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#$Date: 2016-03-26 15:11:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180292 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150607.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_7150607
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         'C24 H16 N2 S2'
_chemical_formula_sum            'C24 H16 N2 S2'
_chemical_formula_weight         396.52
_chemical_name_systematic
;
?
;
_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             07-05-07
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.1223(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8710(2)
_cell_length_b                   10.0494(2)
_cell_length_c                   21.2597(5)
_cell_measurement_reflns_used    20788
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     1853.00(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, 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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16306
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.10
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0552
_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)+(0.0765P)²+2.6024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                1655
_reflns_number_total             2108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b820551e.txt
_cod_data_source_block           SG0715
_cod_database_code               7150607
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 0.5145(2) 0.36115(16) 0.22063(8) 0.0218(4) Uani 1 1 d . . .
C2 C 0.5377(2) 0.24620(19) 0.19160(9) 0.0173(4) Uani 1 1 d . A .
C3 C 0.5298(2) 0.12280(19) 0.22159(9) 0.0161(4) Uani 1 1 d . . .
C4 C 0.5605(2) -0.01597(19) 0.20554(9) 0.0162(4) Uani 1 1 d . . .
C5 C 0.6383(2) -0.0789(2) 0.16349(9) 0.0186(4) Uani 1 1 d . . .
C6 C 0.6404(2) -0.2210(2) 0.16485(10) 0.0207(5) Uani 1 1 d . . .
H6 H 0.6919 -0.2659 0.1361 0.025 Uiso 1 1 calc R . .
C7 C 0.5731(2) -0.2966(2) 0.20487(10) 0.0217(5) Uani 1 1 d . . .
H7 H 0.5753 -0.3909 0.2024 0.026 Uiso 1 1 calc R . .
C8 C 0.5000 -0.2334(3) 0.2500 0.0191(6) Uani 1 2 d S . .
C9 C 0.5000 -0.0942(3) 0.2500 0.0161(6) Uani 1 2 d S . .
C10 C 0.5549(2) 0.26550(19) 0.12506(10) 0.0215(5) Uani 1 1 d D . .
S11 S 0.66770(16) 0.38731(11) 0.10396(6) 0.0350(3) Uani 0.767(3) 1 d PDU A 1
C12 C 0.6068(5) 0.3526(5) 0.02352(17) 0.0386(9) Uani 0.767(3) 1 d PDU A 1
H12 H 0.6428 0.3975 -0.0098 0.046 Uiso 0.767(3) 1 calc PR A 1
C13 C 0.5012(5) 0.2533(4) 0.01339(18) 0.0347(8) Uani 0.767(3) 1 d PDU A 1
H13 H 0.4543 0.2206 -0.0280 0.042 Uiso 0.767(3) 1 calc PR A 1
C14 C 0.4677(12) 0.2028(11) 0.0723(3) 0.0272(12) Uani 0.767(3) 1 d PDU A 1
H14 H 0.3946 0.1347 0.0745 0.033 Uiso 0.767(3) 1 calc PR A 1
S11A S 0.4451(10) 0.1965(10) 0.0590(3) 0.0319(12) Uani 0.233(3) 1 d PDU A 2
C12A C 0.5329(16) 0.2885(14) 0.0087(4) 0.0352(18) Uani 0.233(3) 1 d PDU A 2
H12A H 0.5039 0.2862 -0.0369 0.042 Uiso 0.233(3) 1 calc PR A 2
C13A C 0.6486(16) 0.3646(15) 0.0421(5) 0.0364(16) Uani 0.233(3) 1 d PDU A 2
H13A H 0.7138 0.4186 0.0226 0.044 Uiso 0.233(3) 1 calc PR A 2
C14A C 0.661(2) 0.3544(18) 0.1107(6) 0.038(2) Uani 0.233(3) 1 d PDU A 2
H14A H 0.7336 0.4023 0.1418 0.046 Uiso 0.233(3) 1 calc PR A 2
C15 C 0.7256(3) -0.0100(2) 0.11927(11) 0.0250(5) Uani 1 1 d . . .
H151 H 0.6566 0.0055 0.0775 0.037 Uiso 1 1 calc R . .
H152 H 0.8121 -0.0660 0.1134 0.037 Uiso 1 1 calc R . .
H153 H 0.7650 0.0754 0.1381 0.037 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 96 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
;
S S 8 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
N1 N1 C2 120.67(11) 2_655 . ?
N1 C2 C3 121.57(18) . . ?
N1 C2 C10 112.68(17) . . ?
C3 C2 C10 125.46(18) . . ?
C2 C3 C3 116.77(12) . 2_655 ?
C2 C3 C4 134.57(18) . . ?
C3 C3 C4 108.50(11) 2_655 . ?
C5 C4 C9 118.96(18) . . ?
C5 C4 C3 136.02(18) . . ?
C9 C4 C3 104.83(17) . . ?
C4 C5 C6 116.62(18) . . ?
C4 C5 C15 125.54(18) . . ?
C6 C5 C15 117.78(18) . . ?
C7 C6 C5 124.21(19) . . ?
C7 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 116.66(13) . . ?
C7 C8 C7 126.7(3) 2_655 . ?
C8 C9 C4 123.65(12) . . ?
C4 C9 C4 112.7(2) 2_655 . ?
C14 C10 C2 124.8(4) . . ?
C14A C10 C2 120.9(6) . . ?
C14A C10 S11A 112.6(4) . . ?
C2 C10 S11A 126.3(3) . . ?
C14 C10 S11 112.1(4) . . ?
C2 C10 S11 122.40(15) . . ?
C10 S11 C12 92.11(17) . . ?
C13 C12 S11 111.7(3) . . ?
C13 C12 H12 124.1 . . ?
S11 C12 H12 124.1 . . ?
C12 C13 C14 112.6(4) . . ?
C12 C13 H13 123.7 . . ?
C14 C13 H13 123.7 . . ?
C10 C14 C13 111.4(6) . . ?
C10 C14 H14 124.3 . . ?
C13 C14 H14 124.3 . . ?
C10 S11A C12A 92.2(3) . . ?
C13A C12A S11A 111.7(5) . . ?
C13A C12A H12A 124.1 . . ?
S11A C12A H12A 124.1 . . ?
C12A C13A C14A 112.3(6) . . ?
C12A C13A H13A 123.8 . . ?
C14A C13A H13A 123.8 . . ?
C10 C14A C13A 111.0(7) . . ?
C10 C14A H14A 124.5 . . ?
C13A C14A H14A 124.5 . . ?
C5 C15 H151 109.5 . . ?
C5 C15 H152 109.5 . . ?
H151 C15 H152 109.5 . . ?
C5 C15 H153 109.5 . . ?
H151 C15 H153 109.5 . . ?
H152 C15 H153 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 1.327(3) 2_655 ?
N1 C2 1.346(3) . ?
C2 C3 1.403(3) . ?
C2 C10 1.467(3) . ?
C3 C3 1.417(4) 2_655 ?
C3 C4 1.475(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.419(2) . ?
C5 C6 1.428(3) . ?
C5 C15 1.507(3) . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.416(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(4) . ?
C10 C14 1.374(7) . ?
C10 C14A 1.381(8) . ?
C10 S11A 1.682(4) . ?
C10 S11 1.700(2) . ?
S11 C12 1.717(4) . ?
C12 C13 1.355(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.439(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
S11A C12A 1.718(6) . ?
C12A C13A 1.356(7) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.441(10) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15 H151 0.9800 . ?
C15 H152 0.9800 . ?
C15 H153 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 0.9(4) 2_655 . . . ?
N1 N1 C2 C10 175.1(2) 2_655 . . . ?
N1 C2 C3 C3 10.8(3) . . . 2_655 ?
C10 C2 C3 C3 -162.6(2) . . . 2_655 ?
N1 C2 C3 C4 -174.3(2) . . . . ?
C10 C2 C3 C4 12.3(4) . . . . ?
C2 C3 C4 C5 16.8(4) . . . . ?
C3 C3 C4 C5 -168.0(2) 2_655 . . . ?
C2 C3 C4 C9 -168.5(2) . . . . ?
C3 C3 C4 C9 6.7(2) 2_655 . . . ?
C9 C4 C5 C6 5.0(3) . . . . ?
C3 C4 C5 C6 179.1(2) . . . . ?
C9 C4 C5 C15 -172.08(17) . . . . ?
C3 C4 C5 C15 2.0(4) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C15 C5 C6 C7 176.6(2) . . . . ?
C5 C6 C7 C8 -2.3(3) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C6 C7 C8 C7 -179.2(2) . . . 2_655 ?
C7 C8 C9 C4 3.66(13) 2_655 . . 2_655 ?
C7 C8 C9 C4 -176.34(13) . . . 2_655 ?
C7 C8 C9 C4 -176.34(13) 2_655 . . . ?
C7 C8 C9 C4 3.66(13) . . . . ?
C5 C4 C9 C8 -6.7(2) . . . . ?
C3 C4 C9 C8 177.53(9) . . . . ?
C5 C4 C9 C4 173.3(2) . . . 2_655 ?
C3 C4 C9 C4 -2.47(9) . . . 2_655 ?
N1 C2 C10 C14 -125.0(7) . . . . ?
C3 C2 C10 C14 48.9(7) . . . . ?
N1 C2 C10 C14A 53.2(12) . . . . ?
C3 C2 C10 C14A -132.9(12) . . . . ?
N1 C2 C10 S11A -121.8(5) . . . . ?
C3 C2 C10 S11A 52.1(6) . . . . ?
N1 C2 C10 S11 45.2(2) . . . . ?
C3 C2 C10 S11 -140.91(19) . . . . ?
C14 C10 S11 C12 -2.4(6) . . . . ?
C2 C10 S11 C12 -173.7(2) . . . . ?
C10 S11 C12 C13 1.4(4) . . . . ?
S11 C12 C13 C14 -0.1(8) . . . . ?
C2 C10 C14 C13 173.8(5) . . . . ?
S11 C10 C14 C13 2.7(10) . . . . ?
C12 C13 C14 C10 -1.7(11) . . . . ?
C14A C10 S11A C12A -2.0(14) . . . . ?
C2 C10 S11A C12A 173.3(6) . . . . ?
C10 S11A C12A C13A 3.1(15) . . . . ?
S11A C12A C13A C14A -3(2) . . . . ?
C2 C10 C14A C13A -175.2(11) . . . . ?
S11A C10 C14A C13A 0(2) . . . . ?
C12A C13A C14A C10 2(2) . . . . ?
