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

data_7228122
_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         '2(C15 H9 Cl2 N2 O2), 2(C2 H6 N)'
_chemical_formula_sum            'C34 H30 Cl4 N6 O4'
_chemical_formula_weight         728.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-09-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                68.926(6)
_cell_angle_beta                 85.447(4)
_cell_angle_gamma                88.975(4)
_cell_formula_units_Z            2
_cell_length_a                   11.6186(5)
_cell_length_b                   12.3390(8)
_cell_length_c                   12.5559(7)
_cell_measurement_reflns_used    10444
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.1520
_cell_measurement_theta_min      3.3160
_cell_volume                     1674.24(17)
_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 0.989
_diffrn_measurement_details
;
  1 omega  -25.00   57.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  -95.0000  -58.0000 164

  2 omega  -57.00    3.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.7923   95.0000   52.0000 120

  3 omega  -24.00   25.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.7923  -95.0000  -58.0000 98

  4 omega   35.00  106.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  178.0000 -120.0000 142

  5 omega  -62.00   44.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  -38.0000  -90.0000 212

  6 omega  -62.00   44.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  -38.0000 -180.0000 212

  7 omega   35.00  106.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.1673  178.0000 -180.0000 142

  8 omega   -7.00   18.00   0.5000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.7923  -99.0000  150.0000 50
;
_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      -0.0216434000
_diffrn_orient_matrix_UB_12      -0.0573262000
_diffrn_orient_matrix_UB_13      0.0291479000
_diffrn_orient_matrix_UB_21      0.0178819000
_diffrn_orient_matrix_UB_22      0.0015628000
_diffrn_orient_matrix_UB_23      0.0521500000
_diffrn_orient_matrix_UB_31      -0.0544321000
_diffrn_orient_matrix_UB_32      0.0225138000
_diffrn_orient_matrix_UB_33      0.0108848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.480
_diffrn_source                   'micro-focus sealed tube X-ray'
_diffrn_source_current           0.8
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.916
_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    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.784
_exptl_crystal_size_mid          0.1089
_exptl_crystal_size_min          0.0687
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         13510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0511
_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^)+(0.1037P)^2^+0.3698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10825
_reflns_number_total             13510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-PIPE
_cod_database_code               7228122
_chemical_oxdiff_formula         'c34 h30 c14 n6 o4'
_chemical_oxdiff_usercomment     L3-31-C2
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4751(10) 0.5249(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B), C61(H61C,H61D), C62(H62A,H62B), C51(H51C,H51D),
 C52(H52A,H52B)
3.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)
;
_shelx_res_checksum              27653
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-09-28
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_original_sample_id L3-31-C2
_olex2_submission_special_instructions 'No special instructions were received'