#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508795.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_1508795
loop_
_publ_author_name
'Zhang, Li'
'Li, Zhiming'
'Fan, Renhua'
_publ_section_title
;
 1,2- and 1,4-Additions of 2-Alkynylcyclohexadienimines with Aromatic
 Amines To Access 4-Amino-N-arylindoles and -azepinoindoles.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6076
_journal_page_last               6079
_journal_paper_doi               10.1021/ol3029675
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C35 H30 Cl2 N2 O'
_chemical_formula_weight         565.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 116.640(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.121(7)
_cell_length_b                   9.598(2)
_cell_length_c                   23.181(6)
_cell_measurement_reflns_used    4374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.24
_cell_volume                     5592(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13226
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.1006
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2845
_refine_ls_wR_factor_ref         0.3115
_reflns_number_gt                3659
_reflns_number_total             4923
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3029675_si_002.cif
_cod_data_source_block           a11219b
_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_cell_volume        5593(2)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1508795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.55549(12) 1.0536(3) 0.49194(16) 0.0507(8) Uani 1 1 d .
N2 N 0.67386(12) 1.0631(3) 0.40221(14) 0.0480(7) Uani 1 1 d .
C1 C 0.57770(13) 0.9353(4) 0.53117(16) 0.0445(8) Uani 1 1 d .
C2 C 0.57890(15) 0.9313(4) 0.59156(18) 0.0545(9) Uani 1 1 d .
H2 H 0.5658 1.0067 0.6052 0.065 Uiso 1 1 calc R
C3 C 0.59896(18) 0.8188(5) 0.63154(19) 0.0630(11) Uani 1 1 d .
H3 H 0.5989 0.8190 0.6716 0.076 Uiso 1 1 calc R
C4 C 0.61935(16) 0.7046(4) 0.61343(19) 0.0592(10) Uani 1 1 d .
C5 C 0.61739(14) 0.7086(4) 0.55315(18) 0.0508(9) Uani 1 1 d .
H5 H 0.6306 0.6327 0.5398 0.061 Uiso 1 1 calc R
C6 C 0.59672(13) 0.8204(4) 0.51109(16) 0.0436(8) Uani 1 1 d .
C7 C 0.6434(2) 0.5821(5) 0.6577(2) 0.0893(16) Uani 1 1 d .
H7A H 0.6552 0.5143 0.6365 0.134 Uiso 1 1 calc R
H7B H 0.6172 0.5410 0.6683 0.134 Uiso 1 1 calc R
H7C H 0.6731 0.6130 0.6965 0.134 Uiso 1 1 calc R
C8 C 0.59513(13) 0.8112(3) 0.44476(16) 0.0438(8) Uani 1 1 d .
H8 H 0.6133 0.7251 0.4432 0.053 Uiso 1 1 calc R
C9 C 0.53901(15) 0.8038(4) 0.39232(18) 0.0532(9) Uani 1 1 d .
C13 C 0.62338(13) 0.9295(3) 0.43239(15) 0.0417(8) Uani 1 1 d .
C14 C 0.65895(13) 0.9266(3) 0.40687(16) 0.0433(8) Uani 1 1 d .
C15 C 0.67902(13) 0.8045(3) 0.38664(16) 0.0440(8) Uani 1 1 d .
C16 C 0.64303(15) 0.7053(4) 0.34661(17) 0.0500(9) Uani 1 1 d .
H16 H 0.6068 0.7195 0.3321 0.060 Uiso 1 1 calc R
C17 C 0.66018(17) 0.5875(4) 0.32828(19) 0.0590(10) Uani 1 1 d .
H17 H 0.6355 0.5232 0.3013 0.071 Uiso 1 1 calc R
C18 C 0.7132(2) 0.5636(5) 0.3492(3) 0.0740(13) Uani 1 1 d .
H18 H 0.7247 0.4834 0.3368 0.089 Uiso 1 1 calc R
C19 C 0.74978(19) 0.6607(5) 0.3893(3) 0.0764(13) Uani 1 1 d .
H19 H 0.7860 0.6448 0.4039 0.092 Uiso 1 1 calc R
C20 C 0.73302(16) 0.7795(4) 0.4075(2) 0.0631(11) Uani 1 1 d .
H20 H 0.7579 0.8439 0.4340 0.076 Uiso 1 1 calc R
C21 C 0.70837(13) 1.1106(4) 0.37613(16) 0.0450(8) Uani 1 1 d .
C22 C 0.69456(15) 1.0978(4) 0.31180(18) 0.0538(9) Uani 1 1 d .
H22 H 0.6633 1.0519 0.2848 0.065 Uiso 1 1 calc R
C23 C 0.72667(16) 1.1527(4) 0.28699(19) 0.0588(10) Uani 1 1 d .
H23 H 0.7169 1.1428 0.2432 0.071 Uiso 1 1 calc R
C24 C 0.77315(15) 1.2225(4) 0.3257(2) 0.0549(10) Uani 1 1 d .
C25 C 0.78664(16) 1.2314(5) 0.3903(2) 0.0646(11) Uani 1 1 d .
H25 H 0.8181 1.2757 0.4177 0.078 Uiso 1 1 calc R
C26 C 0.75489(16) 1.1767(5) 0.41549(19) 0.0609(10) Uani 1 1 d .
H26 H 0.7650 1.1845 0.4594 0.073 Uiso 1 1 calc R
C27 C 0.8072(2) 1.2868(5) 0.2981(3) 0.0827(15) Uani 1 1 d .
H27A H 0.7858 1.3465 0.2627 0.124 Uiso 1 1 calc R
H27B H 0.8226 1.2146 0.2831 0.124 Uiso 1 1 calc R
H27C H 0.8351 1.3404 0.3308 0.124 Uiso 1 1 calc R
C28 C 0.64622(14) 1.1525(4) 0.42295(16) 0.0457(8) Uani 1 1 d .
C29 C 0.61552(13) 1.0718(3) 0.44354(15) 0.0429(8) Uani 1 1 d .
C30 C 0.58286(13) 1.1358(4) 0.46693(16) 0.0456(8) Uani 1 1 d .
C31 C 0.57798(15) 1.2803(4) 0.46358(18) 0.0527(9) Uani 1 1 d .
C32 C 0.60848(16) 1.3563(4) 0.44055(19) 0.0568(10) Uani 1 1 d .
H32 H 0.6049 1.4528 0.4383 0.068 Uiso 1 1 calc R
C33 C 0.64313(17) 1.2969(4) 0.42124(19) 0.0561(10) Uani 1 1 d .
H33 H 0.6637 1.3507 0.4076 0.067 Uiso 1 1 calc R
C34 C 0.54170(19) 1.3539(5) 0.4856(2) 0.0713(12) Uani 1 1 d .
H34A H 0.5242 1.2864 0.5001 0.107 Uiso 1 1 calc R
H34B H 0.5155 1.4062 0.4504 0.107 Uiso 1 1 calc R
H34C H 0.5622 1.4160 0.5205 0.107 Uiso 1 1 calc R
O1 O 0.50892(16) 0.6977(5) 0.39467(19) 0.1130(15) Uani 1 1 d .
C10 C 0.51081(19) 0.8817(6) 0.3410(2) 0.0806(14) Uani 1 1 d .
H10A H 0.5223 0.9618 0.3285 0.097 Uiso 1 1 calc R
C11 C 0.4600(2) 0.8202(9) 0.3090(3) 0.102(2) Uani 1 1 d .
H11A H 0.4317 0.8520 0.2713 0.122 Uiso 1 1 calc R
C12 C 0.4603(3) 0.7159(10) 0.3404(4) 0.120(3) Uani 1 1 d .
H12A H 0.4314 0.6565 0.3291 0.144 Uiso 1 1 calc R
C35 C 1.0117(6) 0.7980(16) 0.2821(5) 0.221(6) Uani 1 1 d .
Cl1 Cl 0.94962(14) 0.7334(5) 0.2451(2) 0.244(2) Uani 1 1 d .
Cl2 Cl 0.9953(6) 0.9687(13) 0.2651(14) 0.85(2) Uani 1 1 d .
H1 H 0.5416(16) 1.098(4) 0.5053(19) 0.046(11) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C30 N1 C1 123.6(3) . .
C30 N1 H1 110(3) . .
C1 N1 H1 111(3) . .
C28 N2 C14 108.7(3) . .
C28 N2 C21 123.0(3) . .
C14 N2 C21 128.1(3) . .
C2 C1 C6 118.4(3) . .
C2 C1 N1 118.4(3) . .
C6 C1 N1 123.1(3) . .
C3 C2 C1 121.5(4) . .
C3 C2 H2 119.3 . .
C1 C2 H2 119.3 . .
C2 C3 C4 121.3(4) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C5 C4 C3 116.9(4) . .
C5 C4 C7 121.0(4) . .
C3 C4 C7 122.1(4) . .
C4 C5 C6 123.3(4) . .
C4 C5 H5 118.4 . .
C6 C5 H5 118.4 . .
C5 C6 C1 118.6(3) . .
C5 C6 C8 118.5(3) . .
C1 C6 C8 122.8(3) . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 109.8(3) . .
C13 C8 C6 112.0(3) . .
C9 C8 C6 111.4(3) . .
C13 C8 H8 107.8 . .
C9 C8 H8 107.8 . .
C6 C8 H8 107.8 . .
C10 C9 O1 109.3(4) . .
C10 C9 C8 133.6(4) . .
O1 C9 C8 117.1(4) . .
C14 C13 C29 107.5(3) . .
C14 C13 C8 128.6(3) . .
C29 C13 C8 123.9(3) . .
C13 C14 N2 108.5(3) . .
C13 C14 C15 127.9(3) . .
N2 C14 C15 123.6(3) . .
C20 C15 C16 117.8(3) . .
C20 C15 C14 122.9(3) . .
C16 C15 C14 119.3(3) . .
C17 C16 C15 121.2(4) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C18 C17 C16 120.6(4) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C17 C18 C19 119.2(4) . .
C17 C18 H18 120.4 . .
C19 C18 H18 120.4 . .
C20 C19 C18 120.7(4) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C15 120.6(4) . .
C19 C20 H20 119.7 . .
C15 C20 H20 119.7 . .
C22 C21 C26 119.2(3) . .
C22 C21 N2 121.2(3) . .
C26 C21 N2 119.5(3) . .
C21 C22 C23 120.2(3) . .
C21 C22 H22 119.9 . .
C23 C22 H22 119.9 . .
C22 C23 C24 121.4(4) . .
C22 C23 H23 119.3 . .
C24 C23 H23 119.3 . .
C25 C24 C23 117.2(3) . .
C25 C24 C27 121.5(4) . .
C23 C24 C27 121.3(4) . .
C24 C25 C26 121.7(4) . .
C24 C25 H25 119.1 . .
C26 C25 H25 119.1 . .
C21 C26 C25 120.2(4) . .
C21 C26 H26 119.9 . .
C25 C26 H26 119.9 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
N2 C28 C33 130.4(3) . .
N2 C28 C29 107.8(3) . .
C33 C28 C29 121.6(3) . .
C28 C29 C30 120.2(3) . .
C28 C29 C13 107.5(3) . .
C30 C29 C13 132.3(3) . .
C31 C30 N1 121.8(3) . .
C31 C30 C29 118.8(3) . .
N1 C30 C29 119.5(3) . .
C30 C31 C32 118.5(3) . .
C30 C31 C34 120.9(4) . .
C32 C31 C34 120.6(3) . .
C33 C32 C31 123.8(3) . .
C33 C32 H32 118.1 . .
C31 C32 H32 118.1 . .
C32 C33 C28 116.9(4) . .
C32 C33 H33 121.6 . .
C28 C33 H33 121.6 . .
C31 C34 H34A 109.5 . .
C31 C34 H34B 109.5 . .
H34A C34 H34B 109.5 . .
C31 C34 H34C 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C9 O1 C12 104.4(5) . .
C9 C10 C11 107.1(6) . .
C9 C10 H10A 126.5 . .
C11 C10 H10A 126.5 . .
C12 C11 C10 106.9(6) . .
C12 C11 H11A 126.5 . .
C10 C11 H11A 126.5 . .
C11 C12 O1 112.3(5) . .
C11 C12 H12A 123.9 . .
O1 C12 H12A 123.9 . .
Cl1 C35 C35 63.1(11) . 2_755
Cl1 C35 Cl2 97.1(9) . .
C35 C35 Cl2 78.1(10) 2_755 .
Cl1 C35 Cl1 112.8(8) . 2_755
C35 C35 Cl1 69.1(13) 2_755 2_755
Cl2 C35 Cl1 116.3(15) . 2_755
Cl1 C35 Cl2 101.8(8) . 2_755
C35 C35 Cl2 59.5(9) 2_755 2_755
Cl2 C35 Cl2 26.2(19) . 2_755
Cl1 C35 Cl2 91.1(12) 2_755 2_755
C35 Cl1 C35 47.7(8) . 2_755
Cl2 Cl2 C35 92.2(11) 2_755 .
Cl2 Cl2 C35 61.6(12) 2_755 2_755
C35 Cl2 C35 42.4(7) . 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C30 1.397(5) .
N1 C1 1.414(5) .
N1 H1 0.73(4) .
N2 C28 1.381(4) .
N2 C14 1.395(4) .
N2 C21 1.428(4) .
C1 C2 1.386(5) .
C1 C6 1.394(5) .
C2 C3 1.369(6) .
C2 H2 0.9300 .
C3 C4 1.387(6) .
C3 H3 0.9300 .
C4 C5 1.374(6) .
C4 C7 1.506(6) .
C5 C6 1.390(5) .
C5 H5 0.9300 .
C6 C8 1.521(5) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C13 1.486(5) .
C8 C9 1.501(5) .
C8 H8 0.9800 .
C9 C10 1.325(6) .
C9 O1 1.341(5) .
C13 C14 1.372(5) .
C13 C29 1.425(5) .
C14 C15 1.466(5) .
C15 C20 1.392(5) .
C15 C16 1.396(5) .
C16 C17 1.369(5) .
C16 H16 0.9300 .
C17 C18 1.365(6) .
C17 H17 0.9300 .
C18 C19 1.390(7) .
C18 H18 0.9300 .
C19 C20 1.371(6) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C21 C22 1.367(5) .
C21 C26 1.370(5) .
C22 C23 1.375(5) .
C22 H22 0.9300 .
C23 C24 1.382(6) .
C23 H23 0.9300 .
C24 C25 1.373(6) .
C24 C27 1.504(5) .
C25 C26 1.371(6) .
C25 H25 0.9300 .
C26 H26 0.9300 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 C33 1.388(5) .
C28 C29 1.394(5) .
C29 C30 1.401(5) .
C30 C31 1.392(5) .
C31 C32 1.401(6) .
C31 C34 1.506(6) .
C32 C33 1.366(6) .
C32 H32 0.9300 .
C33 H33 0.9300 .
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9600 .
O1 C12 1.393(9) .
C10 C11 1.410(8) .
C10 H10A 0.9300 .
C11 C12 1.235(10) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
C35 Cl1 1.682(17) .
C35 C35 1.33(2) 2_755
C35 Cl2 1.70(2) .
C35 Cl1 1.605(16) 2_755
C35 Cl2 1.931(19) 2_755
Cl1 C35 1.605(16) 2_755
Cl2 Cl2 0.85(6) 2_755
Cl2 C35 1.931(19) 2_755
