#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151070.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_7151070
loop_
_publ_author_name
'Tu, Shujiang'
'Zhang, Junyong'
'Jia, Runhong'
'Jiang, Bo'
'Zhang, Yan'
'Jiang, Hong'
_publ_section_title
;
 An efficient route for the synthesis of a new class of
 pyrido[2,3-d]pyrimidine derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1450
_journal_page_last               1453
_journal_paper_doi               10.1039/b617201f
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C21.75 H18.5 N3 O4.25'
_chemical_formula_weight         389.90
_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                 106.34(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.383(2)
_cell_length_b                   9.9133(12)
_cell_length_c                   23.371(3)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.007
_cell_measurement_theta_min      2.357
_cell_volume                     4087.0(9)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10398
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0641
_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)+(0.0910P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.2072
_reflns_number_gt                1519
_reflns_number_total             3575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b617201f.txt
_cod_data_source_block           060110c
_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_cell_volume        4087.0(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C21.75 H18.50 N3 O4.25'
_cod_database_code               7151070
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 0.95736(17) 0.0846(3) 0.92686(14) 0.0438(9) Uani 1 1 d . . .
H1 H 0.9713 0.0062 0.9416 0.053 Uiso 1 1 calc R . .
N2 N 1.01143(19) 0.5263(3) 0.91693(15) 0.0503(9) Uani 1 1 d . . .
N3 N 0.7055(3) 0.5160(4) 0.99350(19) 0.0633(11) Uani 1 1 d . . .
O1 O 0.99825(14) 0.1751(2) 1.01888(12) 0.0435(7) Uani 1 1 d . . .
O2 O 0.94670(15) 0.5869(3) 0.92760(12) 0.0544(8) Uani 1 1 d . . .
H2 H 0.9493 0.6690 0.9245 0.082 Uiso 1 1 calc R . .
O3 O 0.7551(2) 0.5960(4) 1.0142(2) 0.1060(15) Uani 1 1 d . . .
O4 O 0.6443(2) 0.5217(4) 1.0029(2) 0.1126(15) Uani 1 1 d . . .
O5 O 1.0000 0.4771(18) 0.7500 0.193(7) Uani 0.50 2 d SPDU . .
C1 C 0.9688(2) 0.1895(4) 0.96406(18) 0.0362(9) Uani 1 1 d . . .
C2 C 0.9450(2) 0.3259(4) 0.93724(16) 0.0365(9) Uani 1 1 d . . .
H2A H 0.9316 0.3802 0.9678 0.044 Uiso 1 1 calc R . .
C3 C 0.8735(2) 0.3186(4) 0.88276(16) 0.0377(9) Uani 1 1 d . . .
H3 H 0.8711 0.4034 0.8607 0.045 Uiso 1 1 calc R . .
C4 C 0.8813(2) 0.2054(4) 0.84097(17) 0.0403(10) Uani 1 1 d . . .
C5 C 0.9238(2) 0.0942(4) 0.86477(17) 0.0434(10) Uani 1 1 d . . .
C6 C 0.9351(2) -0.0137(4) 0.8283(2) 0.0546(12) Uani 1 1 d . . .
H6 H 0.9645 -0.0876 0.8453 0.066 Uiso 1 1 calc R . .
C7 C 0.9029(3) -0.0084(5) 0.7688(2) 0.0626(13) Uani 1 1 d . . .
H7 H 0.9108 -0.0788 0.7450 0.075 Uiso 1 1 calc R . .
C8 C 0.8570(2) 0.1029(5) 0.74196(19) 0.0527(11) Uani 1 1 d . . .
C9 C 0.8220(3) 0.1067(6) 0.6800(2) 0.0713(14) Uani 1 1 d . . .
H9 H 0.8306 0.0369 0.6561 0.086 Uiso 1 1 calc R . .
C10 C 0.7757(3) 0.2108(6) 0.6545(2) 0.0760(16) Uani 1 1 d . . .
H10 H 0.7524 0.2117 0.6136 0.091 Uiso 1 1 calc R . .
C11 C 0.7637(3) 0.3166(5) 0.6907(2) 0.0721(15) Uani 1 1 d . . .
H11 H 0.7322 0.3876 0.6733 0.087 Uiso 1 1 calc R . .
C12 C 0.7972(3) 0.3179(5) 0.7506(2) 0.0599(12) Uani 1 1 d . . .
H12 H 0.7882 0.3893 0.7735 0.072 Uiso 1 1 calc R . .
C13 C 0.8460(2) 0.2102(4) 0.77847(17) 0.0464(11) Uani 1 1 d . . .
C14 C 1.0095(2) 0.3977(4) 0.92141(17) 0.0417(10) Uani 1 1 d . . .
C15 C 1.0735(2) 0.3208(4) 0.9095(2) 0.0665(14) Uani 1 1 d . . .
H15A H 1.1082 0.3826 0.8994 0.100 Uiso 1 1 calc R . .
H15B H 1.0541 0.2597 0.8769 0.100 Uiso 1 1 calc R . .
H15C H 1.0994 0.2708 0.9444 0.100 Uiso 1 1 calc R . .
C16 C 0.8011(2) 0.3101(4) 0.90248(16) 0.0400(10) Uani 1 1 d . . .
C17 C 0.7866(2) 0.4102(4) 0.93925(17) 0.0419(10) Uani 1 1 d . . .
H17 H 0.8217 0.4787 0.9532 0.050 Uiso 1 1 calc R . .
C18 C 0.7197(2) 0.4073(4) 0.95499(17) 0.0448(10) Uani 1 1 d . . .
C19 C 0.6659(2) 0.3090(5) 0.93562(19) 0.0542(12) Uani 1 1 d . . .
H19 H 0.6210 0.3096 0.9466 0.065 Uiso 1 1 calc R . .
C20 C 0.6804(3) 0.2101(5) 0.8996(2) 0.0635(13) Uani 1 1 d . . .
H20 H 0.6450 0.1420 0.8860 0.076 Uiso 1 1 calc R . .
C21 C 0.7472(2) 0.2098(4) 0.88295(19) 0.0533(11) Uani 1 1 d . . .
H21 H 0.7559 0.1415 0.8584 0.064 Uiso 1 1 calc R . .
C22 C 1.0000 0.601(2) 0.7500 0.179(9) Uani 0.50 2 d SPDU . .
C23 C 1.0043(8) 0.6881(11) 0.7972(6) 0.112(4) Uani 0.50 1 d PDU . .
H23A H 1.0074 0.6370 0.8327 0.169 Uiso 0.50 1 calc PR . .
H23B H 0.9598 0.7440 0.7883 0.169 Uiso 0.50 1 calc PR . .
H23C H 1.0485 0.7438 0.8033 0.169 Uiso 0.50 1 calc PR . .
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
C1 N1 C5 124.1(3) . . ?
C1 N1 H1 117.9 . . ?
C5 N1 H1 117.9 . . ?
C14 N2 O2 111.3(3) . . ?
O3 N3 O4 122.5(5) . . ?
O3 N3 C18 118.8(4) . . ?
O4 N3 C18 118.7(5) . . ?
N2 O2 H2 109.5 . . ?
O1 C1 N1 121.5(3) . . ?
O1 C1 C2 121.4(3) . . ?
N1 C1 C2 117.1(4) . . ?
C1 C2 C14 111.7(3) . . ?
C1 C2 C3 112.3(3) . . ?
C14 C2 C3 111.2(3) . . ?
C1 C2 H2A 107.1 . . ?
C14 C2 H2A 107.1 . . ?
C3 C2 H2A 107.1 . . ?
C4 C3 C16 113.7(3) . . ?
C4 C3 C2 110.4(3) . . ?
C16 C3 C2 111.3(3) . . ?
C4 C3 H3 107.0 . . ?
C16 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C5 C4 C13 119.0(4) . . ?
C5 C4 C3 118.5(3) . . ?
C13 C4 C3 122.4(3) . . ?
C4 C5 N1 120.3(4) . . ?
C4 C5 C6 121.6(4) . . ?
N1 C5 C6 118.1(4) . . ?
C7 C6 C5 119.5(4) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C13 119.9(4) . . ?
C9 C8 C7 121.1(4) . . ?
C13 C8 C7 119.0(4) . . ?
C10 C9 C8 121.2(5) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 121.7(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.3(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C4 119.6(4) . . ?
C8 C13 C12 117.8(4) . . ?
C4 C13 C12 122.6(4) . . ?
N2 C14 C15 116.8(4) . . ?
N2 C14 C2 122.0(3) . . ?
C15 C14 C2 121.2(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.2(4) . . ?
C17 C16 C3 118.9(3) . . ?
C21 C16 C3 122.9(4) . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 122.8(4) . . ?
C19 C18 N3 119.0(4) . . ?
C17 C18 N3 118.2(4) . . ?
C20 C19 C18 117.7(4) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 C21 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C16 C21 C20 120.8(4) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
O5 C22 C23 128.7(9) . . ?
O5 C22 C23 128.7(9) . 2_756 ?
C23 C22 C23 102.6(17) . 2_756 ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 C1 1.334(5) . ?
N1 C5 1.411(5) . ?
N1 H1 0.8600 . ?
N2 C14 1.280(5) . ?
N2 O2 1.416(4) . ?
N3 O3 1.203(5) . ?
N3 O4 1.206(4) . ?
N3 C18 1.474(6) . ?
O1 C1 1.251(4) . ?
O2 H2 0.8200 . ?
O5 C22 1.224(15) . ?
C1 C2 1.502(5) . ?
C2 C14 1.514(5) . ?
C2 C3 1.554(5) . ?
C2 H2A 0.9800 . ?
C3 C4 1.521(5) . ?
C3 C16 1.527(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.375(5) . ?
C4 C13 1.422(5) . ?
C5 C6 1.418(5) . ?
C6 C7 1.351(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.423(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(6) . ?
C8 C13 1.413(6) . ?
C9 C10 1.364(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.429(6) . ?
C12 H12 0.9300 . ?
C14 C15 1.493(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.387(5) . ?
C16 C21 1.387(5) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(6) . ?
C19 C20 1.367(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.388(12) . ?
C22 C23 1.388(12) 2_756 ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190363
