#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/84/1558492.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_1558492
loop_
_publ_author_name
'Szukalski, Adam'
'Haupa, Karolina A.'
'Janczak, Jan'
'Przybył, Bartosz'
'Sznitko, Lech'
'Myśliwiec, Jarosław'
_publ_section_title
;
 Lasing Properties Activation by Constitutional Isomerism of an
 Electron-Accepting Group
;
_journal_issue                   25
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              13845
_journal_page_last               13857
_journal_paper_doi               10.1021/acs.jpcc.0c01054
_journal_volume                  124
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 N4'
_chemical_formula_sum            'C19 H14 N4'
_chemical_formula_weight         298.34
_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_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.092(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.9461(11)
_cell_length_b                   8.4289(3)
_cell_length_c                   13.7881(6)
_cell_measurement_reflns_used    1762
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.53
_cell_volume                     3135.8(2)
_computing_cell_refinement
;
CrysAlis Red 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_collection
;
CrysAlis CCD 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
CrysAlis Red 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
;
_computing_molecular_graphics
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.6249
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'KUMA KM-4 with CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21248
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        28.750
_diffrn_reflns_theta_max         29.628
_diffrn_reflns_theta_min         2.532
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.023
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0373
_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)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2350
_reflns_number_total             4182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp0c01054_si_003.cif
_cod_data_source_block           Py-oCNCN
_cod_depositor_comments
'Adding full bibliography for 1558491--1558492.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1558492
_shelx_shelxl_version_number     2014/7
_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   0.980
_shelx_estimated_absorpt_t_max   0.984
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55827(4) 0.84853(12) 0.10719(9) 0.0441(3) Uani 1 1 d . . . . .
C2 C 0.59451(4) 0.95445(13) 0.09526(10) 0.0549(3) Uani 1 1 d . . . . .
H2 H 0.5982 0.9774 0.0316 0.066 Uiso 1 1 calc R U . . .
C3 C 0.62520(5) 1.02554(14) 0.17985(11) 0.0627(4) Uani 1 1 d . . . . .
H3 H 0.6494 1.0968 0.1722 0.075 Uiso 1 1 calc R U . . .
C4 C 0.62050(5) 0.99259(14) 0.27429(11) 0.0618(3) Uani 1 1 d . . . . .
H4 H 0.6410 1.0421 0.3302 0.074 Uiso 1 1 calc R U . . .
C5 C 0.58534(4) 0.88590(15) 0.28543(9) 0.0571(3) Uani 1 1 d . . . . .
H5 H 0.5823 0.8622 0.3494 0.069 Uiso 1 1 calc R U . . .
C6 C 0.55447(4) 0.81330(13) 0.20317(9) 0.0509(3) Uani 1 1 d . . . . .
H6 H 0.5310 0.7404 0.2120 0.061 Uiso 1 1 calc R U . . .
N1 N 0.52631(3) 0.77729(11) 0.02357(7) 0.0518(3) Uani 1 1 d . . . . .
N2 N 0.48457(3) 0.70320(11) 0.03233(7) 0.0461(2) Uani 1 1 d . . . . .
C7 C 0.45815(4) 0.66194(12) -0.05648(8) 0.0414(3) Uani 1 1 d . . . . .
C8 C 0.48287(4) 0.70377(14) -0.13790(9) 0.0533(3) Uani 1 1 d . . . . .
H8A H 0.4610 0.7651 -0.1908 0.080 Uiso 1 1 calc R U . . .
H8B H 0.4935 0.6094 -0.1668 0.080 Uiso 1 1 calc R U . . .
C9 C 0.52704(4) 0.80225(15) -0.08107(8) 0.0531(3) Uani 1 1 d . . . . .
H9A H 0.5577 0.7641 -0.0933 0.080 Uiso 1 1 calc R U . . .
H9B H 0.5228 0.9134 -0.0994 0.080 Uiso 1 1 calc R U . . .
C10 C 0.41189(4) 0.58489(12) -0.06402(8) 0.0423(3) Uani 1 1 d . . . . .
H10 H 0.4043 0.5645 -0.0034 0.051 Uiso 1 1 calc R U . . .
C11 C 0.37755(4) 0.53752(12) -0.14754(8) 0.0416(3) Uani 1 1 d . . . . .
C12 C 0.33033(4) 0.46098(12) -0.14464(8) 0.0420(3) Uani 1 1 d . . . . .
C13 C 0.30133(4) 0.51569(12) -0.08227(8) 0.0442(3) Uani 1 1 d . . . . .
C14 C 0.25831(4) 0.43608(15) -0.07812(9) 0.0570(3) Uani 1 1 d . . . . .
H14 H 0.2395 0.4731 -0.0363 0.068 Uiso 1 1 calc R U . . .
C15 C 0.24351(5) 0.30312(16) -0.13557(11) 0.0654(4) Uani 1 1 d . . . . .
H15 H 0.2151 0.2485 -0.1317 0.079 Uiso 1 1 calc R U . . .
C16 C 0.27099(5) 0.25135(16) -0.19883(11) 0.0689(4) Uani 1 1 d . . . . .
H16 H 0.2608 0.1621 -0.2385 0.083 Uiso 1 1 calc R U . . .
C17 C 0.31326(4) 0.33003(14) -0.20411(9) 0.0565(3) Uani 1 1 d . . . . .
H17 H 0.3308 0.2945 -0.2487 0.068 Uiso 1 1 calc R U . . .
C18 C 0.38487(4) 0.55431(13) -0.24649(10) 0.0519(3) Uani 1 1 d . . . . .
N3 N 0.38800(4) 0.56578(14) -0.32708(9) 0.0763(4) Uani 1 1 d . . . . .
C19 C 0.31286(4) 0.66235(16) -0.02794(9) 0.0556(3) Uani 1 1 d . . . . .
N4 N 0.31989(4) 0.78177(15) 0.01222(10) 0.0831(4) Uani 1 1 d . . . . .
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'
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
C6 C1 C2 119.27(11) . . ?
C6 C1 N1 120.28(10) . . ?
C2 C1 N1 120.45(10) . . ?
C3 C2 C1 119.10(11) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.24(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.24(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.88(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.25(11) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N2 N1 C1 120.29(9) . . ?
N2 N1 C9 112.77(9) . . ?
C1 N1 C9 125.59(9) . . ?
C7 N2 N1 109.25(9) . . ?
N2 C7 C10 118.14(9) . . ?
N2 C7 C8 112.39(9) . . ?
C10 C7 C8 129.47(10) . . ?
C7 C8 C9 102.22(9) . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C9 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
N1 C9 C8 102.20(9) . . ?
N1 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
N1 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C11 C10 C7 128.68(10) . . ?
C11 C10 H10 115.7 . . ?
C7 C10 H10 115.7 . . ?
C10 C11 C18 122.27(10) . . ?
C10 C11 C12 123.08(10) . . ?
C18 C11 C12 114.64(9) . . ?
C17 C12 C13 117.39(10) . . ?
C17 C12 C11 120.28(10) . . ?
C13 C12 C11 122.32(9) . . ?
C14 C13 C12 120.64(10) . . ?
C14 C13 C19 118.17(10) . . ?
C12 C13 C19 120.98(10) . . ?
C15 C14 C13 120.25(11) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.42(12) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.72(12) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 121.50(12) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
N3 C18 C11 176.26(13) . . ?
N4 C19 C13 176.61(14) . . ?
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
C1 C6 1.3871(15) . ?
C1 C2 1.3915(15) . ?
C1 N1 1.3968(14) . ?
C2 C3 1.3908(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.3708(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3700(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.3767(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 N2 1.3561(12) . ?
N1 C9 1.4634(14) . ?
N2 C7 1.3017(13) . ?
C7 C10 1.4262(14) . ?
C7 C8 1.5053(14) . ?
C8 C9 1.5241(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.3531(14) . ?
C10 H10 0.9300 . ?
C11 C18 1.4382(16) . ?
C11 C12 1.4789(15) . ?
C12 C17 1.3836(15) . ?
C12 C13 1.4042(14) . ?
C13 C14 1.3911(15) . ?
C13 C19 1.4379(16) . ?
C14 C15 1.3726(17) . ?
C14 H14 0.9300 . ?
C15 C16 1.3747(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.3731(17) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N3 1.1412(13) . ?
C19 N4 1.1409(14) . ?
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
C6 C1 C2 C3 -1.65(16) . . . . ?
N1 C1 C2 C3 178.89(10) . . . . ?
C1 C2 C3 C4 0.29(17) . . . . ?
C2 C3 C4 C5 0.92(18) . . . . ?
C3 C4 C5 C6 -0.77(18) . . . . ?
C4 C5 C6 C1 -0.61(17) . . . . ?
C2 C1 C6 C5 1.82(16) . . . . ?
N1 C1 C6 C5 -178.72(10) . . . . ?
C6 C1 N1 N2 15.32(15) . . . . ?
C2 C1 N1 N2 -165.23(10) . . . . ?
C6 C1 N1 C9 -178.91(10) . . . . ?
C2 C1 N1 C9 0.54(16) . . . . ?
C1 N1 N2 C7 172.97(9) . . . . ?
C9 N1 N2 C7 5.49(12) . . . . ?
N1 N2 C7 C10 -178.64(9) . . . . ?
N1 N2 C7 C8 2.01(12) . . . . ?
N2 C7 C8 C9 -8.05(12) . . . . ?
C10 C7 C8 C9 172.70(11) . . . . ?
N2 N1 C9 C8 -10.13(12) . . . . ?
C1 N1 C9 C8 -176.82(10) . . . . ?
C7 C8 C9 N1 10.06(11) . . . . ?
N2 C7 C10 C11 177.04(10) . . . . ?
C8 C7 C10 C11 -3.74(18) . . . . ?
C7 C10 C11 C18 2.83(17) . . . . ?
C7 C10 C11 C12 -178.80(10) . . . . ?
C10 C11 C12 C17 -136.31(11) . . . . ?
C18 C11 C12 C17 42.17(14) . . . . ?
C10 C11 C12 C13 43.28(15) . . . . ?
C18 C11 C12 C13 -138.24(10) . . . . ?
C17 C12 C13 C14 2.63(15) . . . . ?
C11 C12 C13 C14 -176.97(10) . . . . ?
C17 C12 C13 C19 -171.92(10) . . . . ?
C11 C12 C13 C19 8.48(16) . . . . ?
C12 C13 C14 C15 -0.35(17) . . . . ?
C19 C13 C14 C15 174.35(11) . . . . ?
C13 C14 C15 C16 -1.41(18) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 C12 1.6(2) . . . . ?
C13 C12 C17 C16 -3.27(17) . . . . ?
C11 C12 C17 C16 176.34(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306539
