(10) no
C1 C2 H2 118.2(10) no
C2 C3 C4 122.28(14) no
C2 C3 H3 118.1(11) no
C4 C3 H3 119.5(11) no
N2 C4 C3 126.51(13) yes
N2 C4 C10 115.68(12) yes
C3 C4 C10 117.81(12) no
C6 C5 C10 121.16(15) no
C6 C5 H5 121.9(11) no
C10 C5 H5 117.0(11) no
C5 C6 C7 119.99(15) no
C5 C6 H6 117.3(11) no
C7 C6 H6 122.7(11) no
C8 C7 C6 119.93(15) no
C8 C7 H7 122.9(10) no
C6 C7 H7 117.1(10) no
C7 C8 C9 120.70(15) no
C7 C8 H8 123.3(11) no
C9 C8 H8 115.9(11) no
C8 C9 C10 119.84(14) no
C8 C9 C1 119.45(13) no
C10 C9 C1 120.71(13) no
C5 C10 C9 118.35(13) no
C5 C10 C4 121.90(13) no
C9 C10 C4 119.75(12) no
N1 C11 C16 120.81(13) no
N1 C11 C12 122.09(13) no
C16 C11 C12 117.10(13) no
C13 C12 C11 120.90(14) no
C13 C12 N3 117.07(14) no
C11 C12 N3 122.02(13) no
C14 C13 C12 120.39(16) no
C14 C13 H13 123.9(11) no
C12 C13 H13 115.7(11) no
C13 C14 C15 119.73(15) no
C13 C14 H14 119.6(11) no
C15 C14 H14 120.6(11) no
C16 C15 C14 120.73(16) no
C16 C15 H15 119.9(10) no
C14 C15 H15 119.3(10) no
C15 C16 C11 121.12(15) no
C15 C16 H16 121.5(10) no
C11 C16 H16 117.3(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2235(17) yes
O2 N3 . 1.2410(16) no
O3 N3 . 1.2235(16) no
N1 N2 . 1.3462(17) yes
N1 C11 . 1.3889(17) no
N1 H1 . 1.047(15) no
N2 C4 . 1.3053(17) yes
N3 C12 . 1.4479(19) no
C1 C2 . 1.446(2) yes
C1 C9 . 1.483(2) yes
C2 C3 . 1.339(2) yes
C2 H2 . .884(16) no
C3 C4 . 1.451(2) yes
C3 H3 . .949(18) no
C4 C10 . 1.4703(19) yes
C5 C6 . 1.372(2) no
C5 C10 . 1.397(2) no
C5 H5 . .900(16) no
C6 C7 . 1.389(2) no
C6 H6 . .929(17) no
C7 C8 . 1.367(2) no
C7 H7 . .935(16) no
C8 C9 . 1.394(2) no
C8 H8 . .929(17) no
C9 C10 . 1.3995(19) no
C11 C16 . 1.396(2) no
C11 C12 . 1.409(2) no
C12 C13 . 1.392(2) no
C13 C14 . 1.357(2) no
C13 H13 . .960(19) no
C14 C15 . 1.385(2) no
C14 H14 . .926(17) no
C15 C16 . 1.372(2) no
C15 H15 . .918(16) no
C16 H16 . .927(16) no
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
N1 H1 O2 . 1.05(2) 1.76(2) 2.594(2) 133.0(10) yes
C2 H2 O3 2_555 .88(2) 2.58(2) 3.233(2) 131.0(10) yes
C6 H6 O1 2_464 .93(2) 2.51(2) 3.426(2) 169.0(10) yes
C13 H13 O2 2_454 .96(2) 2.65(2) 3.323(2) 128.0(10) yes
C15 H15 O1 1_454 .92(2) 2.66(2) 3.474(2) 148.0(10) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12996115
