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_7133549
_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             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                 111.79(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.72(2)
_cell_length_b                   4.4815(7)
_cell_length_c                   19.84(3)
_cell_measurement_reflns_used    624
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.6700
_cell_measurement_theta_min      2.7060
_cell_volume                     1380(3)
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_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 0.314
_diffrn_measured_fraction_theta_max 0.280
_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     20.00  79.00   1.00   35.00    --   27.05-114.00  44.00   59
  2  \w     -3.00  52.00   1.00   35.00    --   27.05 -53.00  17.00   55
  3  \w    -28.00  -1.00   1.00   35.00    --   27.05  97.00 -35.00   27
  4  \w    -32.00  22.00   1.00   35.00    --   27.05  39.00 -12.00   54
  5  \w     15.00  60.00   1.00   35.00    --   27.05 -77.00-150.00   45
  6  \w    -28.00  -1.00   1.00   35.00    --   27.05  97.00 143.00   27
  7  \w    -33.00  22.00   1.00   35.00    --   27.05  39.00 167.00   55
  8  \w    -22.00  32.00   1.00   35.00    --  -27.91 -39.00  12.00   54
  9  \w    -22.00  47.00   1.00   35.00    --  -27.91 -19.00-180.00   69
 10  \w    -39.00  30.00   1.00   35.00    --  -27.91  13.00  -3.00   69
 11  \w      1.00  27.00   1.00   35.00    --  -27.91 -97.00-143.00   26
 12  \w    -52.00  17.00   1.00   35.00    --  -27.91  53.00 162.00   69
 13  \w     -8.00  47.00   1.00   35.00    --   27.05 -39.00  12.00   55
 14  \w    -47.00  -8.00   1.00   35.00    --   27.05  19.00-150.00   39
 15  \w     -8.00  52.00   1.00   35.00    --   27.05 -53.00-162.00   60
 16  \w     69.00 102.00   1.00   35.00    --   27.05 178.00 -90.00   33
 17  \w   -111.00 -78.00   1.00   35.00    --  -27.91 178.00 -90.00   33
 18  \w    -35.00 -10.00   1.00   35.00    --  -27.91   0.00-180.00   25
 19  \w    -63.00   6.00   1.00   35.00    --  -27.91  81.00 -29.00   69
 20  \w     10.00  35.00   1.00   35.00    --  -27.91-114.00  44.00   25
;
_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      0.0368009000
_diffrn_orient_matrix_UB_12      0.0234784000
_diffrn_orient_matrix_UB_13      0.0322991000
_diffrn_orient_matrix_UB_21      -0.0089563000
_diffrn_orient_matrix_UB_22      -0.1340369000
_diffrn_orient_matrix_UB_23      0.0147009000
_diffrn_orient_matrix_UB_31      0.0256910000
_diffrn_orient_matrix_UB_32      -0.0801212000
_diffrn_orient_matrix_UB_33      -0.0152287000
_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  0.1016
_diffrn_reflns_av_unetI/netI     0.1229
_diffrn_reflns_Laue_measured_fraction_full 0.314
_diffrn_reflns_Laue_measured_fraction_max 0.280
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2493
_diffrn_reflns_point_group_measured_fraction_full 0.314
_diffrn_reflns_point_group_measured_fraction_max 0.280
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.923
_diffrn_reflns_theta_min         2.733
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         420
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.2022
_refine_ls_R_factor_gt           0.0864
_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^)+(0.0829P)^2^+1.6991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.2278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                192
_reflns_number_total             420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02183e3.cif
_cod_data_source_block           etyfum_088
_cod_depositor_comments
'Adding full bibliography for 7133545--7133558.cif.'
_cod_database_code               7133549
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C4O4H4, N2C12H12'
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.968
_exptl_oxdiff_absorpt_process_details
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.398     0.453
         range of gasket transmission (min-max)           1.000     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 300.0 microns, radius = 212.0 microns
    Gasket absorption coeff =         0.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Absorption coeff of pressure medium =   0.00 mm-1
;
_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. Restrained distances
 C7-O2
 1.2 with sigma of 0.02
 C7-O1
 1.3 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8)
3.c Idealised tetrahedral OH refined with riding coordinates:
 O1(H1A)
;
_shelx_res_checksum              99307
_shelx_hkl_checksum              16112
_ins_header
;
TITL ETYFUM_088 in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.719239   4.481489  19.839214  90.0000 111.7915  90.0000
ZERR    4.00   0.022137   0.000694   0.028670   0.0000   0.1763   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 0.03 0.20 0.31
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 1.989
_oxdiff_exptl_absorpt_empirical_full_min 0.593