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#$Date: 2026-05-07 00:01:02 +0200 (Thu 07 de May de 2026) $
#$Revision: 305881 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/57/7135797.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_7135797
loop_
_publ_author_name
'Pattanmarthodiyil, Fathima Thasnim'
'Hariharan, Mahesh'
_publ_section_title
;
 Unlocking Non-Kasha Room Temperature Phosphorescence in Azulene-based
 Cocrystal
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D6CC00894A
_journal_year                    2026
_chemical_formula_moiety         'C10H8, C10H2N4'
_chemical_formula_sum            'C20 H10 N4'
_chemical_formula_weight         306.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-05-04 deposited with the CCDC.	2026-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.9040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3261(3)
_cell_length_b                   12.5443(4)
_cell_length_c                   6.6892(3)
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.79
_cell_volume                     744.67(5)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Apex3 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11017
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_min         2.812
_diffrn_source                   'Sealed microfocus tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/3 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         969
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0320
_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)+(0.0502P)²+0.3546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                909
_reflns_number_total             969
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc00894a2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7135797
_shelx_shelxl_version_number     2019/3
_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   0.982
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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 0.27602(9) 0.11352(6) 0.12016(12) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.13536(8) 0.05613(6) 0.05836(11) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.000000 0.11214(9) 0.000000 0.0142(2) Uani 1 2 d S T P . .
H3 H -0.000002 0.186280 -0.000002 0.017 Uiso 1 2 calc R U P . .
N1 N 0.38813(8) 0.15900(6) 0.17011(11) 0.0215(2) Uani 1 1 d . . . . .
C5 C 0.21414(10) 0.09596(7) 0.59522(13) 0.0216(2) Uani 1 1 d D . . . .
C6 C 0.29242(13) 0.000000 0.62994(18) 0.0218(3) Uani 1 2 d S T P . .
H6 H 0.397212 0.000000 0.676418 0.026 Uiso 1 2 calc R U P . .
C7 C -0.06745(19) 0.12724(15) 0.4740(2) 0.0176(3) Uani 0.5 1 d . . P . .
H7 H -0.048441 0.200122 0.486093 0.021 Uiso 0.5 1 calc R U P . .
C8 C 0.05600(18) 0.05965(14) 0.5282(2) 0.0149(3) Uani 0.5 1 d . . P . .
H5 H 0.2669(14) 0.1600(6) 0.622(2) 0.048(4) Uiso 1 1 d 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
N1 C1 C2 179.72(9) . . ?
C3 C2 C2 120.33(5) . 6 ?
C3 C2 C1 119.70(7) . . ?
C2 C2 C1 119.98(4) 6 . ?
C2 C3 C2 119.35(10) . 2 ?
C2 C3 H3 120.3 . . ?
C2 C3 H3 120.3 2 . ?
C7 C5 C6 136.75(12) 2_556 . ?
C7 C5 C8 34.81(9) 2_556 . ?
C6 C5 C8 102.00(10) . . ?
C7 C5 H5 103.5(9) 2_556 . ?
C6 C5 H5 119.8(9) . . ?
C8 C5 H5 138.2(9) . . ?
C5 C6 C5 120.02(11) 6 . ?
C5 C6 H6 120.0 6 . ?
C5 C6 H6 120.0 . . ?
C5 C7 C8 125.48(15) 2_556 . ?
C5 C7 H7 117.3 2_556 . ?
C8 C7 H7 117.3 . . ?
C5 C7 H7 154.74(15) 2_556 2_556 ?
C8 C7 H7 79.40(15) . 2_556 ?
H7 C7 H7 38.1 . 2_556 ?
C7 C8 C7 59.1(2) 2_556 . ?
C7 C8 C5 65.21(17) 2_556 . ?
C7 C8 C5 124.27(13) . . ?
C7 C8 C8 172.46(17) 2_556 6 ?
C7 C8 C8 127.74(9) . 6 ?
C5 C8 C8 107.98(8) . 6 ?
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 N1 1.1470(11) . ?
C1 C2 1.4411(10) . ?
C2 C3 1.3917(9) . ?
C2 C2 1.4081(15) 6 ?
C3 H3 0.9300 . ?
C5 C7 1.3603(19) 2_556 ?
C5 C6 1.3899(11) . ?
C5 C8 1.4755(17) . ?
C5 H5 0.9302(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9300 . ?
C8 C8 1.496(4) 6 ?
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
C2 C2 C3 C2 0.0 6 . . 2 ?
C1 C2 C3 C2 -179.65(7) . . . 2 ?
C7 C5 C6 C5 -1.7(2) 2_556 . . 6 ?
C8 C5 C6 C5 0.82(14) . . . 6 ?
C5 C7 C8 C7 174.5(3) 2_556 . . 2_556 ?
C5 C7 C8 C5 177.57(11) 2_556 . . . ?
C5 C7 C8 C8 -1.72(18) 2_556 . . 6 ?
C6 C5 C8 C7 -176.94(16) . . . 2_556 ?
C7 C5 C8 C7 -2.90(19) 2_556 . . . ?
C6 C5 C8 C7 -179.84(12) . . . . ?
C7 C5 C8 C8 176.51(16) 2_556 . . 6 ?
C6 C5 C8 C8 -0.43(8) . . . 6 ?
