Pyrrolo-imidazo[1,2-<i>a</i>]pyridine Scaffolds through a Sequential Coupling of <i>N</i>-Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application.
Zhang, Kena; El Bouakher, Abderrahman; Levaique, Helene; Bignon, Jerome; Retailleau, Pascal; Alami, Mouad; Hamze, Abdallah; The Journal of organic chemistry 84 (2019) 13807–13823; doi:10.1021/acs.joc.9b02018

data_4034533
_publ_section_title
;
 Pyrrolo-imidazo[1,2-<i>a</i>]pyridine Scaffolds through a Sequential
 Coupling of <i>N</i>-Tosylhydrazones with Imidazopyridines and Reductive
 Cadogan Annulation, Synthetic Scope, and Application.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13807
_journal_page_last               13823
_journal_paper_doi               10.1021/acs.joc.9b02018
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H19 N3 O3, C2 H6 O'
_chemical_formula_sum            'C23 H25 N3 O4'
_chemical_formula_weight         407.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.286(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0678(7)
_cell_length_b                   24.954(2)
_cell_length_c                   11.6047(10)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2
_cell_measurement_theta_min      3.5
_cell_volume                     2046.2(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku Rapid2 curved large area IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
scan:
	Number of images: 16
	           Slice: 20.0000 - 185.0000
	     Image width: 10.0000
	        Exp time: 1500.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 10
	           Slice: 20.0000 - 128.0000
	     Image width: 10.0000
	        Exp time: 1500.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 6
	           Slice: 122.0000 - 190.0000
	     Image width: 10.0000
	        Exp time: 1500.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 3
	           Slice: 110.0000 - 140.0000
	     Image width: 10.0000
	        Exp time: 1500.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000

;
_diffrn_measurement_device
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type
;
Rigaku MM007HF Spider
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  'OSMIC CMF optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.1156
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8889
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        63.015
_diffrn_reflns_theta_max         63.015
_diffrn_reflns_theta_min         3.542
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Reqab (Higashi-Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       'cracked needle'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1034P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.2241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1349
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02018_si_003.cif
_cod_data_source_block           ABE-4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034533
_shelx_res_checksum              25872
_shelx_hkl_checksum              15535