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#$Date: 2023-10-19 04:37:52 +0300 (Thu, 19 Oct 2023) $
#$Revision: 287035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247528.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_7247528
loop_
_publ_author_name
'Chaudhary, Simran'
'Kędziera, Dariusz'
'Rafiński, Zbigniew'
'Dobrzańska, Liliana'
_publ_section_title
;
 Solvent-induced polymorphism in dipodal N-donor ligands containing a
 biphenyl core
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              30625
_journal_page_last               30632
_journal_paper_doi               10.1039/D3RA05713E
_journal_volume                  13
_journal_year                    2023
_chemical_formula_sum            'C20 H18 N4'
_chemical_formula_weight         314.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-02 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2880(5)
_cell_length_b                   7.9130(2)
_cell_length_c                   22.3941(5)
_cell_measurement_reflns_used    7291
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0290
_cell_measurement_theta_min      3.9080
_cell_volume                     3240.72(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27548
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.576
_diffrn_reflns_theta_min         3.948
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.66756
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0382
_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)+(0.0430P)²+1.0214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2368
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra05713e2.cif
_cod_data_source_block           2c
_cod_database_code               7247528
_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.
;
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.976
_oxdiff_exptl_absorpt_empirical_full_min 0.624
_oxdiff_exptl_absorpt_empirical_full_max 1.822
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.89668(7) -0.07147(16) 0.23956(5) 0.0326(3) Uani 1 1 d . . . . .
N3 N 0.80170(8) -0.18310(18) 0.19181(6) 0.0412(3) Uani 1 1 d . . . . .
N22 N 0.94191(8) 1.19826(18) 0.63404(6) 0.0425(4) Uani 1 1 d . . . . .
N20 N 0.86932(7) 1.03909(16) 0.57820(6) 0.0337(3) Uani 1 1 d . . . . .
C13 C 0.86345(8) 0.54682(19) 0.43402(7) 0.0312(3) Uani 1 1 d . . . . .
C4 C 0.82327(9) -0.2879(2) 0.23732(7) 0.0389(4) Uani 1 1 d . . . . .
H4 H 0.800856 -0.393021 0.246585 0.047 Uiso 1 1 calc R U . . .
C17 C 0.86640(8) 0.6622(2) 0.53426(7) 0.0330(3) Uani 1 1 d . . . . .
H17 H 0.881742 0.652623 0.574653 0.040 Uiso 1 1 calc R U . . .
C21 C 0.87999(9) 1.1129(2) 0.63158(7) 0.0405(4) Uani 1 1 d . . . . .
H21 H 0.846627 1.104548 0.663956 0.049 Uiso 1 1 calc R U . . .
C8 C 0.86028(8) 0.2528(2) 0.30066(7) 0.0350(4) Uani 1 1 d . . . . .
H8 H 0.828037 0.224923 0.268895 0.042 Uiso 1 1 calc R U . . .
C18 C 0.88532(8) 0.5373(2) 0.49372(7) 0.0324(3) Uani 1 1 d . . . . .
H18 H 0.913628 0.443567 0.506736 0.039 Uiso 1 1 calc R U . . .
C10 C 0.88506(8) 0.41612(19) 0.38986(7) 0.0314(3) Uani 1 1 d . . . . .
C12 C 0.97413(8) 0.2170(2) 0.35131(7) 0.0347(4) Uani 1 1 d . . . . .
H12 H 1.020603 0.164269 0.354835 0.042 Uiso 1 1 calc R U . . .
C15 C 0.80305(9) 0.8109(2) 0.45750(7) 0.0383(4) Uani 1 1 d . . . . .
H15 H 0.774942 0.905050 0.444607 0.046 Uiso 1 1 calc R U . . .
C5 C 0.88106(9) -0.2211(2) 0.26739(7) 0.0365(4) Uani 1 1 d . . . . .
H5 H 0.905551 -0.268559 0.300833 0.044 Uiso 1 1 calc R U . . .
C11 C 0.95303(8) 0.3357(2) 0.39317(7) 0.0347(4) Uani 1 1 d . . . . .
H11 H 0.985407 0.363244 0.424882 0.042 Uiso 1 1 calc R U . . .
C7 C 0.92844(8) 0.1734(2) 0.30412(7) 0.0320(3) Uani 1 1 d . . . . .
C6 C 0.95331(8) 0.0500(2) 0.25667(7) 0.0355(4) Uani 1 1 d . . . . .
H6A H 0.968637 0.114070 0.220815 0.043 Uiso 1 1 calc R U . . .
H6B H 0.996461 -0.012508 0.271640 0.043 Uiso 1 1 calc R U . . .
C9 C 0.83896(8) 0.3708(2) 0.34247(7) 0.0338(4) Uani 1 1 d . . . . .
H9 H 0.792208 0.422244 0.339118 0.041 Uiso 1 1 calc R U . . .
C23 C 0.97209(9) 1.1778(2) 0.57858(7) 0.0382(4) Uani 1 1 d . . . . .
H23 H 1.017574 1.224364 0.566396 0.046 Uiso 1 1 calc R U . . .
C14 C 0.82116(8) 0.6856(2) 0.41695(7) 0.0353(4) Uani 1 1 d . . . . .
H14 H 0.804529 0.694118 0.376876 0.042 Uiso 1 1 calc R U . . .
C16 C 0.82527(8) 0.8012(2) 0.51663(7) 0.0348(4) Uani 1 1 d . . . . .
C2 C 0.84747(9) -0.0549(2) 0.19479(7) 0.0377(4) Uani 1 1 d . . . . .
H2 H 0.846101 0.039057 0.168388 0.045 Uiso 1 1 calc R U . . .
C19 C 0.80509(8) 0.9385(2) 0.56032(8) 0.0400(4) Uani 1 1 d . . . . .
H19A H 0.768259 1.013922 0.541876 0.048 Uiso 1 1 calc R U . . .
H19B H 0.782818 0.886821 0.596230 0.048 Uiso 1 1 calc R U . . .
C24 C 0.92823(9) 1.0819(2) 0.54339(7) 0.0368(4) Uani 1 1 d . . . . .
H24 H 0.936580 1.050792 0.502984 0.044 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 0.0181 0.0091 '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 0.0311 0.0180 '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
C2 N1 C5 106.42(13) . . ?
C2 N1 C6 126.89(13) . . ?
C5 N1 C6 126.64(13) . . ?
C2 N3 C4 104.22(14) . . ?
C21 N22 C23 104.33(13) . . ?
C21 N20 C24 106.49(13) . . ?
C21 N20 C19 126.28(14) . . ?
C24 N20 C19 127.19(13) . . ?
C14 C13 C18 117.57(14) . . ?
C14 C13 C10 120.86(14) . . ?
C18 C13 C10 121.56(14) . . ?
C5 C4 N3 110.85(15) . . ?
C5 C4 H4 124.6 . . ?
N3 C4 H4 124.6 . . ?
C18 C17 C16 120.90(14) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N22 C21 N20 112.58(15) . . ?
N22 C21 H21 123.7 . . ?
N20 C21 H21 123.7 . . ?
C9 C8 C7 121.27(14) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C17 C18 C13 121.10(15) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C11 C10 C9 117.26(14) . . ?
C11 C10 C13 121.22(13) . . ?
C9 C10 C13 121.50(14) . . ?
C11 C12 C7 121.08(14) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C14 C15 C16 121.09(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C4 C5 N1 105.85(14) . . ?
C4 C5 H5 127.1 . . ?
N1 C5 H5 127.1 . . ?
C12 C11 C10 121.44(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C12 C7 C8 117.80(14) . . ?
C12 C7 C6 120.87(14) . . ?
C8 C7 C6 121.28(14) . . ?
N1 C6 C7 113.25(12) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C9 C10 121.15(14) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C24 C23 N22 110.80(15) . . ?
C24 C23 H23 124.6 . . ?
N22 C23 H23 124.6 . . ?
C15 C14 C13 121.08(15) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C15 C16 C17 118.24(15) . . ?
C15 C16 C19 120.53(15) . . ?
C17 C16 C19 121.23(15) . . ?
N3 C2 N1 112.65(15) . . ?
N3 C2 H2 123.7 . . ?
N1 C2 H2 123.7 . . ?
N20 C19 C16 111.72(12) . . ?
N20 C19 H19A 109.3 . . ?
C16 C19 H19A 109.3 . . ?
N20 C19 H19B 109.3 . . ?
C16 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C23 C24 N20 105.79(14) . . ?
C23 C24 H24 127.1 . . ?
N20 C24 H24 127.1 . . ?
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
N1 C2 1.354(2) . ?
N1 C5 1.368(2) . ?
N1 C6 1.4641(19) . ?
N3 C2 1.317(2) . ?
N3 C4 1.372(2) . ?
N22 C21 1.320(2) . ?
N22 C23 1.369(2) . ?
N20 C21 1.345(2) . ?
N20 C24 1.372(2) . ?
N20 C19 1.474(2) . ?
C13 C14 1.396(2) . ?
C13 C18 1.398(2) . ?
C13 C10 1.484(2) . ?
C4 C5 1.360(2) . ?
C4 H4 0.9500 . ?
C17 C18 1.386(2) . ?
C17 C16 1.390(2) . ?
C17 H17 0.9500 . ?
C21 H21 0.9500 . ?
C8 C9 1.378(2) . ?
C8 C7 1.398(2) . ?
C8 H8 0.9500 . ?
C18 H18 0.9500 . ?
C10 C11 1.399(2) . ?
C10 C9 1.402(2) . ?
C12 C11 1.382(2) . ?
C12 C7 1.391(2) . ?
C12 H12 0.9500 . ?
C15 C14 1.385(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C7 C6 1.513(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9 0.9500 . ?
C23 C24 1.356(2) . ?
C23 H23 0.9500 . ?
C14 H14 0.9500 . ?
C16 C19 1.508(2) . ?
C2 H2 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C24 H24 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3 C4 C5 0.58(19) . . . . ?
C23 N22 C21 N20 0.32(19) . . . . ?
C24 N20 C21 N22 -0.87(19) . . . . ?
C19 N20 C21 N22 -178.41(15) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C10 C13 C18 C17 178.35(14) . . . . ?
C14 C13 C10 C11 144.67(15) . . . . ?
C18 C13 C10 C11 -34.4(2) . . . . ?
C14 C13 C10 C9 -34.0(2) . . . . ?
C18 C13 C10 C9 146.93(15) . . . . ?
N3 C4 C5 N1 -0.72(18) . . . . ?
C2 N1 C5 C4 0.55(17) . . . . ?
C6 N1 C5 C4 178.02(14) . . . . ?
C7 C12 C11 C10 0.2(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C13 C10 C11 C12 -178.37(15) . . . . ?
C11 C12 C7 C8 -0.4(2) . . . . ?
C11 C12 C7 C6 176.86(15) . . . . ?
C9 C8 C7 C12 0.2(2) . . . . ?
C9 C8 C7 C6 -177.11(15) . . . . ?
C2 N1 C6 C7 91.62(19) . . . . ?
C5 N1 C6 C7 -85.35(18) . . . . ?
C12 C7 C6 N1 137.78(15) . . . . ?
C8 C7 C6 N1 -45.0(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C11 C10 C9 C8 -0.6(2) . . . . ?
C13 C10 C9 C8 178.11(15) . . . . ?
C21 N22 C23 C24 0.36(19) . . . . ?
C16 C15 C14 C13 -1.1(2) . . . . ?
C18 C13 C14 C15 1.5(2) . . . . ?
C10 C13 C14 C15 -177.68(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C19 -179.93(15) . . . . ?
C18 C17 C16 C15 0.6(2) . . . . ?
C18 C17 C16 C19 -179.39(14) . . . . ?
C4 N3 C2 N1 -0.22(19) . . . . ?
C5 N1 C2 N3 -0.21(18) . . . . ?
C6 N1 C2 N3 -177.67(14) . . . . ?
C21 N20 C19 C16 -148.02(16) . . . . ?
C24 N20 C19 C16 34.9(2) . . . . ?
C15 C16 C19 N20 -110.10(17) . . . . ?
C17 C16 C19 N20 69.9(2) . . . . ?
N22 C23 C24 N20 -0.88(19) . . . . ?
C21 N20 C24 C23 1.03(17) . . . . ?
C19 N20 C24 C23 178.54(15) . . . . ?
