Synthesis of 2-julolidin-imidazo[1,2-a]pyridines via Groebke–Blackburn–Bienaymé reaction and studies of optical properties
Basavanag, Unnamatla M. V.; Islas-Jácome, Alejandro; Rentería-Gómez, Angel; Conejo, Alaín S.; Kurva, Mahanandaiah; Jiménez-Halla, J. Oscar C.; Velusamy, Jayaramakrishnan; Ramos-Ortíz, Gabriel; Gámez-Montaño, Rocío; New J. Chem. 41 (2017) 3450–; doi:10.1039/C6NJ04044F

data_7056063
_publ_section_title
;
 Synthesis of 2-julolidin-imidazo[1,2-a]pyridines via
 Groebke--Blackburn--Bienaym\'e reaction and studies of optical properties
;
_journal_issue                   9
_journal_name_full               'New J. Chem.'
_journal_page_first              3450
_journal_paper_doi               10.1039/C6NJ04044F
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C29 H31 Br N4 O2'
_chemical_formula_sum            'C29 H31 Br N4 O2'
_chemical_formula_weight         547.49
_chemical_melting_point          411.15
_chemical_name_systematic
5-bromo-N-(3,4-dimethoxyphenethyl)-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)imidazo[1,2-a]pyridin-3-amine
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-04-13 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                104.98(3)
_cell_angle_beta                 103.14(3)
_cell_angle_gamma                109.24(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1099(18)
_cell_length_b                   11.433(2)
_cell_length_c                   13.749(3)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100
_cell_measurement_theta_max      34.673
_cell_measurement_theta_min      2.498
_cell_volume                     1227.0(7)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         34.902
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.711
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0614 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.8456.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         10357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.2204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0713
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8715
_reflns_number_total             10357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj04044f2.cif
_cod_data_source_block           x85006_0m
_cod_depositor_comments          'Adding full bibliography for 7056063.cif.'
_cod_original_cell_volume        1226.9(5)
_cod_database_code               7056063
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.821
_shelx_estimated_absorpt_t_min   0.533
_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.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C20(H20a,H20b), C21(H21a,
 H21b), C22(H22a,H22b), C24(H24a,H24b), C25(H25a,H25b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C16(H16), C18(H18), C27(H27), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C33(H33a,H33b,H33c)
;
_solvent_exptl_crystal_recrystallization_method
'AcOEt/Petroleum Ether (3/7, v/v)'