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_7248676
_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(C H4 O)'
_chemical_formula_sum            'C33 H40 Cl4 N4 O6'
_chemical_formula_weight         730.49
_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
_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                88.365(2)
_cell_angle_beta                 79.728(3)
_cell_angle_gamma                88.551(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6753(3)
_cell_length_b                   9.9173(3)
_cell_length_c                   19.0010(5)
_cell_measurement_reflns_used    12822
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      29.4990
_cell_measurement_theta_min      2.0540
_cell_volume                     1792.87(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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.980
_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   15.00    --   20.00  54.00-135.01  368
  2  \w    -74.00 110.00   0.50   15.00    --   20.00  54.00 -30.00  368
  3  \w    -74.00 110.00   0.50   15.00    --   20.00  54.00  97.79  368
  4  \w    -74.00 110.00   0.50   15.00    --   20.00  54.00  30.00  368
  5  \w    -74.00 110.00   0.50   15.00    --   20.00  54.00 155.61  368
  6  \w    -74.00 110.00   0.50   15.00    --   20.00  54.00-123.89  368
  7  \w    -74.00  26.00   0.50   15.00    --   20.00  54.00 -60.00  200
;
_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  0.0250
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34574
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.055
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85697
_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    1.353
_exptl_crystal_description       irregular
_exptl_crystal_F_000             764
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         8719
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0547P)^2^+0.6399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6465
_reflns_number_total             8719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00397g2.cif
_cod_data_source_block           exp_351_jrb1-022_auto
_cod_depositor_comments
'Adding full bibliography for 7248675--7248680.cif.'
_cod_original_cell_volume        1792.87(10)
_cod_database_code               7248676
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.805
_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,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N7-H7
 0.85 with sigma of 0.02
 N41-C17
 1.45 with sigma of 0.02
 N45-C19
 1.45 with sigma of 0.02
 C18-C17
 1.55 with sigma of 0.02
 C19-C18
 1.55 with sigma of 0.02
 N26-H26
 0.85 with sigma of 0.02
 O6A-C7A = O6-C7
 1.35 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C42) = Uanis(C17)
Uanis(C43) = Uanis(C18)
Uanis(C44) = Uanis(C19)
Uanis(C7) = Uanis(C7A)
4. Rigid body (RIGU) restrains
 C19, N45, H45A, H45B, H45C, H45D, H45E, H45F, C44, C43, H44A, H44B, H19A,
 H19B, C18, H43A, H43B, C42, H18A, H18B, C17, H42A, H42B, N41, H17A, H17B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O2)=Sof(O4)=1-FVAR(1)
 Sof(O1)=Sof(O3)=FVAR(1)
 Sof(H45D)=Sof(H45E)=Sof(H45F)=Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 1-FVAR(2)
 Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C42)=Sof(H42A)=Sof(H42B)=
 FVAR(2)
 Sof(O6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=1-FVAR(3)
 Sof(O6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C33(H33A,H33B), C43(H43A,H43B), C44(H44A,H44B), C42(H42A,
 H42B), C19(H19A,H19B), C18(H18A,H18B), C17(H17A,H17B)
6.b Me refined with riding coordinates:
 N41(H41A,H41B,H41C)
6.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C5(H5), C3(H3), C28(H28), C4(H4), C11(H11), C10(H10),
 C22(H22), C31(H31), C29(H29), C30(H30), C23(H23), C24(H24)
6.d Idealised Me refined as rotating group:
 N45(H45A,H45B,H45C), N45(H45D,H45E,H45F), N41(H41D,H41E,H41F), C7(H7A,H7B,
 H7C), C16(H16A,H16B,H16C), C7A(H7AA,H7AB,H7AC)
6.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6), O6A(H6A)
;
_shelx_res_checksum              21713
_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
;