Tailored supramolecular gel and microemulsion crystallization strategies – is isoniazid really monomorphic?
Kennedy, Stuart R.; Jones, Christopher D.; Yufit, Dmitry S.; Nicholson, Catherine E.; Cooper, Sharon J.; Steed, Jonathan W.; CrystEngComm 20 (2018) 1390–; doi:10.1039/C8CE00066B

data_7230114
_publ_section_title
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 Tailored supramolecular gel and microemulsion crystallization strategies
 -- is isoniazid really monomorphic?
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_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1390
_journal_paper_doi               10.1039/C8CE00066B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C26 H30 N8 O4, C4 H10 O'
_chemical_formula_sum            'C30 H40 N8 O5'
_chemical_formula_weight         592.70
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.18 svn.r3084 for OlexSys, GUI svn.r4945)
;
_audit_update_record
;
2018-01-15 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
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_cell_angle_alpha                95.908(4)
_cell_angle_beta                 98.689(3)
_cell_angle_gamma                94.564(4)
_cell_formula_units_Z            8
_cell_length_a                   16.066(5)
_cell_length_b                   16.264(5)
_cell_length_c                   25.721(8)
_cell_measurement_reflns_used    7186
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      2.17
_cell_volume                     6577(4)
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.30C (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  DLS
_diffrn_measurement_method       \w-scan
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.2242
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            24292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.37
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0837 after correction.
The Ratio of minimum to maximum transmission is 0.5729.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1560
_refine_ls_number_reflns         24292
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1927
_refine_ls_R_factor_gt           0.0879
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2278
_reflns_number_gt                10164
_reflns_number_total             24292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce00066b2.cif
_cod_data_source_block           2_BuOH_14srv253
_cod_depositor_comments
'Adding full bibliography for 7230114--7230119.cif.'
_cod_database_code               7230114
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C23S-C22S \\sim C21S-C22S \\sim C21S-C22S
 with sigma of 0.005
 C31S-C32S \\sim C33S-C32S \\sim C33K-C32K \\sim C33K-C34K \\sim C33S-C34S
 with sigma of 0.005
 C21S-C22K \\sim C21S-C22S \\sim C23K-C22K \\sim C23S-C22S \\sim C23K-C24K
\\sim C23S-C24S
 with sigma of 0.005
3. Others
 Fixed Sof: C4CB(0.6) H4CB(0.6) C5CB(0.6) H5CB(0.6) C6CB(0.6) H6CB(0.6)
 C22S(0.7) H22A(0.7) H22B(0.7) C23S(0.7) H23D(0.7) H23E(0.7) H4SA(0.5) H4S(0.5)
 C32K(0.5) H32A(0.5) H32B(0.5) C33S(0.5) H33A(0.5) H33B(0.5) C34K(0.5)
 H34A(0.5) H34B(0.5) H34C(0.5) C33K(0.5) H33C(0.5) H33D(0.5) C6CA(0.4)
 H6CA(0.4) C5CA(0.4) H5CA(0.4) C4CA(0.4) H4CA(0.4) C24K(0.3) H24D(0.3)
 H24E(0.3) H24F(0.3) C34S(0.5) H34D(0.5) H34E(0.5) H34F(0.5) C32S(0.5)
 H32C(0.5) H32D(0.5) C23K(0.3) H23F(0.3) H23G(0.3) C22K(0.3) H22C(0.3)
 H22D(0.3) C24S(0.7) H24G(0.7) H24H(0.7) H24I(0.7)
4.a Riding coordinates:
 N2B(H2B), N6B(H6B)
4.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C11S(H11A,H11B), C12S(H12A,
 H12B), C13S(H13D,H13E), C21S(H21A,H21B), C22S(H22A,H22B), C23S(H23D,H23E),
 C31S(H31A,H31B), C32K(H32A,H32B), C33S(H33A,H33B), C33K(H33C,H33D), C32S(H32C,
 H32D), C23K(H23F,H23G), C22K(H22C,H22D)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N5(H5), N6(H6), N7(H7), C2(H2A), C4(H4), C5(H5A),
 C6(H6A), C13(H13), C14(H14), C15(H15), C16(H16), C23(H23), C24(H24), C25(H25),
 C26(H26), N1A(H1A), N2A(H2AA), N3A(H3A), N5A(H5AA), N6A(H6AA), N7A(H7A),
 C2A(H2AB), C4A(H4A), C5A(H5AB), C6A(H6AB), C13A(H13A), C14A(H14A), C15A(H15A),
 C16A(H16A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A), N1B(H1B), N3B(H3B),
  N5B(H5B), N7B(H7B), C2B(H2BA), C4B(H4B), C5B(H5BA), C6B(H6BA), C13B(H13B),
 C14B(H14B), C15B(H15B), C16B(H16B), C23B(H23B), C24B(H24B), C25B(H25B),
 C26B(H26B), N1C(H1C), N2C(H2C), N3C(H3C), N5C(H5C), N6C(H6C), N7C(H7C),
 C2C(H2CA), C4CB(H4CB), C5CB(H5CB), C6CB(H6CB), C13C(H13C), C14C(H14C),
 C15C(H15C), C16C(H16C), C23C(H23C), C24C(H24C), C25C(H25C), C26C(H26C),
 C6CA(H6CA), C5CA(H5CA), C4CA(H4CA)
4.d Tetrahedral OH refined with riding coordinates:
 O4S(H4SA), O4S(H4S)
4.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C18(H18D,H18E,H18F), C19(H19D,H19E,H19F),
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C18A(H18G,H18H,H18I), C19A(H19G,H19H,
 H19I), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC), C18B(H18J,H18K,H18L),
 C19B(H19J,H19K,H19L), C8C(H8CA,H8CB,H8CC), C9C(H9CA,H9CB,H9CC), C18C(H18A,H18B,
 H18C), C19C(H19A,H19B,H19C), C4S(H4SB,H4SC,H4SD), C14S(H14D,H14E,H14F),
 C34K(H34A,H34B,H34C), C24K(H24D,H24E,H24F), C34S(H34D,H34E,H34F), C24S(H24G,
 H24H,H24I)
4.f Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O2S(H2S), O3S(H3S)
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_olex2_submission_special_instructions 'No special instructions were received'