#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/44/7114480.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7114480
loop_
_publ_author_name
'Vishweshwar, Peddy'
'Thaimattam, Ram'
'Jaskólski, Mariusz'
'Desiraju, Gautam R.'
_publ_section_title
;
 Supramolecular synthons based on N--H⋯N and C--H⋯O hydrogen 
 bonds. Crystal engineering of a helical structure with 5,5-diethylbarbituric
 acid
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1830
_journal_page_last               1831
_journal_paper_doi               10.1039/b204388b
_journal_year                    2002
_chemical_formula_sum            'C34 H30 N4 O3'
_chemical_formula_weight         542.62
_chemical_melting_point          448
_chemical_name_common
;
1:2 molecular complex of 5,5-diethylbarbituric acid and acridine
;
_chemical_name_systematic
;
1:2 molecular complex of 5,5-diethylbarbituric acid and acridine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 111.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.249(4)
_cell_length_b                   16.260(3)
_cell_length_c                   10.053(2)
_cell_measurement_reflns_used    1250
_cell_measurement_temperature    100
_cell_volume                     2776.0(11)
_computing_data_collection       KUMA-1
_computing_data_reduction        'KM4-RED [KUMA-2]'
_computing_molecular_graphics    'PLUTON (Spek, 1992)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'KUMA CCD detector [KUMA-1]'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8781
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.4468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2597
_reflns_number_total             3138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204388b.txt
_cod_data_source_block           acr
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_cell_measurement_temperature' value '100K' was changed to '100' -
the value should be numeric and without a unit
designator.

'_diffrn_ambient_temperature' value '100K' was changed
to '100' - the value should be numeric and without a unit
designator.

'_chemical_melting_point' value '448 K' was changed to
'448' - the value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2776.0(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7114480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.5000 0.15189(8) 0.7500 0.0217(3) Uani 1 2 d S
O2 O 0.39619(5) 0.38812(6) 0.83857(10) 0.0242(2) Uani 1 1 d .
N1 N 0.44491(6) 0.27128(6) 0.78402(11) 0.0171(2) Uani 1 1 d .
H1A H 0.4058(10) 0.2435(11) 0.7986(17) 0.033(4) Uiso 1 1 d .
N2 N 0.31489(6) 0.18559(6) 0.82960(10) 0.0158(2) Uani 1 1 d .
C1 C 0.5000 0.22656(11) 0.7500 0.0166(4) Uani 1 2 d S
C2 C 0.44347(7) 0.35541(8) 0.79599(13) 0.0166(3) Uani 1 1 d .
C3 C 0.5000 0.40606(10) 0.7500 0.0162(4) Uani 1 2 d S
C4 C 0.44994(8) 0.46116(8) 0.62343(14) 0.0198(3) Uani 1 1 d .
H4A H 0.4865(8) 0.5006(9) 0.6025(15) 0.019(4) Uiso 1 1 d .
H4B H 0.4152(9) 0.4928(9) 0.6572(16) 0.027(4) Uiso 1 1 d .
C5 C 0.40086(9) 0.41340(10) 0.49046(15) 0.0269(3) Uani 1 1 d .
H5A H 0.3746(10) 0.4510(11) 0.4110(19) 0.039(5) Uiso 1 1 d .
H5B H 0.4377(10) 0.3782(11) 0.4586(17) 0.033(4) Uiso 1 1 d .
H5C H 0.3624(10) 0.3803(11) 0.5061(17) 0.035(4) Uiso 1 1 d .
C6 C 0.22545(8) 0.28283(8) 0.67341(14) 0.0229(3) Uani 1 1 d .
H6A H 0.2652(9) 0.2972(9) 0.6340(16) 0.026(4) Uiso 1 1 d .
C7 C 0.15412(9) 0.32095(9) 0.62559(16) 0.0284(3) Uani 1 1 d .
H7A H 0.1429(9) 0.3605(11) 0.5511(18) 0.032(4) Uiso 1 1 d .
C8 C 0.09587(8) 0.30184(9) 0.68389(16) 0.0286(3) Uani 1 1 d .
H8A H 0.0472(10) 0.3320(11) 0.6512(18) 0.037(5) Uiso 1 1 d .
C9 C 0.11027(7) 0.24391(9) 0.78713(14) 0.0238(3) Uani 1 1 d .
H9A H 0.0697(10) 0.2292(10) 0.8296(17) 0.030(4) Uiso 1 1 d .
C10 C 0.18370(7) 0.20118(8) 0.83925(13) 0.0176(3) Uani 1 1 d .
C11 C 0.20055(7) 0.14046(8) 0.94326(13) 0.0183(3) Uani 1 1 d .
H11A H 0.1618(9) 0.1261(9) 0.9835(16) 0.024(4) Uiso 1 1 d .
C12 C 0.27292(7) 0.10015(8) 0.98891(13) 0.0168(3) Uani 1 1 d .
C13 C 0.29324(8) 0.03568(8) 1.09227(14) 0.0217(3) Uani 1 1 d .
H13A H 0.2531(9) 0.0209(10) 1.1316(16) 0.028(4) Uiso 1 1 d .
C14 C 0.36478(8) -0.00142(8) 1.13314(14) 0.0235(3) Uani 1 1 d .
H14A H 0.3773(8) -0.0464(10) 1.2008(16) 0.025(4) Uiso 1 1 d .
C15 C 0.42137(8) 0.02508(8) 1.07577(13) 0.0208(3) Uani 1 1 d .
H15A H 0.4749(9) -0.0021(9) 1.1079(16) 0.024(4) Uiso 1 1 d .
C16 C 0.40484(7) 0.08695(8) 0.97811(13) 0.0169(3) Uani 1 1 d .
H16A H 0.4435(8) 0.1072(9) 0.9401(15) 0.019(4) Uiso 1 1 d .
C17 C 0.32958(7) 0.12611(8) 0.92946(12) 0.0151(3) Uani 1 1 d .
C18 C 0.24314(7) 0.22181(8) 0.78261(13) 0.0166(3) Uani 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C1 125.77(11) . .
C2 N1 H1A 116.3(11) . .
C1 N1 H1A 118.0(11) . .
C17 N2 C18 118.38(10) . .
O1 C1 N1 121.76(8) . .
O1 C1 N1 121.76(8) . 2_656
N1 C1 N1 116.48(15) . 2_656
O2 C2 N1 120.30(11) . .
O2 C2 C3 121.21(12) . .
N1 C2 C3 118.45(11) . .
C2 C3 C2 114.30(14) . 2_656
C2 C3 C4 108.99(7) . 2_656
C2 C3 C4 107.53(7) 2_656 2_656
C2 C3 C4 107.54(7) . .
C2 C3 C4 108.99(7) 2_656 .
C4 C3 C4 109.42(15) 2_656 .
C5 C4 C3 113.98(12) . .
C5 C4 H4A 111.4(8) . .
C3 C4 H4A 107.7(8) . .
C5 C4 H4B 109.2(9) . .
C3 C4 H4B 106.5(9) . .
H4A C4 H4B 107.7(12) . .
C4 C5 H5A 110.6(10) . .
C4 C5 H5B 108.6(9) . .
H5A C5 H5B 106.0(13) . .
C4 C5 H5C 112.3(10) . .
H5A C5 H5C 108.7(14) . .
H5B C5 H5C 110.4(14) . .
C7 C6 C18 120.44(13) . .
C7 C6 H6A 120.4(9) . .
C18 C6 H6A 119.1(9) . .
C6 C7 C8 121.13(14) . .
C6 C7 H7A 119.2(10) . .
C8 C7 H7A 119.6(9) . .
C9 C8 C7 120.19(13) . .
C9 C8 H8A 120.9(10) . .
C7 C8 H8A 118.9(10) . .
C8 C9 C10 120.82(13) . .
C8 C9 H9A 121.5(9) . .
C10 C9 H9A 117.7(9) . .
C11 C10 C9 122.81(12) . .
C11 C10 C18 118.24(11) . .
C9 C10 C18 118.96(12) . .
C10 C11 C12 120.31(11) . .
C10 C11 H11A 119.6(9) . .
C12 C11 H11A 120.1(9) . .
C11 C12 C13 123.24(11) . .
C11 C12 C17 117.73(11) . .
C13 C12 C17 119.02(11) . .
C14 C13 C12 120.78(12) . .
C14 C13 H13A 123.1(9) . .
C12 C13 H13A 116.1(9) . .
C13 C14 C15 120.22(12) . .
C13 C14 H14A 120.2(9) . .
C15 C14 H14A 119.6(9) . .
C16 C15 C14 120.99(12) . .
C16 C15 H15A 119.2(8) . .
C14 C15 H15A 119.8(8) . .
C15 C16 C17 120.56(12) . .
C15 C16 H16A 122.1(8) . .
C17 C16 H16A 117.3(8) . .
N2 C17 C16 118.62(10) . .
N2 C17 C12 122.97(11) . .
C16 C17 C12 118.41(11) . .
N2 C18 C6 119.27(11) . .
N2 C18 C10 122.29(11) . .
C6 C18 C10 118.44(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.214(2) .
O2 C2 1.2170(14) .
N1 C2 1.3743(16) .
N1 C1 1.3813(14) .
N1 H1A 0.901(17) .
N2 C17 1.3483(16) .
N2 C18 1.3535(16) .
C1 N1 1.3814(14) 2_656
C2 C3 1.5183(15) .
C3 C2 1.5184(15) 2_656
C3 C4 1.5509(17) 2_656
C3 C4 1.5509(17) .
C4 C5 1.522(2) .
C4 H4A 1.002(14) .
C4 H4B 0.968(15) .
C5 H5A 0.981(18) .
C5 H5B 1.020(17) .
C5 H5C 0.942(17) .
C6 C7 1.361(2) .
C6 C18 1.4263(18) .
C6 H6A 0.974(15) .
C7 C8 1.423(2) .
C7 H7A 0.950(17) .
C8 C9 1.354(2) .
C8 H8A 0.961(18) .
C9 C10 1.4279(18) .
C9 H9A 1.009(16) .
C10 C11 1.3883(18) .
C10 C18 1.4371(17) .
C11 C12 1.3931(18) .
C11 H11A 0.964(15) .
C12 C13 1.4262(18) .
C12 C17 1.4342(17) .
C13 C14 1.358(2) .
C13 H13A 0.981(16) .
C14 C15 1.4216(19) .
C14 H14A 0.967(16) .
C15 C16 1.3602(18) .
C15 H15A 1.011(15) .
C16 C17 1.4279(17) .
C16 H16A 0.975(14) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184980
