Ammonium Acetate-Promoted One-Pot Tandem Aldol Condensation/Aza-Addition Reactions: Synthesis of 2,3,6,7-Tetrahydro-1<i>H</i>-pyrrolo[3,2-<i>c</i>]pyridin-4(5<i>H</i>)-ones.
Zhang, Zhiguo; Gao, Xiaolong; Wan, Yameng; Huang, Yuanyuan; Huang, Guoqing; Zhang, Guisheng; ACS omega 2 (2017) 6844–6851; doi:10.1021/acsomega.7b00626

data_4516888
_publ_section_title
;
 Ammonium Acetate-Promoted One-Pot Tandem Aldol Condensation/Aza-Addition
 Reactions: Synthesis of
 2,3,6,7-Tetrahydro-1<i>H</i>-pyrrolo[3,2-<i>c</i>]pyridin-4(5<i>H</i>)-ones.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              6844
_journal_page_last               6851
_journal_paper_doi               10.1021/acsomega.7b00626
_journal_volume                  2
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 Cl2 N2 O'
_chemical_formula_sum            'C26 H22 Cl2 N2 O'
_chemical_formula_weight         449.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1830(3)
_cell_length_b                   11.7285(3)
_cell_length_c                   16.6352(4)
_cell_measurement_reflns_used    3473
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.2240
_cell_measurement_theta_min      4.5970
_cell_volume                     2181.87(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 25

  2 omega -110.00  -83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -180.0000 27

  3 omega  -39.00   15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   60.0000 54

  4 omega -112.00  -65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -139.0000  -55.0000 47

  5 omega  -28.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -90.0000 55

  6 omega   31.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000 -150.0000 39

  7 omega   60.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 26

  8 omega   40.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 33

  9 omega   71.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 26

 10 omega  103.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 70

 11 omega  101.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 75

 12 omega  109.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 69

 13 omega   41.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 25

 14 omega  -30.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -60.0000 26

 15 omega  -43.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -30.0000 65

 16 omega  -11.00   15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 26

 17 omega  115.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  111.0000    0.0000 52

 18 omega   67.00  101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -50.0000  120.0000 34

 19 omega   51.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -25.0000 -150.0000 41

 20 omega   50.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -63.0000   30.0000 61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0325244000
_diffrn_orient_matrix_UB_12      -0.1190939000
_diffrn_orient_matrix_UB_13      -0.0322944000
_diffrn_orient_matrix_UB_21      -0.0639522000
_diffrn_orient_matrix_UB_22      0.0552046000
_diffrn_orient_matrix_UB_23      -0.0722248000
_diffrn_orient_matrix_UB_31      0.1176101000
_diffrn_orient_matrix_UB_32      -0.0029074000
_diffrn_orient_matrix_UB_33      -0.0481976000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7932
_diffrn_reflns_theta_full        67.01
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         4.61
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0512P)^2^+0.1520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                3621
_reflns_number_total             3885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00626_si_002.cif
_cod_data_source_block           20150123
_cod_original_cell_volume        2181.86(9)
_cod_database_code               4516888
_chemical_oxdiff_formula         C20H20N4O4Cl2
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18), C19(H19),
 C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'