Total Synthesis of Hyacinthacine A2: Stereocontrolled 5-aza-cyclooctene Photoisomerization and Transannular Hydroamination with Planar-to-Point Chirality Transfer.
Royzen, Maksim; Taylor, Michael T.; Deangelis, Andrew; Fox, Joseph M.; Chemical science (Royal Society of Chemistry : 2010) 2 (2011) 2162–2165; doi:10.1039/C1SC00442E

data_1515577
_publ_section_title
;
 Total Synthesis of Hyacinthacine A2: Stereocontrolled 5-aza-cyclooctene
 Photoisomerization and Transannular Hydroamination with Planar-to-Point
 Chirality Transfer.
;
_journal_issue                   11
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              2162
_journal_page_last               2165
_journal_paper_doi               10.1039/C1SC00442E
_journal_volume                  2
_journal_year                    2011
_chemical_formula_sum            'C13 H18 F3 N O4'
_chemical_formula_weight         309.28
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.084(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.548(4)
_cell_length_b                   5.573(2)
_cell_length_c                   13.512(5)
_cell_measurement_reflns_used    992
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.18
_cell_volume                     703.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8941
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.0819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                3258
_reflns_number_total             3485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00442e.txt
_cod_data_source_block           joef080
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/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 
;
_cod_original_cell_volume        703.0(5)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1515577