#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113126.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_4113126
loop_
_publ_author_name
'Audris Huang'
'Jeremy J. Kodanko'
'Larry E. Overman'
_publ_section_title
;
 Asymmetric Synthesis of Pyrrolidinoindolines. Application for the
 Practical Total Synthesis of (-)-Phenserine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14043
_journal_page_last               14053
_journal_paper_doi               10.1021/ja046690e
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C18 H19 I N2'
_chemical_formula_weight         390.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 114.4590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5099(4)
_cell_length_b                   9.5868(4)
_cell_length_c                   9.5449(4)
_cell_measurement_temperature    173(2)
_cell_volume                     792.11(6)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8267
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    2.017
_exptl_absorpt_correction_T_max  0.7655
_exptl_absorpt_correction_T_min  0.5558
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(12)
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0154
_refine_ls_R_factor_gt           0.0151
_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)+(0.0182P)²+0.1467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0386
_reflns_number_gt                3503
_reflns_number_total             3551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja046690esi20040617_081035_1.cif
_cod_data_source_block           compound61
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4113126
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
I1 I -0.488379(11) 0.46510(2) 0.373999(11) 0.02132(5) Uani 1 1 d
N1 N -0.4667(2) 0.74616(19) 0.16105(19) 0.0172(3) Uani 1 1 d
N2 N -0.57110(16) 0.9703(3) 0.02708(15) 0.0180(3) Uani 1 1 d
C1 C -0.4402(2) 0.8740(2) 0.0877(2) 0.0156(4) Uani 1 1 d
C2 C -0.31332(18) 0.9589(3) 0.22089(17) 0.0161(3) Uani 1 1 d
C3 C -0.2714(2) 0.8629(2) 0.3582(2) 0.0158(4) Uani 1 1 d
C4 C -0.1668(2) 0.8852(2) 0.5081(2) 0.0195(4) Uani 1 1 d
C5 C -0.1522(2) 0.7852(2) 0.6198(2) 0.0216(4) Uani 1 1 d
C6 C -0.2425(2) 0.6660(2) 0.5795(2) 0.0202(4) Uani 1 1 d
C7 C -0.3490(2) 0.6439(2) 0.4277(2) 0.0175(4) Uani 1 1 d
C8 C -0.3639(2) 0.7437(2) 0.3159(2) 0.0160(4) Uani 1 1 d
C9 C -0.5694(2) 1.0452(2) 0.1621(2) 0.0206(4) Uani 1 1 d
C10 C -0.4013(3) 1.0876(2) 0.2407(2) 0.0208(4) Uani 1 1 d
C11 C -0.7202(3) 0.9112(3) -0.0725(3) 0.0241(4) Uani 1 1 d
C12 C -0.1744(2) 1.00240(19) 0.1863(2) 0.0188(4) Uani 1 1 d
C13 C -0.0741(2) 0.8834(2) 0.1773(2) 0.0178(4) Uani 1 1 d
C14 C 0.0550(2) 0.8409(2) 0.3070(2) 0.0216(4) Uani 1 1 d
C15 C 0.1456(3) 0.7307(2) 0.2996(2) 0.0240(4) Uani 1 1 d
C16 C 0.1079(3) 0.6580(2) 0.1630(3) 0.0234(4) Uani 1 1 d
C17 C -0.0196(2) 0.6990(2) 0.0331(2) 0.0212(4) Uani 1 1 d
C18 C -0.1086(2) 0.8119(2) 0.0395(2) 0.0194(4) Uani 1 1 d
H1 H -0.475(3) 0.672(3) 0.113(3) 0.021(6) Uiso 1 1 d
H1A H -0.407(3) 0.851(2) 0.008(3) 0.011(5) Uiso 1 1 d
H4 H -0.111(2) 0.976(4) 0.531(2) 0.025(5) Uiso 1 1 d
H5 H -0.080(3) 0.804(3) 0.726(3) 0.028(7) Uiso 1 1 d
H6 H -0.227(3) 0.594(3) 0.655(3) 0.021(6) Uiso 1 1 d
H9A H -0.607(2) 0.984(3) 0.225(2) 0.020(6) Uiso 1 1 d
H9B H -0.636(3) 1.112(3) 0.138(3) 0.022(6) Uiso 1 1 d
H10A H -0.364(3) 1.112(3) 0.344(3) 0.017(6) Uiso 1 1 d
H10B H -0.388(3) 1.172(3) 0.179(3) 0.025(7) Uiso 1 1 d
H11A H -0.794(3) 0.975(4) -0.101(3) 0.034(7) Uiso 1 1 d
H11B H -0.724(4) 0.867(3) -0.175(4) 0.039(8) Uiso 1 1 d
H11C H -0.751(4) 0.840(3) -0.016(3) 0.032(7) Uiso 1 1 d
H12A H -0.216(3) 1.054(3) 0.090(3) 0.019(6) Uiso 1 1 d
H12B H -0.115(3) 1.058(3) 0.254(3) 0.026(7) Uiso 1 1 d
H14 H 0.078(4) 0.888(4) 0.395(3) 0.043(8) Uiso 1 1 d
H15 H 0.229(3) 0.706(3) 0.387(3) 0.020(7) Uiso 1 1 d
H16 H 0.172(3) 0.591(3) 0.162(3) 0.028(7) Uiso 1 1 d
H17 H -0.048(3) 0.642(3) -0.063(3) 0.025(6) Uiso 1 1 d
H18 H -0.197(3) 0.842(3) -0.049(3) 0.018(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'
I I -0.4742 1.8119 '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
C8 N1 C1 109.43(17)
C11 N2 C1 116.8(2)
C11 N2 C9 114.67(15)
C1 N2 C9 105.24(14)
N2 C1 N1 115.13(17)
N2 C1 C2 103.62(18)
N1 C1 C2 105.65(17)
C3 C2 C10 109.93(14)
C3 C2 C12 114.02(15)
C10 C2 C12 111.4(2)
C3 C2 C1 103.0(2)
C10 C2 C1 103.87(14)
C12 C2 C1 113.90(15)
C4 C3 C8 121.64(18)
C4 C3 C2 128.4(2)
C8 C3 C2 109.81(18)
C3 C4 C5 119.05(19)
C6 C5 C4 120.00(19)
C5 C6 C7 120.89(19)
C8 C7 C6 119.24(19)
C8 C7 I1 121.31(14)
C6 C7 I1 119.41(15)
N1 C8 C7 128.79(19)
N1 C8 C3 111.96(17)
C7 C8 C3 119.19(18)
N2 C9 C10 101.08(15)
C9 C10 C2 103.81(17)
C13 C12 C2 115.08(18)
C14 C13 C18 118.02(19)
C14 C13 C12 120.89(18)
C18 C13 C12 121.09(19)
C15 C14 C13 121.0(2)
C14 C15 C16 120.5(2)
C17 C16 C15 119.2(2)
C16 C17 C18 120.34(19)
C17 C18 C13 120.88(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C7 2.096(2)
N1 C8 1.394(3)
N1 C1 1.484(3)
N2 C11 1.456(3)
N2 C1 1.463(3)
N2 C9 1.469(3)
C1 C2 1.570(3)
C2 C3 1.514(3)
C2 C10 1.546(3)
C2 C12 1.546(3)
C3 C4 1.380(3)
C3 C8 1.396(3)
C4 C5 1.398(3)
C5 C6 1.384(3)
C6 C7 1.398(3)
C7 C8 1.396(3)
C9 C10 1.513(3)
C12 C13 1.512(3)
C13 C14 1.395(3)
C13 C18 1.396(3)
C14 C15 1.383(3)
C15 C16 1.388(3)
C16 C17 1.385(3)
C17 C18 1.391(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C11 N2 C1 N1 -50.4(2)
C9 N2 C1 N1 78.1(2)
C11 N2 C1 C2 -165.24(15)
C9 N2 C1 C2 -36.7(2)
C8 N1 C1 N2 -117.70(18)
C8 N1 C1 C2 -4.0(2)
N2 C1 C2 C3 125.41(16)
N1 C1 C2 C3 3.97(19)
N2 C1 C2 C10 10.8(2)
N1 C1 C2 C10 -110.69(18)
N2 C1 C2 C12 -110.60(19)
N1 C1 C2 C12 127.96(19)
C10 C2 C3 C4 -68.7(2)
C12 C2 C3 C4 57.2(3)
C1 C2 C3 C4 -178.85(19)
C10 C2 C3 C8 107.5(2)
C12 C2 C3 C8 -126.6(2)
C1 C2 C3 C8 -2.7(2)
C8 C3 C4 C5 0.6(3)
C2 C3 C4 C5 176.29(19)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C7 -0.1(3)
C5 C6 C7 C8 0.1(3)
C5 C6 C7 I1 -177.88(16)
C1 N1 C8 C7 179.50(18)
C1 N1 C8 C3 2.4(2)
C6 C7 C8 N1 -176.61(19)
I1 C7 C8 N1 1.3(3)
C6 C7 C8 C3 0.3(3)
I1 C7 C8 C3 178.20(14)
C4 C3 C8 N1 176.77(18)
C2 C3 C8 N1 0.3(2)
C4 C3 C8 C7 -0.6(3)
C2 C3 C8 C7 -177.05(17)
C11 N2 C9 C10 178.2(2)
C1 N2 C9 C10 48.5(2)
N2 C9 C10 C2 -39.7(2)
C3 C2 C10 C9 -91.87(19)
C12 C2 C10 C9 140.76(16)
C1 C2 C10 C9 17.7(2)
C3 C2 C12 C13 50.4(3)
C10 C2 C12 C13 175.50(16)
C1 C2 C12 C13 -67.4(2)
C2 C12 C13 C14 -92.2(2)
C2 C12 C13 C18 87.2(2)
C18 C13 C14 C15 -0.3(3)
C12 C13 C14 C15 179.01(19)
C13 C14 C15 C16 -1.4(3)
C14 C15 C16 C17 1.5(3)
C15 C16 C17 C18 0.1(3)
C16 C17 C18 C13 -1.8(3)
C14 C13 C18 C17 1.9(3)
C12 C13 C18 C17 -177.42(18)
