#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:41:06 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159061.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_7159061
loop_
_publ_author_name
'Sarkar, Prabhat'
'Saha, Pinaki'
'Ghosh, Prasanta'
'Mukhopadhyay, Chhanda'
_publ_section_title
;
 Metal-free, I₂-promoted direct synthesis of
 2-cyano-substituted maleimides via a unique
 3,3-dicyano-2-arylacrylic acid intermediate.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              789
_journal_page_last               796
_journal_paper_doi               10.1039/d2ob01725c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H14 N2 O3'
_chemical_formula_sum            'C19 H14 N2 O3'
_chemical_formula_weight         318.32
_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_method           SHELXL-2016/6
_audit_update_record
;
2022-06-23 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.77
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.321(2)
_cell_length_b                   6.8496(11)
_cell_length_c                   18.783(3)
_cell_measurement_reflns_used    8709
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.32
_cell_volume                     1602.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37763
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.988
_diffrn_reflns_theta_min         2.316
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.969
_exptl_transmission_factor_min   0.938
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0597
_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)+(0.1000P)²+0.5373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2396
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01725c2.cif
_cod_data_source_block           TRY1_a
_cod_depositor_comments
'Adding full bibliography for 7159061--7159062.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159061
_shelx_shelxl_version_number     2016/6
_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.
;
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
O1 O 0.53739(13) 1.1463(3) 0.73087(10) 0.0610(5) Uani 1 1 d . . . . .
O2 O 0.46412(13) 0.6364(3) 0.56565(9) 0.0606(5) Uani 1 1 d . . . . .
O3 O 0.07903(12) 1.2386(3) 0.46854(10) 0.0649(5) Uani 1 1 d . . . . .
N2 N 0.47534(13) 0.9159(2) 0.63507(10) 0.0438(5) Uani 1 1 d . . . . .
C8 C 0.62172(15) 0.7039(3) 0.67921(11) 0.0385(5) Uani 1 1 d . . . . .
C5 C 0.68707(16) 0.5328(3) 0.68096(12) 0.0396(5) Uani 1 1 d . . . . .
N1 N 0.79868(18) 0.9465(3) 0.84654(13) 0.0685(6) Uani 1 1 d . . . . .
C10 C 0.63922(16) 0.8579(3) 0.72667(12) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.51245(17) 0.7395(3) 0.61867(12) 0.0433(5) Uani 1 1 d . . . . .
C13 C 0.37337(16) 1.0007(3) 0.59109(12) 0.0431(5) Uani 1 1 d . . . . .
C12 C 0.54747(17) 0.9963(3) 0.70136(13) 0.0444(5) Uani 1 1 d . . . . .
C4 C 0.66594(17) 0.4109(3) 0.61794(13) 0.0471(5) Uani 1 1 d . . . . .
H4 H 0.607294 0.436435 0.574001 0.057 Uiso 1 1 calc R U . . .
C16 C 0.17876(16) 1.1657(3) 0.50797(13) 0.0481(6) Uani 1 1 d . . . . .
C11 C 0.72870(18) 0.9031(3) 0.79372(14) 0.0481(5) Uani 1 1 d . . . . .
C6 C 0.77464(18) 0.4871(3) 0.74610(13) 0.0514(6) Uani 1 1 d . . . . .
H6 H 0.789777 0.564231 0.789392 0.062 Uiso 1 1 calc R U . . .
C14 C 0.27931(18) 0.9027(3) 0.58355(14) 0.0506(6) Uani 1 1 d . . . . .
H14 H 0.281573 0.781907 0.606667 0.061 Uiso 1 1 calc R U . . .
C15 C 0.18269(17) 0.9857(4) 0.54159(14) 0.0531(6) Uani 1 1 d . . . . .
H15 H 0.119214 0.919885 0.535794 0.064 Uiso 1 1 calc R U . . .
C7 C 0.83874(19) 0.3296(4) 0.74706(15) 0.0565(6) Uani 1 1 d . . . . .
H7 H 0.896955 0.302513 0.791093 0.068 Uiso 1 1 calc R U . . .
C18 C 0.37001(17) 1.1778(3) 0.55693(14) 0.0530(6) Uani 1 1 d . . . . .
H18 H 0.433637 1.241879 0.561760 0.064 Uiso 1 1 calc R U . . .
C2 C 0.81898(19) 0.2102(4) 0.68429(15) 0.0570(6) Uani 1 1 d . . . . .
C3 C 0.7310(2) 0.2528(4) 0.61999(14) 0.0572(6) Uani 1 1 d . . . . .
H3 H 0.715474 0.173246 0.577303 0.069 Uiso 1 1 calc R U . . .
C17 C 0.27294(18) 1.2622(3) 0.51536(14) 0.0544(6) Uani 1 1 d . . . . .
H17 H 0.270901 1.383218 0.492452 0.065 Uiso 1 1 calc R U . . .
C19 C 0.0730(2) 1.4280(4) 0.4363(2) 0.0808(9) Uani 1 1 d . . . . .
H19A H 0.107451 1.520457 0.475830 0.121 Uiso 1 1 calc R U . . .
H19B H -0.000973 1.463813 0.411549 0.121 Uiso 1 1 calc R U . . .
H19C H 0.108296 1.427519 0.399774 0.121 Uiso 1 1 calc R U . . .
C1 C 0.8915(3) 0.0400(5) 0.6860(2) 0.0864(10) Uani 1 1 d . . . . .
H1A H 0.848924 -0.075217 0.668221 0.130 Uiso 1 1 calc R U . . .
H1B H 0.939993 0.019460 0.737242 0.130 Uiso 1 1 calc R U . . .
H1C H 0.931786 0.067258 0.653739 0.130 Uiso 1 1 calc R U . . .
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'
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
C16 O3 C19 117.5(2) . . ?
C9 N2 C12 111.00(18) . . ?
C9 N2 C13 124.40(18) . . ?
C12 N2 C13 124.55(18) . . ?
C10 C8 C5 130.91(19) . . ?
C10 C8 C9 105.36(18) . . ?
C5 C8 C9 123.73(18) . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 C8 121.68(19) . . ?
C6 C5 C8 120.61(19) . . ?
C8 C10 C11 130.4(2) . . ?
C8 C10 C12 111.01(18) . . ?
C11 C10 C12 118.61(19) . . ?
O2 C9 N2 124.7(2) . . ?
O2 C9 C8 128.0(2) . . ?
N2 C9 C8 107.35(17) . . ?
C18 C13 C14 120.3(2) . . ?
C18 C13 N2 119.70(18) . . ?
C14 C13 N2 120.0(2) . . ?
O1 C12 N2 126.9(2) . . ?
O1 C12 C10 127.9(2) . . ?
N2 C12 C10 105.25(18) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O3 C16 C15 116.6(2) . . ?
O3 C16 C17 123.6(2) . . ?
C15 C16 C17 119.8(2) . . ?
N1 C11 C10 177.3(3) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C6 C7 C2 121.7(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C13 C18 C17 120.4(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C7 C2 C3 117.8(2) . . ?
C7 C2 C1 120.9(3) . . ?
C3 C2 C1 121.3(3) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
O1 C12 1.197(3) . ?
O2 C9 1.204(3) . ?
O3 C16 1.366(3) . ?
O3 C19 1.421(3) . ?
N2 C9 1.381(3) . ?
N2 C12 1.389(3) . ?
N2 C13 1.438(3) . ?
C8 C10 1.347(3) . ?
C8 C5 1.453(3) . ?
C8 C9 1.516(3) . ?
C5 C4 1.393(3) . ?
C5 C6 1.394(3) . ?
N1 C11 1.134(3) . ?
C10 C11 1.428(3) . ?
C10 C12 1.485(3) . ?
C13 C18 1.366(3) . ?
C13 C14 1.384(3) . ?
C4 C3 1.379(3) . ?
C4 H4 0.9300 . ?
C16 C15 1.378(3) . ?
C16 C17 1.381(3) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C7 C2 1.381(4) . ?
C7 H7 0.9300 . ?
C18 C17 1.378(3) . ?
C18 H18 0.9300 . ?
C2 C3 1.383(3) . ?
C2 C1 1.507(3) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
