#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:51:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180158 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/54/7105496.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_7105496
loop_
_publ_author_name
'Ishigaki, Yuhei'
'Mahendar, Velisoju'
'Oguri, Hiroki'
'Oikawa, Hideaki'
_publ_section_title
;
 An anti-tetraamination of a 1,3-diene unit via cascade annulations of
 the azulenone scaffold with dicarbonyl azo-compounds
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              3304
_journal_page_last               3305
_journal_paper_doi               10.1039/b926676c
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C33 H34 Br N5 O8'
_chemical_formula_weight         708.56
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                 108.9510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0539(2)
_cell_length_b                   23.6403(4)
_cell_length_c                   12.1023(2)
_cell_measurement_temperature    223(2)
_cell_volume                     3261.72(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(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           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            57974
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_T_max  0.9364
_exptl_absorpt_correction_T_min  0.7320
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0649
_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)+(0.0831P)²+5.8952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.2151
_reflns_number_gt                3807
_reflns_number_total             5962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b926676c.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        3261.70(10)
_cod_database_code               7105496
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33046(7) 0.13979(3) -0.08134(8) 0.1065(4) Uani 1 1 d . . .
O1 O -0.0238(4) 0.37012(17) -0.1106(3) 0.0798(11) Uani 1 1 d . . .
O2 O 0.0925(3) 0.37212(12) 0.0788(3) 0.0535(7) Uani 1 1 d . . .
O3 O 0.5155(3) 0.34583(14) 0.1745(3) 0.0647(9) Uani 1 1 d . . .
O4 O 0.6207(3) 0.48450(14) 0.4536(3) 0.0587(8) Uani 1 1 d . . .
O5 O 0.3215(3) 0.52460(14) -0.1908(3) 0.0596(8) Uani 1 1 d . . .
O6 O 0.1942(3) 0.45291(14) -0.2055(3) 0.0585(8) Uani 1 1 d . . .
O7 O 0.2199(3) 0.62281(14) -0.0628(3) 0.0627(9) Uani 1 1 d . . .
O8 O 0.3928(3) 0.62848(13) 0.0879(3) 0.0630(9) Uani 1 1 d . . .
N1 N 0.2406(3) 0.50647(14) -0.0454(3) 0.0455(8) Uani 1 1 d . . .
N2 N 0.3223(3) 0.54494(15) 0.0257(3) 0.0520(9) Uani 1 1 d . . .
N3 N 0.4209(3) 0.42644(14) 0.2062(3) 0.0457(8) Uani 1 1 d . . .
N4 N 0.4522(3) 0.46913(15) 0.2954(3) 0.0485(8) Uani 1 1 d . . .
N5 N 0.5859(3) 0.40139(15) 0.3428(3) 0.0494(8) Uani 1 1 d . . .
C1 C 0.0838(5) 0.2665(2) -0.1393(5) 0.0704(14) Uani 1 1 d . . .
H1 H 0.0148 0.2766 -0.1993 0.084 Uiso 1 1 calc R . .
C2 C 0.1464(6) 0.2194(2) -0.1530(5) 0.0766(16) Uani 1 1 d . . .
H2 H 0.1196 0.1973 -0.2211 0.092 Uiso 1 1 calc R . .
C3 C 0.2476(6) 0.2055(2) -0.0662(5) 0.0742(15) Uani 1 1 d . . .
C4 C 0.2902(5) 0.2381(2) 0.0335(5) 0.0704(14) Uani 1 1 d . . .
H3 H 0.3613 0.2288 0.0913 0.085 Uiso 1 1 calc R . .
C5 C 0.2257(5) 0.2850(2) 0.0469(5) 0.0618(12) Uani 1 1 d . . .
H4 H 0.2533 0.3075 0.1144 0.074 Uiso 1 1 calc R . .
C6 C 0.1212(4) 0.2988(2) -0.0388(4) 0.0565(11) Uani 1 1 d . . .
C7 C 0.0538(5) 0.3500(2) -0.0296(4) 0.0585(12) Uani 1 1 d . . .
C8 C 0.0666(4) 0.43174(17) 0.0935(4) 0.0501(10) Uani 1 1 d . . .
H5 H 0.0024 0.4461 0.0253 0.060 Uiso 1 1 calc R . .
C9 C 0.0391(4) 0.4400(2) 0.2067(4) 0.0583(12) Uani 1 1 d . . .
H6 H 0.0690 0.4083 0.2604 0.070 Uiso 1 1 calc R . .
H7 H -0.0456 0.4434 0.1914 0.070 Uiso 1 1 calc R . .
C10 C 0.1026(4) 0.4952(2) 0.2570(4) 0.0573(12) Uani 1 1 d . . .
H8 H 0.0493 0.5276 0.2345 0.069 Uiso 1 1 calc R . .
H9 H 0.1347 0.4935 0.3425 0.069 Uiso 1 1 calc R . .
C11 C 0.1984(4) 0.49942(18) 0.2046(4) 0.0469(10) Uani 1 1 d . . .
C12 C 0.1779(4) 0.46491(18) 0.1126(4) 0.0447(9) Uani 1 1 d . . .
C13 C 0.2479(4) 0.45649(17) 0.0314(4) 0.0442(9) Uani 1 1 d . . .
H10 H 0.2205 0.4222 -0.0167 0.053 Uiso 1 1 calc R . .
C14 C 0.3822(4) 0.45371(17) 0.0925(4) 0.0446(9) Uani 1 1 d . . .
H11 H 0.4217 0.4370 0.0401 0.054 Uiso 1 1 calc R . .
C15 C 0.4150(4) 0.51684(18) 0.1163(4) 0.0475(10) Uani 1 1 d . . .
H12 H 0.4929 0.5250 0.1091 0.057 Uiso 1 1 calc R . .
C16 C 0.4154(4) 0.52514(18) 0.2432(4) 0.0487(10) Uani 1 1 d . . .
H13 H 0.4747 0.5539 0.2830 0.058 Uiso 1 1 calc R . .
C17 C 0.2974(4) 0.54039(19) 0.2558(4) 0.0518(10) Uani 1 1 d . . .
H14 H 0.3082 0.5446 0.3392 0.062 Uiso 1 1 calc R . .
H15 H 0.2736 0.5774 0.2191 0.062 Uiso 1 1 calc R . .
C18 C 0.5618(4) 0.45624(19) 0.3732(4) 0.0500(10) Uani 1 1 d . . .
C19 C 0.5106(4) 0.38638(19) 0.2335(4) 0.0521(10) Uani 1 1 d . . .
C20 C 0.6903(4) 0.3703(2) 0.4031(4) 0.0556(11) Uani 1 1 d . . .
C21 C 0.7043(5) 0.3500(2) 0.5130(5) 0.0715(15) Uani 1 1 d . . .
H16 H 0.6475 0.3572 0.5492 0.086 Uiso 1 1 calc R . .
C22 C 0.8041(6) 0.3186(3) 0.5700(5) 0.095(2) Uani 1 1 d . . .
H17 H 0.8155 0.3044 0.6454 0.114 Uiso 1 1 calc R . .
C23 C 0.8857(6) 0.3084(3) 0.5157(6) 0.093(2) Uani 1 1 d . . .
H18 H 0.9523 0.2864 0.5534 0.112 Uiso 1 1 calc R . .
C24 C 0.8708(6) 0.3299(3) 0.4071(6) 0.0884(19) Uani 1 1 d . . .
H19 H 0.9283 0.3235 0.3715 0.106 Uiso 1 1 calc R . .
C25 C 0.7726(5) 0.3608(2) 0.3494(5) 0.0707(14) Uani 1 1 d . . .
H20 H 0.7620 0.3752 0.2742 0.085 Uiso 1 1 calc R . .
C26 C 0.2598(4) 0.49646(18) -0.1529(4) 0.0480(10) Uani 1 1 d . . .
C27 C 0.2051(5) 0.4333(2) -0.3167(4) 0.0659(13) Uani 1 1 d . . .
H21 H 0.2843 0.4413 -0.3206 0.079 Uiso 1 1 calc R . .
C28 C 0.1167(8) 0.4602(5) -0.4110(6) 0.146(4) Uani 1 1 d . . .
H22 H 0.1222 0.5009 -0.4004 0.176 Uiso 1 1 calc R . .
H23 H 0.0398 0.4475 -0.4121 0.176 Uiso 1 1 calc R . .
H24 H 0.1281 0.4504 -0.4844 0.176 Uiso 1 1 calc R . .
C29 C 0.1840(13) 0.3715(4) -0.3162(9) 0.185(6) Uani 1 1 d . . .
H25 H 0.1744 0.3561 -0.3931 0.222 Uiso 1 1 calc R . .
H26 H 0.1135 0.3645 -0.2962 0.222 Uiso 1 1 calc R . .
H27 H 0.2504 0.3534 -0.2590 0.222 Uiso 1 1 calc R . .
C30 C 0.3035(4) 0.60141(19) 0.0100(4) 0.0521(11) Uani 1 1 d . . .
C31 C 0.3842(5) 0.6905(2) 0.0917(5) 0.0734(15) Uani 1 1 d . . .
H28 H 0.3287 0.7047 0.0173 0.088 Uiso 1 1 calc R . .
C32 C 0.3420(8) 0.7050(3) 0.1888(8) 0.127(3) Uani 1 1 d . . .
H29 H 0.2670 0.6868 0.1775 0.152 Uiso 1 1 calc R . .
H30 H 0.3329 0.7457 0.1917 0.152 Uiso 1 1 calc R . .
H31 H 0.3982 0.6921 0.2616 0.152 Uiso 1 1 calc R . .
C33 C 0.5051(7) 0.7122(3) 0.1078(8) 0.118(3) Uani 1 1 d . . .
H32 H 0.5584 0.6988 0.1816 0.141 Uiso 1 1 calc R . .
H33 H 0.5042 0.7533 0.1076 0.141 Uiso 1 1 calc R . .
H34 H 0.5309 0.6988 0.0444 0.141 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 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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
_geom_angle_publ_flag
C7 O2 C8 118.1(4) . . ?
C26 O6 C27 117.9(4) . . ?
C30 O8 C31 116.7(4) . . ?
N2 N1 C26 112.3(3) . . ?
N2 N1 C13 104.1(3) . . ?
C26 N1 C13 116.6(3) . . ?
C30 N2 N1 119.9(4) . . ?
C30 N2 C15 127.6(4) . . ?
N1 N2 C15 112.3(3) . . ?
C19 N3 N4 107.8(3) . . ?
C19 N3 C14 120.8(4) . . ?
N4 N3 C14 109.0(3) . . ?
C18 N4 N3 108.4(3) . . ?
C18 N4 C16 125.3(4) . . ?
N3 N4 C16 109.9(3) . . ?
C19 N5 C18 111.0(4) . . ?
C19 N5 C20 123.3(4) . . ?
C18 N5 C20 124.2(4) . . ?
C6 C1 C2 121.0(6) . . ?
C3 C2 C1 119.2(5) . . ?
C2 C3 C4 121.4(6) . . ?
C2 C3 Br1 119.5(4) . . ?
C4 C3 Br1 119.1(5) . . ?
C3 C4 C5 118.8(6) . . ?
C6 C5 C4 120.4(5) . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 C7 119.2(5) . . ?
C5 C6 C7 121.6(4) . . ?
O1 C7 O2 124.6(5) . . ?
O1 C7 C6 124.0(5) . . ?
O2 C7 C6 111.4(4) . . ?
O2 C8 C12 107.8(3) . . ?
O2 C8 C9 110.4(4) . . ?
C12 C8 C9 103.8(4) . . ?
C8 C9 C10 103.8(4) . . ?
C11 C10 C9 104.1(4) . . ?
C12 C11 C10 110.8(4) . . ?
C12 C11 C17 130.0(4) . . ?
C10 C11 C17 119.2(4) . . ?
C11 C12 C13 129.4(4) . . ?
C11 C12 C8 111.1(4) . . ?
C13 C12 C8 119.5(4) . . ?
N1 C13 C12 111.8(3) . . ?
N1 C13 C14 99.9(3) . . ?
C12 C13 C14 114.5(3) . . ?
N3 C14 C15 105.6(3) . . ?
N3 C14 C13 115.8(3) . . ?
C15 C14 C13 102.2(3) . . ?
N2 C15 C14 102.4(3) . . ?
N2 C15 C16 116.5(4) . . ?
C14 C15 C16 103.0(3) . . ?
N4 C16 C17 109.3(4) . . ?
N4 C16 C15 102.4(3) . . ?
C17 C16 C15 115.3(4) . . ?
C11 C17 C16 116.6(4) . . ?
O4 C18 N4 127.6(4) . . ?
O4 C18 N5 127.3(4) . . ?
N4 C18 N5 105.0(4) . . ?
O3 C19 N5 128.7(4) . . ?
O3 C19 N3 125.6(4) . . ?
N5 C19 N3 105.7(4) . . ?
C25 C20 C21 121.5(5) . . ?
C25 C20 N5 119.5(4) . . ?
C21 C20 N5 118.9(4) . . ?
C20 C21 C22 118.8(5) . . ?
C23 C22 C21 119.8(6) . . ?
C24 C23 C22 120.4(6) . . ?
C23 C24 C25 120.7(6) . . ?
C20 C25 C24 118.9(6) . . ?
O5 C26 O6 126.6(4) . . ?
O5 C26 N1 124.6(4) . . ?
O6 C26 N1 108.8(4) . . ?
C28 C27 O6 109.0(5) . . ?
C28 C27 C29 110.9(8) . . ?
O6 C27 C29 103.9(5) . . ?
O7 C30 O8 126.8(4) . . ?
O7 C30 N2 125.0(4) . . ?
O8 C30 N2 108.2(4) . . ?
C32 C31 O8 107.8(5) . . ?
C32 C31 C33 113.1(6) . . ?
O8 C31 C33 105.6(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.887(6) . ?
O1 C7 1.211(6) . ?
O2 C7 1.347(6) . ?
O2 C8 1.467(5) . ?
O3 C19 1.209(5) . ?
O4 C18 1.204(5) . ?
O5 C26 1.195(5) . ?
O6 C26 1.328(5) . ?
O6 C27 1.469(5) . ?
O7 C30 1.212(6) . ?
O8 C30 1.341(5) . ?
O8 C31 1.472(6) . ?
N1 N2 1.409(5) . ?
N1 C26 1.414(5) . ?
N1 C13 1.488(5) . ?
N2 C30 1.357(6) . ?
N2 C15 1.448(5) . ?
N3 C19 1.394(5) . ?
N3 N4 1.436(5) . ?
N3 C14 1.452(5) . ?
N4 C18 1.384(6) . ?
N4 C16 1.472(5) . ?
N5 C19 1.386(6) . ?
N5 C18 1.404(6) . ?
N5 C20 1.435(6) . ?
C1 C6 1.383(7) . ?
C1 C2 1.384(8) . ?
C2 C3 1.367(9) . ?
C3 C4 1.383(8) . ?
C4 C5 1.395(7) . ?
C5 C6 1.385(7) . ?
C6 C7 1.481(7) . ?
C8 C12 1.506(6) . ?
C8 C9 1.523(6) . ?
C9 C10 1.536(7) . ?
C10 C11 1.490(6) . ?
C11 C12 1.337(6) . ?
C11 C17 1.505(6) . ?
C12 C13 1.502(6) . ?
C13 C14 1.548(6) . ?
C14 C15 1.547(6) . ?
C15 C16 1.547(6) . ?
C16 C17 1.522(6) . ?
C20 C25 1.370(7) . ?
C20 C21 1.372(7) . ?
C21 C22 1.391(8) . ?
C22 C23 1.370(9) . ?
C23 C24 1.366(9) . ?
C24 C25 1.374(8) . ?
C27 C28 1.433(9) . ?
C27 C29 1.484(10) . ?
C31 C32 1.464(9) . ?
C31 C33 1.497(9) . ?
