Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones
Marichev, Kostiantyn O.; Garcia, Estevan C.; BHOWMICK, KARTICK CHANDRA; Wherritt, Daniel J.; Arman, Hadi; Doyle, Michael P.; Chem. Sci.  (2017) –; doi:10.1039/C7SC03184J

data_1546918
_publ_section_title
;
 Highly selective acylation of polyamines and aminoglycosides by
 5-acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03184J
_journal_year                    2017
_chemical_formula_moiety         'C27 H22 N2 O2'
_chemical_formula_sum            'C27 H22 N2 O2'
_chemical_formula_weight         406.48
_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     direct
_audit_creation_date             2016-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-07-20 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                69.385(6)
_cell_angle_beta                 82.282(6)
_cell_angle_gamma                87.431(7)
_cell_formula_units_Z            2
_cell_length_a                   5.7431(13)
_cell_length_b                   12.655(3)
_cell_length_c                   15.118(4)
_cell_measurement_reflns_used    5088
_cell_measurement_temperature    98
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.2
_cell_volume                     1019.1(4)
_computing_cell_refinement
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_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      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 246
               Slice: -68.0000 - 55.0000
         Image width: 0.5000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 270.0000
                 XTD: 35.0000
              2theta: -35.0000
scan:
    Number of images: 210
               Slice: -125.0000 - -20.0000
         Image width: 0.5000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 270.0000
                 XTD: 35.0000
              2theta: -35.0000
scan:
    Number of images: 102
               Slice: -55.0000 - -4.0000
         Image width: 0.5000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 0.0000
                 XTD: 35.0000
              2theta: -35.0000
scan:
    Number of images: 98
               Slice: -51.0000 - -2.0000
         Image width: 0.5000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 90.0000
                 XTD: 35.0000
              2theta: -35.0000
scan:
    Number of images: 70
               Slice: -115.0000 - -80.0000
         Image width: 0.5000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 180.0000
                 XTD: 35.0000
              2theta: -35.0000
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.170466
_diffrn_orient_matrix_UB_12      -0.039953
_diffrn_orient_matrix_UB_13      0.010567
_diffrn_orient_matrix_UB_21      -0.018015
_diffrn_orient_matrix_UB_22      0.080945
_diffrn_orient_matrix_UB_23      0.007739
_diffrn_orient_matrix_UB_31      0.008381
_diffrn_orient_matrix_UB_32      -0.016981
_diffrn_orient_matrix_UB_33      -0.068271
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6632
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         3.232
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0100P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2697
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03184j2.cif
_cod_data_source_block           cd1436a
_cod_database_code               1546918
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C21(H21), C20(H20), C11(H11), C14(H14), C17(H17), C18(H18),
 C13(H13), C12(H12), C8(H8), C27(H27), C23(H23), C24(H24), C26(H26), C25(H25)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method glassfiber
_olex2_submission_special_instructions 'No special instructions were received'