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_7248679
_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, 1.002(C2 H6 O), 2(H2 O)'
_chemical_formula_sum            'C33.01 H42.01 Cl4 N4 O7'
_chemical_formula_weight         748.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-13
_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                84.791(2)
_cell_angle_beta                 89.345(3)
_cell_angle_gamma                88.234(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4529(4)
_cell_length_b                   10.1381(2)
_cell_length_c                   19.0267(6)
_cell_measurement_reflns_used    14768
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      28.3620
_cell_measurement_theta_min      2.0090
_cell_volume                     1814.95(10)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.975
_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   10.00    --   20.00  54.00 153.45  368
  2  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00   8.90  368
  3  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00-146.13  368
  4  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00-146.13  368
  5  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00 -93.84  368
  6  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00 -93.84  368
  7  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00 -48.20  368
  8  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00 120.00  368
  9  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00 -69.88  368
 10  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00-180.00  368
 11  \w    -74.00 110.00   0.50   10.00    --   20.00  54.00 -30.00  368
 12  \w    -67.00 -32.00   0.50   10.00    --   20.00  54.00  60.00   70
 13  \w    -74.00 -48.00   0.50   10.00    --   20.00  54.00 150.00   52
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0282223000
_diffrn_orient_matrix_UB_12      0.0410728000
_diffrn_orient_matrix_UB_13      0.0243080000
_diffrn_orient_matrix_UB_21      -0.0258025000
_diffrn_orient_matrix_UB_22      -0.0429427000
_diffrn_orient_matrix_UB_23      0.0284671000
_diffrn_orient_matrix_UB_31      0.0646045000
_diffrn_orient_matrix_UB_32      -0.0375360000
_diffrn_orient_matrix_UB_33      0.0003731000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            59277
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91594
_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    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method 'from ethanol-water reaction solution'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         9918
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1119P)^2^+0.7661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.2059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6297
_reflns_number_total             9918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00397g2.cif
_cod_data_source_block           exp_392_cr_auto
_cod_depositor_comments
'Adding full bibliography for 7248675--7248680.cif.'
_cod_database_code               7248679
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C33H40Cl4N4O6
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.861
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1B-H1B = N1A-H1A
 0.86 with sigma of 0.02
 C3PB-C2PB = C4PB-C3PB = C2PA-C3PA = C3PA-C4PA
 1.5 with sigma of 0.01
 N1PA-C2PA = N1PB-C2PB = N5PA-C4PA = N5PB-C4PB
 1.48 with sigma of 0.01
3. Rigid bond restraints
 O1T, C1T, C2T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1E \\sim C1E \\sim C2E: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
O1O \\sim C1O \\sim C2O: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
O1T \\sim C1T \\sim C2T: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
Uanis(C2T) = Uanis(C2E)
Uanis(C1T) = Uanis(C1E)
5. Rigid body (RIGU) restrains
 O1O, C1O, C2O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1E, C1E, C2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1T, C1T, C2T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(O1T)+Sof(H1T)+Sof(C1T)+Sof(H1TA)+Sof(H1TB)+Sof(C2T)+Sof(H2TA)+
 Sof(H2TB)+Sof(H2TC)]+1*[Sof(O1O)+Sof(H1O)+Sof(C1O)+Sof(H1OA)+Sof(H1OB)+
 Sof(C2O)+Sof(H2OA)+Sof(H2OB)+Sof(H2OC)]+1*[Sof(O1E)+Sof(H1E)+Sof(C1E)+
 Sof(H1EA)+Sof(H1EB)+Sof(C2E)+Sof(H2EA)+Sof(H2EB)+Sof(H2EC)]=1 with esd of 0.001
 Sof(N1PB)=Sof(H1PA)=Sof(H1PB)=Sof(H1PC)=Sof(C2PB)=Sof(H2PA)=Sof(H2PB)=
 Sof(C3PB)=Sof(H3PA)=Sof(H3PB)=Sof(C4PB)=Sof(H4PA)=Sof(H4PB)=Sof(N5PB)=
 Sof(H5PA)=Sof(H5PB)=Sof(H5PC)=1-FVAR(1)
 Sof(C2PA)=Sof(H2PC)=Sof(H2PD)=Sof(C3PA)=Sof(H3PC)=Sof(H3PD)=Sof(C4PA)=
 Sof(H4PC)=Sof(H4PD)=Sof(N5PA)=Sof(H5PD)=Sof(H5PE)=Sof(H5PF)=Sof(N1PA)=
 Sof(H1PD)=Sof(H1PE)=Sof(H1PF)=FVAR(1)
 Sof(O1T)=Sof(H1T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=
 Sof(H2TC)=FVAR(2)
 Sof(O1O)=Sof(H1O)=Sof(C1O)=Sof(H1OA)=Sof(H1OB)=Sof(C2O)=Sof(H2OA)=Sof(H2OB)=
 Sof(H2OC)=FVAR(3)
 Sof(O1E)=Sof(H1E)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=
 Sof(H2EC)=FVAR(4)
7.a Free rotating group:
 O1E(C1E,C2E), O1O(C1O,C2O), O1T(C1T,C2T), O1W(H1WA,H1WB), O2W(H2WA,H2WB)
7.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D), C1E(H1EA,H1EB), C1O(H1OA,H1OB), C2PB(H2PA,
 H2PB), C3PB(H3PA,H3PB), C4PB(H4PA,H4PB), C2PA(H2PC,H2PD), C3PA(H3PC,H3PD),
 C4PA(H4PC,H4PD), C1T(H1TA,H1TB)
7.c Me refined with riding coordinates:
 C2E(H2EA,H2EB,H2EC), C2O(H2OA,H2OB,H2OC), C2T(H2TA,H2TB,H2TC)
7.d Aromatic/amide H refined with riding coordinates:
 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)
7.e Idealised Me refined as rotating group:
 N1PB(H1PA,H1PB,H1PC), N5PB(H5PA,H5PB,H5PC), N5PA(H5PD,H5PE,H5PF), N1PA(H1PD,
 H1PE,H1PF)
7.f Idealised tetrahedral OH refined as rotating group:
 O1E(H1E), O1O(H1O), O1T(H1T)
;
_shelx_res_checksum              68648
_olex2_exptl_crystal_mounting_method
'coated in Paratone-N and mounted on a MiTeGen mount'
_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.916