#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:37:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180513 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/82/7218239.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_7218239
loop_
_publ_author_name
'Benyei, Attila'
'Stirling, Andras'
'Bostai, Beatrix'
'Lőrincz, Krisztián'
'Kotschy, Andras'
_publ_section_title
;
 Out of cross-conjugation: The unexpected structure of tetrazinones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA05616G
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H20 N6 O'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.43
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_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             2014-09-10T08:35:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1590(10)
_cell_length_b                   18.715(2)
_cell_length_c                   15.977(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.3
_cell_measurement_theta_min      9.5
_cell_volume                     1841.6(4)
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_collection       'MACH3/PC (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0078
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1031
_diffrn_reflns_point_group_measured_fraction_full 0.572
_diffrn_reflns_point_group_measured_fraction_max 0.57
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.439
_diffrn_reflns_theta_min         2.522
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 167
_diffrn_standards_interval_time  120
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   2
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   5
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     130
_refine_ls_number_reflns         979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1262P)²+0.2486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                817
_reflns_number_total             979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra05616g2.cif
_cod_data_source_block           3
_cod_database_code               7218239
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
C3 0.5 0.2014(2) 0.25 0.0638(13) Uani d 1 C
C6 0.5 0.3396(2) 0.25 0.0411(9) Uani d 1 C
C12 0.5 0.4175(2) 0.25 0.0399(8) Uani d 1 C
C15 0.4128(6) 0.52965(15) 0.27509(17) 0.0509(8) Uani d 1 C
H15 0.3413 0.5697 0.2957 0.061 Uiso calc 1 H
C81 0.1887(5) 0.43385(15) 0.34938(16) 0.0458(7) Uani d 1 C
H81 0.0946 0.4004 0.3192 0.055 Uiso calc 1 H
C82 0.0506(5) 0.4961(2) 0.3790(2) 0.0607(9) Uani d 1 C
H82A 0.1381 0.528 0.4118 0.091 Uiso calc 1 H
H82B -0.0672 0.4785 0.4125 0.091 Uiso calc 1 H
H82C -0.0064 0.5212 0.3314 0.091 Uiso calc 1 H
C83 0.2876(5) 0.39474(14) 0.42299(16) 0.0434(7) Uani d 1 C
C84 0.4858(6) 0.41403(18) 0.45681(17) 0.0527(8) Uani d 1 C
H84 0.5692 0.449 0.4309 0.063 Uiso calc 1 H
C85 0.5604(6) 0.3814(2) 0.52907(19) 0.0607(9) Uani d 1 C
H85 0.6944 0.3945 0.5511 0.073 Uiso calc 1 H
C86 0.4390(7) 0.33014(18) 0.56848(19) 0.0635(10) Uani d 1 C
H86 0.4884 0.3091 0.6176 0.076 Uiso calc 1 H
C87 0.2437(8) 0.31027(18) 0.5345(2) 0.0658(10) Uani d 1 C
H87 0.1602 0.2753 0.5604 0.079 Uiso calc 1 H
C88 0.1712(6) 0.34207(17) 0.46209(19) 0.0565(9) Uani d 1 C
H88 0.0398 0.3274 0.4391 0.068 Uiso calc 1 H
N1 0.3098(4) 0.30724(13) 0.2410(2) 0.0598(8) Uani d 1 N
N2 0.3056(5) 0.23678(13) 0.2434(3) 0.0715(9) Uani d 1 N
N11 0.3590(4) 0.45964(12) 0.29045(13) 0.0442(6) Uani d 1 N
O1 0.5 0.1372(2) 0.25 0.137(2) Uani d 1 O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables 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
2 4 4
3 5 5
-1 5 -9
-2 3 -6
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
O1 C3 N2 118.85(18) . .
O1 C3 N2 118.85(18) . 4_655
N2 C3 N2 122.3(4) . 4_655
N1 C6 N1 125.6(4) . 4_655
N1 C6 C12 117.18(18) . .
N1 C6 C12 117.18(18) 4_655 .
N11 C12 N11 107.9(3) 4_655 .
N11 C12 C6 126.04(17) 4_655 .
N11 C12 C6 126.04(17) . .
C15 C15 N11 107.46(16) 4_655 .
C15 C15 H15 126.3 4_655 .
N11 C15 H15 126.3 . .
N11 C81 C83 111.4(3) . .
N11 C81 C82 110.0(2) . .
C83 C81 C82 110.8(2) . .
N11 C81 H81 108.2 . .
C83 C81 H81 108.2 . .
C82 C81 H81 108.2 . .
C81 C82 H82A 109.5 . .
C81 C82 H82B 109.5 . .
H82A C82 H82B 109.5 . .
C81 C82 H82C 109.5 . .
H82A C82 H82C 109.5 . .
H82B C82 H82C 109.5 . .
C88 C83 C84 118.1(3) . .
C88 C83 C81 119.5(3) . .
C84 C83 C81 122.2(3) . .
C83 C84 C85 120.3(3) . .
C83 C84 H84 119.9 . .
C85 C84 H84 119.9 . .
C86 C85 C84 120.7(3) . .
C86 C85 H85 119.6 . .
C84 C85 H85 119.6 . .
C85 C86 C87 119.1(3) . .
C85 C86 H86 120.4 . .
C87 C86 H86 120.4 . .
C86 C87 C88 120.0(3) . .
C86 C87 H87 120 . .
C88 C87 H87 120 . .
C83 C88 C87 121.7(3) . .
C83 C88 H88 119.2 . .
C87 C88 H88 119.2 . .
N2 N1 C6 118.1(3) . .
N1 N2 C3 117.9(3) . .
C12 N11 C15 108.6(2) . .
C12 N11 C81 124.8(2) . .
C15 N11 C81 126.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C3 O1 . 1.201(6)
C3 N2 . 1.372(4)
C3 N2 4_655 1.372(4)
C6 N1 . 1.327(3)
C6 N1 4_655 1.327(3)
C6 C12 . 1.458(5)
C12 N11 4_655 1.339(3)
C12 N11 . 1.339(3)
C15 C15 4_655 1.341(6)
C15 N11 . 1.374(4)
C15 H15 . 0.93
C81 N11 . 1.490(4)
C81 C83 . 1.513(4)
C81 C82 . 1.518(4)
C81 H81 . 0.98
C82 H82A . 0.96
C82 H82B . 0.96
C82 H82C . 0.96
C83 C88 . 1.370(4)
C83 C84 . 1.383(5)
C84 C85 . 1.384(4)
C84 H84 . 0.93
C85 C86 . 1.370(5)
C85 H85 . 0.93
C86 C87 . 1.371(6)
C86 H86 . 0.93
C87 C88 . 1.375(5)
C87 H87 . 0.93
C88 H88 . 0.93
N1 N2 . 1.319(3)
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_4
N1 C6 C12 N11 -136.4(2) . 4_655
N1 C6 C12 N11 43.6(2) 4_655 4_655
N1 C6 C12 N11 43.6(2) . .
N1 C6 C12 N11 -136.4(2) 4_655 .
N11 C81 C83 C88 -151.2(3) . .
C82 C81 C83 C88 85.9(3) . .
N11 C81 C83 C84 34.0(3) . .
C82 C81 C83 C84 -88.8(4) . .
C88 C83 C84 C85 -1.1(4) . .
C81 C83 C84 C85 173.7(3) . .
C83 C84 C85 C86 -0.5(5) . .
C84 C85 C86 C87 1.3(5) . .
C85 C86 C87 C88 -0.5(5) . .
C84 C83 C88 C87 2.0(5) . .
C81 C83 C88 C87 -172.9(3) . .
C86 C87 C88 C83 -1.2(5) . .
N1 C6 N1 N2 2.0(3) 4_655 .
C12 C6 N1 N2 -178.0(3) . .
C6 N1 N2 C3 -3.8(5) . .
O1 C3 N2 N1 -178.1(3) . .
N2 C3 N2 N1 1.9(3) 4_655 .
N11 C12 N11 C15 -0.04(15) 4_655 .
C6 C12 N11 C15 179.96(15) . .
N11 C12 N11 C81 -173.9(3) 4_655 .
C6 C12 N11 C81 6.1(3) . .
C15 C15 N11 C12 0.1(4) 4_655 .
C15 C15 N11 C81 173.9(3) 4_655 .
C83 C81 N11 C12 60.3(3) . .
C82 C81 N11 C12 -176.5(2) . .
C83 C81 N11 C15 -112.5(3) . .
C82 C81 N11 C15 10.7(4) . .
