Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines.
Mai, Shaoyu; Luo, Yixin; Huang, Xianyun; Shu, Zhenghao; Li, Bingnan; Lan, Yu; Song, Qiuling; Chemical communications (Cambridge, England) 54 (2018) 10240–10243; doi:10.1039/c8cc05390a

data_7125330
_publ_section_title
;
 Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10240
_journal_page_last               10243
_journal_paper_doi               10.1039/c8cc05390a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H21 F N2 O2'
_chemical_formula_sum            'C19 H21 F N2 O2'
_chemical_formula_weight         328.39
_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_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1zqrv9
_audit_creation_date             2018-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2018-04-24 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.739(11)
_cell_angle_beta                 99.147(11)
_cell_angle_gamma                106.484(12)
_cell_formula_units_Z            2
_cell_length_a                   6.3592(9)
_cell_length_b                   9.7262(14)
_cell_length_c                   15.058(2)
_cell_measurement_reflns_used    835
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.5110
_cell_measurement_theta_min      3.6810
_cell_volume                     877.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -7.00  79.00   1.00    8.50    --   15.49  77.00 -30.00   86
  2  \w     22.00  67.00   1.00    8.50    --   15.49  77.00-180.00   45
  3  \w     -3.00  44.00   1.00    8.50    --  -16.12  77.00   0.00   47
  4  \w    -11.00  79.00   1.00    8.50    --   15.49  77.00 120.00   90
  5  \w    -32.00  -6.00   1.00    8.50    --  -16.12  77.00   0.00   26
  6  \w    -37.00  46.00   1.00    8.50    --  -16.12  77.00-120.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0144253000
_diffrn_orient_matrix_UB_12      -0.0326489000
_diffrn_orient_matrix_UB_13      0.0406135000
_diffrn_orient_matrix_UB_21      -0.0475320000
_diffrn_orient_matrix_UB_22      -0.0683970000
_diffrn_orient_matrix_UB_23      -0.0251898000
_diffrn_orient_matrix_UB_31      0.1073156000
_diffrn_orient_matrix_UB_32      -0.0098047000
_diffrn_orient_matrix_UB_33      0.0038186000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7221
_diffrn_reflns_theta_full        24.9991
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.35
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2428
_exptl_crystal_description       block
_exptl_crystal_F_000             348.1823
_refine_diff_density_max         0.3768
_refine_diff_density_min         -0.3212
_refine_diff_density_rms         0.0871
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.0830
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0409
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0734P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.2011
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1559
_reflns_number_total             3088
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc05390a2.cif
_cod_data_source_block           exp_5355
_cod_original_cell_volume        877.4(2)
_cod_database_code               7125330
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G)
2.c Idealised Me refined as rotating group:
 C00K(H00a,H00c,H00d), C00L(H00h,H00i,H00k), C00M(H00l,H00m,H00n), C00N(H00o,
 H00p,H00q), C00O(H00r,H00s,H00t)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.379
_oxdiff_exptl_absorpt_empirical_full_min 0.577