#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025204.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_4025204
loop_
_publ_author_name
'Glenn A. Burley'
'David L. Davies'
'Gerry A. Griffith'
'Michael Lee'
'Kuldip Singh'
_publ_section_title
;
 Cu-Catalyzed N-Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and
 Pyrazoles Using PEG as Solvent Medium
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              980
_journal_page_last               983
_journal_paper_doi               10.1021/jo902466f
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H14 N2'
_chemical_formula_sum            'C17 H14 N2'
_chemical_formula_weight         246.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.71(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.803(13)
_cell_length_b                   5.777(4)
_cell_length_c                   12.736(10)
_cell_measurement_reflns_used    202
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.394
_cell_measurement_theta_min      2.288
_cell_volume                     1309.8(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex 2000 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  0.4838
_diffrn_reflns_av_sigmaI/netI    0.3821
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9019
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.006(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.757
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.757
_refine_ls_R_factor_all          0.2773
_refine_ls_R_factor_gt           0.0994
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.3129
_reflns_number_gt                584
_reflns_number_total             2303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902466f_si_002.cif
_cod_data_source_block           09041
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_database_code               4025204
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2517(3) 0.5646(9) 0.5246(6) 0.0611(18) Uani 1 1 d . . .
N2 N 0.2009(3) 0.5462(9) 0.6858(5) 0.067(2) Uani 1 1 d . . .
C1 C 0.2463(4) 0.4521(11) 0.6182(7) 0.067(2) Uani 1 1 d . . .
H1 H 0.2736 0.3146 0.6333 0.080 Uiso 1 1 calc R . .
C2 C 0.2028(4) 0.7560(10) 0.5320(7) 0.055(2) Uani 1 1 d . . .
C3 C 0.1817(3) 0.9245(10) 0.4596(6) 0.062(2) Uani 1 1 d . . .
H3 H 0.2027 0.9320 0.3915 0.075 Uiso 1 1 calc R . .
C4 C 0.1286(4) 1.0794(10) 0.4927(7) 0.060(2) Uani 1 1 d . . .
C5 C 0.0961(4) 1.0688(11) 0.5924(7) 0.060(2) Uani 1 1 d . . .
C6 C 0.1192(3) 0.8971(10) 0.6615(6) 0.061(2) Uani 1 1 d . . .
H6 H 0.0985 0.8877 0.7298 0.073 Uiso 1 1 calc R . .
C7 C 0.1731(4) 0.7385(10) 0.6295(7) 0.053(2) Uani 1 1 d . . .
C8 C 0.2919(5) 0.5101(11) 0.4398(9) 0.064(3) Uani 1 1 d . . .
C9 C 0.3277(4) 0.4602(12) 0.3640(8) 0.064(3) Uani 1 1 d . . .
C10 C 0.3677(4) 0.4034(11) 0.2725(7) 0.057(2) Uani 1 1 d . . .
C11 C 0.3658(4) 0.5521(12) 0.1876(8) 0.067(2) Uani 1 1 d . . .
H11 H 0.3389 0.6937 0.1922 0.080 Uiso 1 1 calc R . .
C12 C 0.4021(4) 0.4978(13) 0.0973(8) 0.077(3) Uani 1 1 d . . .
H12 H 0.3999 0.6024 0.0398 0.092 Uiso 1 1 calc R . .
C13 C 0.4424(4) 0.2921(13) 0.0875(8) 0.080(3) Uani 1 1 d . . .
H13 H 0.4675 0.2550 0.0243 0.096 Uiso 1 1 calc R . .
C14 C 0.4447(4) 0.1439(13) 0.1727(8) 0.071(3) Uani 1 1 d . . .
H14 H 0.4724 0.0037 0.1684 0.085 Uiso 1 1 calc R . .
C15 C 0.4073(4) 0.1970(11) 0.2639(7) 0.065(2) Uani 1 1 d . . .
H15 H 0.4086 0.0917 0.3212 0.078 Uiso 1 1 calc R . .
C16 C 0.0352(4) 1.2351(10) 0.6236(7) 0.082(3) Uani 1 1 d . . .
H16A H 0.0129 1.1837 0.6896 0.123 Uiso 1 1 calc R . .
H16B H -0.0037 1.2399 0.5685 0.123 Uiso 1 1 calc R . .
H16C H 0.0566 1.3901 0.6331 0.123 Uiso 1 1 calc R . .
C17 C 0.1015(4) 1.2612(10) 0.4161(6) 0.083(3) Uani 1 1 d . . .
H17A H 0.1279 1.2436 0.3496 0.125 Uiso 1 1 calc R . .
H17B H 0.1115 1.4154 0.4452 0.125 Uiso 1 1 calc R . .
H17C H 0.0474 1.2428 0.4039 0.125 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
C8 N1 C1 129.6(6) . . ?
C8 N1 C2 125.0(7) . . ?
C1 N1 C2 105.4(7) . . ?
C1 N2 C7 102.1(7) . . ?
N2 C1 N1 115.4(7) . . ?
N2 C1 H1 122.3 . . ?
N1 C1 H1 122.3 . . ?
C7 C2 C3 123.5(7) . . ?
C7 C2 N1 104.5(7) . . ?
C3 C2 N1 131.8(9) . . ?
C4 C3 C2 115.8(8) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C3 C4 C5 122.9(7) . . ?
C3 C4 C17 118.1(8) . . ?
C5 C4 C17 118.9(7) . . ?
C6 C5 C4 119.0(7) . . ?
C6 C5 C16 119.9(8) . . ?
C4 C5 C16 121.1(7) . . ?
C5 C6 C7 119.0(8) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 119.8(7) . . ?
C2 C7 N2 112.6(7) . . ?
C6 C7 N2 127.5(8) . . ?
C9 C8 N1 179.7(9) . . ?
C8 C9 C10 178.0(7) . . ?
C11 C10 C15 118.7(8) . . ?
C11 C10 C9 119.6(7) . . ?
C15 C10 C9 121.7(8) . . ?
C12 C11 C10 120.7(8) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.4(8) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.9(9) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C15 C14 C13 120.9(7) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 120.4(8) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C8 1.342(10) . ?
N1 C1 1.362(8) . ?
N1 C2 1.410(8) . ?
N2 C1 1.306(8) . ?
N2 C7 1.409(7) . ?
C1 H1 0.9500 . ?
C2 C7 1.359(9) . ?
C2 C3 1.390(9) . ?
C3 C4 1.372(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(10) . ?
C4 C17 1.509(8) . ?
C5 C6 1.385(9) . ?
C5 C16 1.507(9) . ?
C6 C7 1.391(9) . ?
C6 H6 0.9500 . ?
C8 C9 1.199(11) . ?
C9 C10 1.412(11) . ?
C10 C11 1.380(9) . ?
C10 C15 1.390(9) . ?
C11 C12 1.363(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(10) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
C7 N2 C1 N1 0.9(7) . . . . ?
C8 N1 C1 N2 -178.8(6) . . . . ?
C2 N1 C1 N2 -0.6(7) . . . . ?
C8 N1 C2 C7 178.3(6) . . . . ?
C1 N1 C2 C7 0.0(6) . . . . ?
C8 N1 C2 C3 2.4(10) . . . . ?
C1 N1 C2 C3 -175.9(6) . . . . ?
C7 C2 C3 C4 1.0(9) . . . . ?
N1 C2 C3 C4 176.2(6) . . . . ?
C2 C3 C4 C5 -1.0(9) . . . . ?
C2 C3 C4 C17 -177.9(5) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C17 C4 C5 C6 177.9(5) . . . . ?
C3 C4 C5 C16 -176.9(6) . . . . ?
C17 C4 C5 C16 0.0(9) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C16 C5 C6 C7 177.1(5) . . . . ?
C3 C2 C7 C6 -0.9(9) . . . . ?
N1 C2 C7 C6 -177.2(5) . . . . ?
C3 C2 C7 N2 176.9(5) . . . . ?
N1 C2 C7 N2 0.6(7) . . . . ?
C5 C6 C7 C2 0.8(8) . . . . ?
C5 C6 C7 N2 -176.6(5) . . . . ?
C1 N2 C7 C2 -0.9(7) . . . . ?
C1 N2 C7 C6 176.7(6) . . . . ?
C1 N1 C8 C9 51(100) . . . . ?
C2 N1 C8 C9 -127(100) . . . . ?
N1 C8 C9 C10 85(100) . . . . ?
C8 C9 C10 C11 47(23) . . . . ?
C8 C9 C10 C15 -131(23) . . . . ?
C15 C10 C11 C12 -0.1(9) . . . . ?
C9 C10 C11 C12 -178.0(6) . . . . ?
C10 C11 C12 C13 -0.3(10) . . . . ?
C11 C12 C13 C14 -0.1(10) . . . . ?
C12 C13 C14 C15 0.9(10) . . . . ?
C13 C14 C15 C10 -1.3(10) . . . . ?
C11 C10 C15 C14 0.9(9) . . . . ?
C9 C10 C15 C14 178.8(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659139
2 PubChem 46178172
