#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/87/2018750.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_2018750
loop_
_publ_author_name
'Ilangovan, Andivelu'
'Venkatesan, Perumal'
'Ganesh Kumar, Rajendran'
_publ_section_title
;
 Hydrogen bonding due to regioisomerism and its effect on the
 supramolecular architecture of diethyl
 2-[(2/4-hydroxyanilino)methylidene]malonates
;
_journal_coeditor_code           FN3116
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              70
_journal_page_last               73
_journal_paper_doi               10.1107/S0108270112047257
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C14 H17 N O5'
_chemical_formula_moiety         'C14 H17 N O5'
_chemical_formula_sum            'C14 H17 N O5'
_chemical_formula_weight         279.29
_chemical_name_systematic
;
Diethyl 2-[(2-hydroxyanilino)methylidene]malonate
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3011(3)
_cell_length_b                   19.2760(4)
_cell_length_c                   6.6725(2)
_cell_measurement_reflns_used    2008
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.22
_cell_measurement_theta_min      3.05
_cell_volume                     1453.54(7)
_computing_cell_refinement       'SMART (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7641
_diffrn_reflns_theta_full        26.77
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.203
_refine_ls_extinction_coef       0.0072(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0487
_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)+(0.0764P)²+0.2553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1165
_reflns_number_total             1690
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fn3116.cif
_cod_data_source_block           I
_cod_database_code               2018750
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, z'
'x, -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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.93175(16) 0.39737(8) 0.2500 0.0719(6) Uani d S 1 2 . .
O O4 1.12614(17) 0.24764(10) 0.2500 0.0973(8) Uani d S 1 2 . .
O O5 1.20132(18) 0.14140(9) 0.2500 0.1018(8) Uani d S 1 2 . .
O O3 0.86035(15) 0.06136(8) 0.2500 0.0689(5) Uani d S 1 2 . .
O O2 1.05136(16) 0.03504(7) 0.2500 0.0770(6) Uani d S 1 2 . .
N N1 0.8942(2) 0.26400(9) 0.2500 0.0609(6) Uani d S 1 2 . .
C C1 0.7941(2) 0.30708(11) 0.2500 0.0571(6) Uani d S 1 2 . .
C C2 0.8167(2) 0.37835(11) 0.2500 0.0573(6) Uani d S 1 2 . .
C C3 0.7241(3) 0.42457(14) 0.2500 0.0724(8) Uani d S 1 2 . .
H H3 0.7390 0.4720 0.2500 0.087 Uiso calc SR 1 2 . .
C C4 0.6101(3) 0.40078(16) 0.2500 0.0918(10) Uani d S 1 2 . .
H H4 0.5475 0.4321 0.2500 0.110 Uiso calc SR 1 2 . .
C C5 0.5875(3) 0.33043(17) 0.2500 0.0931(10) Uani d S 1 2 . .
H H5 0.5098 0.3145 0.2500 0.112 Uiso calc SR 1 2 . .
C C6 0.6789(3) 0.28407(14) 0.2500 0.0749(8) Uani d S 1 2 . .
H H6 0.6632 0.2367 0.2500 0.090 Uiso calc SR 1 2 . .
C C7 0.8954(2) 0.19499(11) 0.2500 0.0572(6) Uani d S 1 2 A .
C C8 0.9933(2) 0.15357(10) 0.2500 0.0584(6) Uani d S 1 2 . .
C C12 1.1103(3) 0.18519(12) 0.2500 0.0737(8) Uani d S 1 2 A .
C C13 1.3185(3) 0.17212(17) 0.2500 0.159(2) Uani d S 1 2 A 1
H H13A 1.3277 0.2012 0.1323 0.191 Uiso calc PR 0.50 1 A 1
H H13B 1.3277 0.2012 0.3677 0.191 Uiso calc PR 0.50 1 A 1
C C14 1.4055(3) 0.1209(2) 0.2500 0.1268(15) Uani d S 1 2 . .
H H14A 1.3874 0.0869 0.3504 0.190 Uiso calc PR 0.50 1 A 1
H H14B 1.4810 0.1415 0.2787 0.190 Uiso calc PR 0.50 1 A 1
H H14C 1.4082 0.0990 0.1208 0.190 Uiso calc PR 0.50 1 A 1
C C9 0.9745(2) 0.07839(11) 0.2500 0.0569(6) Uani d S 1 2 A 1
C C10 0.8306(2) -0.01136(12) 0.2500 0.0701(7) Uani d S 1 2 A 1
H H10A 0.8627 -0.0339 0.3680 0.084 Uiso calc PR 0.50 1 A 1
H H10B 0.8627 -0.0339 0.1320 0.084 Uiso calc PR 0.50 1 A 1
C C11 0.6988(3) -0.01584(16) 0.2500 0.0891(9) Uani d S 1 2 A 1
H H11A 0.6752 -0.0637 0.2500 0.134 Uiso calc SR 1 2 A 1
H H11B 0.6682 0.0066 0.1325 0.134 Uiso calc PR 0.50 1 A 1
H H11C 0.6682 0.0066 0.3675 0.134 Uiso calc PR 0.50 1 A 1
H H1O 0.939(3) 0.4416(19) 0.2500 0.112(11) Uiso d S 1 2 B 1
H H1N 0.963(3) 0.2803(13) 0.2500 0.075(9) Uiso d S 1 2 C 1
H H7 0.818(2) 0.1746(12) 0.2500 0.055(6) Uiso d S 1 2 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
C2 O1 H1O . . 111(2)
C12 O5 C13 . 6_556 116.5(2)
C12 O5 C13 . . 116.5(2)
C13 O5 C13 6_556 . 0.0(2)
C9 O3 C10 . . 117.77(19)
C7 N1 C1 . . 126.8(2)
C7 N1 H1N . . 111.4(18)
C1 N1 H1N . . 121.7(18)
C6 C1 C2 . . 119.4(2)
C6 C1 N1 . . 124.9(2)
C2 C1 N1 . . 115.7(2)
O1 C2 C3 . . 123.8(2)
O1 C2 C1 . . 116.3(2)
C3 C2 C1 . . 119.9(2)
C4 C3 C2 . . 120.0(3)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C3 C4 C5 . . 120.2(3)
C3 C4 H4 . . 119.9
C5 C4 H4 . . 119.9
C6 C5 C4 . . 120.2(3)
C6 C5 H5 . . 119.9
C4 C5 H5 . . 119.9
C5 C6 C1 . . 120.3(2)
C5 C6 H6 . . 119.8
C1 C6 H6 . . 119.8
N1 C7 C8 . . 126.4(2)
N1 C7 H7 . . 113.6(14)
C8 C7 H7 . . 120.0(14)
C7 C8 C12 . . 119.4(2)
C7 C8 C9 . . 117.5(2)
C12 C8 C9 . . 123.1(2)
O4 C12 O5 . . 120.9(3)
O4 C12 C8 . . 123.2(3)
O5 C12 C8 . . 115.9(2)
C14 C13 O5 . . 110.8(3)
C14 C13 H13A . . 109.5
O5 C13 H13A . . 109.5
C14 C13 H13B . . 109.5
O5 C13 H13B . . 109.5
H13A C13 H13B . . 108.1
O2 C9 O3 . . 121.8(2)
O2 C9 C8 . . 125.6(2)
O3 C9 C8 . . 112.6(2)
O3 C10 C11 . . 106.8(2)
O3 C10 H10A . . 110.4
C11 C10 H10A . . 110.4
O3 C10 H10B . . 110.4
C11 C10 H10B . . 110.4
H10A C10 H10B . . 108.6
C10 C11 H11A . . 109.5
C10 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C10 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.351(3)
O1 H1O . 0.86(4)
O4 C12 . 1.217(3)
O5 C12 . 1.331(3)
O5 C13 6_556 1.451(4)
O5 C13 . 1.451(4)
O3 C9 . 1.331(3)
O3 C10 . 1.442(3)
O2 C9 . 1.205(3)
N1 C7 . 1.330(3)
N1 C1 . 1.404(3)
N1 H1N . 0.84(3)
C1 C6 . 1.375(4)
C1 C2 . 1.398(3)
C2 C3 . 1.374(3)
C3 C4 . 1.368(4)
C3 H3 . 0.9300
C4 C5 . 1.380(4)
C4 H4 . 0.9300
C5 C6 . 1.366(4)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 C8 . 1.364(3)
C7 H7 . 0.96(2)
C8 C12 . 1.456(4)
C8 C9 . 1.465(3)
C13 C14 . 1.393(5)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C10 C11 . 1.492(4)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
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 H1N O1 . 0.84(3) 2.28(3) 2.606(2) 103(2)
N1 H1N O4 . 0.84(3) 1.95(3) 2.640(3) 139(2)
O1 H1O O2 7_765 0.86(4) 1.81(4) 2.661(2) 178(3)
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
C7 N1 C1 C6 . 0.0
C7 N1 C1 C2 . 180.0
C6 C1 C2 O1 . 180.0
N1 C1 C2 O1 . 0.0
C6 C1 C2 C3 . 0.0
N1 C1 C2 C3 . 180.0
O1 C2 C3 C4 . 180.0
C1 C2 C3 C4 . 0.0
C2 C3 C4 C5 . 0.0
C3 C4 C5 C6 . 0.0
C4 C5 C6 C1 . 0.0
C2 C1 C6 C5 . 0.0
N1 C1 C6 C5 . 180.0
C1 N1 C7 C8 . 180.0
N1 C7 C8 C12 . 0.0
N1 C7 C8 C9 . 180.0
C13 O5 C12 O4 6_556 0.0
C13 O5 C12 O4 . 0.0
C13 O5 C12 C8 6_556 180.0
C13 O5 C12 C8 . 180.0
C7 C8 C12 O4 . 0.0
C9 C8 C12 O4 . 180.0
C7 C8 C12 O5 . 180.0
C9 C8 C12 O5 . 0.0
C12 O5 C13 C14 . 180.0
C13 O5 C13 C14 6_556 0E1(10)
C10 O3 C9 O2 . 0.0
C10 O3 C9 C8 . 180.0
C7 C8 C9 O2 . 180.0
C12 C8 C9 O2 . 0.0
C7 C8 C9 O3 . 0.0
C12 C8 C9 O3 . 180.0
C9 O3 C10 C11 . 180.0
