#------------------------------------------------------------------------------
#$Date: 2022-10-29 13:58:08 +0300 (Sat, 29 Oct 2022) $
#$Revision: 278872 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158964.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158964
loop_
_publ_author_name
'Natarajan, Nithya'
'Jayabal, Ezhilan'
'Rengarajan, Venkatesan'
'Gnanasambandam, Vasuki'
_publ_section_title
;
 Multicomponent synthesis of pyrrolo[2,1-a]isoindolylidene-malononitrile
 (PIYM) fluorophores and their photophysical properties
;
_journal_name_full               'Organic & 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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491   57.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -33.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -57.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -37.00   23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -57.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   54.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega    4.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
  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       'ω 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/[σ²(Fo²)+(0.0577P)²+0.9465P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3208(6) 0.60297(15) 0.32404(16) 0.0310(5) Uani 1 1 d . . . . .
C9 C 0.4508(6) 0.62159(16) 0.23513(16) 0.0311(5) Uani 1 1 d . . . . .
N2 N 0.3375(6) 0.51801(14) 0.33648(15) 0.0387(6) Uani 1 1 d . . . . .
H2 H 0.276561 0.492984 0.384954 0.046 Uiso 1 1 calc R U . . .
C5 C 0.6700(8) 0.5404(2) 0.11183(18) 0.0418(7) Uani 1 1 d . . . . .
H5 H 0.731010 0.488265 0.086540 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0890(7) 0.62788(17) 0.47050(18) 0.0388(6) Uani 1 1 d . . . . .
C6 C 0.7068(8) 0.6170(2) 0.0656(2) 0.0482(7) Uani 1 1 d . . . . .
H6 H 0.792213 0.616333 0.008249 0.058 Uiso 1 1 calc R U . . .
N12 N 0.0015(8) 0.60027(17) 0.53728(18) 0.0562(8) Uani 1 1 d . . . . .
C3 C 0.4683(7) 0.47124(17) 0.26054(18) 0.0380(6) Uani 1 1 d . . . . .
H3A H 0.298578 0.431709 0.231852 0.046 Uiso 1 1 calc R U . . .
H3B H 0.675102 0.439574 0.280797 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5400(7) 0.54318(16) 0.19676(17) 0.0344(6) Uani 1 1 d . . . . .
C13 C 0.1602(8) 0.74930(18) 0.37034(18) 0.0406(6) Uani 1 1 d . . . . .
C8 C 0.4894(7) 0.69860(18) 0.18844(19) 0.0398(6) Uani 1 1 d . . . . .
H8 H 0.430571 0.751010 0.213562 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6183(8) 0.6948(2) 0.1034(2) 0.0472(7) Uani 1 1 d . . . . .
H7 H 0.645920 0.745502 0.070908 0.057 Uiso 1 1 calc R U . . .
N14 N 0.1232(9) 0.82161(17) 0.3578(2) 0.0630(9) Uani 1 1 d . . . . .
C10 C 0.1976(7) 0.65972(16) 0.38713(17) 0.0346(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C9 107.4(2) . . ?
N2 C1 C10 123.5(2) . . ?
C10 C1 C9 129.1(2) . . ?
C4 C9 C1 107.7(2) . . ?
C8 C9 C1 131.7(2) . . ?
C8 C9 C4 120.6(2) . . ?
C1 N2 H2 123.0 . . ?
C1 N2 C3 113.9(2) . . ?
C3 N2 H2 123.0 . . ?
C6 C5 H5 120.8 . . ?
C6 C5 C4 118.3(3) . . ?
C4 C5 H5 120.8 . . ?
N12 C11 C10 178.5(3) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
N2 C3 H3A 111.4 . . ?
N2 C3 H3B 111.4 . . ?
N2 C3 C4 101.6(2) . . ?
H3A C3 H3B 109.3 . . ?
C4 C3 H3A 111.4 . . ?
C4 C3 H3B 111.4 . . ?
C9 C4 C3 109.4(2) . . ?
C5 C4 C9 120.9(2) . . ?
C5 C4 C3 129.8(2) . . ?
N14 C13 C10 178.4(3) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 C9 117.9(3) . . ?
C7 C8 H8 121.1 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C1 C10 C11 119.9(2) . . ?
C1 C10 C13 122.9(2) . . ?
C11 C10 C13 117.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.466(3) . ?
C1 N2 1.331(3) . ?
C1 C10 1.393(3) . ?
C9 C4 1.397(3) . ?
C9 C8 1.391(3) . ?
N2 H2 0.8600 . ?
N2 C3 1.457(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C5 C4 1.384(4) . ?
C11 N12 1.146(4) . ?
C11 C10 1.415(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.497(4) . ?
C13 N14 1.144(4) . ?
C13 C10 1.417(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(4) . ?
C7 H7 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C9 C4 C5 179.6(2) . . . . ?
C1 C9 C4 C3 0.1(3) . . . . ?
C1 C9 C8 C7 -179.2(3) . . . . ?
C1 N2 C3 C4 1.0(3) . . . . ?
C9 C1 N2 C3 -1.0(3) . . . . ?
C9 C1 C10 C11 -178.9(3) . . . . ?
C9 C1 C10 C13 4.0(4) . . . . ?
C9 C8 C7 C6 -0.1(5) . . . . ?
N2 C1 C9 C4 0.5(3) . . . . ?
N2 C1 C9 C8 179.8(3) . . . . ?
N2 C1 C10 C11 1.4(4) . . . . ?
N2 C1 C10 C13 -175.7(3) . . . . ?
N2 C3 C4 C9 -0.7(3) . . . . ?
N2 C3 C4 C5 179.9(3) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C5 C4 C9 -0.5(4) . . . . ?
C6 C5 C4 C3 178.9(3) . . . . ?
C4 C9 C8 C7 0.0(4) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C8 C9 C4 C5 0.3(4) . . . . ?
C8 C9 C4 C3 -179.2(2) . . . . ?
C10 C1 C9 C4 -179.2(3) . . . . ?
C10 C1 C9 C8 0.0(5) . . . . ?
C10 C1 N2 C3 178.8(2) . . . . ?
