Facile access to <i>C</i>-substituted piperazin-2-ones and mianserin derivative enabled by chemoselective carbene insertion and cyclization cascade.
Kumar, Dharmendra; Unnikrishnan, Urmila; Kuram, Malleswara Rao; Chemical communications (Cambridge, England) 60 (2024) 5691–5694; doi:10.1039/d4cc00959b

data_7133005
_publ_section_title
;
 Facile access to <i>C</i>-substituted piperazin-2-ones and mianserin
 derivative enabled by chemoselective carbene insertion and cyclization
 cascade.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5691
_journal_page_last               5694
_journal_paper_doi               10.1039/d4cc00959b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C23 H22 N2 O'
_chemical_formula_sum            'C23 H22 N2 O'
_chemical_formula_weight         342.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-12-26 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0123(6)
_cell_length_b                   18.3467(8)
_cell_length_c                   10.1070(4)
_cell_measurement_reflns_used    3751
_cell_measurement_temperature    295.00(10)
_cell_measurement_theta_max      75.6450
_cell_measurement_theta_min      2.3920
_cell_volume                     1856.58(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.886
_diffrn_measured_fraction_theta_max 0.806
_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   -157.00 -90.00   0.50    0.17    --  -91.75 -44.00 -90.00  134
  2  \w   -142.00 -95.00   0.50    0.17    --  -91.75-111.00  46.00   94
  3  \w    -18.00  10.00   0.50    0.05    --  -47.33  19.00 150.00   56
  4  \w    -20.00  28.00   0.50    0.05    --  -47.33  19.00   0.00   96
  5  \w    -77.00 -17.00   0.50    0.05    --  -47.33 125.00-180.00  120
  6  \w   -162.00 -87.00   0.50    0.17    --  -91.75 -99.00-180.00  150
  7  \w    -77.00 -51.00   0.50    0.17    --  -91.75 111.00 140.00   52
  8  \w     38.00  64.00   0.50    0.17    --  109.61 -57.00 120.00   52
  9  \w     43.00  68.00   0.50    0.17    --  109.61 -57.00 -90.00   50
 10  \w     38.00  68.00   0.50    0.17    --  109.61 -57.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1298363000
_diffrn_orient_matrix_UB_12      -0.0446907000
_diffrn_orient_matrix_UB_13      -0.0097051000
_diffrn_orient_matrix_UB_21      -0.0251992000
_diffrn_orient_matrix_UB_22      0.0121625000
_diffrn_orient_matrix_UB_23      0.1487031000
_diffrn_orient_matrix_UB_31      -0.0785181000
_diffrn_orient_matrix_UB_32      0.0700952000
_diffrn_orient_matrix_UB_33      -0.0319403000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.886
_diffrn_reflns_Laue_measured_fraction_max 0.806
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5512
_diffrn_reflns_point_group_measured_fraction_full 1.759
_diffrn_reflns_point_group_measured_fraction_max 0.677
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.889
_diffrn_reflns_theta_min         2.408
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       0.0055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0489P)^2^+0.0522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.583
_reflns_Friedel_fraction_full    0.614
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                2384
_reflns_number_total             2664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00959b2.cif
_cod_data_source_block           xrf070623c_auto
_cod_depositor_comments          'Adding full bibliography for 7133005.cif.'
_cod_database_code               7133005
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.896
_reflns_odcompleteness_completeness 88.65
_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:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E), C00G(H00G,H00H), C00I(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00F),
 C00H(H00I), C00J(H00L), C00K(H00M), C00L(H00N), C00M(H00O), C00N(H00P),
 C00O(H00Q), C00P(H00R), C00Q(H00S)
;
_shelx_res_checksum              9439
_shelx_hkl_checksum              59837
_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 1.884
_oxdiff_exptl_absorpt_empirical_full_min 0.473