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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/7/15/06/7150611.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_7150611
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         'C20 H16 N2 O4'
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.36
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      20
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             06-01-24
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3958(2)
_cell_length_b                   9.9699(2)
_cell_length_c                   19.6247(5)
_cell_measurement_reflns_used    1091
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     1642.69(7)
_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, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12353
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0995
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_coef       0.127(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0607P)²+0.7644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1000
_reflns_number_total             1086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b820551e.txt
_cod_data_source_block           SG0605
_cod_original_sg_symbol_H-M      'C 2 2 21 '
_cod_database_code               7150611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, -y+1/2, z+1/2'
'-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
O10 O 0.9313(2) 0.33729(17) 0.56913(8) 0.0317(5) Uani 1 1 d . . .
O11 O 0.7437(2) 0.20711(19) 0.61734(8) 0.0357(5) Uani 1 1 d . . .
N1 N 0.9650(2) 0.19717(19) 0.71955(9) 0.0269(5) Uani 1 1 d . . .
C2 C 0.9252(3) 0.3139(2) 0.69002(10) 0.0240(5) Uani 1 1 d . . .
C3 C 0.9552(3) 0.4390(2) 0.71926(11) 0.0228(5) Uani 1 1 d . . .
C4 C 0.9185(3) 0.5785(2) 0.70117(11) 0.0236(5) Uani 1 1 d . . .
C5 C 0.8237(3) 0.6411(2) 0.65277(12) 0.0275(5) Uani 1 1 d . . .
C6 C 0.8228(3) 0.7848(3) 0.65341(12) 0.0310(6) Uani 1 1 d . . .
H6 H 0.7601 0.8301 0.6203 0.037 Uiso 1 1 calc R . .
C7 C 0.9073(3) 0.8605(2) 0.69921(12) 0.0315(6) Uani 1 1 d . . .
H7 H 0.9037 0.9556 0.6968 0.038 Uiso 1 1 calc R . .
C8 C 1.0000 0.7968(3) 0.7500 0.0275(7) Uani 1 2 d S . .
C9 C 1.0000 0.6562(3) 0.7500 0.0257(7) Uani 1 2 d S . .
C10 C 0.8667(3) 0.2908(2) 0.61862(11) 0.0257(5) Uani 1 1 d . . .
C12 C 0.6840(4) 0.1711(4) 0.55075(14) 0.0485(8) Uani 1 1 d . . .
H121 H 0.7727 0.1415 0.5219 0.073 Uiso 1 1 calc R . .
H122 H 0.6324 0.2491 0.5299 0.073 Uiso 1 1 calc R . .
H123 H 0.6065 0.0982 0.5552 0.073 Uiso 1 1 calc R . .
C13 C 0.7192(3) 0.5715(2) 0.60209(12) 0.0315(6) Uani 1 1 d . . .
H131 H 0.6727 0.4913 0.6230 0.047 Uiso 1 1 calc R . .
H132 H 0.7826 0.5454 0.5623 0.047 Uiso 1 1 calc R . .
H133 H 0.6338 0.6323 0.5878 0.047 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 80 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 64 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
;
O O 16 0.0106 0.0060
; 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
C10 O11 C12 116.3(2) . . ?
N1 N1 C2 119.81(12) 4_756 . ?
N1 C2 C3 123.52(19) . . ?
N1 C2 C10 110.53(19) . . ?
C3 C2 C10 125.4(2) . . ?
C2 C3 C3 116.39(13) . 4_756 ?
C2 C3 C4 135.2(2) . . ?
C3 C3 C4 108.44(12) 4_756 . ?
C5 C4 C9 119.8(2) . . ?
C5 C4 C3 135.4(2) . . ?
C9 C4 C3 104.7(2) . . ?
C4 C5 C6 116.5(2) . . ?
C4 C5 C13 125.7(2) . . ?
C6 C5 C13 117.8(2) . . ?
C7 C6 C5 123.6(2) . . ?
C7 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C6 C7 C8 119.9(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 116.67(15) . . ?
C7 C8 C7 126.7(3) . 4_756 ?
C8 C9 C4 123.35(14) . . ?
C4 C9 C4 113.3(3) . 4_756 ?
O10 C10 O11 125.2(2) . . ?
O10 C10 C2 123.1(2) . . ?
O11 C10 C2 111.60(18) . . ?
O11 C12 H121 109.5 . . ?
O11 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
O11 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
C5 C13 H131 109.5 . . ?
C5 C13 H132 109.5 . . ?
H131 C13 H132 109.5 . . ?
C5 C13 H133 109.5 . . ?
H131 C13 H133 109.5 . . ?
H132 C13 H133 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
O10 C10 1.205(3) . ?
O11 C10 1.328(3) . ?
O11 C12 1.445(3) . ?
N1 N1 1.332(4) 4_756 ?
N1 C2 1.343(3) . ?
C2 C3 1.396(3) . ?
C2 C10 1.502(3) . ?
C3 C3 1.422(4) 4_756 ?
C3 C4 1.468(3) . ?
C4 C5 1.387(3) . ?
C4 C9 1.410(3) . ?
C5 C6 1.433(3) . ?
C5 C13 1.497(3) . ?
C6 C7 1.372(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(4) . ?
C12 H121 0.9800 . ?
C12 H122 0.9800 . ?
C12 H123 0.9800 . ?
C13 H131 0.9800 . ?
C13 H132 0.9800 . ?
C13 H133 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 1.0(4) 4_756 . . . ?
N1 N1 C2 C10 173.1(2) 4_756 . . . ?
N1 C2 C3 C3 5.5(4) . . . 4_756 ?
C10 C2 C3 C3 -165.4(2) . . . 4_756 ?
N1 C2 C3 C4 -176.0(3) . . . . ?
C10 C2 C3 C4 13.1(4) . . . . ?
C2 C3 C4 C5 9.6(5) . . . . ?
C3 C3 C4 C5 -171.8(3) 4_756 . . . ?
C2 C3 C4 C9 -173.8(2) . . . . ?
C3 C3 C4 C9 4.8(3) 4_756 . . . ?
C9 C4 C5 C6 3.6(3) . . . . ?
C3 C4 C5 C6 179.8(2) . . . . ?
C9 C4 C5 C13 -174.14(19) . . . . ?
C3 C4 C5 C13 2.1(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C13 C5 C6 C7 176.9(2) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C6 C7 C8 C7 -179.7(2) . . . 4_756 ?
C7 C8 C9 C4 2.44(16) . . . . ?
C7 C8 C9 C4 -177.56(16) . . . 4_756 ?
C5 C4 C9 C8 -4.5(2) . . . . ?
C3 C4 C9 C8 178.21(10) . . . . ?
C5 C4 C9 C4 175.5(2) . . . 4_756 ?
C3 C4 C9 C4 -1.79(10) . . . 4_756 ?
C12 O11 C10 O10 -0.4(4) . . . . ?
C12 O11 C10 C2 -176.3(2) . . . . ?
N1 C2 C10 O10 -118.8(3) . . . . ?
C3 C2 C10 O10 53.1(3) . . . . ?
N1 C2 C10 O11 57.2(3) . . . . ?
C3 C2 C10 O11 -130.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 42638863
