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_4512840
_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         'C13 H16 Br N O4'
_chemical_formula_sum            'C13 H16 Br N O4'
_chemical_formula_weight         330.18
_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     direct
_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                 99.456(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4027(4)
_cell_length_b                   4.51826(15)
_cell_length_c                   27.8897(11)
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.52
_cell_measurement_theta_min      4.458
_cell_volume                     1417.36(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9797
_diffrn_measurement_details
;
  1 omega -100.00  -18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000 -150.0000 82

  2 omega  -44.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   30.0000 77

  3 omega  -64.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  150.0000 86

  4 omega   24.00   52.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002 -125.0000   30.0000 28

  5 omega   53.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6002 -125.0000   30.0000 27

  6 omega   62.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   60.0000 29

  7 omega   59.00  110.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000 -150.0000 51

  8 omega   60.00  110.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  -60.0000 50

  9 omega  146.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   15.0000   60.0000 31

 10 omega   36.00   87.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000    0.0000 51

 11 omega   93.00  170.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  120.0000 77

 12 omega   75.00  120.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -180.0000 45

 13 omega  104.00  156.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  125.0000  -60.0000 52

 14 omega   41.00   86.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -90.0000 45

 15 omega   33.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  150.0000 58

 16 omega   67.00  128.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   15.0000   60.0000 61

 17 omega   41.00   89.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -150.0000 48

 18 omega   39.00  134.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000    0.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1102716000
_diffrn_orient_matrix_UB_12      -0.0157419000
_diffrn_orient_matrix_UB_13      -0.0252757000
_diffrn_orient_matrix_UB_21      0.0779045000
_diffrn_orient_matrix_UB_22      0.1167890000
_diffrn_orient_matrix_UB_23      0.0465411000
_diffrn_orient_matrix_UB_31      0.0229522000
_diffrn_orient_matrix_UB_32      -0.3198496000
_diffrn_orient_matrix_UB_33      0.0182458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.033
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8675
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.528
_diffrn_reflns_theta_min         3.213
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.055
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.469
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description
;
;
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0307
_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^+0.572P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2453
_reflns_number_total             2851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmlf_compound_3
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_database_code               4512840
_chemical_oxdiff_formula         'C13 H16 N O4 Br'
_chemical_oxdiff_usercomment
'OADMLF #12585 LIGHT FOMBLIN ON MICROMOUNT FOR ADM/MS'
_reflns_odcompleteness_completeness 99.83
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C9-C8 \\sim C9A-C8
 with sigma of 0.02
 C10-C9A \\sim C10-C9
 with sigma of 0.02
3. Others
 Sof(H8AA)=Sof(H8AB)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H10B)=Sof(H10C)=Sof(H10A)=1-
 FVAR(1)
 Sof(H8BC)=Sof(H8BD)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H10F)=Sof(H10E)=
 Sof(H10D)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C8(H8AA,H8AB), C8(H8BC,H8BD), C9(H9A,H9B),
 C9A(H9AA,H9AB)
4.b Me refined with riding coordinates:
 C10(H10B,H10C,H10A), C10(H10F,H10E,H10D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelxl_version_number           2013-2