Metal-free negative linear compressibility (NLC) material - the cocrystal of 1,2-bis(4-pyridyl)ethane and fumaric acid.
Patyk-Kaźmierczak, Ewa; Kaźmierczak, Michał; Chemical communications (Cambridge, England) 60 (2024) 10310–10313; doi:10.1039/d4cc02183e

data_7133552
_publ_section_title
;
 Metal-free negative linear compressibility (NLC) material - the cocrystal
 of 1,2-bis(4-pyridyl)ethane and fumaric acid.
;
_journal_issue                   75
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10310
_journal_page_last               10313
_journal_paper_doi               10.1039/d4cc02183e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-06-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.18(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.836(10)
_cell_length_b                   4.1496(11)
_cell_length_c                   20.120(14)
_cell_measurement_reflns_used    534
_cell_measurement_temperature    298
_cell_measurement_theta_max      19.5490
_cell_measurement_theta_min      4.1210
_cell_volume                     1272.1(15)
_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_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_pressure         2440000
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.284
_diffrn_measured_fraction_theta_max 0.268
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00 -15.00   1.00   15.00    --   -0.27  37.00-150.00   47
  2  \w    -49.00  11.00   1.00   15.00    --   -0.27  81.00 -29.00   60
  3  \w     -1.00  68.00   1.00   22.50    --   26.72 -81.00-151.00   69
  4  \w     70.00 111.00   1.00   22.50    --   26.72 178.00  90.00   41
  5  \w    -27.00  22.00   1.00   22.50    --   26.72 -19.00-150.00   49
  6  \w    -19.00  22.00   1.00   22.50    --   26.72  53.00 -17.00   41
  7  \w    -38.00  27.00   1.00   22.50    --   26.72  39.00 167.00   65
  8  \w    -30.00   4.00   1.00   22.50    --   26.72  97.00 -35.00   34
  9  \w    -35.00 -15.00   1.00   22.50    --   26.72  37.00   0.00   20
 10  \w    -48.00  16.00   1.00   22.50    --   26.72  37.00-180.00   64
 11  \w    -51.00 -17.00   1.00   22.50    --   26.72 134.00 123.00   34
 12  \w    -10.00  62.00   1.00   22.50    --   26.72 -67.00  23.00   72
 13  \w    -22.00  11.00   1.00   22.50    --   26.72  81.00 151.00   33
 14  \w     -4.00  16.00   1.00   22.50    --  -27.26 -57.00  30.00   20
 15  \w    -52.00  27.00   1.00   22.50    --  -27.26  39.00 -12.00   79
 16  \w    -57.00  22.00   1.00   22.50    --  -27.26  53.00 -17.00   79
 17  \w    -27.00  38.00   1.00   22.50    --  -27.26 -39.00-167.00   65
 18  \w    -16.00  49.00   1.00   22.50    --  -27.26 -37.00-180.00   65
 19  \w    -22.00  18.00   1.00   22.50    --  -27.26 -53.00  17.00   40
 20  \w   -121.00 -69.00   1.00   22.50    --  -27.26 178.00 -90.00   52
 21  \w      5.00  37.00   1.00   22.50    --  -27.26-114.00-136.00   32
 22  \w    -75.00   4.00   1.00   22.50    --  -27.26  97.00 143.00   79
 23  \w      5.00  37.00   1.00   22.50    --  -27.26-114.00  44.00   32
 24  \w    -17.00  16.00   1.00   22.50    --  -27.26 -67.00-157.00   33
 25  \w    -16.00  35.00   1.00   15.00    --   -0.27 -37.00-150.00   51
 26  \w     -4.00  18.00   1.00   22.50    --   26.72 -57.00  60.00   22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0320686000
_diffrn_orient_matrix_UB_12      0.0911897000
_diffrn_orient_matrix_UB_13      -0.0286527000
_diffrn_orient_matrix_UB_21      0.0307279000
_diffrn_orient_matrix_UB_22      0.0322919000
_diffrn_orient_matrix_UB_23      -0.0147004000
_diffrn_orient_matrix_UB_31      -0.0138580000
_diffrn_orient_matrix_UB_32      -0.1409157000
_diffrn_orient_matrix_UB_33      -0.0219649000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_Laue_measured_fraction_full 0.284
_diffrn_reflns_Laue_measured_fraction_max 0.268
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1394
_diffrn_reflns_point_group_measured_fraction_full 0.284
_diffrn_reflns_point_group_measured_fraction_max 0.268
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.781
_diffrn_reflns_theta_min         2.658
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0696
_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/[\s^2^(Fo^2^)+(0.1175P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.2360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                173
_reflns_number_total             327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02183e3.cif
_cod_data_source_block           etyfum_244
_cod_depositor_comments
'Adding full bibliography for 7133545--7133558.cif.'
_cod_original_cell_volume        1272.0(14)
_cod_database_code               7133552
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H12 N2, C4 H4 O4'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.976
_diffrn.ambient_pressure_su      20000
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              11582
_olex2_exptl_crystal_mounting_method
'Single crystal grown at ambient conditions was mounted in Merrill-Bassett diamond anvil cell, compressed to 3 GPa and then decompressed to 2.44(2) GPa. Daphne oil 7575 was used as hydrostatic medium.'
_shelx_hkl_checksum              9636
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.687