#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/49/1504911.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_1504911
loop_
_publ_author_name
'Kise, Naoki'
'Mano, Toshiyuki'
'Sakurai, Toshihiko'
_publ_section_title
;
 Electroreductive intramolecular coupling of 1-indolealkanones.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4617
_journal_page_last               4620
_journal_paper_doi               10.1021/ol801876k
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H18 Cl N O'
_chemical_formula_sum            'C13 H18 Cl N O'
_chemical_formula_weight         239.73
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_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                   8.0180(5)
_cell_length_b                   10.5735(8)
_cell_length_c                   14.6209(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1239.54(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12168
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.9447
_exptl_absorpt_correction_T_min  0.8937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.94(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0329
_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)+(0.0400P)²+0.1233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0757
_reflns_number_gt                2463
_reflns_number_total             2825
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801876k_si_003.cif
_cod_data_source_block           5HCl
_cod_database_code               1504911
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.20040(15) 0.18663(12) 0.82444(8) 0.0325(3) Uani 1 1 d .
H1 H 0.098(3) 0.2038(18) 0.8156(13) 0.053(5) Uiso 1 1 d .
C1 C 0.22559(18) 0.06838(16) 0.87576(10) 0.0351(4) Uani 1 1 d .
C2 C 0.1555(2) -0.04656(17) 0.85561(12) 0.0433(4) Uani 1 1 d .
H2 H 0.0793 -0.0558 0.8081 0.052 Uiso 1 1 calc R
C3 C 0.2034(2) -0.14830(19) 0.90931(13) 0.0495(4) Uani 1 1 d .
H3 H 0.1579 -0.2279 0.8986 0.059 Uiso 1 1 calc R
C4 C 0.3186(3) -0.13200(18) 0.97896(12) 0.0501(4) Uani 1 1 d .
H4 H 0.3491 -0.2013 1.0144 0.060 Uiso 1 1 calc R
C5 C 0.3892(2) -0.01613(19) 0.99706(12) 0.0475(4) Uani 1 1 d .
H5 H 0.4663 -0.0070 1.0441 0.057 Uiso 1 1 calc R
C6 C 0.34323(18) 0.08683(16) 0.94400(10) 0.0370(3) Uani 1 1 d .
C7 C 0.4032(2) 0.22081(17) 0.94337(10) 0.0400(4) Uani 1 1 d .
H6 H 0.5104 0.2281 0.9131 0.048 Uiso 1 1 calc R
H7 H 0.4122 0.2542 1.0050 0.048 Uiso 1 1 calc R
C8 C 0.26603(18) 0.28826(16) 0.88926(10) 0.0334(3) Uani 1 1 d .
H8 H 0.1760 0.3062 0.9327 0.040 Uiso 1 1 calc R
C9 C 0.30672(19) 0.41302(16) 0.84182(10) 0.0361(3) Uani 1 1 d .
O1 O 0.14673(12) 0.46639(11) 0.82126(8) 0.0427(3) Uani 1 1 d .
H9 H 0.1584 0.5267 0.7866 0.064 Uiso 1 1 calc R
C10 C 0.3995(2) 0.49887(19) 0.90856(13) 0.0536(5) Uani 1 1 d .
H10 H 0.4047 0.5830 0.8840 0.080 Uiso 1 1 calc R
H11 H 0.5105 0.4673 0.9176 0.080 Uiso 1 1 calc R
H12 H 0.3415 0.5003 0.9660 0.080 Uiso 1 1 calc R
C11 C 0.4043(2) 0.39371(17) 0.75331(11) 0.0427(4) Uani 1 1 d .
H13 H 0.4203 0.4746 0.7233 0.051 Uiso 1 1 calc R
H14 H 0.5133 0.3590 0.7673 0.051 Uiso 1 1 calc R
C12 C 0.3123(2) 0.30453(17) 0.68935(11) 0.0437(4) Uani 1 1 d .
H15 H 0.2041 0.3398 0.6743 0.052 Uiso 1 1 calc R
H16 H 0.3751 0.2949 0.6331 0.052 Uiso 1 1 calc R
C13 C 0.2902(2) 0.17780(17) 0.73398(10) 0.0439(4) Uani 1 1 d .
H17 H 0.3989 0.1397 0.7436 0.053 Uiso 1 1 calc R
H18 H 0.2276 0.1231 0.6933 0.053 Uiso 1 1 calc R
Cl1 Cl -0.17957(5) 0.19468(5) 0.81279(3) 0.05038(13) 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C13 109.20(12)
C1 N1 C8 103.54(11)
C13 N1 C8 115.04(12)
C1 N1 H1 113.0(14)
C13 N1 H1 109.9(13)
C8 N1 H1 106.1(13)
C2 C1 C6 123.93(15)
C2 C1 N1 125.94(13)
C6 C1 N1 109.91(14)
C1 C2 C3 116.91(16)
C1 C2 H2 121.5
C3 C2 H2 121.5
C4 C3 C2 120.29(18)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 121.77(17)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 118.85(16)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 118.22(16)
C5 C6 C7 131.41(15)
C1 C6 C7 110.32(14)
C6 C7 C8 102.32(13)
C6 C7 H6 111.3
C8 C7 H6 111.3
C6 C7 H7 111.3
C8 C7 H7 111.3
H6 C7 H7 109.2
C9 C8 N1 113.59(12)
C9 C8 C7 118.95(13)
N1 C8 C7 103.92(13)
C9 C8 H8 106.5
N1 C8 H8 106.5
C7 C8 H8 106.5
O1 C9 C8 104.14(12)
O1 C9 C11 109.49(13)
C8 C9 C11 112.30(14)
O1 C9 C10 109.63(14)
C8 C9 C10 109.14(13)
C11 C9 C10 111.84(14)
C9 O1 H9 109.5
C9 C10 H10 109.5
C9 C10 H11 109.5
H10 C10 H11 109.5
C9 C10 H12 109.5
H10 C10 H12 109.5
H11 C10 H12 109.5
C12 C11 C9 110.88(13)
C12 C11 H13 109.5
C9 C11 H13 109.5
C12 C11 H14 109.5
C9 C11 H14 109.5
H13 C11 H14 108.1
C13 C12 C11 110.11(14)
C13 C12 H15 109.6
C11 C12 H15 109.6
C13 C12 H16 109.6
C11 C12 H16 109.6
H15 C12 H16 108.2
C12 C13 N1 112.47(13)
C12 C13 H17 109.1
N1 C13 H17 109.1
C12 C13 H18 109.1
N1 C13 H18 109.1
H17 C13 H18 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.472(2)
N1 C13 1.509(2)
N1 C8 1.526(2)
N1 H1 0.85(2)
C1 C2 1.371(2)
C1 C6 1.387(2)
C2 C3 1.386(3)
C2 H2 0.9300
C3 C4 1.386(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.387(2)
C5 H5 0.9300
C6 C7 1.496(2)
C7 C8 1.531(2)
C7 H6 0.9700
C7 H7 0.9700
C8 C9 1.526(2)
C8 H8 0.9800
C9 O1 1.4333(18)
C9 C11 1.526(2)
C9 C10 1.526(2)
O1 H9 0.8200
C10 H10 0.9600
C10 H11 0.9600
C10 H12 0.9600
C11 C12 1.519(2)
C11 H13 0.9700
C11 H14 0.9700
C12 C13 1.501(2)
C12 H15 0.9700
C12 H16 0.9700
C13 H17 0.9700
C13 H18 0.9700
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
C13 N1 C1 C2 -71.67(19)
C8 N1 C1 C2 165.32(15)
C13 N1 C1 C6 103.20(15)
C8 N1 C1 C6 -19.82(15)
C6 C1 C2 C3 1.9(2)
N1 C1 C2 C3 176.11(15)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 -0.2(3)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C1 1.0(2)
C4 C5 C6 C7 -176.26(18)
C2 C1 C6 C5 -2.1(2)
N1 C1 C6 C5 -177.09(14)
C2 C1 C6 C7 175.75(15)
N1 C1 C6 C7 0.76(17)
C5 C6 C7 C8 -164.06(17)
C1 C6 C7 C8 18.47(16)
C1 N1 C8 C9 161.13(12)
C13 N1 C8 C9 42.06(17)
C1 N1 C8 C7 30.40(13)
C13 N1 C8 C7 -88.66(15)
C6 C7 C8 C9 -157.01(13)
C6 C7 C8 N1 -29.55(14)
N1 C8 C9 O1 73.03(14)
C7 C8 C9 O1 -164.19(13)
N1 C8 C9 C11 -45.35(17)
C7 C8 C9 C11 77.44(17)
N1 C8 C9 C10 -169.96(13)
C7 C8 C9 C10 -47.17(18)
O1 C9 C11 C12 -60.17(18)
C8 C9 C11 C12 55.00(18)
C10 C9 C11 C12 178.10(15)
C9 C11 C12 C13 -60.48(18)
C11 C12 C13 N1 56.59(18)
C1 N1 C13 C12 -163.79(13)
C8 N1 C13 C12 -47.92(18)
