#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/73/2237360.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_2237360
loop_
_publ_author_name
'de Almeida, Sinara M. V.'
'Pitta, Ivan R.'
'do Lima, Maria'
'Mendonça Junior, Francisco J. B.'
'de Simone, Carlos A.'
_publ_section_title
;
 Dimethyl 2-[(acridin-9-yl)methylidene]malonate
;
_journal_coeditor_code           LR2094
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o224
_journal_paper_doi               10.1107/S1600536813000500
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C19 H15 N O4'
_chemical_formula_moiety         'C19 H15 N O4'
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_weight         321.32
_chemical_name_systematic
;
Dimethyl 2-[(acridin-9-yl)methylidene]malonate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.468(2)
_cell_angle_beta                 93.652(2)
_cell_angle_gamma                117.422(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3022(2)
_cell_length_b                   9.0208(3)
_cell_length_c                   12.0334(4)
_cell_measurement_reflns_used    6418
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     788.00(4)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images,thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Enraf Nonius FR590'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10674
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.244
_refine_ls_extinction_coef       0.168(19)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0515
_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)+(0.0817P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2805
_reflns_number_total             3626
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lr2094.cif
_cod_data_source_block           I
_cod_original_cell_volume        787.98(4)
_cod_database_code               2237360
_cod_database_fobs_code          2237360
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_symmetry_multiplicity
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_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
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658315
2 PubChem 139085181
