A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine Alkaloid Gilbertine.
Tang, Fei; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 81 (2016) 10551–10557; doi:10.1021/acs.joc.6b01424

data_4037079
_publ_section_title
;
 A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine
 Alkaloid Gilbertine.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10551
_journal_page_last               10557
_journal_paper_doi               10.1021/acs.joc.6b01424
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        local
_chemical_formula_moiety         'C23 H22 N2 O4'
_chemical_formula_sum            'C23 H22 N2 O4'
_chemical_formula_weight         390.44
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             16-04-19
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
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2016-04-19 - Report on C23 H22 N2 O4 
             by Anthony C. Willis
             for   Fei Tang and Martin Banwell

2016-04-19 - details of refinement in _refine_special_details below

2016-04-19 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                109.830(4)
_cell_angle_beta                 97.254(3)
_cell_angle_gamma                99.900(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8560(2)
_cell_length_b                   11.9176(4)
_cell_length_c                   15.3239(7)
_cell_measurement_reflns_used    6879
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     971.19(7)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_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      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14521
_diffrn_reflns_theta_full        71.213
_diffrn_reflns_theta_max         72.299
_diffrn_reflns_theta_min         4.052
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.0034869
_refine_ls_shift/su_mean         0.0001480
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.41P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1048
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1048
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3382
_reflns_number_total             3819
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.87
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0466
_oxford_refine_ls_scale          8.6(3)
_oxford_reflns_number_all        3819
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1626SN\Tony_ban1626SN_data At 11:36 on'
_cod_data_source_file            jo6b01424_si_003.cif
_cod_data_source_block           ban1626SN
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4037079
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT C(13,OCC) C(14,OCC) O(4,OCC) C(15,OCC) 
CONT C(113,OCC) C(114,OCC) O(104,OCC) C(115,OCC) 
EQUIV C(13,OCC) C(14,OCC) O(4,OCC) C(15,OCC) 
CONT C(113,OCC) C(114,OCC) O(104,OCC) C(115,OCC) 
WEIGHT -1 C(113,OCC) C(114,OCC) O(104,OCC) C(115,OCC) 
RIDE C ( 2,X'S) H( 21,X'S) 
RIDE C ( 3,X'S) H( 31,X'S) 
RIDE C ( 4,X'S) H( 41,X'S) 
RIDE C ( 5,X'S) H( 51,X'S) 
RIDE C ( 8,X'S) H( 81,X'S) 
RIDE C ( 10,X'S) H( 101,X'S) 
RIDE C ( 11,X'S) H( 111,X'S) H( 112,X'S) 
RIDE C ( 17,X'S) H( 171,X'S) 
RIDE C ( 18,X'S) H( 181,X'S) 
RIDE C ( 19,X'S) H( 191,X'S) 
RIDE C ( 20,X'S) H( 201,X'S) 
RIDE C ( 21,X'S) H( 211,X'S) 
RIDE C ( 22,X'S) H( 221,X'S) H( 222,X'S) 
RIDE C(9,X'S) H(91,X'S) H(92,X'S) 
RIDE C(13,X'S) H(131,X'S) H(132,X'S) 
RIDE C(14,X'S) H(141,X'S) H(142,X'S) 
RIDE C(15,X'S) H(151,X'S) H(152,X'S) 
RIDE C(113,X'S) H(1131,X'S) H(1132,X'S) 
RIDE C(114,X'S) H(1141,X'S) H(1142,X'S) 
RIDE C(115,X'S) H(1151,X'S) H(1152,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
DIST 1.41, .02 = C(14) TO O(4), C(114) TO O(104) 
DIST 1.41, .02 = C(15) TO O(4), C(115) TO O(104) 
DIST 1.51, .02 = C(15) TO C(16), C(115) TO C(16) 
U(IJ) 0.0, .01 = O(4) TO O(104) 
U(IJ) 0.0, .01 = C(15) TO C(115) 
REM 
DIST 1.54, .005 = C(9) TO C(13), C(9) TO C(113) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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