A domino desulfurative coupling-acylation-hydration-Michael addition process for the synthesis of polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines
Zhong-Fei Yan; Zheng-Jun Quan; Yu-Xia Da; Zhang Zhang; Xi-Cun Wang; Chem.Commun. 50 (2014) 13555–; doi:10.1039/C4cc05090H

data_7115862
_publ_section_title
;
 A domino desulfurative coupling-acylation-hydration-Michael addition
 process for the synthesis of polysubstituted
 tetrahydro-4H-pyrido[1,2-a]pyrimidines
;
_journal_name_full               Chem.Commun.
_journal_page_first              13555
_journal_paper_doi               10.1039/C4cc05090H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C26 H26 N2 O5'
_chemical_formula_sum            'C26 H26 N2 O5'
_chemical_formula_weight         446.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                102.701(7)
_cell_angle_beta                 100.959(6)
_cell_angle_gamma                97.914(5)
_cell_formula_units_Z            4
_cell_length_a                   8.2925(4)
_cell_length_b                   16.1905(12)
_cell_length_c                   18.3113(17)
_cell_measurement_reflns_used    4361
_cell_measurement_temperature    296.54(10)
_cell_measurement_theta_max      23.1830
_cell_measurement_theta_min      3.2940
_cell_volume                     2312.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      296.54(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8811
_diffrn_measurement_details
;
  1 omega  -92.00  -59.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000 -120.0000 22

  2 omega  -86.00  -56.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000 -150.0000 20

  3 omega  -20.00   22.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000    0.0000 28

  4 omega   -4.00   23.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000   30.0000 18

  5 omega   -8.00   68.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  120.0000 51

  6 omega  -55.00   89.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000  120.0000 96

  7 omega   72.00  105.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000  -30.0000 22

  8 omega   25.00   58.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   60.0000 22

  9 omega  -47.00   34.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075    0.0000   30.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0365690000
_diffrn_orient_matrix_UB_12      0.0264578000
_diffrn_orient_matrix_UB_13      -0.0209381000
_diffrn_orient_matrix_UB_21      0.0409544000
_diffrn_orient_matrix_UB_22      0.0307627000
_diffrn_orient_matrix_UB_23      0.0349209000
_diffrn_orient_matrix_UB_31      0.0696583000
_diffrn_orient_matrix_UB_32      -0.0210669000
_diffrn_orient_matrix_UB_33      0.0023040000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19030
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         9099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0614
_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/[\s^2^(Fo^2^)+(0.0489P)^2^+0.6951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                5373
_reflns_number_total             9099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05090h2.cif
_cod_data_source_block           yanzhfei0515
_cod_database_code               7115862
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C18(H18A,H18B), C32(H32A,H32B), C33(H33A,H33B),
 C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C21(H21),
 C22(H22), C24(H24), C25(H25), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
  C47(H47), C48(H48), C50(H50), C51(H51)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C52(H52A,H52B,H52C)
;