Short and Scalable Total Synthesis of Myrioneuron Alkaloids (±)-α,β-Myrifabral A and B.
Song, Dengpeng; Wang, Zhengshen; Mei, Ruoming; Zhang, Weiwei; Ma, Donghui; Xu, Dengyu; Xie, Xingang; She, Xuegong; Organic letters 18 (2016) 669–671; doi:10.1021/acs.orglett.6b00005

data_1542634
_publ_section_title
;
 Short and Scalable Total Synthesis of Myrioneuron Alkaloids
 (+-)-\a,\b-Myrifabral A and B.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              669
_journal_page_last               671
_journal_paper_doi               10.1021/acs.orglett.6b00005
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C15 H25 N O2'
_chemical_formula_sum            'C15 H25 N O2'
_chemical_formula_weight         251.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.219(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6087(13)
_cell_length_b                   12.4575(14)
_cell_length_c                   10.8471(15)
_cell_measurement_reflns_used    1287
_cell_measurement_temperature    291.48(10)
_cell_measurement_theta_max      63.1430
_cell_measurement_theta_min      5.5100
_cell_volume                     1389.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      291.48(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega   22.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 41

  2 omega   32.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 28

  3 omega  -12.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 30

  4 omega  -15.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 89

  5 omega   50.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 25

  6 omega   40.00  116.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 76

  7 omega   85.00  127.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 42

  8 omega   51.00   92.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 41

  9 omega   36.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 53

 10 omega   51.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 28

 11 omega   57.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 66

 12 omega   83.00  160.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 77

 13 omega  142.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 30

 14 omega  141.00  169.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 28

 15 omega  106.00  170.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 64

 16 omega  101.00  136.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 35

 17 omega   64.00  146.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 82

 18 omega  -12.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  -30.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1258459000
_diffrn_orient_matrix_UB_12      -0.0335594000
_diffrn_orient_matrix_UB_13      -0.0365854000
_diffrn_orient_matrix_UB_21      -0.0445426000
_diffrn_orient_matrix_UB_22      -0.1181491000
_diffrn_orient_matrix_UB_23      -0.0083025000
_diffrn_orient_matrix_UB_31      -0.0679866000
_diffrn_orient_matrix_UB_32      0.0152407000
_diffrn_orient_matrix_UB_33      -0.1415022000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5242
_diffrn_reflns_theta_full        69.77
_diffrn_reflns_theta_max         69.77
_diffrn_reflns_theta_min         4.30
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0802P)^2^+0.3691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1779
_reflns_number_gt                1839
_reflns_number_total             2565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00005_si_001.cif
_cod_data_source_block           songdp0916
_cod_database_code               1542634
_reflns_odcompleteness_completeness 99.85
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C12(H12), C13(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Idealised tetrahedral OH refined as rotating group:
 O13(H13)
;
_olex2_date_sample_data_collection 2015-09-17
_olex2_submission_special_instructions 'No special instructions were received'