(-)-(2S,3R,Z)-Nakinadine A: First Asymmetric Synthesis and Absolute Configuration Assignment.
Davies, Stephen G.; Fletcher, Ai M.; Roberts, Paul M.; Shah, Rushabh S.; Thompson, Amber L.; Thomson, James E.; Organic letters 16 (2014) 1354–1357; doi:10.1021/ol500096r

data_1513819
_publ_section_title
;
 (-)-(2S,3R,Z)-Nakinadine A: First Asymmetric Synthesis and Absolute
 Configuration Assignment.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1354
_journal_page_last               1357
_journal_paper_doi               10.1021/ol500096r
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H50 N2 O3 S1'
_chemical_formula_sum            'C32 H50 N2 O3 S'
_chemical_formula_weight         542.83
_chemical_melting_point          341.6(5)
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             13-12-09
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 93.453(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1901(5)
_cell_length_b                   5.6134(2)
_cell_length_c                   39.9231(17)
_cell_measurement_reflns_used    6822
_cell_measurement_temperature    100
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     3398.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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 0.956
_diffrn_measured_fraction_theta_max 0.916
_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  0.055
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21094
_diffrn_reflns_theta_full        25.176
_diffrn_reflns_theta_max         26.782
_diffrn_reflns_theta_min         1.916
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.061
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1184.000
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_platon_squeeze_details
;
The discrete Fourier transform of the void region were treated as 
contributions to the A and B parts of the calculated structure factors.
;
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details 'Flack (1983), 2989 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.15(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6439
_refine_ls_number_restraints     305
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.0008204
_refine_ls_shift/su_mean         0.0000446
_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: 
 0.594E+04 0.988E+04 0.677E+04 0.315E+04 0.105E+04 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2067
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2067
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              50
_reflns_limit_l_min              0
_reflns_number_gt                5397
_reflns_number_total             7017
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.33
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0767
_oxford_refine_ls_scale          6.2(2)
_oxford_reflns_number_all        6439
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title SGD486
_cod_data_source_file            ol500096r_si_002.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '68-69 \%C' was changed to '341.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was
estimated.

'_atom_sites_solution_primary' value 'Other' changed to
'other' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z 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      'I 2'
_cod_original_formula_sum        'C32 H50 N2 O3 S1'
_cod_database_code               1513819
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE N   (   1,X'S) H   (   1,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
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   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  94,X'S) H   (  93,X'S) 
CONT H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 203,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,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   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  33,X'S) H   ( 333,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) H   (1102,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) H   (1112,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) H   (1122,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) H   (1132,X'S) 
RIDE C   ( 115,X'S) H   (1151,X'S) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   ( 117,X'S) H   (1171,X'S) 
RIDE C   ( 119,X'S) H   (1191,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
SAME  C(9)  C(10)  C(11)  C(12)  C(13)  C(14)  AND 
CONT  C(14)  C(13)  C(12)  C(11)  C(10)  C(9)  AND 
CONT  C(9)  C(110)  C(111)  C(112)  C(113)  C(114)  AND 
CONT  C(114)  C(113)  C(112)  C(111)  C(110)  C(9) 
SIMU  0.01  C(9)  C(10)  C(11)  C(12)  C(13)  C(14)  AND 
CONT  C(14)  C(13)  C(12)  C(11)  C(10)  C(9)  AND 
CONT  C(9)  C(110)  C(111)  C(112)  C(113)  C(114)  AND 
CONT  C(114)  C(113)  C(112)  C(111)  C(110)  C(9) 
DELU  0.01  C(9)  C(10)  C(11)  C(12)  C(13)  C(14)  AND 
CONT  C(14)  C(13)  C(12)  C(11)  C(10)  C(9)  AND 
CONT  C(9)  C(110)  C(111)  C(112)  C(113)  C(114)  AND 
CONT  C(114)  C(113)  C(112)  C(111)  C(110)  C(9) 
SAME  C(13)  C(14)  C(15)  C(16)  C(17)  N(2)  C(19)  AND 
CONT  C(113)  C(114)  C(115)  C(116)  C(117)  N(102)  C(119) 
SIMU  0.01  C(13)  C(14)  C(15)  C(16)  C(17)  N(2)  C(19)  AND 
CONT  C(113)  C(114)  C(115)  C(116)  C(117)  N(102)  C(119) 
DELU  0.01  C(13)  C(14)  C(15)  C(16)  C(17)  N(2)  C(19)  AND 
CONT  C(113)  C(114)  C(115)  C(116)  C(117)  N(102)  C(119) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;