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_7229945
_publ_section_title
;
 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), C7 H12 O4'
_chemical_formula_sum            'C37 H58 N2 O12'
_chemical_formula_weight         722.85
_chemical_name_common            11-Aza:Pim
_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                   17.5836(7)
_cell_length_b                   10.3594(4)
_cell_length_c                   9.9524(3)
_cell_measurement_reflns_used    5938
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.1850
_cell_measurement_theta_min      4.4360
_cell_volume                     1812.88(11)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_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     78.00 112.00   1.00    8.00    --  110.57  77.00 -90.00   34
  2  \w     12.00 113.00   1.00    3.00    --   40.45  57.00  30.00  101
  3  \w    121.00 178.00   1.00    8.00    --  110.57  77.00 -90.00   57
  4  \w    152.00 177.00   1.00    8.00    --  110.57  37.00 -66.21   25
  5  \w    142.00 169.00   1.00    8.00    --  110.57  61.00 -60.00   27
  6  \w    121.00 177.00   1.00    8.00    --  110.57  77.00 -30.00   56
  7  \w     85.00 112.00   1.00    8.00    --  110.57  45.00 -30.00   27
  8  \w     84.00 109.00   1.00    8.00    --  110.57  45.00   0.00   25
  9  \w     81.00 106.00   1.00    8.00    --  110.57  61.00 -30.00   25
 10  \w     85.00 111.00   1.00    8.00    --  110.57  30.00 -30.00   26
 11  \w     85.00 124.00   1.00    8.00    --  110.57  30.00   0.00   39
 12  \w     84.00 145.00   1.00    8.00    --  110.57  45.00  30.00   61
 13  \w     78.00 103.00   1.00    8.00    --  110.57  77.00   0.00   25
 14  \w     80.00 106.00   1.00    8.00    --  110.57  61.00   0.00   26
 15  \w     80.00 105.00   1.00    8.00    --  110.57  68.00  17.69   25
 16  \w     77.00 104.00   1.00    8.00    --  110.57  77.00 -30.00   27
 17  \w     78.00 103.00   1.00    8.00    --  110.57  77.00 -60.00   25
 18  \w     81.00 106.00   1.00    8.00    --  110.57  61.00 -90.00   25
 19  \w     84.00 121.00   1.00    8.00    --  110.57  37.00 -66.21   37
 20  \w     80.00 106.00   1.00    8.00    --  110.57  61.00-120.00   26
 21  \w     83.00 109.00   1.00    8.00    --  110.57  45.00 -90.00   26
 22  \w     83.00 110.00   1.00    8.00    --  110.57  45.00 -60.00   27
 23  \w     80.00 106.00   1.00    8.00    --  110.57  61.00 -60.00   26
 24  \w     77.00 103.00   1.00    8.00    --  110.57  77.00-120.00   26
 25  \w     78.00 173.00   1.00    8.00    --  110.57  77.00-150.00   95
 26  \w     81.00 106.00   1.00    8.00    --  110.57  30.00  30.00   25
 27  \w     80.00 107.00   1.00    8.00    --  110.57  61.00  30.00   27
 28  \w     78.00 105.00   1.00    8.00    --  110.57  77.00  30.00   27
 29  \w     77.00 177.00   1.00    8.00    --  110.57  77.00  60.00  100
 30  \w     48.00 106.00   1.00    8.00    --  110.57 -94.00  90.00   58
 31  \w     26.00 104.00   1.00    8.00    --  110.57 -94.00   0.00   78
 32  \w     97.00 122.00   1.00    8.00    --  110.57-125.00 -90.00   25
 33  \w     56.00  98.00   1.00    3.00    --   40.45-125.00-180.00   42
 34  \w     36.00  80.00   1.00    8.00    --  110.57-125.00 -90.00   44
 35  \w     15.00 100.00   1.00    3.00    --   40.45  37.00 -30.00   85
 36  \w     27.00  54.00   1.00    3.00    --   40.45  57.00-150.00   27
 37  \w      8.00  36.00   1.00    3.00    --   40.45  77.00 -60.00   28
 38  \w      9.00  34.00   1.00    3.00    --   40.45  77.00 -30.00   25
 39  \w    -45.00 -20.00   1.00    3.00    --  -40.45 -57.00  60.00   25
 40  \w   -100.00 -62.00   1.00    3.00    --  -40.45 -57.00  60.00   38
 41  \w    -66.00  32.00   1.00    3.00    --  -40.45  37.00-150.00   98
 42  \w   -110.00 -61.00   1.00    3.00    --  -40.45-155.00 148.00   49
;
_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      -0.0850853000
_diffrn_orient_matrix_UB_12      -0.0157221000
_diffrn_orient_matrix_UB_13      -0.0334424000
_diffrn_orient_matrix_UB_21      0.0179023000
_diffrn_orient_matrix_UB_22      0.0130888000
_diffrn_orient_matrix_UB_23      -0.1508174000
_diffrn_orient_matrix_UB_31      0.0108382000
_diffrn_orient_matrix_UB_32      -0.1472813000
_diffrn_orient_matrix_UB_33      -0.0098907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16856
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.486
_diffrn_reflns_theta_min         4.443
_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    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74746
_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    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0340P)^2^+0.2270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0729
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3057
_reflns_number_total             3259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01875d2.cif
_cod_data_source_block           cpd8_madiha38cult
_cod_depositor_comments
'Adding full bibliography for 7229939--7229946.cif.'
_cod_original_cell_volume        1812.89(12)
_cod_database_code               7229945
_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, All O(H) groups
2. Restrained distances
 C22-C21 \\sim C23-C22 \\sim C24-C23 \\sim C24-C25 \\sim C25-C26 \\sim C26-C27
 with sigma of 0.02
 C21-C23 \\sim C25-C27
 with sigma of 0.02
 C22-C24 \\sim C23-C25
 with sigma of 0.02
 C23-C25 \\sim C24-C26
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O22, O23, C26, C27
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001
 O20, O21, C21, C22
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O20(0.5) O21(0.5) H21(0.5) O22(0.5) H22(0.5) O23(0.5) C21(0.5)
 C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5)
 H24B(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5) C27(0.5)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
5.d Idealised tetrahedral OH refined as rotating group:
 O21(H21), O22(H22)
;
_shelx_res_checksum              72915
_olex2_date_sample_data_collection 2017-07-11
_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 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.679