#------------------------------------------------------------------------------
#$Date: 2018-09-27 07:13:35 +0300 (Thu, 27 Sep 2018) $
#$Revision: 211196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/05/2220523.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_2220523
loop_
_publ_author_name
'Natale, Nicholas R.'
'Szabon-Watola, Monica I.'
'Twamley, Brendan'
'Bridges, Richard J.'
'Patel, Sarjubhai'
'Rajale, Trideep'
_publ_section_title
;Ethyl
 4-{1-[(2,4-dinitrophenyl)hydrazono]ethyl}-5-(2-naphthylmethoxymethyl)isoxazole-3-carboxylate
;
_journal_coeditor_code           HG2449
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o144
_journal_page_last               o145
_journal_paper_doi               10.1107/S1600536808041901
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C26 H23 N5 O8'
_chemical_formula_moiety         'C26 H23 N5 O8'
_chemical_formula_sum            'C26 H23 N5 O8'
_chemical_formula_weight         533.49
_chemical_name_systematic
;
Ethyl 4-{1-[(2,4-dinitrophenyl)hydrazono]ethyl}-
5-(2-naphthylmethoxymethyl)isoxazole-3-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.5810(10)
_cell_angle_beta                 95.925(2)
_cell_angle_gamma                99.251(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0839(6)
_cell_length_b                   12.1760(10)
_cell_length_c                   14.184(2)
_cell_measurement_reflns_used    6135
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.25
_cell_volume                     1200.6(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'XL in SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'XS in SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18560
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0350
_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)+(0.0462P)²+0.5022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                4009
_reflns_number_total             4357
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2449.cif
_cod_data_source_block           I
_cod_original_cell_volume        1200.7(2)
_cod_database_code               2220523
_cod_database_fobs_code          2220523
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.86385(19) 0.87869(12) 0.65591(10) 0.0225(3) Uani d . 1 . .
H H1A 0.8404 0.9531 0.6498 0.027 Uiso calc R 1 . .
C C2 0.9219(2) 0.84176(12) 0.74301(10) 0.0243(3) Uani d . 1 . .
H H2A 0.9396 0.8910 0.7967 0.029 Uiso calc R 1 . .
C C3 0.95619(18) 0.73084(12) 0.75441(10) 0.0223(3) Uani d . 1 . .
C C4 1.0160(2) 0.68877(14) 0.84368(10) 0.0279(3) Uani d . 1 . .
H H4A 1.0362 0.7363 0.8985 0.034 Uiso calc R 1 . .
C C5 1.0451(2) 0.58036(14) 0.85179(11) 0.0300(4) Uani d . 1 . .
H H5A 1.0835 0.5532 0.9121 0.036 Uiso calc R 1 . .
C C6 1.01822(19) 0.50944(13) 0.77116(11) 0.0272(3) Uani d . 1 . .
H H6A 1.0391 0.4346 0.7772 0.033 Uiso calc R 1 . .
C C7 0.96224(19) 0.54760(12) 0.68412(10) 0.0230(3) Uani d . 1 . .
H H7A 0.9457 0.4990 0.6301 0.028 Uiso calc R 1 . .
C C8 0.92856(18) 0.65841(11) 0.67329(10) 0.0199(3) Uani d . 1 . .
C C9 0.86964(18) 0.69966(11) 0.58372(9) 0.0186(3) Uani d . 1 . .
H H9A 0.8517 0.6517 0.5292 0.022 Uiso calc R 1 . .
C C10 0.83807(18) 0.80712(11) 0.57424(9) 0.0187(3) Uani d . 1 . .
C C12 0.78057(19) 0.85335(11) 0.47991(9) 0.0199(3) Uani d . 1 . .
H H12A 0.6616 0.8857 0.4827 0.024 Uiso calc R 1 . .
H H12B 0.8835 0.9130 0.4636 0.024 Uiso calc R 1 . .
O O13 0.74889(14) 0.76632(8) 0.40973(7) 0.0234(2) Uani d . 1 . .
C C14 0.7541(2) 0.80387(11) 0.31558(9) 0.0210(3) Uani d . 1 . .
H H14A 0.8040 0.7487 0.2772 0.025 Uiso calc R 1 . .
H H14B 0.8446 0.8749 0.3162 0.025 Uiso calc R 1 . .
C C15 0.56224(19) 0.82104(11) 0.26945(9) 0.0183(3) Uani d . 1 . .
O O16 0.50754(14) 0.92145(7) 0.28170(7) 0.0218(2) Uani d . 1 . .
N N17 0.32990(17) 0.92234(9) 0.22939(8) 0.0214(3) Uani d . 1 . .
C C18 0.28435(19) 0.82377(11) 0.18738(9) 0.0178(3) Uani d . 1 . .
C C19 0.09928(19) 0.79318(11) 0.12615(9) 0.0183(3) Uani d . 1 . .
O O20 0.04690(14) 0.70128(8) 0.09134(7) 0.0255(2) Uani d . 1 . .
O O21 0.00088(13) 0.87728(8) 0.11528(7) 0.0221(2) Uani d . 1 . .
C C22 -0.1807(2) 0.85128(12) 0.05412(10) 0.0248(3) Uani d . 1 . .
H H22A -0.2644 0.7876 0.0792 0.030 Uiso calc R 1 . .
H H22B -0.1561 0.8310 -0.0107 0.030 Uiso calc R 1 . .
C C23 -0.2763(2) 0.95228(13) 0.05216(11) 0.0303(3) Uani d . 1 . .
H H23A -0.3983 0.9371 0.0112 0.045 Uiso calc R 1 . .
H H23B -0.1922 1.0148 0.0274 0.045 Uiso calc R 1 . .
H H23C -0.3012 0.9712 0.1166 0.045 Uiso calc R 1 . .
C C24 0.42658(18) 0.75465(11) 0.21070(9) 0.0166(3) Uani d . 1 . .
C C25 0.43276(18) 0.63811(11) 0.18367(9) 0.0163(3) Uani d . 1 . .
C C26 0.4029(2) 0.59917(11) 0.08182(9) 0.0211(3) Uani d . 1 . .
H H26A 0.2937 0.5381 0.0727 0.032 Uiso calc R 1 . .
H H26B 0.5190 0.5731 0.0647 0.032 Uiso calc R 1 . .
H H26C 0.3763 0.6609 0.0414 0.032 Uiso calc R 1 . .
N N27 0.47840(15) 0.57795(9) 0.25405(8) 0.0166(2) Uani d . 1 . .
N N28 0.49202(15) 0.47000(9) 0.23163(8) 0.0169(2) Uani d . 1 . .
H H28A 0.4652 0.4444 0.1727 0.020 Uiso calc R 1 . .
C C29 0.54745(17) 0.40296(10) 0.30165(9) 0.0159(3) Uani d . 1 . .
C C30 0.56433(18) 0.29033(10) 0.28470(9) 0.0165(3) Uani d . 1 . .
C C31 0.62357(18) 0.22374(11) 0.35731(10) 0.0179(3) Uani d . 1 . .
H H31A 0.6335 0.1482 0.3449 0.022 Uiso calc R 1 . .
C C32 0.66733(18) 0.26928(11) 0.44716(9) 0.0184(3) Uani d . 1 . .
C C33 0.65367(18) 0.37992(11) 0.46714(9) 0.0186(3) Uani d . 1 . .
H H33A 0.6844 0.4096 0.5301 0.022 Uiso calc R 1 . .
C C34 0.59579(18) 0.44555(11) 0.39560(9) 0.0180(3) Uani d . 1 . .
H H34A 0.5880 0.5211 0.4093 0.022 Uiso calc R 1 . .
N N35 0.52605(15) 0.23912(9) 0.19029(8) 0.0186(2) Uani d . 1 . .
O O36 0.56216(15) 0.14538(8) 0.17852(7) 0.0263(2) Uani d . 1 . .
O O37 0.45844(14) 0.29207(8) 0.12397(7) 0.0222(2) Uani d . 1 . .
N N38 0.73724(16) 0.20206(10) 0.52367(8) 0.0215(3) Uani d . 1 . .
O O39 0.79957(15) 0.24887(9) 0.60029(7) 0.0288(2) Uani d . 1 . .
O O40 0.73174(15) 0.10215(8) 0.50788(8) 0.0292(2) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 120.75(13) ?
C2 C1 H1A . . 119.6 ?
C10 C1 H1A . . 119.6 ?
C1 C2 C3 . . 120.89(13) ?
C1 C2 H2A . . 119.6 ?
C3 C2 H2A . . 119.6 ?
C2 C3 C4 . . 122.80(13) ?
C2 C3 C8 . . 118.70(13) ?
C4 C3 C8 . . 118.50(13) ?
C5 C4 C3 . . 120.92(14) ?
C5 C4 H4A . . 119.5 ?
C3 C4 H4A . . 119.5 ?
C4 C5 C6 . . 120.20(14) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C7 C6 C5 . . 120.32(14) ?
C7 C6 H6A . . 119.8 ?
C5 C6 H6A . . 119.8 ?
C6 C7 C8 . . 121.02(14) ?
C6 C7 H7A . . 119.5 ?
C8 C7 H7A . . 119.5 ?
C7 C8 C9 . . 121.98(13) ?
C7 C8 C3 . . 119.02(13) ?
C9 C8 C3 . . 118.99(13) ?
C10 C9 C8 . . 121.36(12) ?
C10 C9 H9A . . 119.3 ?
C8 C9 H9A . . 119.3 ?
C9 C10 C1 . . 119.31(12) ?
C9 C10 C12 . . 122.27(12) ?
C1 C10 C12 . . 118.41(12) ?
O13 C12 C10 . . 109.06(10) ?
O13 C12 H12A . . 109.9 ?
C10 C12 H12A . . 109.9 ?
O13 C12 H12B . . 109.9 ?
C10 C12 H12B . . 109.9 ?
H12A C12 H12B . . 108.3 ?
C14 O13 C12 . . 114.09(10) ?
O13 C14 C15 . . 113.35(11) ?
O13 C14 H14A . . 108.9 ?
C15 C14 H14A . . 108.9 ?
O13 C14 H14B . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
O16 C15 C24 . . 109.91(11) ?
O16 C15 C14 . . 118.15(11) ?
C24 C15 C14 . . 131.86(12) ?
C15 O16 N17 . . 109.21(10) ?
C18 N17 O16 . . 105.26(10) ?
N17 C18 C24 . . 112.27(12) ?
N17 C18 C19 . . 120.58(12) ?
C24 C18 C19 . . 127.11(12) ?
O20 C19 O21 . . 124.76(12) ?
O20 C19 C18 . . 122.48(12) ?
O21 C19 C18 . . 112.76(11) ?
C19 O21 C22 . . 114.54(11) ?
O21 C22 C23 . . 107.90(12) ?
O21 C22 H22A . . 110.1 ?
C23 C22 H22A . . 110.1 ?
O21 C22 H22B . . 110.1 ?
C23 C22 H22B . . 110.1 ?
H22A C22 H22B . . 108.4 ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C15 C24 C18 . . 103.34(11) ?
C15 C24 C25 . . 125.47(12) ?
C18 C24 C25 . . 131.16(12) ?
N27 C25 C24 . . 113.88(11) ?
N27 C25 C26 . . 124.68(12) ?
C24 C25 C26 . . 121.28(11) ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C25 N27 N28 . . 115.76(11) ?
C29 N28 N27 . . 119.06(11) ?
C29 N28 H28A . . 120.5 ?
N27 N28 H28A . . 120.5 ?
N28 C29 C34 . . 120.13(11) ?
N28 C29 C30 . . 122.70(12) ?
C34 C29 C30 . . 117.16(12) ?
C31 C30 C29 . . 121.66(12) ?
C31 C30 N35 . . 116.43(11) ?
C29 C30 N35 . . 121.90(11) ?
C32 C31 C30 . . 118.64(12) ?
C32 C31 H31A . . 120.7 ?
C30 C31 H31A . . 120.7 ?
C31 C32 C33 . . 121.72(12) ?
C31 C32 N38 . . 119.48(12) ?
C33 C32 N38 . . 118.76(12) ?
C34 C33 C32 . . 119.63(12) ?
C34 C33 H33A . . 120.2 ?
C32 C33 H33A . . 120.2 ?
C33 C34 C29 . . 121.19(12) ?
C33 C34 H34A . . 119.4 ?
C29 C34 H34A . . 119.4 ?
O36 N35 O37 . . 122.13(11) ?
O36 N35 C30 . . 118.81(11) ?
O37 N35 C30 . . 119.06(10) ?
O39 N38 O40 . . 123.59(11) ?
O39 N38 C32 . . 118.01(11) ?
O40 N38 C32 . . 118.39(11) ?
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
C1 C2 . 1.365(2) ?
C1 C10 . 1.4210(19) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.418(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.420(2) ?
C3 C8 . 1.420(2) ?
C4 C5 . 1.373(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.404(2) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.366(2) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.415(2) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.4182(19) ?
C9 C10 . 1.3682(19) ?
C9 H9A . 0.9500 ?
C10 C12 . 1.4998(18) ?
C12 O13 . 1.4214(16) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
O13 C14 . 1.4181(16) ?
C14 C15 . 1.4930(19) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 O16 . 1.3554(16) ?
C15 C24 . 1.3575(19) ?
O16 N17 . 1.3950(15) ?
N17 C18 . 1.3120(17) ?
C18 C24 . 1.4291(18) ?
C18 C19 . 1.4876(19) ?
C19 O20 . 1.2047(16) ?
C19 O21 . 1.3300(16) ?
O21 C22 . 1.4628(16) ?
C22 C23 . 1.496(2) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 C25 . 1.4749(18) ?
C25 N27 . 1.2893(17) ?
C25 C26 . 1.4991(18) ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
N27 N28 . 1.3700(15) ?
N28 C29 . 1.3587(17) ?
N28 H28A . 0.8800 ?
C29 C34 . 1.4130(19) ?
C29 C30 . 1.4160(18) ?
C30 C31 . 1.3898(18) ?
C30 N35 . 1.4524(17) ?
C31 C32 . 1.3699(19) ?
C31 H31A . 0.9500 ?
C32 C33 . 1.3945(19) ?
C32 N38 . 1.4596(17) ?
C33 C34 . 1.3684(18) ?
C33 H33A . 0.9500 ?
C34 H34A . 0.9500 ?
N35 O36 . 1.2227(14) ?
N35 O37 . 1.2443(14) ?
N38 O39 . 1.2282(15) ?
N38 O40 . 1.2284(15) ?
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
N28 H28A O37 . 0.88 1.96 2.6028(14) 128
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741395
