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_7226426
_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         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.32
_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   mixed
_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                 110.402(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2973(3)
_cell_length_b                   9.6961(3)
_cell_length_c                   17.2808(6)
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8700
_cell_measurement_theta_min      5.0600
_cell_volume                     1460.10(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_environment      N~2~
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -42.00   27.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  150.0000 69

  2 omega   73.00   99.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000   90.0000 26

  3 omega   96.00  122.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 26

  4 omega  138.00  166.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 28

  5 omega  153.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 25

  6 omega  140.00  171.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 31

  7 omega  114.00  141.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   30.0000 27

  8 omega   95.00  144.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 49

  9 omega   86.00  111.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 25

 10 omega   89.00  123.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 34

 11 omega   64.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 27

 12 omega   70.00  108.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -30.0000 38

 13 omega  100.00  138.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 38

 14 omega  123.00  149.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -180.0000 26

 15 omega  140.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 38

 16 omega  101.00  127.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 26

 17 omega   44.00   87.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -74.0000  -45.0000 43

 18 omega   39.00  117.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 78

 19 omega   81.00  108.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 27

 20 omega   42.00   97.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 55

 21 omega   32.00   60.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 28

 22 omega   39.00   83.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 44

 23 omega   50.00   82.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 32

 24 omega   38.00  103.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 65

 25 omega   62.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  -90.0000 25

 26 omega -120.00  -12.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -19.0000  -30.0000 108

 27 omega -111.00  -86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000 -120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0931199000
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_diffrn_orient_matrix_UB_21      0.1226393000
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_diffrn_orient_matrix_UB_23      -0.0456765000
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_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9351
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.975
_diffrn_reflns_theta_min         5.075
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.744
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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
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_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.546
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.4229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2553
_reflns_number_total             2995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra19196g2.cif
_cod_data_source_block           uny076
_cod_database_code               7226426
_chemical_oxdiff_formula         'C18 H17 N O3'
_reflns_odcompleteness_completeness 95.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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 O(H) groups
2.a Riding coordinates:
 O3(H3)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'