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

data_7228133
_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 H10 Cl2 N2 O2, C6 H6 N2 O'
_chemical_formula_sum            'C21 H16 Cl2 N4 O3'
_chemical_formula_weight         443.28
_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
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.25 svn.r3318 for OlexSys, GUI svn.r5204)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.409(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9910(3)
_cell_length_b                   7.6724(2)
_cell_length_c                   19.8344(5)
_cell_measurement_reflns_used    12070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9310
_cell_measurement_theta_min      3.1560
_cell_volume                     1960.43(8)
_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    'ShelXT (Sheldrick, 2015)'
_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   35.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003  178.0000 -120.0000 67

  2 omega  -87.00   14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  -57.0000 -120.0000 101

  3 omega  -90.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  -77.0000  120.0000 109

  4 omega  -42.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597   57.0000   30.0000 101

  5 omega  -20.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003  -99.0000 -120.0000 52

  6 omega   34.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003 -178.0000   30.0000 66

  7 omega   34.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1003 -178.0000    0.0000 66

  8 omega -101.00  -55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  178.0000  -30.0000 46

  9 omega  -88.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9597  -38.0000  -30.0000 99
;
_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      0.0022889000
_diffrn_orient_matrix_UB_12      -0.0780454000
_diffrn_orient_matrix_UB_13      -0.0189110000
_diffrn_orient_matrix_UB_21      0.0548618000
_diffrn_orient_matrix_UB_22      -0.0005764000
_diffrn_orient_matrix_UB_23      0.0077565000
_diffrn_orient_matrix_UB_31      -0.0042855000
_diffrn_orient_matrix_UB_32      -0.0495023000
_diffrn_orient_matrix_UB_33      0.0297053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.090
_diffrn_source                   'micro-focus sealed tube X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.941
_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    1.502
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.4588
_exptl_crystal_size_mid          0.3589
_exptl_crystal_size_min          0.1876
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0370P)^2^+1.7336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3998
_reflns_number_total             4486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-ISO
_cod_original_cell_volume        1960.43(9)
_cod_database_code               7228133
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C23(H23),
 C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              32683
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'MiTeGen Micromesh'
_olex2_submission_original_sample_id L2-89-A
_olex2_submission_special_instructions 'No special instructions were received'