Novel solid forms of lonidamine: crystal structures and physicochemical properties
Mapp, Lucy K.; Coles, Simon; Aitipamula, Srinivasulu; CrystEngComm  (2017) –; doi:10.1039/C7CE00651A

data_7228134
_publ_section_title
;
 Novel solid forms of lonidamine: crystal structures and physicochemical
 properties
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00651A
_journal_year                    2017
_chemical_formula_moiety         'C15 H9 Cl2 N2 O2, C3 H7 N6'
_chemical_formula_sum            'C18 H16 Cl2 N8 O2'
_chemical_formula_weight         447.29
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                99.416(5)
_cell_angle_beta                 100.168(5)
_cell_angle_gamma                94.778(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0752(4)
_cell_length_b                   8.1750(4)
_cell_length_c                   16.8057(10)
_cell_measurement_reflns_used    8211
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.6960
_cell_measurement_theta_min      3.2140
_cell_volume                     937.56(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -32.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548  -90.0000   24.0000 93

  2 omega  -31.00   17.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8236  -90.0000   24.0000 48

  3 omega  -62.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.8236   90.0000  139.0000 74

  4 omega  -60.00   56.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548  -77.0000  -90.0000 116

  5 omega  -55.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548  -57.0000  120.0000 107

  6 omega  -13.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548   77.0000    0.0000 109

  7 omega  -10.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3548   57.0000 -120.0000 107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.1022975000
_diffrn_orient_matrix_UB_12      -0.0122362000
_diffrn_orient_matrix_UB_13      -0.0058627000
_diffrn_orient_matrix_UB_21      -0.0042312000
_diffrn_orient_matrix_UB_22      -0.0484724000
_diffrn_orient_matrix_UB_23      -0.0394790000
_diffrn_orient_matrix_UB_31      0.0055844000
_diffrn_orient_matrix_UB_32      -0.0730777000
_diffrn_orient_matrix_UB_33      0.0175642000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.542
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1208
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0380P)^2^+0.7048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3862
_reflns_number_total             4299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-MEL
_cod_original_cell_volume        937.57(9)
_cod_database_code               7228134
_chemical_oxdiff_formula         'C18 H16 N8 O2 Cl2'
_chemical_oxdiff_usercomment     L3-03-B
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15)
;
_shelx_res_checksum              85314
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-13
_olex2_exptl_crystal_mounting_method 'MiTeGen micromesh'
_olex2_submission_original_sample_id L3-03-B
_olex2_submission_special_instructions 'No special instructions were received'