# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ETYFUM
_database_code_depnum_ccdc_archive 'CCDC 2340674'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-06-12 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
# start Validation Reply Form
_vrf_PLAT927_ETYFUM              
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0773 Check 
RESPONSE: 'Difference due to non-sperical refinement of the structure'
;
_vrf_PLAT355_ETYFUM              
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1A      .       1.08 Ang.  
RESPONSE: 'Chcekcif reference default value of the 
O-H bond from Shelxl, and in this case shelxl was not used for the refinement.
Instead, non-spherical refinement of hydrogen atoms was performed leading to longer
refined value of the O-H bond lentght.'
;
_vrf_PLAT926_ETYFUM              
;
PROBLEM: Reported and Calculated   R1 Differ by .........    -0.0296 Check 
RESPONSE: 'Difference due to non-sperical refinement of the structure'
;
_vrf_PLAT928_ETYFUM              
;
PROBLEM: Reported and Calculated    S value   Differ by .     -1.609 Check 
RESPONSE: 'Difference due to non-sperical refinement of the structure'
;
# end Validation Reply Form
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.316
_chemical_oxdiff_formula         'C12 H12 N2, C4 H4 O4'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y,-z
3 -x,-y,-z
4 x-1/2,-y,z
5 x+1/2,y+1/2,z+1/2
6 -x+1,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z+1/2
8 x,-y+1/2,z+1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   16.6937(2)
_cell_length_b                   4.8165(1)
_cell_length_c                   19.6871(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.083(2)
_cell_angle_gamma                90
_cell_volume                     1495.96(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.2350
_cell_measurement_theta_min      2.9980
_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
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -2 0.1155
-8 0 -6 0.0559
8 0 6 0.1037
1 3 -1 0.1218
-7 1 11 0.0330
7 -1 -10 0.0547
-2 -3 2 0.3232

_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.093
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.2232 3.0713 -2.1527 0.0473 0.1882 0.9810
-7.5922 0.2403 -5.6399 0.2337 0.9719 0.0279
7.5011 -0.4059 5.6814 -0.2331 -0.9690 -0.0815
1.3905 3.0943 -1.2798 0.0181 -0.0024 0.9998
-7.4375 0.5531 11.2819 -0.9647 0.2304 0.0624
7.3616 -0.6011 -10.3598 0.8998 -0.2644 -0.0819
-1.7241 -3.0727 1.7838 -0.0612 0.0128 -0.9980

_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.23 -37.00   0.00   99
  2  ω   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00 -60.00  101
  3  ω      6.00  97.00   1.00    2.00    --   41.23-125.00 -90.00   91
  4  ω     59.00 158.00   1.00    3.00    --  112.00  15.00-180.00   99
  5  ω     36.00 106.00   1.00    3.00    --  112.00 -77.00  90.00   70
  6  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00 -30.00   31
  7  ω     86.00 158.00   1.00    3.00    --  112.00  45.00  60.00   72
  8  ω     59.00 158.00   1.00    3.00    --  112.00  15.00  90.00   99
  9  ω     36.00 109.00   1.00    3.00    --  112.00-111.00-180.00   73
 10  ω     84.00 158.00   1.00    3.00    --  112.00  30.00 -30.00   74
 11  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00-150.00   31
 12  ω     86.00 158.00   1.00    3.00    --  112.00  45.00 -90.00   72
 13  ω     36.00 106.00   1.00    3.00    --  112.00 -77.00-180.00   70
 14  ω    -42.00  33.00   1.00    2.00    --  -41.23  37.00 -30.00   75
 15  ω   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00  90.00  101
 16  ω   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00-180.00  101
 17  ω    -33.00  42.00   1.00    2.00    --   41.23 -37.00  30.00   75
 18  ω     83.00 158.00   1.00    3.00    --  112.00  61.00-180.00   75
 19  ω     83.00 158.00   1.00    3.00    --  112.00  61.00-150.00   75
 20  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00  30.00   31
 21  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00-120.00   31
 22  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00 -90.00   31
 23  ω     82.00 158.00   1.00    3.00    --  112.00  77.00 -30.00   76
 24  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00   0.00   31
 25  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00 -60.00   31
 26  ω    -26.00  39.00   1.00    2.00    --  -41.23  19.00  30.00   65
 27  ω   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00   0.00  101
 28  ω   -114.00 -13.00   1.00    2.00    --  -41.23 -57.00-120.00  101
 29  ω      6.00  97.00   1.00    2.00    --   41.23-125.00-180.00   91
 30  ω     36.00 109.00   1.00    3.00    --  112.00-111.00  90.00   73
 31  ω     83.00 158.00   1.00    3.00    --  112.00  61.00  90.00   75
 32  ω     36.00 109.00   1.00    3.00    --  112.00-111.00   0.00   73
 33  ω     82.00 158.00   1.00    3.00    --  112.00  77.00   0.00   76
 34  ω     40.00  71.00   1.00    3.00    --  112.00 -61.00-180.00   31
 35  ω     83.00 158.00   1.00    3.00    --  112.00  61.00 150.00   75
 36  ω     83.00 158.00   1.00    3.00    --  112.00  61.00-120.00   75
 37  ω     82.00 158.00   1.00    3.00    --  112.00  77.00 -90.00   76
 38  ω    -99.00  -8.00   1.00    2.00    --  -41.23 128.00-111.00   91
 39  ω   -116.00 -17.00   1.00    2.00    --  -41.23 -37.00 -60.00   99
 40  ω     17.00 116.00   1.00    2.00    --   41.23  37.00-120.00   99
 41  ω    -39.00  26.00   1.00    2.00    --   41.23 -19.00-180.00   65
 42  ω     82.00 158.00   1.00    3.00    --  112.00  77.00 -60.00   76
 43  ω     36.00  97.00   1.00    3.00    --  112.00-111.00 -60.00   61
 44  ω     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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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)
_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)'
_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+0.001xFc²λ³/sin(2θ)]^-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_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.0766
_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/[σ²(Fo²)+(0.0264P)²+0.1012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0517
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
C1 C 0.15778(4) 0.41509(15) 0.41465(3) 0.04321(18) Uani 1.000000 .
C2 C 0.13011(4) 0.21666(15) 0.45292(3) 0.04320(18) Uani 1.000000 .
C3 C 0.04569(4) 0.13494(13) 0.42889(3) 0.03426(16) Uani 1.000000 .
C4 C -0.00742(4) 0.25777(14) 0.36656(3) 0.03931(17) Uani 1.000000 .
C5 C 0.02536(4) 0.45334(14) 0.33119(3) 0.03973(17) Uani 1.000000 .
C6 C 0.01259(5) -0.07077(15) 0.47051(4) 0.04155(17) Uani 1.000000 .
N1 N 0.10646(3) 0.53080(12) 0.35483(3) 0.03776(15) Uani 1.000000 .
C7 C 0.24097(4) 0.98122(14) 0.31998(3) 0.03648(16) Uani 1.000000 .
C8 C 0.27168(4) 1.20208(14) 0.28171(3) 0.03950(16) Uani 1.000000 .
O1 O 0.16405(3) 0.89669(11) 0.28659(3) 0.04614(15) Uani 1.000000 .
O2 O 0.28567(3) 0.89200(11) 0.37768(2) 0.05338(17) Uani 1.000000 .
H1 H 0.2237(5) 0.487(2) 0.4317(5) 0.074(3) Uani 1.000000 .
H5 H -0.0142(5) 0.553(2) 0.2818(4) 0.070(3) Uani 1.000000 .
H4 H -0.0739(5) 0.204(2) 0.3457(4) 0.070(3) Uani 1.000000 .
H2 H 0.1742(5) 0.125(2) 0.5013(4) 0.075(3) Uani 1.000000 .
H6A H 0.0625(7) -0.225(2) 0.4954(5) 0.082(3) Uani 1.000000 .
H6B H -0.0409(7) -0.183(2) 0.4345(5) 0.085(3) Uani 1.000000 .
H8 H 0.3344(5) 1.277(2) 0.3101(4) 0.083(3) Uani 1.000000 .
H1A H 0.1439(6) 0.746(2) 0.3181(5) 0.063(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3863(9) . ?
C1 N1 1.3312(8) . ?
C1 H1 1.097(7) . ?
C2 C3 1.3888(8) . ?
C2 H2 1.088(8) . ?
C3 C4 1.3894(8) . ?
C3 C6 1.5016(8) . ?
C4 C5 1.3859(8) . ?
C4 H4 1.082(7) . ?
C5 N1 1.3330(7) . ?
C5 H5 1.090(7) . ?
C6 C6 1.5194(13) 3_556 ?
C6 H6A 1.105(10) . ?
C6 H6B 1.085(9) . ?
C7 C8 1.4882(8) . ?
C7 O1 1.3018(7) . ?
C7 O2 1.2156(7) . ?
C8 C8 1.3058(12) 7_575 ?
C8 H8 1.076(8) . ?
O1 H1A 1.079(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.48(6) . . ?
H1 C1 C2 122.1(5) . . ?
H1 C1 N1 115.5(5) . . ?
C3 C2 C1 119.44(6) . . ?
H2 C2 C1 120.2(5) . . ?
H2 C2 C3 120.3(5) . . ?
C4 C3 C2 117.63(5) . . ?
C6 C3 C2 120.97(6) . . ?
C6 C3 C4 121.36(6) . . ?
C5 C4 C3 119.36(6) . . ?
H4 C4 C3 120.9(4) . . ?
H4 C4 C5 119.8(4) . . ?
N1 C5 C4 122.52(6) . . ?
H5 C5 C4 121.5(4) . . ?
H5 C5 N1 116.0(4) . . ?
C6 C6 C3 111.35(7) 3_556 . ?
H6A C6 C3 109.2(4) . . ?
H6B C6 C3 110.0(5) . . ?
H6B C6 H6A 107.1(8) . . ?
C5 N1 C1 118.56(5) . . ?
O1 C7 C8 114.46(5) . . ?
O2 C7 C8 121.19(5) . . ?
O2 C7 O1 124.35(6) . . ?
C8 C8 C7 124.18(8) 7_575 . ?
H8 C8 C7 114.6(4) . . ?
H1A O1 C7 111.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.21(8) . . . . ?
C1 C2 C3 C6 -177.49(6) . . . . ?
C1 N1 C5 C4 0.11(7) . . . . ?
C2 C3 C4 C5 0.19(7) . . . . ?
C2 C3 C6 C6 84.86(8) . . . 3_556 ?
C3 C4 C5 N1 -0.37(7) . . . . ?
C3 C6 C6 C3 -180.00(8) . . 3_556 3_556 ?
C7 C8 C8 C7 180.00(9) . . 7_575 7_575 ?



_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_008
_database_code_depnum_ccdc_archive 'CCDC 2340675'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_008          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT029_etyfum_008          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.239 Why?  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT088_etyfum_008          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.29 Note  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT149_etyfum_008          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.30 Degree
RESPONSE: "Quality of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT201_etyfum_008          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT340_etyfum_008          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............       0.04 Ang.  
RESPONSE: "Quality of structural model affected by poor quality and low number 
of experimental data"
;
_vrf_PLAT911_etyfum_008          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        900 Report
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4H4O4, N2C12H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.68(4)
_cell_length_b                   4.7884(10)
_cell_length_c                   19.65(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.1(3)
_cell_angle_gamma                90
_cell_volume                     1483(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    469
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.8810
_cell_measurement_theta_min      2.7320
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.453
_exptl_absorpt_correction_T_min  0.403
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
17 -5 -12 0.1090
-13 -5 15 0.1042
-18 5 13 0.1410
8 6 -11 0.0709
17 2 14 0.0100
-20 -3 -15 0.0100

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_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)      0.404     0.454
         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 = 150.0 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

    Non-absorbing pressure medium
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
16.5263 -4.9993 -11.5242 -0.0273 -0.9790 0.2019
-13.3100 -4.7778 15.2382 -0.0038 -0.2745 -0.9616
-17.8341 4.5583 13.0022 0.0270 0.9555 -0.2938
7.5012 5.9434 -10.7872 0.0117 0.5472 0.8369
17.2331 1.8980 14.4128 -1.0933 0.1432 0.0126
-19.9931 -2.8612 -14.7536 1.2136 -0.2308 -0.1155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.1402
_diffrn_reflns_Laue_measured_fraction_full 0.239
_diffrn_reflns_Laue_measured_fraction_max 0.203
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1576
_diffrn_reflns_point_group_measured_fraction_full 0.239
_diffrn_reflns_point_group_measured_fraction_max 0.203
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.021
_diffrn_reflns_theta_min         2.791
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         80000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.239
_diffrn_measured_fraction_theta_max 0.203
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00   5.00   1.00   35.00    --   27.05   0.00-150.00   40
  2  ω    -36.00 -10.00   1.00   35.00    --   27.05 114.00 136.00   26
  3  ω    -24.00  35.00   1.00   35.00    --   27.05   0.00   0.00   59
  4  ω     15.00  60.00   1.00   35.00    --   27.05 -77.00-150.00   45
  5  ω    -28.00  -1.00   1.00   35.00    --   27.05  97.00 -35.00   27
  6  ω    -91.00 -22.00   1.00   35.00    --  -27.99 134.00 -56.00   69
  7  ω    -52.00  17.00   1.00   35.00    --  -27.99  53.00 162.00   69
  8  ω    -52.00  17.00   1.00   35.00    --  -27.99  53.00 -17.00   69
  9  ω    -22.00  32.00   1.00   35.00    --  -27.99 -39.00-167.00   54
 10  ω    -26.00  43.00   1.00   35.00    --  -27.99 -26.00   7.00   69
 11  ω    -12.00  13.00   1.00   35.00    --  -27.99 -67.00-157.00   25
 12  ω    -12.00  13.00   1.00   35.00    --  -27.99 -67.00  23.00   25
 13  ω     -4.00  57.00   1.00   35.00    --   27.05 -37.00-180.00   61
 14  ω     70.00 102.00   1.00   35.00    --   27.05 178.00 -90.00   32
 15  ω      3.00  63.00   1.00   35.00    --   27.05 -81.00  29.00   60
 16  ω    -17.00  16.00   1.00   35.00    --  -27.99 -53.00  17.00   33
 17  ω    -11.00  37.00   1.00   35.00    --  -27.99 -37.00-180.00   48
 18  ω    -22.00   3.00   1.00   35.00    --  -27.99 -19.00-180.00   25
 19  ω     10.00  35.00   1.00   35.00    --  -27.99-114.00-136.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321118000
_diffrn_orient_matrix_UB_12      -0.0205789000
_diffrn_orient_matrix_UB_13      -0.0347513000
_diffrn_orient_matrix_UB_21      -0.0138968000
_diffrn_orient_matrix_UB_22      0.1273528000
_diffrn_orient_matrix_UB_23      0.0097784000
_diffrn_orient_matrix_UB_31      0.0153219000
_diffrn_orient_matrix_UB_32      0.0724898000
_diffrn_orient_matrix_UB_33      -0.0269918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 0.08(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                135
_reflns_number_total             328
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2118
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.020
_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/[σ²(Fo²)+(0.0481P)²+2.6463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1676
_refine_special_details          ?
_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
 C8-C7
 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), C2(H2), C4(H4), C5(H5), C8(H8)
3.c Idealised tetrahedral OH refined with riding coordinates:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1567(16) 0.415(2) 0.4136(14) 0.045(4) Uiso 1 1 d . . . . .
H1 H 0.2135 0.4678 0.4300 0.054 Uiso 1 1 calc R U . . .
C2 C 0.1299(19) 0.212(2) 0.4536(18) 0.060(4) Uiso 1 1 d . . . . .
H2 H 0.1674 0.1334 0.4952 0.072 Uiso 1 1 calc R U . . .
C3 C 0.045(2) 0.134(2) 0.4280(19) 0.044(4) Uiso 1 1 d . . . . .
C4 C -0.0088(18) 0.254(2) 0.3657(17) 0.040(4) Uiso 1 1 d . . . . .
H4 H -0.0657 0.2030 0.3481 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0235(19) 0.454(2) 0.3294(18) 0.059(4) Uiso 1 1 d . . . . .
H5 H -0.0123 0.5335 0.2872 0.070 Uiso 1 1 calc R U . . .
C6 C 0.0122(14) -0.0725(17) 0.4701(13) 0.041(3) Uiso 1 1 d . . . . .
H6A H 0.0555 -0.2117 0.4910 0.049 Uiso 1 1 calc R U . . .
H6B H -0.0371 -0.1674 0.4379 0.049 Uiso 1 1 calc R U . . .
N1 N 0.1072(16) 0.535(2) 0.3551(14) 0.048(4) Uiso 1 1 d . . . . .
C7 C 0.237(4) 0.976(3) 0.320(3) 0.076(7) Uiso 1 1 d D . . . .
C8 C 0.275(2) 1.204(3) 0.2844(18) 0.047(4) Uiso 1 1 d D . . . .
H8 H 0.3288 1.2781 0.3073 0.056 Uiso 1 1 calc R U . . .
O1 O 0.1646(16) 0.9004(19) 0.2853(15) 0.065(3) Uiso 1 1 d . . . . .
H1A H 0.1484 0.7846 0.3086 0.097 Uiso 1 1 calc R U . . .
O2 O 0.2859(19) 0.894(2) 0.3762(16) 0.070(4) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.413(16) . ?
C1 N1 1.31(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.39(4) . ?
C3 C4 1.38(5) . ?
C3 C6 1.501(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(17) . ?
C5 H5 0.9300 . ?
C5 N1 1.38(4) . ?
C6 C6 1.53(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.538(15) . ?
C7 O1 1.24(7) . ?
C7 O2 1.20(8) . ?
C8 C8 1.41(7) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 117.7 . . ?
N1 C1 H1 117.7 . . ?
N1 C1 C2 125(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 C6 119(3) . . ?
C4 C3 C2 119.8(16) . . ?
C4 C3 C6 121(3) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.4 . . ?
N1 C5 C4 121(3) . . ?
N1 C5 H5 119.4 . . ?
C3 C6 C6 111.1(10) . 5_556 ?
C3 C6 H6A 109.4 . . ?
C3 C6 H6B 109.4 . . ?
C6 C6 H6A 109.4 5_556 . ?
C6 C6 H6B 109.4 5_556 . ?
H6A C6 H6B 108.0 . . ?
C1 N1 C5 118.2(16) . . ?
O1 C7 C8 115(5) . . ?
O2 C7 C8 113(4) . . ?
O2 C7 O1 131.0(18) . . ?
C7 C8 H8 121.5 . . ?
C8 C8 C7 117(4) 7_575 . ?
C8 C8 H8 121.5 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.4(19) . . . . ?
C1 C2 C3 C6 -177.5(10) . . . . ?
C2 C1 N1 C5 -2(2) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C2 C3 C6 C6 84(3) . . . 5_556 ?
C3 C4 C5 N1 -1(2) . . . . ?
C4 C3 C6 C6 -94(3) . . . 5_556 ?
C4 C5 N1 C1 1.6(17) . . . . ?
C6 C3 C4 C5 177.6(9) . . . . ?
N1 C1 C2 C3 1(2) . . . . ?
O1 C7 C8 C8 -2.0(19) . . . 7_575 ?
O2 C7 C8 C8 175.0(18) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_005_final in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  19.647363   4.788362  16.678023  90.0000 109.0649  90.0000
ZERR    4.00   0.048379   0.000954   0.037034   0.0000   0.2910   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 0.22 0.33
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 0.08(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 1.875
_oxdiff_exptl_absorpt_empirical_full_min 0.457
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_035
_database_code_depnum_ccdc_archive 'CCDC 2340678'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_035          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT029_etyfum_035          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.245 Why?  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT088_etyfum_035          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.15 Note  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT149_etyfum_035          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.12 Degree
RESPONSE: "Quality of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT201_etyfum_035          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT340_etyfum_035          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02625 Ang.  
RESPONSE: "Quality of structural model affected by poor quality and low number 
of experimental data"
;
_vrf_PLAT911_etyfum_035          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        857 Report
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N2, C4 H4 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.686(12)
_cell_length_b                   4.6593(13)
_cell_length_c                   19.75(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.45(12)
_cell_angle_gamma                90
_cell_volume                     1439(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    369
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.1110
_cell_measurement_theta_min      2.7080
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.996
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
17 -4 1 0.0328
24 0 -10 0.0531
10 5 -14 0.0560
-14 5 -4 0.1520
-23 -1 11 0.1471
-14 -5 15 0.1338
0 -3 -19 0.0260
0 3 18 0.0090

_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.037
_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)
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
17.3995 -3.9558 0.7047 0.2260 -0.7728 0.5930
23.5038 0.4018 -9.9934 0.2799 -0.9461 -0.1630
10.3368 5.3478 -14.2464 0.1003 -0.3280 -0.9393
-13.9907 4.7371 -3.5317 -0.1886 0.6479 -0.7380
-23.2739 -0.9474 10.9426 -0.2748 0.9275 0.2536
-13.9883 -4.7980 14.6326 -0.1465 0.4854 0.8619
0.0429 -2.7640 -19.4862 -0.8232 -0.2356 0.0537
0.1675 2.5821 18.3442 0.7790 0.2134 -0.0473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 0.245
_diffrn_reflns_Laue_measured_fraction_max 0.225
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1080
_diffrn_reflns_point_group_measured_fraction_full 0.245
_diffrn_reflns_point_group_measured_fraction_max 0.225
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.239
_diffrn_reflns_theta_min         2.761
_diffrn_ambient_temperature      298.00
_diffrn_ambient_pressure         350000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.245
_diffrn_measured_fraction_theta_max 0.225
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  42.00   1.00   20.00    --   -0.43 -57.00-150.00   46
  2  ω    -32.00  27.00   1.00   40.00    --   28.43  39.00 -12.00   59
  3  ω      9.00  38.00   1.00   40.00    --   28.43 -77.00  30.00   29
  4  ω    -39.00   9.00   1.00   40.00    --   28.43   0.00-150.00   48
  5  ω     68.00 111.00   1.00   40.00    --   28.43 178.00  90.00   43
  6  ω    -17.00  12.00   1.00   40.00    --  -29.29 -67.00-157.00   29
  7  ω    -62.00  17.00   1.00   40.00    --  -29.29  67.00 157.00   79
  8  ω    -16.00  36.00   1.00   40.00    --  -29.29 -37.00-180.00   52
  9  ω    -39.00   9.00   1.00   40.00    --  -29.29   0.00-150.00   48
 10  ω    -27.00  31.00   1.00   40.00    --  -29.29 -39.00  12.00   58
 11  ω    -84.00  -5.00   1.00   40.00    --  -29.29 114.00 136.00   79
 12  ω    -38.00  -9.00   1.00   20.00    --   -0.43  77.00 -60.00   29
 13  ω     29.00  63.00   1.00   40.00    --   28.43 -99.00-120.00   34
 14  ω      5.00  33.00   1.00   40.00    --  -29.29-114.00  44.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0252533000
_diffrn_orient_matrix_UB_12      0.0599734000
_diffrn_orient_matrix_UB_13      0.0337929000
_diffrn_orient_matrix_UB_21      -0.0375788000
_diffrn_orient_matrix_UB_22      0.0314214000
_diffrn_orient_matrix_UB_23      0.0075515000
_diffrn_orient_matrix_UB_31      0.0024423000
_diffrn_orient_matrix_UB_32      -0.1362195000
_diffrn_orient_matrix_UB_33      0.0165733000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 0.35(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                180
_reflns_number_total             329
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.004
_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/[σ²(Fo²)+(0.1591P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2671
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1552(12) 0.399(3) 0.4111(15) 0.043(4) Uiso 1 1 d . . . . .
H1 H 0.2135 0.4378 0.4261 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1308(9) 0.201(2) 0.4521(11) 0.051(4) Uiso 1 1 d . . . . .
H2 H 0.1691 0.1244 0.4945 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0415(11) 0.122(3) 0.4244(13) 0.037(3) Uiso 1 1 d . . . . .
C4 C -0.0054(11) 0.261(2) 0.3691(12) 0.042(4) Uiso 1 1 d . . . . .
H4 H -0.0643 0.2312 0.3530 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0266(9) 0.451(2) 0.3323(12) 0.046(4) Uiso 1 1 d . . . . .
H5 H -0.0097 0.5289 0.2891 0.055 Uiso 1 1 calc R U . . .
C6 C 0.0117(7) -0.079(2) 0.4714(9) 0.038(3) Uiso 1 1 d . . . . .
H6A H -0.0377 -0.1858 0.4411 0.045 Uiso 1 1 calc R U . . .
H6B H 0.0568 -0.2155 0.4946 0.045 Uiso 1 1 calc R U . . .
N1 N 0.1105(10) 0.530(2) 0.3575(12) 0.040(3) Uiso 1 1 d . . . . .
C7 C 0.2431(14) 0.972(3) 0.3234(16) 0.049(4) Uiso 1 1 d . . . . .
C8 C 0.2723(13) 1.202(3) 0.2807(14) 0.042(3) Uiso 1 1 d . . . . .
H8 H 0.3273 1.2750 0.3019 0.051 Uiso 1 1 calc R U . . .
O1 O 0.1628(6) 0.8953(15) 0.2856(7) 0.056(3) Uiso 1 1 d . . . . .
H1A H 0.1461 0.7801 0.3092 0.083 Uiso 1 1 calc R U . . .
O2 O 0.2888(8) 0.883(2) 0.3797(10) 0.063(3) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.379(17) . ?
C1 N1 1.22(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.44(2) . ?
C3 C4 1.28(3) . ?
C3 C6 1.520(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(15) . ?
C5 H5 0.9300 . ?
C5 N1 1.361(16) . ?
C6 C6 1.51(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.541(18) . ?
C7 O1 1.34(2) . ?
C7 O2 1.18(3) . ?
C8 C8 1.27(5) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 115.6 . . ?
N1 C1 H1 115.6 . . ?
N1 C1 C2 128.7(19) . . ?
C1 C2 H2 122.4 . . ?
C1 C2 C3 115.2(17) . . ?
C3 C2 H2 122.4 . . ?
C2 C3 C6 116.2(17) . . ?
C4 C3 C2 116.0(13) . . ?
C4 C3 C6 127.0(16) . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.1(18) . . ?
C5 C4 H4 118.4 . . ?
C4 C5 H5 119.2 . . ?
N1 C5 C4 121.5(18) . . ?
N1 C5 H5 119.2 . . ?
C3 C6 H6A 109.1 . . ?
C3 C6 H6B 109.1 . . ?
C6 C6 C3 112.5(11) 5_556 . ?
C6 C6 H6A 109.1 5_556 . ?
C6 C6 H6B 109.1 5_556 . ?
H6A C6 H6B 107.8 . . ?
C1 N1 C5 114.9(15) . . ?
O1 C7 C8 109(2) . . ?
O2 C7 C8 122(2) . . ?
O2 C7 O1 128.4(15) . . ?
C7 C8 H8 117.3 . . ?
C8 C8 C7 125(3) 7_575 . ?
C8 C8 H8 117.3 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -6(2) . . . . ?
C1 C2 C3 C6 -175.7(11) . . . . ?
C2 C1 N1 C5 -6(3) . . . . ?
C2 C3 C4 C5 7(3) . . . . ?
C2 C3 C6 C6 84.8(16) . . . 5_556 ?
C3 C4 C5 N1 -8(3) . . . . ?
C4 C3 C6 C6 -84(3) . . . 5_556 ?
C4 C5 N1 C1 6(2) . . . . ?
C6 C3 C4 C5 175.9(10) . . . . ?
N1 C1 C2 C3 6(3) . . . . ?
O1 C7 C8 C8 -1(3) . . . 7_575 ?
O2 C7 C8 C8 177(2) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_035 in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.686325   4.659302  19.754987  90.0000 110.4533  90.0000
ZERR    4.00   0.011809   0.001322   0.026015   0.0000   0.1204   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(3)GPa and then decompressed in steps to 0.35(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 2.408
_oxdiff_exptl_absorpt_empirical_full_min 0.423
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_125
_database_code_depnum_ccdc_archive 'CCDC 2340677'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_125          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_125          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.281 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT088_etyfum_125          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.54 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT149_etyfum_125          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter'
;
_vrf_PLAT201_etyfum_125          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_125          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01413 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_125          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        806 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N2,C4 H4 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.758(8)
_cell_length_b                   4.3755(10)
_cell_length_c                   19.955(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.05(6)
_cell_angle_gamma                90
_cell_volume                     1346.4(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    645
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.4700
_cell_measurement_theta_min      2.6580
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.108
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-20 -3 3 0.0328
-23 1 16 0.0531
-7 5 18 0.0560
17 4 1 0.1520
22 -1 -17 0.1471
11 -4 -19 0.1338
2 -3 16 0.0260
-3 3 -15 0.0090

_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.037
_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)
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-19.6594 -3.1231 3.2768 0.2260 -0.7728 0.5930
-22.9102 0.7267 16.2663 0.2799 -0.9461 -0.1630
-6.7937 4.7708 17.8102 0.1003 -0.3280 -0.9393
16.7957 3.8510 0.5725 -0.1886 0.6479 -0.7380
22.3373 -1.1926 -17.2397 -0.2748 0.9275 0.2536
10.7416 -4.3567 -19.0757 -0.1465 0.4854 0.8619
2.4337 -3.2444 16.1945 -0.8232 -0.2356 0.0537
-2.5161 3.0420 -15.1886 0.7790 0.2134 -0.0473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.281
_diffrn_reflns_Laue_measured_fraction_max 0.270
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2212
_diffrn_reflns_point_group_measured_fraction_full 0.281
_diffrn_reflns_point_group_measured_fraction_max 0.270
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.698
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         1250000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.281
_diffrn_measured_fraction_theta_max 0.270
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  39.00   1.00   30.00    --   26.40   0.00-180.00   73
  2  ω      9.00  65.00   1.00   30.00    --   26.40 -77.00-150.00   56
  3  ω    -51.00 -17.00   1.00   30.00    --   26.40 134.00 123.00   34
  4  ω    -34.00  39.00   1.00   30.00    --   26.40   0.00   0.00   73
  5  ω     69.00 111.00   1.00   30.00    --   26.40 178.00  90.00   42
  6  ω     59.00 111.00   1.00   30.00    --   26.40 178.00 -90.00   52
  7  ω     -4.00  29.00   1.00   30.00    --  -27.26 -97.00  35.00   33
  8  ω    -27.00  38.00   1.00   30.00    --  -27.26 -39.00  12.00   65
  9  ω   -121.00 -69.00   1.00   30.00    --  -27.26 178.00 -90.00   52
 10  ω    -16.00  49.00   1.00   30.00    --  -27.26 -37.00-180.00   65
 11  ω    -48.00  31.00   1.00   30.00    --  -27.26  26.00  -7.00   79
 12  ω    -52.00  27.00   1.00   30.00    --  -27.26  39.00 167.00   79
 13  ω    -17.00  16.00   1.00   30.00    --  -27.26 -67.00-157.00   33
 14  ω    -19.00  16.00   1.00   30.00    --   26.40  53.00 -17.00   35
 15  ω      9.00  38.00   1.00   30.00    --   26.40 -77.00  30.00   29
 16  ω    -35.00 -15.00   1.00   30.00    --   26.40  37.00   0.00   20
 17  ω    -17.00   4.00   1.00   30.00    --   26.40  57.00 150.00   21
 18  ω     -4.00  16.00   1.00   30.00    --  -27.26 -57.00  30.00   20
 19  ω     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       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0300612000
_diffrn_orient_matrix_UB_12      0.0864572000
_diffrn_orient_matrix_UB_13      -0.0289922000
_diffrn_orient_matrix_UB_21      0.0324802000
_diffrn_orient_matrix_UB_22      0.0286278000
_diffrn_orient_matrix_UB_23      -0.0136947000
_diffrn_orient_matrix_UB_31      -0.0124972000
_diffrn_orient_matrix_UB_32      -0.1339163000
_diffrn_orient_matrix_UB_33      -0.0216367000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 1.25(2) GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                228
_reflns_number_total             347
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.058
_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/[σ²(Fo²)+(0.1124P)²+1.7845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1918
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1604(7) 0.3825(17) 0.4151(6) 0.033(2) Uiso 1 1 d . . . . .
H1 H 0.2189 0.4327 0.4327 0.040 Uiso 1 1 calc R U . . .
C2 C 0.1324(6) 0.1788(15) 0.4541(5) 0.032(2) Uiso 1 1 d . . . . .
H2 H 0.1716 0.0874 0.4962 0.038 Uiso 1 1 calc R U . . .
C3 C 0.0447(7) 0.1139(17) 0.4290(6) 0.026(2) Uiso 1 1 d . . . . .
C4 C -0.0111(7) 0.2460(19) 0.3645(6) 0.032(2) Uiso 1 1 d . . . . .
H4 H -0.0701 0.2026 0.3460 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0223(6) 0.4419(16) 0.3284(5) 0.033(2) Uiso 1 1 d . . . . .
H5 H -0.0152 0.5301 0.2851 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0110(5) -0.0918(14) 0.4726(5) 0.028(2) Uiso 1 1 d . . . . .
H6A H 0.0546 -0.2437 0.4979 0.034 Uiso 1 1 calc R U . . .
H6B H -0.0404 -0.1978 0.4401 0.034 Uiso 1 1 calc R U . . .
N1 N 0.1064(5) 0.5108(14) 0.3528(5) 0.033(2) Uiso 1 1 d . . . . .
C7 C 0.2424(7) 0.9657(17) 0.3201(6) 0.028(2) Uiso 1 1 d . . . . .
C8 C 0.2726(7) 1.1966(18) 0.2822(6) 0.030(2) Uiso 1 1 d . . . . .
H8 H 0.3285 1.2722 0.3062 0.036 Uiso 1 1 calc R U . . .
O1 O 0.1627(4) 0.8882(11) 0.2865(4) 0.0392(15) Uiso 1 1 d . . . . .
H1A H 0.1469 0.7887 0.3139 0.059 Uiso 1 1 calc R U . . .
O2 O 0.2914(5) 0.8662(13) 0.3806(4) 0.0439(17) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.380(9) . ?
C1 N1 1.341(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(12) . ?
C3 C4 1.388(15) . ?
C3 C6 1.507(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(10) . ?
C5 H5 0.9300 . ?
C5 N1 1.333(10) . ?
C6 C6 1.513(13) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.465(10) . ?
C7 O1 1.284(12) . ?
C7 O2 1.243(13) . ?
C8 C8 1.298(19) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(11) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(9) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 118.9(8) . . ?
C2 C3 C6 120.0(9) . . ?
C4 C3 C6 121.1(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(10) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 118.7 . . ?
N1 C5 C4 122.7(9) . . ?
N1 C5 H5 118.7 . . ?
C3 C6 C6 110.6(7) . 5_556 ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C6 C6 H6A 109.5 5_556 . ?
C6 C6 H6B 109.5 5_556 . ?
H6A C6 H6B 108.1 . . ?
C5 N1 C1 118.5(8) . . ?
O1 C7 C8 114.3(9) . . ?
O2 C7 C8 120.8(10) . . ?
O2 C7 O1 124.9(8) . . ?
C7 C8 H8 117.5 . . ?
C8 C8 C7 125.0(14) 7_575 . ?
C8 C8 H8 117.5 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 2.5(12) . . . . ?
C1 C2 C3 C6 -176.1(6) . . . . ?
C2 C1 N1 C5 1.0(13) . . . . ?
C2 C3 C4 C5 -1.4(14) . . . . ?
C2 C3 C6 C6 88.5(10) . . . 5_556 ?
C3 C4 C5 N1 0.0(12) . . . . ?
C4 C3 C6 C6 -90.1(13) . . . 5_556 ?
C4 C5 N1 C1 0.2(12) . . . . ?
C6 C3 C4 C5 177.2(6) . . . . ?
N1 C1 C2 C3 -2.4(12) . . . . ?
O1 C7 C8 C8 -5.0(12) . . . 7_575 ?
O2 C7 C8 C8 176.8(10) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_122 in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.758415   4.375511  19.954644  90.0000 113.0476  90.0000
ZERR    3.00   0.007553   0.001003   0.010492   0.0000   0.0621   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 1.25(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 8.168
_oxdiff_exptl_absorpt_empirical_full_min 0.633
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_088
_database_code_depnum_ccdc_archive 'CCDC 2340676'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-06-12 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
# start Validation Reply Form
_vrf_ATOM007_etyfum_088          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_088          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.314 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT149_etyfum_088          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.18 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter'
;
_vrf_PLAT201_etyfum_088          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_088          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02875 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_088          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        829 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4O4H4, N2C12H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.72(2)
_cell_length_b                   4.4815(7)
_cell_length_c                   19.84(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.79(18)
_cell_angle_gamma                90
_cell_volume                     1380(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    624
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.6700
_cell_measurement_theta_min      2.7060
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.968
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 5 -18 0.1090
-15 5 14 0.1042
-13 -4 19 0.1410
11 -6 -8 0.0709
-15 -2 -16 0.0100
15 3 18 0.0100

_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
_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
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
11.7557 4.5908 -17.5773 -0.0273 -0.9790 0.2019
-15.0656 4.5607 13.7321 -0.0038 -0.2745 -0.9616
-13.2179 -4.1694 18.9279 0.0270 0.9555 -0.2938
10.5575 -5.6194 -7.5824 0.0117 0.5472 0.8369
-14.6205 -1.8307 -15.8606 -1.0933 0.1432 0.0126
15.0136 2.7448 18.4725 1.2136 -0.2308 -0.1155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  79.00   1.00   35.00    --   27.05-114.00  44.00   59
  2  ω     -3.00  52.00   1.00   35.00    --   27.05 -53.00  17.00   55
  3  ω    -28.00  -1.00   1.00   35.00    --   27.05  97.00 -35.00   27
  4  ω    -32.00  22.00   1.00   35.00    --   27.05  39.00 -12.00   54
  5  ω     15.00  60.00   1.00   35.00    --   27.05 -77.00-150.00   45
  6  ω    -28.00  -1.00   1.00   35.00    --   27.05  97.00 143.00   27
  7  ω    -33.00  22.00   1.00   35.00    --   27.05  39.00 167.00   55
  8  ω    -22.00  32.00   1.00   35.00    --  -27.91 -39.00  12.00   54
  9  ω    -22.00  47.00   1.00   35.00    --  -27.91 -19.00-180.00   69
 10  ω    -39.00  30.00   1.00   35.00    --  -27.91  13.00  -3.00   69
 11  ω      1.00  27.00   1.00   35.00    --  -27.91 -97.00-143.00   26
 12  ω    -52.00  17.00   1.00   35.00    --  -27.91  53.00 162.00   69
 13  ω     -8.00  47.00   1.00   35.00    --   27.05 -39.00  12.00   55
 14  ω    -47.00  -8.00   1.00   35.00    --   27.05  19.00-150.00   39
 15  ω     -8.00  52.00   1.00   35.00    --   27.05 -53.00-162.00   60
 16  ω     69.00 102.00   1.00   35.00    --   27.05 178.00 -90.00   33
 17  ω   -111.00 -78.00   1.00   35.00    --  -27.91 178.00 -90.00   33
 18  ω    -35.00 -10.00   1.00   35.00    --  -27.91   0.00-180.00   25
 19  ω    -63.00   6.00   1.00   35.00    --  -27.91  81.00 -29.00   69
 20  ω     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       'ω 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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 0.88(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                192
_reflns_number_total             420
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_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_R_factor_all          0.2022
_refine_ls_R_factor_gt           0.0864
_refine_ls_restrained_S_all      1.060
_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/[σ²(Fo²)+(0.0829P)²+1.6991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.2278
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1593(13) 0.3918(19) 0.4138(11) 0.040(3) Uiso 1 1 d . . . . .
H1 H 0.217483 0.441087 0.431126 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1305(14) 0.1851(18) 0.4528(12) 0.047(3) Uiso 1 1 d . . . . .
H2 H 0.168969 0.097301 0.494769 0.056 Uiso 1 1 calc R U . . .
C3 C 0.0457(15) 0.1156(18) 0.4282(13) 0.034(3) Uiso 1 1 d . . . . .
C4 C -0.0103(14) 0.2464(19) 0.3659(12) 0.043(3) Uiso 1 1 d . . . . .
H4 H -0.068936 0.204000 0.349290 0.051 Uiso 1 1 calc R U . . .
C5 C 0.0223(14) 0.4447(18) 0.3277(12) 0.046(3) Uiso 1 1 d . . . . .
H5 H -0.014589 0.526231 0.284134 0.055 Uiso 1 1 calc R U . . .
C6 C 0.0115(12) -0.0878(16) 0.4724(10) 0.038(3) Uiso 1 1 d . . . . .
H6A H -0.039108 -0.191890 0.440165 0.046 Uiso 1 1 calc R U . . .
H6B H 0.054836 -0.235820 0.497099 0.046 Uiso 1 1 calc R U . . .
N1 N 0.1072(13) 0.5189(16) 0.3537(11) 0.040(2) Uiso 1 1 d . . . . .
C7 C 0.2431(10) 0.971(2) 0.3228(9) 0.042(3) Uiso 1 1 d D . . . .
C8 C 0.2745(15) 1.1988(19) 0.2828(11) 0.037(3) Uiso 1 1 d . . . . .
H8 H 0.330347 1.271545 0.304601 0.044 Uiso 1 1 calc R U . . .
O1 O 0.1623(9) 0.8898(12) 0.2852(7) 0.051(2) Uiso 1 1 d D . . . .
H1A H 0.146262 0.772069 0.309183 0.077 Uiso 1 1 calc R U . . .
O2 O 0.2900(10) 0.8699(14) 0.3794(9) 0.057(3) Uiso 1 1 d D . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.401(12) . ?
C1 N1 1.32(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.35(3) . ?
C3 C4 1.38(3) . ?
C3 C6 1.515(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.403(13) . ?
C5 H5 0.9300 . ?
C5 N1 1.36(3) . ?
C6 C6 1.511(19) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.503(13) . ?
C7 O1 1.328(16) . ?
C7 O2 1.195(17) . ?
C8 C8 1.34(4) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(19) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 119(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.9(11) . . ?
C2 C3 C6 120(2) . . ?
C4 C3 C6 119.9(18) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
N1 C5 C4 121(2) . . ?
N1 C5 H5 119.6 . . ?
C3 C6 H6A 109.4 . . ?
C3 C6 H6B 109.4 . . ?
C6 C6 C3 111.0(8) 5_556 . ?
C6 C6 H6A 109.4 5_556 . ?
C6 C6 H6B 109.4 5_556 . ?
H6A C6 H6B 108.0 . . ?
C1 N1 C5 118.9(11) . . ?
O1 C7 C8 111.8(15) . . ?
O2 C7 C8 121.2(15) . . ?
O2 C7 O1 126.9(11) . . ?
C7 C8 H8 118.7 . . ?
C8 C8 C7 123(2) 7_575 . ?
C8 C8 H8 118.7 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.3(16) . . . . ?
C1 C2 C3 C6 -175.1(7) . . . . ?
C2 C1 N1 C5 -0.8(16) . . . . ?
C2 C3 C4 C5 1.7(18) . . . . ?
C2 C3 C6 C6 87(2) . . . 5_556 ?
C3 C4 C5 N1 -3.4(16) . . . . ?
C4 C3 C6 C6 -89(2) . . . 5_556 ?
C4 C5 N1 C1 2.9(15) . . . . ?
C6 C3 C4 C5 177.1(8) . . . . ?
N1 C1 C2 C3 -0.8(15) . . . . ?
O1 C7 C8 C8 -0.3(15) . . . 7_575 ?
O2 C7 C8 C8 175.3(11) . . . 7_575 ?


_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_358
_database_code_depnum_ccdc_archive 'CCDC 2340679'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-18 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
# start Validation Reply Form
_vrf_ATOM007_etyfum_358          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
_vrf_PLAT029_etyfum_358          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.162 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data.
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
_vrf_PLAT088_etyfum_358          
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.03 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data.
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
_vrf_PLAT149_etyfum_358          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.40 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter.
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
_vrf_PLAT201_etyfum_358          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
_vrf_PLAT340_etyfum_358          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02875 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model. 
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
_vrf_PLAT911_etyfum_358          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        910 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data.
Quality and completness of data might also be affected by increasing strain as 
crystal approaches critical pressure of c.a. 3.8 GPa when it is destroyed.'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c12h12n2, c4h4o4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.89(5)
_cell_length_b                   3.9930(4)
_cell_length_c                   20.19(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.9(4)
_cell_angle_gamma                90
_cell_volume                     1225(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    875
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.1100
_cell_measurement_theta_min      4.0670
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.961
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 -5 -10 0.0939
15 -2 -25 0.1385
14 3 -23 0.1818
6 5 -10 0.1690
-6 5 10 0.1613
-15 2 25 0.1094
-13 -3 21 0.1266
14 0 13 0.0250
-14 0 -13 0.0250

_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
_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
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.0599 -5.2512 -9.9507 0.0750 -0.4205 -0.9042
14.9469 -2.3006 -24.8561 0.1692 -0.9226 -0.3467
14.0055 2.8834 -23.4385 0.1510 -0.8103 0.5662
5.8762 5.2575 -9.9527 0.0573 -0.2965 0.9533
-6.1888 5.2334 10.1663 -0.0764 0.4280 0.9005
-15.1191 2.1608 25.1474 -0.1709 0.9314 0.3213
-12.8150 -3.4804 21.4709 -0.1369 0.7324 -0.6670
14.0852 0.0661 13.1312 -1.0000 0.0000 0.0000
-14.0852 -0.0661 -13.1312 1.0000 0.0000 0.0000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      298.00
_diffrn_ambient_pressure         3580000
_diffrn.ambient_pressure_su      20000
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   30.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   30.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   30.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   30.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   30.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   30.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   30.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   30.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   30.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   30.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   30.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   30.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   30.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   30.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   30.00    --  -30.00 134.60 123.10   72
 16  ω    -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       'ω and φ 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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 3.58(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                98
_reflns_number_total             205
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0826
_refine_ls_restrained_S_all      1.095
_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/[σ²(Fo²)+(0.1618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2137
_refine_ls_wR_factor_ref         0.2789
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1602(10) 0.3634(18) 0.4136(8) 0.069(4) Uiso 1 1 d G . . . .
H1 H 0.219935 0.406829 0.430431 0.083 Uiso 1 1 calc R U . . .
N1 N 0.0998(11) 0.5050(12) 0.3481(8) 0.059(3) Uiso 1 1 d G . . . .
C5 C 0.0105(10) 0.4401(16) 0.3229(8) 0.055(3) Uiso 1 1 d G . . . .
H5 H -0.029926 0.534869 0.279064 0.066 Uiso 1 1 calc R U . . .
C4 C -0.0185(10) 0.2335(19) 0.3633(9) 0.060(3) Uiso 1 1 d G . . . .
H4 H -0.078236 0.190047 0.346431 0.072 Uiso 1 1 calc R U . . .
C3 C 0.0419(11) 0.0918(15) 0.4288(8) 0.069(5) Uiso 1 1 d G . . . .
C2 C 0.1312(11) 0.1568(18) 0.4540(8) 0.062(4) Uiso 1 1 d G . . . .
H2 H 0.171624 0.062001 0.497799 0.075 Uiso 1 1 calc R U . . .
C6 C 0.0035(19) -0.116(2) 0.4695(14) 0.043(3) Uiso 1 1 d . . . . .
H6A H 0.040971 -0.307446 0.492308 0.051 Uiso 1 1 calc R U . . .
H6B H -0.054353 -0.197757 0.435894 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2477(16) 0.946(3) 0.3258(13) 0.103(8) Uiso 1 1 d D . . . .
C8 C 0.276(3) 1.199(2) 0.2827(17) 0.064(4) Uiso 1 1 d D . . . .
H8 H 0.332823 1.282221 0.304955 0.076 Uiso 1 1 calc R U . . .
O1 O 0.1639(16) 0.8949(16) 0.2880(11) 0.057(3) Uiso 1 1 d D . . . .
H1A H 0.146966 0.761231 0.309931 0.086 Uiso 1 1 calc R U . . .
O2 O 0.3012(18) 0.849(2) 0.3848(13) 0.074(3) Uiso 1 1 d D . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 N1 1.3900 . ?
C1 C2 1.3900 . ?
N1 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C3 C2 1.3900 . ?
C3 C6 1.502(9) . ?
C2 H2 0.9300 . ?
C6 C6 1.59(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.535(15) . ?
C7 O1 1.30(2) . ?
C7 O2 1.20(2) . ?
C8 C8 1.29(7) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1 120.0 . . ?
N1 C1 C2 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 N1 C5 120.0 . . ?
N1 C5 H5 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C6 115.7(14) . . ?
C2 C3 C6 124.3(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C6 C6 107.3(9) . 5_556 ?
C3 C6 H6A 110.3 . . ?
C3 C6 H6B 110.3 . . ?
C6 C6 H6A 110.3 5_556 . ?
C6 C6 H6B 110.3 5_556 . ?
H6A C6 H6B 108.5 . . ?
O1 C7 C8 107(2) . . ?
O2 C7 C8 119(2) . . ?
O2 C7 O1 133.3(17) . . ?
C7 C8 H8 118.2 . . ?
C8 C8 C7 124(4) 7_575 . ?
C8 C8 H8 118.2 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 0.0 . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
N1 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C4 C3 C6 177.7(5) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C4 C3 C6 C6 -97(3) . . . 5_556 ?
C2 C1 N1 C5 0.0 . . . . ?
C2 C3 C6 C6 81(3) . . . 5_556 ?
C6 C3 C2 C1 -177.5(5) . . . . ?
O1 C7 C8 C8 -7(2) . . . 7_575 ?
O2 C7 C8 C8 175.6(13) . . . 7_575 ?


_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_300
_database_code_depnum_ccdc_archive 'CCDC 2340680'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_300          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_300          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.239 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT088_etyfum_300          
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.85 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT149_etyfum_300          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.13 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter'
;
_vrf_PLAT201_etyfum_300          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_300          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.017 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_300          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        714 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12N2H10, C4O4H4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.874(16)
_cell_length_b                   4.0560(16)
_cell_length_c                   20.17(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.14(13)
_cell_angle_gamma                90
_cell_volume                     1239(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    397
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.0470
_cell_measurement_theta_min      4.0820
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.117
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-20 -3 5 0.0328
-23 0 19 0.0531
-7 4 19 0.0560
17 4 -1 0.1520
22 -1 -20 0.1471
11 -4 -20 0.1338
4 -3 15 0.0260
-4 3 -14 0.0090

_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.037
_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)
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-19.5819 -3.0445 5.2871 0.2260 -0.7728 0.5930
-22.9005 0.4725 18.6210 0.2799 -0.9461 -0.1630
-6.8751 4.3346 18.5210 0.1003 -0.3280 -0.9393
16.7075 3.6901 -1.1417 -0.1886 0.6479 -0.7380
22.3368 -0.9064 -19.5368 -0.2748 0.9275 0.2536
10.8114 -3.9194 -20.1907 -0.1465 0.4854 0.8619
3.6045 -3.0074 14.9876 -0.8232 -0.2356 0.0537
-3.6198 2.8180 -14.0276 0.7790 0.2134 -0.0473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.1138
_diffrn_reflns_Laue_measured_fraction_full 0.239
_diffrn_reflns_Laue_measured_fraction_max 0.237
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            688
_diffrn_reflns_point_group_measured_fraction_full 0.239
_diffrn_reflns_point_group_measured_fraction_max 0.237
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.403
_diffrn_reflns_theta_min         4.102
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         3000000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.239
_diffrn_measured_fraction_theta_max 0.237
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   30.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   30.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   30.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   30.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   30.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   30.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   30.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   30.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   30.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   30.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   30.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   30.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   30.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   30.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   30.00    --  -30.00 134.60 123.10   72
 16  ω    -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       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0334834039
_diffrn_orient_matrix_UB_12      0.0916946630
_diffrn_orient_matrix_UB_13      -0.0284717170
_diffrn_orient_matrix_UB_21      0.0295535126
_diffrn_orient_matrix_UB_22      0.0370128188
_diffrn_orient_matrix_UB_23      -0.0154010874
_diffrn_orient_matrix_UB_31      -0.0138011651
_diffrn_orient_matrix_UB_32      -0.1443309836
_diffrn_orient_matrix_UB_33      -0.0220617672
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 3.00(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                158
_reflns_number_total             269
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.077
_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/[σ²(Fo²)+(0.0548P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1568
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1626(9) 0.354(3) 0.4154(7) 0.037(3) Uiso 1 1 d . . . . .
H1 H 0.2230 0.3882 0.4324 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1325(7) 0.154(2) 0.4551(6) 0.033(3) Uiso 1 1 d . . . . .
H2 H 0.1724 0.0591 0.4991 0.040 Uiso 1 1 calc R U . . .
C3 C 0.0440(8) 0.097(2) 0.4295(7) 0.031(3) Uiso 1 1 d . . . . .
C4 C -0.0144(9) 0.247(2) 0.3644(7) 0.032(3) Uiso 1 1 d . . . . .
H4 H -0.0750 0.2150 0.3463 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0190(8) 0.445(2) 0.3268(6) 0.035(3) Uiso 1 1 d . . . . .
H5 H -0.0194 0.5434 0.2826 0.042 Uiso 1 1 calc R U . . .
C6 C 0.0091(7) -0.106(2) 0.4738(5) 0.034(3) Uiso 1 1 d . . . . .
H6A H -0.0448 -0.2164 0.4405 0.041 Uiso 1 1 calc R U . . .
H6B H 0.0521 -0.2735 0.5014 0.041 Uiso 1 1 calc R U . . .
N1 N 0.1061(7) 0.498(2) 0.3534(6) 0.038(3) Uiso 1 1 d . . . . .
C7 C 0.2454(10) 0.953(3) 0.3242(8) 0.033(3) Uiso 1 1 d . . . . .
C8 C 0.2750(9) 1.193(2) 0.2821(6) 0.032(3) Uiso 1 1 d . . . . .
H8 H 0.3335 1.2617 0.3045 0.039 Uiso 1 1 calc R U . . .
O1 O 0.1622(6) 0.8900(16) 0.2875(4) 0.044(2) Uiso 1 1 d . . . . .
H1A H 0.1459 0.7761 0.3128 0.066 Uiso 1 1 calc R U . . .
O2 O 0.2958(6) 0.8408(17) 0.3828(5) 0.043(2) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.383(11) . ?
C1 N1 1.328(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(15) . ?
C3 C4 1.389(16) . ?
C3 C6 1.512(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(11) . ?
C5 H5 0.9300 . ?
C5 N1 1.341(13) . ?
C6 C6 1.495(14) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.512(12) . ?
C7 O1 1.291(16) . ?
C7 O2 1.201(15) . ?
C8 C8 1.28(2) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.5(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(12) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 118.9(10) . . ?
C2 C3 C6 121.0(10) . . ?
C4 C3 C6 119.9(11) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(13) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.6 . . ?
N1 C5 C4 120.9(12) . . ?
N1 C5 H5 119.6 . . ?
C3 C6 H6A 109.4 . . ?
C3 C6 H6B 109.4 . . ?
C6 C6 C3 111.1(9) 5_556 . ?
C6 C6 H6A 109.4 5_556 . ?
C6 C6 H6B 109.4 5_556 . ?
H6A C6 H6B 108.0 . . ?
C1 N1 C5 120.8(10) . . ?
O1 C7 C8 110.5(12) . . ?
O2 C7 C8 122.0(13) . . ?
O2 C7 O1 127.5(10) . . ?
C7 C8 H8 117.7 . . ?
C8 C8 C7 124.6(16) 7_575 . ?
C8 C8 H8 117.7 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -1.3(15) . . . . ?
C1 C2 C3 C6 -176.7(8) . . . . ?
C2 C1 N1 C5 -1.8(17) . . . . ?
C2 C3 C4 C5 1.2(17) . . . . ?
C2 C3 C6 C6 88.6(13) . . . 5_556 ?
C3 C4 C5 N1 -1.3(15) . . . . ?
C4 C3 C6 C6 -86.8(15) . . . 5_556 ?
C4 C5 N1 C1 1.6(15) . . . . ?
C6 C3 C4 C5 176.6(7) . . . . ?
N1 C1 C2 C3 1.6(15) . . . . ?
O1 C7 C8 C8 -2.4(16) . . . 7_575 ?
O2 C7 C8 C8 176.4(12) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_300 in I2/a 
REM I2/a (#15 with fixed user cell (not necessary: std = user cell)!)
CELL 0.71073  16.873742   4.056037  20.171633  90.0000 116.1449  90.0000
ZERR    3.00   0.016517   0.001639   0.020703   0.0000   0.1335   0.0000
LATT  2
SYMM -x+1/2, y,-z 
SFAC C H N O
UNIT 48.00 42.00 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 3.00(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 2.152
_oxdiff_exptl_absorpt_empirical_full_min 0.469
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_244
_database_code_depnum_ccdc_archive 'CCDC 2340684'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_244          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_244          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.284 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT088_etyfum_244          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.11 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT149_etyfum_244          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.08 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter'
;
_vrf_PLAT201_etyfum_244          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_244          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01862 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_244          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        785 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N2, C4 H4 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.836(10)
_cell_length_b                   4.1496(11)
_cell_length_c                   20.120(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.18(8)
_cell_angle_gamma                90
_cell_volume                     1272.0(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    534
_cell_measurement_temperature    298
_cell_measurement_theta_max      19.5490
_cell_measurement_theta_min      4.1210
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.995
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-20 -3 5 0.0328
-23 1 18 0.0531
-7 4 18 0.0560
17 4 -1 0.1520
22 -1 -19 0.1471
11 -4 -20 0.1338
3 -3 16 0.0260
-3 3 -15 0.0090

_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-19.7578 -2.9964 4.6904 0.2260 -0.7728 0.5930
-22.9043 0.6256 17.8559 0.2799 -0.9461 -0.1630
-6.6662 4.4813 18.2213 0.1003 -0.3280 -0.9393
16.9123 3.6754 -0.6508 -0.1886 0.6479 -0.7380
22.3182 -1.0665 -18.7830 -0.2748 0.9275 0.2536
10.6280 -4.0805 -19.7678 -0.1465 0.4854 0.8619
3.0069 -3.0948 15.5145 -0.8232 -0.2356 0.0537
-3.0574 2.9014 -14.5316 0.7790 0.2134 -0.0473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_Laue_measured_fraction_full 0.284
_diffrn_reflns_Laue_measured_fraction_max 0.268
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1394
_diffrn_reflns_point_group_measured_fraction_full 0.284
_diffrn_reflns_point_group_measured_fraction_max 0.268
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.781
_diffrn_reflns_theta_min         2.658
_diffrn_ambient_temperature      298.00
_diffrn_ambient_pressure         2440000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.284
_diffrn_measured_fraction_theta_max 0.268
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -15.00   1.00   15.00    --   -0.27  37.00-150.00   47
  2  ω    -49.00  11.00   1.00   15.00    --   -0.27  81.00 -29.00   60
  3  ω     -1.00  68.00   1.00   22.50    --   26.72 -81.00-151.00   69
  4  ω     70.00 111.00   1.00   22.50    --   26.72 178.00  90.00   41
  5  ω    -27.00  22.00   1.00   22.50    --   26.72 -19.00-150.00   49
  6  ω    -19.00  22.00   1.00   22.50    --   26.72  53.00 -17.00   41
  7  ω    -38.00  27.00   1.00   22.50    --   26.72  39.00 167.00   65
  8  ω    -30.00   4.00   1.00   22.50    --   26.72  97.00 -35.00   34
  9  ω    -35.00 -15.00   1.00   22.50    --   26.72  37.00   0.00   20
 10  ω    -48.00  16.00   1.00   22.50    --   26.72  37.00-180.00   64
 11  ω    -51.00 -17.00   1.00   22.50    --   26.72 134.00 123.00   34
 12  ω    -10.00  62.00   1.00   22.50    --   26.72 -67.00  23.00   72
 13  ω    -22.00  11.00   1.00   22.50    --   26.72  81.00 151.00   33
 14  ω     -4.00  16.00   1.00   22.50    --  -27.26 -57.00  30.00   20
 15  ω    -52.00  27.00   1.00   22.50    --  -27.26  39.00 -12.00   79
 16  ω    -57.00  22.00   1.00   22.50    --  -27.26  53.00 -17.00   79
 17  ω    -27.00  38.00   1.00   22.50    --  -27.26 -39.00-167.00   65
 18  ω    -16.00  49.00   1.00   22.50    --  -27.26 -37.00-180.00   65
 19  ω    -22.00  18.00   1.00   22.50    --  -27.26 -53.00  17.00   40
 20  ω   -121.00 -69.00   1.00   22.50    --  -27.26 178.00 -90.00   52
 21  ω      5.00  37.00   1.00   22.50    --  -27.26-114.00-136.00   32
 22  ω    -75.00   4.00   1.00   22.50    --  -27.26  97.00 143.00   79
 23  ω      5.00  37.00   1.00   22.50    --  -27.26-114.00  44.00   32
 24  ω    -17.00  16.00   1.00   22.50    --  -27.26 -67.00-157.00   33
 25  ω    -16.00  35.00   1.00   15.00    --   -0.27 -37.00-150.00   51
 26  ω     -4.00  18.00   1.00   22.50    --   26.72 -57.00  60.00   22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0320686000
_diffrn_orient_matrix_UB_12      0.0911897000
_diffrn_orient_matrix_UB_13      -0.0286527000
_diffrn_orient_matrix_UB_21      0.0307279000
_diffrn_orient_matrix_UB_22      0.0322919000
_diffrn_orient_matrix_UB_23      -0.0147004000
_diffrn_orient_matrix_UB_31      -0.0138580000
_diffrn_orient_matrix_UB_32      -0.1409157000
_diffrn_orient_matrix_UB_33      -0.0219649000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 2.44(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                173
_reflns_number_total             327
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      1.070
_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/[σ²(Fo²)+(0.1175P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.2360
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1618(9) 0.364(2) 0.4146(8) 0.037(3) Uiso 1 1 d . . . . .
H1 H 0.2216 0.4035 0.4317 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1324(8) 0.161(2) 0.4543(7) 0.046(3) Uiso 1 1 d . . . . .
H2 H 0.1721 0.0666 0.4977 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0438(9) 0.100(2) 0.4288(7) 0.033(3) Uiso 1 1 d . . . . .
C4 C -0.0142(9) 0.248(3) 0.3646(7) 0.040(3) Uiso 1 1 d . . . . .
H4 H -0.0745 0.2179 0.3467 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0214(9) 0.441(2) 0.3286(8) 0.041(3) Uiso 1 1 d . . . . .
H5 H -0.0167 0.5340 0.2844 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0102(7) -0.103(2) 0.4733(7) 0.035(3) Uiso 1 1 d . . . . .
H6A H 0.0539 -0.2637 0.5004 0.042 Uiso 1 1 calc R U . . .
H6B H -0.0426 -0.2152 0.4405 0.042 Uiso 1 1 calc R U . . .
N1 N 0.1061(8) 0.5028(19) 0.3528(7) 0.042(3) Uiso 1 1 d . . . . .
C7 C 0.2428(11) 0.957(2) 0.3231(9) 0.039(4) Uiso 1 1 d . . . . .
C8 C 0.2740(9) 1.194(3) 0.2818(7) 0.039(3) Uiso 1 1 d . . . . .
H8 H 0.3321 1.2623 0.3045 0.047 Uiso 1 1 calc R U . . .
O1 O 0.1618(6) 0.8849(16) 0.2865(5) 0.047(2) Uiso 1 1 d . . . . .
H1A H 0.1448 0.7797 0.3124 0.071 Uiso 1 1 calc R U . . .
O2 O 0.2950(6) 0.8464(17) 0.3818(5) 0.046(3) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.389(12) . ?
C1 N1 1.329(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(16) . ?
C3 C4 1.388(18) . ?
C3 C6 1.505(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(13) . ?
C5 H5 0.9300 . ?
C5 N1 1.321(13) . ?
C6 C6 1.524(17) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.517(14) . ?
C7 O1 1.280(17) . ?
C7 O2 1.223(17) . ?
C8 C8 1.28(2) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.4 . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.2(14) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(13) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 119.2(11) . . ?
C2 C3 C6 120.2(12) . . ?
C4 C3 C6 120.5(13) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.1(14) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 117.9 . . ?
N1 C5 C4 124.2(13) . . ?
N1 C5 H5 117.9 . . ?
C3 C6 C6 111.1(9) . 5_556 ?
C3 C6 H6A 109.4 . . ?
C3 C6 H6B 109.4 . . ?
C6 C6 H6A 109.4 5_556 . ?
C6 C6 H6B 109.4 5_556 . ?
H6A C6 H6B 108.0 . . ?
C5 N1 C1 118.9(11) . . ?
O1 C7 C8 111.6(13) . . ?
O2 C7 C8 119.9(14) . . ?
O2 C7 O1 128.3(12) . . ?
C7 C8 H8 117.7 . . ?
C8 C8 C7 124.5(18) 7_575 . ?
C8 C8 H8 117.7 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -1.1(16) . . . . ?
C1 C2 C3 C6 -176.3(9) . . . . ?
C2 C1 N1 C5 -1.0(18) . . . . ?
C2 C3 C4 C5 2.1(18) . . . . ?
C2 C3 C6 C6 89.0(13) . . . 5_556 ?
C3 C4 C5 N1 -2.7(16) . . . . ?
C4 C3 C6 C6 -86.1(17) . . . 5_556 ?
C4 C5 N1 C1 2.2(16) . . . . ?
C6 C3 C4 C5 177.3(8) . . . . ?
N1 C1 C2 C3 0.5(16) . . . . ?
O1 C7 C8 C8 -0.7(18) . . . 7_575 ?
O2 C7 C8 C8 175.2(12) . . . 7_575 ?

_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 decompressed to 2.44(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 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_133
_database_code_depnum_ccdc_archive 'CCDC 2340681'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-02-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_133          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_133          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.279 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT088_etyfum_133          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.91 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT149_etyfum_133          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.60 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter'
;
_vrf_PLAT201_etyfum_133          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_133          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0325 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_133          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        824 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4O4H4, N2C12H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.79(9)
_cell_length_b                   4.3174(13)
_cell_length_c                   19.94(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.2(6)
_cell_angle_gamma                90
_cell_volume                     1329(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    420
_cell_measurement_temperature    298
_cell_measurement_theta_max      14.7520
_cell_measurement_theta_min      4.1380
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.403
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 4 -18 0.1090
-15 4 14 0.1042
-14 -4 19 0.1410
10 -5 -8 0.0709
-14 -2 -16 0.0100
15 3 18 0.0100

_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
_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)      0.404     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
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.0846 4.3866 -17.8725 -0.0273 -0.9790 0.2019
-15.0223 4.4287 13.9240 -0.0038 -0.2745 -0.9616
-13.5435 -3.9772 19.2421 0.0270 0.9555 -0.2938
10.4192 -5.4355 -7.6736 0.0117 0.5472 0.8369
-14.4947 -1.7443 -15.6116 -1.0933 0.1432 0.0126
14.8923 2.6253 18.2055 1.2136 -0.2308 -0.1155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1422
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 0.279
_diffrn_reflns_Laue_measured_fraction_max 0.250
_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       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2369
_diffrn_reflns_point_group_measured_fraction_full 0.279
_diffrn_reflns_point_group_measured_fraction_max 0.250
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.752
_diffrn_reflns_theta_min         2.698
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         1330000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.279
_diffrn_measured_fraction_theta_max 0.250
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  43.00   1.00   35.00    --   27.06 -26.00   7.00   58
  2  ω     17.00  60.00   1.00   35.00    --   27.06 -77.00-150.00   43
  3  ω    -29.00  -1.00   1.00   35.00    --   27.06  97.00 -35.00   28
  4  ω    -21.00   6.00   1.00   35.00    --   27.06  81.00 151.00   27
  5  ω    -33.00  26.00   1.00   35.00    --   27.06  26.00 172.00   59
  6  ω    -36.00  22.00   1.00   35.00    --   27.06  39.00 -12.00   58
  7  ω     11.00  36.00   1.00   35.00    --  -27.92-114.00  44.00   25
  8  ω    -21.00  37.00   1.00   35.00    --  -27.92 -39.00  12.00   58
  9  ω    -21.00  37.00   1.00   35.00    --  -27.92 -39.00-167.00   58
 10  ω    -43.00  26.00   1.00   35.00    --  -27.92  26.00  -7.00   69
 11  ω     23.00  50.00   1.00   35.00    --  -27.92-134.00-123.00   27
 12  ω    -46.00  22.00   1.00   35.00    --  -27.92  39.00 167.00   68
 13  ω    -90.00 -22.00   1.00   35.00    --  -27.92 134.00 -56.00   68
 14  ω      9.00  66.00   1.00   35.00    --   27.06 -57.00-180.00   57
 15  ω     32.00  91.00   1.00   35.00    --   27.06-134.00-123.00   59
 16  ω     71.00 102.00   1.00   35.00    --   27.06 178.00 -90.00   31
 17  ω    -20.00  17.00   1.00   35.00    --   27.06 -19.00-150.00   37
 18  ω    -15.00  12.00   1.00   35.00    --   27.06  67.00 157.00   27
 19  ω    -51.00 -22.00   1.00   35.00    --   27.06 134.00 123.00   29
 20  ω   -110.00 -78.00   1.00   35.00    --  -27.92 178.00 -90.00   32
 21  ω    -10.00  48.00   1.00   35.00    --  -27.92 -37.00-180.00   58
 22  ω      5.00  30.00   1.00   35.00    --  -27.92 -99.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374466000
_diffrn_orient_matrix_UB_12      0.0235624000
_diffrn_orient_matrix_UB_13      0.0326318000
_diffrn_orient_matrix_UB_21      -0.0089966000
_diffrn_orient_matrix_UB_22      -0.1386251000
_diffrn_orient_matrix_UB_23      0.0146712000
_diffrn_orient_matrix_UB_31      0.0253250000
_diffrn_orient_matrix_UB_32      -0.0844101000
_diffrn_orient_matrix_UB_33      -0.0148892000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 1.33(2) GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                158
_reflns_number_total             356
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         356
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      0.998
_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/[σ²(Fo²)+(0.0654P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1830
_refine_special_details          ?
_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-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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1613(16) 0.377(2) 0.4151(12) 0.041(3) Uiso 1 1 d . . . . .
H1 H 0.2201 0.4229 0.4322 0.050 Uiso 1 1 calc R U . . .
C2 C 0.1329(16) 0.1674(19) 0.4544(14) 0.049(3) Uiso 1 1 d . . . . .
H2 H 0.1718 0.0731 0.4965 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0448(16) 0.1049(19) 0.4285(13) 0.028(3) Uiso 1 1 d . . . . .
C4 C -0.0092(16) 0.246(2) 0.3669(14) 0.036(3) Uiso 1 1 d . . . . .
H4 H -0.0684 0.2078 0.3507 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0198(16) 0.4453(19) 0.3266(13) 0.044(3) Uiso 1 1 d . . . . .
H5 H -0.0182 0.5305 0.2828 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0092(14) -0.0976(16) 0.4720(12) 0.038(3) Uiso 1 1 d . . . . .
H6A H 0.0509 -0.2582 0.4967 0.046 Uiso 1 1 calc R U . . .
H6B H -0.0437 -0.1969 0.4394 0.046 Uiso 1 1 calc R U . . .
N1 N 0.1074(15) 0.5117(17) 0.3544(12) 0.042(3) Uiso 1 1 d . . . . .
C7 C 0.2450(14) 0.962(2) 0.3246(12) 0.048(4) Uiso 1 1 d D . . . .
C8 C 0.2759(19) 1.196(2) 0.2832(14) 0.042(3) Uiso 1 1 d . . . . .
H8 H 0.3327 1.2674 0.3044 0.050 Uiso 1 1 calc R U . . .
O1 O 0.1631(11) 0.8894(13) 0.2867(9) 0.050(2) Uiso 1 1 d D . . . .
H1A H 0.1465 0.7708 0.3107 0.075 Uiso 1 1 calc R U . . .
O2 O 0.2946(14) 0.8581(16) 0.3818(12) 0.061(3) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.397(12) . ?
C1 N1 1.33(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.39(4) . ?
C3 C4 1.35(4) . ?
C3 C6 1.510(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(14) . ?
C5 H5 0.9300 . ?
C5 N1 1.38(3) . ?
C6 C6 1.53(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.518(14) . ?
C7 O1 1.32(2) . ?
C7 O2 1.20(3) . ?
C8 C8 1.35(6) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 118(2) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C6 120(2) . . ?
C4 C3 C2 119.0(13) . . ?
C4 C3 C6 121(2) . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 123(2) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 H5 121.4 . . ?
N1 C5 C4 117(2) . . ?
N1 C5 H5 121.4 . . ?
C3 C6 C6 109.9(8) . 5_556 ?
C3 C6 H6A 109.7 . . ?
C3 C6 H6B 109.7 . . ?
C6 C6 H6A 109.7 5_556 . ?
C6 C6 H6B 109.7 5_556 . ?
H6A C6 H6B 108.2 . . ?
C1 N1 C5 120.6(13) . . ?
O1 C7 C8 110.5(19) . . ?
O2 C7 C8 120(2) . . ?
O2 C7 O1 128.9(14) . . ?
C7 C8 H8 118.8 . . ?
C8 C8 C7 122(3) 7_575 . ?
C8 C8 H8 118.8 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.4(15) . . . . ?
C1 C2 C3 C6 -174.8(8) . . . . ?
C2 C1 N1 C5 -1.1(17) . . . . ?
C2 C3 C4 C5 2.0(19) . . . . ?
C2 C3 C6 C6 86(2) . . . 5_556 ?
C3 C4 C5 N1 -3.8(17) . . . . ?
C4 C3 C6 C6 -89(3) . . . 5_556 ?
C4 C5 N1 C1 3.3(14) . . . . ?
C6 C3 C4 C5 177.1(8) . . . . ?
N1 C1 C2 C3 -0.8(15) . . . . ?
O1 C7 C8 C8 -0.5(16) . . . 7_575 ?
O2 C7 C8 C8 175.7(13) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_130_final in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.791134   4.317396  19.943976  90.0000 113.2363  90.0000
ZERR    3.00   0.086675   0.001266   0.094213   0.0000   0.6371   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 0.03 0.20 0.31
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 1.33(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 2.737
_oxdiff_exptl_absorpt_empirical_full_min 0.558
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_015
_database_code_depnum_ccdc_archive 'CCDC 2340683'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_015          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT029_etyfum_015          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.221 Why?  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT026_etyfum_015          
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        39% Check 
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT088_etyfum_015          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.00 Note  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT149_etyfum_015          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.20 Degree
RESPONSE: "Quality of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT201_etyfum_015          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT340_etyfum_015          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.035 Ang.  
RESPONSE: "Quality of structural model affected by poor quality and low number 
of experimental data"
;
_vrf_PLAT911_etyfum_015          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1003 Report
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4H4O4, N2C12H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.72(3)
_cell_length_b                   4.7728(7)
_cell_length_c                   19.70(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.1(2)
_cell_angle_gamma                90
_cell_volume                     1476(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    471
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.2210
_cell_measurement_theta_min      2.7630
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.453
_exptl_absorpt_correction_T_min  0.403
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-17 -5 12 0.1090
13 -5 -15 0.1042
18 5 -13 0.1410
-7 6 11 0.0709
-17 2 -14 0.0100
20 -3 15 0.0100

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_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)      0.404     0.454
         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 = 150.0 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

    Non-absorbing pressure medium
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-16.6588 -4.9560 11.5714 -0.0273 -0.9790 0.2019
13.3486 -4.7465 -15.2939 -0.0038 -0.2745 -0.9616
17.9705 4.5179 -13.0548 0.0270 0.9555 -0.2938
-7.4978 5.9013 10.8252 0.0117 0.5472 0.8369
-17.1136 1.9186 -14.4237 -1.0933 0.1432 0.0126
19.8592 -2.8788 14.7613 1.2136 -0.2308 -0.1155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.1619
_diffrn_reflns_Laue_measured_fraction_full 0.221
_diffrn_reflns_Laue_measured_fraction_max 0.162
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1360
_diffrn_reflns_point_group_measured_fraction_full 0.221
_diffrn_reflns_point_group_measured_fraction_max 0.162
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.828
_diffrn_reflns_theta_min         2.767
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         150000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.221
_diffrn_measured_fraction_theta_max 0.162
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  43.00   1.00   35.00    --   -0.90 -26.00   7.00   69
  2  ω    -12.00  42.00   1.00   35.00    --   -0.90 -67.00-157.00   54
  3  ω    -42.00  12.00   1.00   35.00    --    0.90  67.00 -23.00   54
  4  ω    -48.00   6.00   1.00   35.00    --    0.90  81.00 151.00   54
  5  ω    -43.00   1.00   1.00   35.00    --  -48.59  26.00 172.00   44
  6  ω    -61.00 -18.00   1.00   35.00    --  -48.59  45.00-180.00   43
  7  ω    -70.00 -24.00   1.00   35.00    --  -48.59  97.00 143.00   46
  8  ω    -79.00 -34.00   1.00   35.00    --  -48.59 114.00 -44.00   45
  9  ω    -35.00  10.00   1.00   35.00    --  -48.59   0.00-180.00   45
 10  ω    -47.00  -6.00   1.00   35.00    --  -48.59  39.00 -12.00   41
 11  ω    -31.00   6.00   1.00   35.00    --  -48.59 -45.00-150.00   37
 12  ω    -31.00   1.00   1.00   35.00    --  -48.59 -45.00  30.00   32
 13  ω    -35.00  10.00   1.00   35.00    --  -48.59   0.00   0.00   45
 14  ω    -17.00  22.00   1.00   35.00    --   48.59  39.00 -12.00   39
 15  ω    -17.00  22.00   1.00   35.00    --   48.59  39.00 167.00   39
 16  ω     21.00  63.00   1.00   35.00    --   48.59 -81.00-151.00   42
 17  ω   -100.00 -78.00   1.00   35.00    --   -0.90 178.00 -90.00   22
 18  ω     -5.00  48.00   1.00   35.00    --   -0.90 -81.00  29.00   53
 19  ω     69.00 100.00   1.00   35.00    --    0.90 178.00 -90.00   31
 20  ω    -98.00 -76.00   1.00   35.00    --    0.90-178.00 -90.00   22
 21  ω     -5.00  36.00   1.00   35.00    --   48.59 -45.00-150.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0321382000
_diffrn_orient_matrix_UB_12      -0.0211282000
_diffrn_orient_matrix_UB_13      0.0348572000
_diffrn_orient_matrix_UB_21      0.0140381000
_diffrn_orient_matrix_UB_22      0.1280687000
_diffrn_orient_matrix_UB_23      -0.0095460000
_diffrn_orient_matrix_UB_31      -0.0152027000
_diffrn_orient_matrix_UB_32      0.0731670000
_diffrn_orient_matrix_UB_33      0.0268969000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 0.15(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                123
_reflns_number_total             315
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         315
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2189
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.021
_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/[σ²(Fo²)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_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-C8
 1.5 with sigma of 0.005
 N1-C1
 1.32 with sigma of 0.02
 N1-C5
 1.32 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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1589(10) 0.415(2) 0.4147(10) 0.043(4) Uiso 1 1 d D . . . .
H1 H 0.2154 0.4729 0.4326 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1302(16) 0.208(2) 0.4528(14) 0.048(4) Uiso 1 1 d . . . . .
H2 H 0.1683 0.1217 0.4934 0.058 Uiso 1 1 calc R U . . .
C3 C 0.0474(17) 0.137(2) 0.4293(15) 0.025(4) Uiso 1 1 d . . . . .
C4 C -0.0102(17) 0.252(3) 0.3645(16) 0.049(5) Uiso 1 1 d . . . . .
H4 H -0.0672 0.1991 0.3460 0.058 Uiso 1 1 calc R U . . .
C5 C 0.0249(12) 0.451(2) 0.3302(11) 0.053(4) Uiso 1 1 d D . . . .
H5 H -0.0110 0.5333 0.2880 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0130(12) -0.0748(16) 0.4716(12) 0.040(3) Uiso 1 1 d . . . . .
H6A H -0.0358 -0.1726 0.4386 0.048 Uiso 1 1 calc R U . . .
H6B H 0.0566 -0.2123 0.4946 0.048 Uiso 1 1 calc R U . . .
N1 N 0.1072(10) 0.5283(19) 0.3547(9) 0.041(4) Uiso 1 1 d D . . . .
C7 C 0.241(2) 0.976(3) 0.320(2) 0.059(6) Uiso 1 1 d D . . . .
C8 C 0.2731(19) 1.202(2) 0.2826(15) 0.038(3) Uiso 1 1 d D . . . .
H8 H 0.3270 1.2774 0.3059 0.046 Uiso 1 1 calc R U . . .
O1 O 0.1623(13) 0.9005(14) 0.2840(12) 0.057(3) Uiso 1 1 d . . . . .
H1A H 0.1468 0.7851 0.3077 0.085 Uiso 1 1 calc R U . . .
O2 O 0.2863(17) 0.8876(17) 0.3777(13) 0.054(4) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.423(13) . ?
C1 N1 1.316(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.34(3) . ?
C3 C4 1.42(4) . ?
C3 C6 1.542(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(14) . ?
C5 H5 0.9300 . ?
C5 N1 1.344(17) . ?
C6 C6 1.51(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.506(5) . ?
C7 O1 1.31(5) . ?
C7 O2 1.21(5) . ?
C8 C8 1.33(6) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.2 . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.5(17) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.9(14) . . ?
C2 C3 C6 121(2) . . ?
C4 C3 C6 118(2) . . ?
C3 C4 H4 122.3 . . ?
C5 C4 C3 115(2) . . ?
C5 C4 H4 122.3 . . ?
C4 C5 H5 118.0 . . ?
N1 C5 C4 123.9(19) . . ?
N1 C5 H5 118.0 . . ?
C3 C6 H6A 109.6 . . ?
C3 C6 H6B 109.6 . . ?
C6 C6 C3 110.3(9) 5_556 . ?
C6 C6 H6A 109.6 5_556 . ?
C6 C6 H6B 109.6 5_556 . ?
H6A C6 H6B 108.1 . . ?
C1 N1 C5 119.0(12) . . ?
O1 C7 C8 113(3) . . ?
O2 C7 C8 119(3) . . ?
O2 C7 O1 127.1(14) . . ?
C7 C8 H8 119.1 . . ?
C8 C8 C7 122(3) 7_575 . ?
C8 C8 H8 119.1 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 4.5(18) . . . . ?
C1 C2 C3 C6 -176.4(9) . . . . ?
C2 C1 N1 C5 1.9(16) . . . . ?
C2 C3 C4 C5 -3(2) . . . . ?
C2 C3 C6 C6 88(2) . . . 5_556 ?
C3 C4 C5 N1 1.1(18) . . . . ?
C4 C3 C6 C6 -93(3) . . . 5_556 ?
C4 C5 N1 C1 -0.6(15) . . . . ?
C6 C3 C4 C5 177.8(7) . . . . ?
N1 C1 C2 C3 -3.9(16) . . . . ?
O1 C7 C8 C8 -4.4(19) . . . 7_575 ?
O2 C7 C8 C8 177.0(15) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_018_final in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  19.704989   4.772762  16.715111  90.0000 110.0803  90.0000
ZERR    4.00   0.036505   0.000658   0.025755   0.0000   0.2127   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 0.22 0.33
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 0.15(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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.686
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_029
_database_code_depnum_ccdc_archive 'CCDC 2340685'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_029          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT029_etyfum_029          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.265 Why?  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT149_etyfum_029          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.30 Degree
RESPONSE: "Quality of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT201_etyfum_029          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT340_etyfum_029          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03375 Ang.  
RESPONSE: Quality of structural model affected by poor quality and low number 
of experimental data"
;
_vrf_PLAT911_etyfum_029          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        925 Report
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4O4H4, C12N2H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.70(3)
_cell_length_b                   4.7020(6)
_cell_length_c                   19.65(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.1(3)
_cell_angle_gamma                90
_cell_volume                     1449(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    828
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.7700
_cell_measurement_theta_min      2.7550
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.406
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       s
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 5 -16 0.1090
-15 5 14 0.1042
-13 -4 18 0.1410
11 -6 -8 0.0709
-15 -2 -17 0.0100
15 3 20 0.0100

_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
_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)      0.407     0.454
         range of gasket transmission (min-max)           0.997     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 = 150.0 microns, radius = 212.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
11.6767 4.9256 -16.4303 -0.0273 -0.9790 0.2019
-15.0186 4.6982 13.9303 -0.0038 -0.2745 -0.9616
-13.1342 -4.4920 17.7967 0.0270 0.9555 -0.2938
10.5371 -5.8472 -8.1084 0.0117 0.5472 0.8369
-14.6391 -1.7077 -16.7839 -1.0933 0.1432 0.0126
15.0365 2.6376 19.5686 1.2136 -0.2308 -0.1155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.265
_diffrn_reflns_Laue_measured_fraction_max 0.234
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2621
_diffrn_reflns_point_group_measured_fraction_full 0.265
_diffrn_reflns_point_group_measured_fraction_max 0.234
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.812
_diffrn_reflns_theta_min         2.772
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         290000
_diffrn.ambient_pressure_su      20000
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.265
_diffrn_measured_fraction_theta_max 0.234
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  19.00   1.00   35.00    --   27.05  39.00 -12.00   52
  2  ω     -9.00  44.00   1.00   35.00    --   27.05 -39.00-167.00   53
  3  ω     19.00  57.00   1.00   35.00    --   27.05 -77.00  30.00   38
  4  ω     -9.00  13.00   1.00   35.00    --  -27.91 -67.00-157.00   22
  5  ω     25.00  49.00   1.00   35.00    --  -27.91-134.00-123.00   24
  6  ω    -88.00 -25.00   1.00   35.00    --  -27.91 134.00 123.00   63
  7  ω    -19.00  32.00   1.00   35.00    --  -27.91 -39.00  12.00   51
  8  ω    -57.00 -19.00   1.00   35.00    --  -27.91  77.00 150.00   38
  9  ω     25.00  49.00   1.00   35.00    --  -27.91-134.00  56.00   24
 10  ω    -67.00  -4.00   1.00   35.00    --  -27.91  97.00 -35.00   63
 11  ω    -43.00 -11.00   1.00   35.00    --  -27.91  19.00   0.00   32
 12  ω    -44.00  19.00   1.00   35.00    --  -27.91  19.00-180.00   63
 13  ω      4.00  27.00   1.00   35.00    --  -27.91 -97.00  35.00   23
 14  ω    -35.00  19.00   1.00   35.00    --   27.05  19.00-180.00   54
 15  ω    -17.00  14.00   1.00   35.00    --   27.05  53.00 -17.00   31
 16  ω    -17.00  14.00   1.00   35.00    --   27.05  53.00 162.00   31
 17  ω     14.00  67.00   1.00   35.00    --   27.05 -97.00  35.00   53
 18  ω     19.00  57.00   1.00   35.00    --   27.05 -77.00-150.00   38
 19  ω    -50.00 -25.00   1.00   35.00    --   27.05 134.00 -56.00   25
 20  ω    -50.00 -25.00   1.00   35.00    --   27.05 134.00 123.00   25
 21  ω     13.00  35.00   1.00   35.00    --  -27.91-114.00-136.00   22
 22  ω    -54.00 -24.00   1.00   35.00    --  -27.91  37.00   0.00   30
 23  ω    -19.00  32.00   1.00   35.00    --  -27.91 -39.00-167.00   51
 24  ω     -9.00  44.00   1.00   35.00    --   27.05 -39.00  12.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356564000
_diffrn_orient_matrix_UB_12      0.0175252000
_diffrn_orient_matrix_UB_13      0.0322574000
_diffrn_orient_matrix_UB_21      -0.0099969000
_diffrn_orient_matrix_UB_22      -0.1302327000
_diffrn_orient_matrix_UB_23      0.0134402000
_diffrn_orient_matrix_UB_31      0.0260678000
_diffrn_orient_matrix_UB_32      -0.0740327000
_diffrn_orient_matrix_UB_33      -0.0159549000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                171
_reflns_number_total             361
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         361
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1660
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.065
_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/[σ²(Fo²)+(0.0606P)²+3.1946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1842
_refine_special_details          'Crystal measured at pressure of 0.29(2)GPa'
_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-O1
 1.3 with sigma of 0.02
 O2-C7
 1.2 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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1570(16) 0.4040(19) 0.4128(13) 0.046(3) Uiso 1 1 d . . . . .
H1 H 0.2148 0.4487 0.4290 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1300(16) 0.2032(18) 0.4529(14) 0.052(3) Uiso 1 1 d . . . . .
H2 H 0.1682 0.1240 0.4949 0.063 Uiso 1 1 calc R U . . .
C3 C 0.0453(17) 0.1263(19) 0.4284(15) 0.039(3) Uiso 1 1 d . . . . .
C4 C -0.0075(16) 0.2543(19) 0.3672(14) 0.043(3) Uiso 1 1 d . . . . .
H4 H -0.0653 0.2088 0.3503 0.052 Uiso 1 1 calc R U . . .
C5 C 0.0239(15) 0.4553(18) 0.3289(13) 0.049(3) Uiso 1 1 d . . . . .
H5 H -0.0122 0.5360 0.2861 0.059 Uiso 1 1 calc R U . . .
C6 C 0.0128(14) -0.0779(15) 0.4711(12) 0.038(2) Uiso 1 1 d . . . . .
H6A H 0.0568 -0.2165 0.4943 0.046 Uiso 1 1 calc R U . . .
H6B H -0.0361 -0.1790 0.4388 0.046 Uiso 1 1 calc R U . . .
N1 N 0.1099(13) 0.5298(16) 0.3564(11) 0.042(2) Uiso 1 1 d . . . . .
C7 C 0.2404(12) 0.975(2) 0.3219(10) 0.055(4) Uiso 1 1 d D . . . .
C8 C 0.2751(19) 1.204(2) 0.2837(15) 0.047(3) Uiso 1 1 d . . . . .
H8 H 0.3295 1.2785 0.3059 0.056 Uiso 1 1 calc R U . . .
O1 O 0.1625(11) 0.8958(12) 0.2844(9) 0.057(2) Uiso 1 1 d D . . . .
H1A H 0.1461 0.7794 0.3078 0.085 Uiso 1 1 calc R U . . .
O2 O 0.2877(12) 0.8853(15) 0.3780(11) 0.063(3) Uiso 1 1 d D . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.400(13) . ?
C1 N1 1.26(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.38(3) . ?
C3 C4 1.36(4) . ?
C3 C6 1.495(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.417(14) . ?
C5 H5 0.9300 . ?
C5 N1 1.39(3) . ?
C6 C6 1.53(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.535(15) . ?
C7 O1 1.310(17) . ?
C7 O2 1.191(18) . ?
C8 C8 1.37(6) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 117.1 . . ?
N1 C1 H1 117.1 . . ?
N1 C1 C2 126(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C6 120(2) . . ?
C4 C3 C2 118.0(13) . . ?
C4 C3 C6 122(2) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.6 . . ?
N1 C5 C4 119(2) . . ?
N1 C5 H5 120.6 . . ?
C3 C6 C6 110.9(8) . 5_556 ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C6 C6 H6A 109.5 5_556 . ?
C6 C6 H6B 109.5 5_556 . ?
H6A C6 H6B 108.0 . . ?
C1 N1 C5 118.1(12) . . ?
O1 C7 C8 113.2(19) . . ?
O2 C7 C8 117.3(18) . . ?
O2 C7 O1 129.4(14) . . ?
C7 C8 H8 120.5 . . ?
C8 C8 C7 119(3) 7_575 . ?
C8 C8 H8 120.5 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -1.2(15) . . . . ?
C1 C2 C3 C6 -177.4(8) . . . . ?
C2 C1 N1 C5 -3.3(16) . . . . ?
C2 C3 C4 C5 1.5(18) . . . . ?
C2 C3 C6 C6 87(2) . . . 5_556 ?
C3 C4 C5 N1 -2.6(16) . . . . ?
C4 C3 C6 C6 -89(3) . . . 5_556 ?
C4 C5 N1 C1 3.3(13) . . . . ?
C6 C3 C4 C5 177.6(8) . . . . ?
N1 C1 C2 C3 2.2(16) . . . . ?
O1 C7 C8 C8 -1.4(15) . . . 7_575 ?
O2 C7 C8 C8 174.9(13) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_029_final in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.695285   4.701950  19.652064  90.0000 110.0840  90.0000
ZERR    4.00   0.031676   0.000582   0.041666   0.0000   0.2523   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_exptl_crystal_mounting_method 
'Single crystal grown at ambient conditions was mounted in Merrill-Bassett diamond anvil cell, compressed to 0.29(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 2.025
_oxdiff_exptl_absorpt_empirical_full_min 0.627
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_079
_database_code_depnum_ccdc_archive 'CCDC 2340682'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_079          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_079          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.241 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT088_etyfum_079          
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.70 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT149_etyfum_079          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.11 Degree
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the precision of the unit-cell parameter'
;
_vrf_PLAT201_etyfum_079          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_079          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01962 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_079          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        865 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N2, C4 H4 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.758(12)
_cell_length_b                   4.5205(17)
_cell_length_c                   19.83(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.80(11)
_cell_angle_gamma                90
_cell_volume                     1394(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    488
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.1080
_cell_measurement_theta_min      2.7130
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.978
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-20 -3 3 0.0328
-23 1 16 0.0531
-6 5 17 0.0560
17 4 0 0.1520
22 -1 -16 0.1471
10 -5 -18 0.1338
2 -3 17 0.0260
-2 3 -16 0.0090

_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.037
_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)
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-19.8437 -3.1871 3.3230 0.2260 -0.7728 0.5930
-22.8092 0.8941 15.5886 0.2799 -0.9461 -0.1630
-6.4343 5.0729 16.8461 0.1003 -0.3280 -0.9393
17.0386 3.9712 0.3349 -0.1886 0.6479 -0.7380
22.2038 -1.3827 -16.4978 -0.2748 0.9275 0.2536
10.4038 -4.6578 -18.0851 -0.1465 0.4854 0.8619
2.2659 -3.2106 16.8844 -0.8232 -0.2356 0.0537
-2.3587 3.0103 -15.8416 0.7790 0.2134 -0.0473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      298.00
_diffrn_ambient_pressure         790000
_diffrn.ambient_pressure_su      20000
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  63.00   1.00   15.00    --   -0.43-114.00-136.00   58
  2  ω      9.00  38.00   1.00   30.00    --   26.40 -77.00  30.00   29
  3  ω     -6.00  68.00   1.00   30.00    --   26.40 -81.00-151.00   74
  4  ω    -42.00  31.00   1.00   30.00    --   26.40  26.00  -7.00   73
  5  ω     60.00 111.00   1.00   30.00    --   26.40 178.00 -90.00   51
  6  ω     13.00  84.00   1.00   30.00    --   26.40-114.00  44.00   71
  7  ω    -17.00   4.00   1.00   30.00    --   26.40  57.00 120.00   21
  8  ω    -39.00  27.00   1.00   30.00    --   26.40  39.00 -12.00   66
  9  ω    -57.00  22.00   1.00   30.00    --  -27.26  53.00 162.00   79
 10  ω    -38.00  -9.00   1.00   30.00    --  -27.26  77.00 -30.00   29
 11  ω    -27.00  38.00   1.00   30.00    --  -27.26 -39.00  12.00   65
 12  ω    -52.00  27.00   1.00   30.00    --  -27.26  39.00 -12.00   79
 13  ω    -38.00  -9.00   1.00   15.00    --   -0.43  77.00 150.00   29
 14  ω    -37.00  -5.00   1.00   30.00    --   26.40 114.00 136.00   32
 15  ω    -39.00  -6.00   1.00   30.00    --   26.40   0.00-150.00   33
 16  ω     -4.00  16.00   1.00   30.00    --  -27.26 -57.00-150.00   20
 17  ω     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       'ω 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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 0.79(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                185
_reflns_number_total             308
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0851
_refine_ls_restrained_S_all      1.036
_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/[σ²(Fo²)+(0.1660P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2074
_refine_ls_wR_factor_ref         0.2642
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1602(11) 0.395(2) 0.4144(11) 0.043(4) Uiso 1 1 d . . . . .
H1 H 0.2180 0.4477 0.4313 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1326(9) 0.189(2) 0.4535(9) 0.044(4) Uiso 1 1 d . . . . .
H2 H 0.1710 0.1036 0.4957 0.053 Uiso 1 1 calc R U . . .
C3 C 0.0460(10) 0.117(2) 0.4276(9) 0.035(4) Uiso 1 1 d . . . . .
C4 C -0.0093(11) 0.248(3) 0.3665(10) 0.045(4) Uiso 1 1 d . . . . .
H4 H -0.0678 0.2070 0.3496 0.053 Uiso 1 1 calc R U . . .
C5 C 0.0231(9) 0.444(2) 0.3301(9) 0.041(4) Uiso 1 1 d . . . . .
H5 H -0.0144 0.5301 0.2875 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0118(7) -0.086(2) 0.4721(8) 0.041(3) Uiso 1 1 d . . . . .
H6A H -0.0386 -0.1896 0.4398 0.049 Uiso 1 1 calc R U . . .
H6B H 0.0551 -0.2324 0.4968 0.049 Uiso 1 1 calc R U . . .
N1 N 0.1066(8) 0.516(2) 0.3539(7) 0.039(3) Uiso 1 1 d . . . . .
C7 C 0.2444(12) 0.965(2) 0.3239(11) 0.042(4) Uiso 1 1 d . . . . .
C8 C 0.2729(11) 1.199(2) 0.2829(9) 0.040(4) Uiso 1 1 d . . . . .
H8 H 0.3276 1.2772 0.3059 0.048 Uiso 1 1 calc R U . . .
O1 O 0.1634(6) 0.8888(15) 0.2857(6) 0.050(3) Uiso 1 1 d . . . . .
H1A H 0.1460 0.7781 0.3100 0.074 Uiso 1 1 calc R U . . .
O2 O 0.2915(7) 0.8717(17) 0.3805(7) 0.057(3) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.396(14) . ?
C1 N1 1.32(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(18) . ?
C3 C4 1.36(2) . ?
C3 C6 1.524(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(15) . ?
C5 H5 0.9300 . ?
C5 N1 1.340(13) . ?
C6 C6 1.52(2) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.514(15) . ?
C7 O1 1.33(2) . ?
C7 O2 1.18(2) . ?
C8 C8 1.33(3) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(16) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.0(15) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C6 119.7(14) . . ?
C4 C3 C2 120.0(13) . . ?
C4 C3 C6 120.0(15) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(16) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 118.8 . . ?
N1 C5 C4 122.4(15) . . ?
N1 C5 H5 118.8 . . ?
C3 C6 H6A 109.3 . . ?
C3 C6 H6B 109.3 . . ?
C6 C6 C3 111.7(9) 5_556 . ?
C6 C6 H6A 109.3 5_556 . ?
C6 C6 H6B 109.3 5_556 . ?
H6A C6 H6B 107.9 . . ?
C1 N1 C5 119.2(13) . . ?
O1 C7 C8 109.4(16) . . ?
O2 C7 C8 121.7(18) . . ?
O2 C7 O1 128.9(13) . . ?
C7 C8 H8 116.9 . . ?
C8 C8 C7 126(2) 7_575 . ?
C8 C8 H8 116.9 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -1.1(18) . . . . ?
C1 C2 C3 C6 -174.7(10) . . . . ?
C2 C1 N1 C5 1(2) . . . . ?
C2 C3 C4 C5 2(2) . . . . ?
C2 C3 C6 C6 86.1(15) . . . 5_556 ?
C3 C4 C5 N1 -2(2) . . . . ?
C4 C3 C6 C6 -87(2) . . . 5_556 ?
C4 C5 N1 C1 0.1(19) . . . . ?
C6 C3 C4 C5 175.9(8) . . . . ?
N1 C1 C2 C3 -0.7(18) . . . . ?
O1 C7 C8 C8 -3.7(19) . . . 7_575 ?
O2 C7 C8 C8 174.9(13) . . . 7_575 ?


_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_etyfum_185
_database_code_depnum_ccdc_archive 'CCDC 2340686'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_etyfum_185          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT029_etyfum_185          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.293 Why?  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT088_etyfum_185          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.63 Note  
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
_vrf_PLAT201_etyfum_185          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Use of diamond-anvil cell affected number of collected
data making it impossible to refine structure with resonable data/parameter
ratio. For this reason only isotropic refinement was done.'
;
_vrf_PLAT340_etyfum_185          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01338 Ang.  
RESPONSE: 'Use of diamond-anvil cell affected collected data, 
affecting the quality of the final structural model'
;
_vrf_PLAT911_etyfum_185          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        797 Report
RESPONSE: 'Use of diamond-anvil cell affected completness of collected data'
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N2,C4 H4 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.808(6)
_cell_length_b                   4.2460(8)
_cell_length_c                   20.027(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.38(5)
_cell_angle_gamma                90
_cell_volume                     1301.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    756
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.8890
_cell_measurement_theta_min      2.6480
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.973
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
20 -3 -2 0.0328
23 1 -16 0.0531
7 4 -19 0.0560
-17 4 -1 0.1520
-23 -1 17 0.1471
-11 -4 20 0.1338
-2 -3 -16 0.0220
2 3 15 0.0120

_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.036
_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)
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
19.6273 -2.9131 -2.4762 0.2260 -0.7728 0.5930
23.1123 0.7026 -16.2185 0.2799 -0.9461 -0.1630
7.1036 4.4832 -18.7195 0.1003 -0.3280 -0.9393
-16.7033 3.5987 -1.4963 -0.1886 0.6479 -0.7380
-22.5609 -1.1393 17.2912 -0.2748 0.9275 0.2536
-11.0568 -4.0981 19.8674 -0.1465 0.4854 0.8619
-1.7817 -3.3282 -15.8036 -0.8232 -0.2356 0.0537
1.9017 3.1223 14.8254 0.7790 0.2134 -0.0473

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      298
_diffrn_ambient_pressure         1850000
_diffrn.ambient_pressure_su      20000
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  17.00   1.00   15.00    --   -0.27  67.00 -23.00   60
  2  ω     29.00  57.00   1.00   15.00    --   -0.27 -99.00-150.00   28
  3  ω     -8.00  62.00   1.00   30.00    --   26.72 -67.00  23.00   70
  4  ω      2.00  68.00   1.00   30.00    --   26.72 -81.00-151.00   66
  5  ω    -39.00   9.00   1.00   30.00    --   26.72   0.00-150.00   48
  6  ω    -30.00   4.00   1.00   30.00    --   26.72  97.00 -35.00   34
  7  ω    -22.00  11.00   1.00   30.00    --   26.72  81.00 151.00   33
  8  ω    -38.00  -9.00   1.00   30.00    --  -27.26  77.00 -30.00   29
  9  ω     17.00  50.00   1.00   30.00    --  -27.26-134.00-123.00   33
 10  ω   -121.00 -69.00   1.00   30.00    --  -27.26 178.00 -90.00   52
 11  ω    -27.00  38.00   1.00   30.00    --  -27.26 -39.00-167.00   65
 12  ω    -48.00  31.00   1.00   30.00    --  -27.26  26.00  -7.00   79
 13  ω      5.00  37.00   1.00   30.00    --  -27.26-114.00  44.00   32
 14  ω     -4.00  16.00   1.00   30.00    --  -27.26 -57.00  30.00   20
 15  ω    -17.00  16.00   1.00   30.00    --  -27.26 -67.00  23.00   33
 16  ω    -68.00  11.00   1.00   30.00    --  -27.26  81.00 151.00   79
 17  ω    -11.00  22.00   1.00   30.00    --  -27.26 -81.00-151.00   33
 18  ω    -38.00  -9.00   1.00   15.00    --   -0.27  77.00 -60.00   29
 19  ω    -47.00  -9.00   1.00   15.00    --   -0.27  77.00-180.00   38
 20  ω     -4.00  18.00   1.00   30.00    --   26.72 -57.00  60.00   22
 21  ω    -16.00  17.00   1.00   30.00    --   26.72  67.00 157.00   33
 22  ω    -17.00   4.00   1.00   30.00    --   26.72  57.00-180.00   21
 23  ω      9.00  34.00   1.00   30.00    --   26.72 -77.00  60.00   25
 24  ω    -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       'ω 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_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 1.85(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                218
_reflns_number_total             351
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.126
_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/[σ²(Fo²)+(0.0998P)²+1.2687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1976
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1606(7) 0.371(2) 0.4144(6) 0.040(3) Uiso 1 1 d . . . . .
H1 H 0.2201 0.4115 0.4315 0.047 Uiso 1 1 calc R U . . .
C2 C 0.1315(6) 0.1651(15) 0.4540(5) 0.033(2) Uiso 1 1 d . . . . .
H2 H 0.1711 0.0715 0.4968 0.040 Uiso 1 1 calc R U . . .
C3 C 0.0440(6) 0.1028(17) 0.4293(5) 0.025(2) Uiso 1 1 d . . . . .
C4 C -0.0119(6) 0.2441(19) 0.3650(5) 0.033(2) Uiso 1 1 d . . . . .
H4 H -0.0717 0.2059 0.3466 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0214(6) 0.4439(16) 0.3279(5) 0.033(2) Uiso 1 1 d . . . . .
H5 H -0.0164 0.5356 0.2841 0.039 Uiso 1 1 calc R U . . .
C6 C 0.0100(5) -0.0997(15) 0.4725(5) 0.031(2) Uiso 1 1 d . . . . .
H6A H 0.0530 -0.2589 0.4986 0.037 Uiso 1 1 calc R U . . .
H6B H -0.0427 -0.2058 0.4396 0.037 Uiso 1 1 calc R U . . .
N1 N 0.1071(6) 0.5067(14) 0.3542(5) 0.036(2) Uiso 1 1 d . . . . .
C7 C 0.2436(6) 0.9616(17) 0.3219(6) 0.029(2) Uiso 1 1 d . . . . .
C8 C 0.2744(7) 1.1963(18) 0.2828(5) 0.030(2) Uiso 1 1 d . . . . .
H8 H 0.3313 1.2710 0.3062 0.036 Uiso 1 1 calc R U . . .
O1 O 0.1628(4) 0.8890(12) 0.2870(4) 0.0406(16) Uiso 1 1 d . . . . .
H1A H 0.1462 0.7924 0.3144 0.061 Uiso 1 1 calc R U . . .
O2 O 0.2937(4) 0.8549(13) 0.3813(4) 0.0447(19) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.397(9) . ?
C1 N1 1.304(13) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(11) . ?
C3 C4 1.378(13) . ?
C3 C6 1.492(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(9) . ?
C5 H5 0.9300 . ?
C5 N1 1.341(10) . ?
C6 C6 1.531(13) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.485(10) . ?
C7 O1 1.282(11) . ?
C7 O2 1.226(11) . ?
C8 C8 1.311(16) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.9 . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.2(11) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(9) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.1(8) . . ?
C2 C3 C6 120.8(8) . . ?
C4 C3 C6 121.0(9) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(10) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.4 . . ?
N1 C5 C4 121.1(9) . . ?
N1 C5 H5 119.4 . . ?
C3 C6 C6 110.4(6) . 5_556 ?
C3 C6 H6A 109.6 . . ?
C3 C6 H6B 109.6 . . ?
C6 C6 H6A 109.6 5_556 . ?
C6 C6 H6B 109.6 5_556 . ?
H6A C6 H6B 108.1 . . ?
C1 N1 C5 119.5(8) . . ?
O1 C7 C8 113.3(8) . . ?
O2 C7 C8 120.7(9) . . ?
O2 C7 O1 126.0(8) . . ?
C7 C8 H8 118.2 . . ?
C8 C8 C7 123.5(12) 7_575 . ?
C8 C8 H8 118.2 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.8(11) . . . . ?
C1 C2 C3 C6 -176.2(7) . . . . ?
C2 C1 N1 C5 -1.6(14) . . . . ?
C2 C3 C4 C5 -0.3(13) . . . . ?
C2 C3 C6 C6 88.2(10) . . . 5_556 ?
C3 C4 C5 N1 -1.2(12) . . . . ?
C4 C3 C6 C6 -88.7(12) . . . 5_556 ?
C4 C5 N1 C1 2.2(12) . . . . ?
C6 C3 C4 C5 176.8(6) . . . . ?
N1 C1 C2 C3 0.1(13) . . . . ?
O1 C7 C8 C8 -4.2(12) . . . 7_575 ?
O2 C7 C8 C8 175.4(9) . . . 7_575 ?


_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ETYFUM_053
_database_code_depnum_ccdc_archive 'CCDC 2340687'
loop_
_audit_author_name
_audit_author_address
'Ewa Patyk-Kazmierczak'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_ATOM007_ETYFUM_053          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT029_ETYFUM_053          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.293 Why?  
RESPONSE: "Number of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT149_ETYFUM_053          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.30 Degree
RESPONSE: "Quality of data affected by the construction of diamond-anvil cell"
;
_vrf_PLAT201_ETYFUM_053          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: 'Nature of high-pressure experiment hinders 
access to the crystal sample, lowering number of collected data; 
as a result insufficient data/parameter ratio is obtained for 
anisotropic refinement; due to this reason isotropical
refinement was implemented'
;
_vrf_PLAT340_ETYFUM_053          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02625 Ang.  
RESPONSE: "Quality of structural model affected by poor quality and low number 
of experimental data"
;
_vrf_PLAT911_ETYFUM_053          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        868 Report
RESPONSE: ."Number of data affected by the construction of diamond-anvil cell"
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        '1,2-bis(4-Pyridyl)ethane fumaric acid'
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4O4H4, N2C12H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.73(3)
_cell_length_b                   4.5924(6)
_cell_length_c                   19.74(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.9(3)
_cell_angle_gamma                90
_cell_volume                     1417(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    763
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.7710
_cell_measurement_theta_min      2.7020
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.997
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 5 -16 0.1090
-15 5 14 0.1042
-14 -4 18 0.1410
10 -6 -8 0.0709
-14 -2 -17 0.0100
15 2 20 0.0100

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.1499 4.7878 -16.4715 -0.0273 -0.9790 0.2019
-14.9022 4.6416 13.9988 -0.0038 -0.2745 -0.9616
-13.5976 -4.3592 17.8446 0.0270 0.9555 -0.2938
10.2877 -5.7534 -8.1600 0.0117 0.5472 0.8369
-14.4336 -1.5493 -16.8815 -1.0933 0.1432 0.0126
14.8409 2.4494 19.6833 1.2136 -0.2308 -0.1155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_Laue_measured_fraction_full 0.293
_diffrn_reflns_Laue_measured_fraction_max 0.259
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3104
_diffrn_reflns_point_group_measured_fraction_full 0.293
_diffrn_reflns_point_group_measured_fraction_max 0.259
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.003
_diffrn_reflns_theta_min         2.751
_diffrn_ambient_temperature      298.00
_diffrn_ambient_pressure         530000
_diffrn.ambient_pressure_su      20000
_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 0.259
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  70.00   1.00   30.00    --   27.05 -97.00  35.00   60
  2  ω    -32.00  22.00   1.00   30.00    --   27.05  39.00 -12.00   54
  3  ω      4.00  63.00   1.00   30.00    --   27.05 -81.00-151.00   59
  4  ω    -36.00 -10.00   1.00   30.00    --   27.05 114.00 -44.00   26
  5  ω    -15.00  47.00   1.00   30.00    --   27.05 -19.00-180.00   62
  6  ω    -18.00   9.00   1.00   30.00    --   27.05  77.00 150.00   27
  7  ω    -26.00  43.00   1.00   30.00    --  -27.91 -26.00   7.00   69
  8  ω     10.00  35.00   1.00   30.00    --  -27.91-114.00-136.00   25
  9  ω    -57.00  12.00   1.00   30.00    --  -27.91  67.00 -23.00   69
 10  ω    -47.00  22.00   1.00   30.00    --  -27.91  19.00-180.00   69
 11  ω      5.00  29.00   1.00   30.00    --  -27.91 -99.00  30.00   24
 12  ω    -36.00 -10.00   1.00   30.00    --   27.05 114.00 136.00   26
 13  ω    -23.00  39.00   1.00   30.00    --   27.05 -13.00   3.00   62
 14  ω    -70.00  -1.00   1.00   30.00    --  -27.91  97.00 143.00   69
 15  ω    -22.00  32.00   1.00   30.00    --  -27.91 -39.00  12.00   54
 16  ω   -111.00 -78.00   1.00   30.00    --  -27.91 178.00 -90.00   33
 17  ω    -11.00  37.00   1.00   30.00    --  -27.91 -37.00-180.00   48
 18  ω    -12.00  13.00   1.00   30.00    --  -27.91 -67.00  23.00   25
 19  ω    -35.00  35.00   1.00   30.00    --  -27.91   0.00-180.00   70
 20  ω    -22.00  32.00   1.00   30.00    --  -27.91 -39.00-167.00   54
 21  ω    -35.00  -7.00   1.00   30.00    --  -27.91   0.00-180.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0358462000
_diffrn_orient_matrix_UB_12      0.0157276000
_diffrn_orient_matrix_UB_13      0.0326719000
_diffrn_orient_matrix_UB_21      -0.0107799000
_diffrn_orient_matrix_UB_22      -0.1326980000
_diffrn_orient_matrix_UB_23      0.0129148000
_diffrn_orient_matrix_UB_31      0.0257566000
_diffrn_orient_matrix_UB_32      -0.0771639000
_diffrn_orient_matrix_UB_33      -0.0156863000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          'Crystal measured at pressure of 0.53(2)GPa'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                200
_reflns_number_total             401
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         401
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1835
_refine_ls_R_factor_gt           0.0763
_refine_ls_restrained_S_all      1.027
_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/[σ²(Fo²)+(0.0610P)²+3.5496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1803
_refine_special_details          ?
_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
 O1-C7
 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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1582(13) 0.3984(18) 0.4136(11) 0.041(3) Uiso 1 1 d . . . . .
H1 H 0.2159 0.4473 0.4300 0.049 Uiso 1 1 calc R U . . .
C2 C 0.1306(14) 0.1940(16) 0.4536(12) 0.047(3) Uiso 1 1 d . . . . .
H2 H 0.1690 0.1095 0.4954 0.056 Uiso 1 1 calc R U . . .
C3 C 0.0458(14) 0.1234(17) 0.4293(12) 0.034(2) Uiso 1 1 d . . . . .
C4 C -0.0098(13) 0.2492(17) 0.3652(12) 0.033(2) Uiso 1 1 d . . . . .
H4 H -0.0675 0.1998 0.3473 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0225(13) 0.4492(17) 0.3286(12) 0.047(3) Uiso 1 1 d . . . . .
H5 H -0.0137 0.5339 0.2859 0.056 Uiso 1 1 calc R U . . .
C6 C 0.0129(11) -0.0810(14) 0.4732(10) 0.034(2) Uiso 1 1 d . . . . .
H6A H -0.0358 -0.1880 0.4410 0.040 Uiso 1 1 calc R U . . .
H6B H 0.0572 -0.2203 0.4981 0.040 Uiso 1 1 calc R U . . .
N1 N 0.1075(12) 0.5222(14) 0.3551(10) 0.037(2) Uiso 1 1 d . . . . .
C7 C 0.2426(10) 0.972(2) 0.3225(9) 0.049(3) Uiso 1 1 d D . . . .
C8 C 0.2759(15) 1.2036(18) 0.2844(12) 0.040(3) Uiso 1 1 d . . . . .
H8 H 0.3301 1.2825 0.3068 0.048 Uiso 1 1 calc R U . . .
O1 O 0.1634(9) 0.8942(11) 0.2855(7) 0.050(2) Uiso 1 1 d D . . . .
H1A H 0.1473 0.7773 0.3093 0.075 Uiso 1 1 calc R U . . .
O2 O 0.2893(10) 0.8797(14) 0.3791(9) 0.057(2) Uiso 1 1 d D . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.407(11) . ?
C1 N1 1.30(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.37(3) . ?
C3 C4 1.40(3) . ?
C3 C6 1.508(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(12) . ?
C5 H5 0.9300 . ?
C5 N1 1.37(3) . ?
C6 C6 1.479(17) 5_556 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.516(13) . ?
C7 O1 1.315(16) . ?
C7 O2 1.191(17) . ?
C8 C8 1.39(5) 7_575 ?
C8 H8 0.9300 . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.2 . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.6(18) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.9(19) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 119.5(11) . . ?
C2 C3 C6 119(2) . . ?
C4 C3 C6 121.0(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(19) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.8 . . ?
N1 C5 C4 120(2) . . ?
N1 C5 H5 119.8 . . ?
C3 C6 H6A 109.4 . . ?
C3 C6 H6B 109.4 . . ?
C6 C6 C3 111.0(7) 5_556 . ?
C6 C6 H6A 109.4 5_556 . ?
C6 C6 H6B 109.4 5_556 . ?
H6A C6 H6B 108.0 . . ?
C1 N1 C5 119.5(10) . . ?
O1 C7 C8 113.0(17) . . ?
O2 C7 C8 118.8(16) . . ?
O2 C7 O1 128.2(12) . . ?
C7 C8 H8 120.4 . . ?
C8 C8 C7 119(2) 7_575 . ?
C8 C8 H8 120.4 7_575 . ?
C7 O1 H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.6(14) . . . . ?
C1 C2 C3 C6 -176.3(7) . . . . ?
C2 C1 N1 C5 -1.6(15) . . . . ?
C2 C3 C4 C5 -1.5(15) . . . . ?
C2 C3 C6 C6 89(2) . . . 5_556 ?
C3 C4 C5 N1 -0.1(14) . . . . ?
C4 C3 C6 C6 -89(3) . . . 5_556 ?
C4 C5 N1 C1 1.7(13) . . . . ?
C6 C3 C4 C5 176.4(7) . . . . ?
N1 C1 C2 C3 -0.1(14) . . . . ?
O1 C7 C8 C8 -3.3(13) . . . 7_575 ?
O2 C7 C8 C8 174.8(10) . . . 7_575 ?


_ins_header                      
;
TITL ETYFUM_058_32 in I2/a 
REM I2/a (#15 in standard setting)
CELL 0.71073  16.729891   4.592376  19.744091  90.0000 110.8647  90.0000
ZERR    4.00   0.029791   0.000606   0.042637   0.0000   0.2496   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_exptl_crystal_mounting_method 
'Single crystal grown at ambient conditions was mounted in Merrill-Bassett diamond anvil cell, compressed to 0.53(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 2.282
_oxdiff_exptl_absorpt_empirical_full_min 0.696
