#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/06/7150601.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_7150601
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 O2, 2(C H Cl3)'
_chemical_formula_sum            'C30 H22 Cl6 N2 O2'
_chemical_formula_weight         655.23
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             07-06-19
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.0695(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6105(4)
_cell_length_b                   18.4987(4)
_cell_length_c                   11.5185(3)
_cell_measurement_reflns_used    22530
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     2924.12(13)
_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  0.0894
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38403
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0598
_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)+(0.0746P)²+3.6131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1608
_reflns_number_gt                2786
_reflns_number_total             4282
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b820551e.txt
_cod_data_source_block           SG0727
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               7150601
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
O1 O 0.52502(10) 0.43979(8) -0.05704(13) 0.0236(3) Uani 1 1 d . . .
H1 H 0.526(2) 0.4780(16) -0.101(3) 0.042(8) Uiso 1 1 d . . .
N1 N 0.47906(12) 0.42974(9) 0.18812(15) 0.0208(4) Uani 1 1 d . . .
C2 C 0.46398(14) 0.36722(10) 0.12436(18) 0.0199(4) Uani 1 1 d . . .
C3 C 0.48879(14) 0.30091(10) 0.18543(18) 0.0203(4) Uani 1 1 d . . .
C4 C 0.48992(14) 0.22533(11) 0.1438(2) 0.0249(4) Uani 1 1 d . . .
C5 C 0.49092(16) 0.19197(13) 0.0364(2) 0.0332(5) Uani 1 1 d . . .
C6 C 0.49592(19) 0.11463(14) 0.0393(3) 0.0451(7) Uani 1 1 d . . .
H6 H 0.4975 0.0902 -0.0325 0.054 Uiso 1 1 calc R . .
C7 C 0.4985(2) 0.07402(13) 0.1395(3) 0.0494(7) Uani 1 1 d . . .
H7 H 0.4993 0.0228 0.1344 0.059 Uiso 1 1 calc R . .
C8 C 0.5000 0.10719(16) 0.2500 0.0377(8) Uani 1 2 d S . .
C9 C 0.5000 0.18337(16) 0.2500 0.0275(6) Uani 1 2 d S . .
C10 C 0.40456(14) 0.37217(11) -0.00946(18) 0.0218(4) Uani 1 1 d . . .
C11 C 0.43340(14) 0.41079(11) -0.09530(18) 0.0221(4) Uani 1 1 d . . .
C12 C 0.37105(16) 0.41500(13) -0.2178(2) 0.0310(5) Uani 1 1 d . . .
H12 H 0.3896 0.4423 -0.2759 0.037 Uiso 1 1 calc R . .
C13 C 0.28219(17) 0.37953(14) -0.2551(2) 0.0366(5) Uani 1 1 d . . .
H13 H 0.2402 0.3826 -0.3387 0.044 Uiso 1 1 calc R . .
C14 C 0.25422(17) 0.33958(14) -0.1713(2) 0.0337(5) Uani 1 1 d . . .
H14 H 0.1939 0.3144 -0.1974 0.040 Uiso 1 1 calc R . .
C15 C 0.31498(15) 0.33662(12) -0.0493(2) 0.0267(4) Uani 1 1 d . . .
H15 H 0.2953 0.3099 0.0086 0.032 Uiso 1 1 calc R . .
C16 C 0.4914(2) 0.22936(15) -0.0790(2) 0.0409(6) Uani 1 1 d . . .
H161 H 0.4242 0.2386 -0.1329 0.061 Uiso 1 1 calc R . .
H162 H 0.5238 0.1985 -0.1224 0.061 Uiso 1 1 calc R . .
H163 H 0.5265 0.2753 -0.0572 0.061 Uiso 1 1 calc R . .
Cl1 Cl 0.79377(7) 0.46471(5) 0.08990(9) 0.0690(3) Uani 1 1 d . . .
Cl2 Cl 0.76344(7) 0.41182(6) 0.30921(7) 0.0723(3) Uani 1 1 d . . .
Cl3 Cl 0.73856(8) 0.31650(5) 0.10389(9) 0.0735(3) Uani 1 1 d . . .
C17 C 0.72743(18) 0.40586(15) 0.1486(2) 0.0400(6) Uani 1 1 d . . .
H17 H 0.6572 0.4199 0.1132 0.048 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 120 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 88 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Cl Cl 24 0.1484 0.1585
; 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 8 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
C11 O1 H1 109.5(19) . . ?
N1 N1 C2 120.52(11) 2_655 . ?
N1 C2 C3 120.87(17) . . ?
N1 C2 C10 116.07(17) . . ?
C3 C2 C10 122.20(17) . . ?
C2 C3 C3 117.21(12) . 2_655 ?
C2 C3 C4 134.05(18) . . ?
C3 C3 C4 108.52(12) 2_655 . ?
C5 C4 C9 119.9(2) . . ?
C5 C4 C3 135.6(2) . . ?
C9 C4 C3 104.34(18) . . ?
C4 C5 C6 116.1(2) . . ?
C4 C5 C16 126.1(2) . . ?
C6 C5 C16 117.7(2) . . ?
C7 C6 C5 123.7(2) . . ?
C7 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C7 128.3(3) . 2_655 ?
C7 C8 C9 115.86(16) . . ?
C8 C9 C4 123.31(13) . . ?
C4 C9 C4 113.4(3) . 2_655 ?
C15 C10 C11 119.05(18) . . ?
C15 C10 C2 117.33(18) . . ?
C11 C10 C2 123.61(17) . . ?
O1 C11 C12 122.12(18) . . ?
O1 C11 C10 118.18(17) . . ?
C12 C11 C10 119.59(19) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
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 . . ?
Cl1 C17 Cl2 111.52(15) . . ?
Cl1 C17 Cl3 110.77(16) . . ?
Cl2 C17 Cl3 110.26(15) . . ?
Cl1 C17 H17 108.1 . . ?
Cl2 C17 H17 108.1 . . ?
Cl3 C17 H17 108.1 . . ?
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 C11 1.367(2) . ?
O1 H1 0.87(3) . ?
N1 N1 1.345(3) 2_655 ?
N1 C2 1.347(3) . ?
C2 C3 1.399(3) . ?
C2 C10 1.490(3) . ?
C3 C3 1.409(4) 2_655 ?
C3 C4 1.480(3) . ?
C4 C5 1.386(3) . ?
C4 C9 1.413(3) . ?
C5 C6 1.432(3) . ?
C5 C16 1.501(4) . ?
C6 C7 1.366(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(4) . ?
C10 C15 1.394(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H161 0.9800 . ?
C16 H162 0.9800 . ?
C16 H163 0.9800 . ?
Cl1 C17 1.741(3) . ?
Cl2 C17 1.744(3) . ?
Cl3 C17 1.756(3) . ?
C17 H17 1.0000 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.87(3) 1.97(3) 2.837(2) 174(3) 5_665 yes
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 1.9(3) 2_655 . . . ?
N1 N1 C2 C10 171.5(2) 2_655 . . . ?
N1 C2 C3 C3 12.4(3) . . . 2_655 ?
C10 C2 C3 C3 -156.5(2) . . . 2_655 ?
N1 C2 C3 C4 -173.6(2) . . . . ?
C10 C2 C3 C4 17.4(3) . . . . ?
C2 C3 C4 C5 19.4(4) . . . . ?
C3 C3 C4 C5 -166.3(2) 2_655 . . . ?
C2 C3 C4 C9 -166.5(2) . . . . ?
C3 C3 C4 C9 7.9(2) 2_655 . . . ?
C9 C4 C5 C6 4.0(3) . . . . ?
C3 C4 C5 C6 177.5(2) . . . . ?
C9 C4 C5 C16 -173.31(19) . . . . ?
C3 C4 C5 C16 0.2(4) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C16 C5 C6 C7 178.3(3) . . . . ?
C5 C6 C7 C8 -2.4(4) . . . . ?
C6 C7 C8 C7 179.2(3) . . . 2_655 ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C4 5.79(16) . . . . ?
C7 C8 C9 C4 -174.21(16) 2_655 . . . ?
C7 C8 C9 C4 -174.21(16) . . . 2_655 ?
C7 C8 C9 C4 5.79(16) 2_655 . . 2_655 ?
C5 C4 C9 C8 -7.6(2) . . . . ?
C3 C4 C9 C8 177.11(9) . . . . ?
C5 C4 C9 C4 172.4(2) . . . 2_655 ?
C3 C4 C9 C4 -2.88(9) . . . 2_655 ?
N1 C2 C10 C15 -115.4(2) . . . . ?
C3 C2 C10 C15 54.1(3) . . . . ?
N1 C2 C10 C11 63.9(3) . . . . ?
C3 C2 C10 C11 -126.6(2) . . . . ?
C15 C10 C11 O1 -174.20(18) . . . . ?
C2 C10 C11 O1 6.5(3) . . . . ?
C15 C10 C11 C12 2.1(3) . . . . ?
C2 C10 C11 C12 -177.22(19) . . . . ?
O1 C11 C12 C13 174.3(2) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C13 C14 C15 C10 -1.0(4) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C2 C10 C15 C14 178.7(2) . . . . ?
