Hirshfeld Surface Investigation of Structure-Directing Interactions within Dipicolinic Acid Derivatives.
Martin, Adam D.; Britton, Joshua; Easun, Timothy L.; Blake, Alexander J.; Lewis, William; Schröder, Martin; Crystal growth & design 15 (2015) 1697–1706; doi:10.1021/cg5016934

data_4512842
_publ_section_title
;
 Hirshfeld Surface Investigation of Structure-Directing Interactions
 within Dipicolinic Acid Derivatives.
;
_journal_issue                   4
_journal_name_full               'Crystal growth &amp; design'
_journal_page_first              1697
_journal_page_last               1706
_journal_paper_doi               10.1021/cg5016934
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C28 H28 N2 O8'
_chemical_formula_sum            'C28 H28 N2 O8'
_chemical_formula_weight         520.52
_chemical_name_systematic
'?tetraethyl 4,4'-(1,4-phenylene)bis(pyridine-2,6-dicarboxylate)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-08-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                113.673(7)
_cell_angle_beta                 92.345(6)
_cell_angle_gamma                107.500(6)
_cell_formula_units_Z            1
_cell_length_a                   6.7914(4)
_cell_length_b                   10.0137(7)
_cell_length_c                   10.9532(10)
_cell_measurement_reflns_used    2279
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.45
_cell_measurement_theta_min      4.49
_cell_volume                     639.40(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.9948
_diffrn_measured_fraction_theta_max 0.9572
_diffrn_measurement_details
;
  1 omega  -50.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -150.0000 83

  2 omega   -2.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -60.0000 36

  3 omega -107.00  -14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   60.0000 93

  4 omega  -46.00  -16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -60.0000 30

  5 omega  -91.00   -2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  -90.0000 89

  6 omega   37.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6627 -125.0000 -180.0000 28

  7 omega   36.00   62.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000    0.0000 26

  8 omega   47.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -180.0000 30

  9 omega   34.00   68.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000    0.0000 34

 10 omega   45.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -120.0000 67

 11 omega   47.00   84.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  -90.0000 37

 12 omega   36.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -60.0000 62

 13 omega   28.00  146.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -15.0000   30.0000 118

 14 omega   41.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -61.0000   60.0000 79

 15 omega   75.00  118.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000    0.0000 43

 16 omega   63.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000   30.0000 40

 17 omega   48.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -150.0000 35

 18 omega   66.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000 -120.0000 25

 19 omega  110.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000    0.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0090878000
_diffrn_orient_matrix_UB_12      -0.0396269000
_diffrn_orient_matrix_UB_13      -0.1518137000
_diffrn_orient_matrix_UB_21      0.2308312000
_diffrn_orient_matrix_UB_22      0.0089630000
_diffrn_orient_matrix_UB_23      0.0135600000
_diffrn_orient_matrix_UB_31      -0.0721968000
_diffrn_orient_matrix_UB_32      -0.1744086000
_diffrn_orient_matrix_UB_33      -0.0344904000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4245
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.277
_diffrn_reflns_theta_min         4.485
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.1051
_exptl_crystal_size_min          0.0552
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.1671P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                2253
_reflns_number_total             2503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmlc_compound_5
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_original_cell_volume        639.40(9)
_cod_database_code               4512842
_chemical_oxdiff_formula         'C28 H28 O8 N2'
_chemical_oxdiff_usercomment
'OADMLC #12577 LIGHT FOMBLIN ON MICROMOUNT FOR ADM/MS'
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C8(H8), C1(H1)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_shelxl_version_number           2013-2