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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031936.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_4031936
loop_
_publ_author_name
'Wrobel, Agnes Johanna'
'Lucchesi, Ralph'
'Wibbeling, Birgit'
'Daniliuc, Constantin-Gabriel'
'Fröhlich, Roland'
'Würthwein, Ernst-Ulrich'
_publ_section_title
;
 1,3,5-Triazapentadienes by Nucleophilic Addition to 1,3- and
 1,4-Dinitriles-Sterically Constrained Examples by Incorporation into
 Cyclic Peripheries: Synthesis, Aggregation, and Photophysical Properties.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2849
_journal_page_last               2863
_journal_paper_doi               10.1021/acs.joc.6b00126
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C19 H16 N4 O'
_chemical_formula_weight         316.36
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.9750(5)
_cell_length_b                   7.9493(2)
_cell_length_c                   19.2418(6)
_cell_measurement_reflns_used    3759
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      4.08
_cell_volume                     3246.84(15)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.078
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15235
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         4.08
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²+5.3955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                2299
_reflns_number_total             3250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00126_si_005.cif
_cod_data_source_block           wue5797
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4031936
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
O1 O 0.09060(11) 0.6931(3) 0.32061(12) 0.0616(6) Uani 1 1 d .
H01 H 0.0982(16) 0.684(5) 0.271(2) 0.093(12) Uiso 1 1 d .
H02 H 0.0516(18) 0.737(5) 0.3096(19) 0.087(13) Uiso 1 1 d .
N1 N 0.07592(9) 0.4541(3) 0.56162(11) 0.0364(5) Uani 1 1 d .
N2 N 0.06369(11) 0.5507(3) 0.44802(12) 0.0412(5) Uani 1 1 d .
H2A H 0.0183(15) 0.553(4) 0.4421(16) 0.060(9) Uiso 1 1 d .
H2B H 0.0796(12) 0.583(3) 0.4120(15) 0.044(8) Uiso 1 1 d .
N3 N 0.10051(9) 0.3157(3) 0.67353(11) 0.0381(5) Uani 1 1 d .
N4 N 0.01975(11) 0.1242(3) 0.66829(13) 0.0515(6) Uani 1 1 d .
C1 C 0.10821(10) 0.4382(3) 0.63289(13) 0.0352(5) Uani 1 1 d .
C2 C 0.10131(11) 0.5083(3) 0.51179(13) 0.0346(5) Uani 1 1 d .
C3 C 0.17024(11) 0.5125(3) 0.51861(13) 0.0377(6) Uani 1 1 d .
C4 C 0.19208(13) 0.4481(3) 0.46199(15) 0.0470(7) Uani 1 1 d .
H4 H 0.1631 0.4047 0.4211 0.056 Uiso 1 1 calc R
C5 C 0.25536(14) 0.4473(4) 0.46523(17) 0.0563(8) Uani 1 1 d .
H5 H 0.2698 0.4009 0.4274 0.068 Uiso 1 1 calc R
C6 C 0.29750(13) 0.5153(4) 0.52456(18) 0.0581(8) Uani 1 1 d .
H6 H 0.3407 0.5165 0.5267 0.070 Uiso 1 1 calc R
C7 C 0.27694(12) 0.5811(4) 0.58034(16) 0.0503(7) Uani 1 1 d .
H7 H 0.3064 0.6277 0.6200 0.060 Uiso 1 1 calc R
C8 C 0.21297(11) 0.5807(3) 0.57963(14) 0.0397(6) Uani 1 1 d .
C9 C 0.19317(11) 0.6557(3) 0.64077(14) 0.0412(6) Uani 1 1 d .
C10 C 0.22535(13) 0.7965(4) 0.67616(16) 0.0526(7) Uani 1 1 d .
H10 H 0.2581 0.8441 0.6596 0.063 Uiso 1 1 calc R
C11 C 0.20987(16) 0.8662(4) 0.73458(18) 0.0646(9) Uani 1 1 d .
H11 H 0.2316 0.9617 0.7569 0.078 Uiso 1 1 calc R
C12 C 0.16261(16) 0.7972(4) 0.76070(17) 0.0646(9) Uani 1 1 d .
H12 H 0.1523 0.8454 0.8008 0.078 Uiso 1 1 calc R
C13 C 0.13052(14) 0.6568(4) 0.72780(15) 0.0518(7) Uani 1 1 d .
H13 H 0.0987 0.6087 0.7460 0.062 Uiso 1 1 calc R
C14 C 0.14507(11) 0.5869(3) 0.66818(13) 0.0389(6) Uani 1 1 d .
C15 C 0.06757(11) 0.1693(3) 0.64199(13) 0.0375(6) Uani 1 1 d .
C16 C -0.00909(15) -0.0224(4) 0.64475(19) 0.0648(9) Uani 1 1 d .
H16 H -0.0432 -0.0558 0.6627 0.078 Uiso 1 1 calc R
C17 C 0.00829(15) -0.1253(4) 0.59633(18) 0.0625(9) Uani 1 1 d .
H17 H -0.0129 -0.2271 0.5817 0.075 Uiso 1 1 calc R
C18 C 0.05771(15) -0.0752(4) 0.56971(17) 0.0587(8) Uani 1 1 d .
H18 H 0.0708 -0.1426 0.5361 0.070 Uiso 1 1 calc R
C19 C 0.08767(13) 0.0727(4) 0.59236(15) 0.0480(7) Uani 1 1 d .
H19 H 0.1215 0.1086 0.5745 0.058 Uiso 1 1 calc R
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
H01 O1 H02 101(3)
C2 N1 C1 123.7(2)
C2 N2 H2A 119.0(18)
C2 N2 H2B 121.0(17)
H2A N2 H2B 120(2)
C1 N3 C15 119.5(2)
C15 N4 C16 117.1(3)
N3 C1 N1 124.0(2)
N3 C1 C14 117.6(2)
N1 C1 C14 117.3(2)
N1 C2 N2 118.7(2)
N1 C2 C3 124.3(2)
N2 C2 C3 116.8(2)
C4 C3 C8 120.1(2)
C4 C3 C2 118.1(2)
C8 C3 C2 121.8(2)
C5 C4 C3 120.9(3)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 119.3(3)
C4 C5 H5 120.3
C6 C5 H5 120.3
C7 C6 C5 120.7(3)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 121.6(3)
C6 C7 H7 119.2
C8 C7 H7 119.2
C7 C8 C3 117.4(2)
C7 C8 C9 119.4(2)
C3 C8 C9 123.2(2)
C10 C9 C14 117.5(3)
C10 C9 C8 119.5(2)
C14 C9 C8 123.0(2)
C11 C10 C9 121.3(3)
C11 C10 H10 119.4
C9 C10 H10 119.4
C10 C11 C12 120.5(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C13 119.8(3)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C14 120.2(3)
C12 C13 H13 119.9
C14 C13 H13 119.9
C13 C14 C9 120.7(2)
C13 C14 C1 118.7(2)
C9 C14 C1 120.6(2)
N4 C15 C19 122.6(2)
N4 C15 N3 115.1(2)
C19 C15 N3 122.1(2)
N4 C16 C17 123.8(3)
N4 C16 H16 118.1
C17 C16 H16 118.1
C16 C17 C18 117.9(3)
C16 C17 H17 121.0
C18 C17 H17 121.0
C19 C18 C17 119.6(3)
C19 C18 H18 120.2
C17 C18 H18 120.2
C18 C19 C15 119.0(3)
C18 C19 H19 120.5
C15 C19 H19 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H01 1.01(4)
O1 H02 0.90(4)
N1 C2 1.301(3)
N1 C1 1.377(3)
N2 C2 1.333(3)
N2 H2A 0.97(3)
N2 H2B 0.89(3)
N3 C1 1.288(3)
N3 C15 1.421(3)
N4 C15 1.328(3)
N4 C16 1.348(4)
C1 C14 1.493(3)
C2 C3 1.487(3)
C3 C4 1.397(4)
C3 C8 1.408(3)
C4 C5 1.376(4)
C4 H4 0.9400
C5 C6 1.381(4)
C5 H5 0.9400
C6 C7 1.372(4)
C6 H6 0.9400
C7 C8 1.402(3)
C7 H7 0.9400
C8 C9 1.481(4)
C9 C10 1.403(4)
C9 C14 1.408(4)
C10 C11 1.373(4)
C10 H10 0.9400
C11 C12 1.379(5)
C11 H11 0.9400
C12 C13 1.383(4)
C12 H12 0.9400
C13 C14 1.385(4)
C13 H13 0.9400
C15 C19 1.384(4)
C16 C17 1.366(4)
C16 H16 0.9400
C17 C18 1.374(4)
C17 H17 0.9400
C18 C19 1.363(4)
C18 H18 0.9400
C19 H19 0.9400
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
N2 H2B O1 0.89(3) 2.03(3) 2.897(3) 163(2) .
O1 H01 N3 1.01(4) 1.89(4) 2.895(3) 171(3) 6_565
O1 H02 N4 0.90(4) 2.05(4) 2.882(3) 153(3) 5_566
N2 H2A N1 0.97(3) 2.05(3) 3.026(3) 175(3) 5_566
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
C15 N3 C1 N1 13.9(3)
C15 N3 C1 C14 -177.9(2)
C2 N1 C1 N3 -141.1(3)
C2 N1 C1 C14 50.7(3)
C1 N1 C2 N2 -166.7(2)
C1 N1 C2 C3 18.9(4)
N1 C2 C3 C4 132.0(3)
N2 C2 C3 C4 -42.5(3)
N1 C2 C3 C8 -48.7(4)
N2 C2 C3 C8 136.9(2)
C8 C3 C4 C5 1.1(4)
C2 C3 C4 C5 -179.5(2)
C3 C4 C5 C6 -1.7(4)
C4 C5 C6 C7 0.9(5)
C5 C6 C7 C8 0.6(5)
C6 C7 C8 C3 -1.1(4)
C6 C7 C8 C9 -179.1(3)
C4 C3 C8 C7 0.3(4)
C2 C3 C8 C7 -179.0(2)
C4 C3 C8 C9 178.2(2)
C2 C3 C8 C9 -1.2(4)
C7 C8 C9 C10 34.3(4)
C3 C8 C9 C10 -143.5(3)
C7 C8 C9 C14 -142.3(3)
C3 C8 C9 C14 39.9(4)
C14 C9 C10 C11 -1.0(4)
C8 C9 C10 C11 -177.7(3)
C9 C10 C11 C12 1.0(5)
C10 C11 C12 C13 -0.1(5)
C11 C12 C13 C14 -0.9(5)
C12 C13 C14 C9 0.9(4)
C12 C13 C14 C1 -178.4(3)
C10 C9 C14 C13 0.0(4)
C8 C9 C14 C13 176.6(2)
C10 C9 C14 C1 179.3(2)
C8 C9 C14 C1 -4.1(4)
N3 C1 C14 C13 -48.3(3)
N1 C1 C14 C13 120.7(3)
N3 C1 C14 C9 132.4(2)
N1 C1 C14 C9 -58.6(3)
C16 N4 C15 C19 0.3(4)
C16 N4 C15 N3 -174.0(2)
C1 N3 C15 N4 -126.4(3)
C1 N3 C15 C19 59.3(3)
C15 N4 C16 C17 0.3(5)
N4 C16 C17 C18 -0.6(5)
C16 C17 C18 C19 0.4(5)
C17 C18 C19 C15 0.1(4)
N4 C15 C19 C18 -0.5(4)
N3 C15 C19 C18 173.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094654
