The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed intramolecular alder-ene reaction.
Petit, Laurent; Banwell, Martin G.; Willis, Anthony C.; Organic letters 13 (2011) 5800–5803; doi:10.1021/ol2023938

data_1502539
_publ_section_title
;
 The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed
 intramolecular alder-ene reaction.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5800
_journal_page_last               5803
_journal_paper_doi               10.1021/ol2023938
_journal_volume                  13
_journal_year                    2011
_chemical_compound_source        local
_chemical_formula_moiety         'C29 H36 N2 O7 S Si'
_chemical_formula_sum            'C29 H36 N2 O7 S Si'
_chemical_formula_weight         584.77
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-05-17
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2011-05-17 - Report on C29 H36 N2 O7 S Si
             by Anthony C. Willis
             for  Laurent Petit and Martin Banwell

2011-05-18 - passes most checkcif tests 
2011-09-15 - tweak cif
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0857(7)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   25.6392(3)
_cell_length_b                   14.1998(2)
_cell_length_c                   34.5075(5)
_cell_measurement_reflns_used    69636
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     12438.3(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            84433
_diffrn_reflns_theta_full        25.029
_diffrn_reflns_theta_max         25.029
_diffrn_reflns_theta_min         2.681
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4960
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.84
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9688
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         10996
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.0384005
_refine_ls_shift/su_mean         0.0017843
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 18.2 27.2 13.1 3.32 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1638
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1638
_reflns_limit_h_max              30
_reflns_limit_h_min              -30
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                7271
_reflns_number_total             10996
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.44
_oxford_diffrn_Wilson_scale      129.89
_oxford_refine_ls_r_factor_ref   0.0966
_oxford_refine_ls_scale          0.09796(3)
_oxford_reflns_number_all        10996
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '5131702 ban1109a'
_cod_data_source_file            ol2023938_si_002.cif
_cod_data_source_block           ban1109a
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               1502539
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE S(19,X'S,U'S) UNTIL S(119) 
CONT SI(34,X'S,U'S,OCC) SI(44,X'S,U[ISO],OCC) 
CONT SI(134,X'S,U'S,OCC) UNTIL SI(144) 
CONT O(13,X'S,U'S) UNTIL O(133) 
CONT N(1,X'S,U'S) UNTIL N(128) 
CONT C(2,X'S,U'S) UNTIL C(40) 
CONT C(102,X'S,U'S) UNTIL C(132) 
CONT C(135,X'S,U'S,OCC) UNTIL C(140) 
CONT C(145,X'S,U'S,OCC) UNTIL C(150) 
EQUIV SI(34,OCC) SI(44,OCC) 
WEIGHT -1 SI(44,OCC) 
EQUIV SI(134,OCC) SI(144,OCC) C(135,OCC) UNTIL C(140) 
CONT C(145,OCC) UNTIL C(150) 
WEIGHT -1 SI(144,OCC) C(145,OCC) UNTIL C(150) 
FIX SI(44,U[ISO]) 
RIDE C ( 2,X'S) H( 21,X'S) H( 22,X'S) 
RIDE C ( 5,X'S) H( 51,X'S) 
RIDE C ( 6,X'S) H( 61,X'S) H( 62,X'S) 
RIDE C ( 7,X'S) H( 71,X'S) 
RIDE C ( 8,X'S) H( 81,X'S) H( 82,X'S) 
RIDE C ( 9,X'S) H( 91,X'S) 
RIDE C ( 11,X'S) H( 111,X'S) 
RIDE C ( 14,X'S) H( 141,X'S) H( 142,X'S) 
RIDE C ( 17,X'S) H( 171,X'S) 
RIDE C ( 18,X'S) H( 181,X'S) 
RIDE C ( 24,X'S) H( 241,X'S) 
RIDE C ( 25,X'S) H( 251,X'S) 
RIDE C ( 26,X'S) H( 261,X'S) 
RIDE C ( 27,X'S) H( 271,X'S) 
RIDE C ( 32,X'S) H( 321,X'S) H( 322,X'S) H( 323,X'S) 
RIDE C ( 35,X'S) H( 351,X'S) H( 352,X'S) H( 353,X'S) 
RIDE C ( 38,X'S) H( 381,X'S) H( 382,X'S) H( 383,X'S) 
RIDE C ( 39,X'S) H( 391,X'S) H( 392,X'S) H( 393,X'S) 
RIDE C ( 40,X'S) H( 401,X'S) H( 402,X'S) H( 403,X'S) 
RIDE C ( 102,X'S) H(1021,X'S) H(1022,X'S) 
RIDE C ( 105,X'S) H(1051,X'S) 
RIDE C ( 106,X'S) H(1061,X'S) H(1062,X'S) 
RIDE C ( 107,X'S) H(1071,X'S) 
RIDE C ( 108,X'S) H(1081,X'S) H(1082,X'S) 
RIDE C ( 109,X'S) H(1091,X'S) 
RIDE C ( 111,X'S) H(1111,X'S) 
RIDE C ( 114,X'S) H(1141,X'S) H(1142,X'S) 
RIDE C ( 117,X'S) H(1171,X'S) 
RIDE C ( 118,X'S) H(1181,X'S) 
RIDE C ( 124,X'S) H(1241,X'S) 
RIDE C ( 125,X'S) H(1251,X'S) 
RIDE C ( 126,X'S) H(1261,X'S) 
RIDE C ( 127,X'S) H(1271,X'S) 
RIDE C ( 132,X'S) H(1321,X'S) H(1322,X'S) H(1323,X'S) 
RIDE C ( 135,X'S) H(1351,X'S) H(1352,X'S) H(1353,X'S) 
RIDE C ( 136,X'S) H(1361,X'S) H(1362,X'S) H(1363,X'S) 
RIDE C ( 138,X'S) H(1381,X'S) H(1382,X'S) H(1383,X'S) 
RIDE C ( 139,X'S) H(1391,X'S) H(1392,X'S) H(1393,X'S) 
RIDE C ( 140,X'S) H(1401,X'S) H(1402,X'S) H(1403,X'S) 
RIDE C ( 145,X'S) H(1451,X'S) H(1452,X'S) H(1453,X'S) 
RIDE C ( 146,X'S) H(1461,X'S) H(1462,X'S) H(1463,X'S) 
RIDE C ( 148,X'S) H(1481,X'S) H(1482,X'S) H(1483,X'S) 
RIDE C ( 149,X'S) H(1491,X'S) H(1492,X'S) H(1493,X'S) 
RIDE C ( 150,X'S) H(1501,X'S) H(1502,X'S) H(1503,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
REM 
DIST 1.66, .02 = O(33) TO SI(44) 
REM 
DIST 1.66, .02 = O(133) TO SI(134) 
DIST 1.82, .02 = SI(134) TO C(135), SI(134) TO C(136), SI(134) TO C(137) 
DIST 1.54, .02 = C(137) TO C(138), C(137) TO C(139) , C(137) TO C(140) 
ANGLE 110., 3. = O(133) TO SI(134) TO C(135), O(133) TO SI(134) TO C(136) 
CONT             O(133) TO SI(134) TO C(137) 
ANGLE 110., 3. = C(135) TO SI(134) TO C(136), C(135) TO SI(134) TO C(137) 
CONT             C(135) TO SI(134) TO C(137) 
ANGLE 110., 3. = SI(134) TO C(137) TO C(138), SI(134) TO C(137) TO C(139) 
CONT             SI(134) TO C(137) TO C(140) 
ANGLE 110., 3. = C(138) TO C(137) TO C(139) , C(138) TO C(137) TO C(140) 
CONT             C(139) TO C(137) TO C(140) 
REM 
DIST 1.66, .02 = O(133) TO SI(144) 
DIST 1.82, .02 = SI(144) TO C(145), SI(144) TO C(146), SI(144) TO C(147) 
DIST 1.54, .02 = C(147) TO C(148), C(147) TO C(149), C(147) TO C(140) 
ANGLE 110., 3. = O(133) TO SI(144) TO C(145), O(133) TO SI(144) TO C(146) 
CONT             O(133) TO SI(144) TO C(147) 
ANGLE 110., 3. = C(145) TO SI(144) TO C(146), C(145) TO SI(144) TO C(147) 
CONT             C(145) TO SI(144) TO C(147) 
ANGLE 110., 3. = SI(144) TO C(147) TO C(148), SI(144) TO C(147) TO C(149) 
REM CONT             SI(144) TO C(147) TO C(150) 
ANGLE 110., 3. = C(148) TO C(147) TO C(149), C(148) TO C(147) TO C(150) 
CONT             C(149) TO C(147) TO C(150) 
REM 
U(IJ) 0, .02 = SI(134) TO C(135), SI(134) TO C(136), SI(134) TO C(137) 
CONT        C(137) TO C(138),  C(137) TO C(139),  C(137) TO C(140) 
U(IJ) 0. .02 = SI(144) TO C(145), SI(144) TO C(146), SI(144) TO C(147) 
CONT        C(147) TO C(148),  C(147) TO C(149),  C(147) TO C(150) 
U(IJ) 0. .02 = SI(134) TO SI(144), C(136) TO C(146), C(137) TO C(147) 
CONT        C(138) TO C(148),  C(139) TO C(149) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;