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_7245260
_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         'C13 H9 N, 0.5(C10 H8 O2), 0.5(C8 H12 N2)'
_chemical_formula_sum            'C22 H19 N2 O'
_chemical_formula_weight         327.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2bpydd
_audit_creation_date             2022-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-29 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.2050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3133(2)
_cell_length_b                   12.14070(10)
_cell_length_c                   21.2595(3)
_cell_measurement_reflns_used    12665
_cell_measurement_temperature    123
_cell_measurement_theta_max      79.4430
_cell_measurement_theta_min      4.3610
_cell_volume                     3299.71(8)
_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_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -19.00  44.00   0.50    0.62    --    0.00  37.00 -90.00  126
  2  \w      6.00  49.00   0.50    0.62    --    0.00  82.00  30.00   86
  3  \w     49.00  86.00   0.50    0.62    --    0.00  37.00 -90.00   74
  4  \w    -88.00 -28.00   0.50    0.62    --    0.00 -57.00  30.00  120
  5  \w    -29.00  86.00   0.50    0.62    --    0.00  77.00 -30.00  230
  6  \w    -70.00 -44.00   0.50    0.62    --    0.00 -37.00 -60.00   52
  7  \w     56.00 139.00   0.50    2.48    --  107.20 -82.00 -90.00  166
  8  \w     94.00 192.00   0.50    2.48    --  107.20  15.00   0.00  196
  9  \w     41.00 140.00   0.50    2.48    --  107.20 -82.00-180.00  198
 10  \w     91.00 124.00   0.50    2.48    --  107.20  30.00-120.00   66
 11  \w    138.00 187.00   0.50    2.48    --  107.20  30.00-120.00   98
 12  \w     43.00 140.00   0.50    2.48    --  107.20 -82.00 -30.00  194
 13  \w     48.00 125.00   0.50    2.48    --  107.20 -61.00-120.00  154
 14  \w     62.00  89.00   0.50    2.48    --  107.20 -61.00-180.00   54
 15  \w     18.00  96.00   0.50    2.48    --  107.20 -61.00  90.00  156
 16  \w     84.00 110.00   0.50    2.48    --  107.20 -82.00  60.00   52
 17  \w     18.00  77.00   0.50    2.48    --  107.20 -82.00  60.00  118
 18  \w    116.00 195.00   0.50    2.48    --  107.20  30.00 -60.00  158
 19  \w     20.00  56.00   0.50    2.48    --  107.20 -61.00  30.00   72
 20  \w     91.00 188.00   0.50    2.48    --  107.20  30.00 -90.00  194
 21  \w     22.00 116.00   0.50    2.48    --  107.20 -45.00 150.00  188
 22  \w     84.00 109.00   0.50    2.48    --  107.20 -30.00 -60.00   50
 23  \w     51.00 109.00   0.50    2.48    --  107.20 -82.00  90.00  116
 24  \w     51.00  77.00   0.50    2.48    --  107.20 -30.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0946652000
_diffrn_orient_matrix_UB_12      0.0656272000
_diffrn_orient_matrix_UB_13      -0.0079277000
_diffrn_orient_matrix_UB_21      0.0420126000
_diffrn_orient_matrix_UB_22      0.0102437000
_diffrn_orient_matrix_UB_23      0.0750308000
_diffrn_orient_matrix_UB_31      0.0615989000
_diffrn_orient_matrix_UB_32      -0.1081113000
_diffrn_orient_matrix_UB_33      0.0023231000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17649
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.919
_diffrn_reflns_theta_min         4.331
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84576
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_preparation       SDG
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0481P)^2^+1.9233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3401
_reflns_number_total             3559
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_953_am-r-5c
_cod_original_cell_volume        3299.71(7)
_cod_database_code               7245260
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.883
_olex2_refinement_description
;
;
_shelx_res_checksum              91694
_shelx_hkl_checksum              98551
_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 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.665