New diclofenac salts with the dense hydrogen bond donor propane-1,3-diaminium
Breckell, Jaxon R.; Conte, Luke; Potts, Michael W.; Sawant, Pradnya S.; Butcher, Raymond J.; Vernekar, Beena K.; Richardson, Christopher; CrystEngComm 26 (2024) 3206–3216; doi:10.1039/D4CE00397G

data_7248680
_publ_section_title
;
 New diclofenac salts with the dense hydrogen bond donor
 propane-1,3-diaminium
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              3206
_journal_page_last               3216
_journal_paper_doi               10.1039/D4CE00397G
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C14 H10 Cl2 N O2), C3 H12 N2, 4(H2 O)'
_chemical_formula_sum            'C31 H40 Cl4 N4 O8'
_chemical_formula_weight         738.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-05-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.35740(10)
_cell_length_b                   36.5523(5)
_cell_length_c                   10.2282(2)
_cell_measurement_reflns_used    61150
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      29.8480
_cell_measurement_theta_min      1.9890
_cell_volume                     3498.39(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(1)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    -74.00 110.00   0.50    7.00    --   20.00  54.00  27.68  368
  2  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 175.69  368
  3  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 -98.19  368
  4  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 109.71  368
  5  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 126.11  368
  6  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00  42.96  368
  7  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00-165.45  368
  8  \w     -6.00  84.00   0.50    7.00    --   20.00  54.00 -81.24  180
  9  \w     -6.00  84.00   0.50    7.00    --   20.00  54.00 -81.24  180
 10  \w     78.00 104.00   0.50    7.00    --   20.00  54.00 136.92   52
 11  \w    -49.00  83.00   0.50    7.00    --   20.00  54.00 150.00  264
 12  \w    -33.00  -8.00   0.50    7.00    --   20.00  54.00  60.00   50
 13  \w      4.00  30.00   0.50    7.00    --   20.00  54.00  60.00   52
 14  \w     48.00  74.00   0.50    7.00    --   20.00  54.00  60.00   52
 15  \w    -21.00  90.00   0.50    7.00    --   20.00  54.00  90.00  222
 16  \w     -7.00 110.00   0.50    7.00    --   20.00  54.00  32.87  234
 17  \w    -28.00 110.00   0.50    7.00    --   20.00  54.00 -62.26  276
 18  \w    -38.00 -13.00   0.50    7.00    --   20.00  54.00 -90.00   50
 19  \w     43.00  68.00   0.50    7.00    --   20.00  54.00 -90.00   50
 20  \w    -17.00   8.00   0.50    7.00    --   20.00  54.00-156.58   50
 21  \w     37.00  63.00   0.50    7.00    --   20.00  54.00-156.58   52
 22  \w     32.00  81.00   0.50    7.00    --   20.00  54.00 -30.00   98
 23  \w    -73.00 110.00   0.50    7.00    --   20.00  54.00 -10.32  366
 24  \w     79.00 105.00   0.50    7.00    --   20.00  54.00  76.02   52
 25  \w    -73.00 110.00   0.50    7.00    --   20.00  54.00  16.06  366
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            155834
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.391
_diffrn_reflns_theta_min         1.991
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.402
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1544
_exptl_crystal_recrystallization_method
'slow evaporation from isopropanol water'
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 7228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         20631
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.3664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                16914
_reflns_number_total             20631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00397g2.cif
_cod_data_source_block           exp_396_criproh_auto
_cod_depositor_comments
'Adding full bibliography for 7248675--7248680.cif.'
_cod_database_code               7248680
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.819
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N1D-H1D = N1C-H1C = N1B-H1B = N1A-H1A
 0.85 with sigma of 0.02
3. Others
 Sof(O8WA)=Sof(H8WA)=Sof(H8WB)=1-FVAR(1)
 Sof(O8WB)=Sof(H8WC)=Sof(H8WD)=FVAR(1)
 Fixed X: O4W(0.76706) H4WA(0.72742) H4WB(0.853361)
 Fixed Y: O4W(0.55293) H4WA(0.55583) H4WB(0.55932)
 Fixed Z: O4W(0.02495) H4WA(-0.04918) H4WB(0.01296)
4.a Free rotating group:
 O6W(H6WA,H6WB), O3W(H3WA,H3WB), O5W(H5WA,H5WB), O8WA(H8WA,H8WB), O1W(H1WA,
 H1WB), O7W(H7WA,H7WB), O2W(H2WA,H2WB), O8WB(H8WC,H8WD)
4.b Secondary CH2 refined with riding coordinates:
 C13C(H13A,H13B), C13D(H13C,H13D), C13A(H13E,H13F), C13B(H13G,H13H), C2P(H2PA,
 H2PB), C3P(H3PA,H3PB), C4P(H4PA,H4PB), C2N(H2NA,H2NB), C3N(H3NA,H3NB),
 C4N(H4NA,H4NB)
4.c Aromatic/amide H refined with riding coordinates:
 C3C(H3C), C4C(H4C), C5C(H5C), C8C(H8C), C9C(H9C), C10C(H10C), C11C(H11C),
 C3D(H3D), C4D(H4D), C5D(H5D), C8D(H8D), C9D(H9D), C10D(H10D), C11D(H11D),
 C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B)
4.d Idealised Me refined as rotating group:
 N1P(H1PA,H1PB,H1PC), N5P(H5PA,H5PB,H5PC), N1N(H1NA,H1NB,H1NC), N5N(H5NA,H5NB,
 H5NC)
;
_shelx_res_checksum              52810
_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
;