Total synthesis of securinega alkaloids (‒)-norsecurinine, (‒)-niruroidine and (‒)-flueggine A
Nan Ma; Yiwu Yao; Bing-Xin Zhao; Ying Wang; Wen-Cai Ye; Sheng Jiang; Chem.Commun. 50 (2014) 9284–; doi:10.1039/C4cc02575J

data_7115443
_publ_section_title
;
 Total synthesis of securinega alkaloids (--)-norsecurinine,
 (--)-niruroidine and (--)-flueggine A
;
_journal_name_full               Chem.Commun.
_journal_page_first              9284
_journal_paper_doi               10.1039/C4cc02575J
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         '0.92(C15 H15 Cl4 N O4)'
_chemical_formula_sum            'C13.846 H13.846 Cl3.692 N0.923 O3.692'
_chemical_formula_weight         383.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-04-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            13
_cell_length_a                   10.26770(14)
_cell_length_b                   22.1493(3)
_cell_length_c                   23.3892(4)
_cell_measurement_reflns_used    19069
_cell_measurement_temperature    108.6(6)
_cell_measurement_theta_max      66.5540
_cell_measurement_theta_min      3.7770
_cell_volume                     5319.23(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
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olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      108.6(6)
_diffrn_detector_area_resol_mean 10.4015
_diffrn_measured_fraction_theta_full 0.9853
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_details
;
  1 omega  -34.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8640  -38.0000  -60.0000 99

  2 omega   52.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8640   57.0000   90.0000 63

  3 omega   28.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8640 -125.0000 -180.0000 47

  4 omega   21.00   76.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  120.0000 55

  5 omega   19.00   53.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 34

  6 omega   67.00   92.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 25

  7 omega   56.00   83.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  120.0000 27

  8 omega   34.00   70.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 36

  9 omega   21.00   47.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000 -150.0000 26

 10 omega   50.00   76.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -101.0000 -112.0000 26

 11 omega   39.00   74.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -90.0000 35

 12 omega   20.00   48.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   90.0000 28

 13 omega   54.00   80.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   90.0000 26

 14 omega   26.00   82.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  150.0000 56

 15 omega   24.00   69.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000    0.0000 45

 16 omega  103.00  129.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000 -150.0000 26

 17 omega   18.00   64.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   60.0000 46

 18 omega   35.00   61.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 26

 19 omega   80.00  106.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 26

 20 omega   14.00   40.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -101.0000 -112.0000 26

 21 omega   62.00  129.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  120.0000 67

 22 omega   58.00  104.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  120.0000 46

 23 omega   19.00   49.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000 -180.0000 30

 24 omega   69.00   95.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 26

 25 omega  108.00  134.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 26

 26 omega   18.00   89.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  -30.0000 71

 27 omega   50.00   81.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   30.0000 31

 28 omega   16.00   41.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   60.0000 25

 29 omega   46.00   71.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -150.0000 25

 30 omega   13.00   39.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000    0.0000 26

 31 omega   50.00   75.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -180.0000 25

 32 omega  138.00  176.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 38

 33 omega   65.00   90.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1161759000
_diffrn_orient_matrix_UB_12      -0.0290039000
_diffrn_orient_matrix_UB_13      -0.0313926000
_diffrn_orient_matrix_UB_21      -0.0831540000
_diffrn_orient_matrix_UB_22      0.0056947000
_diffrn_orient_matrix_UB_23      0.0545339000
_diffrn_orient_matrix_UB_31      -0.0459133000
_diffrn_orient_matrix_UB_32      0.0629824000
_diffrn_orient_matrix_UB_33      -0.0193665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            42381
_diffrn_reflns_theta_full        66.5455
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         2.75
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.5549
_exptl_crystal_F_000             2568.0934
_refine_diff_density_max         0.3737
_refine_diff_density_min         -0.3341
_refine_diff_density_rms         0.0656
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.017(9)
_refine_ls_d_res_high            0.8404
_refine_ls_d_res_low             16.0824
_refine_ls_goodness_of_fit_ref   1.0444
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    75
_refine_ls_number_parameters     648
_refine_ls_number_reflns         9352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0444
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+1.5168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.996
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              -26
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                8627
_reflns_number_total             9352
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4cc02575j3.cif
_cod_data_source_block           exp_559_chendong
_cod_original_cell_volume        5319.23(13)
_cod_database_code               7115443
_chemical_oxdiff_formula         C15H15Cl4NO4
_chemical_oxdiff_usercomment     jiangsheng
_reflns_odcompleteness_completeness 98.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C42(H42), C45(H45), C47(H47), C52(H52), C55(H55), C65(H65)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C30(H30a,H30b), C32(H32a,H32b), C33(H33a,H33b), C38(H38a,
 H38b), C40(H40a,H40b), C41(H41a,H41b), C44(H44a,H44b), C51(H51a,H51b),
 C53(H53a,H53b), C54(H54a,H54b), C58(H58a,H58b), C60(H60a,H60b), C62(H62a,H62b),
  C71(H71a,H71b)
2.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C43(H43), C46(H46), C57(H57), C59(H59), C64(H64),
 C68(H68), C70(H70)
;