#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:32:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178786 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/40/4104008.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_4104008
loop_
_publ_author_name
'K. C. Nicolaou'
'Arkady Krasovskiy'
'Utpal Majumder'
'Vincent É. Trépanier'
'David Y.-K. Chen'
_publ_contact_author_email       arkady@scripps.edu
_publ_contact_author_name        'Arkady Krasovskiy'
_publ_section_title
;
 New Synthetic Technologies for the Construction of Heterocycles and
 Tryptamines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3690
_journal_page_last               3699
_journal_paper_doi               10.1021/ja808692j
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_sum            'C17 H22 N2 O4'
_chemical_formula_weight         318.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.040(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9100(9)
_cell_length_b                   10.5400(5)
_cell_length_c                   17.1400(12)
_cell_measurement_temperature    113(2)
_cell_volume                     1720.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.880
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37340
_diffrn_reflns_theta_full        35.81
_diffrn_reflns_theta_max         35.81
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9741
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0092(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         7092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          3.636
_refine_ls_shift/su_mean         0.116
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0753P)²+0.2977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                4776
_reflns_number_total             7092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808692j_si_004.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4104008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
O1 O 0.43805(11) 0.51398(9) 0.39881(5) 0.0311(3) Uani 1.000(13) 1 d
O2 O 0.49509(10) 0.36463(9) 0.32328(5) 0.0287(3) Uani 1.000(13) 1 d
O3 O 0.09146(11) 0.34446(11) 0.18731(6) 0.0399(4) Uani 1.000(13) 1 d
O4 O 0.17204(11) 0.31019(9) 0.32355(6) 0.0324(3) Uani 1.000(13) 1 d
N1 N 0.54931(13) 0.33899(11) 0.46209(7) 0.0302(4) Uani 1.000(14) 1 d
N2 N 0.26711(13) 0.20360(12) 0.23925(7) 0.0320(4) Uani 1.000(13) 1 d
C1 C 0.73173(17) 0.19166(15) 0.53160(9) 0.0394(5) Uani 1.000(15) 1 d
C2 C 0.81895(18) 0.09055(16) 0.52792(10) 0.0441(6) Uani 1.000(15) 1 d
C3 C 0.81428(17) 0.03468(16) 0.45350(10) 0.0419(6) Uani 1.000(15) 1 d
C4 C 0.72124(15) 0.08057(14) 0.38269(9) 0.0342(5) Uani 1.000(15) 1 d
C5 C 0.63150(14) 0.18030(13) 0.38575(8) 0.0307(4) Uani 1.000(14) 1 d
C6 C 0.63838(14) 0.23580(13) 0.46052(8) 0.0304(4) Uani 1.000(14) 1 d
C7 C 0.49077(14) 0.41026(12) 0.39581(7) 0.0259(4) Uani 1.000(14) 1 d
C8 C 0.51820(14) 0.22831(12) 0.31342(8) 0.0274(4) Uani 1.000(14) 1 d
C9 C 0.55402(16) 0.22007(15) 0.23245(8) 0.0331(5) Uani 1.000(15) 1 d
C10 C 0.43124(16) 0.26099(15) 0.16134(8) 0.0350(5) Uani 1.000(15) 1 d
C11 C 0.29839(16) 0.18886(17) 0.16086(9) 0.0373(5) Uani 1.000(16) 1 d
C12 C 0.37931(14) 0.15958(13) 0.30826(8) 0.0295(4) Uani 1.000(15) 1 d
C13 C 0.17056(14) 0.29192(13) 0.24559(8) 0.0290(4) Uani 1.000(14) 1 d
C14 C 0.07049(16) 0.39728(15) 0.34445(10) 0.0392(5) Uani 1.000(14) 1 d
C15 C -0.07788(19) 0.3460(2) 0.30999(14) 0.0514(8) Uani 1.000(18) 1 d
C16 C 0.0853(2) 0.53061(16) 0.31499(13) 0.0461(7) Uani 1.000(17) 1 d
C17 C 0.1168(3) 0.3908(2) 0.43654(12) 0.0571(9) Uani 1.000(18) 1 d
H1 H 0.7340(19) 0.2351(17) 0.5851(11) 0.041(5) Uiso 1 1 d
H2 H 0.885(2) 0.0593(18) 0.5791(13) 0.049(5) Uiso 1 1 d
H3 H 0.8783(19) -0.0376(17) 0.4489(10) 0.038(5) Uiso 1 1 d
H4 H 0.7214(19) 0.0408(16) 0.3301(11) 0.040(5) Uiso 1 1 d
H5 H 0.5554(19) 0.3788(17) 0.5090(12) 0.037(5) Uiso 1 1 d
H6 H 0.639(2) 0.2731(18) 0.2358(11) 0.045(5) Uiso 1 1 d
H7 H 0.5772(18) 0.1301(17) 0.2249(10) 0.031(4) Uiso 1 1 d
H8 H 0.4142(18) 0.3515(17) 0.1642(10) 0.032(4) Uiso 1 1 d
H9 H 0.4546(19) 0.2459(17) 0.1090(12) 0.044(5) Uiso 1 1 d
H10 H 0.217(2) 0.2205(17) 0.1178(12) 0.046(5) Uiso 1 1 d
H11 H 0.3093(19) 0.0994(19) 0.1532(11) 0.040(5) Uiso 1 1 d
H12 H 0.3518(18) 0.1722(15) 0.3597(11) 0.033(4) Uiso 1 1 d
H13 H 0.3961(16) 0.0674(16) 0.3007(9) 0.028(4) Uiso 1 1 d
H14 H -0.106(2) 0.343(2) 0.2485(15) 0.059(6) Uiso 1 1 d
H15 H -0.085(2) 0.259(2) 0.3303(13) 0.060(6) Uiso 1 1 d
H16 H -0.142(2) 0.400(2) 0.3292(13) 0.059(6) Uiso 1 1 d
H17 H 0.052(3) 0.444(2) 0.4560(14) 0.066(7) Uiso 1 1 d
H18 H 0.106(2) 0.305(2) 0.4538(14) 0.063(7) Uiso 1 1 d
H19 H 0.218(3) 0.425(2) 0.4568(14) 0.071(7) Uiso 1 1 d
H20 H 0.048(2) 0.540(2) 0.2574(16) 0.063(6) Uiso 1 1 d
H21 H 0.033(3) 0.590(2) 0.3407(14) 0.072(7) Uiso 1 1 d
H22 H 0.187(2) 0.5561(19) 0.3319(12) 0.056(6) Uiso 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
C7 O2 C8 120.06(10)
C13 O4 C14 120.55(11)
C7 N1 C6 122.67(11)
C13 N2 C12 123.27(11)
C13 N2 C11 118.45(12)
C12 N2 C11 113.73(11)
C2 C1 C6 119.35(14)
C1 C2 C3 120.24(15)
C4 C3 C2 119.83(14)
C5 C4 C3 120.49(14)
C4 C5 C6 118.95(13)
C4 C5 C8 124.16(12)
C6 C5 C8 116.76(12)
C1 C6 C5 121.13(13)
C1 C6 N1 120.75(12)
C5 C6 N1 118.11(12)
O1 C7 O2 118.90(11)
O1 C7 N1 123.53(11)
O2 C7 N1 117.54(11)
O2 C8 C5 109.66(10)
O2 C8 C9 104.03(11)
C5 C8 C9 114.82(11)
O2 C8 C12 107.55(10)
C5 C8 C12 109.88(11)
C9 C8 C12 110.51(11)
C8 C9 C10 112.04(12)
C11 C10 C9 111.18(13)
N2 C11 C10 110.12(11)
N2 C12 C8 111.54(11)
O3 C13 O4 125.21(13)
O3 C13 N2 123.53(13)
O4 C13 N2 111.23(11)
O4 C14 C16 111.13(13)
O4 C14 C17 101.15(13)
C16 C14 C17 111.04(16)
O4 C14 C15 109.53(13)
C16 C14 C15 111.85(15)
C17 C14 C15 111.66(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2189(15)
O2 C7 1.3446(15)
O2 C8 1.4719(15)
O3 C13 1.2192(16)
O4 C13 1.3460(16)
O4 C14 1.4775(17)
N1 C7 1.3517(17)
N1 C6 1.4056(18)
N2 C13 1.3607(18)
N2 C12 1.4573(18)
N2 C11 1.4682(18)
C1 C2 1.385(2)
C1 C6 1.391(2)
C2 C3 1.394(2)
C3 C4 1.392(2)
C4 C5 1.387(2)
C5 C6 1.3933(18)
C5 C8 1.5114(19)
C8 C9 1.5270(19)
C8 C12 1.5362(19)
C9 C10 1.527(2)
C10 C11 1.518(2)
C14 C16 1.514(3)
C14 C17 1.519(3)
C14 C15 1.524(2)
