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_7124752
_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         'C20 H14 Cl N O'
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-25
_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                90
_cell_angle_beta                 108.390(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4245(3)
_cell_length_b                   7.25848(14)
_cell_length_c                   13.1153(3)
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.2070
_cell_measurement_theta_min      5.6670
_cell_volume                     1483.72(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41h (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41h (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41h (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      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.962
_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    -67.00  35.00   1.00    3.00    --  -40.71  37.00-150.00  102
  2  \w      2.00  98.00   1.00    3.00    --   40.71-125.00   0.00   96
  3  \w     32.00  77.00   1.00   11.00    --  106.98 -45.00 -90.00   45
  4  \w     23.00 109.00   1.00   11.00    --  106.98 -94.00 -60.00   86
  5  \w     77.00 158.00   1.00   11.00    --  106.98  61.00   0.00   81
  6  \w     32.00 121.00   1.00   11.00    --  106.98-125.00-120.00   89
  7  \w     18.00 158.00   1.00   11.00    --  106.98   0.00   0.00  140
  8  \w     11.00  36.00   1.00    3.00    --   40.71  57.00  90.00   25
  9  \w     11.00 115.00   1.00    3.00    --   40.71  57.00-150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0922111000
_diffrn_orient_matrix_UB_12      -0.0626352000
_diffrn_orient_matrix_UB_13      0.0606807000
_diffrn_orient_matrix_UB_21      0.0338413000
_diffrn_orient_matrix_UB_22      0.1920885000
_diffrn_orient_matrix_UB_23      -0.0163446000
_diffrn_orient_matrix_UB_31      -0.0110977000
_diffrn_orient_matrix_UB_32      0.0649938000
_diffrn_orient_matrix_UB_33      0.1066358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6017
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.307
_diffrn_reflns_theta_min         5.677
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41h (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0454P)^2^+0.3342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2544
_reflns_number_total             2870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04366f2.cif
_cod_data_source_block           p005
_cod_database_code               7124752
_chemical_oxdiff_formula         'C20 H14 Cl N O'
_chemical_oxdiff_usercomment     'Das_Koenig_AD P125'
_reflns_odcompleteness_completeness 99.07
_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:
 C16(H16), C7(H7), C4(H4), C10(H10), C19(H19), C11(H11), C14(H14), C18(H18),
 C17(H17), C13(H13), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              62368
_shelx_hkl_checksum              26291
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-21
_olex2_date_sample_submission    2016-01-14
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_submission_original_sample_id 'AD P 125'
_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.725