Multicomponent synthesis of pyrrolo[2,1-a]isoindolylidene-malononitrile (PIYM) fluorophores and their photophysical properties
Natarajan, Nithya; Jayabal, Ezhilan; Rengarajan, Venkatesan; Gnanasambandam, Vasuki; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01209J

data_7158964
_publ_section_title
;
 Multicomponent synthesis of pyrrolo[2,1-a]isoindolylidene-malononitrile
 (PIYM) fluorophores and their photophysical properties
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01209J
_journal_year                    2022
_chemical_formula_moiety         'C11 H7 N3'
_chemical_formula_sum            'C11 H7 N3'
_chemical_formula_weight         181.20
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-11-30 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.477(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9218(3)
_cell_length_b                   15.5165(11)
_cell_length_c                   14.5798(11)
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1462
_cell_measurement_theta_min      3.0928
_cell_volume                     883.17(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
;
  1 omega  -18.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491   57.0000 -150.0000 64

  2 omega  -25.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000 -180.0000 50

  3 omega   -2.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  -60.0000 90

  4 omega  -33.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -57.0000   30.0000 72

  5 omega  -37.00   23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -57.0000  120.0000 60

  6 omega   54.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  178.0000  -90.0000 26

  7 omega    4.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000   30.0000 56

  8 omega  -61.00   56.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491   19.0000    0.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0287830000
_diffrn_orient_matrix_UB_12      0.0049672000
_diffrn_orient_matrix_UB_13      -0.0484859000
_diffrn_orient_matrix_UB_21      -0.0222575000
_diffrn_orient_matrix_UB_22      -0.0451498000
_diffrn_orient_matrix_UB_23      -0.0049427000
_diffrn_orient_matrix_UB_31      -0.1780821000
_diffrn_orient_matrix_UB_32      0.0048520000
_diffrn_orient_matrix_UB_33      0.0037522000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9532
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.211
_diffrn_reflns_theta_min         3.099
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0744
_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^)+(0.0577P)^2^+0.9465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1787
_reflns_number_total             2161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01209j2.cif
_cod_data_source_block           gv-mn
_cod_original_cell_volume        883.18(11)
_cod_database_code               7158964
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H7 N3'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 297K, 0.72 0.40 0.20'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C8(H8), C7(H7)
;
_shelx_res_checksum              43298
_olex2_submission_special_instructions 'No special instructions were received'