Access to 6-hydroxy indolizines and related imidazo[1,5-a]pyridines through the SN2 substitution/condensation/tautomerization cascade process
Duan, Guiyun; Liu, Hao; Zhang, Liqing; Yuan, Chunhao; Li, Yongchao; Ge, Yanqing; RSC Advances 11 (2021) 25624–25627; doi:10.1039/D1RA04425G

data_7243268
_publ_section_title
;
 Access to 6-hydroxy indolizines and related imidazo[1,5-a]pyridines
 through the SN2 substitution/condensation/tautomerization cascade process
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              25624
_journal_page_last               25627
_journal_paper_doi               10.1039/D1RA04425G
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         '0.5(C26 H26 N2 O10)'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-04 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1584(2)
_cell_length_b                   6.6612(2)
_cell_length_c                   18.5993(5)
_cell_measurement_reflns_used    8438
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      4.32
_cell_volume                     1258.56(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10576
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.960
_diffrn_reflns_theta_min         4.314
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2155 before and 0.0908 after correction. The Ratio of minimum to maximum transmission is 0.5727. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0737P)^2^+0.5268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1144
_reflns_number_total             1306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra04425g2.cif
_cod_data_source_block           2103191533
_cod_database_code               7243268
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.960
_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. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H12A(0.5) H12B(0.5) H13B(0.5)
 H13C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Me refined with riding coordinates:
 C13(H13A,H13B,H13C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C8(H8)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              23993
_olex2_submission_special_instructions 'No special instructions were received'