Agomelatine–hydroquinone (1:1) cocrystal: novel polymorphs and their thermodynamic relationship
Lee, Min-Jeong; Aitipamula, Srinivasulu; Choi, Guang J.; Chow, Pui Shan; Acta Crystallographica Section B 75 (2019) –; doi:10.1107/S2052520619011739

data_2108512
_publ_section_title
;
 Agomelatine--hydroquinone (1:1) cocrystal: novel polymorphs and their
 thermodynamic relationship
;
_journal_coeditor_code           RM5017SUP1
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520619011739
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 N O2, C6 H6 O2'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.20150(10)
_cell_length_b                   12.23260(10)
_cell_length_c                   21.3487(3)
_cell_measurement_reflns_used    7942
_cell_measurement_temperature    297.56(16)
_cell_measurement_theta_max      72.3450
_cell_measurement_theta_min      5.4650
_cell_volume                     1880.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.56(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_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      2.00 122.00   1.00    1.00    --   37.50  57.00   0.00  120
  2  \w    116.00 177.00   1.00    1.00    --  109.79  83.00-138.00   61
  3  \w    144.00 176.00   1.00    1.00    --  109.79  77.00 -90.00   32
  4  \w    139.00 178.00   1.00    1.00    --  109.79  30.00 -90.00   39
  5  \w    103.00 178.00   1.00    1.00    --  109.79 111.00-180.00   75
  6  \w     81.00 126.00   1.00    1.00    --  109.79  30.00 -90.00   45
  7  \w     76.00 127.00   1.00    1.00    --  109.79  77.00 -90.00   51
  8  \w     74.00 130.00   1.00    1.00    --  109.79  45.00-150.00   56
  9  \w     40.00  69.00   1.00    1.00    --   37.50 -38.00-120.00   29
 10  \w     24.00 100.00   1.00    1.00    --   37.50-125.00-150.00   76
 11  \w     29.00 116.00   1.00    1.00    --  109.79-111.00  30.00   87
 12  \w     54.00 144.00   1.00    1.00    --  109.79 -83.00 101.00   90
 13  \w     58.00  83.00   1.00    1.00    --   37.50 -99.00  60.00   25
 14  \w     -3.00  46.00   1.00    1.00    --   37.50 -83.00 101.00   49
 15  \w      2.00  54.00   1.00    1.00    --   37.50 -99.00  60.00   52
 16  \w    -13.00  12.00   1.00   10.00    --    0.00 -83.00 101.00   25
 17  \w    -47.00  35.00   1.00    1.00    --   37.50 -38.00-120.00   82
 18  \w    -24.00   1.00   1.00   10.00    --    0.00  83.00-138.00   25
 19  \w     74.00 177.00   1.00    1.00    --  109.79  77.00 150.00  103
 20  \w     66.00 149.00   1.00    1.00    --  109.79 178.00   0.00   83
 21  \w     57.00 150.00   1.00    1.00    --  109.79 178.00  60.00   93
 22  \w    -39.00  -1.00   1.00    1.00    --  -37.50  83.00-138.00   38
 23  \w   -111.00 -77.00   1.00    1.00    --  -37.50 -83.00 101.00   34
 24  \w   -123.00 -82.00   1.00    1.00    --  -37.50 -99.00   0.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1192753000
_diffrn_orient_matrix_UB_12      0.0053626000
_diffrn_orient_matrix_UB_13      0.0598225000
_diffrn_orient_matrix_UB_21      -0.1036561000
_diffrn_orient_matrix_UB_22      -0.1040935000
_diffrn_orient_matrix_UB_23      -0.0205792000
_diffrn_orient_matrix_UB_31      0.1441071000
_diffrn_orient_matrix_UB_32      -0.0707207000
_diffrn_orient_matrix_UB_33      0.0347317000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9920
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.660
_diffrn_reflns_theta_min         4.165
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.262
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.527
_exptl_crystal_size_min          0.452
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.0729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                3470
_reflns_number_total             3600
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {6a5ea382-5a94-49f6-95d7-da39248d52da}
_cod_data_source_file            rm5017sup1.cif
_cod_data_source_block           form_II
_cod_database_code               2108512
_cod_database_fobs_code          2108512
_chemical_oxdiff_formula         'C21 H23 N1 O4'
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.674
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C17(H17), C8(H8), C21(H21), C20(H20), C10(H10), C6(H6),
 C9(H9), C5(H5)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              78433
_shelx_hkl_checksum              15162
_olex2_date_sample_data_collection 2018-06-13
_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 2.826
_oxdiff_exptl_absorpt_empirical_full_min 0.566