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_7229943
_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         'C15 H23 N O4, C8 H8 O3'
_chemical_formula_sum            'C23 H31 N O7'
_chemical_formula_weight         433.49
_chemical_name_common            11-Aza:D-Man
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   10.00907(10)
_cell_length_b                   10.09992(10)
_cell_length_c                   20.9254(2)
_cell_measurement_reflns_used    9723
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.5490
_cell_measurement_theta_min      4.2190
_cell_volume                     2115.37(4)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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     40.00 130.00   1.00    3.00    --  110.57 -45.00-150.00   90
  2  \w     21.00  48.00   1.00    1.00    --   40.57 -99.00   0.00   27
  3  \w     88.00 178.00   1.00    3.00    --  110.57  45.00  30.00   90
  4  \w     93.00 178.00   1.00    3.00    --  110.57  45.00 150.00   85
  5  \w     97.00 178.00   1.00    3.00    --  110.57 125.00 -30.00   81
  6  \w    -94.00  -5.00   1.00    1.00    --  -40.57 125.00-120.00   89
  7  \w   -104.00 -17.00   1.00    1.00    --  -40.57 -37.00  30.00   87
  8  \w    -67.00  36.00   1.00    1.00    --  -40.57  37.00-150.00  103
  9  \w     96.00 178.00   1.00    3.00    --  110.57  82.00 -96.00   82
 10  \w     57.00 144.00   1.00    3.00    --  110.57 -77.00 -60.00   87
 11  \w     32.00  84.00   1.00    3.00    --  110.57-111.00-150.00   52
 12  \w    104.00 147.00   1.00    3.00    --  110.57 111.00-150.00   43
 13  \w     47.00 115.00   1.00    3.00    --  110.57-111.00 -90.00   68
 14  \w     33.00 112.00   1.00    3.00    --  110.57-111.00 120.00   79
;
_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      -0.0917488000
_diffrn_orient_matrix_UB_12      -0.0045249000
_diffrn_orient_matrix_UB_13      0.0590989000
_diffrn_orient_matrix_UB_21      0.0749120000
_diffrn_orient_matrix_UB_22      -0.1233285000
_diffrn_orient_matrix_UB_23      0.0243883000
_diffrn_orient_matrix_UB_31      0.0983599000
_diffrn_orient_matrix_UB_32      0.0895369000
_diffrn_orient_matrix_UB_33      0.0365218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12213
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         4.226
_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    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71696
_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_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1564 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0227
_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^)+(0.0360P)^2^+0.2670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0576
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3677
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01875d2.cif
_cod_data_source_block           cpd4_madiha27cult
_cod_depositor_comments
'Adding full bibliography for 7229939--7229946.cif.'
_cod_database_code               7229943
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C22(H22A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              1233
_olex2_date_sample_data_collection 2017-05-16
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.712