#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:20:51 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178946 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/75/4117592.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_4117592
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            'C19 H21 N O4'
_chemical_formula_weight         327.37
_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                   6.7608(3)
_cell_length_b                   11.1455(4)
_cell_length_c                   21.7524(9)
_cell_measurement_temperature    143(1)
_cell_volume                     1639.10(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35637
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0327P)²+0.3291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0638
_reflns_number_gt                2799
_reflns_number_total             2907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211840k_si_005.cif
_cod_data_source_block           UP1325-Cmpd(+)-19
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4117592
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 0.6277(2) 0.72256(12) 0.69488(6) 0.0269(3) Uani 1 1 d .
H1A H 0.7237 0.7515 0.7245 0.036 Uiso 1 1 calc R
H1B H 0.6723 0.6452 0.6799 0.036 Uiso 1 1 calc R
C2 C 0.6142(2) 0.80923(12) 0.64214(6) 0.0263(3) Uani 1 1 d .
C3 C 0.4543(2) 0.77819(11) 0.59588(6) 0.0254(3) Uani 1 1 d .
H3 H 0.4568 0.8352 0.5616 0.034 Uiso 1 1 calc R
C4 C 0.2585(2) 0.78880(11) 0.63103(6) 0.0261(3) Uani 1 1 d .
H4A H 0.1481 0.7781 0.6031 0.035 Uiso 1 1 calc R
H4B H 0.2478 0.8677 0.6496 0.035 Uiso 1 1 calc R
C5 C 0.25339(19) 0.69192(11) 0.68106(6) 0.0224(3) Uani 1 1 d .
H5 H 0.1295 0.7011 0.7039 0.030 Uiso 1 1 calc R
C6 C 0.4244(2) 0.70831(11) 0.72642(6) 0.0239(3) Uani 1 1 d .
H6 H 0.3988 0.7813 0.7502 0.032 Uiso 1 1 calc R
C7 C 0.4256(2) 0.60418(12) 0.77027(6) 0.0274(3) Uani 1 1 d .
H7A H 0.5258 0.6171 0.8015 0.037 Uiso 1 1 calc R
H7B H 0.2982 0.5987 0.7906 0.037 Uiso 1 1 calc R
C8 C 0.39796(18) 0.47561(11) 0.68073(6) 0.0213(3) Uani 1 1 d .
C9 C 0.25344(18) 0.56482(11) 0.65143(6) 0.0209(3) Uani 1 1 d .
C10 C 0.3044(2) 0.57367(11) 0.58242(6) 0.0231(3) Uani 1 1 d .
H10A H 0.3363 0.4945 0.5668 0.031 Uiso 1 1 calc R
H10B H 0.1904 0.6033 0.5600 0.031 Uiso 1 1 calc R
C11 C 0.04698(19) 0.50532(12) 0.65601(6) 0.0278(3) Uani 1 1 d .
H11A H -0.0495 0.5596 0.6383 0.037 Uiso 1 1 calc R
H11B H 0.0478 0.4332 0.6311 0.037 Uiso 1 1 calc R
C12 C -0.0217(2) 0.47180(15) 0.72051(7) 0.0385(4) Uani 1 1 d .
H12A H 0.0721 0.4179 0.7388 0.058 Uiso 1 1 calc R
H12B H -0.1486 0.4334 0.7182 0.058 Uiso 1 1 calc R
H12C H -0.0319 0.5430 0.7452 0.058 Uiso 1 1 calc R
C13 C 0.6388(2) 0.62671(11) 0.54088(6) 0.0245(3) Uani 1 1 d .
C14 C 0.6424(2) 0.51710(11) 0.50083(6) 0.0249(3) Uani 1 1 d .
C15 C 0.8104(2) 0.44508(14) 0.50012(7) 0.0346(3) Uani 1 1 d .
H15 H 0.9133 0.4605 0.5274 0.046 Uiso 1 1 calc R
C16 C 0.8253(2) 0.35061(14) 0.45908(7) 0.0413(4) Uani 1 1 d .
H16 H 0.9369 0.3018 0.4593 0.055 Uiso 1 1 calc R
C17 C 0.6751(3) 0.32886(13) 0.41790(7) 0.0410(4) Uani 1 1 d .
H17 H 0.6854 0.2656 0.3902 0.055 Uiso 1 1 calc R
C18 C 0.5095(2) 0.40069(13) 0.41762(7) 0.0376(3) Uani 1 1 d .
H18 H 0.4087 0.3861 0.3895 0.050 Uiso 1 1 calc R
C19 C 0.4922(2) 0.49467(12) 0.45899(6) 0.0298(3) Uani 1 1 d .
H19 H 0.3797 0.5427 0.4587 0.040 Uiso 1 1 calc R
N1 N 0.47210(16) 0.65399(9) 0.57251(5) 0.0224(2) Uani 1 1 d .
O1 O 0.70501(17) 0.90235(9) 0.63988(5) 0.0373(3) Uani 1 1 d .
O2 O 0.46612(14) 0.49276(8) 0.73805(4) 0.0251(2) Uani 1 1 d .
O3 O 0.44762(15) 0.38489(8) 0.65485(4) 0.0311(2) Uani 1 1 d .
O4 O 0.78411(15) 0.69326(9) 0.54334(4) 0.0334(2) 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
C2 C1 C6 110.56(11)
O1 C2 C1 123.58(13)
O1 C2 C3 122.11(13)
C1 C2 C3 113.78(11)
N1 C3 C2 112.53(11)
N1 C3 C4 108.29(10)
C2 C3 C4 105.48(10)
C3 C4 C5 108.61(11)
C6 C5 C4 110.88(11)
C6 C5 C9 112.04(10)
C4 C5 C9 110.30(10)
C7 C6 C5 108.73(10)
C7 C6 C1 110.90(11)
C5 C6 C1 113.47(10)
O2 C7 C6 110.81(10)
O3 C8 O2 117.23(11)
O3 C8 C9 121.85(11)
O2 C8 C9 120.83(11)
C8 C9 C10 107.67(10)
C8 C9 C11 105.67(10)
C10 C9 C11 106.93(10)
C8 C9 C5 114.73(10)
C10 C9 C5 110.17(10)
C11 C9 C5 111.28(10)
N1 C10 C9 110.87(10)
C12 C11 C9 116.02(11)
O4 C13 N1 120.41(11)
O4 C13 C14 120.17(12)
N1 C13 C14 119.38(11)
C19 C14 C15 119.14(12)
C19 C14 C13 121.08(12)
C15 C14 C13 119.28(12)
C16 C15 C14 120.34(14)
C17 C16 C15 120.03(14)
C16 C17 C18 120.05(13)
C17 C18 C19 120.36(14)
C14 C19 C18 120.06(13)
C13 N1 C10 125.67(10)
C13 N1 C3 116.88(10)
C10 N1 C3 117.35(10)
C8 O2 C7 120.34(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5025(19)
C1 C6 1.5443(19)
C2 O1 1.2069(16)
C2 C3 1.5172(19)
C3 N1 1.4796(16)
C3 C4 1.5333(19)
C4 C5 1.5335(17)
C5 C6 1.5309(18)
C5 C9 1.5563(16)
C6 C7 1.5023(18)
C7 O2 1.4520(15)
C8 O3 1.2050(16)
C8 O2 1.3429(15)
C8 C9 1.5328(17)
C9 C10 1.5433(17)
C9 C11 1.5486(17)
C10 N1 1.4605(16)
C11 C12 1.524(2)
C13 O4 1.2321(16)
C13 N1 1.3550(17)
C13 C14 1.5008(18)
C14 C19 1.3860(19)
C14 C15 1.391(2)
C15 C16 1.384(2)
C16 C17 1.376(2)
C17 C18 1.376(2)
C18 C19 1.386(2)
