#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151005.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_7151005
loop_
_publ_author_name
'Guan, Xiao-Yang'
'Shi, Min'
_publ_section_title
;
 A convenient three-component reaction leading to the synthesis of
 polysubstituted cyclohexene derivatives
;
_journal_issue                   19
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3616
_journal_page_last               3620
_journal_paper_doi               10.1039/b810299f
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C21 H15 N5 O2'
_chemical_formula_weight         369.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 117.874(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2254(13)
_cell_length_b                   11.3377(12)
_cell_length_c                   14.1441(15)
_cell_measurement_reflns_used    1714
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.785
_cell_measurement_theta_min      4.850
_cell_volume                     1874.8(3)
_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      293(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  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10802
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86356
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0561
_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)+(0.0363P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2733
_reflns_number_total             4078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810299f.txt
_cod_data_source_block           cd28232
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151005
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.22827(16) 0.42903(16) 0.30156(15) 0.0562(5) Uani 1 1 d . . .
N2 N 0.45894(16) 0.15244(17) 0.32992(15) 0.0640(6) Uani 1 1 d . . .
N3 N 0.12857(16) 0.17565(17) 0.15552(16) 0.0418(5) Uani 1 1 d . . .
N4 N 0.03163(15) 0.04085(16) -0.09619(14) 0.0529(5) Uani 1 1 d . . .
N5 N 0.44638(16) 0.34339(15) 0.02372(16) 0.0435(4) Uani 1 1 d . . .
O1 O 0.54836(13) 0.34564(15) 0.08301(14) 0.0703(5) Uani 1 1 d . . .
O2 O 0.39940(15) 0.38957(15) -0.06346(14) 0.0689(5) Uani 1 1 d . . .
C1 C 0.35623(15) 0.36552(15) 0.14026(14) 0.0320(4) Uani 1 1 d . . .
H1 H 0.4324 0.3869 0.1968 0.038 Uiso 1 1 calc R . .
C2 C 0.29821(15) 0.29178(16) 0.19520(14) 0.0319(4) Uani 1 1 d . . .
C3 C 0.19992(14) 0.21311(15) 0.11763(14) 0.0298(4) Uani 1 1 d . . .
C4 C 0.19105(15) 0.18441(15) 0.02152(14) 0.0311(4) Uani 1 1 d . . .
C5 C 0.26623(15) 0.23041(16) -0.02535(14) 0.0323(4) Uani 1 1 d . . .
H5 H 0.2255 0.2940 -0.0758 0.039 Uiso 1 1 calc R . .
C6 C 0.37486(15) 0.28042(16) 0.06516(14) 0.0326(4) Uani 1 1 d . . .
H6 H 0.4200 0.2138 0.1085 0.039 Uiso 1 1 calc R . .
C7 C 0.25873(16) 0.37094(17) 0.25460(15) 0.0371(5) Uani 1 1 d . . .
C8 C 0.38710(17) 0.21198(18) 0.27366(16) 0.0392(5) Uani 1 1 d . . .
C9 C 0.10235(17) 0.10492(17) -0.04405(15) 0.0357(5) Uani 1 1 d . . .
C10 C 0.29652(17) 0.47996(16) 0.09029(15) 0.0345(5) Uani 1 1 d . . .
C11 C 0.17974(18) 0.48957(18) 0.02456(16) 0.0447(5) Uani 1 1 d . . .
H11 H 0.1335 0.4231 0.0091 0.054 Uiso 1 1 calc R . .
C12 C 0.1316(2) 0.5976(2) -0.01808(18) 0.0579(6) Uani 1 1 d . . .
H12 H 0.0532 0.6033 -0.0625 0.070 Uiso 1 1 calc R . .
C13 C 0.1989(3) 0.6968(2) 0.0047(2) 0.0667(7) Uani 1 1 d . . .
H13 H 0.1661 0.7694 -0.0236 0.080 Uiso 1 1 calc R . .
C14 C 0.3143(3) 0.6879(2) 0.0693(2) 0.0625(7) Uani 1 1 d . . .
H14 H 0.3599 0.7549 0.0848 0.075 Uiso 1 1 calc R . .
C15 C 0.3635(2) 0.58071(18) 0.11149(17) 0.0467(6) Uani 1 1 d . . .
H15 H 0.4422 0.5756 0.1545 0.056 Uiso 1 1 calc R . .
C16 C 0.29476(16) 0.13400(17) -0.08442(15) 0.0359(5) Uani 1 1 d . . .
C17 C 0.33217(18) 0.02514(18) -0.03902(18) 0.0478(6) Uani 1 1 d . . .
H17 H 0.3378 0.0087 0.0277 0.057 Uiso 1 1 calc R . .
C18 C 0.3615(2) -0.0603(2) -0.0915(2) 0.0619(7) Uani 1 1 d . . .
H18 H 0.3868 -0.1338 -0.0599 0.074 Uiso 1 1 calc R . .
C19 C 0.3536(2) -0.0376(2) -0.1893(2) 0.0672(7) Uani 1 1 d . . .
H19 H 0.3740 -0.0950 -0.2242 0.081 Uiso 1 1 calc R . .
C20 C 0.3159(2) 0.0696(3) -0.2355(2) 0.0777(8) Uani 1 1 d . . .
H20 H 0.3102 0.0851 -0.3024 0.093 Uiso 1 1 calc R . .
C21 C 0.2859(2) 0.1553(2) -0.18413(17) 0.0598(7) Uani 1 1 d . . .
H21 H 0.2596 0.2281 -0.2168 0.072 Uiso 1 1 calc R . .
H3A H 0.0835(16) 0.1160(18) 0.1231(16) 0.044(6) Uiso 1 1 d . . .
H3B H 0.1458(17) 0.1846(19) 0.2230(18) 0.059(7) Uiso 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'
O O 0.0106 0.0060 '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
C3 N3 H3A 117.6(12) . . ?
C3 N3 H3B 121.4(14) . . ?
H3A N3 H3B 115.2(19) . . ?
O2 N5 O1 124.88(18) . . ?
O2 N5 C6 119.02(17) . . ?
O1 N5 C6 116.08(18) . . ?
C10 C1 C6 115.65(15) . . ?
C10 C1 C2 114.87(14) . . ?
C6 C1 C2 106.37(14) . . ?
C10 C1 H1 106.4 . . ?
C6 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C7 C2 C8 108.09(15) . . ?
C7 C2 C3 110.62(14) . . ?
C8 C2 C3 106.84(15) . . ?
C7 C2 C1 110.03(15) . . ?
C8 C2 C1 107.18(14) . . ?
C3 C2 C1 113.80(14) . . ?
C4 C3 N3 125.13(17) . . ?
C4 C3 C2 120.42(15) . . ?
N3 C3 C2 114.44(16) . . ?
C3 C4 C9 117.76(16) . . ?
C3 C4 C5 126.14(16) . . ?
C9 C4 C5 116.09(15) . . ?
C6 C5 C4 108.30(14) . . ?
C6 C5 C16 110.51(14) . . ?
C4 C5 C16 111.84(15) . . ?
C6 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C16 C5 H5 108.7 . . ?
N5 C6 C5 111.59(15) . . ?
N5 C6 C1 107.71(14) . . ?
C5 C6 C1 115.01(14) . . ?
N5 C6 H6 107.4 . . ?
C5 C6 H6 107.4 . . ?
C1 C6 H6 107.4 . . ?
N1 C7 C2 178.2(2) . . ?
N2 C8 C2 175.4(2) . . ?
N4 C9 C4 179.7(3) . . ?
C11 C10 C15 118.58(19) . . ?
C11 C10 C1 123.79(17) . . ?
C15 C10 C1 117.63(18) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C21 118.38(19) . . ?
C17 C16 C5 121.01(17) . . ?
C21 C16 C5 120.59(18) . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
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 C7 1.135(2) . ?
N2 C8 1.133(2) . ?
N3 C3 1.353(2) . ?
N3 H3A 0.88(2) . ?
N3 H3B 0.88(2) . ?
N4 C9 1.141(2) . ?
N5 O2 1.210(2) . ?
N5 O1 1.211(2) . ?
N5 C6 1.505(2) . ?
C1 C10 1.512(2) . ?
C1 C6 1.538(2) . ?
C1 C2 1.565(2) . ?
C1 H1 0.9800 . ?
C2 C7 1.481(3) . ?
C2 C8 1.487(3) . ?
C2 C3 1.535(2) . ?
C3 C4 1.349(2) . ?
C4 C9 1.425(3) . ?
C4 C5 1.522(2) . ?
C5 C6 1.518(2) . ?
C5 C16 1.526(2) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C10 C11 1.385(3) . ?
C10 C15 1.389(2) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.372(3) . ?
C16 C21 1.381(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A N4 0.88(2) 2.26(2) 3.091(3) 159.6(17) 3
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
C10 C1 C2 C7 -40.9(2) . . . . ?
C6 C1 C2 C7 -170.18(14) . . . . ?
C10 C1 C2 C8 -158.18(15) . . . . ?
C6 C1 C2 C8 72.51(17) . . . . ?
C10 C1 C2 C3 83.92(19) . . . . ?
C6 C1 C2 C3 -45.39(19) . . . . ?
C7 C2 C3 C4 143.89(17) . . . . ?
C8 C2 C3 C4 -98.68(19) . . . . ?
C1 C2 C3 C4 19.4(2) . . . . ?
C7 C2 C3 N3 -37.5(2) . . . . ?
C8 C2 C3 N3 79.96(19) . . . . ?
C1 C2 C3 N3 -161.95(16) . . . . ?
N3 C3 C4 C9 -2.5(3) . . . . ?
C2 C3 C4 C9 175.99(16) . . . . ?
N3 C3 C4 C5 176.55(17) . . . . ?
C2 C3 C4 C5 -5.0(3) . . . . ?
C3 C4 C5 C6 18.4(2) . . . . ?
C9 C4 C5 C6 -162.53(16) . . . . ?
C3 C4 C5 C16 140.43(18) . . . . ?
C9 C4 C5 C16 -40.5(2) . . . . ?
O2 N5 C6 C5 29.3(2) . . . . ?
O1 N5 C6 C5 -152.22(17) . . . . ?
O2 N5 C6 C1 -97.8(2) . . . . ?
O1 N5 C6 C1 80.6(2) . . . . ?
C4 C5 C6 N5 -171.84(14) . . . . ?
C16 C5 C6 N5 65.33(19) . . . . ?
C4 C5 C6 C1 -48.8(2) . . . . ?
C16 C5 C6 C1 -171.61(15) . . . . ?
C10 C1 C6 N5 59.6(2) . . . . ?
C2 C1 C6 N5 -171.57(15) . . . . ?
C10 C1 C6 C5 -65.5(2) . . . . ?
C2 C1 C6 C5 63.32(19) . . . . ?
C8 C2 C7 N1 -46(7) . . . . ?
C3 C2 C7 N1 70(7) . . . . ?
C1 C2 C7 N1 -163(7) . . . . ?
C7 C2 C8 N2 -137(3) . . . . ?
C3 C2 C8 N2 104(3) . . . . ?
C1 C2 C8 N2 -18(3) . . . . ?
C3 C4 C9 N4 -70(40) . . . . ?
C5 C4 C9 N4 111(40) . . . . ?
C6 C1 C10 C11 77.2(2) . . . . ?
C2 C1 C10 C11 -47.4(2) . . . . ?
C6 C1 C10 C15 -102.46(19) . . . . ?
C2 C1 C10 C15 132.98(17) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C1 C10 C11 C12 -179.99(18) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C1 C10 C15 C14 -179.37(18) . . . . ?
C6 C5 C16 C17 73.3(2) . . . . ?
C4 C5 C16 C17 -47.5(2) . . . . ?
C6 C5 C16 C21 -105.3(2) . . . . ?
C4 C5 C16 C21 133.99(19) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
C5 C16 C17 C18 -177.79(18) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C16 0.5(4) . . . . ?
C17 C16 C21 C20 -1.0(3) . . . . ?
C5 C16 C21 C20 177.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9123863
2 PubChem 102392324
