#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:09:50 +0300 (Fri, 05 May 2023) $
#$Revision: 283036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/10/7131087.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_7131087
loop_
_publ_author_name
'Toda, Yasunori'
'Kooguchi, Airi'
'Sukegawa, Kimiya'
'Kikuchi, Ayaka'
'Suga, Hiroyuki'
_publ_section_title
;
 Ring-fused hexahydro-1,2,4,5-tetrazines: synthesis, structure, and
 mechanistic studies on isolable rotational isomers.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              700
_journal_page_last               703
_journal_paper_doi               10.1039/d2cc06170h
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_weight         348.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-10-31 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.876(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.28(2)
_cell_length_b                   8.194(8)
_cell_length_c                   22.20(2)
_cell_measurement_reflns_used    148
_cell_measurement_temperature    88.(2)
_cell_measurement_theta_max      21.9964
_cell_measurement_theta_min      2.0698
_cell_volume                     3483(6)
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      88.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9409
_diffrn_reflns_theta_full        27.14
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0753P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                1854
_reflns_number_total             3758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc06170h2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7131087--7131090.cif.'
_cod_original_cell_volume        3483.(6)
_cod_database_code               7131087
loop_
_space_group_symop_operation_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_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.08237(11) 0.4281(3) 1.03674(9) 0.0792(7) Uani d . 1 . .
O O2 0.19324(10) -0.0935(2) 1.00514(9) 0.0736(6) Uani d . 1 . .
N N1 0.15205(10) 0.1830(3) 0.87374(10) 0.0559(6) Uani d . 1 . .
N N2 0.15468(11) 0.1228(3) 0.93633(10) 0.0599(6) Uani d . 1 . .
N N3 0.09165(11) 0.4128(2) 0.88292(10) 0.0543(6) Uani d . 1 . .
N N4 0.09884(12) 0.3518(3) 0.94657(11) 0.0603(6) Uani d . 1 . .
C C1 0.15808(17) 0.5543(4) 0.70026(15) 0.0683(8) Uani d . 1 . .
H H1A 0.1592 0.5976 0.6611 0.082 Uiso calc R 1 . .
C C2 0.10586(16) 0.4505(4) 0.69484(13) 0.0670(8) Uani d . 1 . .
H H2 0.0707 0.4216 0.6519 0.08 Uiso calc R 1 . .
C C3 0.10393(14) 0.3872(3) 0.75173(13) 0.0612(7) Uani d . 1 . .
H H3 0.0673 0.3154 0.7478 0.073 Uiso calc R 1 . .
C C4 0.15538(13) 0.4282(3) 0.81460(11) 0.0484(6) Uani d . 1 . .
C C5 0.15445(13) 0.3604(3) 0.87687(12) 0.0523(7) Uani d . 1 . .
H H5 0.1971 0.3968 0.917 0.063 Uiso calc R 1 . .
C C6 0.09893(13) 0.1780(3) 0.95200(13) 0.0569(7) Uani d . 1 . .
H H6 0.1124 0.1507 1.0 0.068 Uiso calc R 1 . .
C C7 0.02845(14) 0.1020(3) 0.91065(13) 0.0549(7) Uani d . 1 . .
C C8 -0.02342(16) 0.1254(4) 0.93122(17) 0.0765(9) Uani d . 1 . .
H H8 -0.0136 0.1874 0.9705 0.092 Uiso calc R 1 . .
C C9 -0.08862(19) 0.0610(4) 0.8961(2) 0.0893(10) Uani d . 1 . .
H H9 -0.1239 0.0806 0.9106 0.107 Uiso calc R 1 . .
C C10 -0.10335(18) -0.0305(4) 0.8408(2) 0.0877(10) Uani d . 1 . .
H H10 -0.1485 -0.0769 0.8169 0.105 Uiso calc R 1 . .
C C11 0.09240(19) 0.5917(3) 0.89298(17) 0.0796(9) Uani d . 1 . .
H H11A 0.0603 0.6467 0.8511 0.095 Uiso calc R 1 . .
H H11B 0.14 0.6359 0.907 0.095 Uiso calc R 1 . .
C C12 0.06882(16) 0.6176(4) 0.94683(14) 0.0670(8) Uani d . 1 . .
H H12A 0.0951 0.708 0.9769 0.08 Uiso calc R 1 . .
H H12B 0.0183 0.6431 0.9272 0.08 Uiso calc R 1 . .
C C13 0.08378(13) 0.4606(4) 0.98359(14) 0.0601(7) Uani d . 1 . .
C C14 0.21772(15) 0.1117(4) 0.87636(16) 0.0755(9) Uani d . 1 . .
H H14A 0.2132 0.0909 0.8307 0.091 Uiso calc R 1 . .
H H14B 0.2578 0.1856 0.9 0.091 Uiso calc R 1 . .
C C15 0.2266(2) -0.0424(4) 0.91350(19) 0.0720(9) Uani d . 1 . .
C C16 0.19148(13) -0.0130(3) 0.95800(13) 0.0533(6) Uani d . 1 . .
C C17 -0.0516(2) -0.0560(4) 0.81921(18) 0.0909(10) Uani d . 1 . .
H H17 -0.0613 -0.1196 0.7804 0.109 Uiso calc R 1 . .
C C18 0.01349(17) 0.0110(4) 0.85435(17) 0.0763(9) Uani d . 1 . .
H H18 0.0486 -0.0059 0.8394 0.092 Uiso calc R 1 . .
C C19 0.20741(13) 0.5325(3) 0.81921(13) 0.0584(7) Uani d . 1 . .
H H23 0.2429 0.5613 0.862 0.07 Uiso calc R 1 . .
C C20 0.20908(15) 0.5966(4) 0.76227(14) 0.0693(8) Uani d . 1 . .
H H21 0.2453 0.6696 0.766 0.083 Uiso calc R 1 . .
H H22 0.2685(16) -0.082(3) 0.9361(14) 0.074(9) Uiso d . 1 . .
H H24 0.197(2) -0.122(5) 0.8772(19) 0.129(15) Uiso d . 1 . .
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C5 . . 107.94(19) ?
N2 N1 C14 . . 100.66(19) ?
C5 N1 C14 . . 112.1(2) ?
C16 N2 C6 . . 126.3(2) ?
C16 N2 N1 . . 113.8(2) ?
C6 N2 N1 . . 115.5(2) ?
N4 N3 C5 . . 106.12(19) ?
N4 N3 C11 . . 101.85(19) ?
C5 N3 C11 . . 110.7(2) ?
C13 N4 C6 . . 127.0(2) ?
C13 N4 N3 . . 114.7(2) ?
C6 N4 N3 . . 115.04(19) ?
C2 C1 C20 . . 120.2(3) ?
C2 C1 H1A . . 119.9 ?
C20 C1 H1A . . 119.9 ?
C1 C2 C3 . . 120.1(3) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.2(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C19 C4 C3 . . 119.0(2) ?
C19 C4 C5 . . 119.9(2) ?
C3 C4 C5 . . 121.1(2) ?
N1 C5 N3 . . 106.41(19) ?
N1 C5 C4 . . 109.9(2) ?
N3 C5 C4 . . 110.9(2) ?
N1 C5 H5 . . 109.9 ?
N3 C5 H5 . . 109.9 ?
C4 C5 H5 . . 109.9 ?
N4 C6 N2 . . 105.2(2) ?
N4 C6 C7 . . 113.3(2) ?
N2 C6 C7 . . 115.2(2) ?
N4 C6 H6 . . 107.6 ?
N2 C6 H6 . . 107.6 ?
C7 C6 H6 . . 107.6 ?
C18 C7 C8 . . 118.5(3) ?
C18 C7 C6 . . 123.6(2) ?
C8 C7 C6 . . 117.9(3) ?
C9 C8 C7 . . 121.1(3) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C10 C9 C8 . . 120.5(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C17 . . 119.3(3) ?
C9 C10 H10 . . 120.4 ?
C17 C10 H10 . . 120.4 ?
N3 C11 C12 . . 105.9(2) ?
N3 C11 H11A . . 110.5 ?
C12 C11 H11A . . 110.5 ?
N3 C11 H11B . . 110.5 ?
C12 C11 H11B . . 110.5 ?
H11A C11 H11B . . 108.7 ?
C13 C12 C11 . . 104.5(2) ?
C13 C12 H12A . . 110.9 ?
C11 C12 H12A . . 110.9 ?
C13 C12 H12B . . 110.9 ?
C11 C12 H12B . . 110.9 ?
H12A C12 H12B . . 108.9 ?
O1 C13 N4 . . 124.0(3) ?
O1 C13 C12 . . 129.1(2) ?
N4 C13 C12 . . 106.9(2) ?
C15 C14 N1 . . 104.3(2) ?
C15 C14 H14A . . 110.9 ?
N1 C14 H14A . . 110.9 ?
C15 C14 H14B . . 110.9 ?
N1 C14 H14B . . 110.9 ?
H14A C14 H14B . . 108.9 ?
C14 C15 C16 . . 104.6(3) ?
C14 C15 H22 . . 119.1(19) ?
C16 C15 H22 . . 111.1(18) ?
C14 C15 H24 . . 103.(2) ?
C16 C15 H24 . . 108.(2) ?
H22 C15 H24 . . 111.(3) ?
O2 C16 N2 . . 123.8(2) ?
O2 C16 C15 . . 129.8(3) ?
N2 C16 C15 . . 106.4(2) ?
C18 C17 C10 . . 119.8(3) ?
C18 C17 H17 . . 120.1 ?
C10 C17 H17 . . 120.1 ?
C7 C18 C17 . . 120.8(3) ?
C7 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C4 C19 C20 . . 120.8(2) ?
C4 C19 H23 . . 119.6 ?
C20 C19 H23 . . 119.6 ?
C1 C20 C19 . . 119.7(3) ?
C1 C20 H21 . . 120.2 ?
C19 C20 H21 . . 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.223(3) ?
O2 C16 . 1.224(3) ?
N1 N2 . 1.452(3) ?
N1 C5 . 1.455(4) ?
N1 C14 . 1.492(3) ?
N2 C16 . 1.324(3) ?
N2 C6 . 1.447(3) ?
N3 N4 . 1.442(3) ?
N3 C5 . 1.464(3) ?
N3 C11 . 1.482(4) ?
N4 C13 . 1.342(3) ?
N4 C6 . 1.429(4) ?
C1 C2 . 1.362(4) ?
C1 C20 . 1.374(4) ?
C1 H1A . 0.95 ?
C2 C3 . 1.383(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.388(4) ?
C3 H3 . 0.95 ?
C4 C19 . 1.367(3) ?
C4 C5 . 1.498(3) ?
C5 H5 . 1.0 ?
C6 C7 . 1.509(4) ?
C6 H6 . 1.0 ?
C7 C18 . 1.368(4) ?
C7 C8 . 1.380(4) ?
C8 C9 . 1.366(5) ?
C8 H8 . 0.95 ?
C9 C10 . 1.354(5) ?
C9 H9 . 0.95 ?
C10 C17 . 1.395(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.500(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.482(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C14 C15 . 1.474(4) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.495(4) ?
C15 H22 . 0.87(3) ?
C15 H24 . 1.02(4) ?
C17 C18 . 1.373(5) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 C20 . 1.384(3) ?
C19 H23 . 0.95 ?
C20 H21 . 0.95 ?
