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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150599.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_7150599
loop_
_publ_author_name
'Rahanyan, Nelli'
'Linden, Anthony'
'Baldridge, Kim K.'
'Siegel, Jay S.'
_publ_section_title
;
 Diels--Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines.
 Synthesis and X-ray crystal structures of diazafluoranthene
 derivatives
;
_journal_issue                   10
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2082
_journal_page_last               2092
_journal_paper_doi               10.1039/b820551e
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C28 H20 N2'
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.48
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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_date             07-03-30
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.6642(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.7712(6)
_cell_length_b                   9.9895(3)
_cell_length_c                   9.2316(3)
_cell_measurement_reflns_used    2957
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1942.32(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29059
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0769
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0609
_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)+(0.0895P)²+0.9433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2042
_reflns_number_total             2827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b820551e.txt
_cod_data_source_block           SG0714
_cod_database_code               7150599
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.47151(6) 0.42404(13) 0.76415(16) 0.0285(3) Uani 1 1 d . . .
C2 C 0.44335(7) 0.30904(14) 0.78610(16) 0.0189(3) Uani 1 1 d . . .
C3 C 0.47233(6) 0.18485(13) 0.77729(14) 0.0150(3) Uani 1 1 d . . .
C4 C 0.45663(6) 0.04482(14) 0.80530(14) 0.0143(3) Uani 1 1 d . . .
C5 C 0.41479(6) -0.01963(15) 0.87409(14) 0.0157(3) Uani 1 1 d . . .
C6 C 0.41562(7) -0.16212(15) 0.87414(16) 0.0193(3) Uani 1 1 d . . .
H6 H 0.3867 -0.2074 0.9189 0.023 Uiso 1 1 calc R . .
C7 C 0.45531(7) -0.23843(15) 0.81394(16) 0.0204(3) Uani 1 1 d . . .
H7 H 0.4528 -0.3334 0.8152 0.024 Uiso 1 1 calc R . .
C8 C 0.5000 -0.17401(19) 0.7500 0.0168(4) Uani 1 2 d S . .
C9 C 0.5000 -0.03416(19) 0.7500 0.0145(4) Uani 1 2 d S . .
C10 C 0.37896(7) 0.32912(14) 0.80976(17) 0.0205(3) Uani 1 1 d . . .
C11 C 0.37001(9) 0.40894(17) 0.9269(2) 0.0321(4) Uani 1 1 d . . .
H11 H 0.4053 0.4506 0.9934 0.039 Uiso 1 1 calc R . .
C12 C 0.30942(10) 0.4273(2) 0.9460(2) 0.0417(5) Uani 1 1 d . . .
H12 H 0.3036 0.4803 1.0268 0.050 Uiso 1 1 calc R . .
C13 C 0.25748(9) 0.3692(2) 0.8487(2) 0.0393(5) Uani 1 1 d . . .
H13 H 0.2162 0.3820 0.8630 0.047 Uiso 1 1 calc R . .
C14 C 0.26565(8) 0.29234(19) 0.73036(19) 0.0325(4) Uani 1 1 d . . .
H14 H 0.2300 0.2534 0.6622 0.039 Uiso 1 1 calc R . .
C15 C 0.32646(7) 0.27234(17) 0.71172(17) 0.0243(4) Uani 1 1 d . . .
H15 H 0.3321 0.2191 0.6308 0.029 Uiso 1 1 calc R . .
C16 C 0.36996(7) 0.04629(15) 0.95210(16) 0.0203(3) Uani 1 1 d . . .
H161 H 0.3878 0.1321 0.9942 0.030 Uiso 1 1 calc R . .
H162 H 0.3639 -0.0119 1.0328 0.030 Uiso 1 1 calc R . .
H163 H 0.3290 0.0616 0.8801 0.030 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 112 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 80 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 8 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
N1 N1 C2 120.93(8) 2_656 . ?
N1 C2 C3 121.25(13) . . ?
N1 C2 C10 113.01(12) . . ?
C3 C2 C10 125.63(13) . . ?
C2 C3 C3 117.08(8) . 2_656 ?
C2 C3 C4 134.35(13) . . ?
C3 C3 C4 108.47(7) 2_656 . ?
C5 C4 C9 118.54(13) . . ?
C5 C4 C3 136.38(13) . . ?
C9 C4 C3 104.99(12) . . ?
C4 C5 C6 116.91(12) . . ?
C4 C5 C16 126.48(13) . . ?
C6 C5 C16 116.59(12) . . ?
C7 C6 C5 124.41(13) . . ?
C7 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
C6 C7 C8 119.14(14) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 117.07(9) . . ?
C7 C8 C7 125.86(19) 2_656 . ?
C8 C9 C4 123.73(9) . . ?
C4 C9 C4 112.53(17) 2_656 . ?
C15 C10 C11 119.03(15) . . ?
C15 C10 C2 120.08(13) . . ?
C11 C10 C2 120.85(15) . . ?
C12 C11 C10 119.83(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.71(16) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.93(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 119.60(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 120.88(15) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C5 C16 H161 109.5 . . ?
C5 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
C5 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 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
N1 N1 1.331(3) 2_656 ?
N1 C2 1.341(2) . ?
C2 C3 1.4035(19) . ?
C2 C10 1.486(2) . ?
C3 C3 1.419(3) 2_656 ?
C3 C4 1.4781(19) . ?
C4 C5 1.3930(18) . ?
C4 C9 1.4208(17) . ?
C5 C6 1.423(2) . ?
C5 C16 1.5036(19) . ?
C6 C7 1.371(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4142(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(3) . ?
C10 C15 1.387(2) . ?
C10 C11 1.397(2) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H161 0.9800 . ?
C16 H162 0.9800 . ?
C16 H163 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
N1 N1 C2 C3 -1.2(3) 2_656 . . . ?
N1 N1 C2 C10 -177.58(17) 2_656 . . . ?
N1 C2 C3 C3 -9.1(2) . . . 2_656 ?
C10 C2 C3 C3 166.79(15) . . . 2_656 ?
N1 C2 C3 C4 174.87(14) . . . . ?
C10 C2 C3 C4 -9.2(3) . . . . ?
C2 C3 C4 C5 -13.6(3) . . . . ?
C3 C3 C4 C5 170.14(15) 2_656 . . . ?
C2 C3 C4 C9 170.05(14) . . . . ?
C3 C3 C4 C9 -6.20(16) 2_656 . . . ?
C9 C4 C5 C6 -4.42(17) . . . . ?
C3 C4 C5 C6 179.61(14) . . . . ?
C9 C4 C5 C16 173.81(11) . . . . ?
C3 C4 C5 C16 -2.2(2) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C16 C5 C6 C7 -177.18(13) . . . . ?
C5 C6 C7 C8 1.6(2) . . . . ?
C6 C7 C8 C9 -1.13(15) . . . . ?
C6 C7 C8 C7 178.87(15) . . . 2_656 ?
C7 C8 C9 C4 -2.26(9) 2_656 . . 2_656 ?
C7 C8 C9 C4 177.74(9) . . . 2_656 ?
C7 C8 C9 C4 -2.26(9) . . . . ?
C5 C4 C9 C8 5.17(13) . . . . ?
C3 C4 C9 C8 -177.71(6) . . . . ?
C5 C4 C9 C4 -174.84(13) . . . 2_656 ?
C3 C4 C9 C4 2.29(6) . . . 2_656 ?
N1 C2 C10 C15 119.19(16) . . . . ?
C3 C2 C10 C15 -57.0(2) . . . . ?
N1 C2 C10 C11 -58.45(19) . . . . ?
C3 C2 C10 C11 125.35(17) . . . . ?
C15 C10 C11 C12 1.7(2) . . . . ?
C2 C10 C11 C12 179.39(16) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C11 C10 C15 C14 -1.0(2) . . . . ?
C2 C10 C15 C14 -178.68(14) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 42638691
