De Novo Synthesis of the DEF-Ring Stereotriad Core of the Veratrum Alkaloids
Horwitz, Matthew A.; Robins, Jacob G.; Johnson, Jeffrey S.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c00685

data_4038313
_publ_section_title
;
 De Novo Synthesis of the DEF-Ring Stereotriad Core of the Veratrum
 Alkaloids
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00685
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N1 O3'
_chemical_formula_sum            'C21 H21 N O3'
_chemical_formula_weight         335.40
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2020-03-09
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9604(3)
_cell_length_b                   11.1296(2)
_cell_length_c                   11.0998(2)
_cell_measurement_reflns_used    3532
_cell_measurement_temperature    150
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     1724.62(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14308
_diffrn_reflns_theta_full        72.494
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         5.082
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block fragment'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details 'Flack (1983), 2525 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.0002080
_refine_ls_shift/su_mean         0.0000231
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.46P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1211
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1211
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -13
_reflns_number_gt                2837
_reflns_number_total             3371
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.14
_oxford_diffrn_Wilson_scale      17.64
_oxford_refine_ls_r_factor_ref   0.0558
_oxford_refine_ls_scale          0.2364(3)
_oxford_reflns_number_all        3356
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '20017_0ma in Pna2(1)'
_cod_data_source_file            jo0c00685_si_001.cif
_cod_data_source_block           20017
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_original_formula_sum        'C21 H21 N1 O3'
_cod_database_code               4038313