#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:41:06 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281573 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/90/7159062.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_7159062
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         'C18 H12 N2 O3'
_chemical_formula_sum            'C18 H12 N2 O3'
_chemical_formula_weight         304.11
_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-2018/3
_audit_update_record
;
2022-06-28 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.947(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9737(17)
_cell_length_b                   7.6375(12)
_cell_length_c                   17.770(3)
_cell_measurement_reflns_used    8831
_cell_measurement_temperature    164(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.45
_cell_volume                     1451.5(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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      164(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0413
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.827
_diffrn_reflns_theta_min         2.915
_diffrn_source                   Mo
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       prism
_exptl_crystal_F_000             632.0
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0555
_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/[σ²(Fo²)+(0.1000P)²+0.8979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2389
_reflns_number_total             2800
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01725c2.cif
_cod_data_source_block           1831RKM_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159061--7159062.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159062
_shelx_shelxl_version_number     2018/3
_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 0.51267(14) 0.6742(2) 0.64009(9) 0.0505(4) Uani 1 1 d . . . . .
O2 O 0.89808(15) 0.4692(3) 0.75937(9) 0.0555(5) Uani 1 1 d . . . . .
O3 O 0.86568(16) 0.6578(3) 0.40335(9) 0.0581(5) Uani 1 1 d . . . . .
N1 N 0.71828(16) 0.5837(3) 0.68083(10) 0.0418(4) Uani 1 1 d . . . . .
C2 C 0.7075(2) 0.5085(3) 0.80423(12) 0.0419(5) Uani 1 1 d . . . . .
C12 C 0.7589(2) 0.6069(3) 0.61025(12) 0.0402(5) Uani 1 1 d . . . . .
C11 C 0.7911(2) 0.5149(3) 0.74864(12) 0.0419(5) Uani 1 1 d . . . . .
C10 C 0.59653(19) 0.6166(3) 0.68909(12) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.59326(19) 0.5678(3) 0.77091(12) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.7893(2) 0.3833(4) 0.94007(13) 0.0667(7) Uani 1 1 d . . . . .
C15 C 0.8360(2) 0.6458(3) 0.47368(12) 0.0435(5) Uani 1 1 d . . . . .
C1 C 0.7521(2) 0.4388(3) 0.88006(14) 0.0479(6) Uani 1 1 d . . . . .
C4 C 0.4822(2) 0.5829(3) 0.80304(13) 0.0428(5) Uani 1 1 d . . . . .
C13 C 0.8692(2) 0.6933(3) 0.60984(13) 0.0455(5) Uani 1 1 d . . . . .
H13 H 0.918307 0.739469 0.656535 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6869(2) 0.5402(3) 0.54264(13) 0.0461(5) Uani 1 1 d . . . . .
H17 H 0.610826 0.481177 0.542975 0.055 Uiso 1 1 calc R U . . .
C14 C 0.9084(2) 0.7127(3) 0.54192(13) 0.0460(5) Uani 1 1 d . . . . .
H14 H 0.984578 0.771501 0.541714 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7259(2) 0.5594(3) 0.47469(13) 0.0485(6) Uani 1 1 d . . . . .
H16 H 0.676622 0.512889 0.428127 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3628(2) 0.5596(3) 0.75651(15) 0.0535(6) Uani 1 1 d . . . . .
H5 H 0.352277 0.541856 0.702520 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4950(2) 0.6116(3) 0.88196(14) 0.0530(6) Uani 1 1 d . . . . .
H9 H 0.575675 0.628940 0.914238 0.064 Uiso 1 1 calc R U . . .
C18 C 0.9849(2) 0.7290(4) 0.40074(15) 0.0575(7) Uani 1 1 d . . . . .
H18A H 0.988698 0.851832 0.417030 0.086 Uiso 1 1 calc R U . . .
H18B H 0.997239 0.721476 0.347890 0.086 Uiso 1 1 calc R U . . .
H18C H 1.050682 0.662511 0.435495 0.086 Uiso 1 1 calc R U . . .
C8 C 0.3911(3) 0.6148(4) 0.91308(17) 0.0658(8) Uani 1 1 d . . . . .
H8 H 0.400363 0.634877 0.966829 0.079 Uiso 1 1 calc R U . . .
C7 C 0.2741(3) 0.5892(4) 0.8671(2) 0.0703(8) Uani 1 1 d . . . . .
H7 H 0.202868 0.590120 0.889264 0.084 Uiso 1 1 calc R U . . .
C6 C 0.2598(2) 0.5624(4) 0.78940(19) 0.0673(8) Uani 1 1 d . . . . .
H6 H 0.178580 0.545547 0.757816 0.081 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
C15 O3 C18 117.69(18) . . ?
C11 N1 C10 110.71(18) . . ?
C11 N1 C12 125.03(18) . . ?
C10 N1 C12 124.13(17) . . ?
C3 C2 C1 129.2(2) . . ?
C3 C2 C11 110.46(19) . . ?
C1 C2 C11 120.31(19) . . ?
C13 C12 C17 120.3(2) . . ?
C13 C12 N1 120.60(19) . . ?
C17 C12 N1 119.14(19) . . ?
O2 C11 N1 126.9(2) . . ?
O2 C11 C2 127.7(2) . . ?
N1 C11 C2 105.46(18) . . ?
O1 C10 N1 125.8(2) . . ?
O1 C10 C3 127.6(2) . . ?
N1 C10 C3 106.63(17) . . ?
C2 C3 C4 129.3(2) . . ?
C2 C3 C10 106.71(19) . . ?
C4 C3 C10 123.97(19) . . ?
O3 C15 C16 115.7(2) . . ?
O3 C15 C14 124.6(2) . . ?
C16 C15 C14 119.7(2) . . ?
N2 C1 C2 179.0(3) . . ?
C9 C4 C5 119.0(2) . . ?
C9 C4 C3 120.0(2) . . ?
C5 C4 C3 120.9(2) . . ?
C12 C13 C14 120.2(2) . . ?
C16 C17 C12 119.7(2) . . ?
C13 C14 C15 119.7(2) . . ?
C17 C16 C15 120.5(2) . . ?
C6 C5 C4 119.7(3) . . ?
C8 C9 C4 120.1(3) . . ?
C7 C8 C9 120.5(3) . . ?
C8 C7 C6 120.1(3) . . ?
C7 C6 C5 120.6(3) . . ?
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 C10 1.200(3) . ?
O2 C11 1.198(3) . ?
O3 C15 1.363(3) . ?
O3 C18 1.427(3) . ?
N1 C11 1.391(3) . ?
N1 C10 1.399(3) . ?
N1 C12 1.433(3) . ?
C2 C3 1.339(3) . ?
C2 C1 1.429(3) . ?
C2 C11 1.492(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.379(3) . ?
C10 C3 1.509(3) . ?
C3 C4 1.461(3) . ?
N2 C1 1.135(3) . ?
C15 C16 1.380(3) . ?
C15 C14 1.390(3) . ?
C4 C9 1.395(3) . ?
C4 C5 1.395(3) . ?
C13 C14 1.377(3) . ?
C17 C16 1.376(3) . ?
C5 C6 1.384(4) . ?
C9 C8 1.375(4) . ?
C8 C7 1.373(5) . ?
C7 C6 1.371(5) . ?
