Acid/base-controlled chemodivergent synthesis of two differently functionalized tetrahydroimidazo[1,2-a]pyridines
Guo, Wei-Si; Xin, Xing; Zhao, Ke-Long; Wen, Li-Rong; Li, Ming; RSC Adv.  (2015) –; doi:10.1039/C5RA13395E

data_7221783
_publ_section_title
;
 Acid/base-controlled chemodivergent synthesis of two differently
 functionalized tetrahydroimidazo[1,2-a]pyridines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA13395E
_journal_year                    2015
_chemical_formula_moiety         '2(C33 H24 Cl3 N3 O S), C2 H6 O'
_chemical_formula_sum            'C68 H54 Cl6 N6 O3 S2'
_chemical_formula_weight         1279.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-05-16 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                101.20(3)
_cell_angle_beta                 95.65(3)
_cell_angle_gamma                94.92(3)
_cell_formula_units_Z            2
_cell_length_a                   10.055(2)
_cell_length_b                   17.628(3)
_cell_length_c                   18.524(4)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4839
_cell_measurement_theta_min      1.1284
_cell_volume                     3186.6(12)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0127
_diffrn_orient_matrix_UB_12      0.0989
_diffrn_orient_matrix_UB_13      -0.0131
_diffrn_orient_matrix_UB_21      0.0265
_diffrn_orient_matrix_UB_22      0.0029
_diffrn_orient_matrix_UB_23      -0.0517
_diffrn_orient_matrix_UB_31      -0.0429
_diffrn_orient_matrix_UB_32      -0.0035
_diffrn_orient_matrix_UB_33      -0.0350
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35627
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.769
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     815
_refine_ls_number_reflns         11442
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0993
_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^)+(0.1254P)^2^+8.4848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2640
_refine_ls_wR_factor_ref         0.2716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10582
_reflns_number_total             11442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra13395e2.cif
_cod_data_source_block           mx3038_sq
_cod_original_cell_volume        3186.6(11)
_cod_database_code               7221783
_shelxl_version_number           2013-4
_diffrn_number_total             14573
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C29B-C28A = C30B-C29B = C30A-C29A = C29A-C28A = C33B-C32B = C33A-C32A = C33A-
 C28A = C33B-C28A = C32B-C31A = C32A-C31A = C31A-C30B = C31A-C30A
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C29A \\sim C29B \\sim C33B \\sim C33A \\sim C32A \\sim C32B \\sim C30B \\sim
C30A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(Cl3A) \\sim Ueq, Uanis(Cl3B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C30A) \\sim Ueq, Uanis(C30B) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C29B) \\sim Ueq, Uanis(C33B) \\sim Ueq, Uanis(C33A) \\sim Ueq,
Uanis(C32A) \\sim Ueq, Uanis(C32B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H8A)=Sof(Cl3B)=1-FVAR(1)
 Sof(H10A)=Sof(Cl3A)=FVAR(1)
 Sof(H31B)=Sof(C30B)=Sof(H30B)=Sof(C29B)=Sof(H29B)=Sof(C32B)=Sof(H32B)=
 Sof(C33B)=Sof(H33B)=1-FVAR(2)
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=
 Sof(C33A)=Sof(H33A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1B), C1A(H1AA)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19C,H19D), C20(H20C,H20D), C19A(H19A,H19B), C20A(H20A,H20B), C35(H35A,
 H35B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), N1A(H1A), N3A(H3A), C7A(H7A), C8A(H8A),
 C9A(H9A), C10A(H10A), C11A(H11A), C15A(H15A), C16A(H16A), C18A(H18A),
 C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A), C29A(H29A),
 C30A(H30A), C31A(H31A), C31A(H31B), C32A(H32A), C33A(H33A), C30B(H30B),
 C29B(H29B), C32B(H32B), C33B(H33B)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              73411
_shelx_fab_checksum              98182