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_4512841
_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         'C21 H16 Br N O4'
_chemical_formula_sum            'C21 H16 Br N O4'
_chemical_formula_weight         426.26
_chemical_name_systematic
; 
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.325(5)
_cell_angle_beta                 81.672(4)
_cell_angle_gamma                75.385(7)
_cell_formula_units_Z            2
_cell_length_a                   6.6580(4)
_cell_length_b                   10.5799(11)
_cell_length_c                   13.4275(4)
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5670
_cell_measurement_theta_min      3.3080
_cell_volume                     905.54(12)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3259
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.000
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.332
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.877
_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    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.1291
_exptl_crystal_size_mid          0.0288
_exptl_crystal_size_min          0.0258
_refine_diff_density_max         3.255
_refine_diff_density_min         -1.395
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       0.0039(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0909
_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^)+(0.1485P)^2^+7.3958P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2754
_refine_ls_wR_factor_ref         0.2798
_reflns_number_gt                2816
_reflns_number_total             3259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmlg_compound_4
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_original_cell_volume        905.55(12)
_cod_database_code               4512841
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C1-Br1 \\sim C1-Br1A \\sim C1-Br1B
 with sigma of 0.01
3. Others
 1*[Sof(Br1)]+1*[Sof(Br1B)]+1*[Sof(Br1A)]=1 with esd of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C18(H18), C5(H5), C17(H17), C14(H14), C19(H19),
 C13(H13), C12(H12), C21(H21), C20(H20)
;
_shelxl_version_number           2013-2