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_4512838
_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         'C9 H8 Br N O4'
_chemical_formula_sum            'C9 H8 Br N O4'
_chemical_formula_weight         274.07
_chemical_name_systematic
'tetramethyl 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                98.438(10)
_cell_angle_beta                 93.014(9)
_cell_angle_gamma                97.680(9)
_cell_formula_units_Z            4
_cell_length_a                   3.9543(4)
_cell_length_b                   13.6225(17)
_cell_length_c                   18.749(2)
_cell_measurement_reflns_used    2503
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.30
_cell_measurement_theta_min      3.73
_cell_volume                     987.38(19)
_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 0.9952
_diffrn_measured_fraction_theta_max 0.9653
_diffrn_measurement_details
;
  1 omega  -50.00   32.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   90.0000 41

  2 omega  -62.00   30.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 46

  3 omega  -80.00  -16.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  120.0000 32

  4 omega   23.00   49.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002 -125.0000  -90.0000 13

  5 omega   76.00  102.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002 -133.0000  145.0000 13

  6 omega   91.00  119.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -120.0000 14

  7 omega   37.00   83.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -120.0000 23

  8 omega   40.00  128.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -61.0000    0.0000 44

  9 omega  103.00  131.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  125.0000  -90.0000 14

 10 omega   48.00  104.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  -30.0000 28

 11 omega  142.00  170.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  125.0000  -90.0000 14

 12 omega   95.00  177.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000   90.0000 41

 13 omega   96.00  160.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000   30.0000 32

 14 omega   31.00  109.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000 -120.0000 39

 15 omega   62.00   88.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   30.0000 13

 16 omega   33.00   81.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -90.0000 24

 17 omega   46.00   88.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -180.0000 21

 18 omega   68.00   96.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000 -150.0000 14

 19 omega   33.00   91.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0312911000
_diffrn_orient_matrix_UB_12      0.0191850000
_diffrn_orient_matrix_UB_13      0.0832869000
_diffrn_orient_matrix_UB_21      -0.1013331000
_diffrn_orient_matrix_UB_22      0.1052108000
_diffrn_orient_matrix_UB_23      -0.0006951000
_diffrn_orient_matrix_UB_31      -0.3796548000
_diffrn_orient_matrix_UB_32      -0.0436646000
_diffrn_orient_matrix_UB_33      0.0006814000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_unetI/netI     0.045
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6326
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.668
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.673
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.568
_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    1.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.75
_refine_diff_density_rms         0.10
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.040P)^2^+0.301P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3267
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmld_compound_1
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_original_cell_volume        987.4(2)
_cod_database_code               4512838
_chemical_oxdiff_formula         'C9 H8 N Br O4'
_chemical_oxdiff_usercomment
'OADMLD #12580 LIGHT FOMBLIN ON MICROMOUNT FOR ADM/MS'
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C5(H5), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelxl_version_number           2013-2