#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/05/7150597.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_7150597
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         'C18 H16 N2 S2'
_chemical_formula_sum            'C18 H16 N2 S2'
_chemical_formula_weight         324.46
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_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_date             07-09-24
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.9648(11)
_cell_angle_beta                 105.3063(12)
_cell_angle_gamma                95.0213(9)
_cell_formula_units_Z            2
_cell_length_a                   7.5950(1)
_cell_length_b                   10.1858(2)
_cell_length_c                   10.5743(2)
_cell_measurement_reflns_used    53689
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     747.20(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21179
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0563
_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)+(0.0845P)²+0.5561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                3454
_reflns_number_total             4352
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b820551e.txt
_cod_data_source_block           SG0733
_cod_original_cell_volume        747.19(2)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7150597
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
S1 S 0.13299(8) 0.23598(5) -0.36295(5) 0.02177(15) Uani 1 1 d . . .
S2 S 0.32927(9) 0.43289(5) 0.27429(5) 0.02325(16) Uani 1 1 d . . .
N1 N 0.2608(3) 0.45661(18) 0.02555(18) 0.0211(4) Uani 1 1 d . . .
N2 N 0.2179(3) 0.41554(18) -0.11306(18) 0.0212(4) Uani 1 1 d . . .
C3 C 0.2146(3) 0.28384(19) -0.18214(19) 0.0152(4) Uani 1 1 d . . .
C4 C 0.2525(3) 0.18238(19) -0.11462(19) 0.0126(3) Uani 1 1 d . . .
C5 C 0.2677(3) 0.03459(19) -0.16153(19) 0.0130(3) Uani 1 1 d . . .
C6 C 0.3014(3) -0.0557(2) -0.27531(19) 0.0151(4) Uani 1 1 d . . .
C7 C 0.3024(3) -0.1960(2) -0.2780(2) 0.0182(4) Uani 1 1 d . . .
H7 H 0.3211 -0.2591 -0.3562 0.022 Uiso 1 1 calc R . .
C8 C 0.2781(3) -0.2459(2) -0.1745(2) 0.0186(4) Uani 1 1 d . . .
H8 H 0.2770 -0.3413 -0.1831 0.022 Uiso 1 1 calc R . .
C9 C 0.2547(3) -0.15410(19) -0.0552(2) 0.0157(4) Uani 1 1 d . . .
C10 C 0.2316(3) -0.1899(2) 0.0601(2) 0.0189(4) Uani 1 1 d . . .
H10 H 0.2301 -0.2827 0.0620 0.023 Uiso 1 1 calc R . .
C11 C 0.2112(3) -0.0889(2) 0.1694(2) 0.0178(4) Uani 1 1 d . . .
H11 H 0.1923 -0.1154 0.2448 0.021 Uiso 1 1 calc R . .
C12 C 0.2167(3) 0.0531(2) 0.17664(19) 0.0147(4) Uani 1 1 d . . .
C13 C 0.2452(3) 0.09106(19) 0.06555(18) 0.0125(3) Uani 1 1 d . . .
C14 C 0.2556(3) 0.21947(19) 0.02537(19) 0.0129(3) Uani 1 1 d . . .
C15 C 0.2730(3) 0.3635(2) 0.09311(19) 0.0163(4) Uani 1 1 d . . .
C16 C 0.2567(3) -0.01526(19) -0.05019(18) 0.0129(3) Uani 1 1 d . . .
C17 C 0.1085(4) 0.3989(2) -0.3950(2) 0.0258(5) Uani 1 1 d . . .
H171 H 0.0289 0.4455 -0.3444 0.039 Uiso 1 1 calc R . .
H172 H 0.0526 0.3824 -0.4940 0.039 Uiso 1 1 calc R . .
H173 H 0.2307 0.4574 -0.3642 0.039 Uiso 1 1 calc R . .
C18 C 0.3461(3) -0.0177(2) -0.3924(2) 0.0202(4) Uani 1 1 d . . .
H181 H 0.2313 -0.0299 -0.4669 0.030 Uiso 1 1 calc R . .
H182 H 0.4284 -0.0776 -0.4268 0.030 Uiso 1 1 calc R . .
H183 H 0.4077 0.0793 -0.3598 0.030 Uiso 1 1 calc R . .
C19 C 0.1858(3) 0.1473(2) 0.3025(2) 0.0200(4) Uani 1 1 d . . .
H191 H 0.3050 0.2010 0.3661 0.030 Uiso 1 1 calc R . .
H192 H 0.1282 0.0919 0.3480 0.030 Uiso 1 1 calc R . .
H193 H 0.1042 0.2107 0.2755 0.030 Uiso 1 1 calc R . .
C20 C 0.3475(4) 0.6154(2) 0.2978(2) 0.0316(6) Uani 1 1 d . . .
H201 H 0.4332 0.6428 0.2510 0.047 Uiso 1 1 calc R . .
H202 H 0.3941 0.6668 0.3965 0.047 Uiso 1 1 calc R . .
H203 H 0.2251 0.6363 0.2587 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 36 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 32 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 4 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 4 0.1246 0.1234
; 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
C3 S1 C17 103.08(10) . . ?
C15 S2 C20 101.75(10) . . ?
C15 N1 N2 120.37(17) . . ?
C3 N2 N1 120.17(17) . . ?
N2 C3 C4 122.11(17) . . ?
N2 C3 S1 116.81(14) . . ?
C4 C3 S1 120.63(14) . . ?
C14 C4 C3 116.49(16) . . ?
C14 C4 C5 108.95(15) . . ?
C3 C4 C5 134.04(17) . . ?
C6 C5 C16 118.30(17) . . ?
C6 C5 C4 136.69(17) . . ?
C16 C5 C4 104.80(15) . . ?
C5 C6 C7 117.15(17) . . ?
C5 C6 C18 126.35(18) . . ?
C7 C6 C18 116.43(17) . . ?
C8 C7 C6 124.04(18) . . ?
C8 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C7 C8 C9 119.43(18) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C16 C9 C8 117.11(18) . . ?
C16 C9 C10 117.15(18) . . ?
C8 C9 C10 125.73(18) . . ?
C11 C10 C9 119.15(18) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 124.11(18) . . ?
C10 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C13 C12 C11 117.49(17) . . ?
C13 C12 C19 126.13(18) . . ?
C11 C12 C19 116.36(17) . . ?
C12 C13 C16 118.05(17) . . ?
C12 C13 C14 136.88(17) . . ?
C16 C13 C14 104.90(15) . . ?
C4 C14 C15 116.00(16) . . ?
C4 C14 C13 108.15(15) . . ?
C15 C14 C13 135.81(17) . . ?
N1 C15 C14 122.34(17) . . ?
N1 C15 S2 115.17(14) . . ?
C14 C15 S2 122.33(15) . . ?
C9 C16 C13 123.89(17) . . ?
C9 C16 C5 123.53(17) . . ?
C13 C16 C5 112.58(16) . . ?
S1 C17 H171 109.5 . . ?
S1 C17 H172 109.5 . . ?
H171 C17 H172 109.5 . . ?
S1 C17 H173 109.5 . . ?
H171 C17 H173 109.5 . . ?
H172 C17 H173 109.5 . . ?
C6 C18 H181 109.5 . . ?
C6 C18 H182 109.5 . . ?
H181 C18 H182 109.5 . . ?
C6 C18 H183 109.5 . . ?
H181 C18 H183 109.5 . . ?
H182 C18 H183 109.5 . . ?
C12 C19 H191 109.5 . . ?
C12 C19 H192 109.5 . . ?
H191 C19 H192 109.5 . . ?
C12 C19 H193 109.5 . . ?
H191 C19 H193 109.5 . . ?
H192 C19 H193 109.5 . . ?
S2 C20 H201 109.5 . . ?
S2 C20 H202 109.5 . . ?
H201 C20 H202 109.5 . . ?
S2 C20 H203 109.5 . . ?
H201 C20 H203 109.5 . . ?
H202 C20 H203 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
S1 C3 1.7567(19) . ?
S1 C17 1.798(2) . ?
S2 C15 1.7671(19) . ?
S2 C20 1.795(2) . ?
N1 C15 1.331(3) . ?
N1 N2 1.348(2) . ?
N2 C3 1.334(2) . ?
C3 C4 1.418(3) . ?
C4 C14 1.417(3) . ?
C4 C5 1.475(2) . ?
C5 C6 1.398(3) . ?
C5 C16 1.423(3) . ?
C6 C7 1.422(3) . ?
C6 C18 1.503(3) . ?
C7 C8 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(3) . ?
C8 H8 0.9500 . ?
C9 C16 1.399(3) . ?
C9 C10 1.414(3) . ?
C10 C11 1.373(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.423(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 C19 1.499(3) . ?
C13 C16 1.422(2) . ?
C13 C14 1.484(3) . ?
C14 C15 1.421(2) . ?
C17 H171 0.9800 . ?
C17 H172 0.9800 . ?
C17 H173 0.9800 . ?
C18 H181 0.9800 . ?
C18 H182 0.9800 . ?
C18 H183 0.9800 . ?
C19 H191 0.9800 . ?
C19 H192 0.9800 . ?
C19 H193 0.9800 . ?
C20 H201 0.9800 . ?
C20 H202 0.9800 . ?
C20 H203 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
C15 N1 N2 C3 -10.1(3) . . . . ?
N1 N2 C3 C4 1.0(3) . . . . ?
N1 N2 C3 S1 173.30(16) . . . . ?
C17 S1 C3 N2 7.7(2) . . . . ?
C17 S1 C3 C4 -179.85(17) . . . . ?
N2 C3 C4 C14 12.9(3) . . . . ?
S1 C3 C4 C14 -159.15(15) . . . . ?
N2 C3 C4 C5 -176.5(2) . . . . ?
S1 C3 C4 C5 11.5(3) . . . . ?
C14 C4 C5 C6 -167.5(2) . . . . ?
C3 C4 C5 C6 21.4(4) . . . . ?
C14 C4 C5 C16 6.9(2) . . . . ?
C3 C4 C5 C16 -164.2(2) . . . . ?
C16 C5 C6 C7 6.6(3) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C16 C5 C6 C18 -170.16(18) . . . . ?
C4 C5 C6 C18 3.6(4) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C18 C6 C7 C8 175.05(19) . . . . ?
C6 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C16 0.4(3) . . . . ?
C7 C8 C9 C10 -178.9(2) . . . . ?
C16 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C11 179.68(19) . . . . ?
C9 C10 C11 C12 -1.7(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C10 C11 C12 C19 178.18(19) . . . . ?
C11 C12 C13 C16 3.4(3) . . . . ?
C19 C12 C13 C16 -174.87(18) . . . . ?
C11 C12 C13 C14 177.8(2) . . . . ?
C19 C12 C13 C14 -0.4(4) . . . . ?
C3 C4 C14 C15 -17.1(3) . . . . ?
C5 C4 C14 C15 169.99(16) . . . . ?
C3 C4 C14 C13 164.66(17) . . . . ?
C5 C4 C14 C13 -8.2(2) . . . . ?
C12 C13 C14 C4 -168.8(2) . . . . ?
C16 C13 C14 C4 6.2(2) . . . . ?
C12 C13 C14 C15 13.6(4) . . . . ?
C16 C13 C14 C15 -171.5(2) . . . . ?
N2 N1 C15 C14 4.8(3) . . . . ?
N2 N1 C15 S2 -179.71(16) . . . . ?
C4 C14 C15 N1 9.1(3) . . . . ?
C13 C14 C15 N1 -173.3(2) . . . . ?
C4 C14 C15 S2 -166.04(15) . . . . ?
C13 C14 C15 S2 11.5(3) . . . . ?
C20 S2 C15 N1 0.5(2) . . . . ?
C20 S2 C15 C14 175.98(18) . . . . ?
C8 C9 C16 C13 -176.41(18) . . . . ?
C10 C9 C16 C13 2.9(3) . . . . ?
C8 C9 C16 C5 4.5(3) . . . . ?
C10 C9 C16 C5 -176.11(18) . . . . ?
C12 C13 C16 C9 -4.9(3) . . . . ?
C14 C13 C16 C9 179.02(18) . . . . ?
C12 C13 C16 C5 174.24(17) . . . . ?
C14 C13 C16 C5 -1.8(2) . . . . ?
C6 C5 C16 C9 -8.2(3) . . . . ?
C4 C5 C16 C9 176.16(18) . . . . ?
C6 C5 C16 C13 172.63(17) . . . . ?
C4 C5 C16 C13 -3.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25942871
