Asymmetric syntheses of nakinadine D, nakinadine E, and nakinadine F: confirmation of their relative (RS,SR)-configurations and proposal of their absolute (2S,3R)-configurations.
Davies, Stephen G.; Fletcher, Ai M.; Shah, Rushabh S.; Roberts, Paul M.; Thomson, James E.; The Journal of organic chemistry 80 (2015) 4017–4029; doi:10.1021/acs.joc.5b00376

data_4036176
_publ_section_title
;
 Asymmetric syntheses of nakinadine D, nakinadine E, and nakinadine F:
 confirmation of their relative (RS,SR)-configurations and proposal of
 their absolute (2S,3R)-configurations.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4017
_journal_page_last               4029
_journal_paper_doi               10.1021/acs.joc.5b00376
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H48 N2 O3 S1'
_chemical_formula_sum            'C31 H48 N2 O3 S'
_chemical_formula_weight         528.80
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.750(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1712(6)
_cell_length_b                   5.58190(10)
_cell_length_c                   28.3409(9)
_cell_measurement_reflns_used    8329
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      3
_cell_volume                     3039.10(16)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_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      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            17106
_diffrn_reflns_theta_full        40.491
_diffrn_reflns_theta_max         76.398
_diffrn_reflns_theta_min         3.275
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.50
_refine_ls_abs_structure_details 'Flack (1983), 2472 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.011(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5849
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.0009103
_refine_ls_shift/su_mean         0.0000330
_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: 
 0.179E+04 0.297E+04 0.192E+04 849. 233. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0948
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0947
_reflns_limit_h_max              23
_reflns_limit_h_min              -25
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                5342
_reflns_number_total             5872
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.89
_oxford_diffrn_Wilson_scale      0.12
_oxford_refine_ls_r_factor_ref   0.0410
_oxford_refine_ls_scale          2.865(19)
_oxford_reflns_number_all        5850
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo5b00376_si_001.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C31 H48 N2 O3 S1'
_cod_database_code               4036176
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE N   (   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   (   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) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 353,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 363,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 373,X'S) H   ( 372,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;