#------------------------------------------------------------------------------
#$Date: 2023-04-05 19:03:21 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312062.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_2312062
loop_
_publ_author_name
'Erzunov, Dmitry'
'Rassolova, Anastasia'
'Rumyantsev, Roman'
'Maizlish, Vladimir'
'Tikhomirova, Tatiana'
'Vashurin, Arthur'
_publ_section_title
;
 Crystal structures of 4-(2/3-meth-oxy-phen-oxy)phthalo-nitrile.
;
_journal_coeditor_code           YZ2027
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              172
_journal_page_last               176
_journal_paper_doi               10.1107/S2056989023000518
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C15 H10 N2 O2'
_chemical_formula_moiety         'C15 H10 N2 O2'
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25
_chemical_name_common
;
4-(3-Methoxyphenoxy)phthalonitrile
;
_chemical_name_systematic
;
4-(3-Methoxyphenoxy)benzene-1,2-dicarbonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                104.6380(10)
_cell_angle_beta                 95.0780(10)
_cell_angle_gamma                110.5700(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0609(3)
_cell_length_b                   8.4672(4)
_cell_length_c                   9.9999(4)
_cell_measurement_reflns_used    9781
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.70
_cell_volume                     606.31(4)
_computing_cell_refinement
;
SAINT (Bruker, 2003)
;
_computing_data_collection
;
APEX3 (Bruker, 2003)
;
_computing_data_reduction
;
SAINT (Bruker, 2003)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest (CMOS)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10029
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.146
_diffrn_source                   'microfocus tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0386
_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)+(0.0528P)²+0.2143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3040
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2027sup1.cif
_cod_data_source_block           m-C15H10N2O2
_cod_database_code               2312062
_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.
;
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.56496(10) 0.59440(10) 0.80203(7) 0.01795(16) Uani d 1 . .
O O2 0.87906(10) 0.47550(9) 1.17760(7) 0.01716(16) Uani d 1 . .
N N1 0.95411(13) 0.23336(15) 0.44743(10) 0.0277(2) Uani d 1 . .
N N2 0.46049(13) -0.06002(13) 0.21559(10) 0.0253(2) Uani d 1 . .
C C1 0.69339(13) 0.64698(13) 0.92463(10) 0.01494(18) Uani d 1 . .
C C2 0.72490(12) 0.52173(12) 0.97939(9) 0.01389(18) Uani d 1 . .
H H2A 0.668855 0.398795 0.929816 0.017 Uiso calc 1 . .
C C3 0.84135(13) 0.58336(12) 1.10919(9) 0.01423(18) Uani d 1 . .
C C4 0.92411(14) 0.76450(13) 1.18106(10) 0.01779(19) Uani d 1 . .
H H4A 1.004512 0.805311 1.269112 0.021 Uiso calc 1 . .
C C5 0.88827(14) 0.88403(13) 1.12324(11) 0.0203(2) Uani d 1 . .
H H5A 0.943632 1.007075 1.172592 0.024 Uiso calc 1 . .
C C6 0.77200(14) 0.82629(13) 0.99356(10) 0.0186(2) Uani d 1 . .
H H6A 0.747571 0.908341 0.953705 0.022 Uiso calc 1 . .
C C7 0.55405(13) 0.45928(12) 0.68822(9) 0.01418(18) Uani d 1 . .
C C8 0.70450(12) 0.42664(12) 0.65164(9) 0.01438(18) Uani d 1 . .
H H8A 0.820847 0.493469 0.709832 0.017 Uiso calc 1 . .
C C9 0.67994(12) 0.29370(12) 0.52775(9) 0.01387(18) Uani d 1 . .
C C10 0.50752(12) 0.19245(12) 0.44232(9) 0.01434(18) Uani d 1 . .
C C11 0.35970(13) 0.22881(13) 0.48119(10) 0.01664(19) Uani d 1 . .
H H11A 0.242865 0.161880 0.423787 0.020 Uiso calc 1 . .
C C12 0.38297(13) 0.36220(13) 0.60321(10) 0.01613(19) Uani d 1 . .
H H12A 0.282369 0.387620 0.629065 0.019 Uiso calc 1 . .
C C13 0.83370(13) 0.26098(14) 0.48459(10) 0.0185(2) Uani d 1 . .
C C14 0.48277(13) 0.05290(13) 0.31588(10) 0.01762(19) Uani d 1 . .
C C15 0.79525(14) 0.28892(13) 1.10841(11) 0.0189(2) Uani d 1 . .
H H15A 0.829282 0.225820 1.168675 0.028 Uiso calc 1 . .
H H15B 0.835383 0.260815 1.018882 0.028 Uiso calc 1 . .
H H15C 0.663676 0.252294 1.090253 0.028 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C1 . . 120.56(7) ?
C3 O2 C15 . . 117.05(7) ?
C6 C1 C2 . . 122.83(9) ?
C6 C1 O1 . . 116.08(8) ?
C2 C1 O1 . . 120.80(8) ?
C3 C2 C1 . . 117.62(8) ?
C3 C2 H2A . . 121.2 ?
C1 C2 H2A . . 121.2 ?
O2 C3 C2 . . 123.86(8) ?
O2 C3 C4 . . 115.26(8) ?
C2 C3 C4 . . 120.85(9) ?
C5 C4 C3 . . 119.61(9) ?
C5 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C4 C5 C6 . . 120.85(9) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C1 C6 C5 . . 118.24(9) ?
C1 C6 H6A . . 120.9 ?
C5 C6 H6A . . 120.9 ?
O1 C7 C12 . . 115.57(8) ?
O1 C7 C8 . . 123.07(8) ?
C12 C7 C8 . . 121.20(9) ?
C9 C8 C7 . . 118.33(8) ?
C9 C8 H8A . . 120.8 ?
C7 C8 H8A . . 120.8 ?
C8 C9 C10 . . 121.08(8) ?
C8 C9 C13 . . 119.63(8) ?
C10 C9 C13 . . 119.28(8) ?
C11 C10 C9 . . 119.29(8) ?
C11 C10 C14 . . 119.99(8) ?
C9 C10 C14 . . 120.72(8) ?
C12 C11 C10 . . 120.09(9) ?
C12 C11 H11A . . 120.0 ?
C10 C11 H11A . . 120.0 ?
C11 C12 C7 . . 119.99(9) ?
C11 C12 H12A . . 120.0 ?
C7 C12 H12A . . 120.0 ?
N1 C13 C9 . . 178.59(10) ?
N2 C14 C10 . . 178.88(11) ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.3658(11) ?
O1 C1 . 1.3959(11) ?
O2 C3 . 1.3669(11) ?
O2 C15 . 1.4303(12) ?
N1 C13 . 1.1464(14) ?
N2 C14 . 1.1468(14) ?
C1 C6 . 1.3782(14) ?
C1 C2 . 1.3954(13) ?
C2 C3 . 1.3915(13) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3975(13) ?
C4 C5 . 1.3835(14) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3934(15) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C12 . 1.3939(14) ?
C7 C8 . 1.3942(13) ?
C8 C9 . 1.3914(12) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.4067(13) ?
C9 C13 . 1.4404(13) ?
C10 C11 . 1.3946(13) ?
C10 C14 . 1.4384(13) ?
C11 C12 . 1.3834(13) ?
C11 H11A . 0.9500 ?
C12 H12A . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 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
_geom_hbond_publ_flag
C2 H2A N2 2_656 0.95 2.64 3.5839(13) 175.1 yes
C8 H8A O2 2_767 0.95 2.47 3.3447(11) 152.7 yes
C11 H11A N1 1_455 0.95 2.62 3.2718(13) 126.3 yes
C12 H12A N1 1_455 0.95 2.74 3.3325(13) 120.9 yes
C12 H12A O2 2_667 0.95 2.67 3.5343(12) 151.0 yes

_cod_database_fobs_code 2312062
