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

data_7228121
_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 H5 N2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C20 H18 Cl2 N4 O3'
_chemical_formula_weight         433.28
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.628(2)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   15.1394(5)
_cell_length_b                   29.9418(9)
_cell_length_c                   26.9456(6)
_cell_measurement_reflns_used    19472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8970
_cell_measurement_theta_min      2.7020
_cell_volume                     12106.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -13.00  91.00   0.50   60.00    --   15.17  57.00 -30.00  208
  2  \w    -62.00  38.00   0.50   60.00    --   15.17 -38.00-180.00  200
  3  \w    -28.00   7.00   0.50   60.00    --   15.17 -38.00-120.00   70
  4  \w     10.00  64.00   0.50   60.00    --   15.17  77.00 150.00  108
;
_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      0.0167002000
_diffrn_orient_matrix_UB_12      0.0206181000
_diffrn_orient_matrix_UB_13      -0.0077512000
_diffrn_orient_matrix_UB_21      -0.0307673000
_diffrn_orient_matrix_UB_22      -0.0008711000
_diffrn_orient_matrix_UB_23      -0.0222531000
_diffrn_orient_matrix_UB_31      -0.0318018000
_diffrn_orient_matrix_UB_32      0.0116157000
_diffrn_orient_matrix_UB_33      0.0122354000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            86240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.451
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             5376
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.145
_refine_diff_density_max         2.087
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1638
_refine_ls_number_reflns         27727
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0833P)^2^+11.8820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1737
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20228
_reflns_number_total             27727
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-IMID_1-1_solvate
_cod_database_code               7228121
_chemical_oxdiff_formula         'C120 H108 N24 O18 Cl12'
_chemical_oxdiff_usercomment     'L3-85-C1 recollect'
_reflns_odcompleteness_completeness 99.81
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11_5) = Uanis(C11A_5)
Uanis(C12_5) = Uanis(C12A_5)
Uanis(C14_5) = Uanis(C14A_5)
Uanis(C15_5) = Uanis(C15A_5)
Uanis(C15_4) = Uanis(C15A_4)
Uanis(C14_4) = Uanis(C14A_4)
Uanis(C12_4) = Uanis(C12A_4)
Uanis(C11_4) = Uanis(C11A_4)
Uanis(Cl1_5) = Uanis(Cl1A_5)
Uanis(O32A_15) = Uanis(O32_15)
3. Rigid body (RIGU) restrains
 C10_5, C11A_5, C12A_5, C13_5, C14A_5, C15A_5, C11_5, C12_5, C14_5, C15_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O31)=Sof(O32)=Sof(C33)=Sof(H33C)=Sof(H33D)=Sof(C31)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=Sof(C34)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C32)=1-FVAR(1)
 Sof(O31A)=Sof(O32A)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C31A)=Sof(H31A)=
 Sof(H31B)=Sof(H31C)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C32A)=FVAR(1)
 Sof(Cl1)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=1-
 FVAR(2)
 Sof(Cl1A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=FVAR(2)
 Sof(Cl1A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=1-FVAR(3)
 Sof(Cl1)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B), C9(H9A,H9B),
 C31(H31A,H31B), C33(H33A,H33B), C33A(H33A,H33B), C33(H33C,H33D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C4(H4), C5(H5),
 C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C4(H4), C5(H5), C6(H6), C7(H7),
 C12(H12), C14(H14), C15(H15), C4(H4), C5(H5), C6(H6), C7(H7), C12A(H12A),
 C14A(H14A), C15A(H15A), C12(H12), C14(H14), C15(H15), C4(H4), C5(H5), C6(H6),
 C7(H7), C12A(H12A), C14A(H14A), C15A(H15A), C12(H12), C14(H14), C15(H15),
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), N21(H21),
 N22(H22), C21(H21A), C22(H22A), C23(H23), N21(H21), N22(H22), C21(H21A),
 C22(H22A), C23(H23), N21(H21), N22(H22), C21(H21A), C22(H22A), C23(H23),
 N21(H21), N22(H22), C21(H21A), C22(H22A), C23(H23), N21(H21), N22(H22),
 C21(H21A), C22(H22A), C23(H23), N21(H21), N22(H22), C21(H21A), C22(H22A),
 C23(H23)
5.c Fitted hexagon refined as free rotating group:
 C10(C11A,C12A,C13,C14A,C15A), C10(C11A,C12A,C13,C14A,C15A)
5.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C31(H31A,H31B,H31C), C34(H34A,H34B,
 H34C), C31A(H31A,H31B,H31C), C34A(H34A,H34B,H34C), C31(H31D,H31E,H31F),
 C34(H34D,H34E,H34F)
;
_shelx_res_checksum              27138
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder using paratone oil'
_olex2_submission_original_sample_id L3-85-C1
_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 1.814
_oxdiff_exptl_absorpt_empirical_full_min 0.567