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_7245263
_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, 2(C8 H12 N2)'
_chemical_formula_sum            'C44 H46 N6 O4'
_chemical_formula_weight         722.87
_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     dual
_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                91.6280(10)
_cell_angle_beta                 98.4360(10)
_cell_angle_gamma                103.4880(10)
_cell_formula_units_Z            2
_cell_length_a                   9.09200(10)
_cell_length_b                   12.2035(2)
_cell_length_c                   17.7698(3)
_cell_measurement_reflns_used    12755
_cell_measurement_temperature    123
_cell_measurement_theta_max      79.0800
_cell_measurement_theta_min      4.4040
_cell_volume                     1892.49(5)
_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9680
_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    -89.00  18.00   0.50    1.00    --    0.00 -37.00 150.00  214
  2  \w    -26.00  31.00   0.50    1.00    --    0.00  77.00  60.00  114
  3  \w     20.00  65.00   0.50    1.00    --    0.00  77.00   0.00   90
  4  \w    -88.00  19.00   0.50    1.00    --    0.00 -37.00-120.00  214
  5  \w    -30.00   0.00   0.50    1.00    --    0.00  77.00   0.00   60
  6  \w     37.00  78.00   0.50    1.00    --    0.00  37.00 120.00   82
  7  \w     26.00  52.00   0.50    3.50    --  107.20 -82.00-180.00   52
  8  \w     91.00 133.00   0.50    3.50    --  107.20 -82.00   0.00   84
  9  \w    103.00 177.00   0.50    3.50    --  107.20  30.00  90.00  148
 10  \w     20.00 125.00   0.50    3.50    --  107.20 -82.00 -60.00  210
 11  \w    122.00 196.00   0.50    3.50    --  107.20  30.00 150.00  148
 12  \w     21.00 140.00   0.50    3.50    --  107.20 -82.00 120.00  238
 13  \w     34.00 124.00   0.50    3.50    --  107.20 -30.00-180.00  180
 14  \w     63.00 105.00   0.50    3.50    --  107.20 -82.00 -90.00   84
 15  \w     25.00  51.00   0.50    3.50    --  107.20 -82.00   0.00   52
 16  \w     78.00 107.00   0.50    3.50    --  107.20 -82.00  60.00   58
 17  \w     59.00 125.00   0.50    3.50    --  107.20 -30.00 -30.00  132
 18  \w     58.00 125.00   0.50    3.50    --  107.20 -15.00 120.00  134
 19  \w     85.00 138.00   0.50    3.50    --  107.20 -82.00-180.00  106
 20  \w     89.00 194.00   0.50    3.50    --  107.20  30.00-180.00  210
 21  \w     85.00 116.00   0.50    3.50    --  107.20 -61.00 -30.00   62
 22  \w     18.00 115.00   0.50    3.50    --  107.20 -61.00 -60.00  194
 23  \w     21.00 109.00   0.50    3.50    --  107.20 -61.00 120.00  176
;
_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      0.0909061000
_diffrn_orient_matrix_UB_12      0.1063429000
_diffrn_orient_matrix_UB_13      -0.0321244000
_diffrn_orient_matrix_UB_21      -0.1484925000
_diffrn_orient_matrix_UB_22      0.0402014000
_diffrn_orient_matrix_UB_23      -0.0208625000
_diffrn_orient_matrix_UB_31      0.0286830000
_diffrn_orient_matrix_UB_32      0.0632455000
_diffrn_orient_matrix_UB_33      0.0790374000
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21056
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.655
_diffrn_reflns_theta_min         3.733
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56630
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         7977
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0700P)^2^+0.4238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7151
_reflns_number_total             7977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_1099_amr_75c-meno2
_cod_database_code               7245263
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N6, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 1 and sigma for 1-3 distances of 1
3.a Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C)
;
_shelx_res_checksum              52653
_shelx_hkl_checksum              93199
_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 2.935
_oxdiff_exptl_absorpt_empirical_full_min 0.571