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_7245259
_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, 2(C10 H8 O2), 2(C8 H12 N2)'
_chemical_formula_sum            'C49 H49 N5 O4'
_chemical_formula_weight         771.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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
;
2022-06-30 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.863(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6173(4)
_cell_length_b                   9.16000(10)
_cell_length_c                   22.6182(3)
_cell_measurement_reflns_used    19322
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      79.1630
_cell_measurement_theta_min      4.5270
_cell_volume                     4030.14(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.979
_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     15.00  88.00   0.50    3.60    --    0.00  37.00 120.00  146
  2  \w    -32.00  88.00   0.50    3.60    --    0.00  82.00 -60.00  240
  3  \w    -84.00 -35.00   0.50    3.60    --    0.00 -82.00 -60.00   98
  4  \w    -12.00  63.00   0.50    3.60    --    0.00  37.00  60.00  150
  5  \w    -21.00  14.00   0.50    3.60    --    0.00 -57.00-180.00   70
  6  \w    -32.00  29.00   0.50    3.60    --    0.00 -82.00 -60.00  122
  7  \w     84.00 145.00   0.50   14.42    --  107.20  61.00-120.00  122
  8  \w     87.00 127.00   0.50   14.42    --  107.20  45.00   0.00   80
  9  \w     25.00 135.00   0.50   14.42    --  107.20 -82.00  90.00  220
 10  \w     19.00 134.00   0.50   14.42    --  107.20 -15.00 -90.00  230
 11  \w     95.00 124.00   0.50   14.42    --  107.20 -82.00-180.00   58
 12  \w     18.00  69.00   0.50   14.42    --  107.20 -30.00-180.00  102
 13  \w     90.00 127.00   0.50   14.42    --  107.20 -30.00-180.00   74
 14  \w     44.00 136.00   0.50   14.42    --  107.20 -82.00 -60.00  184
 15  \w     23.00 127.00   0.50   14.42    --  107.20 -30.00 -60.00  208
 16  \w     70.00 111.00   0.50   14.42    --  107.20 -82.00   0.00   82
 17  \w     18.00 121.00   0.50   14.42    --  107.20 -61.00 150.00  206
 18  \w     22.00 108.00   0.50   14.42    --  107.20 -61.00  90.00  172
 19  \w     89.00 197.00   0.50   14.42    --  107.20  30.00 -60.00  216
 20  \w     50.00  75.00   0.50   14.42    --  107.20 -82.00  30.00   50
 21  \w     88.00 113.00   0.50   14.42    --  107.20 -82.00  30.00   50
 22  \w     84.00 137.00   0.50   14.42    --  107.20 -82.00 150.00  106
 23  \w    169.00 195.00   0.50   14.42    --  107.20  61.00-120.00   52
 24  \w     83.00 128.00   0.50   14.42    --  107.20 -45.00  90.00   90
 25  \w    165.00 193.00   0.50   14.42    --  107.20  45.00   0.00   56
 26  \w     68.00 139.00   0.50   14.42    --  107.20 -82.00-120.00  142
 27  \w     78.00 127.00   0.50   14.42    --  107.20  82.00  60.00   98
 28  \w     48.00  73.00   0.50   14.42    --  107.20 -82.00 -30.00   50
 29  \w     85.00 110.00   0.50   14.42    --  107.20 -82.00 -30.00   50
 30  \w    146.00 183.00   0.50   14.42    --  107.20  15.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: 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      -0.0033748000
_diffrn_orient_matrix_UB_12      -0.1570303000
_diffrn_orient_matrix_UB_13      0.0227381000
_diffrn_orient_matrix_UB_21      -0.0013996000
_diffrn_orient_matrix_UB_22      0.0598452000
_diffrn_orient_matrix_UB_23      0.0630930000
_diffrn_orient_matrix_UB_31      -0.0791052000
_diffrn_orient_matrix_UB_32      0.0057085000
_diffrn_orient_matrix_UB_33      -0.0351344000
_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  0.0870
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            49639
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.008
_diffrn_reflns_theta_min         3.927
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46503
_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    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00024(7)
_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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         8618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0735P)^2^+2.2274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7647
_reflns_number_total             8618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_1066-18-c-lsam-2a
_cod_database_code               7245259
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              65514
_shelx_hkl_checksum              87802
_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 4.989
_oxdiff_exptl_absorpt_empirical_full_min 0.290