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_7242818
_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         'C17 H22 N3 Na O6 S, C3 H6 O2'
_chemical_formula_sum            'C20 H28 N3 Na O8 S'
_chemical_formula_weight         493.50
_chemical_name_common            'amoxicillin sodium solvate'
_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             2020-09-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_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                   9.9361(7)
_cell_length_b                   15.3223(10)
_cell_length_c                   15.6894(9)
_cell_measurement_reflns_used    7723
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.4520
_cell_measurement_theta_min      1.8920
_cell_volume                     2388.6(3)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -115.00  65.00   0.25    8.00    --  -25.00  45.00   0.00  720
  2  \w   -115.00  65.00   0.25    8.00    --  -25.00  45.00  90.00  720
  3  \w   -115.00  65.00   0.25    8.00    --  -25.00  45.00 180.00  720
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225017000
_diffrn_orient_matrix_UB_12      -0.0174270000
_diffrn_orient_matrix_UB_13      -0.0393922000
_diffrn_orient_matrix_UB_21      -0.0255247000
_diffrn_orient_matrix_UB_22      -0.0415367000
_diffrn_orient_matrix_UB_23      0.0116668000
_diffrn_orient_matrix_UB_31      -0.0627521000
_diffrn_orient_matrix_UB_32      0.0106982000
_diffrn_orient_matrix_UB_33      -0.0188625000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28794
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.858
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33906
_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    1.372
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_coef       0.0032(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5682
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.3400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4338
_reflns_number_total             5682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00435b2.cif
_cod_data_source_block           r20200913e
_cod_depositor_comments
'Adding full bibliography for 7242817--7242818.cif.'
_cod_database_code               7242818
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H30N3O5SNa
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 95.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.90
_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, All O(H) groups
2. Restrained distances
 O8-H8
 0.85 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00N(H00N), C00O(H00O)
3.b Secondary CH2 refined with riding coordinates:
 N00A(H00A,H00B)
3.c Aromatic/amide H refined with riding coordinates:
 N00B(H00C), C00G(H00G), C00M(H00M), C00P(H00P), C00R(H00R)
3.d Idealised Me refined as rotating group:
 C00S(H00D,H00E,H00H), C00T(H00I,H00K,H00L), C00U(H00Q,H00S,H00T), C00W(H00U,
 H00V,H00W), C00X(H00X,H00Y,H)
3.e Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_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 2.263
_oxdiff_exptl_absorpt_empirical_full_min 0.666