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_7133550
_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             2024-03-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-18 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.9(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.89(5)
_cell_length_b                   3.9930(4)
_cell_length_c                   20.19(5)
_cell_measurement_reflns_used    875
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.1100
_cell_measurement_theta_min      4.0670
_cell_volume                     1225(6)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_pressure         3580000
_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 0.162
_diffrn_measured_fraction_theta_max 0.136
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -35.00  19.75   0.75   30.00   0.00 -30.00   0.00    --    73
  2  \f    140.00 200.00   0.75   30.00   0.00 -30.00   0.00    --    80
  3  \f    160.00 217.00   0.75   30.00   0.00  30.00   0.00    --    76
  4  \f    -20.00  34.75   0.75   30.00   0.00  30.00   0.00    --    73
  5  \w    -24.00  24.00   0.75   30.00    --   30.00  39.46 -12.90   64
  6  \w    -24.00  24.00   0.75   30.00    --   30.00  39.46 167.10   64
  7  \w    -50.00  10.00   0.75   30.00    --  -30.00  39.46 167.10   80
  8  \w    -50.00  10.00   0.75   30.00    --  -30.00  39.46 -12.90   80
  9  \w    -64.00  -8.50   0.75   30.00    --  -30.00  81.40 -28.90   74
 10  \w    -64.00  -8.50   0.75   30.00    --  -30.00  81.40 151.10   74
 11  \w    -19.00   8.00   0.75   30.00    --   30.00  81.40 151.10   36
 12  \w    -19.00   8.00   0.75   30.00    --   30.00  81.40 -28.90   36
 13  \w    -43.00 -21.25   0.75   30.00    --   30.00 134.60 -56.90   29
 14  \w    -43.00 -21.25   0.75   30.00    --   30.00 134.60 123.10   29
 15  \w    -90.00 -36.00   0.75   30.00    --  -30.00 134.60 123.10   72
 16  \w    -90.00 -36.00   0.75   30.00    --  -30.00 134.60 -56.90   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0415531131
_diffrn_orient_matrix_UB_12      -0.0024192754
_diffrn_orient_matrix_UB_13      -0.0315701036
_diffrn_orient_matrix_UB_21      -0.0215755905
_diffrn_orient_matrix_UB_22      0.0114282841
_diffrn_orient_matrix_UB_23      0.0230855587
_diffrn_orient_matrix_UB_31      0.0009106449
_diffrn_orient_matrix_UB_32      0.1767741606
_diffrn_orient_matrix_UB_33      -0.0018663766
_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  0.0830
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.162
_diffrn_reflns_Laue_measured_fraction_max 0.136
_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       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            1236
_diffrn_reflns_point_group_measured_fraction_full 0.162
_diffrn_reflns_point_group_measured_fraction_max 0.136
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.117
_diffrn_reflns_theta_min         4.101
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.450
_exptl_absorpt_correction_T_min  0.396
_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    1.628
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     34
_refine_ls_number_reflns         205
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0826
_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^)+(0.1618P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2137
_refine_ls_wR_factor_ref         0.2789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                98
_reflns_number_total             205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02183e3.cif
_cod_data_source_block           etyfum_358
_cod_depositor_comments
'Adding full bibliography for 7133545--7133558.cif.'
_cod_database_code               7133550
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'c12h12n2, c4h4o4'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.961
_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 = 223.0 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
;
_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. Restrained distances
 O2-C7
 1.2 with sigma of 0.02
 C7-O1
 1.3 with sigma of 0.02
 C7-C8
 1.5 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), C5(H5), C4(H4), C2(H2), C8(H8)
3.c Fitted hexagon refined as free rotating group:
 C1(N1,C5,C4,C3,C2)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              29568
_shelx_hkl_checksum              46170
_ins_header
;
TITL ETYFUM_358_final in I2/a 
REM I2/a (#15 with fixed user cell (not necessary: std = user cell)!)
CELL 0.71073  16.891454   3.993045  20.194479  90.0000 115.9006  90.0000
ZERR    3.00   0.049981   0.000381   0.052367   0.0000   0.3696   0.0000
LATT  2
SYMM -x+1/2, y,-z 
SFAC C H N O
UNIT 48.00 48.00 6.00 12.00
SIZE 0.05 0.26 0.34
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 4.233
_oxdiff_exptl_absorpt_empirical_full_min 0.361