##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Dimethyl 2-[(acridin-9-yl)methylidene]malonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H15 N O4'
_chemical_formula_sum     'C19 H15 N O4'
_chemical_formula_iupac     'C19 H15 N O4'
_chemical_formula_weight     321.32
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.3022(2)
_cell_length_b     9.0208(3)
_cell_length_c     12.0334(4)
_cell_angle_alpha     96.468(2)
_cell_angle_beta     93.652(2)
_cell_angle_gamma     117.422(2)
_cell_volume     787.98(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6418
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.354
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     336
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     295
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enraf Nonius FR590'
_diffrn_radiation_monochromator     'horizonally mounted graphite crystal'
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     'CCD rotation images,thick slices'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     10674
_diffrn_reflns_av_R_equivalents     0.0498
_diffrn_reflns_av_sigmaI/netI     0.0372
_diffrn_reflns_theta_min     2.58
_diffrn_reflns_theta_max     27.51
_diffrn_reflns_theta_full     27.51
_diffrn_measured_fraction_theta_max     0.972
_diffrn_measured_fraction_theta_full     0.972
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3626
_reflns_number_gt     2805
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0630
_refine_ls_R_factor_gt     0.0515
_refine_ls_wR_factor_gt     0.1344
_refine_ls_wR_factor_ref     0.1479
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     3626
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0817P)^2^+0.1056P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.261
_refine_diff_density_min     -0.244
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.168(19)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
_computing_data_collection     'COLLECT (Nonius, 1997)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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
    C C2 0.18856(17) -0.04107(16) 0.05238(10) 0.0416(3) Uani d . 1 1 . .
    C C8 0.27051(18) 0.29435(17) 0.10755(11) 0.0439(3) Uani d . 1 1 . .
    C C1 0.12960(17) 0.00751(16) 0.15015(10) 0.0409(3) Uani d . 1 1 . .
    C C16 0.25132(19) -0.00447(18) 0.38809(12) 0.0475(3) Uani d . 1 1 . .
    N N1 0.32779(16) 0.24918(14) 0.01345(9) 0.0477(3) Uani d . 1 1 . .
    C C14 0.02296(18) -0.12607(17) 0.21649(11) 0.0455(3) Uani d . 1 1 . .
    H H14 -0.0906 -0.2111 0.1815 0.055 Uiso calc R 1 1 . .
    O O4 -0.19557(15) -0.38893(13) 0.31911(9) 0.0630(3) Uani d . 1 1 . .
    C C13 0.16978(17) 0.17719(16) 0.17992(10) 0.0412(3) Uani d . 1 1 . .
    C C12 0.11370(19) 0.24024(18) 0.27615(11) 0.0484(3) Uani d . 1 1 . .
    H H12 0.0464 0.1665 0.3236 0.058 Uiso calc R 1 1 . .
    C C11 0.1572(2) 0.4058(2) 0.29913(12) 0.0544(4) Uani d . 1 1 . .
    H H11 0.1202 0.4443 0.3625 0.065 Uiso calc R 1 1 . .
    C C6 0.3548(2) 0.0411(2) -0.11100(12) 0.0549(4) Uani d . 1 1 . .
    H H6 0.4194 0.1228 -0.1546 0.066 Uiso calc R 1 1 . .
    C C9 0.3139(2) 0.46746(18) 0.13512(13) 0.0538(4) Uani d . 1 1 . .
    H H9 0.3808 0.5443 0.0892 0.065 Uiso calc R 1 1 . .
    O O2 0.22592(15) 0.05138(14) 0.48843(9) 0.0593(3) Uani d . 1 1 . .
    O O1 0.39648(15) 0.04600(18) 0.35414(10) 0.0745(4) Uani d . 1 1 . .
    O O3 0.02856(18) -0.31220(15) 0.46082(10) 0.0716(4) Uani d . 1 1 . .
    C C7 0.28933(18) 0.08723(17) -0.01311(11) 0.0445(3) Uani d . 1 1 . .
    C C18 -0.0314(2) -0.28576(17) 0.37642(11) 0.0488(3) Uani d . 1 1 . .
    C C5 0.3247(2) -0.1193(2) -0.14145(14) 0.0618(4) Uani d . 1 1 . .
    H H5 0.3696 -0.1466 -0.2051 0.074 Uiso calc R 1 1 . .
    C C3 0.1592(2) -0.20857(18) 0.01646(12) 0.0508(3) Uani d . 1 1 . .
    H H3 0.0939 -0.2935 0.0577 0.061 Uiso calc R 1 1 . .
    C C15 0.07425(18) -0.13590(17) 0.32134(11) 0.0452(3) Uani d . 1 1 . .
    C C10 0.2585(2) 0.52130(19) 0.22792(13) 0.0578(4) Uani d . 1 1 . .
    H H10 0.2871 0.6345 0.2449 0.069 Uiso calc R 1 1 . .
    C C4 0.2252(2) -0.2462(2) -0.07701(14) 0.0588(4) Uani d . 1 1 . .
    H H4 0.2048 -0.3563 -0.0989 0.071 Uiso calc R 1 1 . .
    C C19 -0.3052(3) -0.5404(2) 0.36533(18) 0.0765(5) Uani d . 1 1 . .
    H H19A -0.4202 -0.6062 0.3179 0.115 Uiso calc R 1 1 . .
    H H19B -0.3267 -0.5095 0.4398 0.115 Uiso calc R 1 1 . .
    H H19C -0.2415 -0.6059 0.3690 0.115 Uiso calc R 1 1 . .
    C C17 0.3884(3) 0.1685(3) 0.56385(16) 0.0767(5) Uani d . 1 1 . .
    H H17A 0.3545 0.2006 0.6338 0.115 Uiso calc R 1 1 . .
    H H17B 0.4557 0.2672 0.5302 0.115 Uiso calc R 1 1 . .
    H H17C 0.4634 0.1156 0.5779 0.115 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C2 0.0385(6) 0.0446(7) 0.0367(6) 0.0149(5) 0.0014(5) 0.0111(5)
    C8 0.0422(7) 0.0438(7) 0.0379(6) 0.0126(5) 0.0030(5) 0.0124(5)
    C1 0.0387(6) 0.0446(7) 0.0350(6) 0.0143(5) 0.0027(5) 0.0143(5)
    C16 0.0493(7) 0.0517(7) 0.0466(7) 0.0249(6) 0.0081(6) 0.0219(6)
    N1 0.0484(6) 0.0451(6) 0.0397(6) 0.0120(5) 0.0080(5) 0.0136(5)
    C14 0.0465(7) 0.0429(7) 0.0428(7) 0.0157(5) 0.0075(5) 0.0136(5)
    O4 0.0636(7) 0.0495(6) 0.0614(7) 0.0110(5) 0.0127(5) 0.0236(5)
    C13 0.0395(6) 0.0448(7) 0.0348(6) 0.0153(5) 0.0023(5) 0.0117(5)
    C12 0.0506(7) 0.0535(8) 0.0411(7) 0.0230(6) 0.0081(6) 0.0134(6)
    C11 0.0619(9) 0.0575(9) 0.0440(7) 0.0291(7) 0.0051(6) 0.0058(6)
    C6 0.0510(8) 0.0602(9) 0.0419(7) 0.0153(6) 0.0115(6) 0.0105(6)
    C9 0.0574(8) 0.0425(7) 0.0497(8) 0.0127(6) 0.0043(6) 0.0139(6)
    O2 0.0593(6) 0.0619(7) 0.0536(6) 0.0279(5) 0.0027(5) 0.0030(5)
    O1 0.0492(6) 0.1023(10) 0.0627(7) 0.0255(6) 0.0115(5) 0.0222(6)
    O3 0.0931(9) 0.0618(7) 0.0579(7) 0.0302(6) 0.0085(6) 0.0315(5)
    C7 0.0399(6) 0.0491(7) 0.0366(6) 0.0137(5) 0.0038(5) 0.0109(5)
    C18 0.0622(8) 0.0441(7) 0.0440(7) 0.0252(6) 0.0168(6) 0.0155(6)
    C5 0.0587(9) 0.0693(10) 0.0482(8) 0.0241(8) 0.0113(7) -0.0008(7)
    C3 0.0500(8) 0.0477(7) 0.0493(8) 0.0180(6) 0.0048(6) 0.0107(6)
    C15 0.0502(7) 0.0455(7) 0.0425(7) 0.0220(6) 0.0119(6) 0.0165(5)
    C10 0.0661(9) 0.0442(8) 0.0545(8) 0.0204(7) 0.0005(7) 0.0048(6)
    C4 0.0603(9) 0.0542(8) 0.0561(9) 0.0246(7) 0.0041(7) 0.0001(7)
    C19 0.0826(12) 0.0459(9) 0.0854(13) 0.0120(8) 0.0267(10) 0.0254(8)
    C17 0.0776(12) 0.0741(11) 0.0667(11) 0.0323(9) -0.0107(9) -0.0063(9)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    C2 C1 . 1.4037(18) ?
    C2 C3 . 1.425(2) ?
    C2 C7 . 1.4345(17) ?
    C8 N1 . 1.3482(18) ?
    C8 C9 . 1.424(2) ?
    C8 C13 . 1.4356(17) ?
    C1 C13 . 1.4049(19) ?
    C1 C14 . 1.4823(16) ?
    C16 O1 . 1.1940(17) ?
    C16 O2 . 1.3226(18) ?
    C16 C15 . 1.497(2) ?
    N1 C7 . 1.3381(18) ?
    C14 C15 . 1.3315(18) ?
    C14 H14 . 0.9300 ?
    O4 C18 . 1.3293(19) ?
    O4 C19 . 1.4474(18) ?
    C13 C12 . 1.4301(19) ?
    C12 C11 . 1.355(2) ?
    C12 H12 . 0.9300 ?
    C11 C10 . 1.419(2) ?
    C11 H11 . 0.9300 ?
    C6 C5 . 1.351(2) ?
    C6 C7 . 1.427(2) ?
    C6 H6 . 0.9300 ?
    C9 C10 . 1.358(2) ?
    C9 H9 . 0.9300 ?
    O2 C17 . 1.441(2) ?
    O3 C18 . 1.1981(17) ?
    C18 C15 . 1.4899(18) ?
    C5 C4 . 1.415(2) ?
    C5 H5 . 0.9300 ?
    C3 C4 . 1.358(2) ?
    C3 H3 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C4 H4 . 0.9300 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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
    C1 C2 C3 . . 123.94(12) ?
    C1 C2 C7 . . 117.80(12) ?
    C3 C2 C7 . . 118.24(12) ?
    N1 C8 C9 . . 117.44(12) ?
    N1 C8 C13 . . 123.21(12) ?
    C9 C8 C13 . . 119.35(12) ?
    C2 C1 C13 . . 119.54(11) ?
    C2 C1 C14 . . 117.57(12) ?
    C13 C1 C14 . . 122.87(12) ?
    O1 C16 O2 . . 124.32(15) ?
    O1 C16 C15 . . 124.28(14) ?
    O2 C16 C15 . . 111.38(11) ?
    C7 N1 C8 . . 118.15(11) ?
    C15 C14 C1 . . 126.22(12) ?
    C15 C14 H14 . . 116.9 ?
    C1 C14 H14 . . 116.9 ?
    C18 O4 C19 . . 115.93(13) ?
    C1 C13 C12 . . 124.38(12) ?
    C1 C13 C8 . . 117.77(12) ?
    C12 C13 C8 . . 117.83(12) ?
    C11 C12 C13 . . 120.94(13) ?
    C11 C12 H12 . . 119.5 ?
    C13 C12 H12 . . 119.5 ?
    C12 C11 C10 . . 120.94(14) ?
    C12 C11 H11 . . 119.5 ?
    C10 C11 H11 . . 119.5 ?
    C5 C6 C7 . . 121.14(14) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C10 C9 C8 . . 120.55(13) ?
    C10 C9 H9 . . 119.7 ?
    C8 C9 H9 . . 119.7 ?
    C16 O2 C17 . . 116.36(13) ?
    N1 C7 C6 . . 117.91(12) ?
    N1 C7 C2 . . 123.52(12) ?
    C6 C7 C2 . . 118.55(13) ?
    O3 C18 O4 . . 124.20(13) ?
    O3 C18 C15 . . 123.33(14) ?
    O4 C18 C15 . . 112.42(12) ?
    C6 C5 C4 . . 120.40(14) ?
    C6 C5 H5 . . 119.8 ?
    C4 C5 H5 . . 119.8 ?
    C4 C3 C2 . . 121.06(14) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C14 C15 C18 . . 122.41(13) ?
    C14 C15 C16 . . 122.17(11) ?
    C18 C15 C16 . . 115.18(11) ?
    C9 C10 C11 . . 120.38(14) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C3 C4 C5 . . 120.61(15) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    O4 C19 H19A . . 109.5 ?
    O4 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O4 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O2 C17 H17A . . 109.5 ?
    O2 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O2 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
data_global
_journal_date_recd_electronic     2012-11-29
_journal_date_accepted     2013-01-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      2
_journal_page_first     o224
_journal_page_last     o224
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813000500
_journal_coeditor_code     LR2094
_publ_contact_author_name     ' Professor Carlos Alberto De Simone'
_publ_contact_author_address
;
    Department of Physics and Informatics
    Institute of Physics, University of S\~ao Paulo
    13560-970 S\~ao Carlos, SP
    Brazil
;
_publ_contact_author_email     casimone@ifsc.usp.br
_publ_contact_author_fax     '0055-16-3373-9881'
_publ_contact_author_phone     '0055-16-3373-9881'
_publ_section_title
;
Dimethyl 2-[(acridin-9-yl)methylidene]malonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Almeida, Sinara M. V. de'
;    Laborat\'orio de Imunopatologia Keizo Asami (LIKA)
     Departamento de Bioqu\'imica
     Universidade Federal de Pernambuco
     50670-901 Recife, PE
     Brazil
;
    'Pitta, Ivan R.'
;    Laborat\'orio de S\'intese e Planejamento de F\'armacos
     Departamento de Antibi\'oticos
     Universidade Federal de Pernambuco
     50670-910 Recife, PE
     Brazil
;
    'de Lima, Maria do Carmo A.'
;    Laborat\'orio de S\'intese e Planejamento de F\'armacos
     Departamento de Antibi\'oticos
     Universidade Federal de Pernambuco
     50670-910 Recife, PE
     Brazil
;
    'Mendon\,ca Junior, Francisco J.  B.'
;    Laborat\'orio de S\'intese e Vetoriza\,c\~ao de Mol\'eculas Bioativas
     Universidade Estadual da Para\'iba
     58020-540 Jo\~ao Pessoa, PB
     Brazil
;
    'Simone, Carlos A. de'
;    Departamento de F\'isica e Inform\'atica
     Instituto de F\'isica de S\~ao Carlos
     Universidade de S\~ao Paulo - USP
     13560-970 S\~ao Carlos, SP
     Brazil
;
_publ_section_synopsis     .