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_7133557
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.38(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.808(6)
_cell_length_b                   4.2460(8)
_cell_length_c                   20.027(8)
_cell_measurement_reflns_used    756
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.8890
_cell_measurement_theta_min      2.6480
_cell_volume                     1301.8(9)
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_pressure         1850000
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.293
_diffrn_measured_fraction_theta_max 0.284
_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    -43.00  17.00   1.00   15.00    --   -0.27  67.00 -23.00   60
  2  \w     29.00  57.00   1.00   15.00    --   -0.27 -99.00-150.00   28
  3  \w     -8.00  62.00   1.00   30.00    --   26.72 -67.00  23.00   70
  4  \w      2.00  68.00   1.00   30.00    --   26.72 -81.00-151.00   66
  5  \w    -39.00   9.00   1.00   30.00    --   26.72   0.00-150.00   48
  6  \w    -30.00   4.00   1.00   30.00    --   26.72  97.00 -35.00   34
  7  \w    -22.00  11.00   1.00   30.00    --   26.72  81.00 151.00   33
  8  \w    -38.00  -9.00   1.00   30.00    --  -27.26  77.00 -30.00   29
  9  \w     17.00  50.00   1.00   30.00    --  -27.26-134.00-123.00   33
 10  \w   -121.00 -69.00   1.00   30.00    --  -27.26 178.00 -90.00   52
 11  \w    -27.00  38.00   1.00   30.00    --  -27.26 -39.00-167.00   65
 12  \w    -48.00  31.00   1.00   30.00    --  -27.26  26.00  -7.00   79
 13  \w      5.00  37.00   1.00   30.00    --  -27.26-114.00  44.00   32
 14  \w     -4.00  16.00   1.00   30.00    --  -27.26 -57.00  30.00   20
 15  \w    -17.00  16.00   1.00   30.00    --  -27.26 -67.00  23.00   33
 16  \w    -68.00  11.00   1.00   30.00    --  -27.26  81.00 151.00   79
 17  \w    -11.00  22.00   1.00   30.00    --  -27.26 -81.00-151.00   33
 18  \w    -38.00  -9.00   1.00   15.00    --   -0.27  77.00 -60.00   29
 19  \w    -47.00  -9.00   1.00   15.00    --   -0.27  77.00-180.00   38
 20  \w     -4.00  18.00   1.00   30.00    --   26.72 -57.00  60.00   22
 21  \w    -16.00  17.00   1.00   30.00    --   26.72  67.00 157.00   33
 22  \w    -17.00   4.00   1.00   30.00    --   26.72  57.00-180.00   21
 23  \w      9.00  34.00   1.00   30.00    --   26.72 -77.00  60.00   25
 24  \w    -28.00  44.00   1.00   30.00    --   26.72 -13.00   3.00   72
;
_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      0.0293142000
_diffrn_orient_matrix_UB_12      0.0955796000
_diffrn_orient_matrix_UB_13      0.0286546000
_diffrn_orient_matrix_UB_21      -0.0332915000
_diffrn_orient_matrix_UB_22      0.0306032000
_diffrn_orient_matrix_UB_23      0.0122172000
_diffrn_orient_matrix_UB_31      0.0133172000
_diffrn_orient_matrix_UB_32      -0.1335971000
_diffrn_orient_matrix_UB_33      0.0232376000
_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  0.0880
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.293
_diffrn_reflns_Laue_measured_fraction_max 0.284
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2475
_diffrn_reflns_point_group_measured_fraction_full 0.293
_diffrn_reflns_point_group_measured_fraction_max 0.284
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.665
_diffrn_reflns_theta_min         2.676
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.995
_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    1.532
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0998P)^2^+1.2687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                218
_reflns_number_total             351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02183e3.cif
_cod_data_source_block           etyfum_185
_cod_depositor_comments
'Adding full bibliography for 7133545--7133558.cif.'
_cod_original_cell_volume        1301.8(8)
_cod_database_code               7133557
_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   0.973
_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)
;
_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              85584
_shelx_hkl_checksum              46579
_ins_header
;
TITL ETYFUM_185 in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.808322   4.246006  20.027429  90.0000 114.3839  90.0000
ZERR    3.00   0.005800   0.000847   0.007864   0.0000   0.0474   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 0.04 0.19 0.22
TREF
HKLF 4
END
;
_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 gradually decompressed to 1.85(2) GPa. Daphne oil 7575 was used as hydrostatic medium.'
_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 2.445
_oxdiff_exptl_absorpt_empirical_full_min 0.758