#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:20:51 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178946 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/75/4117591.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4117591
loop_
_publ_author_name
'Gregory L. Adams'
'Patrick J. Carroll'
'Amos B. Smith'
_publ_section_title
;
 Total Synthesis of (+)-Scholarisine A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4037
_journal_page_last               4040
_journal_paper_doi               10.1021/ja211840k
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5505(4)
_cell_length_b                   8.8117(5)
_cell_length_c                   18.9261(11)
_cell_measurement_temperature    143(1)
_cell_volume                     1092.43(11)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9445
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0293
_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/[σ²(Fo²)+(0.0533P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                1816
_reflns_number_total             1936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211840k_si_004.cif
_cod_data_source_block           UP1296-Cmpd(-)-18
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4117591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4349(2) 0.77614(16) 0.44288(7) 0.0251(3) Uani 1 1 d .
C2 C 0.4738(2) 0.72204(16) 0.36665(7) 0.0224(3) Uani 1 1 d .
C3 C 0.4193(2) 0.55366(15) 0.35571(7) 0.0235(3) Uani 1 1 d .
H3 H 0.4749 0.5216 0.3100 0.031 Uiso 1 1 calc R
C4 C 0.1874(2) 0.52685(16) 0.35446(8) 0.0280(3) Uani 1 1 d .
H4A H 0.1265 0.5756 0.3953 0.037 Uiso 1 1 calc R
H4B H 0.1306 0.5738 0.3125 0.037 Uiso 1 1 calc R
C5 C 0.1319(3) 0.36059(18) 0.35491(8) 0.0365(4) Uani 1 1 d .
H5 H 0.0336 0.3275 0.3190 0.049 Uiso 1 1 calc R
C6 C 0.2805(3) 0.24660(18) 0.37859(8) 0.0403(4) Uani 1 1 d .
H6 H 0.2677 0.1463 0.3567 0.054 Uiso 1 1 calc R
C7 C 0.4908(3) 0.28987(18) 0.40141(9) 0.0385(4) Uani 1 1 d .
H7A H 0.5868 0.2555 0.3658 0.051 Uiso 1 1 calc R
H7B H 0.5222 0.2365 0.4449 0.051 Uiso 1 1 calc R
C8 C 0.5240(2) 0.46047(16) 0.41352(7) 0.0280(3) Uani 1 1 d .
H8 H 0.6710 0.4807 0.4112 0.037 Uiso 1 1 calc R
C9 C 0.4476(3) 0.51149(17) 0.48530(7) 0.0313(3) Uani 1 1 d .
H9A H 0.3082 0.4767 0.4914 0.042 Uiso 1 1 calc R
H9B H 0.5301 0.4639 0.5216 0.042 Uiso 1 1 calc R
C10 C 0.7041(2) 0.75477(17) 0.34987(8) 0.0295(3) Uani 1 1 d .
H10A H 0.7868 0.7116 0.3873 0.039 Uiso 1 1 calc R
H10B H 0.7398 0.7030 0.3064 0.039 Uiso 1 1 calc R
C11 C 0.7585(2) 0.92151(18) 0.34221(8) 0.0339(3) Uani 1 1 d .
H11A H 0.6850 0.9640 0.3030 0.051 Uiso 1 1 calc R
H11B H 0.9026 0.9313 0.3340 0.051 Uiso 1 1 calc R
H11C H 0.7224 0.9746 0.3847 0.051 Uiso 1 1 calc R
C12 C 0.3507(2) 0.81658(15) 0.31827(7) 0.0250(3) Uani 1 1 d .
N1 N 0.26128(19) 0.88536(15) 0.27773(7) 0.0338(3) Uani 1 1 d .
O1 O 0.45340(16) 0.67590(12) 0.49517(5) 0.0314(3) Uani 1 1 d .
O2 O 0.40343(17) 0.90730(12) 0.45687(5) 0.0344(3) Uani 1 1 d .
O3 O 0.1129(2) 0.29138(13) 0.42377(6) 0.0447(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O1 119.27(12)
O2 C1 C2 122.11(13)
O1 C1 C2 118.39(12)
C12 C2 C3 109.47(11)
C12 C2 C1 108.39(11)
C3 C2 C1 112.68(11)
C12 C2 C10 107.21(11)
C3 C2 C10 111.91(11)
C1 C2 C10 106.97(11)
C8 C3 C4 111.81(12)
C8 C3 C2 108.47(11)
C4 C3 C2 112.29(11)
C5 C4 C3 112.78(12)
O3 C5 C6 59.53(11)
O3 C5 C4 115.83(13)
C6 C5 C4 120.37(15)
O3 C6 C5 59.39(11)
O3 C6 C7 117.37(13)
C5 C6 C7 121.67(14)
C6 C7 C8 115.07(13)
C9 C8 C3 109.47(11)
C9 C8 C7 112.16(13)
C3 C8 C7 110.78(12)
O1 C9 C8 113.57(11)
C11 C10 C2 115.04(11)
N1 C12 C2 175.98(15)
C1 O1 C9 124.07(11)
C5 O3 C6 61.07(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2034(17)
C1 O1 1.3321(17)
C1 C2 1.5408(19)
C2 C12 1.4774(19)
C2 C3 1.5401(19)
C2 C10 1.5679(18)
C3 C8 1.5305(19)
C3 C4 1.5373(19)
C4 C5 1.510(2)
C5 O3 1.4443(19)
C5 C6 1.469(2)
C6 O3 1.446(2)
C6 C7 1.493(3)
C7 C8 1.536(2)
C8 C9 1.5161(19)
C9 O1 1.4612(17)
C10 C11 1.519(2)
C12 N1 1.1399(18)
