Tethered Aminohydroxylation: Synthesis of the β-Amino Acid of Microsclerodermins A and B.
Pullin, Robert D. C.; Rathi, Akshat H.; Melikhova, Ekaterina Y.; Winter, Christian; Thompson, Amber L.; Donohoe, Timothy J.; Organic letters 15 (2013) 5492–5495; doi:10.1021/ol402638n

data_1512589
_publ_section_title
;
 Tethered Aminohydroxylation: Synthesis of the \b-Amino Acid of
 Microsclerodermins A and B.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5492
_journal_page_last               5495
_journal_paper_doi               10.1021/ol402638n
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C35 H51 N3 O12 Si2'
_chemical_formula_sum            'C35 H51 N3 O12 Si2'
_chemical_formula_weight         761.97
_chemical_melting_point          ?
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2013-06-26
_audit_creation_method           CRYSTALS_ver_14.52
_cell_angle_alpha                90
_cell_angle_beta                 95.462(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9112(12)
_cell_length_b                   6.4920(9)
_cell_length_c                   26.346(2)
_cell_measurement_reflns_used    5021
_cell_measurement_temperature    100
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     4071.2(7)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measurement_device
;
CrystalLogic Kappa (3 circle)
;
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.135
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14518
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         1.755
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     461
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0959
_refine_ls_shift/su_max          0.0002244
_refine_ls_shift/su_mean         0.0000126
_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: 
 0.576E+04 0.872E+04 0.518E+04 0.237E+04 611. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2229
_refine_ls_wR_factor_gt          0.2043
_refine_ls_wR_factor_ref         0.2229
_reflns_limit_h_max              30
_reflns_limit_h_min              -31
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                2417
_reflns_number_total             4586
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.40
_oxford_diffrn_Wilson_scale      0.09
_oxford_refine_ls_r_factor_ref   0.1155
_oxford_refine_ls_scale          5.8(3)
_oxford_reflns_number_all        3140
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title DIA0184
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  73,X'S) H   (  72,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  93,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 103,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 113,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 123,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE N   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 322,X'S) H   ( 321,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 452,X'S) H   ( 451,X'S) H   ( 453,X'S) 
RIDE C   (  48,X'S) H   ( 482,X'S) H   ( 481,X'S) H   ( 483,X'S) 
RIDE C   (  49,X'S) H   ( 492,X'S) H   ( 491,X'S) H   ( 493,X'S) 
RIDE C   (  50,X'S) H   ( 502,X'S) H   ( 501,X'S) H   ( 503,X'S) 
RIDE C   (  51,X'S) H   ( 512,X'S) H   ( 511,X'S) H   ( 513,X'S) 
RIDE C   (  52,X'S) H   ( 522,X'S) H   ( 521,X'S) H   ( 523,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = SI(1) TO O(2) 
VIBR .0, 0.00200 = SI(1) TO C(47) 
VIBR .0, 0.00200 = SI(1) TO C(51) 
VIBR .0, 0.00200 = SI(1) TO C(52) 
VIBR .0, 0.00500 = C(47) TO O(2) 
VIBR .0, 0.00500 = C(51) TO O(2) 
VIBR .0, 0.00500 = C(51) TO C(47) 
VIBR .0, 0.00500 = C(52) TO O(2) 
VIBR .0, 0.00500 = C(52) TO C(47) 
VIBR .0, 0.00500 = C(52) TO C(51) 
VIBR .0, 0.00200 = O(2) TO C(3) 
VIBR .0, 0.00500 = C(3) TO SI(1) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO O(2) 
VIBR .0, 0.00200 = C(4) TO O(5) 
VIBR .0, 0.00200 = C(4) TO C(13) 
VIBR .0, 0.00500 = O(5) TO C(3) 
VIBR .0, 0.00500 = C(13) TO C(3) 
VIBR .0, 0.00500 = C(13) TO O(5) 
VIBR .0, 0.00200 = O(5) TO SI(6) 
VIBR .0, 0.00500 = SI(6) TO C(4) 
VIBR .0, 0.00200 = SI(6) TO C(7) 
VIBR .0, 0.00200 = SI(6) TO C(8) 
VIBR .0, 0.00200 = SI(6) TO C(12) 
VIBR .0, 0.00500 = C(7) TO O(5) 
VIBR .0, 0.00500 = C(8) TO O(5) 
VIBR .0, 0.00500 = C(8) TO C(7) 
VIBR .0, 0.00500 = C(12) TO O(5) 
VIBR .0, 0.00500 = C(12) TO C(7) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00200 = C(8) TO C(10) 
VIBR .0, 0.00200 = C(8) TO C(11) 
VIBR .0, 0.00500 = C(9) TO SI(6) 
VIBR .0, 0.00500 = C(10) TO SI(6) 
VIBR .0, 0.00500 = C(10) TO C(9) 
VIBR .0, 0.00500 = C(11) TO SI(6) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00500 = C(11) TO C(10) 
VIBR .0, 0.00200 = C(13) TO N(14) 
VIBR .0, 0.00200 = C(13) TO C(18) 
VIBR .0, 0.00500 = N(14) TO C(4) 
VIBR .0, 0.00500 = C(18) TO C(4) 
VIBR .0, 0.00500 = C(18) TO N(14) 
VIBR .0, 0.00200 = N(14) TO C(15) 
VIBR .0, 0.00500 = C(15) TO C(13) 
VIBR .0, 0.00200 = C(15) TO O(16) 
VIBR .0, 0.00200 = C(15) TO O(46) 
VIBR .0, 0.00500 = O(16) TO N(14) 
VIBR .0, 0.00500 = O(46) TO N(14) 
VIBR .0, 0.00500 = O(46) TO O(16) 
VIBR .0, 0.00200 = O(16) TO C(17) 
VIBR .0, 0.00500 = C(17) TO C(15) 
VIBR .0, 0.00200 = C(17) TO C(18) 
VIBR .0, 0.00200 = C(17) TO C(31) 
VIBR .0, 0.00500 = C(18) TO O(16) 
VIBR .0, 0.00500 = C(31) TO O(16) 
VIBR .0, 0.00500 = C(31) TO C(18) 
VIBR .0, 0.00200 = C(18) TO O(19) 
VIBR .0, 0.00500 = C(13) TO C(17) 
VIBR .0, 0.00500 = O(19) TO C(17) 
VIBR .0, 0.00500 = O(19) TO C(13) 
VIBR .0, 0.00200 = O(19) TO C(20) 
VIBR .0, 0.00500 = C(20) TO C(18) 
VIBR .0, 0.00200 = C(20) TO O(21) 
VIBR .0, 0.00200 = C(20) TO C(22) 
VIBR .0, 0.00500 = O(21) TO O(19) 
VIBR .0, 0.00500 = C(22) TO O(19) 
VIBR .0, 0.00500 = C(22) TO O(21) 
VIBR .0, 0.00200 = C(22) TO C(23) 
VIBR .0, 0.00200 = C(22) TO C(30) 
VIBR .0, 0.00500 = C(23) TO C(20) 
VIBR .0, 0.00500 = C(30) TO C(20) 
VIBR .0, 0.00500 = C(30) TO C(23) 
VIBR .0, 0.00200 = C(23) TO C(24) 
VIBR .0, 0.00500 = C(24) TO C(22) 
VIBR .0, 0.00200 = C(24) TO C(25) 
VIBR .0, 0.00500 = C(25) TO C(23) 
VIBR .0, 0.00200 = C(25) TO N(26) 
VIBR .0, 0.00200 = C(25) TO C(29) 
VIBR .0, 0.00500 = N(26) TO C(24) 
VIBR .0, 0.00500 = C(29) TO C(24) 
VIBR .0, 0.00500 = C(29) TO N(26) 
VIBR .0, 0.00200 = N(26) TO O(27) 
VIBR .0, 0.00200 = N(26) TO O(28) 
VIBR .0, 0.00500 = O(27) TO C(25) 
VIBR .0, 0.00500 = O(28) TO C(25) 
VIBR .0, 0.00500 = O(28) TO O(27) 
VIBR .0, 0.00200 = C(29) TO C(30) 
VIBR .0, 0.00500 = C(30) TO C(25) 
VIBR .0, 0.00500 = C(29) TO C(22) 
VIBR .0, 0.00200 = C(31) TO C(32) 
VIBR .0, 0.00200 = C(31) TO C(45) 
VIBR .0, 0.00500 = C(32) TO C(17) 
VIBR .0, 0.00500 = C(45) TO C(17) 
VIBR .0, 0.00500 = C(45) TO C(32) 
VIBR .0, 0.00200 = C(32) TO O(33) 
VIBR .0, 0.00500 = O(33) TO C(31) 
VIBR .0, 0.00200 = O(33) TO C(34) 
VIBR .0, 0.00500 = C(34) TO C(32) 
VIBR .0, 0.00200 = C(34) TO O(35) 
VIBR .0, 0.00200 = C(34) TO C(36) 
VIBR .0, 0.00500 = O(35) TO O(33) 
VIBR .0, 0.00500 = C(36) TO O(33) 
VIBR .0, 0.00500 = C(36) TO O(35) 
VIBR .0, 0.00200 = C(36) TO C(37) 
VIBR .0, 0.00200 = C(36) TO C(44) 
VIBR .0, 0.00500 = C(37) TO C(34) 
VIBR .0, 0.00500 = C(44) TO C(34) 
VIBR .0, 0.00500 = C(44) TO C(37) 
VIBR .0, 0.00200 = C(37) TO C(38) 
VIBR .0, 0.00500 = C(38) TO C(36) 
VIBR .0, 0.00200 = C(38) TO C(39) 
VIBR .0, 0.00500 = C(39) TO C(37) 
VIBR .0, 0.00200 = C(39) TO N(40) 
VIBR .0, 0.00200 = C(39) TO C(43) 
VIBR .0, 0.00500 = N(40) TO C(38) 
VIBR .0, 0.00500 = C(43) TO C(38) 
VIBR .0, 0.00500 = C(43) TO N(40) 
VIBR .0, 0.00200 = N(40) TO O(41) 
VIBR .0, 0.00200 = N(40) TO O(42) 
VIBR .0, 0.00500 = O(41) TO C(39) 
VIBR .0, 0.00500 = O(42) TO C(39) 
VIBR .0, 0.00500 = O(42) TO O(41) 
VIBR .0, 0.00200 = C(43) TO C(44) 
VIBR .0, 0.00500 = C(44) TO C(39) 
VIBR .0, 0.00500 = C(43) TO C(36) 
VIBR .0, 0.00200 = C(47) TO C(48) 
VIBR .0, 0.00200 = C(47) TO C(49) 
VIBR .0, 0.00200 = C(47) TO C(50) 
VIBR .0, 0.00500 = C(48) TO SI(1) 
VIBR .0, 0.00500 = C(49) TO SI(1) 
VIBR .0, 0.00500 = C(49) TO C(48) 
VIBR .0, 0.00500 = C(50) TO SI(1) 
VIBR .0, 0.00500 = C(50) TO C(48) 
VIBR .0, 0.00500 = C(50) TO C(49) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = SI(1) TO O(2) 
U(IJ) .0, 0.04000 = SI(1) TO C(47) 
U(IJ) .0, 0.08000 = SI(1) TO C(51) 
U(IJ) .0, 0.08000 = SI(1) TO C(52) 
U(IJ) .0, 0.04000 = O(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO O(5) 
U(IJ) .0, 0.04000 = C(4) TO C(13) 
U(IJ) .0, 0.04000 = O(5) TO SI(6) 
U(IJ) .0, 0.08000 = SI(6) TO C(7) 
U(IJ) .0, 0.04000 = SI(6) TO C(8) 
U(IJ) .0, 0.08000 = SI(6) TO C(12) 
U(IJ) .0, 0.08000 = C(8) TO C(9) 
U(IJ) .0, 0.08000 = C(8) TO C(10) 
U(IJ) .0, 0.08000 = C(8) TO C(11) 
U(IJ) .0, 0.04000 = C(13) TO N(14) 
U(IJ) .0, 0.04000 = C(13) TO C(18) 
U(IJ) .0, 0.04000 = N(14) TO C(15) 
U(IJ) .0, 0.04000 = C(15) TO O(16) 
U(IJ) .0, 0.08000 = C(15) TO O(46) 
U(IJ) .0, 0.04000 = O(16) TO C(17) 
U(IJ) .0, 0.04000 = C(17) TO C(18) 
U(IJ) .0, 0.04000 = C(17) TO C(31) 
U(IJ) .0, 0.04000 = C(18) TO O(19) 
U(IJ) .0, 0.04000 = O(19) TO C(20) 
U(IJ) .0, 0.08000 = C(20) TO O(21) 
U(IJ) .0, 0.04000 = C(20) TO C(22) 
U(IJ) .0, 0.04000 = C(22) TO C(23) 
U(IJ) .0, 0.04000 = C(22) TO C(30) 
U(IJ) .0, 0.04000 = C(23) TO C(24) 
U(IJ) .0, 0.04000 = C(24) TO C(25) 
U(IJ) .0, 0.04000 = C(25) TO N(26) 
U(IJ) .0, 0.04000 = C(25) TO C(29) 
U(IJ) .0, 0.08000 = N(26) TO O(27) 
U(IJ) .0, 0.08000 = N(26) TO O(28) 
U(IJ) .0, 0.04000 = C(29) TO C(30) 
U(IJ) .0, 0.04000 = C(31) TO C(32) 
U(IJ) .0, 0.08000 = C(31) TO C(45) 
U(IJ) .0, 0.04000 = C(32) TO O(33) 
U(IJ) .0, 0.04000 = O(33) TO C(34) 
U(IJ) .0, 0.08000 = C(34) TO O(35) 
U(IJ) .0, 0.04000 = C(34) TO C(36) 
U(IJ) .0, 0.04000 = C(36) TO C(37) 
U(IJ) .0, 0.04000 = C(36) TO C(44) 
U(IJ) .0, 0.04000 = C(37) TO C(38) 
U(IJ) .0, 0.04000 = C(38) TO C(39) 
U(IJ) .0, 0.04000 = C(39) TO N(40) 
U(IJ) .0, 0.04000 = C(39) TO C(43) 
U(IJ) .0, 0.08000 = N(40) TO O(41) 
U(IJ) .0, 0.08000 = N(40) TO O(42) 
U(IJ) .0, 0.04000 = C(43) TO C(44) 
U(IJ) .0, 0.08000 = C(47) TO C(48) 
U(IJ) .0, 0.08000 = C(47) TO C(49) 
U(IJ) .0, 0.08000 = C(47) TO C(50) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            ol402638n_si_001.cif
_cod_data_source_block           13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary'
value 'Other' changed to 'other' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2 '
_cod_database_code               1512589