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_1553160
_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         'C34 H34 N2 O'
_chemical_formula_sum            'C34 H34 N2 O'
_chemical_formula_weight         486.63
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-01
_audit_creation_method
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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                90
_cell_angle_beta                 104.8514(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9986(2)
_cell_length_b                   10.60180(16)
_cell_length_c                   20.9045(4)
_cell_measurement_reflns_used    7780
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2370
_cell_measurement_theta_min      3.7770
_cell_volume                     2570.36(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
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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_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -40.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000  -90.0000 69

  2 omega  -45.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000  120.0000 44

  3 omega   32.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857 -125.0000   30.0000 56

  4 omega   26.00  105.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 79

  5 omega   72.00  119.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  120.0000 47

  6 omega   48.00   97.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 49

  7 omega   61.00  172.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257   15.0000   90.0000 111

  8 omega   92.00  178.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  150.0000 86

  9 omega   93.00  134.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -77.0000  -90.0000 41

 10 omega   67.00  109.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -90.0000 42

 11 omega   55.00  108.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 53

 12 omega   57.00   89.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -150.0000 32

 13 omega   35.00   98.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000 -180.0000 63

 14 omega   37.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857 -125.0000 -180.0000 50

 15 omega   38.00   97.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -90.0000 59

 16 omega   35.00   91.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000    0.0000 56

 17 omega   52.00   84.00   1.0000    1.9350
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000  120.0000 32

 18 omega -129.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857    0.0000  -90.0000 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      0.0258841000
_diffrn_orient_matrix_UB_12      -0.0105824000
_diffrn_orient_matrix_UB_13      0.0759281000
_diffrn_orient_matrix_UB_21      -0.0099896000
_diffrn_orient_matrix_UB_22      -0.1446678000
_diffrn_orient_matrix_UB_23      -0.0058804000
_diffrn_orient_matrix_UB_31      0.1297850000
_diffrn_orient_matrix_UB_32      -0.0089099000
_diffrn_orient_matrix_UB_33      0.0043158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.419
_diffrn_reflns_theta_min         3.811
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.961
_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    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3228
_exptl_crystal_size_mid          0.2557
_exptl_crystal_size_min          0.1293
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0579P)^2^+0.8834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4414
_reflns_number_total             5186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00183h2.cif
_cod_data_source_block           11c
_cod_original_cell_volume        2570.37(8)
_cod_database_code               1553160
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C34H34N2O
_reflns_odcompleteness_completeness 99.98
_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:
 C4(H4A,H4B), 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)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              77314
_olex2_submission_special_instructions 'No special instructions were received'