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

data_7228124
_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 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.673(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   20.6918(6)
_cell_length_b                   4.61421(12)
_cell_length_c                   20.1099(5)
_cell_measurement_reflns_used    17782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7920
_cell_measurement_theta_min      2.1360
_cell_volume                     1919.89(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_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_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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    -17.00  73.00   0.50   50.00    --  -17.00  72.00-120.00  180
  2  \w    -68.00  22.00   0.50   50.00    --  -17.00 -72.00 120.00  180
  3  \w    -64.00  22.00   0.50   50.00    --  -17.00 -72.00 -60.00  172
  4  \w    -86.00 -13.00   0.50   50.00    --  -17.00   0.00 -60.00  146
  5  \w    -92.00 -77.00   0.50   50.00    --  -17.00 -18.00  30.00   30
  6  \w    -27.00  73.00   0.50   50.00    --  -17.00  72.00 -60.00  200
  7  \w    -68.50  22.00   0.50   50.00    --  -17.00 -72.00-180.00  181
  8  \w    -68.00  22.00   0.50   50.00    --  -17.00 -72.00   0.00  180
  9  \w    -85.50  -7.00   0.50   50.00    --  -17.00   0.00   0.00  157
 10  \w    -60.00  73.00   0.50   50.00    --  -17.00   0.00 120.00  266
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC10 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228822000
_diffrn_orient_matrix_UB_12      0.0540999000
_diffrn_orient_matrix_UB_13      -0.0228762000
_diffrn_orient_matrix_UB_21      -0.0255515000
_diffrn_orient_matrix_UB_22      0.0487619000
_diffrn_orient_matrix_UB_23      -0.0209853000
_diffrn_orient_matrix_UB_31      0.0001272000
_diffrn_orient_matrix_UB_32      0.1354143000
_diffrn_orient_matrix_UB_33      0.0166923000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.584
_diffrn_reflns_theta_min         1.969
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0703P)^2^+4.7433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4061
_reflns_number_total             4368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-NICO
_cod_database_code               7228124
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C21 H16 N4 O3 Cl2'
_cell_oxdiff_angle_alpha         89.993(2)
_cell_oxdiff_angle_beta          90.704(2)
_cell_oxdiff_angle_gamma         90.099(2)
_cell_oxdiff_length_a            20.6811(5)
_cell_oxdiff_length_b            4.61310(11)
_cell_oxdiff_length_c            20.1253(5)
_cell_oxdiff_measurement_reflns_used 17782
_cell_oxdiff_volume              1919.89(8)
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9651(7)
 0.0349(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.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              3395
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.373
_oxdiff_exptl_absorpt_empirical_full_min 0.281