#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/86/7218651.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_7218651
loop_
_publ_author_name
'Patel, Bhisma K.'
'Gogoi, Anupal'
'Guin, Srimant'
'Rout, Saroj Kumar'
'Ganesh, Majji'
_publ_section_title
;
 A Cu-catalysed synthesis of substituted 3-methyleneisoindolin-1-one
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12782J
_journal_year                    2014
_chemical_formula_moiety         'C21 H14 Cl N O'
_chemical_formula_sum            'C21 H14 Cl N O'
_chemical_formula_weight         331.78
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.312(3)
_cell_angle_beta                 93.496(3)
_cell_angle_gamma                96.408(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6383(7)
_cell_length_b                   9.0793(8)
_cell_length_c                   12.1907(10)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.54
_cell_volume                     814.28(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10162
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2881
_reflns_number_total             4062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra12782j2.cif
_cod_data_source_block           ag-1
_cod_database_code               7218651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.35946(7) 0.67432(7) 0.57303(3) 0.07756(19) Uani 1 1 d .
C7 C 0.79478(17) 0.76594(14) 1.08507(11) 0.0386(3) Uani 1 1 d .
C6 C 0.51225(18) 0.78233(15) 1.14693(11) 0.0408(3) Uani 1 1 d .
C8 C 0.80799(18) 0.79391(15) 1.20905(11) 0.0409(3) Uani 1 1 d .
C5 C 0.64073(19) 0.80276(15) 1.24610(11) 0.0421(3) Uani 1 1 d .
C4 C 0.6124(2) 0.82449(19) 1.35957(13) 0.0551(4) Uani 1 1 d .
H4 H 0.4998 0.8316 1.3837 0.066 Uiso 1 1 calc R
C1 C 0.9539(2) 0.80461(18) 1.28583(13) 0.0512(4) Uani 1 1 d .
H1 H 1.0668 0.7980 1.2620 0.061 Uiso 1 1 calc R
C3 C 0.7575(3) 0.8351(2) 1.43541(13) 0.0645(5) Uani 1 1 d .
H3 H 0.7427 0.8490 1.5121 0.077 Uiso 1 1 calc R
C2 C 0.9249(2) 0.8254(2) 1.39875(13) 0.0624(4) Uani 1 1 d .
H2 H 1.0205 0.8332 1.4517 0.075 Uiso 1 1 calc R
O1 O 0.35287(13) 0.78350(12) 1.14320(9) 0.0520(3) Uani 1 1 d .
C16 C 0.53494(17) 0.74725(15) 0.94083(11) 0.0382(3) Uani 1 1 d .
C21 C 0.58819(18) 0.85704(15) 0.88376(12) 0.0427(3) Uani 1 1 d .
H21 H 0.6619 0.9450 0.9214 0.051 Uiso 1 1 calc R
C19 C 0.41931(19) 0.70605(18) 0.71693(12) 0.0478(3) Uani 1 1 d .
C17 C 0.41433(18) 0.62133(16) 0.88771(12) 0.0454(3) Uani 1 1 d .
H17 H 0.3730 0.5510 0.9279 0.054 Uiso 1 1 calc R
C9 C 0.92866(18) 0.74766(16) 1.02004(12) 0.0443(3) Uani 1 1 d .
H9 H 1.0404 0.7617 1.0585 0.053 Uiso 1 1 calc R
C20 C 0.5320(2) 0.83621(17) 0.77073(12) 0.0469(3) Uani 1 1 d .
H20 H 0.5694 0.9086 0.7313 0.056 Uiso 1 1 calc R
C10 C 0.92395(17) 0.70825(16) 0.89539(12) 0.0424(3) Uani 1 1 d .
C15 C 0.8383(2) 0.57020(17) 0.83119(13) 0.0496(3) Uani 1 1 d .
H15 H 0.7858 0.4988 0.8670 0.060 Uiso 1 1 calc R
C18 C 0.3556(2) 0.60048(17) 0.77479(13) 0.0505(4) Uani 1 1 d .
H18 H 0.2745 0.5166 0.7385 0.061 Uiso 1 1 calc R
C11 C 1.0077(2) 0.81052(18) 0.83930(14) 0.0522(4) Uani 1 1 d .
H11 H 1.0710 0.9018 0.8809 0.063 Uiso 1 1 calc R
C12 C 0.9972(2) 0.7770(2) 0.72264(14) 0.0598(4) Uani 1 1 d .
H12 H 1.0507 0.8471 0.6861 0.072 Uiso 1 1 calc R
C14 C 0.8301(2) 0.5375(2) 0.71446(14) 0.0596(4) Uani 1 1 d .
H14 H 0.7712 0.4446 0.6723 0.072 Uiso 1 1 calc R
C13 C 0.9083(2) 0.6410(2) 0.66013(14) 0.0617(4) Uani 1 1 d .
H13 H 0.9010 0.6190 0.5815 0.074 Uiso 1 1 calc R
N1 N 0.61042(14) 0.76054(12) 1.05343(9) 0.0396(3) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C9 C7 N1 129.57(12)
C9 C7 C8 125.94(12)
N1 C7 C8 104.48(11)
O1 C6 N1 125.08(12)
O1 C6 C5 129.17(13)
N1 C6 C5 105.75(12)
C5 C8 C1 120.40(13)
C5 C8 C7 109.23(11)
C1 C8 C7 130.31(14)
C8 C5 C4 121.91(13)
C8 C5 C6 108.56(12)
C4 C5 C6 129.52(14)
C3 C4 C5 117.51(15)
C2 C1 C8 117.46(15)
C4 C3 C2 120.82(15)
C1 C2 C3 121.89(15)
C21 C16 C17 120.30(12)
C21 C16 N1 119.61(11)
C17 C16 N1 120.03(12)
C16 C21 C20 120.01(13)
C18 C19 C20 121.51(13)
C18 C19 Cl1 119.44(12)
C20 C19 Cl1 119.04(11)
C18 C17 C16 119.92(13)
C7 C9 C10 128.95(13)
C21 C20 C19 119.07(13)
C15 C10 C11 118.30(13)
C15 C10 C9 121.43(13)
C11 C10 C9 120.27(13)
C14 C15 C10 120.61(14)
C19 C18 C17 118.94(13)
C12 C11 C10 120.46(14)
C13 C12 C11 120.45(15)
C13 C14 C15 120.52(15)
C12 C13 C14 119.59(15)
C6 N1 C16 122.98(11)
C6 N1 C7 111.99(11)
C16 N1 C7 124.84(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C19 1.7348(14)
C7 C9 1.333(2)
C7 N1 1.4296(17)
C7 C8 1.4690(18)
C6 O1 1.2169(17)
C6 N1 1.3907(17)
C6 C5 1.4731(19)
C8 C5 1.385(2)
C8 C1 1.3911(19)
C5 C4 1.386(2)
C4 C3 1.379(2)
C1 C2 1.381(2)
C3 C2 1.386(3)
C16 C21 1.3807(19)
C16 C17 1.3879(19)
C16 N1 1.4294(16)
C21 C20 1.3814(19)
C19 C18 1.379(2)
C19 C20 1.384(2)
C17 C18 1.385(2)
C9 C10 1.4759(19)
C10 C15 1.384(2)
C10 C11 1.397(2)
C15 C14 1.381(2)
C11 C12 1.379(2)
C12 C13 1.372(3)
C14 C13 1.374(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199434
