#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/66/4026686.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_4026686
loop_
_publ_author_name
'Benedikt Neue'
'Ralph Reiermann'
'Klaus Gerdes'
'Roland Fröhlich'
'Birgit Wibbeling'
'Ernst-Ulrich Würthwein'
_publ_section_title
;
 Ring Closure Reactions of 2,6-Diazaheptatrienyl Metal Compounds:
 Synthesis of 3-Aminoindole Derivatives and 14-Membered Macrocyclic Dimers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8794
_journal_page_last               8806
_journal_paper_doi               10.1021/jo201521v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C21 H16 Cl2 N2'
_chemical_formula_weight         367.26
_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                 110.605(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9779(1)
_cell_length_b                   19.5200(1)
_cell_length_c                   9.1673(1)
_cell_measurement_reflns_used    3049
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1838.78(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN  (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13858
_diffrn_reflns_theta_full        67.82
_diffrn_reflns_theta_max         67.82
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    3.203
_exptl_absorpt_correction_T_max  0.7401
_exptl_absorpt_correction_T_min  0.4466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0033(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0407P)²+1.1914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2681
_reflns_number_total             3238
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201521v_si_001.cif
_cod_data_source_block           wue4254
_cod_database_code               4026686
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
C1 C 0.5400(2) 0.32203(12) -0.4444(3) 0.0428(5) Uani 1 1 d .
H1 H 0.5040 0.2917 -0.5283 0.051 Uiso 1 1 calc R
C11 C 0.6298(2) 0.29458(11) -0.2963(3) 0.0405(5) Uani 1 1 d .
C12 C 0.7026(2) 0.33767(12) -0.1752(3) 0.0459(5) Uani 1 1 d .
H12 H 0.6878 0.3852 -0.1837 0.055 Uiso 1 1 calc R
C13 C 0.7956(2) 0.31134(12) -0.0436(3) 0.0465(6) Uani 1 1 d .
H13 H 0.8447 0.3406 0.0370 0.056 Uiso 1 1 calc R
C14 C 0.8161(2) 0.24130(12) -0.0314(2) 0.0421(5) Uani 1 1 d .
C15 C 0.7428(2) 0.19712(12) -0.1470(3) 0.0449(5) Uani 1 1 d .
H15 H 0.7554 0.1495 -0.1359 0.054 Uiso 1 1 calc R
C16 C 0.6506(2) 0.22428(12) -0.2789(3) 0.0440(5) Uani 1 1 d .
H16 H 0.6010 0.1947 -0.3586 0.053 Uiso 1 1 calc R
N2 N 0.50901(18) 0.38472(10) -0.4638(2) 0.0469(5) Uani 1 1 d .
C3 C 0.4247(2) 0.40611(13) -0.6207(3) 0.0497(6) Uani 1 1 d .
H3A H 0.4214 0.3695 -0.6952 0.060 Uiso 1 1 calc R
H3B H 0.4617 0.4469 -0.6516 0.060 Uiso 1 1 calc R
C4 C 0.2888(2) 0.42183(11) -0.6267(3) 0.0430(5) Uani 1 1 d .
C41 C 0.2473(3) 0.48879(13) -0.6224(3) 0.0556(6) Uani 1 1 d .
H41 H 0.3063 0.5250 -0.6120 0.067 Uiso 1 1 calc R
C42 C 0.1218(3) 0.50332(14) -0.6333(3) 0.0636(7) Uani 1 1 d .
H42 H 0.0956 0.5490 -0.6312 0.076 Uiso 1 1 calc R
C5 C 0.2006(2) 0.36838(11) -0.6372(2) 0.0399(5) Uani 1 1 d .
C51 C 0.0734(2) 0.38346(12) -0.6487(3) 0.0466(6) Uani 1 1 d .
H51 H 0.0139 0.3477 -0.6575 0.056 Uiso 1 1 calc R
C52 C 0.0345(3) 0.45065(14) -0.6472(3) 0.0598(7) Uani 1 1 d .
H52 H -0.0515 0.4605 -0.6557 0.072 Uiso 1 1 calc R
N6 N 0.24200(17) 0.30078(9) -0.6488(2) 0.0407(4) Uani 1 1 d .
C7 C 0.2060(2) 0.25225(11) -0.5807(2) 0.0409(5) Uani 1 1 d .
H7 H 0.1563 0.2626 -0.5185 0.049 Uiso 1 1 calc R
C71 C 0.2396(2) 0.18042(11) -0.5963(2) 0.0400(5) Uani 1 1 d .
C72 C 0.3186(2) 0.16205(12) -0.6799(3) 0.0456(5) Uani 1 1 d .
H72 H 0.3508 0.1962 -0.7290 0.055 Uiso 1 1 calc R
C73 C 0.3502(2) 0.09458(12) -0.6919(3) 0.0493(6) Uani 1 1 d .
H73 H 0.4040 0.0825 -0.7481 0.059 Uiso 1 1 calc R
C74 C 0.3013(2) 0.04492(11) -0.6197(3) 0.0480(6) Uani 1 1 d .
C75 C 0.2218(3) 0.06122(13) -0.5385(3) 0.0539(6) Uani 1 1 d .
H75 H 0.1886 0.0267 -0.4914 0.065 Uiso 1 1 calc R
C76 C 0.1910(2) 0.12934(12) -0.5268(3) 0.0494(6) Uani 1 1 d .
H76 H 0.1366 0.1411 -0.4712 0.059 Uiso 1 1 calc R
Cl1 Cl 0.93623(6) 0.20780(3) 0.13190(7) 0.0538(2) Uani 1 1 d .
Cl2 Cl 0.34366(7) -0.04049(3) -0.63179(9) 0.0708(2) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
N2 C1 C11 122.8(2)
C16 C11 C12 118.5(2)
C16 C11 C1 119.7(2)
C12 C11 C1 121.6(2)
C13 C12 C11 120.8(2)
C12 C13 C14 119.3(2)
C15 C14 C13 121.3(2)
C15 C14 Cl1 119.08(18)
C13 C14 Cl1 119.62(17)
C16 C15 C14 118.8(2)
C15 C16 C11 121.3(2)
C1 N2 C3 117.2(2)
N2 C3 C4 111.60(19)
C41 C4 C5 118.5(2)
C41 C4 C3 121.4(2)
C5 C4 C3 120.1(2)
C42 C41 C4 121.4(2)
C41 C42 C52 119.9(2)
C51 C5 C4 119.8(2)
C51 C5 N6 122.1(2)
C4 C5 N6 117.9(2)
C52 C51 C5 120.3(2)
C42 C52 C51 120.1(2)
C7 N6 C5 119.70(19)
N6 C7 C71 122.0(2)
C76 C71 C72 118.9(2)
C76 C71 C7 119.4(2)
C72 C71 C7 121.7(2)
C73 C72 C71 120.9(2)
C72 C73 C74 118.8(2)
C75 C74 C73 121.7(2)
C75 C74 Cl2 119.44(19)
C73 C74 Cl2 118.8(2)
C74 C75 C76 119.0(2)
C75 C76 C71 120.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.266(3)
C1 C11 1.470(3)
C11 C16 1.391(3)
C11 C12 1.398(3)
C12 C13 1.377(3)
C13 C14 1.384(3)
C14 C15 1.384(3)
C14 Cl1 1.737(2)
C15 C16 1.381(3)
N2 C3 1.471(3)
C3 C4 1.505(3)
C4 C41 1.389(3)
C4 C5 1.403(3)
C41 C42 1.376(4)
C42 C52 1.380(4)
C5 C51 1.394(3)
C5 N6 1.412(3)
C51 C52 1.381(3)
N6 C7 1.272(3)
C7 C71 1.470(3)
C71 C76 1.387(3)
C71 C72 1.392(3)
C72 C73 1.376(3)
C73 C74 1.384(3)
C74 C75 1.370(4)
C74 Cl2 1.745(2)
C75 C76 1.385(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
N2 C1 C11 C16 174.3(2)
N2 C1 C11 C12 -10.3(3)
C16 C11 C12 C13 2.0(3)
C1 C11 C12 C13 -173.4(2)
C11 C12 C13 C14 -0.5(4)
C12 C13 C14 C15 -1.6(4)
C12 C13 C14 Cl1 178.33(18)
C13 C14 C15 C16 2.2(3)
Cl1 C14 C15 C16 -177.72(17)
C14 C15 C16 C11 -0.7(3)
C12 C11 C16 C15 -1.4(3)
C1 C11 C16 C15 174.2(2)
C11 C1 N2 C3 176.25(19)
C1 N2 C3 C4 107.4(2)
N2 C3 C4 C41 100.7(3)
N2 C3 C4 C5 -79.5(3)
C5 C4 C41 C42 -2.0(4)
C3 C4 C41 C42 177.7(2)
C4 C41 C42 C52 0.6(4)
C41 C4 C5 C51 2.2(3)
C3 C4 C5 C51 -177.5(2)
C41 C4 C5 N6 177.1(2)
C3 C4 C5 N6 -2.7(3)
C4 C5 C51 C52 -1.0(3)
N6 C5 C51 C52 -175.7(2)
C41 C42 C52 C51 0.6(4)
C5 C51 C52 C42 -0.4(4)
C51 C5 N6 C7 -42.1(3)
C4 C5 N6 C7 143.1(2)
C5 N6 C7 C71 176.32(19)
N6 C7 C71 C76 -176.2(2)
N6 C7 C71 C72 3.4(3)
C76 C71 C72 C73 -1.1(3)
C7 C71 C72 C73 179.3(2)
C71 C72 C73 C74 0.4(4)
C72 C73 C74 C75 0.6(4)
C72 C73 C74 Cl2 -178.85(18)
C73 C74 C75 C76 -0.8(4)
Cl2 C74 C75 C76 178.63(19)
C74 C75 C76 C71 0.1(4)
C72 C71 C76 C75 0.9(3)
C7 C71 C76 C75 -179.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659423
