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_7133556
_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                 111.80(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.758(12)
_cell_length_b                   4.5205(17)
_cell_length_c                   19.83(2)
_cell_measurement_reflns_used    488
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.1080
_cell_measurement_theta_min      2.7130
_cell_volume                     1395(2)
_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         790000
_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 0.241
_diffrn_measured_fraction_theta_max 0.238
_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      5.00  63.00   1.00   15.00    --   -0.43-114.00-136.00   58
  2  \w      9.00  38.00   1.00   30.00    --   26.40 -77.00  30.00   29
  3  \w     -6.00  68.00   1.00   30.00    --   26.40 -81.00-151.00   74
  4  \w    -42.00  31.00   1.00   30.00    --   26.40  26.00  -7.00   73
  5  \w     60.00 111.00   1.00   30.00    --   26.40 178.00 -90.00   51
  6  \w     13.00  84.00   1.00   30.00    --   26.40-114.00  44.00   71
  7  \w    -17.00   4.00   1.00   30.00    --   26.40  57.00 120.00   21
  8  \w    -39.00  27.00   1.00   30.00    --   26.40  39.00 -12.00   66
  9  \w    -57.00  22.00   1.00   30.00    --  -27.26  53.00 162.00   79
 10  \w    -38.00  -9.00   1.00   30.00    --  -27.26  77.00 -30.00   29
 11  \w    -27.00  38.00   1.00   30.00    --  -27.26 -39.00  12.00   65
 12  \w    -52.00  27.00   1.00   30.00    --  -27.26  39.00 -12.00   79
 13  \w    -38.00  -9.00   1.00   15.00    --   -0.43  77.00 150.00   29
 14  \w    -37.00  -5.00   1.00   30.00    --   26.40 114.00 136.00   32
 15  \w    -39.00  -6.00   1.00   30.00    --   26.40   0.00-150.00   33
 16  \w     -4.00  16.00   1.00   30.00    --  -27.26 -57.00-150.00   20
 17  \w     17.00  50.00   1.00   30.00    --  -27.26-134.00  56.00   33
;
_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      -0.0292734000
_diffrn_orient_matrix_UB_12      0.0806060000
_diffrn_orient_matrix_UB_13      -0.0294979000
_diffrn_orient_matrix_UB_21      0.0328691000
_diffrn_orient_matrix_UB_22      0.0233063000
_diffrn_orient_matrix_UB_23      -0.0139338000
_diffrn_orient_matrix_UB_31      -0.0120096000
_diffrn_orient_matrix_UB_32      -0.1325857000
_diffrn_orient_matrix_UB_33      -0.0204211000
_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  0.0794
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.241
_diffrn_reflns_Laue_measured_fraction_max 0.238
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            937
_diffrn_reflns_point_group_measured_fraction_full 0.241
_diffrn_reflns_point_group_measured_fraction_max 0.238
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_min         2.729
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_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    1.430
_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         0.201
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0851
_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^)+(0.1660P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2074
_refine_ls_wR_factor_ref         0.2642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                185
_reflns_number_total             308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02183e3.cif
_cod_data_source_block           etyfum_079
_cod_depositor_comments
'Adding full bibliography for 7133545--7133558.cif.'
_cod_original_cell_volume        1394(2)
_cod_database_code               7133556
_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   0.978
_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              4283
_shelx_hkl_checksum              54781
_ins_header
;
TITL ETYFUM_079 in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.757707   4.520527  19.825844  90.0000 111.7974  90.0000
ZERR    4.00   0.012437   0.001740   0.020242   0.0000   0.1079   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 0.04 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 3.00(2) and then decompressed in steps to 0.79(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 3.492
_oxdiff_exptl_absorpt_empirical_full_min 0.390