Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.
Ni, Qijian; Song, Xiaoxiao; Xiong, Jiawen; Raabe, Gerhard; Enders, Dieter; Chemical communications (Cambridge, England) 51 (2014) 1263–1266; doi:10.1039/c4cc08594a

data_7116203
_publ_section_title
;
 Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via
 an NHC-catalyzed Mannich/lactamization domino reaction.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1263
_journal_page_last               1266
_journal_paper_doi               10.1039/c4cc08594a
_journal_volume                  51
_journal_year                    2014
_chemical_formula_sum            'C23 H17 Cl N2 O S'
_chemical_formula_weight         404.93
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_update_record
;
2014-10-16 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00000
_cell_angle_beta                 115.422(2)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            2
_cell_length_a                   13.6665(6)
_cell_length_b                   5.3783(2)
_cell_length_c                   14.1760(6)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.78
_cell_measurement_theta_min      3.45
_cell_volume                     941.08(7)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_detector       'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .02
_diffrn_reflns_av_sigmaI/netI    .023
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22918
_diffrn_reflns_theta_max         67.25
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    2.962
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.4529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate:hexane 1:3'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         .267
_refine_diff_density_min         -.199
_refine_ls_abs_structure_details 'Flack parameter'
_refine_ls_abs_structure_Flack   0.0579(146)
_refine_ls_extinction_coef       .00000
_refine_ls_goodness_of_fit_all   1.002
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .026
_refine_ls_R_factor_gt           .026
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
1/[2.5\s^2^(F)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .032
_refine_ls_wR_factor_ref         .032
_reflns_d_resolution_high        .836
_reflns_d_resolution_low         12.771
_reflns_Friedel_coverage         .796
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -16
_reflns_number_gt                3231
_reflns_number_total             3240
_reflns_threshold_expression     'I>  2.00 sig(I)'
_cod_data_source_file            c4cc08594a2.cif
_cod_data_source_block           gr0773
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     p_2y1
_cod_original_sg_symbol_H-M      P_1_21_1
_cod_original_formula_sum        'C23 H17 Cl1 N2 O1 S1'
_cod_database_code               7116203