Insight into amoxicillin sodium heterosolvates and non-solvated form: crystal structures, phase transformation behaviors, and desolvation mechanism
Cui, Pingping; Yin, Qiuxiang; Zhang, Shihao; Yang, Wenchao; Jia, Lihong; Dai, Jiayu; Zhou, Ling; Wang, Zhao; CrystEngComm 23 (2021) 3995–4004; doi:10.1039/D1CE00435B

data_7242817
_publ_section_title
;
 Insight into amoxicillin sodium heterosolvates and non-solvated form:
 crystal structures, phase transformation behaviors, and desolvation
 mechanism
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3995
_journal_page_last               4004
_journal_paper_doi               10.1039/D1CE00435B
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 N3 Na O5 S'
_chemical_formula_sum            'C16 H18 N3 Na O5 S'
_chemical_formula_weight         387.38
_chemical_name_common            'amoxicillin sodium'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-02-03 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6221(10)
_cell_length_b                   13.075(3)
_cell_length_c                   13.3414(14)
_cell_measurement_reflns_used    507
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      46.5060
_cell_measurement_theta_min      6.3150
_cell_volume                     1852.9(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.686
_diffrn_measured_fraction_theta_max 0.685
_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     85.00 138.00   0.50    4.00    --   66.14 129.00  19.00  106
  2  \w     -6.00  86.00   0.50    4.00    --   66.14 -29.00  -1.00  184
  3  \w    -79.00 -53.00   0.50    0.50    --   -1.09-179.00-120.00   52
  4  \w    -84.00 -50.00   0.50    0.50    --   -1.09-179.00-150.00   68
  5  \w    -86.00 -48.00   0.50    0.50    --   -1.09-179.00 -90.00   76
  6  \w    -74.00 -42.00   0.50    4.00    --  -68.33 125.00 -30.00   64
  7  \w   -113.00 -88.00   0.50    4.00    --  -68.33 125.00 -30.00   50
  8  \w   -139.00-114.00   0.50    4.00    --  -68.33 -99.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0100761000
_diffrn_orient_matrix_UB_12      0.1124693000
_diffrn_orient_matrix_UB_13      -0.0333554000
_diffrn_orient_matrix_UB_21      0.0524874000
_diffrn_orient_matrix_UB_22      -0.0344758000
_diffrn_orient_matrix_UB_23      -0.1020409000
_diffrn_orient_matrix_UB_31      -0.1348808000
_diffrn_orient_matrix_UB_32      -0.0051132000
_diffrn_orient_matrix_UB_33      -0.0426402000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.686
_diffrn_reflns_Laue_measured_fraction_max 0.685
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2273
_diffrn_reflns_point_group_measured_fraction_full 0.622
_diffrn_reflns_point_group_measured_fraction_max 0.622
_diffrn_reflns_theta_full        51.706
_diffrn_reflns_theta_max         51.706
_diffrn_reflns_theta_min         4.736
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
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    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         1273
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0845P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.549
_reflns_Friedel_fraction_full    0.531
_reflns_Friedel_fraction_max     0.532
_reflns_number_gt                959
_reflns_number_total             1273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00435b2.cif
_cod_data_source_block           exp_152_cpp1
_cod_depositor_comments
'Adding full bibliography for 7242817--7242818.cif.'
_cod_database_code               7242817
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 69.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     50.38
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H007-O007
 0.9 with sigma of 0.02
 C12-C11 \\sim C12A-C11
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C11-C16 \\sim C11-C16A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
 C15-C14 \\sim C15A-C14
 with sigma of 0.02
 C14-C13 \\sim C14-C13A
 with sigma of 0.02
 C12-C14 \\sim C12A-C14
 with sigma of 0.04
 C11-C15 \\sim C11-C15A
 with sigma of 0.04
 C11-C13 \\sim C11-C13A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14
 with sigma of 0.04
3. Rigid bond restraints
 C11, C16A, C15A, C13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C11 \\sim C16A \\sim C15A \\sim C13A \\sim C12A: within 2A with sigma of 0.001
and sigma for terminal atoms of 0.001
5. Rigid body (RIGU) restrains
 C11, C16, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(C12A)=Sof(H12A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(C13A)=
 Sof(H13A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C13)=Sof(H13)=FVAR(1)
 Fixed X: H007(-0.062531)
 Fixed Y: H007(0.50821)
 Fixed Z: H007(0.32349)
7.a Ternary CH refined with riding coordinates:
 C2(H2A), C10(H10), C8(H8), C6(H6)
7.b Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B)
7.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C16(H16), C15(H15), C13(H13), C12A(H12A), C16A(H16A),
 C15A(H15A), C13A(H13A)
7.d Fitted hexagon refined as free rotating group:
 C12A(C11,C16A,C15A,C14,C13A)
7.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              99889
_shelx_hkl_checksum              46502
_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 1.638
_oxdiff_exptl_absorpt_empirical_full_min 0.694