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_1553158
_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         'C46 H42 N2 O'
_chemical_formula_sum            'C46 H42 N2 O'
_chemical_formula_weight         638.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-07
_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                 105.8657(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.55604(14)
_cell_length_b                   15.09459(13)
_cell_length_c                   18.96430(17)
_cell_measurement_reflns_used    19536
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      74.1280
_cell_measurement_theta_min      4.6540
_cell_volume                     3457.35(6)
_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      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -74.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   77.0000  120.0000 105

  2 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000    0.0000 80

  3 omega -113.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607 -139.0000 -113.0000 49

  4 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  120.0000 105

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

  6 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000  -90.0000 75

  7 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.5607 -125.0000  -30.0000 75

  8 omega   25.00  109.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 84

  9 omega   35.00  122.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  -90.0000 87

 10 omega   32.00   91.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   60.0000 59

 11 omega   83.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000    0.0000 95

 12 omega   25.00  109.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -60.0000 84

 13 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000 -150.0000 64

 14 omega   61.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000   90.0000 117

 15 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -60.0000 64

 16 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  120.0000 64

 17 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 64

 18 omega   35.00   99.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   30.0000 64

 19 omega   35.00  122.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000   90.0000 87

 20 omega   36.00  134.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -61.0000 -150.0000 98

 21 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  -90.0000 105

 22 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000 -180.0000 105

 23 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -57.0000 -150.0000 97

 24 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607   38.0000  -90.0000 80

 25 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5607  -77.0000  -30.0000 105

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

 27 omega   61.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000 -120.0000 117

 28 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   30.0000 103

 29 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 103

 30 omega   79.00  177.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   90.0000 98

 31 omega   79.00  177.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -120.0000 98

 32 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -90.0000 103

 33 omega   79.00  127.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -150.0000 48

 34 omega   75.00  178.00   1.0000    2.3100
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 103
;
_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      0.0393431000
_diffrn_orient_matrix_UB_12      -0.0944538000
_diffrn_orient_matrix_UB_13      -0.0108436000
_diffrn_orient_matrix_UB_21      0.0372694000
_diffrn_orient_matrix_UB_22      -0.0131864000
_diffrn_orient_matrix_UB_23      0.0837390000
_diffrn_orient_matrix_UB_31      -0.1154170000
_diffrn_orient_matrix_UB_32      -0.0363900000
_diffrn_orient_matrix_UB_33      -0.0021494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.331
_diffrn_reflns_theta_min         4.689
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.901
_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    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2615
_exptl_crystal_size_mid          0.1421
_exptl_crystal_size_min          0.0885
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0440P)^2^+2.7440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3248
_reflns_number_total             3515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00183h2.cif
_cod_data_source_block           11a
_cod_database_code               1553158
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C23 H21 N O2'
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), 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:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              50115
_olex2_submission_special_instructions 'No special instructions were received'