γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines
Hama Salih, Mariwan A.; Male, Louise; Spencer, Neil; Fossey, John S.; Organic Chemistry Frontiers 2 (2015) 1445–; doi:10.1039/C5QO00183H

data_1553156
_publ_section_title
;
 \g-Lactams and furan bispyrrolidines via iodine mediated cyclisation of
 homoallylamines
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1445
_journal_paper_doi               10.1039/C5QO00183H
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_weight         312.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-09
_audit_creation_method
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Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
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_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.798(4)
_cell_angle_beta                 101.156(4)
_cell_angle_gamma                100.035(4)
_cell_formula_units_Z            4
_cell_length_a                   6.8071(3)
_cell_length_b                   15.0202(7)
_cell_length_c                   15.8559(8)
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      74.2830
_cell_measurement_theta_min      4.2050
_cell_volume                     1564.30(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
  1 omega -112.00  -60.00   1.0000    3.6300
omega____ theta____ kappa____ phi______ frames
    -      -42.5607 -147.0000   70.0000 52

  2 omega -113.00  -16.00   1.0000    3.6300
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000  -30.0000 97

  3 omega   36.00   87.00   1.0000    3.6300
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000  -90.0000 51

  4 omega  -71.00   23.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   61.0000  120.0000 94

  5 omega  -20.00   28.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   45.0000  -90.0000 48

  6 omega   47.00   74.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 27

  7 omega   33.00   91.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  120.0000 58

  8 omega   27.00  150.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -15.0000 -120.0000 123

  9 omega   34.00   89.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   30.0000 55

 10 omega   76.00  109.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -60.0000 33

 11 omega   38.00  137.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000    0.0000 99

 12 omega   93.00  121.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  150.0000 28

 13 omega   83.00  171.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257   45.0000   60.0000 88

 14 omega  101.00  174.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000  -90.0000 73

 15 omega   41.00  120.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -61.0000 -120.0000 79

 16 omega   32.00   73.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -180.0000 41

 17 omega   45.00  107.00   1.0000   14.5200
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1916140000
_diffrn_orient_matrix_UB_12      -0.0372494000
_diffrn_orient_matrix_UB_13      -0.0101525000
_diffrn_orient_matrix_UB_21      0.0754684000
_diffrn_orient_matrix_UB_22      0.0088086000
_diffrn_orient_matrix_UB_23      0.0983398000
_diffrn_orient_matrix_UB_31      -0.1121989000
_diffrn_orient_matrix_UB_32      -0.0970083000
_diffrn_orient_matrix_UB_33      0.0075714000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11128
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.551
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2231
_exptl_crystal_size_mid          0.1164
_exptl_crystal_size_min          0.0297
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0520P)^2^+0.2941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4927
_reflns_number_total             6195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00183h2.cif
_cod_data_source_block           6p-cis
_cod_database_code               1553156
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C18 H20 N2 O3'
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C105(H105)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C101(H10A,H10B), C104(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C108(H108), C109(H109), C110(H110), C111(H111), C113(H113), C114(H114),
 C116(H116), C117(H117)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C18(H18A,H18B,H18C), C106(H10E,H10F,H10G), C118(H11A,H11B,
 H11C)
;
_shelx_res_checksum              45471
_olex2_submission_special_instructions 'No special instructions were received'