#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/19/1511974.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_1511974
loop_
_publ_author_name
'Liu, Renrong'
'Zhang, Junliang'
_publ_section_title
;
 Organocatalytic Michael Addition of Indoles to
 Isatylidene-3-acetaldehydes: Application to the Formal Total Synthesis of
 (−)-Chimonanthine
;
_journal_issue                   9
_journal_name_full               'Organic Letters'
_journal_page_first              2266
_journal_paper_doi               10.1021/ol400845c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 104.708(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2349(8)
_cell_length_b                   18.662(2)
_cell_length_c                   10.0294(11)
_cell_measurement_temperature    296(2)
_cell_volume                     1309.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15038
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0342
_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)+(0.0482P)²+0.1948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                1881
_reflns_number_total             2309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400845c_si_003.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1511974
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
_atom_site_refinement_flags
N1 N 0.24682(15) 0.61880(6) 0.42313(11) 0.0469(3) Uani 1 1 d .
O1 O 0.26706(16) 0.70735(5) 0.58592(12) 0.0680(3) Uani 1 1 d .
O2 O 0.2938(2) 0.54665(8) 0.99903(12) 0.0913(4) Uani 1 1 d .
C1 C 0.24168(16) 0.54359(7) 0.42265(12) 0.0411(3) Uani 1 1 d .
C2 C 0.22410(19) 0.49812(8) 0.31230(13) 0.0515(3) Uani 1 1 d .
H2A H 0.2132 0.5157 0.2239 0.062 Uiso 1 1 calc R
C3 C 0.2232(2) 0.42519(8) 0.33763(15) 0.0563(4) Uani 1 1 d .
H3A H 0.2113 0.3933 0.2646 0.068 Uiso 1 1 calc R
C4 C 0.2394(2) 0.39859(8) 0.46831(15) 0.0553(4) Uani 1 1 d .
H4A H 0.2383 0.3494 0.4823 0.066 Uiso 1 1 calc R
C5 C 0.25736(19) 0.44460(7) 0.57828(14) 0.0488(3) Uani 1 1 d .
H5A H 0.2685 0.4266 0.6664 0.059 Uiso 1 1 calc R
C6 C 0.25868(16) 0.51797(7) 0.55672(12) 0.0398(3) Uani 1 1 d .
C7 C 0.27243(17) 0.58050(7) 0.64570(13) 0.0432(3) Uani 1 1 d .
C8 C 0.26257(18) 0.64464(7) 0.55280(14) 0.0479(3) Uani 1 1 d .
C9 C 0.2266(2) 0.66446(8) 0.30152(15) 0.0567(4) Uani 1 1 d .
H9A H 0.2925 0.6424 0.2390 0.068 Uiso 1 1 calc R
H9B H 0.2863 0.7105 0.3297 0.068 Uiso 1 1 calc R
C10 C 0.01989(19) 0.67602(7) 0.22716(13) 0.0492(3) Uani 1 1 d .
C11 C -0.0955(2) 0.71934(7) 0.28436(15) 0.0552(4) Uani 1 1 d .
H11A H -0.0435 0.7432 0.3668 0.066 Uiso 1 1 calc R
C12 C -0.2868(2) 0.72723(8) 0.21982(16) 0.0589(4) Uani 1 1 d .
H12A H -0.3631 0.7562 0.2592 0.071 Uiso 1 1 calc R
C13 C -0.3653(2) 0.69264(8) 0.09783(16) 0.0611(4) Uani 1 1 d .
H13A H -0.4946 0.6979 0.0550 0.073 Uiso 1 1 calc R
C14 C -0.2526(2) 0.65040(9) 0.03968(15) 0.0660(4) Uani 1 1 d .
H14A H -0.3052 0.6269 -0.0431 0.079 Uiso 1 1 calc R
C15 C -0.0603(2) 0.64243(9) 0.10355(15) 0.0611(4) Uani 1 1 d .
H15A H 0.0157 0.6141 0.0626 0.073 Uiso 1 1 calc R
C16 C 0.2860(2) 0.59066(8) 0.77996(14) 0.0530(4) Uani 1 1 d .
H16A H 0.2907 0.6378 0.8107 0.064 Uiso 1 1 calc R
C17 C 0.2938(3) 0.53534(10) 0.88085(15) 0.0685(4) Uani 1 1 d .
H17A H 0.2992 0.4880 0.8532 0.082 Uiso 1 1 calc R
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
C8 N1 C1 110.63(10)
C8 N1 C9 123.69(12)
C1 N1 C9 125.58(11)
C2 C1 C6 121.93(12)
C2 C1 N1 128.09(11)
C6 C1 N1 109.98(10)
C1 C2 C3 117.57(13)
C1 C2 H2A 121.2
C3 C2 H2A 121.2
C4 C3 C2 121.67(13)
C4 C3 H3A 119.2
C2 C3 H3A 119.2
C5 C4 C3 120.33(13)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C4 C5 C6 119.57(12)
C4 C5 H5A 120.2
C6 C5 H5A 120.2
C5 C6 C1 118.93(11)
C5 C6 C7 134.22(12)
C1 C6 C7 106.84(11)
C16 C7 C6 134.89(13)
C16 C7 C8 119.29(12)
C6 C7 C8 105.80(11)
O1 C8 N1 126.24(13)
O1 C8 C7 127.02(13)
N1 C8 C7 106.73(11)
N1 C9 C10 111.83(11)
N1 C9 H9A 109.3
C10 C9 H9A 109.3
N1 C9 H9B 109.3
C10 C9 H9B 109.3
H9A C9 H9B 107.9
C15 C10 C11 118.49(13)
C15 C10 C9 121.19(13)
C11 C10 C9 120.29(13)
C12 C11 C10 120.39(14)
C12 C11 H11A 119.8
C10 C11 H11A 119.8
C13 C12 C11 120.50(14)
C13 C12 H12A 119.7
C11 C12 H12A 119.7
C14 C13 C12 119.63(15)
C14 C13 H13A 120.2
C12 C13 H13A 120.2
C13 C14 C15 120.21(15)
C13 C14 H14A 119.9
C15 C14 H14A 119.9
C10 C15 C14 120.76(14)
C10 C15 H15A 119.6
C14 C15 H15A 119.6
C7 C16 C17 125.91(14)
C7 C16 H16A 117.0
C17 C16 H16A 117.0
O2 C17 C16 123.89(16)
O2 C17 H17A 118.1
C16 C17 H17A 118.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.3644(17)
N1 C1 1.4040(17)
N1 C9 1.4644(16)
O1 C8 1.2146(16)
O2 C17 1.2040(18)
C1 C2 1.3747(18)
C1 C6 1.4028(16)
C2 C3 1.385(2)
C2 H2A 0.9300
C3 C4 1.378(2)
C3 H3A 0.9300
C4 C5 1.3775(19)
C4 H4A 0.9300
C5 C6 1.3866(18)
C5 H5A 0.9300
C6 C7 1.4572(17)
C7 C16 1.3386(19)
C7 C8 1.5074(19)
C9 C10 1.5079(19)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C15 1.379(2)
C10 C11 1.386(2)
C11 C12 1.379(2)
C11 H11A 0.9300
C12 C13 1.372(2)
C12 H12A 0.9300
C13 C14 1.367(2)
C13 H13A 0.9300
C14 C15 1.384(2)
C14 H14A 0.9300
C15 H15A 0.9300
C16 C17 1.437(2)
C16 H16A 0.9300
C17 H17A 0.9300
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
C8 N1 C1 C2 179.02(12)
C9 N1 C1 C2 2.5(2)
C8 N1 C1 C6 -1.32(14)
C9 N1 C1 C6 -177.85(11)
C6 C1 C2 C3 0.16(19)
N1 C1 C2 C3 179.78(12)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 0.0(2)
C3 C4 C5 C6 0.1(2)
C4 C5 C6 C1 -0.03(18)
C4 C5 C6 C7 179.11(13)
C2 C1 C6 C5 -0.11(18)
N1 C1 C6 C5 -179.79(11)
C2 C1 C6 C7 -179.46(11)
N1 C1 C6 C7 0.85(13)
C5 C6 C7 C16 -1.2(3)
C1 C6 C7 C16 178.02(14)
C5 C6 C7 C8 -179.35(14)
C1 C6 C7 C8 -0.14(12)
C1 N1 C8 O1 -178.62(13)
C9 N1 C8 O1 -2.0(2)
C1 N1 C8 C7 1.18(13)
C9 N1 C8 C7 177.78(11)
C16 C7 C8 O1 0.7(2)
C6 C7 C8 O1 179.16(13)
C16 C7 C8 N1 -179.13(11)
C6 C7 C8 N1 -0.63(13)
C8 N1 C9 C10 -93.48(15)
C1 N1 C9 C10 82.61(16)
N1 C9 C10 C15 -106.23(15)
N1 C9 C10 C11 71.84(16)
C15 C10 C11 C12 1.3(2)
C9 C10 C11 C12 -176.86(12)
C10 C11 C12 C13 -0.3(2)
C11 C12 C13 C14 -0.4(2)
C12 C13 C14 C15 0.1(2)
C11 C10 C15 C14 -1.5(2)
C9 C10 C15 C14 176.60(13)
C13 C14 C15 C10 0.8(2)
C6 C7 C16 C17 1.1(3)
C8 C7 C16 C17 179.03(13)
C7 C16 C17 O2 -175.10(16)
