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_2108513
_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
_chemical_name_systematic
'Polymorph of Agometaline-hydroquinone (1:1) cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.33300(10)
_cell_length_b                   29.3095(4)
_cell_length_c                   8.80460(10)
_cell_measurement_reflns_used    12027
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2650
_cell_measurement_theta_min      3.0140
_cell_volume                     1885.85(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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   -126.00-101.00   1.00    4.11    --  -37.50 -99.00 -90.00   25
  2  \w     28.00  79.00   1.00    4.11    --   37.50-125.00 120.00   51
  3  \w     87.00 120.00   1.00    4.11    --   37.50  57.00-180.00   33
  4  \w     30.00  57.00   1.00    4.11    --   37.50  38.00-120.00   27
  5  \w     18.00 129.00   1.00    4.11    --   37.50  77.00 -60.00  111
  6  \w      4.00  80.00   1.00    4.11    --   37.50 -99.00 -30.00   76
  7  \w      1.00  54.00   1.00    4.11    --   37.50  77.00   0.00   53
  8  \w     56.00  81.00   1.00    4.11    --   37.50 -99.00-150.00   25
  9  \w     12.00 129.00   1.00    4.11    --   37.50  77.00 120.00  117
 10  \w     81.00 121.00   1.00    4.11    --   37.50  38.00-120.00   40
 11  \w      5.00  57.00   1.00    4.11    --   37.50 -99.00-120.00   52
 12  \w     -1.00 129.00   1.00    4.11    --   37.50  77.00  60.00  130
 13  \w     34.00  61.00   1.00    4.11    --   37.50  57.00-180.00   27
 14  \w     35.00  61.00   1.00    4.11    --   37.50-143.00  62.00   26
 15  \w      4.00  42.00   1.00    4.11    --   37.50 -99.00-150.00   38
 16  \w     57.00 122.00   1.00    4.11    --   37.50  77.00   0.00   65
 17  \w     84.00 128.00   1.00    4.11    --   37.50  77.00-120.00   44
 18  \w     12.00  73.00   1.00    4.11    --   37.50 -99.00 120.00   61
 19  \w     -2.00  70.00   1.00    4.11    --   37.50  77.00-120.00   72
 20  \w      0.00  26.00   1.00    4.11    --   37.50  38.00-120.00   26
 21  \w     73.00 114.00   1.00    5.00    --  109.79  61.00-150.00   41
 22  \w     73.00 101.00   1.00    5.00    --  109.79  61.00 150.00   28
 23  \w     73.00 166.00   1.00    5.00    --  109.79  61.00 120.00   93
 24  \w     71.00 176.00   1.00    5.00    --  109.79  77.00 150.00  105
 25  \w     70.00  96.00   1.00    5.00    --  109.79  77.00-150.00   26
 26  \w     70.00 176.00   1.00    5.00    --  109.79  77.00 -90.00  106
 27  \w     70.00  96.00   1.00    5.00    --  109.79  77.00-180.00   26
 28  \w    119.00 177.00   1.00    5.00    --  109.79  77.00-180.00   58
 29  \w     73.00 137.00   1.00    5.00    --  109.79  61.00  90.00   64
 30  \w     73.00  99.00   1.00    5.00    --  109.79  61.00 -90.00   26
 31  \w     74.00 108.00   1.00    5.00    --  109.79  61.00 -30.00   34
 32  \w     49.00 105.00   1.00    5.00    --  109.79-111.00 150.00   56
 33  \w     26.00 112.00   1.00    5.00    --  109.79-111.00 -30.00   86
 34  \w    106.00 141.00   1.00    5.00    --  109.79  77.00  60.00   35
 35  \w     73.00  99.00   1.00    5.00    --  109.79  61.00-180.00   26
 36  \w     70.00 166.00   1.00    5.00    --  109.79  77.00-120.00   96
 37  \w     70.00 100.00   1.00    5.00    --  109.79  77.00  60.00   30
 38  \w     70.00  96.00   1.00    5.00    --  109.79  77.00 -60.00   26
 39  \w     70.00 135.00   1.00    5.00    --  109.79  77.00  90.00   65
 40  \w    111.00 163.00   1.00    5.00    --  109.79  77.00 -30.00   52
 41  \w     59.00  93.00   1.00    5.00    --  109.79-127.00-128.00   34
 42  \w    111.00 171.00   1.00    5.00    --  109.79  77.00 -60.00   60
 43  \w     70.00  96.00   1.00    5.00    --  109.79  77.00 -30.00   26
 44  \w     73.00 105.00   1.00    5.00    --  109.79  61.00   0.00   32
 45  \w     70.00 157.00   1.00    5.00    --  109.79  77.00   0.00   87
 46  \w     73.00  99.00   1.00    5.00    --  109.79  61.00  60.00   26
 47  \w     75.00 101.00   1.00    5.00    --  109.79  61.00 -60.00   26
 48  \w     73.00  99.00   1.00    5.00    --  109.79  61.00  30.00   26
 49  \w     70.00  96.00   1.00    5.00    --  109.79  77.00 120.00   26
 50  \w    124.00 167.00   1.00    5.00    --  109.79  61.00-150.00   43
 51  \w     73.00 110.00   1.00    5.00    --  109.79  61.00-120.00   37
 52  \w     70.00 178.00   1.00    5.00    --  109.79  77.00  30.00  108
 53  \w     21.00 142.00   1.00    5.00    --  109.79 -77.00 -30.00  121
 54  \w     37.00  94.00   1.00    5.00    --  109.79 -94.00-120.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0159061000
_diffrn_orient_matrix_UB_12      -0.0004621000
_diffrn_orient_matrix_UB_13      -0.1733711000
_diffrn_orient_matrix_UB_21      0.0123026000
_diffrn_orient_matrix_UB_22      -0.0524678000
_diffrn_orient_matrix_UB_23      0.0031686000
_diffrn_orient_matrix_UB_31      -0.2098484000
_diffrn_orient_matrix_UB_32      -0.0031025000
_diffrn_orient_matrix_UB_33      -0.0275315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20956
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.768
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'Solvent evaporation'
_exptl_crystal_recrystallization_method 'Crystallization from methanol'
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         7276
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0818P)^2^+0.0942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                6726
_reflns_number_total             7276
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {9d3af4f5-2891-4fd7-8770-d415c5bcce1a}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            rm5017sup1.cif
_cod_data_source_block           form_III
_cod_database_code               2108513
_cod_database_fobs_code          2108513
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H23 N O4'
_reflns_odcompleteness_completeness 99.91
_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), C27(H27a,H27b), C12(H12a,H12b), C26(H26a,H26b)
2.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C38(H38), C33(H33), C39(H39), C36(H36), C42(H42), C32(H32),
 C35(H35), C3(H3), C18(H18), C5(H5), C8(H8), C6(H6), C9(H9), C10(H10), C24(H24),
  C25(H25), C20(H20), C21(H21), C23(H23)
2.c Idealised Me refined as rotating group:
 C29(H29a,H29b,H29c), C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C30(H30a,H30b,
 H30c)
;
_shelx_res_checksum              71989
_shelx_hkl_checksum              29103
_olex2_exptl_crystal_mounting_method 'Glass fibre'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.747
_oxdiff_exptl_absorpt_empirical_full_min 0.612
_publcif_funding_html
;
;