#------------------------------------------------------------------------------
#$Date: 2023-11-06 17:22:13 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570250.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_1570250
loop_
_publ_author_name
'Sarhan, Ahmed A. M.'
'Haukka, Matti'
'Barakat, Assem'
'Soliman, Saied M.'
'Boraei, Ahmed T. A.'
'Sopaih, Manar'
'Salama, Eid E.'
_publ_section_title
;
 4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis:
 Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the
 Intermediates
;
_journal_issue                   11
_journal_name_full               Crystals
_journal_page_first              1537
_journal_paper_doi               10.3390/cryst13111537
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C20 H14 N2 O3'
_chemical_formula_sum            'C20 H14 N2 O3'
_chemical_formula_weight         330.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 113.9469(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.89752(13)
_cell_length_b                   5.76627(4)
_cell_length_c                   17.97633(13)
_cell_measurement_reflns_used    22420
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      79.0380
_cell_measurement_theta_min      2.8620
_cell_volume                     1600.77(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
;
_computing_molecular_graphics
'CrystaMaker X (CrystalMaker Software ltd., 2022)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.198
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+0.5098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3275
_reflns_number_total             3465
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nd61.cif
_cod_data_source_block           nd61
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570250
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.923
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55151(5) 0.19766(14) 0.85063(5) 0.03109(19) Uani 1 1 d . . . . .
O2 O 0.35731(5) 0.39535(14) 0.77277(5) 0.03211(19) Uani 1 1 d . . . . .
O3 O 0.41968(5) 0.73756(13) 0.76773(5) 0.02746(18) Uani 1 1 d . . . . .
N1 N 0.48130(6) 0.24465(16) 0.56690(5) 0.0262(2) Uani 1 1 d . . . . .
N2 N 0.42264(6) 0.41863(16) 0.54710(5) 0.0262(2) Uani 1 1 d . . . . .
C1 C 0.64837(7) -0.2102(2) 0.80818(7) 0.0309(2) Uani 1 1 d . . . . .
H1 H 0.663881 -0.215535 0.865213 0.037 Uiso 1 1 calc R U . . .
C2 C 0.67970(7) -0.3747(2) 0.76994(8) 0.0337(3) Uani 1 1 d . . . . .
H2 H 0.717882 -0.492568 0.801457 0.040 Uiso 1 1 calc R U . . .
C3 C 0.65563(7) -0.3681(2) 0.68600(8) 0.0320(2) Uani 1 1 d . . . . .
H3 H 0.676639 -0.484127 0.661126 0.038 Uiso 1 1 calc R U . . .
C4 C 0.60139(7) -0.1947(2) 0.63778(7) 0.0282(2) Uani 1 1 d . . . . .
H4 H 0.585255 -0.190434 0.580649 0.034 Uiso 1 1 calc R U . . .
C5 C 0.57192(7) -0.02905(19) 0.67625(6) 0.0252(2) Uani 1 1 d . . . . .
C6 C 0.59396(7) -0.03908(19) 0.76037(6) 0.0266(2) Uani 1 1 d . . . . .
C7 C 0.54631(7) 0.14569(19) 0.78344(6) 0.0259(2) Uani 1 1 d . . . . .
C8 C 0.49079(7) 0.26209(18) 0.70424(6) 0.0244(2) Uani 1 1 d . . . . .
C9 C 0.51174(6) 0.16735(18) 0.64254(6) 0.0241(2) Uani 1 1 d . . . . .
C10 C 0.39520(7) 0.50587(18) 0.60155(6) 0.0245(2) Uani 1 1 d . . . . .
C11 C 0.32691(7) 0.68545(19) 0.56937(6) 0.0255(2) Uani 1 1 d . . . . .
C12 C 0.33285(7) 0.85489(19) 0.51641(6) 0.0271(2) Uani 1 1 d . . . . .
H12 H 0.379620 0.852271 0.499936 0.033 Uiso 1 1 calc R U . . .
C13 C 0.27033(8) 1.0272(2) 0.48785(7) 0.0309(2) Uani 1 1 d . . . . .
H13 H 0.275214 1.144360 0.452791 0.037 Uiso 1 1 calc R U . . .
C14 C 0.20077(8) 1.0295(2) 0.51013(7) 0.0345(3) Uani 1 1 d . . . . .
H14 H 0.158166 1.147864 0.490398 0.041 Uiso 1 1 calc R U . . .
C15 C 0.19361(8) 0.8584(2) 0.56135(7) 0.0365(3) Uani 1 1 d . . . . .
H15 H 0.145602 0.858504 0.576073 0.044 Uiso 1 1 calc R U . . .
C16 C 0.25629(7) 0.6873(2) 0.59107(7) 0.0320(2) Uani 1 1 d . . . . .
H16 H 0.251241 0.570955 0.626311 0.038 Uiso 1 1 calc R U . . .
C17 C 0.42945(7) 0.43247(18) 0.68444(6) 0.0240(2) Uani 1 1 d . . . . .
C18 C 0.39780(7) 0.51847(18) 0.74670(6) 0.0247(2) Uani 1 1 d . . . . .
C19 C 0.39325(8) 0.8289(2) 0.83044(7) 0.0344(3) Uani 1 1 d . . . . .
H19A H 0.337285 0.759185 0.823980 0.041 Uiso 1 1 calc R U . . .
H19B H 0.385534 0.999043 0.824355 0.041 Uiso 1 1 calc R U . . .
C20 C 0.46145(10) 0.7722(3) 0.91354(8) 0.0430(3) Uani 1 1 d . . . . .
H20A H 0.468515 0.603592 0.919448 0.065 Uiso 1 1 calc R U . . .
H20B H 0.443667 0.832952 0.955320 0.065 Uiso 1 1 calc R U . . .
H20C H 0.516534 0.843144 0.919907 0.065 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C18 O3 C19 115.06(8) . . ?
C9 N1 N2 117.31(9) . . ?
C10 N2 N1 121.36(9) . . ?
C6 C1 C2 117.88(11) . . ?
C6 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 120.79(11) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 121.42(11) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 117.57(10) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C5 C6 121.16(10) . . ?
C4 C5 C9 130.61(10) . . ?
C6 C5 C9 108.11(9) . . ?
C1 C6 C5 121.13(10) . . ?
C1 C6 C7 129.32(10) . . ?
C5 C6 C7 109.44(9) . . ?
O1 C7 C6 128.63(10) . . ?
O1 C7 C8 126.61(10) . . ?
C6 C7 C8 104.74(9) . . ?
C17 C8 C9 118.79(9) . . ?
C17 C8 C7 132.97(10) . . ?
C9 C8 C7 108.23(9) . . ?
N1 C9 C8 124.34(10) . . ?
N1 C9 C5 126.62(9) . . ?
C8 C9 C5 109.04(9) . . ?
N2 C10 C17 122.54(10) . . ?
N2 C10 C11 115.00(9) . . ?
C17 C10 C11 122.46(9) . . ?
C12 C11 C16 119.39(10) . . ?
C12 C11 C10 119.69(10) . . ?
C16 C11 C10 120.93(10) . . ?
C13 C12 C11 119.92(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.46(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.79(11) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.21(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.21(11) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C8 C17 C10 115.40(9) . . ?
C8 C17 C18 120.23(9) . . ?
C10 C17 C18 124.23(9) . . ?
O2 C18 O3 125.90(10) . . ?
O2 C18 C17 121.58(10) . . ?
O3 C18 C17 112.52(9) . . ?
O3 C19 C20 109.56(10) . . ?
O3 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
O3 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2126(13) . yes
O2 C18 1.2050(13) . yes
O3 C18 1.3275(13) . yes
O3 C19 1.4684(13) . yes
N1 C9 1.3207(14) . yes
N1 N2 1.3525(13) . yes
N2 C10 1.3396(14) . yes
C1 C6 1.3843(16) . ?
C1 C2 1.3957(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3949(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3948(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3850(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4041(15) . ?
C5 C9 1.4777(15) . ?
C6 C7 1.4921(15) . ?
C7 C8 1.5078(14) . ?
C8 C17 1.3663(15) . ?
C8 C9 1.4046(14) . ?
C10 C17 1.4261(14) . ?
C10 C11 1.4820(15) . ?
C11 C12 1.3959(15) . ?
C11 C16 1.3981(15) . ?
C12 C13 1.3879(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3873(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3880(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3859(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.5068(14) . ?
C19 C20 1.5063(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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
_geom_torsion_publ_flag
C9 N1 N2 C10 -1.32(15) . . . . ?
C6 C1 C2 C3 -0.99(17) . . . . ?
C1 C2 C3 C4 1.56(18) . . . . ?
C2 C3 C4 C5 -0.18(17) . . . . ?
C3 C4 C5 C6 -1.71(16) . . . . ?
C3 C4 C5 C9 -177.02(10) . . . . ?
C2 C1 C6 C5 -0.90(16) . . . . ?
C2 C1 C6 C7 174.97(11) . . . . ?
C4 C5 C6 C1 2.30(16) . . . . ?
C9 C5 C6 C1 178.55(10) . . . . ?
C4 C5 C6 C7 -174.31(10) . . . . ?
C9 C5 C6 C7 1.95(12) . . . . ?
C1 C6 C7 O1 7.44(19) . . . . ?
C5 C6 C7 O1 -176.31(11) . . . . ?
C1 C6 C7 C8 -174.16(11) . . . . ?
C5 C6 C7 C8 2.08(11) . . . . ?
O1 C7 C8 C17 -6.12(19) . . . . ?
C6 C7 C8 C17 175.44(11) . . . . ?
O1 C7 C8 C9 172.91(11) . . . . ?
C6 C7 C8 C9 -5.53(11) . . . . ?
N2 N1 C9 C8 -3.62(15) . . . . ?
N2 N1 C9 C5 176.15(9) . . . . ?
C17 C8 C9 N1 5.87(16) . . . . ?
C7 C8 C9 N1 -173.32(10) . . . . ?
C17 C8 C9 C5 -173.94(9) . . . . ?
C7 C8 C9 C5 6.87(11) . . . . ?
C4 C5 C9 N1 -9.63(18) . . . . ?
C6 C5 C9 N1 174.60(10) . . . . ?
C4 C5 C9 C8 170.18(11) . . . . ?
C6 C5 C9 C8 -5.60(12) . . . . ?
N1 N2 C10 C17 3.99(16) . . . . ?
N1 N2 C10 C11 -176.35(9) . . . . ?
N2 C10 C11 C12 -41.82(14) . . . . ?
C17 C10 C11 C12 137.84(11) . . . . ?
N2 C10 C11 C16 137.96(11) . . . . ?
C17 C10 C11 C16 -42.38(15) . . . . ?
C16 C11 C12 C13 1.98(16) . . . . ?
C10 C11 C12 C13 -178.24(10) . . . . ?
C11 C12 C13 C14 -1.43(16) . . . . ?
C12 C13 C14 C15 0.00(18) . . . . ?
C13 C14 C15 C16 0.86(19) . . . . ?
C14 C15 C16 C11 -0.29(19) . . . . ?
C12 C11 C16 C15 -1.13(17) . . . . ?
C10 C11 C16 C15 179.09(11) . . . . ?
C9 C8 C17 C10 -2.96(14) . . . . ?
C7 C8 C17 C10 175.99(10) . . . . ?
C9 C8 C17 C18 172.84(9) . . . . ?
C7 C8 C17 C18 -8.22(18) . . . . ?
N2 C10 C17 C8 -1.65(15) . . . . ?
C11 C10 C17 C8 178.71(9) . . . . ?
N2 C10 C17 C18 -177.26(10) . . . . ?
C11 C10 C17 C18 3.11(16) . . . . ?
C19 O3 C18 O2 2.03(16) . . . . ?
C19 O3 C18 C17 -177.96(9) . . . . ?
C8 C17 C18 O2 -66.10(14) . . . . ?
C10 C17 C18 O2 109.30(13) . . . . ?
C8 C17 C18 O3 113.89(11) . . . . ?
C10 C17 C18 O3 -70.71(13) . . . . ?
C18 O3 C19 C20 86.41(12) . . . . ?
