#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/09/2230936.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230936
loop_
_publ_author_name
'Dardouri, Rachida'
'Rodi, Yousef Kandri'
'Saffon, Natalie'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 3-{[3-(4-Methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
;
_journal_coeditor_code           XU5243
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1729
_journal_paper_doi               10.1107/S1600536811022872
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H23 N3 O4'
_chemical_formula_moiety         'C22 H23 N3 O4'
_chemical_formula_sum            'C22 H23 N3 O4'
_chemical_formula_weight         393.43
_chemical_name_systematic
;
3-{[3-(4-Methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}-
1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
;
_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                 93.2350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.0041(5)
_cell_length_b                   15.4644(3)
_cell_length_c                   9.0350(2)
_cell_measurement_reflns_used    5272
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8190
_cell_measurement_theta_min      2.5516
_cell_volume                     3906.52(13)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            30861
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.274
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+5.3445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1785
_reflns_number_gt                2548
_reflns_number_total             3445
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5243.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230936
_cod_database_fobs_code          2230936
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.67566(10) 0.19618(16) 0.5304(3) 0.0852(8) Uani d . 1 1 . .
O O2 0.57207(8) 0.11159(17) 0.2866(3) 0.0770(7) Uani d . 1 1 . .
O O3 0.63939(16) 0.3964(3) 0.2387(4) 0.0605(14) Uani d PDU 0.634(4) 1 A 1
O O4 0.54628(8) 0.85003(14) 0.3904(3) 0.0710(7) Uani d . 1 1 A .
N N1 0.71472(9) 0.14146(16) 0.3388(3) 0.0578(7) Uani d . 1 1 . .
N N2 0.63531(8) 0.07484(15) 0.1556(3) 0.0536(6) Uani d . 1 1 . .
N N3 0.6331(2) 0.4866(4) 0.2330(7) 0.060(2) Uani d PDU 0.634(4) 1 A 1
C C1 0.67932(11) 0.09694(18) 0.0955(3) 0.0523(7) Uani d . 1 1 . .
C C2 0.68467(17) 0.0844(3) -0.0552(4) 0.0855(12) Uani d . 1 1 . .
H H2 0.6590 0.0641 -0.1152 0.103 Uiso calc R 1 1 . .
C C3 0.7269(3) 0.1015(3) -0.1157(6) 0.119(2) Uani d . 1 1 . .
H H3 0.7296 0.0928 -0.2167 0.143 Uiso calc R 1 1 . .
C C4 0.7656(2) 0.1314(3) -0.0313(7) 0.117(2) Uani d . 1 1 . .
H H4 0.7946 0.1413 -0.0738 0.141 Uiso calc R 1 1 . .
C C5 0.76090(14) 0.1467(2) 0.1191(5) 0.0880(13) Uani d . 1 1 . .
H H5 0.7865 0.1691 0.1768 0.106 Uiso calc R 1 1 . .
C C6 0.71793(11) 0.12863(18) 0.1834(3) 0.0542(8) Uani d . 1 1 . .
C C7 0.61090(12) -0.0048(2) 0.1047(4) 0.0737(10) Uani d . 1 1 . .
H H7A 0.5898 -0.0238 0.1783 0.111 Uiso calc R 1 1 . .
H H7B 0.6342 -0.0489 0.0892 0.111 Uiso calc R 1 1 . .
H H7C 0.5928 0.0064 0.0134 0.111 Uiso calc R 1 1 . .
C C8 0.61146(11) 0.1295(2) 0.2423(3) 0.0554(8) Uani d . 1 1 A .
C C9 0.63728(13) 0.21183(18) 0.2874(4) 0.0650(9) Uani d D 1 1 . .
H H9 0.6512 0.2368 0.1999 0.078 Uiso calc PR 0.634(4) 1 A 1
H H9' 0.6510 0.2375 0.2002 0.078 Uiso calc PR 0.366(4) 1 A 2
C C10 0.67758(12) 0.18422(18) 0.3971(4) 0.0602(8) Uani d . 1 1 A .
C C11 0.75503(13) 0.1155(3) 0.4405(5) 0.0895(12) Uani d . 1 1 . .
H H11A 0.7430 0.0928 0.5300 0.134 Uiso calc R 1 1 . .
H H11B 0.7749 0.1648 0.4635 0.134 Uiso calc R 1 1 . .
H H11C 0.7735 0.0718 0.3942 0.134 Uiso calc R 1 1 . .
C C12 0.59677(16) 0.2732(3) 0.3369(6) 0.0481(11) Uani d PDU 0.634(4) 1 A 1
H H12A 0.5712 0.2755 0.2599 0.058 Uiso calc PR 0.634(4) 1 A 1
H H12B 0.5836 0.2506 0.4261 0.058 Uiso calc PR 0.634(4) 1 A 1
C C13 0.61609(16) 0.3625(3) 0.3660(5) 0.0512(10) Uani d PDU 0.634(4) 1 A 1
H H13 0.6381 0.3630 0.4544 0.061 Uiso calc PR 0.634(4) 1 A 1
C C14 0.57479(7) 0.42592(11) 0.3838(2) 0.0855(13) Uani d PDU 0.634(4) 1 A 1
H H14A 0.5455 0.4069 0.3312 0.103 Uiso calc PR 0.634(4) 1 A 1
H H14B 0.5690 0.4365 0.4870 0.103 Uiso calc PR 0.634(4) 1 A 1
C C15 0.59627(7) 0.50273(11) 0.3118(2) 0.0683(10) Uani d RD 1 1 . .
C C16 0.58267(7) 0.59290(11) 0.3351(2) 0.0551(8) Uani d R 1 1 A .
C C17 0.54373(7) 0.61376(11) 0.4159(2) 0.0683(10) Uani d R 1 1 . .
H H17 0.5262 0.5696 0.4569 0.082 Uiso calc R 1 1 . .
C C18 0.53026(11) 0.6984(2) 0.4372(3) 0.0610(8) Uani d . 1 1 A .
H H18 0.5038 0.7110 0.4911 0.073 Uiso calc R 1 1 . .
C C19 0.55629(10) 0.76409(19) 0.3782(3) 0.0533(7) Uani d . 1 1 . .
C C20 0.59550(10) 0.7442(2) 0.2959(3) 0.0551(7) Uani d . 1 1 A .
H H20 0.6132 0.7884 0.2555 0.066 Uiso calc R 1 1 . .
C C21 0.60796(10) 0.6603(2) 0.2746(3) 0.0547(7) Uani d . 1 1 . .
H H21 0.6339 0.6478 0.2185 0.066 Uiso calc R 1 1 A .
C C22 0.50391(11) 0.8728(2) 0.4642(5) 0.0783(11) Uani d . 1 1 . .
H H22A 0.5006 0.9346 0.4656 0.117 Uiso calc R 1 1 A .
H H22B 0.5064 0.8514 0.5640 0.117 Uiso calc R 1 1 . .
H H22C 0.4765 0.8477 0.4121 0.117 Uiso calc R 1 1 . .
O O3' 0.6240(3) 0.3830(6) 0.1858(9) 0.0605(14) Uani d PD 0.37 1 A 2
N N3' 0.6197(5) 0.4734(7) 0.2005(15) 0.060(2) Uani d PD 0.37 1 A 2
C C12' 0.6199(3) 0.2846(5) 0.3878(9) 0.0481(11) Uani d PD 0.37 1 A 2
H H12C 0.6000 0.2615 0.4631 0.058 Uiso calc PR 0.366(4) 1 A 2
H H12D 0.6467 0.3151 0.4360 0.058 Uiso calc PR 0.366(4) 1 A 2
C C13' 0.5914(3) 0.3432(4) 0.2836(8) 0.0512(10) Uani d PD 0.37 1 A 2
H H13' 0.5647 0.3136 0.2302 0.061 Uiso calc PR 0.366(4) 1 A 2
C C14' 0.5746(4) 0.4238(4) 0.3791(12) 0.0855(13) Uani d PD 0.37 1 A 2
H H14C 0.5400 0.4280 0.3741 0.103 Uiso calc PR 0.366(4) 1 A 2
H H14D 0.5858 0.4176 0.4821 0.103 Uiso calc PR 0.366(4) 1 A 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 O3 C13 . . 109.0(4) ?
C19 O4 C22 . . 117.1(3) ?
C10 N1 C6 . . 122.7(3) ?
C10 N1 C11 . . 117.8(3) ?
C6 N1 C11 . . 119.2(3) ?
C8 N2 C1 . . 122.6(3) ?
C8 N2 C7 . . 117.9(3) ?
C1 N2 C7 . . 118.8(2) ?
C15 N3 O3 . . 105.6(5) ?
C6 C1 C2 . . 118.9(3) ?
C6 C1 N2 . . 122.0(2) ?
C2 C1 N2 . . 119.0(3) ?
C3 C2 C1 . . 120.7(5) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 121.5(5) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C3 C4 C5 . . 119.0(4) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C6 . . 120.3(5) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.5(3) ?
C1 C6 N1 . . 121.3(2) ?
C5 C6 N1 . . 119.1(3) ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 N2 . . 122.0(3) ?
O2 C8 C9 . . 121.9(3) ?
N2 C8 C9 . . 116.0(3) ?
C8 C9 C10 . . 105.4(2) ?
C8 C9 C12' . . 127.7(4) ?
C10 C9 C12' . . 93.9(4) ?
C8 C9 C12 . . 104.2(3) ?
C10 C9 C12 . . 120.5(3) ?
C8 C9 H9 . . 108.7 ?
C10 C9 H9 . . 108.7 ?
C12' C9 H9 . . 110.0 ?
C12 C9 H9 . . 108.7 ?
C8 C9 H9' . . 109.2 ?
C10 C9 H9' . . 109.2 ?
C12' C9 H9' . . 109.2 ?
C12 C9 H9' . . 107.9 ?
O1 C10 N1 . . 122.1(3) ?
O1 C10 C9 . . 121.9(3) ?
N1 C10 C9 . . 116.0(3) ?
N1 C11 H11A . . 109.5 ?
N1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C9 . . 110.4(3) ?
C13 C12 H12A . . 109.6 ?
C9 C12 H12A . . 109.6 ?
C13 C12 H12B . . 109.6 ?
C9 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
O3 C13 C12 . . 111.5(4) ?
O3 C13 C14 . . 103.2(3) ?
C12 C13 C14 . . 109.9(3) ?
O3 C13 H13 . . 110.7 ?
C12 C13 H13 . . 110.7 ?
C14 C13 H13 . . 110.7 ?
C15 C14 C13 . . 97.93(17) ?
C15 C14 H14A . . 112.2 ?
C13 C14 H14A . . 112.2 ?
C15 C14 H14B . . 112.2 ?
C13 C14 H14B . . 112.2 ?
H14A C14 H14B . . 109.8 ?
N3 C15 C16 . . 118.6(3) ?
N3' C15 C16 . . 125.8(5) ?
N3 C15 C14 . . 115.7(3) ?
N3' C15 C14 . . 106.8(5) ?
C16 C15 C14 . . 125.4 ?
N3' C15 C14' . . 105.1(6) ?
C16 C15 C14' . . 126.8(3) ?
C17 C16 C21 . . 117.81(13) ?
C17 C16 C15 . . 121.1 ?
C21 C16 C15 . . 121.05(13) ?
C18 C17 C16 . . 121.65(14) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C17 C18 C19 . . 119.5(2) ?
C17 C18 H18 . . 120.3 ?
C19 C18 H18 . . 120.3 ?
O4 C19 C18 . . 124.9(3) ?
O4 C19 C20 . . 115.5(3) ?
C18 C19 C20 . . 119.6(3) ?
C21 C20 C19 . . 120.1(3) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C20 C21 C16 . . 121.3(2) ?
C20 C21 H21 . . 119.3 ?
C16 C21 H21 . . 119.3 ?
O4 C22 H22A . . 109.5 ?
O4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N3' O3' C13' . . 107.8(8) ?
C15 N3' O3' . . 117.6(9) ?
C13' C12' C9 . . 104.2(5) ?
C13' C12' H12C . . 110.9 ?
C9 C12' H12C . . 110.9 ?
C13' C12' H12D . . 110.9 ?
C9 C12' H12D . . 110.9 ?
H12C C12' H12D . . 108.9 ?
O3' C13' C12' . . 108.1(7) ?
O3' C13' C14' . . 102.4(6) ?
C12' C13' C14' . . 107.1(7) ?
O3' C13' H13' . . 112.9 ?
C12' C13' H13' . . 112.9 ?
C14' C13' H13' . . 112.9 ?
C15 C14' C13' . . 105.9(5) ?
C15 C14' H14D . . 110.5 ?
C13' C14' H14D . . 110.5 ?
C15 C14' H14C . . 110.5 ?
C13' C14' H14D . . 110.5 ?
H14C C14' H14D . . 108.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.222(4) ?
O2 C8 . 1.226(3) ?
O3 N3 . 1.407(5) ?
O3 C13 . 1.451(5) ?
O4 C19 . 1.364(3) ?
O4 C22 . 1.437(4) ?
N1 C10 . 1.364(4) ?
N1 C6 . 1.426(4) ?
N1 C11 . 1.470(4) ?
N2 C8 . 1.354(4) ?
N2 C1 . 1.416(4) ?
N2 C7 . 1.469(4) ?
N3 C15 . 1.309(5) ?
C1 C6 . 1.394(4) ?
C1 C2 . 1.392(4) ?
C2 C3 . 1.356(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.393(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.394(4) ?
C5 H5 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.508(5) ?
C9 C10 . 1.521(5) ?
C9 C12' . 1.541(7) ?
C9 C12 . 1.564(5) ?
C9 H9 . 0.9800 ?
C9 H9' . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.502(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.531(4) ?
C13 H13 . 0.9800 ?
C14 C15 . 1.4965 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 N3' . 1.313(8) ?
C15 C16 . 1.4638 ?
C15 C14' . 1.507(7) ?
C16 C17 . 1.3846 ?
C16 C21 . 1.390(3) ?
C17 C18 . 1.379(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.376(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.395(4) ?
C20 C21 . 1.360(4) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
O3' N3' . 1.410(8) ?
O3' C13' . 1.442(8) ?
C12' C13' . 1.503(8) ?
C12' H12C . 0.9700 ?
C12' H12D . 0.9700 ?
C13' C14' . 1.602(8) ?
C13' H13' . 0.9800 ?
C14' H14C . 0.9700 ?
C14' H14D . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4 O3 7_655 0.93 2.51 3.367(7) 154
C11 H11B O1 7_656 0.96 2.56 3.501(5) 168
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 O3 N3 C15 . . . . -20.5(6) ?
C8 N2 C1 C6 . . . . 51.7(4) ?
C7 N2 C1 C6 . . . . -137.7(3) ?
C8 N2 C1 C2 . . . . -130.1(3) ?
C7 N2 C1 C2 . . . . 40.5(4) ?
C6 C1 C2 C3 . . . . 0.9(5) ?
N2 C1 C2 C3 . . . . -177.3(3) ?
C1 C2 C3 C4 . . . . 0.1(7) ?
C2 C3 C4 C5 . . . . -1.8(7) ?
C3 C4 C5 C6 . . . . 2.5(6) ?
C2 C1 C6 C5 . . . . -0.2(4) ?
N2 C1 C6 C5 . . . . 178.0(3) ?
C2 C1 C6 N1 . . . . -179.0(3) ?
N2 C1 C6 N1 . . . . -0.8(4) ?
C4 C5 C6 C1 . . . . -1.5(5) ?
C4 C5 C6 N1 . . . . 177.4(3) ?
C10 N1 C6 C1 . . . . -48.7(4) ?
C11 N1 C6 C1 . . . . 137.5(3) ?
C10 N1 C6 C5 . . . . 132.5(3) ?
C11 N1 C6 C5 . . . . -41.3(4) ?
C1 N2 C8 O2 . . . . 175.7(3) ?
C7 N2 C8 O2 . . . . 5.0(4) ?
C1 N2 C8 C9 . . . . -7.3(4) ?
C7 N2 C8 C9 . . . . -177.9(3) ?
O2 C8 C9 C10 . . . . 106.4(3) ?
N2 C8 C9 C10 . . . . -70.6(3) ?
O2 C8 C9 C12' . . . . -1.3(6) ?
N2 C8 C9 C12' . . . . -178.3(4) ?
O2 C8 C9 C12 . . . . -21.4(4) ?
N2 C8 C9 C12 . . . . 161.6(3) ?
C6 N1 C10 O1 . . . . -178.6(3) ?
C11 N1 C10 O1 . . . . -4.8(4) ?
C6 N1 C10 C9 . . . . 4.6(4) ?
C11 N1 C10 C9 . . . . 178.5(3) ?
C8 C9 C10 O1 . . . . -104.6(3) ?
C12' C9 C10 O1 . . . . 26.3(5) ?
C12 C9 C10 O1 . . . . 12.6(4) ?
C8 C9 C10 N1 . . . . 72.1(3) ?
C12' C9 C10 N1 . . . . -156.9(4) ?
C12 C9 C10 N1 . . . . -170.7(3) ?
C8 C9 C12 C13 . . . . -172.4(3) ?
C10 C9 C12 C13 . . . . 69.8(5) ?
C12' C9 C12 C13 . . . . 41.0(7) ?
N3 O3 C13 C12 . . . . 147.7(5) ?
N3 O3 C13 C14 . . . . 29.7(5) ?
C9 C12 C13 O3 . . . . 54.9(5) ?
C9 C12 C13 C14 . . . . 168.7(3) ?
O3 C13 C14 C15 . . . . -25.3(3) ?
C12 C13 C14 C15 . . . . -144.4(3) ?
O3 N3 C15 N3' . . . . -69(2) ?
O3 N3 C15 C16 . . . . 176.0(3) ?
O3 N3 C15 C14 . . . . 2.1(6) ?
O3 N3 C15 C14' . . . . 0.4(8) ?
C13 C14 C15 N3 . . . . 15.3(4) ?
C13 C14 C15 N3' . . . . 37.2(8) ?
C13 C14 C15 C16 . . . . -158.1(2) ?
C13 C14 C15 C14' . . . . 66(13) ?
N3 C15 C16 C17 . . . . 179.2(4) ?
N3' C15 C16 C17 . . . . 154.3(9) ?
C14 C15 C16 C17 . . . . -7.6 ?
C14' C15 C16 C17 . . . . -5.8(7) ?
N3 C15 C16 C21 . . . . 0.3(4) ?
N3' C15 C16 C21 . . . . -24.6(9) ?
C14 C15 C16 C21 . . . . 173.52(17) ?
C14' C15 C16 C21 . . . . 175.2(7) ?
C21 C16 C17 C18 . . . . -0.3(2) ?
C15 C16 C17 C18 . . . . -179.28(19) ?
C16 C17 C18 C19 . . . . -0.6(4) ?
C22 O4 C19 C18 . . . . -3.4(4) ?
C22 O4 C19 C20 . . . . 175.1(3) ?
C17 C18 C19 O4 . . . . 179.3(3) ?
C17 C18 C19 C20 . . . . 0.9(5) ?
O4 C19 C20 C21 . . . . -178.8(3) ?
C18 C19 C20 C21 . . . . -0.2(4) ?
C19 C20 C21 C16 . . . . -0.8(4) ?
C17 C16 C21 C20 . . . . 1.1(3) ?
C15 C16 C21 C20 . . . . -180.0(2) ?
N3 C15 N3' O3' . . . . 110(3) ?
C16 C15 N3' O3' . . . . -171.5(8) ?
C14 C15 N3' O3' . . . . -6.9(14) ?
C14' C15 N3' O3' . . . . -7.9(15) ?
C13' O3' N3' C15 . . . . 12.3(16) ?
C8 C9 C12' C13' . . . . -87.0(7) ?
C10 C9 C12' C13' . . . . 160.0(6) ?
C12 C9 C12' C13' . . . . -44.5(6) ?
N3' O3' C13' C12' . . . . -122.7(10) ?
N3' O3' C13' C14' . . . . -9.9(11) ?
C9 C12' C13' O3' . . . . -67.2(8) ?
C9 C12' C13' C14' . . . . -176.8(6) ?
N3 C15 C14' C13' . . . . -20.7(10) ?
N3' C15 C14' C13' . . . . 0.8(12) ?
C16 C15 C14' C13' . . . . 164.2(4) ?
C14 C15 C14' C13' . . . . -151(13) ?
O3' C13' C14' C15 . . . . 5.7(10) ?
C12' C13' C14' C15 . . . . 119.3(8) ?
