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

data_7228128
_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 H10 Cl2 N2 O2), C10 H8 N2'
_chemical_formula_sum            'C40 H28 Cl4 N6 O4'
_chemical_formula_weight         798.48
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-02-09 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.879(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.6725(11)
_cell_length_b                   26.2388(13)
_cell_length_c                   8.6827(3)
_cell_measurement_reflns_used    10551
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.4860
_cell_measurement_theta_min      2.4080
_cell_volume                     7426.5(5)
_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    -44.00  73.00   1.00   55.00    --  -17.00  18.00-180.00  117
  2  \w    -62.00  19.00   1.00   55.00    --  -17.00 -54.00   0.00   81
  3  \w    -36.00  -5.00   1.00   55.00    --  -17.00 -72.00 120.00   31
  4  \w   -107.00 -50.00   1.00   55.00    --  -17.00 -18.00   0.00   57
;
_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      0.0150127000
_diffrn_orient_matrix_UB_12      -0.0007301000
_diffrn_orient_matrix_UB_13      0.0628750000
_diffrn_orient_matrix_UB_21      -0.0016794000
_diffrn_orient_matrix_UB_22      0.0267872000
_diffrn_orient_matrix_UB_23      0.0086421000
_diffrn_orient_matrix_UB_31      -0.0156667000
_diffrn_orient_matrix_UB_32      -0.0035652000
_diffrn_orient_matrix_UB_33      0.0517003000
_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_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            50025
_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         27.483
_diffrn_reflns_theta_min         1.552
_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    0.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93006
_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    1.428
_exptl_crystal_description       plate
_exptl_crystal_F_000             3280
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1073
_refine_ls_number_reflns         17020
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0758
_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^)+(0.0815P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8935
_reflns_number_total             17020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00651a2.cif
_cod_data_source_block           LON-44BIPY
_cod_original_cell_volume        7426.6(5)
_cod_database_code               7228128
_chemical_oxdiff_formula         'C80 H61 Cl8 N12 O8'
_reflns_odcompleteness_completeness 99.87
_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 O(H) groups
2. Restrained distances
 H27-H29D = H27-H29C
 -2.1 with sigma of 0.02
 O41-H41
 0.98 with sigma of 0.02
 C70-C69 \\sim C70A-C69A
 with sigma of 0.02
 N61-C69 \\sim N61-C69A
 with sigma of 0.02
 N41-C49 \\sim N41-C49A
 with sigma of 0.02
 C50-C49 \\sim C50A-C49A
 with sigma of 0.02
 N1-C9A \\sim N1-C9
 with sigma of 0.02
 Cl1-C11 \\sim Cl1A-C11A
 with sigma of 0.02
 C10-C9 \\sim C9A-C10A
 with sigma of 0.02
 C9A-N1 \\sim C9A-C10A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C69 \\sim C69A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C49A \\sim C49: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C9 \\sim C9A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C29 \\sim C29A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uiso(C52A) = Uiso(C53A) = Uiso(C54A) = Uiso(C55A) = Uiso(C50A) = Uiso(C51A) =
Uiso(C49A)
Uanis(Cl42) = Uanis(Cl)
Uanis(Cl41) = Uanis(Cl5)
Uanis(Cl61) = Uanis(Cl6)
Uiso(C70A) = Uiso(C71A) = Uiso(C72A) = Uiso(C73A) = Uiso(C74A) = Uiso(C75A)
Uiso(C10A) = Uiso(C11A) = Uiso(C15A) = Uiso(C14A) = Uiso(C13A) = Uiso(C12A)
Uiso(C30A) = Uiso(C35A) = Uiso(C34A) = Uiso(C33A) = Uiso(C31A) = Uiso(C32A)
Uanis(Cl21) = Uanis(Cl3)
Uanis(Cl22) = Uanis(Cl4)
Uiso(C29A) = Uiso(C30A)
4. Rigid body (RIGU) restrains
 C69, C69A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C49A, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29A, C29
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C9, C10, C15, C14, C13, C12, C11, Cl1, Cl2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C9A, C10A, C15A, C14A, C13A, C12A, C11A, Cl1A, Cl2A}
{C29, C30, C31, C32, C33, C34, C35, Cl21, Cl22} sigma for 1-2: 0.02, 1-3: 0.04
as
{C29A, C30A, C31A, C32A, C33A, C34A, C35A, Cl3, Cl4}
{C49, C50, C51, C52, C53, C54, C55, Cl41, Cl42} sigma for 1-2: 0.02, 1-3: 0.04
as
{C49A, C50A, C51A, C52A, C53A, C54A, C55A, Cl, Cl5}
6. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=
 Sof(H14A)=Sof(C13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=
 Sof(C13)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
 Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(C31A)=Sof(C32A)=Sof(H32A)=
 Sof(C33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=Sof(Cl3)=Sof(Cl4)=1-FVAR(2)
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=
 Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(Cl21)=Sof(Cl22)=FVAR(2)
 Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C50A)=Sof(C51A)=Sof(C52A)=Sof(H52A)=
 Sof(C53A)=Sof(C54A)=Sof(H54A)=Sof(C55A)=Sof(H55A)=Sof(Cl)=Sof(Cl5)=1-FVAR(3)
 Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(C51)=Sof(C52)=Sof(H52)=Sof(C53)=
 Sof(C54)=Sof(H54)=Sof(C55)=Sof(H55)=Sof(Cl41)=Sof(Cl42)=FVAR(3)
 Sof(C70A)=Sof(C71A)=Sof(C72A)=Sof(H72A)=Sof(C73A)=Sof(C74A)=Sof(H74A)=
 Sof(C75A)=Sof(H75A)=Sof(C69A)=Sof(H69C)=Sof(H69D)=Sof(Cl6)=Sof(Cl7)=1-FVAR(4)
 Sof(Cl61)=Sof(Cl62)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(C70)=Sof(C71)=Sof(C72)=
 Sof(H72)=Sof(C73)=Sof(C74)=Sof(H74)=Sof(C75)=Sof(H75)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C49(H49A,H49B), C29(H29A,H29B), C69(H69A,H69B),
 C29A(H29C,H29D), C49A(H49C,H49D), C69A(H69C,H69D)
7.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C4(H4), C5(H5), C6(H6), C7(H7), C15A(H15A),
 C14A(H14A), C12A(H12A), C52(H52), C54(H54), C55(H55), C44(H44), C45(H45),
 C46(H46), C47(H47), C32(H32), C34(H34), C35(H35), C24(H24), C25(H25), C26(H26),
  C27(H27), C64(H64), C65(H65), C66(H66), C67(H67), C72(H72), C74(H74),
 C75(H75), C91(H91), C92(H92), C94(H94), C95(H95), C97(H97), C98(H98), C99(H99),
  C100(H100), C81(H81), C82(H82), C84(H84), C85(H85), C87(H87), C88(H88),
 C89(H89), C90(H90), C32A(H32A), C34A(H34A), C35A(H35A), C52A(H52A), C54A(H54A),
  C55A(H55A), C72A(H72A), C74A(H74A), C75A(H75A)
7.c Fitted hexagon refined as free rotating group:
 C10A(C15A,C14A,C13A,C12A,C11A), C30A(C31A,C32A,C33A,C34A,C35A), C50A(C51A,
 C52A,C53A,C54A,C55A), C70A(C71A,C72A,C73A,C74A,C75A)
;
_shelx_res_checksum              88734
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted in oil on a MITIGEN holder'
_olex2_submission_original_sample_id 'L3-78-A rpt'
_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 1.494
_oxdiff_exptl_absorpt_empirical_full_min 0.550