Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement.
Liu, Dandan; Ai, Long; Li, Fan; Zhao, Annan; Chen, Jingbo; Zhang, Hongbin; Liu, Jianping; Organic & biomolecular chemistry 12 (2014) 3191–3200; doi:10.1039/c4ob00126e

data_7153812
_publ_section_title
;
 Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening
 rearrangement.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3191
_journal_page_last               3200
_journal_paper_doi               10.1039/c4ob00126e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C16 H16 Br N O2'
_chemical_formula_sum            'C16 H16 Br N O2'
_chemical_formula_weight         334.21
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.452(2)
_cell_angle_beta                 95.382(2)
_cell_angle_gamma                93.343(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7674(11)
_cell_length_b                   9.4798(13)
_cell_length_c                   9.7608(14)
_cell_measurement_reflns_used    5439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.16
_cell_volume                     693.53(17)
_computing_cell_refinement       'Bruker apex II'
_computing_data_collection       'Bruker apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean no
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  no
_diffrn_measurement_method       no
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6027
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        no
_diffrn_standards_interval_count no
_diffrn_standards_interval_time  no
_diffrn_standards_number         no
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_T_max  0.7559
_exptl_absorpt_correction_T_min  0.5749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0402P)^2^+0.0856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                2131
_reflns_number_total             3149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00126e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153812