The first solvent-free synthesis of privileged gamma- and delta-lactams via the Castagnoli-Cushman reaction
Lepikhina, Anastasia; Bakulina, Olga; Dar'in, Dmitry; Krasavin, Mikhail; RSC Adv.  (2016) –; doi:10.1039/C6RA19196G

data_7226427
_publ_section_title
;
 The first solvent-free synthesis of privileged gamma- and delta-lactams
 via the Castagnoli-Cushman reaction
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA19196G
_journal_year                    2016
_chemical_formula_moiety         'C19 H18 Cl N O3'
_chemical_formula_sum            'C19 H18 Cl N O3'
_chemical_formula_weight         343.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-25 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8247(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.15491(19)
_cell_length_b                   11.7971(2)
_cell_length_c                   14.1333(3)
_cell_measurement_reflns_used    11818
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1698
_cell_measurement_theta_min      2.6555
_cell_volume                     1677.38(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -35.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -57.0000   90.0000 79

  2 omega   13.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -99.0000 -150.0000 56

  3 omega   35.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -99.0000  -30.0000 26

  4 omega   -7.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -99.0000   60.0000 76

  5 omega   11.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  -30.0000 83

  6 omega  -46.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -19.0000  150.0000 113

  7 omega  -91.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.5593  178.0000 -150.0000 59

  8 omega    6.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  120.0000 89

  9 omega   35.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  178.0000   90.0000 29

 10 omega    6.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000   60.0000 54

 11 omega    7.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000 -150.0000 88

 12 omega    2.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   77.0000 -120.0000 93

 13 omega  -35.00   -4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  131.0000    5.3825 31
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0378095000
_diffrn_orient_matrix_UB_12      0.0501214000
_diffrn_orient_matrix_UB_13      0.0030006000
_diffrn_orient_matrix_UB_21      -0.0459492000
_diffrn_orient_matrix_UB_22      -0.0306202000
_diffrn_orient_matrix_UB_23      0.0236913000
_diffrn_orient_matrix_UB_31      0.0378050000
_diffrn_orient_matrix_UB_32      0.0128714000
_diffrn_orient_matrix_UB_33      0.0446795000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0391P)^2^+0.8740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             3845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra19196g2.cif
_cod_data_source_block           uny098
_cod_original_cell_volume        1677.37(5)
_cod_database_code               7226427
_chemical_oxdiff_formula         'C18 H17 N O3'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'