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

data_7228136
_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, C7 H11 N2, 2(H2 O)'
_chemical_formula_sum            'C22 H24 Cl2 N4 O4'
_chemical_formula_weight         479.35
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.214(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0507(2)
_cell_length_b                   9.0330(2)
_cell_length_c                   19.0712(4)
_cell_measurement_reflns_used    11180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.3920
_cell_measurement_theta_min      3.0370
_cell_volume                     2219.24(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_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
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00   5.00   0.50   20.00    --   21.04 -20.00-113.00  134
  2  \w    -12.00  49.00   0.50   20.00    --  -21.98  20.00  53.00  122
  3  \w    -39.00 -13.00   0.50   20.00    --  -21.98 -20.00-113.00   52
  4  \w     -9.00  97.00   0.50   20.00    --   21.04  57.00-180.00  212
  5  \w    -10.00  34.00   0.50   20.00    --   21.04 -38.00-150.00   88
  6  \w    -48.00  54.00   0.50   20.00    --  -21.98  57.00 -90.00  204
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0167901000
_diffrn_orient_matrix_UB_12      -0.0183010000
_diffrn_orient_matrix_UB_13      0.0361572000
_diffrn_orient_matrix_UB_21      0.0523276000
_diffrn_orient_matrix_UB_22      0.0106491000
_diffrn_orient_matrix_UB_23      -0.0046969000
_diffrn_orient_matrix_UB_31      -0.0032866000
_diffrn_orient_matrix_UB_32      0.0756739000
_diffrn_orient_matrix_UB_33      0.0093914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19704
_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         2.501
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.898
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0347P)^2^+1.4505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4628
_reflns_number_total             5078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-4DMAP_1-1dihydrate
_cod_database_code               7228136
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H24 Cl2 N4 O4'
_chemical_oxdiff_usercomment     L3-93-C
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O22(H22A,H22B), O21(H21B,H21C)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C21(H21A),
 C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              34775
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-93-C
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.556