A route to access imidazol[1,5-a]indole-1,3-diones and pyrrolo[1,2-c]imidazole-1,3-diones.
Sreenivasa Rao, Ramana; Shajan, Femil Joseph; Reddy, D. Srinivasa; Organic & biomolecular chemistry 17 (2019) 8384–8390; doi:10.1039/c9ob01462d

data_7157042
_publ_section_title
;
 A route to access imidazol[1,5-a]indole-1,3-diones and
 pyrrolo[1,2-c]imidazole-1,3-diones.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8384
_journal_page_last               8390
_journal_paper_doi               10.1039/c9ob01462d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C12 H6 Cl2 N2 O2'
_chemical_formula_sum            'C12 H6 Cl2 N2 O2'
_chemical_formula_weight         281.09
_chemical_melting_point          471.5(5)
_chemical_name_systematic        RSR-4e
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-11 deposited with the CCDC.    2019-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4975(2)
_cell_length_b                   14.8593(4)
_cell_length_c                   7.2597(2)
_cell_measurement_reflns_used    7567
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.28
_cell_measurement_theta_min      2.41
_cell_volume                     1110.18(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24444
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.584
_diffrn_reflns_theta_min         2.407
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0218P)^2^+0.8753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3315
_reflns_number_total             4005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01462d2.cif
_cod_data_source_block           RSR
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '471-472' was changed to '471.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7157042.cif.
;
_cod_database_code               7157042
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              79302