11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons
Nisar, Madiha; Sung, Herman H.-Y.; Puschmann, Horst; Lakerveld, Richard; Haynes, Richard K.; Williams, Ian D.; CrystEngComm 20 (2018) 1205–; doi:10.1039/C7CE01875D

data_7229942
_publ_section_title
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 11-Azaartemisinin cocrystals with preserved lactam&#x2009;:&#x2009;acid
 heterosynthons
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1205
_journal_paper_doi               10.1039/C7CE01875D
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C15 H23 N O4), C4 H6 O4'
_chemical_formula_sum            'C34 H52 N2 O12'
_chemical_formula_weight         680.77
_chemical_name_common            11-Aza:Succ
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.9674(7)
_cell_length_b                   10.3025(4)
_cell_length_c                   9.3723(7)
_cell_measurement_reflns_used    2959
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4780
_cell_measurement_theta_min      4.7070
_cell_volume                     1734.90(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    146.00 172.00   1.00    8.00    --  110.57  15.00  60.00   26
  2  \w      5.00  58.00   1.00    3.00    --   40.45 -99.00  60.00   53
  3  \w    -76.00  29.00   1.00    3.00    --  -40.45  85.00 -55.00  105
  4  \w   -119.00 -10.00   1.00    3.00    --  -40.45 -77.00 120.00  109
  5  \w   -115.00 -24.00   1.00    3.00    --  -40.45 -77.00-150.00   91
  6  \w     81.00 161.00   1.00    8.00    --  110.57  30.00  90.00   80
  7  \w     62.00 144.00   1.00    8.00    --  110.57 -77.00 -60.00   82
  8  \w     58.00 129.00   1.00    8.00    --  110.57  15.00  60.00   71
  9  \w     45.00 115.00   1.00    8.00    --  110.57-111.00-120.00   70
 10  \w     36.00 139.00   1.00    8.00    --  110.57 -30.00-120.00  103
 11  \w     36.00 109.00   1.00    8.00    --  110.57 -61.00-150.00   73
 12  \w     33.00 129.00   1.00    8.00    --  110.57 -30.00  90.00   96
 13  \w     28.00 108.00   1.00    8.00    --  110.57 -94.00 120.00   80
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0416687000
_diffrn_orient_matrix_UB_12      -0.0565001000
_diffrn_orient_matrix_UB_13      0.1293201000
_diffrn_orient_matrix_UB_21      -0.0218932000
_diffrn_orient_matrix_UB_22      -0.1198652000
_diffrn_orient_matrix_UB_23      -0.0890678000
_diffrn_orient_matrix_UB_31      0.0716154000
_diffrn_orient_matrix_UB_32      -0.0695680000
_diffrn_orient_matrix_UB_33      0.0483789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9822
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.472
_diffrn_reflns_theta_min         4.718
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0583P)^2^+0.5968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2825
_reflns_number_total             3114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01875d2.cif
_cod_data_source_block           cpd5_madiha28a
_cod_depositor_comments
'Adding full bibliography for 7229939--7229946.cif.'
_cod_original_cell_volume        1734.91(16)
_cod_database_code               7229942
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              61518
_olex2_date_sample_data_collection 2017-06-27
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.859