#------------------------------------------------------------------------------
#$Date: 2021-07-27 08:09:22 +0300 (Tue, 27 Jul 2021) $
#$Revision: 267764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022405.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_2022405
loop_
_publ_author_name
'Bosch, Eric'
'Bowling, Nathan P.'
'Oburn, Shalisa M.'
_publ_section_title
;
 Conformational control through co-operative nonconventional
 C---H···N hydrogen bonds
;
_journal_coeditor_code           OV3152
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229621007427
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C30 H17 F3 N2 O2'
_chemical_formula_moiety         'C30 H17 F3 N2 O2'
_chemical_formula_sum            'C30 H17 F3 N2 O2'
_chemical_formula_weight         494.45
_chemical_name_systematic
2-(2-{4,5-Dimethoxy-2-[2-(2,3,4-trifluorophenyl)ethynyl]phenyl}ethynyl)-6-[2-(pyridin-2-yl)ethynyl]pyridine
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                104.6970(10)
_cell_angle_beta                 103.0230(10)
_cell_angle_gamma                106.6190(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0037(4)
_cell_length_b                   12.1365(6)
_cell_length_c                   13.4922(6)
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.74
_cell_volume                     1150.30(10)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
_computing_publication_material
;
X-SEED (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 0.998
_diffrn_measured_fraction_theta_max 0.984
_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  0.0222
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14094
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         1.648
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5017
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0498
_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)+(0.0588P)²+0.8077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3939
_reflns_number_total             5017
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3152sup1.cif
_cod_data_source_block           I
_cod_database_code               2022405
_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, -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
F F1 0.93690(15) 0.08813(10) 0.37066(9) 0.0311(3) Uani d 1 . .
O O1 1.31660(17) 0.88155(10) 0.44776(10) 0.0240(3) Uani d 1 . .
N N1 -0.0723(3) -0.13168(17) 0.13171(14) 0.0378(4) Uani d 1 . .
C C1 -0.1550(3) -0.2497(2) 0.11907(17) 0.0425(5) Uani d 1 . .
H H1 -0.082583 -0.289952 0.149735 0.051 Uiso calc 1 . .
F F2 0.69008(17) -0.13974(10) 0.31484(10) 0.0363(3) Uani d 1 . .
O O2 1.49544(17) 0.74849(11) 0.49921(10) 0.0250(3) Uani d 1 . .
N N2 0.2829(2) 0.32816(14) 0.18746(12) 0.0252(3) Uani d 1 . .
C C2 -0.3375(3) -0.3149(2) 0.06455(19) 0.0468(6) Uani d 1 . .
H H2 -0.390915 -0.397588 0.059538 0.056 Uiso calc 1 . .
F F3 0.33172(17) -0.19383(10) 0.20777(11) 0.0415(3) Uani d 1 . .
C C3 -0.4429(3) -0.2590(2) 0.01701(19) 0.0517(7) Uani d 1 . .
H H3 -0.569694 -0.303159 -0.022653 0.062 Uiso calc 1 . .
C C4 -0.3609(3) -0.1355(2) 0.02768(18) 0.0433(6) Uani d 1 . .
H H4 -0.430378 -0.094661 -0.004531 0.052 Uiso calc 1 . .
C C5 -0.1755(3) -0.0755(2) 0.08671(15) 0.0318(4) Uani d 1 . .
C C6 -0.0797(3) 0.0525(2) 0.10419(16) 0.0314(4) Uani d 1 . .
C C7 0.0030(3) 0.1584(2) 0.12007(16) 0.0315(4) Uani d 1 . .
C C8 0.0992(3) 0.28441(18) 0.13770(15) 0.0287(4) Uani d 1 . .
C C9 0.0065(3) 0.3576(2) 0.10534(17) 0.0357(5) Uani d 1 . .
H H9 -0.122574 0.323411 0.069185 0.043 Uiso calc 1 . .
C C10 0.1020(3) 0.4785(2) 0.12585(18) 0.0386(5) Uani d 1 . .
H H10 0.039291 0.529035 0.105646 0.046 Uiso calc 1 . .
C C11 0.2900(3) 0.5265(2) 0.17605(16) 0.0316(4) Uani d 1 . .
H H11 0.359909 0.609952 0.190897 0.038 Uiso calc 1 . .
C C12 0.3745(3) 0.44607(17) 0.20460(14) 0.0248(4) Uani d 1 . .
C C13 0.5703(3) 0.49169(16) 0.25491(15) 0.0247(4) Uani d 1 . .
C C14 0.7342(3) 0.53331(15) 0.29700(14) 0.0229(4) Uani d 1 . .
C C15 0.9293(2) 0.58423(15) 0.34847(14) 0.0208(4) Uani d 1 . .
C C16 1.0247(2) 0.71038(15) 0.37281(14) 0.0211(4) Uani d 1 . .
H H16 0.958310 0.760191 0.355364 0.025 Uiso calc 1 . .
C C17 1.2128(2) 0.76185(15) 0.42156(14) 0.0204(4) Uani d 1 . .
C C18 1.3113(2) 0.68818(15) 0.44922(13) 0.0203(3) Uani d 1 . .
C C19 1.2188(2) 0.56456(15) 0.42579(14) 0.0203(3) Uani d 1 . .
H H19 1.285584 0.515388 0.444351 0.024 Uiso calc 1 . .
C C20 1.0280(2) 0.51129(15) 0.37507(13) 0.0200(3) Uani d 1 . .
C C21 0.9300(2) 0.38337(15) 0.35011(14) 0.0212(4) Uani d 1 . .
C C22 0.8351(2) 0.27841(15) 0.32648(14) 0.0213(4) Uani d 1 . .
C C23 0.7068(2) 0.15664(15) 0.29617(14) 0.0211(4) Uani d 1 . .
C C24 0.7605(2) 0.06497(16) 0.31951(14) 0.0224(4) Uani d 1 . .
C C25 0.6342(3) -0.05248(16) 0.29105(15) 0.0268(4) Uani d 1 . .
C C26 0.4526(3) -0.07785(16) 0.23721(16) 0.0291(4) Uani d 1 . .
C C27 0.3928(3) 0.00974(18) 0.21204(17) 0.0311(4) Uani d 1 . .
H H27 0.262(2) -0.024(2) 0.1754(17) 0.037 Uiso d 1 . .
C C28 0.5200(3) 0.12693(17) 0.24219(15) 0.0258(4) Uani d 1 . .
H H28 0.478(3) 0.1913(17) 0.2256(17) 0.031 Uiso d 1 . .
C C29 1.2213(3) 0.95978(16) 0.42264(16) 0.0257(4) Uani d 1 . .
H H29A 1.156540 0.929730 0.344644 0.039 Uiso calc 1 . .
H H29B 1.310178 1.043171 0.444220 0.039 Uiso calc 1 . .
H H29C 1.132147 0.959855 0.461897 0.039 Uiso calc 1 . .
C C30 1.6007(3) 0.68180(17) 0.53796(16) 0.0288(4) Uani d 1 . .
H H30A 1.550389 0.647855 0.588165 0.043 Uiso calc 1 . .
H H30B 1.729176 0.736752 0.575521 0.043 Uiso calc 1 . .
H H30C 1.594664 0.615085 0.476743 0.043 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
C17 O1 C29 . . 116.89(14) ?
C1 N1 C5 . . 117.94(19) ?
N1 C1 C2 . . 123.5(2) ?
N1 C1 H1 . . 118.3 ?
C2 C1 H1 . . 118.3 ?
C18 O2 C30 . . 117.80(13) ?
C12 N2 C8 . . 116.88(16) ?
C1 C2 C3 . . 118.9(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 119.3(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 117.9(2) ?
C5 C4 H4 . . 121.1 ?
C3 C4 H4 . . 121.1 ?
N1 C5 C4 . . 122.4(2) ?
N1 C5 C6 . . 115.63(17) ?
C4 C5 C6 . . 121.9(2) ?
C7 C6 C5 . . 178.6(2) ?
C6 C7 C8 . . 179.1(2) ?
N2 C8 C9 . . 122.28(18) ?
N2 C8 C7 . . 116.30(17) ?
C9 C8 C7 . . 121.42(18) ?
C10 C9 C8 . . 119.89(19) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 119.56(19) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C10 C11 C12 . . 117.26(19) ?
C10 C11 H11 . . 121.4 ?
C12 C11 H11 . . 121.4 ?
N2 C12 C11 . . 124.10(17) ?
N2 C12 C13 . . 116.87(16) ?
C11 C12 C13 . . 119.04(17) ?
C14 C13 C12 . . 178.00(18) ?
C13 C14 C15 . . 179.1(2) ?
C20 C15 C16 . . 119.37(16) ?
C20 C15 C14 . . 121.26(15) ?
C16 C15 C14 . . 119.37(15) ?
C17 C16 C15 . . 120.70(16) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O1 C17 C16 . . 125.12(15) ?
O1 C17 C18 . . 115.18(15) ?
C16 C17 C18 . . 119.70(15) ?
O2 C18 C19 . . 125.11(15) ?
O2 C18 C17 . . 114.96(14) ?
C19 C18 C17 . . 119.92(16) ?
C18 C19 C20 . . 120.71(16) ?
C18 C19 H19 . . 119.6 ?
C20 C19 H19 . . 119.6 ?
C19 C20 C15 . . 119.59(15) ?
C19 C20 C21 . . 121.44(15) ?
C15 C20 C21 . . 118.97(16) ?
C22 C21 C20 . . 174.56(19) ?
C21 C22 C23 . . 174.48(19) ?
C24 C23 C28 . . 117.76(16) ?
C24 C23 C22 . . 121.90(16) ?
C28 C23 C22 . . 120.33(16) ?
F1 C24 C23 . . 120.29(15) ?
F1 C24 C25 . . 118.35(16) ?
C23 C24 C25 . . 121.35(17) ?
F2 C25 C26 . . 120.96(16) ?
F2 C25 C24 . . 120.12(18) ?
C26 C25 C24 . . 118.91(17) ?
F3 C26 C27 . . 119.98(18) ?
F3 C26 C25 . . 118.14(17) ?
C27 C26 C25 . . 121.88(17) ?
C26 C27 C28 . . 118.57(19) ?
C26 C27 H27 . . 110.7(14) ?
C28 C27 H27 . . 130.7(14) ?
C27 C28 C23 . . 121.51(18) ?
C27 C28 H28 . . 119.1(13) ?
C23 C28 H28 . . 119.4(13) ?
O1 C29 H29A . . 109.5 ?
O1 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
O1 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
O2 C30 H30A . . 109.5 ?
O2 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
O2 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 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
F1 C24 . 1.336(2) ?
O1 C17 . 1.3573(19) ?
O1 C29 . 1.435(2) ?
N1 C1 . 1.342(3) ?
N1 C5 . 1.350(3) ?
C1 C2 . 1.364(3) ?
C1 H1 . 0.9500 ?
F2 C25 . 1.343(2) ?
O2 C18 . 1.359(2) ?
O2 C30 . 1.430(2) ?
N2 C12 . 1.340(2) ?
N2 C8 . 1.350(2) ?
C2 C3 . 1.374(4) ?
C2 H2 . 0.9500 ?
F3 C26 . 1.356(2) ?
C3 C4 . 1.408(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.452(3) ?
C6 C7 . 1.202(3) ?
C7 C8 . 1.431(3) ?
C8 C9 . 1.400(3) ?
C9 C10 . 1.367(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.378(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.417(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.434(3) ?
C13 C14 . 1.199(3) ?
C14 C15 . 1.430(3) ?
C15 C20 . 1.404(2) ?
C15 C16 . 1.413(2) ?
C16 C17 . 1.377(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.415(2) ?
C18 C19 . 1.385(2) ?
C19 C20 . 1.399(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.435(2) ?
C21 C22 . 1.197(2) ?
C22 C23 . 1.429(2) ?
C23 C24 . 1.383(2) ?
C23 C28 . 1.401(3) ?
C24 C25 . 1.387(2) ?
C25 C26 . 1.375(3) ?
C26 C27 . 1.369(3) ?
C27 C28 . 1.384(3) ?
C27 H27 . 0.966(16) ?
C28 H28 . 0.991(15) ?
C29 H29A . 0.9800 ?
C29 H29B . 0.9800 ?
C29 H29C . 0.9800 ?
C30 H30A . 0.9800 ?
C30 H30B . 0.9800 ?
C30 H30C . 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
C11 H11 F3 1_565 0.95 2.41 3.220(2) 142.5 yes
C27 H27 N1 . 0.966(16) 2.470(17) 3.400(3) 161.7(19) yes
C28 H28 N2 . 0.991(15) 2.646(16) 3.612(2) 164.7(17) yes
C29 H29B O2 2_876 0.98 2.37 3.350(2) 174.8 yes

_cod_database_fobs_code 2022405
