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_7133545
_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         300.316
_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'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-12 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.083(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6937(2)
_cell_length_b                   4.8165(1)
_cell_length_c                   19.6871(3)
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.2350
_cell_measurement_theta_min      2.9980
_cell_volume                     1495.96(5)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9879
_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   -116.00 -17.00   1.00    2.00    --  -41.23 -37.00   0.00   99
  2  \w   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00 -60.00  101
  3  \w      6.00  97.00   1.00    2.00    --   41.23-125.00 -90.00   91
  4  \w     59.00 158.00   1.00    3.00    --  112.00  15.00-180.00   99
  5  \w     36.00 106.00   1.00    3.00    --  112.00 -77.00  90.00   70
  6  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00 -30.00   31
  7  \w     86.00 158.00   1.00    3.00    --  112.00  45.00  60.00   72
  8  \w     59.00 158.00   1.00    3.00    --  112.00  15.00  90.00   99
  9  \w     36.00 109.00   1.00    3.00    --  112.00-111.00-180.00   73
 10  \w     84.00 158.00   1.00    3.00    --  112.00  30.00 -30.00   74
 11  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00-150.00   31
 12  \w     86.00 158.00   1.00    3.00    --  112.00  45.00 -90.00   72
 13  \w     36.00 106.00   1.00    3.00    --  112.00 -77.00-180.00   70
 14  \w    -42.00  33.00   1.00    2.00    --  -41.23  37.00 -30.00   75
 15  \w   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00  90.00  101
 16  \w   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00-180.00  101
 17  \w    -33.00  42.00   1.00    2.00    --   41.23 -37.00  30.00   75
 18  \w     83.00 158.00   1.00    3.00    --  112.00  61.00-180.00   75
 19  \w     83.00 158.00   1.00    3.00    --  112.00  61.00-150.00   75
 20  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00  30.00   31
 21  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00-120.00   31
 22  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00 -90.00   31
 23  \w     82.00 158.00   1.00    3.00    --  112.00  77.00 -30.00   76
 24  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00   0.00   31
 25  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00 -60.00   31
 26  \w    -26.00  39.00   1.00    2.00    --  -41.23  19.00  30.00   65
 27  \w   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00   0.00  101
 28  \w   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00-120.00  101
 29  \w      6.00  97.00   1.00    2.00    --   41.23-125.00-180.00   91
 30  \w     36.00 109.00   1.00    3.00    --  112.00-111.00  90.00   73
 31  \w     83.00 158.00   1.00    3.00    --  112.00  61.00  90.00   75
 32  \w     36.00 109.00   1.00    3.00    --  112.00-111.00   0.00   73
 33  \w     82.00 158.00   1.00    3.00    --  112.00  77.00   0.00   76
 34  \w     40.00  71.00   1.00    3.00    --  112.00 -61.00-180.00   31
 35  \w     83.00 158.00   1.00    3.00    --  112.00  61.00 150.00   75
 36  \w     83.00 158.00   1.00    3.00    --  112.00  61.00-120.00   75
 37  \w     82.00 158.00   1.00    3.00    --  112.00  77.00 -90.00   76
 38  \w    -99.00  -8.00   1.00    2.00    --  -41.23 128.00-111.00   91
 39  \w   -116.00 -17.00   1.00    2.00    --  -41.23 -37.00 -60.00   99
 40  \w     17.00 116.00   1.00    2.00    --   41.23  37.00-120.00   99
 41  \w    -39.00  26.00   1.00    2.00    --   41.23 -19.00-180.00   65
 42  \w     82.00 158.00   1.00    3.00    --  112.00  77.00 -60.00   76
 43  \w     36.00  97.00   1.00    3.00    --  112.00-111.00 -60.00   61
 44  \w     83.00 158.00   1.00    3.00    --  112.00  61.00 120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0204956000
_diffrn_orient_matrix_UB_12      -0.0324695000
_diffrn_orient_matrix_UB_13      -0.0704057000
_diffrn_orient_matrix_UB_21      -0.0950225000
_diffrn_orient_matrix_UB_22      0.0239634000
_diffrn_orient_matrix_UB_23      -0.0433923000
_diffrn_orient_matrix_UB_31      0.0092712000
_diffrn_orient_matrix_UB_32      0.3173348000
_diffrn_orient_matrix_UB_33      -0.0039146000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9879
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12205
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9879
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.40
_diffrn_reflns_theta_min         4.75
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.799
_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    1.333
_exptl_crystal_description       plate
_exptl_crystal_F_000             634.329
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.1175
_refine_diff_density_min         -0.1021
_refine_diff_density_rms         0.0188
_refine_ls_d_res_high            0.7932
_refine_ls_d_res_low             9.3026
_refine_ls_extinction_coef       0.0044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0766
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0766
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0517
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              0
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -24
_reflns_number_gt                1421
_reflns_number_total             1548
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc02183e3.cif
_cod_data_source_block           ETYFUM
_cod_depositor_comments
'Adding full bibliography for 7133545--7133558.cif.'
_cod_database_code               7133545
_chemical_oxdiff_formula         'C12 H12 N2, C4 H4 O4'
_olex2_refinement_description
;
;
_ins_header
;
TITL ETYFUM in I2/a 
REM I2/a (#15 in standard setting)
CELL 1.54184  16.693694   4.816505  19.687145  90.0000 109.0830  90.0000
ZERR    4.00   0.000218   0.000068   0.000263   0.0000   0.0015   0.0000
LATT  2
SYMM -x+1/2, y,-z 
SFAC C H N O
UNIT 64.00 64.00 8.00 16.00
SIZE 0.09 0.17 0.46
TREF
HKLF 4
END
;
_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 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.685