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_4512839
_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         'C11 H12 Br N O4'
_chemical_formula_sum            'C11 H12 Br N O4'
_chemical_formula_weight         302.13
_chemical_name_systematic        'diethyl 4-bromopyridine-2,6-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_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                90
_cell_angle_beta                 110.046(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3907(6)
_cell_length_b                   4.33847(15)
_cell_length_c                   19.5380(8)
_cell_measurement_reflns_used    7847
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.4750
_cell_measurement_theta_min      4.4900
_cell_volume                     1225.56(9)
_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 0.9988
_diffrn_measured_fraction_theta_max 0.9882
_diffrn_measurement_details
;
  1 omega   -9.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000 -150.0000 42

  2 omega  -40.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -150.0000 69

  3 omega  -46.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -30.0000 79

  4 omega   80.00  117.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -180.0000 37

  5 omega   95.00  171.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  125.0000  150.0000 76

  6 omega   37.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 52

  7 omega   86.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  -90.0000 89

  8 omega   36.00   96.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -90.0000 60

  9 omega   41.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  150.0000 53

 10 omega   63.00   95.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000 -150.0000 32

 11 omega   18.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002   57.0000  -30.0000 94

 12 omega   18.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002   57.0000   90.0000 94

 13 omega   18.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002   57.0000 -150.0000 94

 14 omega   85.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000    0.0000 93

 15 omega   76.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000 -150.0000 101

 16 omega   36.00  122.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000  -60.0000 86

 17 omega   35.00  136.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000   60.0000 101

 18 omega   80.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   61.0000  150.0000 94

 19 omega   66.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   15.0000  120.0000 112

 20 omega    1.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002  -99.0000   60.0000 81

 21 omega   18.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002   57.0000  -90.0000 94

 22 omega   13.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002   77.0000  120.0000 102

 23 omega   83.00  148.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  -60.0000 65

 24 omega   80.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   61.0000   30.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0581290000
_diffrn_orient_matrix_UB_12      -0.1882396000
_diffrn_orient_matrix_UB_13      0.0354785000
_diffrn_orient_matrix_UB_21      -0.0820301000
_diffrn_orient_matrix_UB_22      0.0034931000
_diffrn_orient_matrix_UB_23      -0.0725001000
_diffrn_orient_matrix_UB_31      0.0352629000
_diffrn_orient_matrix_UB_32      -0.3009964000
_diffrn_orient_matrix_UB_33      -0.0231369000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_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            14024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.656
_diffrn_reflns_theta_min         3.177
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.630
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.226
_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    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.9173
_exptl_crystal_size_mid          0.0903
_exptl_crystal_size_min          0.0459
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.5189P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2336
_reflns_number_total             2493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmlb_compound_2
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_original_cell_volume        1225.56(8)
_cod_database_code               4512839
_nottingham_internal_coll_name   OADMLB
_nottingham_internal_coll_number 12576
_nottingham_internal_coll_client JB/ADM/MS
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '2 and 8'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   ADM
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user ADM
_nottingham_internal_solution_user DMK/WL
_nottingham_internal_refinement_user DMK/WL
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 26/9/2013
_nottingham_internal_archive_date 26/9/2013
_chemical_oxdiff_formula         'C11 H12 O4 Br N'
_chemical_oxdiff_usercomment
'OADMLB #12576 IN FOMBLIN FILM ON MICROMOUNT FOR ADM/MS'
_reflns_odcompleteness_completeness 99.88
_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:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_shelxl_version_number           2013-2