When Indolizine Meets Quinoline: Diversity-Oriented Synthesis of New Polyheterocycles and Their Optical Properties.
Park, Sujin; Kwon, Dah In; Lee, Jeeyeon; Kim, Ikyon; ACS combinatorial science 17 (2015) 459–469; doi:10.1021/acscombsci.5b00031

data_4513559
_publ_section_title
;
 When Indolizine Meets Quinoline: Diversity-Oriented Synthesis of New
 Polyheterocycles and Their Optical Properties.
;
_journal_issue                   8
_journal_name_full               'ACS combinatorial science'
_journal_page_first              459
_journal_page_last               469
_journal_paper_doi               10.1021/acscombsci.5b00031
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H13 Br N2'
_chemical_formula_sum            'C21 H13 Br N2'
_chemical_formula_weight         373.24
_chemical_name_systematic        6-(4-Bromophenyl)indolizino[3,2-c]quinoline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1385(4)
_cell_length_b                   17.8868(19)
_cell_length_c                   20.726(3)
_cell_measurement_reflns_used    7993
_cell_measurement_temperature    171
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      2.47
_cell_volume                     1534.2(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      171.0
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10462
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        72.343
_diffrn_reflns_theta_max         72.343
_diffrn_reflns_theta_min         3.264
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.661
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0803 after correction.
The Ratio of minimum to maximum transmission is 0.7395.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.258
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.235
_refine_ls_abs_structure_details
;
 Flack x determined using 715 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0951
_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^)+43.4206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2494
_refine_ls_wR_factor_ref         0.2696
_reflns_Friedel_coverage         0.584
_reflns_Friedel_fraction_full    0.801
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                2246
_reflns_number_total             2619
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co5b00031_si_002.cif
_cod_data_source_block           6-(4-Bromophenyl)indolizino[3,2-c]quinoline
_cod_database_code               4513559
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.039) H5(0.033) H6(0.046) H7(0.044) H8(0.049) H11(0.048)
 H12(0.05) H13(0.059) H14(0.044) H19(0.039) H20(0.034) H22(0.027) H23(0.032)
 Fixed X: H1(0.3104) H5(1.0278) H6(1.1205) H7(0.9221) H8(0.589) H11(0.1158)
 H12(0.0058) H13(0.1598) H14(0.4307) H19(1.0703) H20(1.2148) H22(0.7151)
 H23(0.5624)
 Fixed Y: H1(0.5516) H5(0.3951) H6(0.4969) H7(0.6167) H8(0.6301) H11(0.4858)
 H12(0.4196) H13(0.2944) H14(0.236) H19(0.2026) H20(0.1144) H22(0.2338)
 H23(0.3179)
 Fixed Z: H1(0.2196) H5(0.3762) H6(0.4426) H7(0.4154) H8(0.3273) H11(0.1178)
 H12(0.0236) H13(0.0141) H14(0.0974) H19(0.2552) H20(0.3341) H22(0.4683)
 H23(0.3888)
;
_shelx_res_checksum              48118
_shelx_hkl_checksum              95896
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'