Pharmaceutical solvate formation for the incorporation of the antimicrobial agent hydrogen peroxide.
Kersten, Kortney M.; Breen, Meghan E.; Mapp, Anna K.; Matzger, Adam J.; Chemical communications (Cambridge, England) 54 (2018) 9286–9289; doi:10.1039/c8cc04530e

data_7122044
_publ_section_title
;
 Pharmaceutical solvate formation for the incorporation of the
 antimicrobial agent hydrogen peroxide.
;
_journal_issue                   67
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9286
_journal_page_last               9289
_journal_paper_doi               10.1039/c8cc04530e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         '2(C18 H14 Cl4 N2 O), H2 O2'
_chemical_formula_sum            'C36 H30 Cl8 N4 O4'
_chemical_formula_weight         866.24
_chemical_name_common            'Miconazole hemi-(hydrogen peroxide) solvate'
_chemical_name_systematic
'1-?[2-?(2,?4-?dichlorophenyl)?-?2-?[(2,?4-?dichlorophenyl)?methoxy]?ethyl]?-1H-?Imidazole hemi-(hydrogen peroxide) solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2018-06-05 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                75.9580(18)
_cell_angle_beta                 85.8331(17)
_cell_angle_gamma                87.3903(16)
_cell_formula_units_Z            2
_cell_length_a                   7.94286(15)
_cell_length_b                   14.5267(3)
_cell_length_c                   16.8597(4)
_cell_measurement_reflns_used    13233
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8920
_cell_measurement_theta_min      3.1400
_cell_volume                     1881.43(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.5a (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -109.00 -84.00   0.50    0.23    --  -47.82-134.00  99.00   50
  2  \w   -116.00 -26.00   0.50    0.23    --  -47.82 -77.00 120.00  180
  3  \w     31.00  93.00   0.50    0.23    --   47.82-134.00  99.00  124
  4  \w     73.00 120.00   0.50    0.92    --  107.75-134.00  99.00   94
  5  \w     82.00 108.00   0.50    0.92    --  107.75 -57.00  60.00   52
  6  \w    100.00 125.00   0.50    0.92    --  107.75 -77.00   0.00   50
  7  \w     76.00 120.00   0.50    0.92    --  107.75-135.00 -79.00   88
  8  \w     93.00 131.00   0.50    0.92    --  107.75 -77.00-120.00   76
  9  \w     66.00 118.00   0.50    0.92    --  107.75-125.00-150.00  104
 10  \w     64.00 108.00   0.50    0.92    --  107.75 -99.00-120.00   88
 11  \w     50.00 102.00   0.50    0.92    --  107.75 -57.00-120.00  104
 12  \w     34.00  59.00   0.50    0.23    --   47.82-135.00 -79.00   50
 13  \w     35.00  77.00   0.50    0.92    --  107.75 -77.00-120.00   84
 14  \w     36.00  68.00   0.50    0.92    --  107.75 -37.00 -30.00   64
 15  \w     37.00  68.00   0.50    0.92    --  107.75 -37.00  30.00   62
 16  \w     39.00  69.00   0.50    0.92    --  107.75 -37.00  90.00   60
 17  \w     44.00  69.00   0.50    0.92    --  107.75 -57.00  60.00   50
 18  \w     38.00  63.00   0.50    0.92    --  107.75 -19.00  30.00   50
 19  \w     41.00  67.00   0.50    0.92    --  107.75 -37.00  60.00   52
 20  \w     36.00  68.00   0.50    0.92    --  107.75 -37.00 120.00   64
 21  \w     57.00 103.00   0.50    0.92    --  107.75 -77.00 150.00   92
 22  \w     60.00 105.00   0.50    0.92    --  107.75 -99.00 120.00   90
 23  \w     42.00  67.00   0.50    0.92    --  107.75 -77.00   0.00   50
 24  \w     82.00 108.00   0.50    0.92    --  107.75 -99.00   0.00   52
 25  \w     37.00  69.00   0.50    0.92    --  107.75 -37.00 -60.00   64
 26  \w     37.00  76.00   0.50    0.92    --  107.75 -19.00 -90.00   78
 27  \w     35.00  69.00   0.50    0.92    --  107.75 -37.00-120.00   68
 28  \w     36.00  67.00   0.50    0.92    --  107.75 -37.00-150.00   62
 29  \w     35.00  68.00   0.50    0.92    --  107.75 -37.00 -90.00   66
 30  \w     36.00  68.00   0.50    0.92    --  107.75 -37.00   0.00   64
 31  \w     33.00  65.00   0.50    0.92    --  107.75 -19.00  60.00   64
 32  \w     37.00  75.00   0.50    0.92    --  107.75 -19.00 120.00   76
 33  \w     40.00  68.00   0.50    0.92    --  107.75 -37.00 150.00   56
 34  \w     32.00  69.00   0.50    0.92    --  107.75 -19.00   0.00   74
 35  \w     38.00 118.00   0.50    0.23    --   47.82  37.00 -90.00  160
 36  \w     74.00 110.00   0.50    0.23    --   47.82 125.00 -30.00   72
 37  \w     68.00  93.00   0.50    0.23    --   47.82 135.00 -13.00   50
 38  \w    113.00 138.00   0.50    0.92    --  107.75 135.00 -13.00   50
 39  \w     68.00  93.00   0.50    0.23    --   47.82 134.00 167.00   50
 40  \w     67.00 109.00   0.50    0.92    --  107.75 134.00 167.00   84
 41  \w    -25.00  59.00   0.50    0.23    --   47.82 -37.00 120.00  168
 42  \w    -58.00 -33.00   0.50    0.23    --  -47.82 135.00 -13.00   50
 43  \w   -107.00 -21.00   0.50    0.92    --  -84.50 135.00 -13.00  172
 44  \w    -82.00 -57.00   0.50    0.23    --  -47.82 134.00 167.00   50
 45  \w    -63.00 -20.00   0.50    0.92    --  -84.50 134.00 167.00   86
 46  \w   -139.00 -97.00   0.50    0.92    --  -84.50 -57.00 150.00   84
 47  \w   -135.00-110.00   0.50    0.92    --  -84.50-134.00  99.00   50
 48  \w   -116.00 -91.00   0.50    0.23    --  -47.82-135.00 -79.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1459393000
_diffrn_orient_matrix_UB_12      -0.0035885000
_diffrn_orient_matrix_UB_13      -0.0646622000
_diffrn_orient_matrix_UB_21      0.1198246000
_diffrn_orient_matrix_UB_22      -0.0404428000
_diffrn_orient_matrix_UB_23      0.0687467000
_diffrn_orient_matrix_UB_31      -0.0468375000
_diffrn_orient_matrix_UB_32      -0.1015467000
_diffrn_orient_matrix_UB_33      -0.0006784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22282
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         2.707
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.5a (Rigaku Oxford Diffraction, 2018)
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    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_recrystallization_method 'crystallized from EtOH/H2O2'
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.00035(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0552
_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^)+21.5793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6068
_reflns_number_total             6643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04530e2.cif
_cod_data_source_block           kmkh2o2
_cod_depositor_comments          'Adding full bibliography for 7122044.cif.'
_cod_original_cell_volume        1881.42(7)
_cod_database_code               7122044
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H10 N O'
_diffrn_oxdiff_ac3_digest_frames
;
01706b4a34e561650c25c1bd9c79b099320367880c9
;
_diffrn_oxdiff_ac3_digest_hkl
;
01a76d776e7389557c3d8ecdae10553491587d
;
_reflns_odcompleteness_completeness 99.84
_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
2.a Ternary CH refined with riding coordinates:
 C32(H32), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C10(H10A,H10B), C35(H35A,H35B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C21(H21), C31(H31), C30(H30), C5(H5), C37(H37), C3(H3), C15(H15),
 C28(H28), C45(H45), C19(H19), C2(H2), C16(H16), C43(H43), C46(H46), C38(H38),
 C40(H40), C13(H13)
;
_olex2_exptl_crystal_mounting_method MiTeGen
_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 1.605
_oxdiff_exptl_absorpt_empirical_full_min 0.636