#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/44/2214489.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_2214489
loop_
_publ_author_name
'Sarojini, B. K.'
'Narayana, B.'
'Sunil, K.'
'Yathirajan, H. S.'
'Bolte, Michael'
_publ_section_title
;
 N'-Isopropylidene-6-methoxy-2-naphthohydrazide
;
_journal_coeditor_code           AT2341
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3551
_journal_page_last               o3551
_journal_paper_doi               10.1107/S1600536807034599
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H16 N2 O2'
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_name_systematic
;
N'-Isopropylidene-6-methoxy-2-naphthohydrazide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 91.673(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.037(3)
_cell_length_b                   5.9957(4)
_cell_length_c                   9.3014(10)
_cell_measurement_reflns_used    8050
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      3.6
_cell_volume                     1339.9(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics
'PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8435
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.154
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1539
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0312
_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)+(0.0635P)²+0.1264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                1506
_reflns_number_total             1539
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2341.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2214489
_cod_database_fobs_code          2214489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_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
N N1 0.61518(6) 0.6094(2) 0.48733(13) 0.0305(3) Uani d . 1
H H1 0.6241(8) 0.630(3) 0.398(2) 0.033(5) Uiso d . 1
N N2 0.56452(7) 0.6965(3) 0.53277(15) 0.0438(4) Uani d . 1
O O1 0.62273(6) 0.3857(2) 0.68512(13) 0.0409(3) Uani d . 1
O O2 0.93004(5) 0.1401(2) 0.23424(16) 0.0483(4) Uani d . 1
C C1 0.69319(6) 0.3547(2) 0.51132(14) 0.0274(3) Uani d . 1
C C2 0.72496(6) 0.4663(2) 0.41240(16) 0.0282(3) Uani d . 1
H H2 0.7124 0.6055 0.3751 0.034 Uiso calc R 1
C C3 0.77597(6) 0.3761(2) 0.36589(15) 0.0276(3) Uani d . 1
C C4 0.80881(7) 0.4902(3) 0.26298(18) 0.0338(3) Uani d . 1
H H4 0.7960 0.6276 0.2234 0.041 Uiso calc R 1
C C5 0.85828(7) 0.4036(3) 0.22131(19) 0.0373(4) Uani d . 1
H H5 0.8792 0.4789 0.1510 0.045 Uiso calc R 1
C C6 0.87878(7) 0.2009(3) 0.28263(18) 0.0363(4) Uani d . 1
C C7 0.84830(7) 0.0842(3) 0.38110(17) 0.0344(3) Uani d . 1
H H7 0.8622 -0.0514 0.4208 0.041 Uiso calc R 1
C C8 0.79556(6) 0.1691(2) 0.42301(15) 0.0284(3) Uani d . 1
C C9 0.76168(7) 0.0543(2) 0.52314(16) 0.0315(3) Uani d . 1
H H9 0.7735 -0.0858 0.5607 0.038 Uiso calc R 1
C C10 0.71221(7) 0.1449(2) 0.56560(15) 0.0308(3) Uani d . 1
H H10 0.6903 0.0663 0.6323 0.037 Uiso calc R 1
C C11 0.64049(6) 0.4497(3) 0.56888(14) 0.0291(3) Uani d . 1
C C12 0.54904(7) 0.8804(3) 0.47282(16) 0.0365(4) Uani d . 1
C C13 0.49405(11) 0.9730(6) 0.5149(3) 0.0729(9) Uani d . 1
H H13A 0.4769 0.8719 0.5835 0.109 Uiso calc R 1
H H13B 0.4697 0.9880 0.4291 0.109 Uiso calc R 1
H H13C 0.4996 1.1196 0.5596 0.109 Uiso calc R 1
C C14 0.58033(8) 1.0116(3) 0.3649(2) 0.0425(4) Uani d . 1
H H14A 0.6202 1.0062 0.3895 0.064 Uiso calc R 1
H H14B 0.5676 1.1669 0.3655 0.064 Uiso calc R 1
H H14C 0.5736 0.9478 0.2690 0.064 Uiso calc R 1
C C15 0.95677(9) -0.0466(4) 0.3035(3) 0.0538(5) Uani d . 1
H H15A 0.9593 -0.0207 0.4075 0.081 Uiso calc R 1
H H15B 0.9942 -0.0649 0.2664 0.081 Uiso calc R 1
H H15C 0.9350 -0.1820 0.2838 0.081 Uiso calc R 1
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
C11 N1 N2 118.32(12)
C11 N1 H1 121.1(13)
N2 N1 H1 118.2(13)
C12 N2 N1 115.58(13)
C6 O2 C15 117.03(15)
C2 C1 C10 118.95(14)
C2 C1 C11 122.73(13)
C10 C1 C11 118.26(12)
C1 C2 C3 121.09(13)
C1 C2 H2 119.5
C3 C2 H2 119.5
C2 C3 C8 119.83(12)
C2 C3 C4 121.29(13)
C8 C3 C4 118.87(13)
C5 C4 C3 120.66(14)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.35(15)
C4 C5 H5 119.8
C6 C5 H5 119.8
O2 C6 C7 125.58(15)
O2 C6 C5 113.48(14)
C7 C6 C5 120.94(14)
C6 C7 C8 119.49(14)
C6 C7 H7 120.3
C8 C7 H7 120.3
C3 C8 C7 119.61(13)
C3 C8 C9 118.25(13)
C7 C8 C9 122.13(13)
C10 C9 C8 120.66(13)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C1 121.18(13)
C9 C10 H10 119.4
C1 C10 H10 119.4
O1 C11 N1 123.28(15)
O1 C11 C1 120.72(14)
N1 C11 C1 115.98(12)
N2 C12 C14 126.69(15)
N2 C12 C13 116.84(16)
C14 C12 C13 116.47(16)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O2 C15 H15A 109.5
O2 C15 H15B 109.5
H15A C15 H15B 109.5
O2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.355(2)
N1 N2 1.4017(18)
N1 H1 0.88(2)
N2 C12 1.286(2)
O1 C11 1.2352(19)
O2 C6 1.3733(19)
O2 C15 1.434(2)
C1 C2 1.385(2)
C1 C10 1.426(2)
C1 C11 1.502(2)
C2 C3 1.419(2)
C2 H2 0.9500
C3 C8 1.4245(18)
C3 C4 1.432(2)
C4 C5 1.364(2)
C4 H4 0.9500
C5 C6 1.424(2)
C5 H5 0.9500
C6 C7 1.380(2)
C7 C8 1.431(2)
C7 H7 0.9500
C8 C9 1.431(2)
C9 C10 1.376(2)
C9 H9 0.9500
C10 H10 0.9500
C12 C14 1.496(3)
C12 C13 1.496(2)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
N1 H1 O1 2_564 0.88(2) 1.98(2) 2.8222(17) 161.3(19)
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
C11 N1 N2 C12 164.11(15)
C10 C1 C2 C3 -0.6(2)
C11 C1 C2 C3 176.83(12)
C1 C2 C3 C8 -1.0(2)
C1 C2 C3 C4 179.63(15)
C2 C3 C4 C5 178.74(14)
C8 C3 C4 C5 -0.7(2)
C3 C4 C5 C6 -1.7(3)
C15 O2 C6 C7 -7.3(3)
C15 O2 C6 C5 172.53(17)
C4 C5 C6 O2 -177.47(15)
C4 C5 C6 C7 2.3(3)
O2 C6 C7 C8 179.27(14)
C5 C6 C7 C8 -0.5(2)
C2 C3 C8 C7 -176.96(13)
C4 C3 C8 C7 2.4(2)
C2 C3 C8 C9 2.07(19)
C4 C3 C8 C9 -178.54(15)
C6 C7 C8 C3 -1.9(2)
C6 C7 C8 C9 179.15(14)
C3 C8 C9 C10 -1.6(2)
C7 C8 C9 C10 177.36(13)
C8 C9 C10 C1 0.1(2)
C2 C1 C10 C9 1.0(2)
C11 C1 C10 C9 -176.49(13)
N2 N1 C11 O1 -4.0(2)
N2 N1 C11 C1 177.15(14)
C2 C1 C11 O1 -157.24(15)
C10 C1 C11 O1 20.2(2)
C2 C1 C11 N1 21.6(2)
C10 C1 C11 N1 -160.97(13)
N1 N2 C12 C14 -2.2(3)
N1 N2 C12 C13 177.68(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124009
