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_7248677
_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, C3 H8 O'
_chemical_formula_sum            'C34 H40 Cl4 N4 O5'
_chemical_formula_weight         726.50
_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             2024-05-12
_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                88.206(3)
_cell_angle_beta                 78.488(3)
_cell_angle_gamma                88.798(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4880(3)
_cell_length_b                   9.7666(3)
_cell_length_c                   18.9486(7)
_cell_measurement_reflns_used    7646
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      78.5580
_cell_measurement_theta_min      4.8780
_cell_volume                     1719.52(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.908
_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     40.00  76.00   0.50    0.69    --  109.94-126.00-150.00   72
  2  \w     83.00 108.00   0.50    0.69    --  109.94-126.00-150.00   50
  3  \w     38.00  90.00   0.50    0.17    --   46.83-126.00 -30.00  104
  4  \w     42.00  81.00   0.50    0.17    --   46.83-110.00 -17.00   78
  5  \w     77.00 105.00   0.50    0.69    --  109.94 -95.00 120.00   56
  6  \w     38.00  69.00   0.50    0.69    --  109.94 -95.00 120.00   62
  7  \w     58.00 105.00   0.50    0.69    --  109.94 -95.00  30.00   94
  8  \w     40.00  89.00   0.50    0.69    --  109.94 -95.00-150.00   98
  9  \w    106.00 133.00   0.50    0.69    --  109.94 -88.00 104.02   54
 10  \w     38.00  76.00   0.50    0.69    --  109.94 -30.00  90.00   76
 11  \w     80.00 117.00   0.50    0.69    --  109.94 -30.00  90.00   74
 12  \w     37.00 126.00   0.50    0.69    --  109.94 -77.00 -30.00  178
 13  \w     41.00 131.00   0.50    0.69    --  109.94 -77.00 -90.00  180
 14  \w     48.00 123.00   0.50    0.69    --  109.94 -45.00 -30.00  150
 15  \w     36.00  81.00   0.50    0.17    --   46.83  38.00 -30.00   90
 16  \w    123.00 166.00   0.50    0.69    --  109.94  77.00 150.00   86
 17  \w    104.00 152.00   0.50    0.69    --  109.94 110.00  77.00   96
 18  \w    110.00 164.00   0.50    0.69    --  109.94  77.00  30.00  108
 19  \w     95.00 134.00   0.50    0.69    --  109.94 126.00-120.00   78
 20  \w    138.00 177.00   0.50    0.69    --  109.94 126.00-120.00   78
 21  \w    -37.00  23.00   0.50    0.17    --  -46.83  57.00-150.00  120
 22  \w   -104.00 -21.00   0.50    0.69    --  -91.75  15.00 -60.00  166
 23  \w    -60.00  24.00   0.50    0.17    --  -46.83  38.00 120.00  168
 24  \w    -50.00 -16.00   0.50    0.69    --  -91.75  15.00  60.00   68
 25  \w    -95.00 -68.00   0.50    0.69    --  -91.75  15.00  60.00   54
 26  \w   -131.00 -82.00   0.50    0.69    --  -91.75-110.00 -17.00   98
 27  \w   -150.00-123.00   0.50    0.69    --  -91.75 -77.00 120.00   54
 28  \w   -139.00-112.00   0.50    0.69    --  -91.75 -77.00  90.00   54
 29  \w   -142.00-115.00   0.50    0.69    --  -91.75 -77.00   0.00   54
 30  \w   -162.00-113.00   0.50    0.69    --  -91.75 -77.00-150.00   98
 31  \w   -115.00 -51.00   0.50    0.17    --  -46.83 -38.00 -60.00  128
 32  \w    -66.00  -9.00   0.50    0.17    --  -46.83 110.00  77.00  114
 33  \w    -81.00 -55.00   0.50    0.69    --  -91.75 110.00  77.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0584899000
_diffrn_orient_matrix_UB_12      -0.0100225000
_diffrn_orient_matrix_UB_13      0.0702391000
_diffrn_orient_matrix_UB_21      -0.1449609000
_diffrn_orient_matrix_UB_22      -0.0570700000
_diffrn_orient_matrix_UB_23      0.0403866000
_diffrn_orient_matrix_UB_31      0.0550375000
_diffrn_orient_matrix_UB_32      -0.1468126000
_diffrn_orient_matrix_UB_33      -0.0180249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17521
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.525
_diffrn_reflns_theta_min         4.530
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (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    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'from isopropanol solution'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6716
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1668P)^2^+3.1219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2267
_refine_ls_wR_factor_ref         0.2583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5646
_reflns_number_total             6716
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.8527\% 
around [0.92 0.00 0.38] (reciprocal) or [1.00 -0.02 0.00] (direct)
Component 3 rotated by -176.2958\% 
around [0.95 0.02 0.31] (reciprocal) or [1.00 0.00 -0.02] (direct)
Component 4 rotated by 5.4397\% 
around [0.62 0.69 0.36] (reciprocal) or [0.68 0.73 0.02] (direct)
;
_cod_data_source_file            d4ce00397g2.cif
_cod_data_source_block           twincr_twin2_hklf4
_cod_depositor_comments
'Adding full bibliography for 7248675--7248680.cif.'
_cod_database_code               7248677
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C35H40Cl4N3O5
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.364
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1A-H1A
 0.88 with sigma of 0.01
3. Others
 Sof(H1IA)=1-FVAR(1)
 Sof(H1I)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2I(H2I)
4.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D), C2P(H2PA,H2PB), C3P(H3PA,H3PB), C4P(H4PA,
 H4PB)
4.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 N1B(H1B), C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B)
4.d Idealised Me refined as rotating group:
 C1I(H1IB,H1IC,H1ID), C3I(H3IA,H3IB,H3IC), N1P(H1PA,H1PB,H1PC), N5P(H5PA,H5PB,
 H5PC)
4.e Idealised tetrahedral OH refined as rotating group:
 O1I(H1I), O1I(H1IA)
;
_shelx_res_checksum              75272
_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 4.034
_oxdiff_exptl_absorpt_empirical_full_min 0.516
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               4