Total synthesis of incarviditone and incarvilleatone.
Brown, Patrick D.; Willis, Anthony C.; Sherburn, Michael S.; Lawrence, Andrew L.; Organic letters 14 (2012) 4537–4539; doi:10.1021/ol302042u

data_1508625
_publ_section_title
;
 Total synthesis of incarviditone and incarvilleatone.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4537
_journal_page_last               4539
_journal_paper_doi               10.1021/ol302042u
_journal_volume                  14
_journal_year                    2012
_chemical_compound_source        local
_chemical_formula_moiety         'C23 H25 N O7'
_chemical_formula_sum            'C23 H25 N O7'
_chemical_formula_weight         427.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-08-15
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-08-15 - Report on C23 H25 N O7
             by Anthony C. Willis
             for Pat Brown, Andy Lawrence and Mick Sherburn
2012-08-15 - passes checkcif tests with minor warnings
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2147(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4946(2)
_cell_length_b                   17.9138(4)
_cell_length_c                   10.7033(2)
_cell_measurement_reflns_used    54719
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     2006.76(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.033
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            42318
_diffrn_reflns_theta_full        27.501
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.623
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904.000
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9764
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.0994074
_refine_ls_shift/su_mean         0.0100392
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.67P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1352
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1352
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3684
_reflns_number_total             4602
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.19
_oxford_diffrn_Wilson_scale      0.76
_oxford_refine_ls_r_factor_ref   0.0609
_oxford_refine_ls_scale          1.214(6)
_oxford_reflns_number_all        4601
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '8140956 she1223'
_cod_data_source_file            ol302042u_si_002.cif
_cod_data_source_block           she1223
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               1508625
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, O(1,U'S,OCC) O(5,U'S) UNTIL O(31) O(101,U'S,OCC) 
CONT N(10,U'S) C(2,U'S,OCC) UNTIL C(4) C(6,U'S) UNTIL C(17) 
CONT C(18,U'S,OCC) UNTIL C(19) C(20,U'S) UNTIL C(29) 
CONT  C(102,U'S,OCC) UNTIL C(119) 
CONT H(1,X'S) 
EQUIV O(1,OCC)  C(2,OCC) C(3,OCC) C(4,OCC) C(18,OCC) C(19,OCC) 
CONT O(101,OCC) C(102,OCC) UNTIL C(119) 
WEIGHT -1 O(101,OCC) C(102,OCC) UNTIL C(119) 
RIDE C(2,X'S) H(21,X'S) H(22,X'S) 
RIDE C(3,X'S) H(31,X'S) H(32,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H(152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,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   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C(102,X'S) H(1021,X'S) H(1022,X'S) 
RIDE C(103,X'S) H(1031,X'S) H(1032,X'S) 
RIDE C   (  118,X'S) H   ( 1181,X'S) H   ( 1182,X'S) 
RIDE C   (  119,X'S) H   ( 1191,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.0, .01 = MEAN O(1) TO C(2),  O(101) TO C(102) 
DIST 0.0, .01 = MEAN O(1) TO C(19), O(101) TO C(119) 
DIST 0.0, .01 = MEAN C(2) TO C(3),  C(102) TO C(103) 
DIST 0.0, .01 = MEAN C(3) TO C(4),  C(103) TO C(104) 
DIST 0.0, .01 = MEAN C(17) TO C(18),  C(17) TO C(118) 
DIST 0.0, .01 = MEAN C(18) TO C(19),  C(118) TO C(119) 
DIST 0.0, .01 = MEAN C(19) TO C(4),  C(119) TO C(104) 
DIST 0.0, .01 = MEAN C(4) TO C(15), C(104) TO C(15) 
DIST 0.0, .01 = MEAN C(4) TO O(5), C(104) TO O(5) 
REM 
U(IJ) 0.0, .01 = O(1) TO O(101) 
U(IJ) 0.0, .01 = C(2) TO C(102) 
U(IJ) 0.0, .01 = C(3) TO C(103) 
U(IJ) 0.0, .01 = C(4) TO C(104) 
U(IJ) 0.0, .01 = C(18) TO C(118) 
U(IJ) 0.0, .01 = C(19) TO C(119) 
REM 
VIBR 0.0, .01 = O(1) TO C(2), C(2) TO C(3), C(3) TO C(4) 
CONT C(4) TO O(5), C(4) TO C(15), C(4) TO C(19) 
CONT C(19) TO C(18), C(18) TO C(17), O(1) TO C(19) 
REM 
VIBR 0.0, .01 = O(101) TO C(102), C(102) TO C(103), C(103) TO C(104) 
CONT C(104) TO O(5), C(104) TO C(15), C(104) TO C(119) 
CONT C(119) TO C(118), C(118) TO C(17), O(101) TO C(119) 
REM 
LIMIT C(3,U[13]) 
LIMIT C(19,Z) 
LIMIT O(101,Z) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;