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_7248678
_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_formula_moiety
'2(C14 H10 Cl2 N O2), C3 H12 N2, 2(C2 H6 O1 S1)'
_chemical_formula_sum            'C35 H44 Cl4 N4 O6 S2'
_chemical_formula_weight         822.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-13 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6066(5)
_cell_length_b                   43.035(2)
_cell_length_c                   9.7812(5)
_cell_measurement_reflns_used    10306
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      24.9700
_cell_measurement_theta_min      1.9140
_cell_volume                     4043.7(3)
_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      294.0(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_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   35.00    --   20.00  54.00 148.12  368
  2  \w    -74.00 110.00   0.50   35.00    --   20.00  54.00  88.67  368
  3  \w    -74.00 110.00   0.50   35.00    --   20.00  54.00-149.63  368
  4  \w    -74.00  38.00   0.50   35.00    --   20.00  54.00 -30.84  224
;
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43370
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.387
_diffrn_reflns_theta_min         2.552
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88677
_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    1.351
_exptl_crystal_description       rod
_exptl_crystal_F_000             1720
_exptl_crystal_recrystallization_method dimethylsulfoxide
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5935
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0665
_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^)+(0.0785P)^2^+3.4967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3840
_reflns_number_total             5935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00397g2.cif
_cod_data_source_block           exp_375_cr_auto
_cod_depositor_comments
'Adding full bibliography for 7248675--7248680.cif.'
_cod_original_cell_volume        4043.7(4)
_cod_database_code               7248678
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.806
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.85 with sigma of 0.02
 S1B-C2B = S1A-C2A = S1B-C1B = S1A-C1A
 1.75 with sigma of 0.02
 S1B-O1B
 1.5 with sigma of 0.02
 S1A-O1A
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
S1A \\sim O1A \\sim C1A \\sim C2A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
S1B \\sim O1B \\sim C1B \\sim C2B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 S1B, O1B, C1B, C2B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1A, O1A, C1A, C2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S1B)=Sof(O1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=Sof(H2BC)=1-FVAR(1)
 Sof(S1A)=Sof(O1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(H2AC)=FVAR(1)
 Fixed Sof: H3SA(0.5) H3SB(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C2S(H2SA,H2SB), C3S(H3SA,H3SB)
6.b Me refined with riding coordinates:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,
 H2BC)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
6.d Idealised Me refined as rotating group:
 N1S(H1SA,H1SB,H1SC)
;
_shelx_res_checksum              22620
_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
;