Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME).
Liu, Xin; Hu, Ya-Jian; Chen, Bo; Min, Long; Peng, Xiao-Shui; Zhao, Jing; Li, Shaoping; Wong, Henry N. C.; Li, Chuang-Chuang; Organic letters 19 (2017) 4612–4615; doi:10.1021/acs.orglett.7b02224

data_1547028
_publ_section_title
;
 Asymmetric Total Syntheses of Colchicine, \b-Lumicolchicine, and
 Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME).
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4612
_journal_page_last               4615
_journal_paper_doi               10.1021/acs.orglett.7b02224
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H27 N O6'
_chemical_formula_sum            'C22 H27 N O6'
_chemical_formula_weight         401.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.593(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.467(3)
_cell_length_b                   9.477(5)
_cell_length_c                   14.485(5)
_cell_measurement_reflns_used    1165
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.6
_cell_measurement_theta_min      23.8
_cell_volume                     1016.0(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
scan:
    Number of images: 180
               Slice: -134.0000 - 46.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 0.0000
                 XTD: 45.2001
              2theta: -44.1596
scan:
    Number of images: 45
               Slice: -21.0000 - 24.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 45.2001
              2theta: -44.1596
scan:
    Number of images: 44
               Slice: -112.0000 - -68.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.2001
              2theta: -44.1596
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.2001
              2theta: -90.1596
scan:
    Number of images: 156
               Slice: -180.0000 - -24.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.2001
              2theta: -90.1596
scan:
    Number of images: 90
               Slice: -112.0000 - -22.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 45.2001
              2theta: -90.1596
scan:
    Number of images: 75
               Slice: -123.0000 - -48.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 180.0000
                 XTD: 45.2001
              2theta: -90.1596
;
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.086200
_diffrn_orient_matrix_UB_12      -0.099494
_diffrn_orient_matrix_UB_13      0.030379
_diffrn_orient_matrix_UB_21      -0.071782
_diffrn_orient_matrix_UB_22      0.071322
_diffrn_orient_matrix_UB_23      0.029905
_diffrn_orient_matrix_UB_31      -0.030773
_diffrn_orient_matrix_UB_32      -0.004854
_diffrn_orient_matrix_UB_33      -0.062290
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5530
_diffrn_reflns_point_group_measured_fraction_full 0.743
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.909
_diffrn_reflns_theta_min         3.078
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           0.9
_diffrn_source_power             0.0
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 598 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.3(4)
_refine_ls_extinction_coef       0.090(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1448P)^2^+0.1342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2555
_reflns_Friedel_coverage         0.438
_reflns_Friedel_fraction_full    0.484
_reflns_Friedel_fraction_max     0.482
_reflns_number_gt                1923
_reflns_number_total             2739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02224_si_002.cif
_cod_data_source_block           20170719
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1016.1(8)
_cod_database_code               1547028
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), N7(H7), C11(H11), C16(H16), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              34550
_shelx_hkl_checksum              36270
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'