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_7229946
_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), C4 H6 O5'
_chemical_formula_sum            'C34 H52 N2 O13'
_chemical_formula_weight         696.77
_chemical_name_common            11-Aza:D-Mal
_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     iterative
_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                   10.43733(12)
_cell_length_b                   18.04445(19)
_cell_length_c                   18.6345(2)
_cell_measurement_reflns_used    12158
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      75.4300
_cell_measurement_theta_min      3.3990
_cell_volume                     3509.54(7)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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     39.00 141.00   1.00    8.00    --  110.57 -30.00  60.00  102
  2  \w    -71.00  36.00   1.00    4.00    --  -40.57  77.00 120.00  107
  3  \w    -70.00  33.00   1.00    4.00    --  -40.57  57.00  30.00  103
  4  \w    -70.00  32.00   1.00    4.00    --  -40.57  57.00 -90.00  102
  5  \w    130.00 178.00   1.00    8.00    --  110.57  30.00 120.00   48
  6  \w    122.00 178.00   1.00    8.00    --  110.57 111.00  90.00   56
  7  \w     80.00 118.00   1.00    8.00    --  110.57  30.00 120.00   38
  8  \w     53.00 141.00   1.00    8.00    --  110.57 -30.00 150.00   88
  9  \w     45.00 115.00   1.00    8.00    --  110.57-111.00  60.00   70
 10  \w     33.00 139.00   1.00    8.00    --  110.57 -30.00 -60.00  106
 11  \w     33.00 115.00   1.00    8.00    --  110.57-111.00 -90.00   82
 12  \w     32.00 130.00   1.00    8.00    --  110.57 -77.00  90.00   98
;
_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      -0.0679821000
_diffrn_orient_matrix_UB_12      0.0525212000
_diffrn_orient_matrix_UB_13      -0.0529089000
_diffrn_orient_matrix_UB_21      -0.1049696000
_diffrn_orient_matrix_UB_22      0.0150924000
_diffrn_orient_matrix_UB_23      0.0563410000
_diffrn_orient_matrix_UB_31      0.0782247000
_diffrn_orient_matrix_UB_32      0.0657088000
_diffrn_orient_matrix_UB_33      0.0292547000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19371
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         3.409
_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    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90752
_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    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_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     487
_refine_ls_number_reflns         6284
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0420P)^2^+0.4980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6062
_reflns_number_total             6284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01875d2.cif
_cod_data_source_block           cpd7_madiha30cult
_cod_depositor_comments
'Adding full bibliography for 7229939--7229946.cif.'
_cod_original_cell_volume        3509.55(7)
_cod_database_code               7229946
_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
 O22A-C23
 1.38 with sigma of 0.02
 O22A-C23A
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.003
4. Rigid body (RIGU) restrains
 O22A, C22, C23A, C24
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O22(0.9) H22(0.9) O22A(0.1) H22A(0.1) H22C(0.1) C23(0.9) H23A(0.9)
 H23B(0.9) C23A(0.1) H23C(0.1)
6.a Riding coordinates:
 C22(H22C,H22B), C23(H23A,H23B)
6.b Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C2A(H2A), C6A(H6A), C9A(H9A),
 C11A(H11C), C12A(H12A), C23A(H23C)
6.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB)
6.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13A(H13D,H13E,
 H13F), C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F)
6.e Idealised tetrahedral OH refined as rotating group:
 O22A(H22A)
;
_shelx_res_checksum              53549
_olex2_date_sample_data_collection 2017-06-19
_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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.866