#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151907.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_7151907
loop_
_publ_author_name
'Jiang, Bo'
'Wang, Xiang'
'Shi, Feng'
'Tu, Shu-Jiang'
'Li, Guigen'
_publ_section_title
;
 New multicomponent cyclization: domino synthesis of pentasubstituted
 pyridines under solvent-free conditions.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4025
_journal_page_last               4028
_journal_paper_doi               10.1039/c0ob01258k
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C16 H19 N5'
_chemical_formula_weight         281.36
_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                 102.451(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.0838(14)
_cell_length_b                   24.279(2)
_cell_length_c                   14.5751(18)
_cell_measurement_reflns_used    1359
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.236
_cell_measurement_theta_min      2.205
_cell_volume                     3138.9(7)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8272
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0828P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                1373
_reflns_number_total             2770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01258k.txt
_cod_data_source_block           090220a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7151907
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4896(3) 0.07355(11) 1.12388(17) 0.0436(7) Uani 1 1 d . . .
N2 N 0.6988(3) 0.05700(12) 1.23599(18) 0.0548(8) Uani 1 1 d . . .
H2A H 0.6444 0.0624 1.2767 0.066 Uiso 1 1 calc R . .
H2B H 0.7928 0.0491 1.2543 0.066 Uiso 1 1 calc R . .
N3 N 0.9971(3) 0.02303(14) 1.1251(2) 0.0703(10) Uani 1 1 d . . .
N4 N 0.7289(3) 0.05221(12) 0.91381(17) 0.0522(8) Uani 1 1 d . . .
H4A H 0.8226 0.0431 0.9278 0.063 Uiso 1 1 calc R . .
H4B H 0.6840 0.0566 0.8560 0.063 Uiso 1 1 calc R . .
N5 N 0.3551(4) 0.08063(15) 0.7912(2) 0.0744(10) Uani 1 1 d . . .
C1 C 0.6380(3) 0.06091(13) 1.1456(2) 0.0402(8) Uani 1 1 d . . .
C2 C 0.7215(3) 0.05283(13) 1.0766(2) 0.0407(8) Uani 1 1 d . . .
C3 C 0.6535(3) 0.05946(13) 0.9816(2) 0.0406(8) Uani 1 1 d . . .
C4 C 0.4994(3) 0.07344(13) 0.9614(2) 0.0421(8) Uani 1 1 d . . .
C5 C 0.4233(3) 0.07915(13) 1.0338(2) 0.0419(8) Uani 1 1 d . . .
C6 C 0.2590(3) 0.09180(14) 1.0138(2) 0.0492(9) Uani 1 1 d . . .
H6A H 0.2162 0.0762 1.0636 0.059 Uiso 1 1 calc R . .
H6B H 0.2111 0.0738 0.9556 0.059 Uiso 1 1 calc R . .
C7 C 0.2220(4) 0.15173(17) 1.0057(3) 0.0729(12) Uani 1 1 d . . .
H7A H 0.2590 0.1673 0.9536 0.087 Uiso 1 1 calc R . .
H7B H 0.2725 0.1704 1.0627 0.087 Uiso 1 1 calc R . .
C8 C 0.0524(4) 0.1615(2) 0.9900(4) 0.0990(16) Uani 1 1 d . . .
H8A H 0.0027 0.1384 0.9382 0.119 Uiso 1 1 calc R . .
H8B H 0.0193 0.1494 1.0457 0.119 Uiso 1 1 calc R . .
C9 C 0.0019(5) 0.2172(2) 0.9701(5) 0.1119(19) Uani 1 1 d . . .
H9 H 0.0465 0.2437 1.0132 0.134 Uiso 1 1 calc R . .
C10 C -0.1006(5) 0.2350(2) 0.8977(4) 0.1027(17) Uani 1 1 d . . .
C11 C -0.1513(6) 0.2932(2) 0.8840(5) 0.140(3) Uani 1 1 d . . .
H11A H -0.1793 0.3075 0.9400 0.169 Uiso 1 1 calc R . .
H11B H -0.0722 0.3162 0.8692 0.169 Uiso 1 1 calc R . .
C12 C -0.2827(7) 0.2915(3) 0.8047(6) 0.157(3) Uani 1 1 d . . .
H12A H -0.3751 0.2911 0.8278 0.188 Uiso 1 1 calc R . .
H12B H -0.2836 0.3238 0.7654 0.188 Uiso 1 1 calc R . .
C13 C -0.2720(8) 0.2418(3) 0.7505(6) 0.168(3) Uani 1 1 d . . .
H13A H -0.2179 0.2491 0.7012 0.201 Uiso 1 1 calc R . .
H13B H -0.3715 0.2279 0.7222 0.201 Uiso 1 1 calc R . .
C14 C -0.1878(7) 0.2016(2) 0.8202(5) 0.148(3) Uani 1 1 d . . .
H14A H -0.2573 0.1775 0.8429 0.178 Uiso 1 1 calc R . .
H14B H -0.1210 0.1793 0.7918 0.178 Uiso 1 1 calc R . .
C15 C 0.8744(4) 0.03671(14) 1.1034(2) 0.0471(9) Uani 1 1 d . . .
C16 C 0.4197(3) 0.07813(15) 0.8671(2) 0.0493(9) 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
C5 N1 C1 118.1(3) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C1 N1 115.6(3) . . ?
N2 C1 C2 122.2(3) . . ?
N1 C1 C2 122.1(3) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 C15 119.6(3) . . ?
C3 C2 C15 120.2(3) . . ?
N4 C3 C2 122.1(3) . . ?
N4 C3 C4 121.7(3) . . ?
C2 C3 C4 116.2(3) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 C16 119.7(3) . . ?
C3 C4 C16 120.1(3) . . ?
N1 C5 C4 123.2(3) . . ?
N1 C5 C6 115.8(3) . . ?
C4 C5 C6 121.0(3) . . ?
C5 C6 C7 114.6(3) . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 111.5(3) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 116.4(4) . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C8 127.5(5) . . ?
C10 C9 H9 116.2 . . ?
C8 C9 H9 116.2 . . ?
C9 C10 C14 127.1(5) . . ?
C9 C10 C11 124.3(5) . . ?
C14 C10 C11 108.6(5) . . ?
C12 C11 C10 104.7(5) . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C11 108.2(5) . . ?
C13 C12 H12A 110.1 . . ?
C11 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 C14 104.9(6) . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C14 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C10 C14 C13 105.9(5) . . ?
C10 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C10 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
N3 C15 C2 179.1(4) . . ?
N5 C16 C4 178.4(4) . . ?
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 C5 1.329(4) . ?
N1 C1 1.351(4) . ?
N2 C1 1.317(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C15 1.140(4) . ?
N4 C3 1.330(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 C16 1.137(4) . ?
C1 C2 1.398(4) . ?
C2 C3 1.399(4) . ?
C2 C15 1.414(4) . ?
C3 C4 1.408(4) . ?
C4 C5 1.388(4) . ?
C4 C16 1.413(4) . ?
C5 C6 1.490(4) . ?
C6 C7 1.492(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.436(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.320(6) . ?
C9 H9 0.9300 . ?
C10 C14 1.474(7) . ?
C10 C11 1.488(7) . ?
C11 C12 1.472(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.456(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.494(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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
C5 N1 C1 N2 178.6(3) . . . . ?
C5 N1 C1 C2 -1.0(4) . . . . ?
N2 C1 C2 C3 -177.6(3) . . . . ?
N1 C1 C2 C3 2.1(5) . . . . ?
N2 C1 C2 C15 3.9(5) . . . . ?
N1 C1 C2 C15 -176.5(3) . . . . ?
C1 C2 C3 N4 180.0(3) . . . . ?
C15 C2 C3 N4 -1.5(5) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C15 C2 C3 C4 177.6(3) . . . . ?
N4 C3 C4 C5 178.2(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
N4 C3 C4 C16 2.3(5) . . . . ?
C2 C3 C4 C16 -176.7(3) . . . . ?
C1 N1 C5 C4 -1.0(5) . . . . ?
C1 N1 C5 C6 178.6(3) . . . . ?
C3 C4 C5 N1 1.9(5) . . . . ?
C16 C4 C5 N1 177.8(3) . . . . ?
C3 C4 C5 C6 -177.6(3) . . . . ?
C16 C4 C5 C6 -1.8(5) . . . . ?
N1 C5 C6 C7 93.0(4) . . . . ?
C4 C5 C6 C7 -87.4(4) . . . . ?
C5 C6 C7 C8 -177.2(4) . . . . ?
C6 C7 C8 C9 -172.9(5) . . . . ?
C7 C8 C9 C10 125.7(6) . . . . ?
C8 C9 C10 C14 0.2(10) . . . . ?
C8 C9 C10 C11 177.5(6) . . . . ?
C9 C10 C11 C12 -170.3(6) . . . . ?
C14 C10 C11 C12 7.4(8) . . . . ?
C10 C11 C12 C13 -22.6(8) . . . . ?
C11 C12 C13 C14 28.8(8) . . . . ?
C9 C10 C14 C13 -172.6(6) . . . . ?
C11 C10 C14 C13 9.8(8) . . . . ?
C12 C13 C14 C10 -23.4(8) . . . . ?
C1 C2 C15 N3 76(26) . . . . ?
C3 C2 C15 N3 -102(26) . . . . ?
C5 C4 C16 N5 -94(13) . . . . ?
C3 C4 C16 N5 82(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26996227
2 PubChem 53468946
