#------------------------------------------------------------------------------
#$Date: 2020-08-12 08:02:22 +0300 (Wed, 12 Aug 2020) $
#$Revision: 255259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/88/1558831.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1558831
loop_
_publ_author_name
'Detert, Heiner'
'Schollmeyer, Dieter'
_publ_section_title
;
 rac-12-Selena-13,14-diazatricyclo[9.3.0.0^2,4^]tetradeca-11,13-diene
;
_journal_coeditor_code           HB4354
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x201081
_journal_paper_doi               10.1107/S2414314620010810
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C11 H16 N2 Se'
_chemical_formula_moiety         'C11 H16 N2 Se'
_chemical_formula_sum            'C11 H16 N2 Se'
_chemical_formula_weight         255.22
_chemical_name_systematic
;
rac-12-Selena-13,14-diazatricyclo[9.3.0.0^2,4^]tetradeca-11,13-diene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.104(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0239(6)
_cell_length_b                   7.1317(3)
_cell_length_c                   12.6836(7)
_cell_measurement_reflns_used    11220
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.86
_cell_volume                     1067.27(9)
_computing_cell_refinement
;
X-Area Recipe (Stoe & Cie, 2019)
;
_computing_data_collection
;
X-Area WinXpose (Stoe & Cie, 2019)
;
_computing_data_reduction
;
X-Area Integrate (Stoe & Cie, 2019)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR-2004 (Burla et al.,  2005)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5541
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.024
_diffrn_reflns_theta_min         3.274
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    3.480
_exptl_absorpt_correction_T_max  0.7042
_exptl_absorpt_correction_T_min  0.2277
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.898
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0573P)²+1.4452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                2364
_reflns_number_total             2570
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4354sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1558831
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.251
_shelx_estimated_absorpt_t_max   0.722
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.01806(2) 0.53889(3) 0.19801(2) 0.01717(11) Uani d 1 . .
N N2 0.08518(19) 0.7735(3) 0.24245(18) 0.0195(4) Uani d 1 . .
N N3 0.16960(17) 0.7494(3) 0.31890(17) 0.0167(4) Uani d 1 . .
C C4 0.1961(2) 0.5686(3) 0.35355(19) 0.0131(4) Uani d 1 . .
C C5 0.2954(2) 0.5360(3) 0.4406(2) 0.0144(4) Uani d 1 . .
H H5 0.337544 0.417298 0.433140 0.017 Uiso calc 1 . .
C C6 0.2942(2) 0.5921(3) 0.55614(18) 0.0149(4) Uani d 1 . .
H H6 0.225279 0.662016 0.567102 0.018 Uiso calc 1 . .
C C7 0.3456(2) 0.4626(3) 0.6468(2) 0.0177(5) Uani d 1 . .
H H7A 0.375621 0.539411 0.711012 0.021 Uiso calc 1 . .
H H7B 0.410401 0.396039 0.626172 0.021 Uiso calc 1 . .
C C8 0.2633(2) 0.3164(4) 0.67731(19) 0.0178(5) Uani d 1 . .
H H8A 0.203057 0.382731 0.705866 0.021 Uiso calc 1 . .
H H8B 0.305015 0.236704 0.735703 0.021 Uiso calc 1 . .
C C9 0.2071(2) 0.1890(3) 0.58429(19) 0.0173(5) Uani d 1 . .
H H9A 0.260533 0.170100 0.534790 0.021 Uiso calc 1 . .
H H9B 0.192121 0.064881 0.613659 0.021 Uiso calc 1 . .
C C10 0.09558(19) 0.2684(3) 0.52058(18) 0.0154(4) Uani d 1 . .
H H10A 0.035621 0.252598 0.563508 0.018 Uiso calc 1 . .
H H10B 0.105037 0.404482 0.509630 0.018 Uiso calc 1 . .
C C11 0.0569(2) 0.1748(3) 0.41110(19) 0.0170(5) Uani d 1 . .
H H11A -0.022326 0.212211 0.382070 0.020 Uiso calc 1 . .
H H11B 0.058059 0.037076 0.421121 0.020 Uiso calc 1 . .
C C12 0.1307(2) 0.2250(3) 0.32802(19) 0.0147(4) Uani d 1 . .
H H12A 0.210110 0.187617 0.356552 0.018 Uiso calc 1 . .
H H12B 0.103796 0.153162 0.261179 0.018 Uiso calc 1 . .
C C13 0.1270(2) 0.4310(3) 0.30231(19) 0.0143(4) Uani d 1 . .
C C14 0.3690(2) 0.6950(4) 0.4927(2) 0.0195(5) Uani d 1 . .
H H14A 0.451685 0.673076 0.511923 0.023 Uiso calc 1 . .
H H14B 0.346890 0.824166 0.468684 0.023 Uiso calc 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'
Se Se -0.0929 2.2259 '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
C13 Se1 N2 . . 87.26(10) ?
N3 N2 Se1 . . 109.79(16) ?
N2 N3 C4 . . 118.1(2) ?
C13 C4 N3 . . 115.9(2) ?
C13 C4 C5 . . 124.8(2) ?
N3 C4 C5 . . 119.3(2) ?
C4 C5 C14 . . 121.9(2) ?
C4 C5 C6 . . 121.4(2) ?
C14 C5 C6 . . 59.64(15) ?
C4 C5 H5 . . 114.4 ?
C14 C5 H5 . . 114.4 ?
C6 C5 H5 . . 114.4 ?
C14 C6 C7 . . 120.4(2) ?
C14 C6 C5 . . 59.79(15) ?
C7 C6 C5 . . 119.6(2) ?
C14 C6 H6 . . 115.3 ?
C7 C6 H6 . . 115.3 ?
C5 C6 H6 . . 115.3 ?
C6 C7 C8 . . 114.7(2) ?
C6 C7 H7A . . 108.6 ?
C8 C7 H7A . . 108.6 ?
C6 C7 H7B . . 108.6 ?
C8 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
C7 C8 C9 . . 114.6(2) ?
C7 C8 H8A . . 108.6 ?
C9 C8 H8A . . 108.6 ?
C7 C8 H8B . . 108.6 ?
C9 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
C10 C9 C8 . . 113.3(2) ?
C10 C9 H9A . . 108.9 ?
C8 C9 H9A . . 108.9 ?
C10 C9 H9B . . 108.9 ?
C8 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C11 C10 C9 . . 113.5(2) ?
C11 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
C11 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C10 C11 C12 . . 113.84(19) ?
C10 C11 H11A . . 108.8 ?
C12 C11 H11A . . 108.8 ?
C10 C11 H11B . . 108.8 ?
C12 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C11 . . 112.17(19) ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12B . . 109.2 ?
C11 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C4 C13 C12 . . 127.5(2) ?
C4 C13 Se1 . . 108.95(17) ?
C12 C13 Se1 . . 123.47(18) ?
C6 C14 C5 . . 60.58(15) ?
C6 C14 H14A . . 117.7 ?
C5 C14 H14A . . 117.7 ?
C6 C14 H14B . . 117.7 ?
C5 C14 H14B . . 117.7 ?
H14A C14 H14B . . 114.8 ?
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
Se1 C13 . 1.841(2) ?
Se1 N2 . 1.896(2) ?
N2 N3 . 1.273(3) ?
N3 C4 . 1.379(3) ?
C4 C13 . 1.367(3) ?
C4 C5 . 1.480(3) ?
C5 C14 . 1.510(3) ?
C5 C6 . 1.522(3) ?
C5 H5 . 1.0000 ?
C6 C14 . 1.507(3) ?
C6 C7 . 1.511(3) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.538(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.538(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.535(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.530(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.544(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.504(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 Se1 N2 N3 . . . . 0.23(17) ?
Se1 N2 N3 C4 . . . . 0.2(3) ?
N2 N3 C4 C13 . . . . -0.8(3) ?
N2 N3 C4 C5 . . . . 178.6(2) ?
C13 C4 C5 C14 . . . . 179.2(2) ?
N3 C4 C5 C14 . . . . -0.1(3) ?
C13 C4 C5 C6 . . . . -109.3(3) ?
N3 C4 C5 C6 . . . . 71.3(3) ?
C4 C5 C6 C14 . . . . -111.1(2) ?
C4 C5 C6 C7 . . . . 138.9(2) ?
C14 C5 C6 C7 . . . . -110.0(2) ?
C14 C6 C7 C8 . . . . -159.1(2) ?
C5 C6 C7 C8 . . . . -88.8(3) ?
C6 C7 C8 C9 . . . . 56.9(3) ?
C7 C8 C9 C10 . . . . -89.4(3) ?
C8 C9 C10 C11 . . . . 163.53(19) ?
C9 C10 C11 C12 . . . . -70.9(3) ?
C10 C11 C12 C13 . . . . -62.5(3) ?
N3 C4 C13 C12 . . . . -175.5(2) ?
C5 C4 C13 C12 . . . . 5.1(4) ?
N3 C4 C13 Se1 . . . . 0.9(3) ?
C5 C4 C13 Se1 . . . . -178.47(18) ?
C11 C12 C13 C4 . . . . 89.1(3) ?
C11 C12 C13 Se1 . . . . -86.8(2) ?
N2 Se1 C13 C4 . . . . -0.62(17) ?
N2 Se1 C13 C12 . . . . 175.9(2) ?
C7 C6 C14 C5 . . . . 108.7(2) ?
C4 C5 C14 C6 . . . . 110.3(2) ?

_cod_database_fobs_code 1558831
