#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:37:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178878 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/07/4110737.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_4110737
loop_
_publ_author_name
'Laura D. Shirtcliff'
'Austin G. Hayes'
'Michael M. Haley'
'Felix Köhler'
'Kirsten Hess'
'Rainer Herges'
_publ_section_title
;
 Biscyclization Reactions in Butadiyne- and Ethyne-Linked Triazenes and
 Diazenes: Concerted versus Stepwise Coarctate Cyclizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9711
_journal_page_last               9721
_journal_paper_doi               10.1021/ja054547v
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C24 H26 Cl2 N6'
_chemical_formula_weight         469.41
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.862(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3847(17)
_cell_length_b                   15.410(3)
_cell_length_c                   9.877(2)
_cell_measurement_reflns_used    4790
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.25
_cell_volume                     1167.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0112
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8452
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.4529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                3919
_reflns_number_total             4083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja054547vsi20050707_084437.cif
_cod_data_source_block           lds1
_cod_database_code               4110737
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
_atom_site_refinement_flags
Cl1 Cl -0.05906(19) 0.58223(11) 0.77053(16) 0.1113(5) Uani 1 1 d U
Cl2 Cl 0.02065(14) 0.31866(6) 0.07669(12) 0.0807(3) Uani 1 1 d U
N1 N 0.4665(4) 0.39708(17) 0.6344(3) 0.0570(6) Uani 1 1 d .
N2 N 0.4862(3) 0.44887(16) 0.5364(3) 0.0496(6) Uani 1 1 d .
N3 N 0.4500(3) 0.59369(18) 0.3239(3) 0.0567(6) Uani 1 1 d D
N4 N -0.2025(3) 0.67203(19) 0.1276(3) 0.0568(6) Uani 1 1 d .
N5 N -0.0661(3) 0.70329(17) 0.2359(3) 0.0509(6) Uani 1 1 d .
N6 N 0.2901(3) 0.72698(15) 0.4805(3) 0.0468(5) Uani 1 1 d .
C1 C 0.0983(5) 0.5241(3) 0.7328(4) 0.0692(10) Uani 1 1 d .
C2 C 0.1620(6) 0.4466(3) 0.8086(4) 0.0775(12) Uani 1 1 d .
H2 H 0.1206 0.4264 0.8794 0.093 Uiso 1 1 calc R
C3 C 0.2844(5) 0.3996(2) 0.7808(4) 0.0677(9) Uani 1 1 d .
H3 H 0.3265 0.3459 0.8294 0.081 Uiso 1 1 calc R
C4 C 0.3453(4) 0.4329(2) 0.6790(3) 0.0522(7) Uani 1 1 d .
C5 C 0.2813(4) 0.51158(18) 0.6042(3) 0.0448(6) Uani 1 1 d .
C6 C 0.1544(4) 0.5589(2) 0.6311(4) 0.0583(8) Uani 1 1 d .
H6 H 0.1094 0.6121 0.5819 0.070 Uiso 1 1 calc R
C7 C 0.3770(3) 0.52017(18) 0.5122(3) 0.0417(6) Uani 1 1 d .
C8 C 0.3669(3) 0.58703(18) 0.4121(3) 0.0412(5) Uani 1 1 d .
C9 C 0.2350(3) 0.65792(17) 0.3938(3) 0.0407(6) Uani 1 1 d .
C10 C 0.0686(3) 0.64191(18) 0.2829(3) 0.0420(6) Uani 1 1 d .
C11 C 0.0043(4) 0.56427(19) 0.1954(3) 0.0432(6) Uani 1 1 d .
C12 C 0.0627(4) 0.4800(2) 0.1883(3) 0.0481(6) Uani 1 1 d .
H12 H 0.1772 0.4621 0.2514 0.058 Uiso 1 1 calc R
C13 C -0.0508(4) 0.4244(2) 0.0874(4) 0.0540(7) Uani 1 1 d .
C14 C -0.2193(5) 0.4469(2) -0.0102(4) 0.0618(9) Uani 1 1 d .
H14 H -0.2920 0.4060 -0.0798 0.074 Uiso 1 1 calc R
C15 C -0.2786(4) 0.5295(2) -0.0040(4) 0.0602(8) Uani 1 1 d .
H15 H -0.3929 0.5467 -0.0687 0.072 Uiso 1 1 calc R
C16 C -0.1662(4) 0.5873(2) 0.0997(3) 0.0480(6) Uani 1 1 d .
C17 C 0.4404(5) 0.6728(2) 0.2348(4) 0.0663(9) Uani 1 1 d .
H17A H 0.3866 0.7203 0.2692 0.080 Uiso 1 1 calc R
H17B H 0.5601 0.6911 0.2513 0.080 Uiso 1 1 calc R
C18 C 0.3380(7) 0.6591(3) 0.0741(5) 0.0916(14) Uani 1 1 d .
H18A H 0.3889 0.6111 0.0398 0.137 Uiso 1 1 calc R
H18B H 0.3402 0.7121 0.0201 0.137 Uiso 1 1 calc R
H18C H 0.2172 0.6449 0.0562 0.137 Uiso 1 1 calc R
C19 C 0.5525(7) 0.5089(7) 0.2875(9) 0.181(5) Uani 1 1 d D
H19A H 0.5122 0.4522 0.3093 0.217 Uiso 1 1 calc R
H19B H 0.5465 0.5095 0.1853 0.217 Uiso 1 1 calc R
C20 C 0.7058(17) 0.5315(4) 0.3867(11) 0.220(7) Uani 1 1 d D
H20A H 0.7300 0.5918 0.3698 0.331 Uiso 1 1 calc R
H20B H 0.7954 0.4935 0.3787 0.331 Uiso 1 1 calc R
H20C H 0.7067 0.5260 0.4859 0.331 Uiso 1 1 calc R
C21 C 0.4740(4) 0.7346(2) 0.5923(4) 0.0588(8) Uani 1 1 d .
H21A H 0.5250 0.7892 0.5749 0.071 Uiso 1 1 calc R
H21B H 0.5432 0.6858 0.5793 0.071 Uiso 1 1 calc R
C22 C 0.4865(6) 0.7341(4) 0.7483(4) 0.0955(15) Uani 1 1 d .
H22A H 0.4255 0.7848 0.7640 0.143 Uiso 1 1 calc R
H22B H 0.6094 0.7361 0.8176 0.143 Uiso 1 1 calc R
H22C H 0.4328 0.6810 0.7652 0.143 Uiso 1 1 calc R
C23 C 0.1815(5) 0.8054(2) 0.4652(4) 0.0600(8) Uani 1 1 d .
H23A H 0.1122 0.8164 0.3586 0.072 Uiso 1 1 calc R
H23B H 0.2595 0.8558 0.5057 0.072 Uiso 1 1 calc R
C24 C 0.0586(5) 0.7990(3) 0.5423(5) 0.0770(11) Uani 1 1 d .
H24A H -0.0291 0.7542 0.4943 0.116 Uiso 1 1 calc R
H24B H 0.0006 0.8550 0.5360 0.116 Uiso 1 1 calc R
H24C H 0.1247 0.7837 0.6465 0.116 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'
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
N2 N1 C4 108.7(2)
N1 N2 C7 109.7(2)
C8 N3 C17 122.5(3)
C8 N3 C19 122.1(3)
C17 N3 C19 114.9(3)
N5 N4 C16 108.7(2)
N4 N5 C10 110.2(3)
C9 N6 C23 123.3(2)
C9 N6 C21 121.8(3)
C23 N6 C21 114.7(2)
C6 C1 C2 123.7(4)
C6 C1 Cl1 117.6(3)
C2 C1 Cl1 118.7(3)
C3 C2 C1 119.9(3)
C2 C3 C4 118.1(3)
N1 C4 C3 128.0(3)
N1 C4 C5 110.6(3)
C3 C4 C5 121.4(3)
C6 C5 C4 120.4(3)
C6 C5 C7 137.0(3)
C4 C5 C7 102.6(3)
C1 C6 C5 116.4(3)
N2 C7 C8 123.3(2)
N2 C7 C5 108.4(2)
C8 C7 C5 128.3(3)
N3 C8 C7 128.5(3)
N3 C8 C9 114.9(2)
C7 C8 C9 116.5(2)
N6 C9 C10 128.4(3)
N6 C9 C8 117.1(2)
C10 C9 C8 114.5(2)
C9 C10 N5 123.6(3)
C9 C10 C11 128.6(2)
N5 C10 C11 107.8(2)
C12 C11 C16 118.8(3)
C12 C11 C10 138.1(3)
C16 C11 C10 103.0(2)
C13 C12 C11 117.7(3)
C12 C13 C14 124.1(3)
C12 C13 Cl2 118.2(3)
C14 C13 Cl2 117.7(2)
C15 C14 C13 118.8(3)
C14 C15 C16 118.3(3)
N4 C16 C15 127.3(3)
N4 C16 C11 110.4(2)
C15 C16 C11 122.3(3)
C18 C17 N3 112.7(4)
C20 C19 N3 93.7(9)
N6 C21 C22 112.4(3)
N6 C23 C24 114.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.755(4)
Cl2 C13 1.754(3)
N1 N2 1.315(4)
N1 C4 1.375(5)
N2 C7 1.388(4)
N3 C8 1.321(3)
N3 C17 1.487(4)
N3 C19 1.681(10)
N4 N5 1.301(4)
N4 C16 1.393(4)
N5 C10 1.400(4)
N6 C9 1.326(4)
N6 C23 1.484(4)
N6 C21 1.494(4)
C1 C6 1.378(5)
C1 C2 1.396(6)
C2 C3 1.372(6)
C3 C4 1.397(5)
C4 C5 1.408(4)
C5 C6 1.402(4)
C5 C7 1.441(4)
C7 C8 1.407(4)
C8 C9 1.512(4)
C9 C10 1.404(4)
C10 C11 1.446(4)
C11 C12 1.399(4)
C11 C16 1.404(4)
C12 C13 1.366(4)
C13 C14 1.395(5)
C14 C15 1.377(5)
C15 C16 1.397(4)
C17 C18 1.483(6)
C19 C20 1.309(12)
C21 C22 1.501(6)
C23 C24 1.512(5)
