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#$Date: 2021-11-17 11:31:03 +0200 (Wed, 17 Nov 2021) $
#$Revision: 270720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/52/1565297.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_1565297
loop_
_publ_author_name
'Mandal, Arkalekha'
'Ghosh, Subhendu'
'Nath, Bhaskar'
'Patel, Bhisma Kumar'
_publ_section_title
;
 Role of non-covalent interactions to dictate chiral selective
 self-assembly in Ni(II), Cu(II) and Cd(II) complexes of a racemic
 1,2-dihydroquinazolinone ligand
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119399
_journal_paper_doi               10.1016/j.ica.2019.119399
_journal_volume                  503
_journal_year                    2020
_chemical_formula_sum            'C19 H18 Cu N8 O8'
_chemical_formula_weight         549.94
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                79.3270(10)
_cell_angle_beta                 83.0580(10)
_cell_angle_gamma                89.6590(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5196(2)
_cell_length_b                   11.3616(3)
_cell_length_c                   13.2177(3)
_cell_measurement_reflns_used    3701
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      1.58
_cell_volume                     1101.42(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area diffractometer'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13194
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             562
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0313
_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)+(0.0540P)²+0.5800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                3209
_reflns_number_total             3701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2020-503-119399.cif
_cod_data_source_block           complex2
_cod_database_code               1565297
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.39063(4) 0.14395(3) 0.14932(2) 0.03563(12) Uani 1 1 d . . .
O1 O 0.7545(2) 0.12018(15) 0.35832(14) 0.0407(4) Uani 1 1 d . . .
O2 O 0.2850(3) 0.13017(17) 0.02146(13) 0.0447(5) Uani 1 1 d . . .
O3 O 0.1122(4) 0.2621(2) 0.0783(2) 0.0794(7) Uani 1 1 d . . .
O4 O 0.0826(5) 0.2093(4) -0.0670(3) 0.1415(16) Uani 1 1 d . . .
O5 O 0.5948(4) 0.0018(2) 0.13401(19) 0.0744(8) Uani 1 1 d . . .
H5C H 0.5878 -0.0474 0.1883 0.112 Uiso 1 1 calc R . .
O6 O 0.4338(3) 0.1440(2) 0.66909(16) 0.0622(6) Uani 1 1 d . . .
O7 O 0.5450(4) 0.2949(2) 0.7190(2) 0.0912(9) Uani 1 1 d . . .
O8 O 0.5486(4) 0.2887(3) 0.5564(2) 0.0960(9) Uani 1 1 d . . .
N1 N 0.2174(3) 0.02275(18) 0.23770(15) 0.0369(5) Uani 1 1 d . . .
N2 N 0.4333(3) 0.16789(18) 0.28541(15) 0.0323(5) Uani 1 1 d . . .
N3 N 0.5507(3) 0.25750(17) 0.30031(15) 0.0319(4) Uani 1 1 d . . .
N4 N 0.5567(3) 0.28016(19) 0.07549(15) 0.0371(5) Uani 1 1 d . . .
N5 N 0.3652(3) 0.10172(19) 0.46489(15) 0.0362(5) Uani 1 1 d . . .
H5A H 0.4327 0.1554 0.4798 0.043 Uiso 1 1 calc R . .
H5B H 0.3064 0.0511 0.5137 0.043 Uiso 1 1 calc R . .
N6 N 0.6060(3) 0.4646(2) 0.27443(19) 0.0413(6) Uani 1 1 d . . .
N7 N 0.1565(4) 0.2029(2) 0.0098(2) 0.0578(7) Uani 1 1 d . . .
N8 N 0.5090(3) 0.2445(2) 0.6486(2) 0.0513(6) Uani 1 1 d . . .
C1 C 0.1047(4) -0.0486(2) 0.2048(2) 0.0474(7) Uani 1 1 d . . .
H1 H 0.0967 -0.0390 0.1341 0.057 Uiso 1 1 calc R . .
C2 C 0.0005(4) -0.1354(3) 0.2716(2) 0.0488(7) Uani 1 1 d . . .
H2 H -0.0778 -0.1828 0.2464 0.059 Uiso 1 1 calc R . .
C3 C 0.0133(4) -0.1512(2) 0.3751(2) 0.0432(6) Uani 1 1 d . . .
H3 H -0.0549 -0.2104 0.4213 0.052 Uiso 1 1 calc R . .
C4 C 0.1291(3) -0.0779(2) 0.4112(2) 0.0374(6) Uani 1 1 d . . .
H4 H 0.1397 -0.0872 0.4816 0.045 Uiso 1 1 calc R . .
C5 C 0.2276(3) 0.0085(2) 0.34041(18) 0.0313(5) Uani 1 1 d . . .
C6 C 0.3521(3) 0.0971(2) 0.36751(17) 0.0298(5) Uani 1 1 d . . .
C7 C 0.7189(3) 0.2253(2) 0.32784(17) 0.0322(5) Uani 1 1 d . . .
C8 C 0.8364(3) 0.3287(2) 0.32820(18) 0.0329(5) Uani 1 1 d . . .
C9 C 1.0070(3) 0.3087(2) 0.36062(19) 0.0402(6) Uani 1 1 d . . .
H9 H 1.0528 0.2318 0.3704 0.048 Uiso 1 1 calc R . .
C10 C 1.1067(4) 0.4030(3) 0.3780(2) 0.0462(7) Uani 1 1 d . . .
H10 H 1.2194 0.3896 0.3997 0.055 Uiso 1 1 calc R . .
C11 C 1.0391(4) 0.5168(3) 0.3631(2) 0.0502(7) Uani 1 1 d . . .
H11 H 1.1061 0.5797 0.3761 0.060 Uiso 1 1 calc R . .
C12 C 0.8738(4) 0.5393(2) 0.3292(2) 0.0459(7) Uani 1 1 d . . .
H12 H 0.8304 0.6169 0.3191 0.055 Uiso 1 1 calc R . .
C13 C 0.7711(3) 0.4449(2) 0.31000(18) 0.0362(6) Uani 1 1 d . . .
C14 C 0.5292(3) 0.3736(2) 0.23090(18) 0.0332(5) Uani 1 1 d . . .
H14 H 0.4006 0.3886 0.2314 0.040 Uiso 1 1 calc R . .
C15 C 0.6088(3) 0.3723(2) 0.11828(19) 0.0345(6) Uani 1 1 d . . .
C16 C 0.7201(4) 0.4625(2) 0.0612(2) 0.0438(6) Uani 1 1 d . . .
H16 H 0.7532 0.5255 0.0913 0.053 Uiso 1 1 calc R . .
C17 C 0.7831(4) 0.4593(3) -0.0416(2) 0.0508(7) Uani 1 1 d . . .
H17 H 0.8588 0.5198 -0.0807 0.061 Uiso 1 1 calc R . .
C18 C 0.7323(4) 0.3661(3) -0.0842(2) 0.0511(7) Uani 1 1 d . . .
H18 H 0.7730 0.3618 -0.1527 0.061 Uiso 1 1 calc R . .
C19 C 0.6198(4) 0.2785(3) -0.0241(2) 0.0464(7) Uani 1 1 d . . .
H19 H 0.5856 0.2152 -0.0535 0.056 Uiso 1 1 calc R . .
H6 H 0.563(4) 0.524(3) 0.275(2) 0.052(10) Uiso 1 1 d . . .
H5D H 0.637(5) -0.028(3) 0.093(3) 0.071(12) Uiso 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'
Cu Cu 0.3201 1.2651 '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'
H H 0.0000 0.0000 '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
N2 Cu1 O2 165.67(8) . .
N2 Cu1 N1 80.09(8) . .
O2 Cu1 N1 92.38(8) . .
N2 Cu1 N4 93.35(8) . .
O2 Cu1 N4 93.03(8) . .
N1 Cu1 N4 172.02(8) . .
N2 Cu1 O5 97.08(9) . .
O2 Cu1 O5 95.18(9) . .
N1 Cu1 O5 90.79(10) . .
N4 Cu1 O5 94.56(10) . .
N7 O2 Cu1 109.78(15) . .
Cu1 O5 H5C 109.5 . .
Cu1 O5 H5D 137(3) . .
H5C O5 H5D 106.9 . .
C1 N1 C5 118.4(2) . .
C1 N1 Cu1 126.88(18) . .
C5 N1 Cu1 114.61(16) . .
C6 N2 N3 118.30(18) . .
C6 N2 Cu1 119.07(15) . .
N3 N2 Cu1 122.62(15) . .
C7 N3 N2 118.98(19) . .
C7 N3 C14 119.35(19) . .
N2 N3 C14 112.55(17) . .
C19 N4 C15 118.1(2) . .
C19 N4 Cu1 116.73(18) . .
C15 N4 Cu1 125.19(17) . .
C6 N5 H5A 120.0 . .
C6 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
C13 N6 C14 118.7(2) . .
C13 N6 H6 119(2) . .
C14 N6 H6 122(2) . .
O4 N7 O3 123.4(3) . .
O4 N7 O2 118.1(3) . .
O3 N7 O2 118.5(2) . .
O8 N8 O7 122.4(3) . .
O8 N8 O6 117.1(2) . .
O7 N8 O6 120.5(3) . .
N1 C1 C2 122.4(2) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 119.2(2) . .
C3 C2 H2 120.4 . .
C1 C2 H2 120.4 . .
C2 C3 C4 119.5(3) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C5 C4 C3 118.4(2) . .
C5 C4 H4 120.8 . .
C3 C4 H4 120.8 . .
N1 C5 C4 122.1(2) . .
N1 C5 C6 113.1(2) . .
C4 C5 C6 124.7(2) . .
N2 C6 N5 126.8(2) . .
N2 C6 C5 112.61(19) . .
N5 C6 C5 120.6(2) . .
O1 C7 N3 121.1(2) . .
O1 C7 C8 125.0(2) . .
N3 C7 C8 113.5(2) . .
C13 C8 C9 119.7(2) . .
C13 C8 C7 120.4(2) . .
C9 C8 C7 119.4(2) . .
C10 C9 C8 120.1(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 119.9(3) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C12 121.2(2) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
C11 C12 C13 119.8(3) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
N6 C13 C8 119.4(2) . .
N6 C13 C12 121.3(2) . .
C8 C13 C12 119.2(2) . .
N6 C14 N3 107.50(19) . .
N6 C14 C15 113.3(2) . .
N3 C14 C15 112.08(19) . .
N6 C14 H14 107.9 . .
N3 C14 H14 107.9 . .
C15 C14 H14 107.9 . .
N4 C15 C16 121.0(2) . .
N4 C15 C14 116.7(2) . .
C16 C15 C14 122.2(2) . .
C15 C16 C17 120.0(3) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C18 C17 C16 119.0(3) . .
C18 C17 H17 120.5 . .
C16 C17 H17 120.5 . .
C17 C18 C19 118.8(3) . .
C17 C18 H18 120.6 . .
C19 C18 H18 120.6 . .
N4 C19 C18 123.1(3) . .
N4 C19 H19 118.4 . .
C18 C19 H19 118.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.9325(18) .
Cu1 O2 1.9840(17) .
Cu1 N1 2.004(2) .
Cu1 N4 2.019(2) .
Cu1 O5 2.242(2) .
O1 C7 1.227(3) .
O2 N7 1.273(3) .
O3 N7 1.239(3) .
O4 N7 1.205(3) .
O5 H5C 0.8200 .
O5 H5D 0.74(4) .
O6 N8 1.246(3) .
O7 N8 1.236(3) .
O8 N8 1.230(3) .
N1 C1 1.338(3) .
N1 C5 1.349(3) .
N2 C6 1.311(3) .
N2 N3 1.408(3) .
N3 C7 1.386(3) .
N3 C14 1.481(3) .
N4 C19 1.347(3) .
N4 C15 1.359(3) .
N5 C6 1.313(3) .
N5 H5A 0.8600 .
N5 H5B 0.8600 .
N6 C13 1.383(3) .
N6 C14 1.429(3) .
N6 H6 0.74(3) .
C1 C2 1.373(4) .
C1 H1 0.9300 .
C2 C3 1.362(4) .
C2 H2 0.9300 .
C3 C4 1.391(3) .
C3 H3 0.9300 .
C4 C5 1.375(3) .
C4 H4 0.9300 .
C5 C6 1.498(3) .
C7 C8 1.475(3) .
C8 C13 1.395(3) .
C8 C9 1.405(3) .
C9 C10 1.380(4) .
C9 H9 0.9300 .
C10 C11 1.375(4) .
C10 H10 0.9300 .
C11 C12 1.378(4) .
C11 H11 0.9300 .
C12 C13 1.403(3) .
C12 H12 0.9300 .
C14 C15 1.538(3) .
C14 H14 0.9800 .
C15 C16 1.374(4) .
C16 C17 1.390(4) .
C16 H16 0.9300 .
C17 C18 1.365(4) .
C17 H17 0.9300 .
C18 C19 1.375(4) .
C18 H18 0.9300 .
C19 H19 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 Cu1 O2 N7 30.2(4) . . . .
N1 Cu1 O2 N7 88.00(19) . . . .
N4 Cu1 O2 N7 -86.12(19) . . . .
O5 Cu1 O2 N7 179.01(19) . . . .
N2 Cu1 N1 C1 178.3(3) . . . .
O2 Cu1 N1 C1 10.5(2) . . . .
N4 Cu1 N1 C1 143.1(5) . . . .
O5 Cu1 N1 C1 -84.7(2) . . . .
N2 Cu1 N1 C5 -6.43(17) . . . .
O2 Cu1 N1 C5 -174.16(17) . . . .
N4 Cu1 N1 C5 -41.6(7) . . . .
O5 Cu1 N1 C5 90.62(18) . . . .
O2 Cu1 N2 C6 64.0(4) . . . .
N1 Cu1 N2 C6 4.92(18) . . . .
N4 Cu1 N2 C6 -179.67(18) . . . .
O5 Cu1 N2 C6 -84.6(2) . . . .
O2 Cu1 N2 N3 -117.0(3) . . . .
N1 Cu1 N2 N3 -176.06(19) . . . .
N4 Cu1 N2 N3 -0.65(18) . . . .
O5 Cu1 N2 N3 94.37(18) . . . .
C6 N2 N3 C7 75.9(3) . . . .
Cu1 N2 N3 C7 -103.1(2) . . . .
C6 N2 N3 C14 -137.3(2) . . . .
Cu1 N2 N3 C14 43.7(2) . . . .
N2 Cu1 N4 C19 159.3(2) . . . .
O2 Cu1 N4 C19 -33.5(2) . . . .
N1 Cu1 N4 C19 -166.1(5) . . . .
O5 Cu1 N4 C19 61.9(2) . . . .
N2 Cu1 N4 C15 -20.8(2) . . . .
O2 Cu1 N4 C15 146.4(2) . . . .
N1 Cu1 N4 C15 13.8(7) . . . .
O5 Cu1 N4 C15 -118.2(2) . . . .
Cu1 O2 N7 O4 176.9(3) . . . .
Cu1 O2 N7 O3 -4.1(3) . . . .
C5 N1 C1 C2 -0.2(4) . . . .
Cu1 N1 C1 C2 174.9(2) . . . .
N1 C1 C2 C3 -0.9(5) . . . .
C1 C2 C3 C4 1.0(4) . . . .
C2 C3 C4 C5 0.0(4) . . . .
C1 N1 C5 C4 1.3(4) . . . .
Cu1 N1 C5 C4 -174.45(19) . . . .
C1 N1 C5 C6 -177.4(2) . . . .
Cu1 N1 C5 C6 6.8(3) . . . .
C3 C4 C5 N1 -1.1(4) . . . .
C3 C4 C5 C6 177.4(2) . . . .
N3 N2 C6 N5 1.5(4) . . . .
Cu1 N2 C6 N5 -179.47(19) . . . .
N3 N2 C6 C5 178.37(18) . . . .
Cu1 N2 C6 C5 -2.6(3) . . . .
N1 C5 C6 N2 -3.0(3) . . . .
C4 C5 C6 N2 178.4(2) . . . .
N1 C5 C6 N5 174.2(2) . . . .
C4 C5 C6 N5 -4.5(4) . . . .
N2 N3 C7 O1 -14.0(3) . . . .
C14 N3 C7 O1 -158.5(2) . . . .
N2 N3 C7 C8 172.75(19) . . . .
C14 N3 C7 C8 28.2(3) . . . .
O1 C7 C8 C13 -168.2(2) . . . .
N3 C7 C8 C13 4.8(3) . . . .
O1 C7 C8 C9 3.3(4) . . . .
N3 C7 C8 C9 176.3(2) . . . .
C13 C8 C9 C10 2.3(4) . . . .
C7 C8 C9 C10 -169.2(2) . . . .
C8 C9 C10 C11 -0.3(4) . . . .
C9 C10 C11 C12 -1.1(4) . . . .
C10 C11 C12 C13 0.4(4) . . . .
C14 N6 C13 C8 -16.8(4) . . . .
C14 N6 C13 C12 163.9(2) . . . .
C9 C8 C13 N6 177.6(2) . . . .
C7 C8 C13 N6 -10.9(4) . . . .
C9 C8 C13 C12 -3.0(4) . . . .
C7 C8 C13 C12 168.5(2) . . . .
C11 C12 C13 N6 -179.0(3) . . . .
C11 C12 C13 C8 1.6(4) . . . .
C13 N6 C14 N3 45.2(3) . . . .
C13 N6 C14 C15 -79.2(3) . . . .
C7 N3 C14 N6 -52.4(3) . . . .
N2 N3 C14 N6 160.9(2) . . . .
C7 N3 C14 C15 72.7(2) . . . .
N2 N3 C14 C15 -73.9(2) . . . .
C19 N4 C15 C16 1.1(4) . . . .
Cu1 N4 C15 C16 -178.79(18) . . . .
C19 N4 C15 C14 178.0(2) . . . .
Cu1 N4 C15 C14 -1.9(3) . . . .
N6 C14 C15 N4 173.0(2) . . . .
N3 C14 C15 N4 51.1(3) . . . .
N6 C14 C15 C16 -10.2(3) . . . .
N3 C14 C15 C16 -132.1(2) . . . .
N4 C15 C16 C17 -0.9(4) . . . .
C14 C15 C16 C17 -177.6(2) . . . .
C15 C16 C17 C18 0.2(4) . . . .
C16 C17 C18 C19 0.2(4) . . . .
C15 N4 C19 C18 -0.7(4) . . . .
Cu1 N4 C19 C18 179.2(2) . . . .
C17 C18 C19 N4 0.0(4) . . . .
