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_7229939
_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         'C15 H23 N O4'
_chemical_formula_sum            'C15 H23 N O4'
_chemical_formula_weight         281.34
_chemical_name_common            11-Azaart
_chemical_name_systematic        11-azaartemisinin
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_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                120
_cell_formula_units_Z            3
_cell_length_a                   11.71759(15)
_cell_length_b                   11.71759(15)
_cell_length_c                   9.48728(13)
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9010
_cell_measurement_theta_min      6.3710
_cell_volume                     1128.10(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 26

  2 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 26

  3 omega   26.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   60.0000 51

  4 omega  123.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -60.0000 47

  5 omega  127.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -120.0000 50

  6 omega  119.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -150.0000 55

  7 omega   82.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000 -150.0000 25

  8 omega   83.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000 -120.0000 35

  9 omega   85.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -90.0000 26

 10 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -150.0000 26

 11 omega   80.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000 -120.0000 26

 12 omega   80.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000  -90.0000 46

 13 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -120.0000 26

 14 omega  102.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000   30.0000 75

 15 omega   33.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 54

 16 omega   64.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000 -150.0000 30

 17 omega   23.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000 -150.0000 31

 18 omega  -43.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 31

 19 omega  -75.00  -48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 27

 20 omega -111.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453    0.0000 -180.0000 144

 21 omega -108.00  -83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453 -133.0000  124.0000 25

 22 omega -122.00  -89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -89.0000  157.0000 33
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1415895000
_diffrn_orient_matrix_UB_12      -0.1119422000
_diffrn_orient_matrix_UB_13      -0.0292878000
_diffrn_orient_matrix_UB_21      0.0549017000
_diffrn_orient_matrix_UB_22      -0.0798797000
_diffrn_orient_matrix_UB_23      -0.0732449000
_diffrn_orient_matrix_UB_31      -0.0004273000
_diffrn_orient_matrix_UB_32      -0.0640041000
_diffrn_orient_matrix_UB_33      0.1418938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5621
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.285
_diffrn_reflns_theta_min         4.357
_diffrn_source                   '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    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_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^)+(0.0299P)^2^+0.1784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0582
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2604
_reflns_number_total             2647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01875d2.cif
_cod_data_source_block           madiha1cult_cpd1
_cod_depositor_comments
'Adding full bibliography for 7229939--7229946.cif.'
_cod_database_code               7229939
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.898
_reflns_odcompleteness_completeness 99.93
_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
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)
2.c Aromatic/amide H refined with riding coordinates:
 N11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              21809
_olex2_date_sample_data_collection 2016-03-17
_olex2_submission_special_instructions 'No special instructions were received'