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_4512843
_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         '2(C24 H18 N O4)'
_chemical_formula_sum            'C48 H36 N2 O8'
_chemical_formula_weight         768.79
_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                88.546(7)
_cell_angle_beta                 85.079(7)
_cell_angle_gamma                82.955(6)
_cell_formula_units_Z            2
_cell_length_a                   9.6784(6)
_cell_length_b                   10.0930(8)
_cell_length_c                   19.0710(19)
_cell_measurement_reflns_used    1859
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.39
_cell_measurement_theta_min      4.661
_cell_volume                     1841.8(3)
_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
;
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 10.3271
_diffrn_measured_fraction_theta_full 0.9862
_diffrn_measured_fraction_theta_max 0.9455
_diffrn_measurement_details
;
  1 omega  -88.00   -2.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  -90.0000 86

  2 omega  -28.00   65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573  -57.0000   60.0000 93

  3 omega   15.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   57.0000 -150.0000 94

  4 omega   43.00  132.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -77.0000 -120.0000 89

  5 omega   43.00   99.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -45.0000   60.0000 56

  6 omega   30.00   78.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -30.0000  -60.0000 48

  7 omega   30.00   91.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -30.0000    0.0000 61

  8 omega   46.00  109.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000 -180.0000 63

  9 omega   44.00  109.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000   60.0000 65

 10 omega   27.00   53.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000  -30.0000 26

 11 omega   84.00  109.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000  -30.0000 25

 12 omega   34.00   80.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -30.0000  150.0000 46

 13 omega   93.00  133.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   45.0000 -180.0000 40

 14 omega  139.00  166.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   45.0000 -180.0000 27

 15 omega   36.00  140.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -15.0000 -180.0000 104
;
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0088245000
_diffrn_orient_matrix_UB_12      -0.0212145000
_diffrn_orient_matrix_UB_13      0.0804657000
_diffrn_orient_matrix_UB_21      -0.0207276000
_diffrn_orient_matrix_UB_22      -0.1472382000
_diffrn_orient_matrix_UB_23      -0.0093681000
_diffrn_orient_matrix_UB_31      0.1593620000
_diffrn_orient_matrix_UB_32      -0.0391164000
_diffrn_orient_matrix_UB_33      -0.0035866000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_av_unetI/netI     0.123
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11316
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.883
_diffrn_reflns_theta_min         4.415
_diffrn_source                   'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.894
_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    1.386
_exptl_crystal_description
;
;
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.118
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0051P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.132
_reflns_number_gt                4117
_reflns_number_total             7178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmlh_compound_6
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_database_code               4512843
_chemical_oxdiff_formula         'C48 H36 N2 O8'
_chemical_oxdiff_usercomment
'OADMLH #12632 LIGHT FOMBLIN ON MICROMOUNT FOR ADM/MS'
_reflns_odcompleteness_completeness 98.62
_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
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C11(H11A,H11B), C42(H42A,H42B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C29(H29), C1(H1), C8(H8), C5(H5), C27(H27), C25(H25), C3(H3),
 C15(H15), C37(H37), C14(H14), C13(H13), C45(H45), C48(H48), C44(H44), C24(H24),
  C41(H41), C16(H16), C47(H47), C22(H22), C17(H17), C20(H20), C39(H39),
 C23(H23), C38(H38), C46(H46), C21(H21), C40(H40)
;
_shelxl_version_number           2013-2