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_1553159
_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         'C48 H46 N2 O3'
_chemical_formula_sum            'C48 H46 N2 O3'
_chemical_formula_weight         698.87
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                99.778(2)
_cell_angle_beta                 99.679(2)
_cell_angle_gamma                106.888(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1705(3)
_cell_length_b                   10.2903(3)
_cell_length_c                   19.4528(5)
_cell_measurement_reflns_used    16193
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      74.1680
_cell_measurement_theta_min      4.5710
_cell_volume                     1868.04(10)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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      99.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega   23.00   82.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       42.8107   38.0000  -30.0000 59

  2 omega   97.00  124.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  -78.4862 27

  3 omega  100.00  126.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -143.9027 26

  4 omega  108.00  176.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -150.0000 68

  5 omega  144.00  170.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 26

  6 omega  111.00  177.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 66

  7 omega  134.00  160.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   63.0000  -23.6666 26

  8 omega  122.00  149.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       94.0000   69.0000   21.8378 27

  9 omega   76.00  166.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 90

 10 omega   75.00  101.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   30.0000 26

 11 omega   79.00  177.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000    0.0000 98

 12 omega   79.00  105.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   63.0000  -23.6666 26

 13 omega   75.00  157.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -90.0000 82

 14 omega   81.00  169.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 88

 15 omega   79.00  175.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   60.0000 96

 16 omega   76.00  152.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   90.0000 76

 17 omega   75.00  101.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 26

 18 omega   75.00  101.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -120.0000 26

 19 omega   75.00  102.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -150.0000 27

 20 omega   75.00  129.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 54

 21 omega   52.00   79.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   72.0000 -175.3215 27

 22 omega   51.00   77.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   77.0000 -146.5494 26

 23 omega   36.00   63.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -143.9027 27

 24 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -114.2179 25

 25 omega   45.00   72.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       74.0000   68.0000  -74.0308 27

 26 omega   43.00   70.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -31.9960 27

 27 omega   65.00   92.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       94.0000   69.0000   21.8378 27

 28 omega   59.00   88.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       90.0000   74.0000   75.6551 29

 29 omega   53.00   79.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   67.0000  156.4616 26

 30 omega   67.00  164.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       94.0000   63.0000  168.4610 97

 31 omega   52.00   77.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -       82.0000   76.0000  113.0487 25

 32 omega   45.00   70.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       74.0000   70.0000   71.5699 25

 33 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000   51.9120 25

 34 omega   40.00   65.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000    7.6433 25

 35 omega   32.00   58.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000    7.3912 26

 36 omega   35.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -42.3615 26

 37 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  -78.4862 25

 38 omega   17.00   43.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000 -164.7459 26

 39 omega    8.00   33.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       42.0000   85.0000  -42.6889 25

 40 omega   18.00   43.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000   54.3015 25

 41 omega   13.00   38.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       46.0000   83.0000   21.1604 25

 42 omega   18.00   43.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  119.2219 25

 43 omega   31.00   57.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  120.2191 26

 44 omega   36.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  137.3951 25

 45 omega   35.00   61.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  174.1956 26

 46 omega   33.00  137.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000    0.0000 104

 47 omega   51.00  122.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000 -180.0000 71

 48 omega   36.00   83.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 47

 49 omega   34.00  111.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000  -60.0000 77

 50 omega   28.00  112.00   1.0000   12.8550
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -102.0000  -89.0000 84

 51 omega   23.00   98.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -       42.8107 -125.0000 -180.0000 75

 52 omega  -68.00   25.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107   57.0000    0.0000 93

 53 omega -114.00  -22.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -38.0000  -60.0000 92

 54 omega -113.00  -16.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107  -57.0000 -150.0000 97

 55 omega -114.00   24.00   1.0000    3.2150
omega____ theta____ kappa____ phi______ frames
    -      -42.8107    0.0000  -30.0000 138
;
_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      0.1310477000
_diffrn_orient_matrix_UB_12      0.0488299000
_diffrn_orient_matrix_UB_13      0.0627250000
_diffrn_orient_matrix_UB_21      0.0787428000
_diffrn_orient_matrix_UB_22      -0.0688542000
_diffrn_orient_matrix_UB_23      -0.0480433000
_diffrn_orient_matrix_UB_31      0.0556377000
_diffrn_orient_matrix_UB_32      0.1368975000
_diffrn_orient_matrix_UB_33      -0.0240464000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31249
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.062
_diffrn_reflns_theta_min         7.122
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.982
_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    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.1859
_exptl_crystal_size_mid          0.1062
_exptl_crystal_size_min          0.0726
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0863
_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^)+(0.0460P)^2^+8.5290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2303
_refine_ls_wR_factor_ref         0.2339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6174
_reflns_number_total             7054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00183h2.cif
_cod_data_source_block           11b
_cod_original_cell_volume        1868.03(9)
_cod_database_code               1553159
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C48 H46 N2 O3'
_reflns_odcompleteness_completeness 99.79
_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:
 C2(H2), C5(H5), C19(H19), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C18(H18A,H18B), C21(H21A,H21B)
2.c 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), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39),
 C40(H40), C43(H43), C44(H44), C46(H46), C47(H47)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              2339
_olex2_submission_special_instructions 'No special instructions were received'