#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/96/2239607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239607
loop_
_publ_author_name
'Abbassi, Bahar'
'Brumfield, Michela'
'Jones, Lloyd M.'
'Nesterov, Vladimir N.'
'Carr, Andrew J.'
_publ_section_title
;
 5-Cyano-1,3-phenylene diacetate
;
_journal_coeditor_code           CV5455
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o712
_journal_paper_doi               10.1107/S1600536814011374
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H9 N O4'
_chemical_formula_moiety         'C11 H9 N O4'
_chemical_formula_sum            'C11 H9 N O4'
_chemical_formula_weight         219.19
_chemical_name_systematic
;
5-Cyano-1,3-phenylene diacetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.1710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2293(5)
_cell_length_b                   21.1153(17)
_cell_length_c                   8.5989(7)
_cell_measurement_reflns_used    6321
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.77
_cell_volume                     1068.32(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω 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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14252
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.130
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.05P)²+0.2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2067
_reflns_number_total             2340
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5455sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239607
_cod_database_fobs_code          2239607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.44864(12) 0.62983(4) 0.67935(9) 0.0388(2) Uani d . 1 1
C C1 0.26158(17) 0.53192(5) 0.30796(13) 0.0347(2) Uani d . 1 1
N N1 -0.0537(2) 0.45024(6) 0.17554(15) 0.0578(3) Uani d . 1 1
O O2 0.11962(15) 0.68031(4) 0.55736(11) 0.0484(2) Uani d . 1 1
C C2 0.26753(17) 0.55886(5) 0.45661(13) 0.0345(2) Uani d . 1 1
H H2A 0.1601 0.5470 0.5083 0.041 Uiso calc R 1 1
O O3 0.73998(13) 0.60722(4) 0.23031(10) 0.0397(2) Uani d . 1 1
C C3 0.43337(17) 0.60332(5) 0.52755(13) 0.0331(2) Uani d . 1 1
O O4 0.67580(16) 0.71218(4) 0.23128(11) 0.0493(2) Uani d . 1 1
C C4 0.59239(17) 0.62130(5) 0.45604(13) 0.0349(2) Uani d . 1 1
H H4A 0.7062 0.6517 0.5071 0.042 Uiso calc R 1 1
C C5 0.58096(17) 0.59369(5) 0.30774(13) 0.0339(2) Uani d . 1 1
C C6 0.41844(18) 0.54912(5) 0.23152(14) 0.0355(2) Uani d . 1 1
H H6A 0.4137 0.5307 0.1297 0.043 Uiso calc R 1 1
C C7 0.27412(18) 0.66893(5) 0.67974(13) 0.0361(2) Uani d . 1 1
C C8 0.3085(2) 0.69393(6) 0.84782(15) 0.0490(3) Uani d . 1 1
H H8A 0.1718 0.7167 0.8487 0.073 Uiso calc R 1 1
H H8B 0.4387 0.7229 0.8795 0.073 Uiso calc R 1 1
H H8C 0.3377 0.6587 0.9261 0.073 Uiso calc R 1 1
C C9 0.77434(19) 0.66931(5) 0.19634(14) 0.0374(3) Uani d . 1 1
C C10 0.9438(2) 0.67242(6) 0.10879(19) 0.0531(3) Uani d . 1 1
H H10A 0.9422 0.7149 0.0623 0.080 Uiso calc R 1 1
H H10B 0.9055 0.6410 0.0199 0.080 Uiso calc R 1 1
H H10C 1.0956 0.6634 0.1864 0.080 Uiso calc R 1 1
C C11 0.0867(2) 0.48624(5) 0.23206(15) 0.0410(3) Uani d . 1 1
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
C7 O1 C3 115.80(8)
C2 C1 C6 121.12(10)
C2 C1 C11 118.61(9)
C6 C1 C11 120.26(10)
C3 C2 C1 118.37(9)
C3 C2 H2A 120.8
C1 C2 H2A 120.8
C9 O3 C5 118.81(8)
C4 C3 C2 122.18(10)
C4 C3 O1 117.94(9)
C2 C3 O1 119.84(9)
C3 C4 C5 117.91(10)
C3 C4 H4A 121.0
C5 C4 H4A 121.0
C6 C5 C4 122.22(9)
C6 C5 O3 116.03(9)
C4 C5 O3 121.68(9)
C5 C6 C1 118.20(10)
C5 C6 H6A 120.9
C1 C6 H6A 120.9
O2 C7 O1 122.08(10)
O2 C7 C8 127.04(11)
O1 C7 C8 110.88(10)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O4 C9 O3 122.96(10)
O4 C9 C10 127.40(11)
O3 C9 C10 109.62(9)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N1 C11 C1 178.16(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3661(13)
O1 C3 1.3944(12)
C1 C2 1.3884(15)
C1 C6 1.3930(15)
C1 C11 1.4409(15)
N1 C11 1.1402(15)
O2 C7 1.1943(14)
C2 C3 1.3809(15)
C2 H2A 0.9500
O3 C9 1.3752(13)
O3 C5 1.3926(12)
C3 C4 1.3797(14)
O4 C9 1.1865(13)
C4 C5 1.3826(15)
C4 H4A 0.9500
C5 C6 1.3800(15)
C6 H6A 0.9500
C7 C8 1.4866(16)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.4859(16)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4A O2 1_655 0.95 2.54 3.3495(14) 143
C10 H10A O2 4_675 0.98 2.48 3.3738(15) 151
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 24721096
