#------------------------------------------------------------------------------
#$Date: 2023-04-05 13:56:42 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282398 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312040.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_2312040
loop_
_publ_author_name
'Bosch, Eric'
'Moreno, Bryce S.'
'Bowling, Nathan P.'
_publ_section_title
;
 π-Complexation and C-H hydrogen bonding in the formation of colored
 cocrystals.
;
_journal_coeditor_code           OV3169
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              149
_journal_page_last               157
_journal_paper_doi               10.1107/S2053229623002231
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C14 H4 F4 N2 O4, C15 H14 N2'
_chemical_formula_moiety         'C14 H4 F4 N2 O4, C15 H14 N2'
_chemical_formula_sum            'C29 H18 F4 N4 O4'
_chemical_formula_weight         562.47
_chemical_name_systematic
;
3-{2-[4-(Dimethylamino)phenyl]ethynyl}pyridine;
1-[2-(3,5-dinitrophenyl)ethynyl]-2,3,5,6-tetrafluorobenzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.131(4)
_cell_length_b                   14.423(4)
_cell_length_c                   26.523(7)
_cell_measurement_reflns_used    6048
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.23
_cell_volume                     5023(2)
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
XSeed (Barbour, 2020)
;
_computing_publication_material
;
XSeed (Barbour, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXI CCD'
_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  0.0767
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            60342
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.143
_diffrn_reflns_theta_min         2.097
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0560
_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)+(0.0771P)²+2.8101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1540
_reflns_number_gt                3976
_reflns_number_total             5554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3169sup1.cif
_cod_data_source_block           2
_cod_database_code               2312040
_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+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.38474(11) 0.41632(9) 0.43737(5) 0.0380(4) Uani d 1 . .
O O1 0.31801(13) 0.97332(11) 0.54808(6) 0.0346(4) Uani d 1 . .
N N1 0.39262(14) 0.40849(12) 0.60892(7) 0.0277(4) Uani d 1 . .
C C1 0.40199(16) 0.35428(14) 0.56857(8) 0.0249(4) Uani d 1 . .
H H1 0.404321 0.383090 0.536381 0.030 Uiso calc 1 . .
F F2 0.40359(11) 0.36309(8) 0.34049(5) 0.0370(3) Uani d 1 . .
O O2 0.34149(13) 0.98327(10) 0.62884(6) 0.0332(4) Uani d 1 . .
N N2 0.37851(17) -0.01111(13) 0.29567(7) 0.0367(5) Uani d 1 . .
C C2 0.39061(16) 0.36700(15) 0.65390(9) 0.0282(5) Uani d 1 . .
H H2 0.384300 0.404670 0.683118 0.034 Uiso calc 1 . .
F F3 0.35870(10) 0.67142(9) 0.28711(5) 0.0351(3) Uani d 1 . .
O O3 0.36752(18) 0.70936(13) 0.72859(7) 0.0568(6) Uani d 1 . .
N N3 0.33430(14) 0.93901(12) 0.58941(7) 0.0259(4) Uani d 1 . .
C C3 0.39728(17) 0.27162(16) 0.66019(9) 0.0296(5) Uani d 1 . .
H H3 0.396045 0.245202 0.692996 0.036 Uiso calc 1 . .
F F4 0.33985(10) 0.72583(8) 0.38375(5) 0.0312(3) Uani d 1 . .
O O4 0.37845(15) 0.57505(11) 0.69379(6) 0.0419(5) Uani d 1 . .
N N4 0.37037(15) 0.65946(13) 0.69135(7) 0.0300(4) Uani d 1 . .
C C4 0.40574(16) 0.21554(15) 0.61807(9) 0.0279(5) Uani d 1 . .
H H4 0.409481 0.150057 0.621452 0.034 Uiso calc 1 . .
C C5 0.40866(16) 0.25686(14) 0.57060(8) 0.0245(4) Uani d 1 . .
C C6 0.41423(16) 0.20425(14) 0.52504(9) 0.0266(5) Uani d 1 . .
C C7 0.41224(16) 0.16104(14) 0.48619(9) 0.0266(5) Uani d 1 . .
C C8 0.40680(15) 0.11544(14) 0.43836(8) 0.0247(4) Uani d 1 . .
C C9 0.40617(16) 0.01862(14) 0.43342(8) 0.0256(5) Uani d 1 . .
H H9 0.412462 -0.019045 0.462633 0.031 Uiso calc 1 . .
C C10 0.39657(16) -0.02264(14) 0.38683(8) 0.0265(5) Uani d 1 . .
H H10 0.395229 -0.088382 0.384679 0.032 Uiso calc 1 . .
C C11 0.38867(16) 0.03017(15) 0.34216(8) 0.0253(5) Uani d 1 . .
C C12 0.39060(16) 0.12726(15) 0.34730(9) 0.0275(5) Uani d 1 . .
H H12 0.385972 0.165304 0.318150 0.033 Uiso calc 1 . .
C C13 0.39914(16) 0.16776(14) 0.39422(8) 0.0269(5) Uani d 1 . .
H H13 0.399829 0.233486 0.396587 0.032 Uiso calc 1 . .
C C14 0.3687(2) -0.11100(16) 0.29177(9) 0.0383(6) Uani d 1 . .
H H14A 0.308064 -0.131321 0.310226 0.057 Uiso calc 1 . .
H H14B 0.429238 -0.140616 0.306219 0.057 Uiso calc 1 . .
H H14C 0.362319 -0.128576 0.256217 0.057 Uiso calc 1 . .
C C15 0.3625(2) 0.04253(18) 0.25039(9) 0.0384(6) Uani d 1 . .
H H15A 0.416917 0.088593 0.246992 0.058 Uiso calc 1 . .
H H15B 0.296569 0.074181 0.252385 0.058 Uiso calc 1 . .
H H15C 0.363092 0.001212 0.221055 0.058 Uiso calc 1 . .
C C16 0.37692(17) 0.48011(15) 0.40039(8) 0.0257(5) Uani d 1 . .
C C17 0.38694(17) 0.45312(14) 0.35105(8) 0.0259(5) Uani d 1 . .
C C18 0.38115(16) 0.51602(15) 0.31196(8) 0.0260(5) Uani d 1 . .
H H18 0.388326 0.496944 0.277863 0.031 Uiso calc 1 . .
C C19 0.36461(16) 0.60723(14) 0.32426(8) 0.0247(5) Uani d 1 . .
C C20 0.35458(15) 0.63559(14) 0.37361(8) 0.0243(4) Uani d 1 . .
C C21 0.36105(15) 0.57272(15) 0.41342(8) 0.0230(4) Uani d 1 . .
C C22 0.35608(16) 0.60451(15) 0.46421(8) 0.0246(5) Uani d 1 . .
C C23 0.35522(15) 0.63854(14) 0.50532(8) 0.0241(4) Uani d 1 . .
C C24 0.35445(15) 0.68955(14) 0.55165(8) 0.0230(4) Uani d 1 . .
C C25 0.34476(15) 0.78594(14) 0.54866(8) 0.0222(4) Uani d 1 . .
H H25 0.337937 0.815635 0.516863 0.027 Uiso calc 1 . .
C C26 0.34526(15) 0.83733(14) 0.59255(8) 0.0219(4) Uani d 1 . .
C C27 0.35444(15) 0.79785(14) 0.63971(8) 0.0227(4) Uani d 1 . .
H H27 0.354911 0.834366 0.669514 0.027 Uiso calc 1 . .
C C28 0.36292(16) 0.70242(14) 0.64131(8) 0.0230(4) Uani d 1 . .
C C29 0.36315(15) 0.64641(15) 0.59890(8) 0.0237(4) Uani d 1 . .
H H29 0.368998 0.580953 0.601686 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'
F F 0.0171 0.0103 '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
C1 N1 C2 . . 117.19(19) ?
N1 C1 C5 . . 124.1(2) ?
N1 C1 H1 . . 117.9 ?
C5 C1 H1 . . 117.9 ?
C11 N2 C15 . . 121.85(19) ?
C11 N2 C14 . . 120.17(19) ?
C15 N2 C14 . . 117.4(2) ?
N1 C2 C3 . . 123.4(2) ?
N1 C2 H2 . . 118.3 ?
C3 C2 H2 . . 118.3 ?
O1 N3 O2 . . 124.52(18) ?
O1 N3 C26 . . 118.06(17) ?
O2 N3 C26 . . 117.42(17) ?
C4 C3 C2 . . 119.2(2) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
O3 N4 O4 . . 123.07(19) ?
O3 N4 C28 . . 118.66(18) ?
O4 N4 C28 . . 118.26(18) ?
C3 C4 C5 . . 118.8(2) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C4 C5 C1 . . 117.34(19) ?
C4 C5 C6 . . 122.59(19) ?
C1 C5 C6 . . 120.0(2) ?
C7 C6 C5 . . 175.7(2) ?
C6 C7 C8 . . 175.9(2) ?
C13 C8 C9 . . 117.3(2) ?
C13 C8 C7 . . 119.91(19) ?
C9 C8 C7 . . 122.7(2) ?
C10 C9 C8 . . 121.0(2) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 121.75(19) ?
C9 C10 H10 . . 119.1 ?
C11 C10 H10 . . 119.1 ?
N2 C11 C12 . . 121.3(2) ?
N2 C11 C10 . . 121.70(19) ?
C12 C11 C10 . . 117.0(2) ?
C13 C12 C11 . . 120.7(2) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C8 . . 122.23(19) ?
C12 C13 H13 . . 118.9 ?
C8 C13 H13 . . 118.9 ?
N2 C14 H14A . . 109.5 ?
N2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N2 C15 H15A . . 109.5 ?
N2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
F1 C16 C17 . . 119.53(19) ?
F1 C16 C21 . . 118.96(19) ?
C17 C16 C21 . . 121.49(19) ?
F2 C17 C16 . . 119.19(19) ?
F2 C17 C18 . . 119.14(19) ?
C16 C17 C18 . . 121.7(2) ?
C19 C18 C17 . . 117.4(2) ?
C19 C18 H18 . . 121.3 ?
C17 C18 H18 . . 121.3 ?
F3 C19 C18 . . 119.44(19) ?
F3 C19 C20 . . 118.86(18) ?
C18 C19 C20 . . 121.7(2) ?
F4 C20 C19 . . 119.46(19) ?
F4 C20 C21 . . 119.16(19) ?
C19 C20 C21 . . 121.37(19) ?
C20 C21 C16 . . 116.36(19) ?
C20 C21 C22 . . 120.27(19) ?
C16 C21 C22 . . 123.3(2) ?
C23 C22 C21 . . 174.2(2) ?
C22 C23 C24 . . 173.3(2) ?
C25 C24 C29 . . 119.92(19) ?
C25 C24 C23 . . 117.56(19) ?
C29 C24 C23 . . 122.52(19) ?
C26 C25 C24 . . 119.05(19) ?
C26 C25 H25 . . 120.5 ?
C24 C25 H25 . . 120.5 ?
C27 C26 C25 . . 122.92(19) ?
C27 C26 N3 . . 118.03(18) ?
C25 C26 N3 . . 119.05(19) ?
C26 C27 C28 . . 116.51(19) ?
C26 C27 H27 . . 121.7 ?
C28 C27 H27 . . 121.7 ?
C27 C28 C29 . . 123.8(2) ?
C27 C28 N4 . . 116.99(18) ?
C29 C28 N4 . . 119.20(18) ?
C28 C29 C24 . . 117.79(19) ?
C28 C29 H29 . . 121.1 ?
C24 C29 H29 . . 121.1 ?
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
F1 C16 . 1.349(2) ?
O1 N3 . 1.222(2) ?
N1 C1 . 1.331(3) ?
N1 C2 . 1.335(3) ?
C1 C5 . 1.409(3) ?
C1 H1 . 0.9500 ?
F2 C17 . 1.346(2) ?
O2 N3 . 1.229(2) ?
N2 C11 . 1.376(3) ?
N2 C15 . 1.444(3) ?
N2 C14 . 1.450(3) ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.9500 ?
F3 C19 . 1.354(2) ?
O3 N4 . 1.223(2) ?
N3 C26 . 1.476(3) ?
C3 C4 . 1.384(3) ?
C3 H3 . 0.9500 ?
F4 C20 . 1.343(2) ?
O4 N4 . 1.224(2) ?
N4 C28 . 1.468(3) ?
C4 C5 . 1.393(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.429(3) ?
C6 C7 . 1.204(3) ?
C7 C8 . 1.431(3) ?
C8 C13 . 1.396(3) ?
C8 C9 . 1.403(3) ?
C9 C10 . 1.377(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.412(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.407(3) ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.372(3) ?
C16 C21 . 1.395(3) ?
C17 C18 . 1.380(3) ?
C18 C19 . 1.373(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.378(3) ?
C20 C21 . 1.394(3) ?
C21 C22 . 1.424(3) ?
C22 C23 . 1.196(3) ?
C23 C24 . 1.432(3) ?
C24 C25 . 1.398(3) ?
C24 C29 . 1.404(3) ?
C25 C26 . 1.380(3) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.380(3) ?
C27 C28 . 1.381(3) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.385(3) ?
C29 H29 . 0.9500 ?
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
C29 H29 N1 . 0.95 2.51 3.463(3) 177.5 yes
C2 H2 O4 . 0.95 2.47 3.186(3) 131.6 yes
C15 H15C O2 8_565 0.98 2.47 3.257(3) 136.8 yes
C18 H18 O4 8_565 0.95 2.46 3.398(3) 168.1 yes

_cod_database_fobs_code 2312040
