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

data_7228135
_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, C15 H9 Cl2 N2 O2, C7 H11 N2'
_chemical_formula_sum            'C37 H30 Cl4 N6 O4'
_chemical_formula_weight         764.47
_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             2017-02-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                79.963(3)
_cell_angle_beta                 81.329(2)
_cell_angle_gamma                84.947(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5711(2)
_cell_length_b                   12.3681(4)
_cell_length_c                   16.6270(5)
_cell_measurement_reflns_used    8486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5060
_cell_measurement_theta_min      2.8360
_cell_volume                     1712.32(9)
_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      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
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -20.00  97.00   0.50   40.00    --   15.17  77.00 120.00  234
  2  \w    -20.00  97.00   0.50   40.00    --   15.17  77.00-150.00  234
  3  \w    -20.00  97.00   0.50   40.00    --   15.17  77.00   0.00  234
  4  \w    -51.00  66.00   0.50   40.00    --  -15.79  77.00-120.00  234
  5  \w    -61.00  43.00   0.50   40.00    --   15.17 -57.00  90.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  SuperNova
_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      0.0159428000
_diffrn_orient_matrix_UB_12      -0.0556658000
_diffrn_orient_matrix_UB_13      -0.0055725000
_diffrn_orient_matrix_UB_21      0.0244085000
_diffrn_orient_matrix_UB_22      0.0174154000
_diffrn_orient_matrix_UB_23      -0.0426548000
_diffrn_orient_matrix_UB_31      0.0786512000
_diffrn_orient_matrix_UB_32      0.0019275000
_diffrn_orient_matrix_UB_33      0.0079266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24011
_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         27.559
_diffrn_reflns_theta_min         2.512
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80169
_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    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.059
_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     567
_refine_ls_number_reflns         7913
_refine_ls_number_restraints     1010
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.3674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6467
_reflns_number_total             7913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-4DMAP_2-1
_cod_original_cell_volume        1712.33(9)
_cod_database_code               7228135
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H20 O4 N4 Cl2'
_chemical_oxdiff_usercomment     L3-21-C2
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl24)=Sof(H32)=1-FVAR(1)
 Sof(Cl23)=Sof(H36)=FVAR(1)
 Fixed Sof: N41(0.5) H41(0.5) N42(0.5) C41(0.5) H41A(0.5) C42(0.5) H42(0.5)
 C43(0.5) C44(0.5) H44(0.5) C45(0.5) H45(0.5) C46(0.5) H46A(0.5) H46B(0.5)
 H46C(0.5) C47(0.5) H47A(0.5) H47B(0.5) H47C(0.5) N41A(0.5) H41B(0.5) N42A(0.5)
 C41A(0.5) H41C(0.5) C42A(0.5) H42A(0.5) C43A(0.5) C44A(0.5) H44A(0.5)
 C45A(0.5) H45A(0.5) C46A(0.5) H46D(0.5) H46E(0.5) H46F(0.5) C47A(0.5)
 H47D(0.5) H47E(0.5) H47F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B)
6.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), C33(H33), C35(H35), C36(H36),
 C41(H41A), C42(H42), C44(H44), C45(H45), C41A(H41C), C42A(H42A), C44A(H44A),
 C45A(H45A)
6.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C46A(H46D,H46E,H46F), C47A(H47D,
 H47E,H47F)
;
_shelx_res_checksum              608
_olex2_submission_original_sample_id L3-21-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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.797
_oxdiff_exptl_absorpt_empirical_full_min 0.753