#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:20:51 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178946 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/75/4117594.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_4117594
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            'C10 H11 N O2'
_chemical_formula_weight         177.20
_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                   6.1390(4)
_cell_length_b                   11.7027(8)
_cell_length_c                   12.4248(9)
_cell_measurement_temperature    143(1)
_cell_volume                     892.63(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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0073
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19116
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0231
_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)+(0.0359P)²+0.1194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                1554
_reflns_number_total             1582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211840k_si_007.cif
_cod_data_source_block           UP1333-Cmpd(+)-16
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4117594
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 0.48269(16) 0.29091(9) 0.53911(9) 0.0243(2) Uani 1 1 d .
C2 C 0.51820(17) 0.38319(8) 0.45435(8) 0.0214(2) Uani 1 1 d .
H2 H 0.6758 0.3955 0.4500 0.028 Uiso 1 1 calc R
C3 C 0.41539(17) 0.50065(8) 0.47727(9) 0.0240(2) Uani 1 1 d .
H3 H 0.2583 0.4960 0.4639 0.032 Uiso 1 1 calc R
C4 C 0.5123(2) 0.59258(9) 0.40486(9) 0.0299(3) Uani 1 1 d .
H4a H 0.5223 0.5634 0.3320 0.040 Uiso 1 1 calc R
H4b H 0.4157 0.6582 0.4039 0.040 Uiso 1 1 calc R
C5 C 0.7345(2) 0.63014(10) 0.44136(10) 0.0333(3) Uani 1 1 d .
H5 H 0.8199 0.6720 0.3937 0.044 Uiso 1 1 calc R
C6 C 0.8150(2) 0.60684(9) 0.53761(11) 0.0344(3) Uani 1 1 d .
H6 H 0.9549 0.6324 0.5534 0.046 Uiso 1 1 calc R
C7 C 0.6952(2) 0.54201(11) 0.62255(10) 0.0350(3) Uani 1 1 d .
H7a H 0.7093 0.5820 0.6906 0.047 Uiso 1 1 calc R
H7b H 0.7613 0.4672 0.6308 0.047 Uiso 1 1 calc R
C8 C 0.45256(19) 0.52715(10) 0.59626(9) 0.0292(3) Uani 1 1 d .
H8 H 0.3791 0.5995 0.6125 0.039 Uiso 1 1 calc R
C9 C 0.3476(2) 0.43545(11) 0.66343(10) 0.0353(3) Uani 1 1 d .
H9a H 0.3747 0.4515 0.7388 0.047 Uiso 1 1 calc R
H9b H 0.1914 0.4376 0.6521 0.047 Uiso 1 1 calc R
C10 C 0.45041(18) 0.33886(9) 0.34920(9) 0.0255(2) Uani 1 1 d .
N1 N 0.39561(19) 0.30812(9) 0.26635(8) 0.0385(3) Uani 1 1 d .
O1 O 0.42743(14) 0.32061(7) 0.63860(6) 0.0330(2) Uani 1 1 d .
O2 O 0.51786(13) 0.19175(6) 0.51917(7) 0.0309(2) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0151(5) 0.0271(5) 0.0306(5) 0.0044(4) -0.0010(4) 0.0001(4)
C2 0.0192(5) 0.0197(5) 0.0252(5) -0.0012(4) 0.0008(4) -0.0002(4)
C3 0.0212(5) 0.0210(5) 0.0299(6) -0.0036(4) -0.0041(4) 0.0034(4)
C4 0.0349(6) 0.0211(5) 0.0337(6) 0.0003(4) -0.0068(5) 0.0014(5)
C5 0.0334(6) 0.0201(5) 0.0465(7) 0.0010(5) -0.0014(6) -0.0031(5)
C6 0.0279(6) 0.0249(6) 0.0503(7) -0.0076(5) -0.0085(6) -0.0023(4)
C7 0.0346(6) 0.0371(7) 0.0332(6) -0.0076(5) -0.0107(5) -0.0010(5)
C8 0.0279(6) 0.0297(6) 0.0299(6) -0.0086(4) -0.0017(5) 0.0046(5)
C9 0.0344(6) 0.0442(7) 0.0273(6) -0.0072(5) 0.0035(5) 0.0048(5)
C10 0.0267(5) 0.0204(5) 0.0295(6) -0.0006(4) 0.0055(5) -0.0009(4)
N1 0.0454(6) 0.0398(6) 0.0303(5) -0.0076(5) 0.0018(5) -0.0031(5)
O1 0.0322(4) 0.0383(5) 0.0285(4) 0.0077(3) 0.0037(3) 0.0034(4)
O2 0.0243(4) 0.0213(4) 0.0472(5) 0.0070(3) 0.0008(3) 0.0006(3)
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 119.25(10)
O2 C1 C2 120.95(10)
O1 C1 C2 119.62(9)
C10 C2 C1 108.93(8)
C10 C2 C3 111.38(9)
C1 C2 C3 116.51(9)
C4 C3 C8 111.70(9)
C4 C3 C2 111.18(9)
C8 C3 C2 107.40(9)
C5 C4 C3 112.50(10)
C6 C5 C4 123.48(11)
C5 C6 C7 124.04(11)
C6 C7 C8 112.66(10)
C9 C8 C3 109.15(9)
C9 C8 C7 112.23(10)
C3 C8 C7 111.96(9)
O1 C9 C8 113.26(9)
N1 C10 C2 177.62(12)
C1 O1 C9 121.47(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2061(13)
C1 O1 1.3281(14)
C1 C2 1.5241(15)
C2 C10 1.4661(15)
C2 C3 1.5391(13)
C3 C4 1.5234(16)
C3 C8 1.5278(15)
C4 C5 1.5034(17)
C5 C6 1.3224(18)
C6 C7 1.4935(19)
C7 C8 1.5347(16)
C8 C9 1.5042(18)
C9 O1 1.4633(15)
C10 N1 1.1412(16)
