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_1553153
_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         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4972(2)
_cell_length_b                   14.1613(2)
_cell_length_c                   17.5538(3)
_cell_measurement_reflns_used    9208
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2860
_cell_measurement_theta_min      3.9910
_cell_volume                     3106.61(8)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   25.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000 -120.0000 63

  2 omega -122.00  -94.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 28

  3 omega  -81.00  -10.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  125.0000  -30.0000 71

  4 omega -119.00  -86.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   30.0000 33

  5 omega   98.00  145.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  119.0000 -166.0000 47

  6 omega   26.00  109.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -90.0000 83

  7 omega   61.00   87.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  150.0000 26

  8 omega   42.00   83.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   30.0000 41

  9 omega   44.00  100.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 56

 10 omega  106.00  172.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  -60.0000 66

 11 omega   45.00   71.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 26

 12 omega   38.00   98.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 60

 13 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.0607  -57.0000   60.0000 97

 14 omega -117.00  -92.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -77.0000  -90.0000 25

 15 omega   61.00  178.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000 -180.0000 117
;
_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      0.0362913000
_diffrn_orient_matrix_UB_12      0.0938024000
_diffrn_orient_matrix_UB_13      0.0363134000
_diffrn_orient_matrix_UB_21      0.0853571000
_diffrn_orient_matrix_UB_22      -0.0534065000
_diffrn_orient_matrix_UB_23      0.0464629000
_diffrn_orient_matrix_UB_31      0.0810496000
_diffrn_orient_matrix_UB_32      0.0143286000
_diffrn_orient_matrix_UB_33      -0.0649829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15485
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_min         5.039
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.882
_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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3033
_exptl_crystal_size_mid          0.1817
_exptl_crystal_size_min          0.1602
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0430P)^2^+1.2120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2826
_reflns_number_total             3132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00183h2.cif
_cod_data_source_block           6d-trans
_cod_original_cell_volume        3106.62(9)
_cod_database_code               1553153
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C19H21NO2
_reflns_odcompleteness_completeness 99.78
_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)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              91659
_olex2_submission_special_instructions 'No special instructions were received'