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

data_7228131
_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 H9.5 Cl2 N2 O2, C15 H9 Cl2 N2 O2, C3 H5 N2, C3 H4.5 N2'
_chemical_formula_sum            'C36 H28 Cl4 N8 O4'
_chemical_formula_weight         778.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-09data_
_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                88.224(4)
_cell_angle_beta                 76.212(5)
_cell_angle_gamma                84.969(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0605(5)
_cell_length_b                   11.0252(6)
_cell_length_c                   16.3298(10)
_cell_measurement_reflns_used    8129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7870
_cell_measurement_theta_min      2.1310
_cell_volume                     1752.22(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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_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 0.999
_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    -27.00  73.00   1.00  100.00    --  -17.00  72.00  30.00  100
  2  \w    -69.00  22.00   1.00  100.00    --  -17.00 -72.00 -90.00   91
  3  \w    -68.00  22.00   1.00  100.00    --  -17.00 -72.00  90.00   90
  4  \w    -54.00  23.00   1.00  100.00    --  -17.00   0.00  60.00   77
  5  \w    -32.00 -16.00   1.00  100.00    --  -17.00  54.00-120.00   16
  6  \w    -31.00  73.00   1.00  100.00    --  -17.00  72.00 120.00  104
  7  \w    -69.00  15.00   1.00  100.00    --  -17.00 -72.00   0.00   84
;
_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      -0.0438142000
_diffrn_orient_matrix_UB_12      0.0532728000
_diffrn_orient_matrix_UB_13      -0.0026151000
_diffrn_orient_matrix_UB_21      0.0283301000
_diffrn_orient_matrix_UB_22      0.0291238000
_diffrn_orient_matrix_UB_23      0.0292600000
_diffrn_orient_matrix_UB_31      0.0508344000
_diffrn_orient_matrix_UB_32      0.0220286000
_diffrn_orient_matrix_UB_33      -0.0337273000
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21522
_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         2.180
_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    0.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 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    1.475
_exptl_crystal_description       chip
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         8029
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0789P)^2^+0.4823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5735
_reflns_number_total             8029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-IMID_1-1
_cod_original_cell_volume        1752.21(17)
_cod_database_code               7228131
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C33 H27 N6 O4 Cl4'
_cell_oxdiff_angle_alpha         88.224(4)
_cell_oxdiff_angle_beta          76.212(5)
_cell_oxdiff_angle_gamma         84.969(4)
_cell_oxdiff_length_a            10.0605(5)
_cell_oxdiff_length_b            11.0252(6)
_cell_oxdiff_length_c            16.3298(10)
_cell_oxdiff_measurement_reflns_used 8129
_cell_oxdiff_volume              1752.21(17)
_reflns_odcompleteness_completeness 99.90
_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
2. Rigid body (RIGU) restrains
 N45A, H45A, N46A, H46A, C45A, H45B, C46A, H46B, C47A, H47A, N45, H45, N46,
 H46, C45, H45C, C46, H46C, C47, H47
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(N45A)=Sof(H45A)=Sof(N46A)=Sof(H46A)=Sof(C45A)=Sof(H45B)=Sof(C46A)=
 Sof(H46B)=Sof(C47A)=Sof(H47A)=1-FVAR(1)
 Sof(N45)=Sof(H45)=Sof(N46)=Sof(H46)=Sof(C45)=Sof(H45C)=Sof(C46)=Sof(H46C)=
 Sof(C47)=Sof(H47)=FVAR(1)
 Fixed Sof: H1(0.5) H42(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C24(H24),
 C25(H25), C26(H26), C27(H27), C32(H32), C34(H34), C35(H35), N45A(H45A),
 N46A(H46A), C45A(H45B), C46A(H46B), C47A(H47A), N45(H45), C45(H45C), C46(H46C),
  C47(H47), N42(H42), C41(H41A), C42(H42A), C43(H43)
;
_shelx_res_checksum              25364
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-85-C2
_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 4.262
_oxdiff_exptl_absorpt_empirical_full_min 0.442