#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025298.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_4025298
loop_
_publ_author_name
'Mominul Sinan'
'Kumaresh Ghosh'
'Sreebrata Goswami'
_publ_section_title
;
 One-Pot Synthesis of Linearly Fused N-Heterocyles from Their Angular
 Analogues and Studies of Their Redox and Electrochromic Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2065
_journal_page_last               2068
_journal_paper_doi               10.1021/jo902432w
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.660(17)
_cell_angle_beta                 93.716(16)
_cell_angle_gamma                93.664(16)
_cell_formula_units_Z            2
_cell_length_a                   6.882(4)
_cell_length_b                   7.400(4)
_cell_length_c                   14.123(8)
_cell_measurement_reflns_used    703
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.42
_cell_measurement_theta_min      2.97
_cell_volume                     707.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5297
_diffrn_reflns_theta_full        20.72
_diffrn_reflns_theta_max         20.72
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.377
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.377
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.1183
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3970
_refine_ls_wR_factor_ref         0.4058
_reflns_number_gt                850
_reflns_number_total             1438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902432w_si_005.cif
_cod_data_source_block           ms49_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025298
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5452(15) 0.6391(14) 0.2605(8) 0.059(3) Uani 1 1 d . . .
N3 N 0.4244(14) 0.7860(13) -0.1038(8) 0.052(3) Uani 1 1 d . . .
N12 N 0.8144(13) 0.8106(13) -0.0251(8) 0.050(3) Uani 1 1 d . . .
N20 N 0.5813(14) 0.8336(13) -0.1528(7) 0.047(3) Uani 1 1 d . . .
C15 C 0.5372(17) 0.6753(16) 0.1722(10) 0.049(3) Uani 1 1 d . . .
C16 C 0.3369(17) 0.6646(16) 0.1241(10) 0.060(4) Uani 1 1 d . . .
H16 H 0.2310 0.6312 0.1571 0.072 Uiso 1 1 calc R . .
C17 C 0.3055(17) 0.7012(16) 0.0359(10) 0.052(4) Uani 1 1 d . . .
H17 H 0.1781 0.6936 0.0085 0.063 Uiso 1 1 calc R . .
C18 C 0.4623(16) 0.7520(15) -0.0183(9) 0.044(3) Uani 1 1 d . . .
C19 C 0.6926(17) 0.7270(16) 0.1187(9) 0.048(3) Uani 1 1 d . . .
H19 H 0.8193 0.7381 0.1473 0.058 Uiso 1 1 calc R . .
C20 C 0.9164(18) 0.9034(16) -0.1700(9) 0.055(4) Uani 1 1 d . . .
H20 H 1.0464 0.9137 -0.1459 0.066 Uiso 1 1 calc R . .
C21 C 0.874(2) 0.9421(19) -0.2578(10) 0.064(4) Uani 1 1 d . . .
H21 H 0.9736 0.9795 -0.2936 0.077 Uiso 1 1 calc R . .
C22 C 0.679(2) 0.9265(18) -0.2967(9) 0.065(4) Uani 1 1 d . . .
H22 H 0.6486 0.9529 -0.3580 0.078 Uiso 1 1 calc R . .
C33 C 0.6641(17) 0.7613(15) 0.0269(9) 0.046(3) Uani 1 1 d . . .
C35 C 0.7718(17) 0.8478(15) -0.1125(9) 0.046(3) Uani 1 1 d . . .
C37 C 0.538(2) 0.8727(19) -0.2433(10) 0.070(4) Uani 1 1 d . . .
H37 H 0.4084 0.8618 -0.2682 0.084 Uiso 1 1 calc R . .
C101 C 0.8821(19) 0.5388(18) 0.2825(9) 0.058(4) Uani 1 1 d . . .
H101 H 0.8685 0.4623 0.2235 0.069 Uiso 1 1 calc R . .
C102 C 1.0540(18) 0.547(2) 0.3410(10) 0.064(4) Uani 1 1 d . . .
H102 H 1.1521 0.4721 0.3214 0.077 Uiso 1 1 calc R . .
C103 C 1.0822(19) 0.663(2) 0.4274(10) 0.061(4) Uani 1 1 d . . .
C104 C 0.932(2) 0.7684(19) 0.4546(9) 0.069(4) Uani 1 1 d . . .
H104 H 0.9476 0.8475 0.5128 0.083 Uiso 1 1 calc R . .
C105 C 0.761(2) 0.7610(19) 0.3992(10) 0.065(4) Uani 1 1 d . . .
H105 H 0.6627 0.8349 0.4203 0.078 Uiso 1 1 calc R . .
C106 C 0.7304(18) 0.6446(17) 0.3119(9) 0.049(3) Uani 1 1 d . . .
C131 C 1.2657(19) 0.679(2) 0.4903(10) 0.093(5) Uani 1 1 d . . .
H13A H 1.2439 0.6194 0.5451 0.140 Uiso 1 1 calc R . .
H13B H 1.3061 0.8057 0.5114 0.140 Uiso 1 1 calc R . .
H13C H 1.3657 0.6209 0.4551 0.140 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'
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
C15 N1 C106 119.0(11) . . ?
C18 N3 N20 116.8(10) . . ?
C35 N12 C33 118.3(10) . . ?
C37 N20 N3 115.9(11) . . ?
C37 N20 C35 121.7(12) . . ?
N3 N20 C35 122.4(10) . . ?
N1 C15 C19 128.4(12) . . ?
N1 C15 C16 114.9(11) . . ?
C19 C15 C16 116.6(12) . . ?
C17 C16 C15 121.8(12) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 121.5(12) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
N3 C18 C17 119.2(11) . . ?
N3 C18 C33 122.7(11) . . ?
C17 C18 C33 118.1(12) . . ?
C33 C19 C15 122.6(12) . . ?
C33 C19 H19 118.7 . . ?
C15 C19 H19 118.7 . . ?
C21 C20 C35 122.3(13) . . ?
C21 C20 H20 118.9 . . ?
C35 C20 H20 118.9 . . ?
C20 C21 C22 120.3(13) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C37 C22 C21 118.6(13) . . ?
C37 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C19 C33 N12 122.6(11) . . ?
C19 C33 C18 119.3(12) . . ?
N12 C33 C18 118.0(11) . . ?
N12 C35 N20 121.9(11) . . ?
N12 C35 C20 122.1(11) . . ?
N20 C35 C20 116.0(12) . . ?
C22 C37 N20 121.1(13) . . ?
C22 C37 H37 119.5 . . ?
N20 C37 H37 119.5 . . ?
C102 C101 C106 120.3(13) . . ?
C102 C101 H101 119.8 . . ?
C106 C101 H101 119.8 . . ?
C103 C102 C101 121.5(13) . . ?
C103 C102 H102 119.3 . . ?
C101 C102 H102 119.3 . . ?
C104 C103 C102 117.4(12) . . ?
C104 C103 C131 119.8(14) . . ?
C102 C103 C131 122.8(15) . . ?
C105 C104 C103 122.3(13) . . ?
C105 C104 H104 118.8 . . ?
C103 C104 H104 118.8 . . ?
C104 C105 C106 120.9(13) . . ?
C104 C105 H105 119.6 . . ?
C106 C105 H105 119.6 . . ?
C105 C106 C101 117.6(12) . . ?
C105 C106 N1 117.5(12) . . ?
C101 C106 N1 124.9(12) . . ?
C103 C131 H13A 109.5 . . ?
C103 C131 H13B 109.5 . . ?
H13A C131 H13B 109.5 . . ?
C103 C131 H13C 109.5 . . ?
H13A C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
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
N1 C15 1.313(14) . ?
N1 C106 1.421(15) . ?
N3 C18 1.284(14) . ?
N3 N20 1.376(12) . ?
N12 C35 1.323(14) . ?
N12 C33 1.368(14) . ?
N20 C37 1.371(15) . ?
N20 C35 1.386(14) . ?
C15 C19 1.415(16) . ?
C15 C16 1.488(16) . ?
C16 C17 1.322(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.426(16) . ?
C17 H17 0.9300 . ?
C18 C33 1.483(15) . ?
C19 C33 1.363(15) . ?
C19 H19 0.9300 . ?
C20 C21 1.333(16) . ?
C20 C35 1.405(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.407(17) . ?
C21 H21 0.9300 . ?
C22 C37 1.344(16) . ?
C22 H22 0.9300 . ?
C37 H37 0.9300 . ?
C101 C102 1.391(16) . ?
C101 C106 1.392(16) . ?
C101 H101 0.9300 . ?
C102 C103 1.378(17) . ?
C102 H102 0.9300 . ?
C103 C104 1.373(18) . ?
C103 C131 1.484(16) . ?
C104 C105 1.366(17) . ?
C104 H104 0.9300 . ?
C105 C106 1.389(16) . ?
C105 H105 0.9300 . ?
C131 H13A 0.9600 . ?
C131 H13B 0.9600 . ?
C131 H13C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659162
2 PubChem 45276691
