Ternary and quaternary cocrystals of 2,7-dihydroxynaphthalene: systematic design with a large synthon module
Ahsan, Mollah Rohan; Mukherjee, Arijit; CrystEngComm  (2022) –; doi:10.1039/D2CE00735E

data_7245267
_publ_section_title
;
 Ternary and quaternary cocrystals of 2,7-dihydroxynaphthalene: systematic
 design with a large synthon module
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00735E
_journal_year                    2022
_chemical_formula_moiety         '2(C10 H8 O2), C8 H6 N2, 3(C8 H12 N2), C16 H10'
_chemical_formula_sum            'C68 H68 N8 O4'
_chemical_formula_weight         1061.30
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-08 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                84.4970(10)
_cell_angle_beta                 76.1030(10)
_cell_angle_gamma                89.9670(10)
_cell_formula_units_Z            2
_cell_length_a                   12.1268(2)
_cell_length_b                   13.0290(2)
_cell_length_c                   18.1703(2)
_cell_measurement_reflns_used    17930
_cell_measurement_temperature    123.00
_cell_measurement_theta_max      79.5950
_cell_measurement_theta_min      5.0090
_cell_volume                     2773.28(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.963
_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    -66.00 -24.00   0.50    3.36    --    0.00 -57.00  60.00   84
  2  \w    -36.00  23.00   0.50    3.36    --    0.00 -57.00-120.00  118
  3  \w    -32.00  89.00   0.50    3.36    --    0.00  82.00  30.00  242
  4  \w    -13.00  20.00   0.50    3.36    --    0.00 -57.00  60.00   66
  5  \w     28.00  54.00   0.50    3.36    --    0.00  37.00-120.00   52
  6  \w    -89.00  18.00   0.50    3.36    --    0.00 -37.00 -30.00  214
  7  \w     36.00  62.00   0.50   13.44    --  107.20 -30.00 120.00   52
  8  \w     27.00 125.00   0.50   13.44    --  107.20 -82.00   0.00  196
  9  \w     20.00  95.00   0.50   13.44    --  107.20 -45.00 -30.00  150
 10  \w     19.00 122.00   0.50   13.44    --  107.20 -82.00 -60.00  206
 11  \w     50.00 134.00   0.50   13.44    --  107.20 -82.00 120.00  168
 12  \w     31.00 122.00   0.50   13.44    --  107.20 -15.00  90.00  182
 13  \w     96.00 122.00   0.50   13.44    --  107.20 -82.00  60.00   52
 14  \w     98.00 124.00   0.50   13.44    --  107.20 -82.00 -90.00   52
 15  \w     26.00 126.00   0.50   13.44    --  107.20 -30.00   0.00  200
 16  \w     23.00  54.00   0.50   13.44    --  107.20 -82.00 -90.00   62
 17  \w    121.00 187.00   0.50   13.44    --  107.20  30.00-180.00  132
 18  \w     56.00 121.00   0.50   13.44    --  107.20 -45.00-180.00  130
 19  \w     88.00 113.00   0.50   13.44    --  107.20  30.00-180.00   50
 20  \w     81.00 132.00   0.50   13.44    --  107.20 -61.00-150.00  102
 21  \w     71.00 118.00   0.50   13.44    --  107.20 -82.00-120.00   94
 22  \w     77.00 126.00   0.50   13.44    --  107.20 -30.00 120.00   98
 23  \w     18.00 126.00   0.50   13.44    --  107.20 -61.00 120.00  216
 24  \w     36.00  61.00   0.50   13.44    --  107.20 -82.00 -30.00   50
 25  \w     95.00 131.00   0.50   13.44    --  107.20 -82.00 -30.00   72
 26  \w     82.00 197.00   0.50   13.44    --  107.20  15.00 120.00  230
 27  \w     90.00 115.00   0.50   13.44    --  107.20 -82.00-180.00   50
 28  \w     54.00  80.00   0.50   13.44    --  107.20 -82.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34102
_diffrn_reflns_point_group_measured_fraction_full 0.690
_diffrn_reflns_point_group_measured_fraction_max 0.651
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.882
_diffrn_reflns_theta_min         3.986
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1782
_refine_ls_number_reflns         15752
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0485
_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^)+(0.1003P)^2^+0.1505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.351
_reflns_Friedel_fraction_full    0.384
_reflns_Friedel_fraction_max     0.338
_reflns_number_gt                14176
_reflns_number_total             15752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           10
_cod_database_code               7245267
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Uiso: H79(0.0472) H85B(0.0456)
3.a Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C70(H70A,H70B,H70C), C73(H73A,H73B,H73C), C86(H86A,H86B,
 H86C), C89(H89A,H89B,H89C), C93(H93A,H93B,H93C), C94(H94A,H94B,H94C), C97(H97A,
 H97B,H97C), C117(H11D,H11E,H11F), C118(H11G,H11H,H11I), C121(H12A,H12B,H12C),
 C130(H13A,H13B,H13C), C133(H13D,H13E,H13F), C134(H13G,H13H,H13I), C137(H13J,
 H13K,H13L), C138(H13M,H13N,H13O), C141(H14A,H14B,H14C), C142(H14D,H14E,H14F)
3.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              2038
_shelx_hkl_checksum              98136
_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
;