The effects of cis and trans butenedioic acid on the physicochemical behavior of lumefantrine
Tomar, Devendrasingh; Lodagekar, Anurag; Gunnam, Anilkumar; Allu, Suryanarayana; Chavan, Rahul B.; Tharkar, Minakshi; Ajithkumar, T. G.; Nangia, Ashwini K.; Shastri, Nalini R.; CrystEngComm 24 (2022) 156–168; doi:10.1039/D0CE01709D

data_7243889
_publ_section_title
;
 The effects of cis and trans butenedioic acid on the physicochemical
 behavior of lumefantrine
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              156
_journal_page_last               168
_journal_paper_doi               10.1039/D0CE01709D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C30 H33 Cl3 N O, C2 H O2'
_chemical_formula_sum            'C32 H34 Cl3 N O3'
_chemical_formula_weight         586.95
_chemical_name_common            'Lumifantrine-Fumaric Acid 2:1 salt'
_chemical_name_systematic
'2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol - (2E)-but-2-enedioic acid'
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-09-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-04 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.164(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4556(3)
_cell_length_b                   26.8887(7)
_cell_length_c                   9.5696(3)
_cell_measurement_reflns_used    15902
_cell_measurement_temperature    103(5)
_cell_measurement_theta_max      26.9140
_cell_measurement_theta_min      2.2490
_cell_volume                     2947.08(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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     -9.00  17.00   0.50    9.00    --   16.22 -30.00  30.00   52
  2  \w     -7.00  85.00   0.50    9.00    --   16.22  61.00  30.00  184
  3  \w     -7.00  83.00   0.50    9.00    --   16.22  45.00 120.00  180
  4  \w     40.00  89.00   0.50    9.00    --   16.22  77.00 150.00   98
  5  \w     -9.00  32.00   0.50    9.00    --   16.22  77.00 150.00   82
  6  \w    -32.00  -6.00   0.50    9.00    --  -14.97 109.00 -16.00   52
  7  \w    -15.00  10.00   0.50    9.00    --  -14.97 -61.00 -60.00   50
  8  \w    -34.00  11.00   0.50    9.00    --  -14.97 -94.00 -60.00   90
  9  \w      9.00  41.00   0.50    9.00    --   16.22-109.00-112.00   64
 10  \w    -44.00  10.00   0.50    9.00    --  -14.97 -45.00-180.00  108
 11  \w     51.00  89.00   0.50    9.00    --   16.22  30.00-150.00   76
 12  \w     -8.00  43.00   0.50    9.00    --   16.22  30.00-150.00  102
 13  \w    -63.00 -11.00   0.50    9.00    --  -14.97 125.00-180.00  104
 14  \w    -60.00 -19.00   0.50    9.00    --  -14.97 125.00 -90.00   82
 15  \w    -78.00 -51.00   0.50    9.00    --  -14.97 -61.00 -60.00   54
 16  \w    -73.00 -48.00   0.50    9.00    --  -14.97 -45.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            27047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.259
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.323
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0505P)^2^+2.9567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4785
_reflns_number_total             6001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01709d2.cif
_cod_data_source_block           lmf-fa
_cod_depositor_comments          'Adding full bibliography for 7243889.cif.'
_cod_database_code               7243889
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.934
_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, All O(H) groups
2. Restrained distances
 O4-C34 \\sim O2-C31
 with sigma of 0.02
 O5-C34 \\sim O3-C31
 with sigma of 0.02
 C34-C33 \\sim C31-C32
 with sigma of 0.02
 O5-C33 \\sim O3-C32
 with sigma of 0.04
 O4-O5 \\sim O2-O3
 with sigma of 0.04
 O4-C33 \\sim O2-C32
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C30B) = Uanis(C21)
Uanis(C21B) = Uanis(C21A)
4. Others
 Sof(C29B)=Sof(H29C)=Sof(H29D)=Sof(C30B)=Sof(H30A)=Sof(H30B)=Sof(H30C)=
 Sof(O1B)=Sof(H1B)=Sof(C21B)=1-FVAR(1)
 Sof(C21A)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(C21)=Sof(H21B)=Sof(H21C)=
 Sof(H21D)=Sof(O1A)=Sof(H1A)=FVAR(1)
 Sof(O2)=Sof(O3)=Sof(C31)=Sof(C32)=Sof(H32)=1-FVAR(2)
 Sof(O4)=Sof(O5)=Sof(C34)=Sof(C33)=Sof(H33)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 N1(H1), C21A(H21A)
5.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,
 H28B), C29A(H29A,H29B), C29B(H29C,H29D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C16(H16),
 C17(H17), C19(H19), C33(H33), C32(H32)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C21(H21B,H21C,H21D), C30B(H30A,H30B,H30C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_shelx_res_checksum              11486
_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
;