#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/96/2239644.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_2239644
loop_
_publ_author_name
'Narayana, B.'
'Nayak, Prakash S.'
'Sarojini, Balladka K.'
'Jasinski, Jerry P.'
_publ_section_title
;
 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid
;
_journal_coeditor_code           ZL2589
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o752
_journal_page_last               o753
_journal_paper_doi               10.1107/S1600536814012562
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H13 N O4'
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_chemical_name_common
;
4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid
;
_chemical_name_systematic
;
4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                92.833(6)
_cell_angle_beta                 90.315(7)
_cell_angle_gamma                96.222(7)
_cell_formula_units_Z            2
_cell_length_a                   5.0164(5)
_cell_length_b                   5.2908(4)
_cell_length_c                   21.8464(18)
_cell_measurement_reflns_used    1583
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.2450
_cell_measurement_theta_min      6.0840
_cell_volume                     575.67(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus et al., 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Agilent Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3374
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.245
_diffrn_reflns_theta_min         4.052
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0796P)²+0.1341P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                1934
_reflns_number_total             2168
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2589sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        575.67(8)
_cod_database_code               2239644
_cod_database_fobs_code          2239644
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
O O1 0.3166(2) 0.3573(2) 0.70834(5) 0.0287(3) Uani d 1
O O2 0.2328(3) 0.2934(2) 0.51283(6) 0.0333(3) Uani d 1
O O3 0.3843(3) 0.6459(2) 0.56835(6) 0.0322(3) Uani d 1
H H3 0.529(9) 0.681(8) 0.540(2) 0.117(15) Uiso d 1
O O4 1.3191(3) 1.1439(2) 0.91390(6) 0.0347(3) Uani d 1
N N1 0.3525(3) 0.7850(2) 0.72813(6) 0.0238(3) Uani d 1
H H1 0.2927 0.9262 0.7169 0.029 Uiso calc 1
C C1 0.2405(3) 0.5648(3) 0.70006(7) 0.0212(3) Uani d 1
C C2 0.0055(3) 0.5917(3) 0.65734(7) 0.0236(3) Uani d 1
H H2A -0.1643 0.5631 0.6801 0.028 Uiso calc 1
H H2B 0.0205 0.7669 0.6428 0.028 Uiso calc 1
C C3 -0.0012(3) 0.4045(3) 0.60311(7) 0.0230(3) Uani d 1
C C4 0.2171(3) 0.4458(3) 0.55784(7) 0.0235(3) Uani d 1
C C5 -0.1886(4) 0.2087(3) 0.59389(8) 0.0302(4) Uani d 1
H H5A -0.335(4) 0.171(4) 0.6228(10) 0.030(5) Uiso d 1
H H5B -0.180(5) 0.095(5) 0.5563(12) 0.051(7) Uiso d 1
C C6 0.5569(3) 0.8108(3) 0.77393(7) 0.0216(3) Uani d 1
C C7 0.7359(3) 1.0308(3) 0.77582(8) 0.0257(4) Uani d 1
H H7 0.7233 1.1541 0.7461 0.031 Uiso calc 1
C C8 0.9319(3) 1.0702(3) 0.82088(8) 0.0254(4) Uani d 1
H H8 1.0534 1.2211 0.8218 0.030 Uiso calc 1
C C9 0.9549(3) 0.8921(3) 0.86518(7) 0.0223(3) Uani d 1
C C10 0.7744(3) 0.6724(3) 0.86265(7) 0.0255(4) Uani d 1
H H10 0.7873 0.5488 0.8923 0.031 Uiso calc 1
C C11 0.5764(3) 0.6305(3) 0.81778(8) 0.0255(4) Uani d 1
H H11 0.4545 0.4799 0.8168 0.031 Uiso calc 1
C C12 1.1696(3) 0.9468(3) 0.91332(7) 0.0253(4) Uani d 1
C C13 1.1922(4) 0.7541(3) 0.96093(8) 0.0343(4) Uani d 1
H H13A 1.2316 0.5927 0.9409 0.051 Uiso calc 1
H H13B 1.0227 0.7275 0.9830 0.051 Uiso calc 1
H H13C 1.3371 0.8164 0.9899 0.051 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 O3 H3 118(2)
C1 N1 H1 116.8
C1 N1 C6 126.47(13)
C6 N1 H1 116.8
O1 C1 N1 123.53(14)
O1 C1 C2 121.41(14)
N1 C1 C2 115.05(13)
C1 C2 H2A 109.4
C1 C2 H2B 109.4
H2A C2 H2B 108.0
C3 C2 C1 111.32(12)
C3 C2 H2A 109.4
C3 C2 H2B 109.4
C4 C3 C2 116.83(14)
C5 C3 C2 123.91(15)
C5 C3 C4 119.26(15)
O2 C4 O3 123.36(16)
O2 C4 C3 120.94(15)
O3 C4 C3 115.70(14)
C3 C5 H5A 122.5(13)
C3 C5 H5B 118.9(15)
H5A C5 H5B 118.5(19)
C7 C6 N1 117.63(14)
C7 C6 C11 119.68(15)
C11 C6 N1 122.63(14)
C6 C7 H7 120.0
C8 C7 C6 120.04(15)
C8 C7 H7 120.0
C7 C8 H8 119.4
C7 C8 C9 121.16(15)
C9 C8 H8 119.4
C8 C9 C12 118.71(15)
C10 C9 C8 118.15(15)
C10 C9 C12 123.14(14)
C9 C10 H10 119.3
C11 C10 C9 121.32(15)
C11 C10 H10 119.3
C6 C11 H11 120.2
C10 C11 C6 119.64(15)
C10 C11 H11 120.2
O4 C12 C9 120.33(15)
O4 C12 C13 121.36(16)
C9 C12 C13 118.30(14)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.222(2)
O2 C4 1.249(2)
O3 H3 0.97(5)
O3 C4 1.288(2)
O4 C12 1.216(2)
N1 H1 0.8800
N1 C1 1.354(2)
N1 C6 1.420(2)
C1 C2 1.523(2)
C2 H2A 0.9900
C2 H2B 0.9900
C2 C3 1.504(2)
C3 C4 1.485(2)
C3 C5 1.328(2)
C5 H5A 0.98(2)
C5 H5B 1.00(3)
C6 C7 1.389(2)
C6 C11 1.395(2)
C7 H7 0.9500
C7 C8 1.380(2)
C8 H8 0.9500
C8 C9 1.397(2)
C9 C10 1.392(2)
C9 C12 1.497(2)
C10 H10 0.9500
C10 C11 1.385(2)
C11 H11 0.9500
C12 C13 1.504(2)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 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
O3 H3 O2 2_666 0.97(5) 1.66(5) 2.6262(17) 174(4)
N1 H1 O1 1_565 0.88 2.29 3.1039(17) 154.2
C5 H5B O2 2_556 1.00(3) 2.48(3) 3.434(2) 160(2)
C7 H7 O1 1_565 0.95 2.56 3.254(2) 130.3
C13 H13A O4 1_545 0.98 2.50 3.465(2) 166.9
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
O1 C1 C2 C3 -35.3(2)
N1 C1 C2 C3 145.67(14)
N1 C6 C7 C8 177.47(14)
N1 C6 C11 C10 -177.45(14)
C1 N1 C6 C7 148.44(16)
C1 N1 C6 C11 -34.2(2)
C1 C2 C3 C4 -68.77(17)
C1 C2 C3 C5 111.34(18)
C2 C3 C4 O2 177.03(14)
C2 C3 C4 O3 -3.0(2)
C5 C3 C4 O2 -3.1(2)
C5 C3 C4 O3 176.90(15)
C6 N1 C1 O1 -5.0(3)
C6 N1 C1 C2 174.03(14)
C6 C7 C8 C9 0.0(3)
C7 C6 C11 C10 -0.1(2)
C7 C8 C9 C10 0.1(2)
C7 C8 C9 C12 -179.32(14)
C8 C9 C10 C11 -0.2(2)
C8 C9 C12 O4 0.6(2)
C8 C9 C12 C13 179.84(15)
C9 C10 C11 C6 0.2(3)
C10 C9 C12 O4 -178.79(16)
C10 C9 C12 C13 0.4(2)
C11 C6 C7 C8 0.0(2)
C12 C9 C10 C11 179.19(14)
