Total Syntheses of the Resorcylic Acid Lactones Paecilomycin F and Cochliomycin C Using an Intramolecular Loh-Type α-Allylation Reaction for Macrolide Formation.
Ma, Xiang; Bolte, Benoit; Banwell, Martin G.; Willis, Anthony C.; Organic letters 18 (2016) 4226–4229; doi:10.1021/acs.orglett.6b01963

data_1555670
_publ_section_title
;
 Total Syntheses of the Resorcylic Acid Lactones Paecilomycin F and
 Cochliomycin C Using an Intramolecular Loh-Type \a-Allylation Reaction
 for Macrolide Formation.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4226
_journal_page_last               4229
_journal_paper_doi               10.1021/acs.orglett.6b01963
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         '3(C19 H25 Cl O7), H2 O'
_chemical_formula_sum            'C57 H77 Cl3 O22'
_chemical_formula_weight         1218.57
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-09-11
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-09-14 - Report on 3(C19 H25 Cl O7), H2 O
            by Anthony C. Willis
            for   Xiang Ma and Martin Banwell

2015-09-14 - passes checkcif tests with minor warnings

2016-02-04 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3838(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   20.6774(2)
_cell_length_b                   5.6019(1)
_cell_length_c                   25.4783(2)
_cell_measurement_reflns_used    18584
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      3
_cell_volume                     2951.15(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            46899
_diffrn_reflns_theta_full        72.252
_diffrn_reflns_theta_max         72.252
_diffrn_reflns_theta_min         2.743
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.78
_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            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.58
_refine_ls_abs_structure_details 'Flack (1983), 4530 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.012(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         10959
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.0138075
_refine_ls_shift/su_mean         0.0003410
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.76P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1171
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1171
_reflns_limit_h_max              25
_reflns_limit_h_min              -25
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                10503
_reflns_number_total             10967
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.54
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0432
_oxford_refine_ls_scale          4.60(6)
_oxford_reflns_number_all        10959
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1540SN\Tony_ban1540SN_data At 10: 3 on'
_cod_data_source_file            ol6b01963_si_002.cif
_cod_data_source_block           ban1540SN
_cod_original_cell_volume        2951.16(6)
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1555670
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, CL(1,U'S) UNTIL O(207) 
CONT O(501,U'S) UNTIL O(502) O(503,U[ISO]) 
CONT C(1,U'S) UNTIL C(219) 
CONT ENANTIO 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE O   (   3,X'S) H   (   2,X'S) 
RIDE O   (   4,X'S) H   (   3,X'S) 
RIDE O   (   5,X'S) H   (   4,X'S) 
RIDE O   ( 101,X'S) H   (   5,X'S) 
RIDE O   ( 103,X'S) H   (   6,X'S) 
RIDE O   ( 104,X'S) H   (   7,X'S) 
RIDE O   ( 105,X'S) H   (   8,X'S) 
RIDE O   ( 201,X'S) H   (   9,X'S) 
RIDE O   ( 203,X'S) H   (  10,X'S) 
RIDE O   ( 204,X'S) H   (  11,X'S) 
RIDE O   ( 205,X'S) H   (  12,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,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   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) 
RIDE C   ( 107,X'S) H   (1071,X'S) 
RIDE C   ( 108,X'S) H   (1081,X'S) 
RIDE C   ( 109,X'S) H   (1091,X'S) H   (1092,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) 
RIDE C   ( 112,X'S) H   (1121,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) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   ( 118,X'S) H   (1181,X'S) H   (1182,X'S) H   (1183,X'S) 
RIDE C   ( 119,X'S) H   (1191,X'S) H   (1192,X'S) H   (1193,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) 
RIDE C   ( 207,X'S) H   (2071,X'S) 
RIDE C   ( 208,X'S) H   (2081,X'S) 
RIDE C   ( 209,X'S) H   (2091,X'S) H   (2092,X'S) 
RIDE C   ( 210,X'S) H   (2101,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) 
RIDE C   ( 213,X'S) H   (2131,X'S) H   (2132,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) H   (2142,X'S) 
RIDE C   ( 215,X'S) H   (2151,X'S) H   (2152,X'S) 
RIDE C   ( 216,X'S) H   (2161,X'S) 
RIDE C   ( 218,X'S) H   (2181,X'S) H   (2182,X'S) H   (2183,X'S) 
RIDE C   ( 219,X'S) H   (2191,X'S) H   (2192,X'S) H   (2193,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
LIMIT O(502,Y) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;