Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines.
Perryman, Michael S.; Earl, Matthew W. M.; Greatorex, Sam; Clarkson, Guy J.; Fox, David J.; Organic & biomolecular chemistry 13 (2015) 2360–2365; doi:10.1039/c4ob02311k

data_7154254
_publ_section_title
;
 Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type
 reactions with N-substituted diamines.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2360
_journal_page_last               2365
_journal_paper_doi               10.1039/c4ob02311k
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-08-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2014-09-02 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2888(2)
_cell_length_b                   6.04300(10)
_cell_length_c                   27.8317(6)
_cell_measurement_reflns_used    4995
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.3558
_cell_measurement_theta_min      3.1731
_cell_volume                     1562.26(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9948
_diffrn_measurement_details
;
  1 omega -115.00  -78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7051 -141.0000  178.0000 37

  2 omega  -61.00   -7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7051   57.0000  -90.0000 54

  3 omega -126.00  -97.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000 -150.0000 29

  4 omega  -43.00    3.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000   30.0000 -150.0000 46

  5 omega -114.00  -80.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000  -90.0000 34

  6 omega -126.00  -79.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5000 -111.0000    0.0000 47

  7 omega  113.00  176.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000    0.0000 -150.0000 63

  8 omega   26.00   51.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000    0.0000 -150.0000 25

  9 omega   36.00   62.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -150.0000 26

 10 omega   42.00   93.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 51

 11 omega   42.00   91.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  150.0000 49

 12 omega   57.00   95.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000    0.0000 -150.0000 38

 13 omega   39.00   87.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  150.0000 48

 14 omega   48.00   90.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -150.0000 42

 15 omega   52.00   77.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -60.0000 25

 16 omega   47.00   90.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -90.0000 43

 17 omega  119.00  144.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -150.0000 25

 18 omega   37.00  112.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000 -150.0000 75

 19 omega   66.00  139.00   1.0000  128.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -30.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0938253000
_diffrn_orient_matrix_UB_12      0.0488481000
_diffrn_orient_matrix_UB_13      0.0488354000
_diffrn_orient_matrix_UB_21      0.1603572000
_diffrn_orient_matrix_UB_22      -0.1029469000
_diffrn_orient_matrix_UB_23      0.0259850000
_diffrn_orient_matrix_UB_31      0.1746960000
_diffrn_orient_matrix_UB_32      0.1203628000
_diffrn_orient_matrix_UB_33      0.0023671000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            7248
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.561
_diffrn_reflns_theta_min         3.176
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).

Flack parameter (From Shelx 2013/4)
Flack x =   0.203(298) by hole-in-one fit to all intensities
            0.015(132) from 1357 selected quotients (Parsons' method)

Hooft y parameter (From Olex2)          0.07(12)

;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0465P)^2^+0.2270P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                3023
_reflns_number_total             3120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02311k2.cif
_cod_data_source_block           mp5
_cod_depositor_comments
'Adding full bibliography for 7154254--7154256.cif.'
_cod_database_code               7154254
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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 N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelxl_version_number           2013-2