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_7245264
_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
'C16 H10, 2(C13 H9 N), 2(C10 H8 O2), 2(C8 H12 N2)'
_chemical_formula_sum            'C78 H68 N6 O4'
_chemical_formula_weight         1153.38
_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     iterative
_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
;
2022-07-07 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                91.725(2)
_cell_angle_beta                 104.910(2)
_cell_angle_gamma                102.633(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2111(3)
_cell_length_b                   11.8322(4)
_cell_length_c                   14.3846(4)
_cell_measurement_reflns_used    7563
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.5540
_cell_measurement_theta_min      3.2030
_cell_volume                     1472.07(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_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    -41.00 -15.00   0.50    1.74    --    0.00 -19.00   0.00   52
  2  \w    -85.00 -51.00   0.50    1.74    --    0.00 -19.00   0.00   68
  3  \w    -39.00  31.00   0.50    1.74    --    0.00 -82.00-150.00  140
  4  \w    -84.00  16.00   0.50    1.74    --    0.00 -57.00 120.00  200
  5  \w    -19.00  46.00   0.50    1.74    --    0.00  40.00  -4.00  130
  6  \w    -67.00 -41.00   0.50    1.74    --    0.00 -82.00-150.00   52
  7  \w     19.00 140.00   0.50    6.97    --  107.20 -82.00  30.00  242
  8  \w     87.00 196.00   0.50    6.97    --  107.20  45.00-180.00  218
  9  \w     32.00  58.00   0.50    6.97    --  107.20 -15.00   0.00   52
 10  \w     77.00 129.00   0.50    6.97    --  107.20 -82.00 120.00  104
 11  \w     85.00 126.00   0.50    6.97    --  107.20 -30.00-180.00   82
 12  \w     21.00 132.00   0.50    6.97    --  107.20 -61.00-120.00  222
 13  \w     20.00  68.00   0.50    6.97    --  107.20 -61.00 120.00   96
 14  \w     75.00 113.00   0.50    6.97    --  107.20 -61.00 120.00   76
 15  \w     20.00  70.00   0.50    6.97    --  107.20 -82.00 120.00  100
 16  \w     19.00 140.00   0.50    6.97    --  107.20 -82.00-120.00  242
 17  \w     80.00 195.00   0.50    6.97    --  107.20  15.00-120.00  230
 18  \w     88.00 116.00   0.50    6.97    --  107.20 -82.00 -30.00   56
 19  \w    102.00 134.00   0.50    6.97    --  107.20 -15.00-150.00   64
 20  \w    139.00 172.00   0.50    6.97    --  107.20  15.00 -30.00   66
 21  \w     26.00  96.00   0.50    6.97    --  107.20 -61.00  30.00  140
 22  \w     91.00 117.00   0.50    6.97    --  107.20 -82.00-180.00   52
 23  \w     27.00  96.00   0.50    6.97    --  107.20 -15.00-150.00  138
 24  \w     88.00 113.00   0.50    6.97    --  107.20 -82.00  60.00   50
 25  \w     73.00 135.00   0.50    6.97    --  107.20 -15.00   0.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1653742000
_diffrn_orient_matrix_UB_12      -0.0712734000
_diffrn_orient_matrix_UB_13      -0.0096162000
_diffrn_orient_matrix_UB_21      0.0659528000
_diffrn_orient_matrix_UB_22      -0.0943872000
_diffrn_orient_matrix_UB_23      0.0564568000
_diffrn_orient_matrix_UB_31      0.0004991000
_diffrn_orient_matrix_UB_32      0.0629729000
_diffrn_orient_matrix_UB_33      0.0954325000
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15805
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         3.193
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         5942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0627
_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^)+(0.1331P)^2^+0.1984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4986
_reflns_number_total             5942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_969_am-r-19c-crysalispro
_cod_database_code               7245264
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.884
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C39(H39), C43(H43)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              43576
_shelx_hkl_checksum              85006
_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 2.862
_oxdiff_exptl_absorpt_empirical_full_min 0.463