#------------------------------------------------------------------------------
#$Date: 2023-10-19 04:37:52 +0300 (Thu, 19 Oct 2023) $
#$Revision: 287035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247527.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_7247527
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            'C24 H20 N2'
_chemical_formula_weight         336.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 100.4410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.76800(5)
_cell_length_b                   9.98210(10)
_cell_length_c                   15.60390(10)
_cell_measurement_reflns_used    23887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1210
_cell_measurement_theta_min      2.8640
_cell_volume                     883.546(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29193
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.323
_diffrn_reflns_theta_min         2.880
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52344
_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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3501
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+0.1306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                3451
_reflns_number_total             3501
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra05713e2.cif
_cod_data_source_block           1MeOH
_cod_original_cell_volume        883.546(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7247527
_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   0.951
_shelx_estimated_absorpt_t_max   0.972
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.5171(3) 0.59222(16) 0.42598(9) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.7218(3) 0.5253(2) 0.43555(11) 0.0326(4) Uani 1 1 d . . . . .
H2 H 0.806128 0.527401 0.388606 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8182(3) 0.45364(18) 0.50912(11) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.964252 0.408372 0.511908 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6991(3) 0.44832(16) 0.57929(10) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.4852(3) 0.51520(17) 0.56968(10) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.395367 0.513079 0.615029 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4033(3) 0.58522(18) 0.49340(11) 0.0286(3) Uani 1 1 d . . . . .
H6 H 0.257292 0.631105 0.488711 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8103(3) 0.37396(18) 0.66132(10) 0.0253(3) Uani 1 1 d . . . . .
H7B H 0.806715 0.276786 0.648445 0.030 Uiso 1 1 calc R U . . .
H7A H 0.977726 0.401070 0.676937 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6931(3) 0.39730(16) 0.73929(9) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.7866(3) 0.48626(16) 0.80529(9) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.928358 0.532666 0.801790 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6762(3) 0.50848(16) 0.87631(9) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.744775 0.568694 0.920923 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4652(2) 0.44305(15) 0.88275(9) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.3720(3) 0.35402(15) 0.81601(10) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.228548 0.308810 0.818680 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4845(3) 0.33036(16) 0.74607(10) 0.0224(3) Uani 1 1 d . . . . .
H13 H 0.418950 0.267992 0.702344 0.027 Uiso 1 1 calc R U . . .
C14 C 0.3428(2) 0.46600(15) 0.95734(9) 0.0187(3) Uani 1 1 d . . . . .
C15 C 0.3430(3) 0.59186(16) 0.99685(10) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.424119 0.664188 0.975930 0.026 Uiso 1 1 calc R U . . .
C16 C 0.2266(3) 0.61269(15) 1.06603(10) 0.0215(3) Uani 1 1 d . . . . .
H16 H 0.231535 0.698717 1.092329 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1027(2) 0.50968(15) 1.09764(9) 0.0197(3) Uani 1 1 d . . . . .
C18 C 0.1013(3) 0.38389(15) 1.05841(9) 0.0203(3) Uani 1 1 d . . . . .
H18 H 0.018906 0.311849 1.079060 0.024 Uiso 1 1 calc R U . . .
C19 C 0.2193(3) 0.36313(15) 0.98957(9) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.215817 0.276787 0.963764 0.024 Uiso 1 1 calc R U . . .
C20 C -0.0360(3) 0.53738(16) 1.16992(11) 0.0247(3) Uani 1 1 d . . . . .
H20A H 0.043267 0.610371 1.207099 0.030 Uiso 1 1 calc R U . . .
H20B H -0.195101 0.569530 1.143272 0.030 Uiso 1 1 calc R U . . .
C21 C -0.0619(3) 0.41877(15) 1.22667(9) 0.0210(3) Uani 1 1 d . . . . .
C22 C 0.1199(3) 0.37997(17) 1.29341(10) 0.0253(3) Uani 1 1 d . . . . .
H22 H 0.264477 0.427963 1.303759 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0873(3) 0.27043(18) 1.34462(11) 0.0288(4) Uani 1 1 d . . . . .
H23 H 0.213139 0.245776 1.390006 0.035 Uiso 1 1 calc R U . . .
N24 N -0.1099(3) 0.19746(15) 1.33408(9) 0.0301(3) Uani 1 1 d . . . . .
C25 C -0.2831(3) 0.23560(18) 1.26990(11) 0.0303(4) Uani 1 1 d . . . . .
H25 H -0.425462 0.185492 1.261080 0.036 Uiso 1 1 calc R U . . .
C26 C -0.2684(3) 0.34338(17) 1.21545(11) 0.0268(3) Uani 1 1 d . . . . .
H26 H -0.397817 0.365772 1.170880 0.032 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
C6 N1 C2 115.69(14) . . ?
N1 C2 C3 124.34(15) . . ?
N1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C2 C3 C4 119.40(15) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 116.86(14) . . ?
C5 C4 C7 123.93(14) . . ?
C3 C4 C7 119.20(14) . . ?
C4 C5 C6 119.54(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 124.16(16) . . ?
N1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
C8 C7 C4 114.89(13) . . ?
C8 C7 H7B 108.5 . . ?
C4 C7 H7B 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C4 C7 H7A 108.5 . . ?
H7B C7 H7A 107.5 . . ?
C9 C8 C13 118.19(14) . . ?
C9 C8 C7 121.55(14) . . ?
C13 C8 C7 120.25(14) . . ?
C10 C9 C8 121.24(14) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.75(14) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 117.65(13) . . ?
C12 C11 C14 120.54(13) . . ?
C10 C11 C14 121.81(13) . . ?
C13 C12 C11 121.46(14) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C8 120.68(14) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C19 C14 C15 117.50(13) . . ?
C19 C14 C11 121.05(13) . . ?
C15 C14 C11 121.44(13) . . ?
C16 C15 C14 121.07(14) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.14(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 118.10(13) . . ?
C16 C17 C20 120.06(14) . . ?
C18 C17 C20 121.77(14) . . ?
C19 C18 C17 120.61(14) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 121.57(14) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C21 C20 C17 114.56(13) . . ?
C21 C20 H20A 108.6 . . ?
C17 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C17 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C26 117.04(15) . . ?
C22 C21 C20 121.22(15) . . ?
C26 C21 C20 121.73(14) . . ?
C23 C22 C21 119.22(15) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
N24 C23 C22 124.07(15) . . ?
N24 C23 H23 118.0 . . ?
C22 C23 H23 118.0 . . ?
C25 N24 C23 116.20(15) . . ?
N24 C25 C26 124.18(16) . . ?
N24 C25 H25 117.9 . . ?
C26 C25 H25 117.9 . . ?
C25 C26 C21 119.29(15) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?
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 C6 1.339(2) . ?
N1 C2 1.341(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 C7 1.518(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.513(2) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 C9 1.392(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(2) . ?
C11 C14 1.4844(19) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.395(2) . ?
C14 C15 1.399(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(2) . ?
C17 C20 1.521(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.502(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.392(2) . ?
C21 C26 1.393(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 N24 1.336(2) . ?
C23 H23 0.9500 . ?
N24 C25 1.335(2) . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 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
C6 N1 C2 C3 -0.7(3) . . . . ?
N1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C2 C3 C4 C7 -177.64(16) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C7 C4 C5 C6 177.20(16) . . . . ?
C2 N1 C6 C5 0.3(3) . . . . ?
C4 C5 C6 N1 0.8(3) . . . . ?
C5 C4 C7 C8 -10.3(2) . . . . ?
C3 C4 C7 C8 168.22(15) . . . . ?
C4 C7 C8 C9 -100.40(17) . . . . ?
C4 C7 C8 C13 78.81(19) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C10 179.20(14) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C10 C11 C14 -179.38(14) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C14 C11 C12 C13 -179.51(13) . . . . ?
C11 C12 C13 C8 -1.3(2) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
C7 C8 C13 C12 -178.10(14) . . . . ?
C12 C11 C14 C19 33.7(2) . . . . ?
C10 C11 C14 C19 -146.14(15) . . . . ?
C12 C11 C14 C15 -145.01(15) . . . . ?
C10 C11 C14 C15 35.1(2) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
C11 C14 C15 C16 179.48(13) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C15 C16 C17 C20 -176.23(14) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C20 C17 C18 C19 176.62(14) . . . . ?
C17 C18 C19 C14 0.1(2) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
C11 C14 C19 C18 -179.05(13) . . . . ?
C16 C17 C20 C21 -151.97(15) . . . . ?
C18 C17 C20 C21 31.0(2) . . . . ?
C17 C20 C21 C22 79.85(18) . . . . ?
C17 C20 C21 C26 -100.61(17) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?
C20 C21 C22 C23 179.48(14) . . . . ?
C21 C22 C23 N24 0.3(2) . . . . ?
C22 C23 N24 C25 -0.3(2) . . . . ?
C23 N24 C25 C26 0.1(2) . . . . ?
N24 C25 C26 C21 0.1(2) . . . . ?
C22 C21 C26 C25 -0.1(2) . . . . ?
C20 C21 C26 C25 -179.65(14) . . . . ?
