Cyclization of lithiated pyridine and quinoline carboxamides: synthesis of partially saturated pyrrolopyridines and spirocyclic beta-lactams.
Clayden, Jonathan; Hamilton, Stuart D.; Mohammed, Rukhsana T.; Organic letters 7 (2005) 3673–3676; doi:10.1021/ol051214u

data_1506639
_publ_section_title
;
 Cyclization of lithiated pyridine and quinoline carboxamides: synthesis
 of partially saturated pyrrolopyridines and spirocyclic beta-lactams.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3673
_journal_page_last               3676
_journal_paper_doi               10.1021/ol051214u
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C19 H20 Cl2 N2 O3'
_chemical_formula_weight         395.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 111.413(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3969(17)
_cell_length_b                   7.2480(8)
_cell_length_c                   19.347(2)
_cell_measurement_reflns_used    3167
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.385
_cell_measurement_theta_min      3.0395
_cell_volume                     1879.5(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11422
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.8671
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0398
_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/[\s^2^(Fo^2^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                3230
_reflns_number_total             4410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051214usi20050524_062132.cif
_cod_data_source_block           s1343m
_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      P2(1)/c
_cod_database_code               1506639