Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes.
Das, Amrita; Ghosh, Indrajit; König, Burkhard; Chemical communications (Cambridge, England) 52 (2016) 8695–8698; doi:10.1039/c6cc04366f

data_7124751
_publ_section_title
;
 Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light
 mediated one- and twofold annulation of N-arylpyrroles with arylalkynes.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8695
_journal_page_last               8698
_journal_paper_doi               10.1039/c6cc04366f
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(C20 H15 N O)'
_chemical_formula_sum            'C40 H30 N2 O2'
_chemical_formula_weight         570.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-03
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-05-24 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                64.011(4)
_cell_angle_beta                 79.684(3)
_cell_angle_gamma                83.373(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2874(3)
_cell_length_b                   14.4206(5)
_cell_length_c                   15.0229(6)
_cell_measurement_reflns_used    11039
_cell_measurement_temperature    123.0(3)
_cell_measurement_theta_max      73.8360
_cell_measurement_theta_min      3.2880
_cell_volume                     1394.93(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (Rigaku OD, 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_environment      N~2~
_diffrn_ambient_temperature      123.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1818
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_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    -49.00  29.00   0.50    6.00    --  -43.14  37.00-180.00  156
  2  \w   -122.00  -4.00   0.50    6.00    --  -43.14 -15.00  -3.00  236
  3  \w     34.00 130.00   0.50    6.00    --   43.14-178.00  60.00  192
  4  \w     31.00  91.00   0.50   21.00    --  104.50 -30.00 120.00  120
  5  \w     26.00 144.00   0.50   21.00    --  104.50 -15.00 -60.00  236
  6  \w     30.00 136.00   0.50   21.00    --  104.50 -77.00 120.00  212
  7  \w     31.00  91.00   0.50   21.00    --  104.50 -30.00-180.00  120
  8  \w     31.00  91.00   0.50   21.00    --  104.50 -30.00-120.00  120
  9  \w     30.00 136.00   0.50   21.00    --  104.50 -77.00 -30.00  212
 10  \w     31.00 121.00   0.50   21.00    --  104.50-125.00 -30.00  180
 11  \w     31.00  91.00   0.50   21.00    --  104.50 -30.00  60.00  120
 12  \w   -117.00 -12.00   0.50    6.00    --  -43.14 -77.00-150.00  210
 13  \w   -113.00 -18.00   0.50    6.00    --  -43.14 -57.00 -60.00  190
 14  \w     18.00 113.00   0.50    6.00    --   43.14  57.00 120.00  190
 15  \w     73.00 178.00   0.50   21.00    --  104.50  77.00-180.00  210
 16  \w     78.00 178.00   0.50   21.00    --  104.50  30.00 120.00  200
 17  \w     78.00 174.00   0.50   21.00    --  104.50  61.00 -90.00  192
 18  \w     80.00 175.00   0.50   21.00    --  104.50  45.00 150.00  190
 19  \w     73.00 178.00   0.50   21.00    --  104.50  77.00  30.00  210
 20  \w     78.00 178.00   0.50   21.00    --  104.50  30.00   0.00  200
 21  \w   -124.00 -79.00   0.50    6.00    --  -43.14 -99.00 -90.00   90
 22  \w     12.00 117.00   0.50    6.00    --   43.14  77.00-180.00  210
 23  \w     12.00 117.00   0.50    6.00    --   43.14  77.00   0.00  210
 24  \w     80.00 105.00   0.50   21.00    --  104.50  45.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1261715000
_diffrn_orient_matrix_UB_12      -0.0766146000
_diffrn_orient_matrix_UB_13      -0.0035859000
_diffrn_orient_matrix_UB_21      0.1741591000
_diffrn_orient_matrix_UB_22      -0.0613010000
_diffrn_orient_matrix_UB_23      -0.0236544000
_diffrn_orient_matrix_UB_31      0.0008773000
_diffrn_orient_matrix_UB_32      -0.0672464000
_diffrn_orient_matrix_UB_33      0.1127738000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19204
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.897
_diffrn_reflns_theta_min         3.307
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.37b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0547
_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^)+(0.1145P)^2^+0.3763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4836
_reflns_number_total             5457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04366f2.cif
_cod_data_source_block           o095_w
_cod_original_cell_volume        1394.94(10)
_cod_database_code               7124751
_chemical_oxdiff_formula         'C20 H24 N O'
_chemical_oxdiff_usercomment     Koenig_Das
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C5(H5), C4(H4), C20(H20), C14(H14), C10(H10), C9(H9),
 C25(H25), C24(H24), C29(H29), C34(H34), C33(H33), C19(H19), C40(H40), C32(H32),
  C11(H11), C39(H39), C16(H16), C36(H36), C18(H18), C37(H37), C17(H17), C38(H38)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              71495
_shelx_hkl_checksum              41273
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-26
_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 2.842
_oxdiff_exptl_absorpt_empirical_full_min 0.508