#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:06:43 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140134 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/11/4031108.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_4031108
loop_
_publ_author_name
'Peshkov, Anatoly A.'
'Peshkov, Vsevolod A.'
'Pereshivko, Olga P.'
'Van Hecke, Kristof'
'Kumar, Rakesh'
'V Van der Eycken, Erik'
_publ_section_title
;
 Heck-Suzuki Tandem Reaction for the Synthesis of 3-Benzazepines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6598
_journal_page_last               6608
_journal_paper_doi               10.1021/acs.joc.5b00670
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C29 H31 N O4'
_chemical_formula_sum            'C29 H31 N O4'
_chemical_formula_weight         457.55
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2013-04-04
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.549(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6205(2)
_cell_length_b                   11.36761(17)
_cell_length_c                   19.4826(4)
_cell_measurement_reflns_used    8181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.2098
_cell_measurement_theta_min      3.8854
_cell_volume                     2479.41(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details
;
  1 omega   52.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   52.0000  -95.0000 26

  2 omega   15.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   52.0000 -119.0000 97

  3 omega    0.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -52.0000  -60.0000 28

  4 omega  -42.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   52.0000   60.0000 25

  5 omega  -56.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   52.0000   84.0000 85

  6 omega -103.00  -65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -52.0000   95.0000 38

  7 omega  -96.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -52.0000  119.0000 80

  8 omega   55.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -52.0000  -60.0000 42

  9 omega  137.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   52.0000  -95.0000 29

 10 omega   37.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -52.0000  -84.0000 29

 11 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   52.0000 -119.0000 95

 12 omega  -43.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000  -60.0000 25

 13 omega -118.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -150.0000 37

 14 omega -116.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000    0.0000 97

 15 omega   38.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000 -180.0000 82

 16 omega   74.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -120.0000 25

 17 omega   80.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000    0.0000 27

 18 omega   26.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -120.0000 31

 19 omega   80.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   30.0000 31

 20 omega  116.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   30.0000 42

 21 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -30.0000 26

 22 omega  123.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -30.0000 55

 23 omega   85.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   60.0000 74

 24 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000    0.0000 26

 25 omega   40.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -90.0000 29

 26 omega   35.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 51

 27 omega   82.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  -30.0000 27

 28 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   30.0000 26

 29 omega  124.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000    0.0000 25

 30 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000    0.0000 27

 31 omega   78.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -60.0000 88

 32 omega   82.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000   30.0000 25

 33 omega   47.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -180.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0484756000
_diffrn_orient_matrix_UB_12      -0.0839722000
_diffrn_orient_matrix_UB_13      0.0632835000
_diffrn_orient_matrix_UB_21      -0.1276199000
_diffrn_orient_matrix_UB_22      -0.0174960000
_diffrn_orient_matrix_UB_23      0.0073934000
_diffrn_orient_matrix_UB_31      -0.0174120000
_diffrn_orient_matrix_UB_32      -0.1049012000
_diffrn_orient_matrix_UB_33      -0.0517368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22367
_diffrn_reflns_theta_full        75.39
_diffrn_reflns_theta_max         75.39
_diffrn_reflns_theta_min         3.95
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3216
_exptl_crystal_size_mid          0.1896
_exptl_crystal_size_min          0.1059
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0018(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     312
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0403
_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)+(0.0614P)²+0.3195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                4075
_reflns_number_total             5081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00670_si_002.cif
_cod_data_source_block           evde_ugent001
_cod_depositor_comments
'Adding full bibliography for 4031105--4031108.cif.'
_cod_database_code               4031108
_chemical_oxdiff_formula         'C29 H31 N1 O4'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 -0.18930(12) -0.41893(11) 0.03928(7) 0.0459(3) Uani 1 1 d .
C2 C -0.19412(11) -0.33496(10) 0.09858(6) 0.0425(3) Uani 1 1 d .
C3 C -0.07540(11) -0.28698(10) 0.13869(6) 0.0410(3) Uani 1 1 d .
C4 C 0.02353(11) -0.35782(10) 0.16779(6) 0.0429(3) Uani 1 1 d .
C5 C 0.02392(12) -0.49083(11) 0.16614(7) 0.0495(3) Uani 1 1 d .
H5A H 0.0760 -0.5159 0.1375 0.059 Uiso 1 1 calc R
H5B H 0.0585 -0.5190 0.2143 0.059 Uiso 1 1 calc R
C6 C -0.09587(13) -0.54998(11) 0.13749(7) 0.0482(3) Uani 1 1 d .
H6A H -0.0866 -0.6342 0.1450 0.058 Uiso 1 1 calc R
H6B H -0.1508 -0.5218 0.1636 0.058 Uiso 1 1 calc R
C7 C -0.06198(11) -0.16378(10) 0.14399(6) 0.0430(3) Uani 1 1 d .
H7 H -0.1276 -0.1162 0.1242 0.052 Uiso 1 1 calc R
C8 C 0.04529(12) -0.11199(11) 0.17761(6) 0.0445(3) Uani 1 1 d .
C9 C 0.14467(11) -0.18366(11) 0.20717(7) 0.0470(3) Uani 1 1 d .
C10 C 0.13212(12) -0.30370(11) 0.20191(7) 0.0479(3) Uani 1 1 d .
H10 H 0.1981 -0.3508 0.2217 0.058 Uiso 1 1 calc R
C11 C -0.02803(18) 0.08200(13) 0.14754(10) 0.0762(5) Uani 1 1 d .
H11A H -0.0476 0.0660 0.0974 0.114 Uiso 1 1 calc R
H11B H -0.0030 0.1624 0.1560 0.114 Uiso 1 1 calc R
H11C H -0.0970 0.0687 0.1647 0.114 Uiso 1 1 calc R
C12 C 0.35364(16) -0.19488(19) 0.25948(15) 0.1001(7) Uani 1 1 d .
H12A H 0.3647 -0.2372 0.2191 0.150 Uiso 1 1 calc R
H12B H 0.3463 -0.2497 0.2956 0.150 Uiso 1 1 calc R
H12C H 0.4211 -0.1446 0.2781 0.150 Uiso 1 1 calc R
C13 C -0.11817(14) -0.60962(12) 0.01120(8) 0.0554(3) Uani 1 1 d .
H13A H -0.0330 -0.6253 0.0256 0.067 Uiso 1 1 calc R
H13B H -0.1365 -0.5729 -0.0354 0.067 Uiso 1 1 calc R
C14 C -0.18410(12) -0.72530(11) 0.00491(7) 0.0458(3) Uani 1 1 d .
C15 C -0.15022(14) -0.81385(12) -0.03408(7) 0.0567(4) Uani 1 1 d .
H15 H -0.0853 -0.8015 -0.0526 0.068 Uiso 1 1 calc R
C16 C -0.20970(15) -0.92037(12) -0.04656(8) 0.0608(4) Uani 1 1 d .
H16 H -0.1860 -0.9778 -0.0739 0.073 Uiso 1 1 calc R
C17 C -0.30448(14) -0.94070(11) -0.01808(8) 0.0531(3) Uani 1 1 d .
C18 C -0.33743(14) -0.85474(12) 0.02303(8) 0.0583(4) Uani 1 1 d .
H18 H -0.3997 -0.8688 0.0436 0.070 Uiso 1 1 calc R
C19 C -0.27848(13) -0.74812(12) 0.03373(8) 0.0552(3) Uani 1 1 d .
H19 H -0.3026 -0.6905 0.0608 0.066 Uiso 1 1 calc R
C20 C -0.3398(2) -1.13110(14) -0.07048(12) 0.0851(6) Uani 1 1 d .
H20A H -0.3448 -1.1003 -0.1171 0.128 Uiso 1 1 calc R
H20B H -0.3939 -1.1961 -0.0744 0.128 Uiso 1 1 calc R
H20C H -0.2597 -1.1573 -0.0489 0.128 Uiso 1 1 calc R
C21 C -0.29938(12) -0.30512(11) 0.10947(7) 0.0458(3) Uani 1 1 d .
C22 C -0.30878(11) -0.22653(11) 0.16925(7) 0.0463(3) Uani 1 1 d .
C23 C -0.37270(14) -0.12242(13) 0.15563(9) 0.0607(4) Uani 1 1 d .
H23 H -0.4081 -0.0995 0.1089 0.073 Uiso 1 1 calc R
C24 C -0.38393(16) -0.05206(15) 0.21191(12) 0.0775(5) Uani 1 1 d .
H24 H -0.4265 0.0180 0.2025 0.093 Uiso 1 1 calc R
C25 C -0.33298(16) -0.08483(16) 0.28108(10) 0.0748(5) Uani 1 1 d .
H25 H -0.3406 -0.0371 0.3184 0.090 Uiso 1 1 calc R
C26 C -0.27087(16) -0.18810(15) 0.29483(8) 0.0669(4) Uani 1 1 d .
H26 H -0.2367 -0.2108 0.3417 0.080 Uiso 1 1 calc R
C27 C -0.25829(13) -0.25929(13) 0.23971(7) 0.0555(3) Uani 1 1 d .
H27 H -0.2159 -0.3294 0.2498 0.067 Uiso 1 1 calc R
C28 C -0.41681(13) -0.35379(14) 0.06529(8) 0.0603(4) Uani 1 1 d .
H28A H -0.4685 -0.2889 0.0443 0.072 Uiso 1 1 calc R
H28B H -0.4024 -0.4003 0.0267 0.072 Uiso 1 1 calc R
C29 C -0.4796(2) -0.4286(2) 0.10725(12) 0.1054(8) Uani 1 1 d .
H29A H -0.5553 -0.4535 0.0771 0.158 Uiso 1 1 calc R
H29B H -0.4921 -0.3839 0.1464 0.158 Uiso 1 1 calc R
H29C H -0.4316 -0.4964 0.1251 0.158 Uiso 1 1 calc R
N1 N -0.14626(10) -0.52672(9) 0.06148(6) 0.0483(3) Uani 1 1 d .
O1 O -0.21914(11) -0.38967(9) -0.02358(5) 0.0640(3) Uani 1 1 d .
O2 O 0.06591(9) 0.00643(8) 0.18384(5) 0.0562(3) Uani 1 1 d .
O3 O 0.24875(9) -0.12600(9) 0.23833(6) 0.0632(3) Uani 1 1 d .
O4 O -0.37088(11) -1.04182(9) -0.02771(7) 0.0741(3) 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 0 13 0.0825 -2.0000 -0.0000 13.0001 0.7257 0.3514 -0.6378
0 -6 -7 0.0891 0.0000 -6.0000 -7.0001 0.0608 0.0532 0.9916
1 6 -7 0.0995 1.0000 6.0000 -6.9999 -0.8983 -0.2843 -0.2847
0 2 -12 0.0784 0.0000 2.0000 -12.0000 -0.9273 -0.1237 0.4110
7 -1 1 0.0779 7.0000 -1.0000 0.9999 0.4866 -0.8685 -0.0687
-7 1 -1 0.0281 -7.0000 1.0000 -0.9999 -0.4866 0.8685 0.0687
-1 4 10 0.1491 -1.0000 4.0000 10.0001 0.2485 0.1316 -0.9196
8 0 -5 0.0758 8.0000 -0.0000 -5.0001 0.0714 -1.0579 0.1194
6 4 -3 0.0923 6.0000 4.0000 -3.0000 -0.2349 -0.8579 -0.3689
-3 -6 5 0.1503 -3.0000 -6.0000 4.9999 0.6748 0.5248 0.4230
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 114.51(10)
O1 C1 C2 122.26(11)
O1 C1 N1 123.20(11)
C3 C2 C1 114.34(10)
C21 C2 C1 120.23(12)
C21 C2 C3 125.36(11)
C4 C3 C2 123.16(11)
C4 C3 C7 118.77(11)
C7 C3 C2 117.99(11)
C3 C4 C5 125.16(11)
C3 C4 C10 118.63(11)
C10 C4 C5 116.21(11)
C6 C5 C4 116.41(11)
N1 C6 C5 111.86(10)
C8 C7 C3 121.90(12)
C7 C8 C9 119.18(11)
O2 C8 C7 125.36(12)
O2 C8 C9 115.44(11)
C10 C9 C8 119.12(12)
O3 C9 C8 115.88(11)
O3 C9 C10 124.99(12)
C9 C10 C4 122.40(12)
N1 C13 C14 114.66(11)
C15 C14 C13 117.79(12)
C15 C14 C19 117.42(12)
C19 C14 C13 124.76(11)
C14 C15 C16 122.16(13)
C17 C16 C15 119.42(12)
C16 C17 C18 119.36(13)
O4 C17 C16 124.54(12)
O4 C17 C18 116.10(13)
C19 C18 C17 120.35(13)
C18 C19 C14 121.23(12)
C2 C21 C22 122.35(12)
C2 C21 C28 122.74(12)
C22 C21 C28 114.81(11)
C23 C22 C21 120.59(12)
C23 C22 C27 118.73(13)
C27 C22 C21 120.61(12)
C22 C23 C24 119.94(16)
C25 C24 C23 120.77(16)
C26 C25 C24 119.52(15)
C25 C26 C27 120.71(16)
C26 C27 C22 120.33(15)
C29 C28 C21 113.25(14)
C1 N1 C6 120.11(10)
C1 N1 C13 120.12(11)
C13 N1 C6 117.54(11)
C8 O2 C11 117.30(11)
C9 O3 C12 117.06(12)
C17 O4 C20 117.26(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5111(16)
C1 N1 1.3500(16)
C1 O1 1.2261(15)
C2 C3 1.4944(17)
C2 C21 1.3400(18)
C3 C4 1.3936(17)
C3 C7 1.4099(16)
C4 C5 1.5123(17)
C4 C10 1.4011(18)
C5 C6 1.5116(19)
C6 N1 1.4632(16)
C7 C8 1.3754(18)
C8 C9 1.4045(18)
C8 O2 1.3669(15)
C9 C10 1.3732(18)
C9 O3 1.3666(15)
C11 O2 1.4198(19)
C12 O3 1.414(2)
C13 C14 1.5103(18)
C13 N1 1.4580(16)
C14 C15 1.3805(18)
C14 C19 1.384(2)
C15 C16 1.383(2)
C16 C17 1.379(2)
C17 C18 1.3811(19)
C17 O4 1.3691(17)
C18 C19 1.3802(19)
C20 O4 1.420(2)
C21 C22 1.4949(17)
C21 C28 1.5098(19)
C22 C23 1.3846(19)
C22 C27 1.3913(19)
C23 C24 1.391(2)
C24 C25 1.370(3)
C25 C26 1.366(3)
C26 C27 1.383(2)
C28 C29 1.498(2)
