Synthesis of the Spiroiminal Moiety and Approaches to the Synthesis of Marineosins A and B
Xiao-Chuan Cai; Barry B. Snider; Journal of Organic Chemistry 78 (2013) 12161–12175; doi:10.1021/jo402178r

data_4028835
_publ_section_title
;
 Synthesis of the Spiroiminal Moiety and Approaches to the Synthesis of
 Marineosins A and B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12161
_journal_page_last               12175
_journal_paper_doi               10.1021/jo402178r
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C17.00 H25.00 N1 O2'
_chemical_formula_sum            'C17 H25 N O2'
_chemical_formula_weight         275.39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2013-08-11
_audit_creation_method           CRYSTALS_ver_14.52
_cell_angle_alpha                90
_cell_angle_beta                 115.845(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.6957(13)
_cell_length_b                   9.4112(5)
_cell_length_c                   13.5643(7)
_cell_measurement_reflns_used    7440
_cell_measurement_temperature    160
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     3067.0(3)
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18576
_diffrn_reflns_theta_full        27.004
_diffrn_reflns_theta_max         27.004
_diffrn_reflns_theta_min         2.324
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200.000
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0230
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0048862
_refine_ls_shift/su_mean         0.0003757
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 2.92P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1117
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1117
_reflns_limit_h_max              30
_reflns_limit_h_min              -34
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3018
_reflns_number_total             3333
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0483
_oxford_refine_ls_scale          0.11364(5)
_oxford_reflns_number_all        3333
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'xccai_6_101_1_0m in C2/c'
_iucr_refine_instructions_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   17 ) 
CONT C    (  101 ,X'S,U[ISO]) H(1,X'S,U[ISO]) 
EQUIVALENCE PART(1001, OCC) 
CONTINUE    PART(1002, OCC) 
WEIGHT -1   PART(1002, OCC) 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) H   (  13,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   ( 101,X'S) H   (1011,X'S) H   (1012,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo402178r_si_002.cif
_cod_data_source_block           xccai_6_101_1
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        'C17.00 H25.00 N1 O2'
_cod_database_code               4028835