#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226533.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_2226533
loop_
_publ_author_name
'Xie, Lijun'
'Zhai, Xin'
'Zuo, Jian'
'Zhao, Yanfang'
'Gong, Ping'
_publ_section_title
;
 (1R,3S,4R,4aS,7R,7aS,10R,12aR)-3-Azido-4,7,10-trimethyl-1,10-epidioxyperhydropyrano[4,3-j][1,2]benzodioxepine
;
_journal_coeditor_code           IM2212
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1839
_journal_paper_doi               10.1107/S1600536810024566
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H23 N3 O4'
_chemical_formula_moiety         'C15 H23 N3 O4'
_chemical_formula_sum            'C15 H23 N3 O4'
_chemical_formula_weight         309.36
_chemical_name_systematic
;
(1R,3S,4R,4aS,7R,7aS,10R,
12aR)-3-Azido-4,7,10-trimethyl-1,10-epidioxyperhydropyrano[4,3-
j][1,2]benzodioxepine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9938(9)
_cell_length_b                   11.2070(10)
_cell_length_c                   17.984(2)
_cell_measurement_reflns_used    2309
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.347
_cell_measurement_theta_min      2.265
_cell_volume                     1611.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7585
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0401
_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)+(0.0312P)²+0.4488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                1130
_reflns_number_total             1657
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2212.cif
_cod_data_source_block           I
_cod_database_code               2226533
_cod_database_fobs_code          2226533
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_disorder_assembly
_atom_site_disorder_group
N N1 0.4489(5) 0.4264(3) 0.41235(17) 0.0737(10) Uani d . 1 . .
N N2 0.3162(6) 0.4810(3) 0.41854(19) 0.0756(10) Uani d . 1 . .
N N3 0.2016(6) 0.5395(4) 0.4253(3) 0.1117(15) Uani d . 1 . .
O O1 0.3528(3) 0.3297(2) 0.30143(11) 0.0583(6) Uani d . 1 . .
O O2 0.3573(3) 0.3910(2) 0.18223(12) 0.0601(7) Uani d . 1 . .
O O3 0.4236(3) 0.1895(2) 0.17929(14) 0.0726(8) Uani d . 1 . .
O O4 0.5935(3) 0.2044(2) 0.20749(13) 0.0669(7) Uani d . 1 . .
C C1 0.4297(5) 0.3114(3) 0.37062(18) 0.0656(10) Uani d . 1 . .
H H1 0.3554 0.2601 0.3999 0.079 Uiso calc R 1 . .
C C2 0.5957(5) 0.2491(4) 0.3652(2) 0.0738(12) Uani d . 1 . .
H H2 0.5712 0.1695 0.3454 0.089 Uiso calc R 1 . .
C C3 0.7131(5) 0.3075(4) 0.3087(2) 0.0670(11) Uani d . 1 . .
H H3 0.8021 0.2495 0.2989 0.080 Uiso calc R 1 . .
C C4 0.6214(4) 0.3259(3) 0.23485(17) 0.0528(9) Uani d . 1 . .
C C5 0.4547(4) 0.3878(3) 0.24650(17) 0.0495(9) Uani d . 1 . .
H H5 0.4759 0.4699 0.2627 0.059 Uiso calc R 1 . .
C C6 0.3823(5) 0.2889(4) 0.13467(19) 0.0683(11) Uani d . 1 . .
C C7 0.5171(5) 0.3170(4) 0.0778(2) 0.0789(12) Uani d . 1 . .
H H7A 0.5780 0.2444 0.0667 0.095 Uiso calc R 1 . .
H H7B 0.4638 0.3435 0.0322 0.095 Uiso calc R 1 . .
C C8 0.6406(6) 0.4117(4) 0.1028(2) 0.0765(12) Uani d . 1 . .
H H8A 0.5809 0.4867 0.1075 0.092 Uiso calc R 1 . .
H H8B 0.7234 0.4218 0.0639 0.092 Uiso calc R 1 . .
C C9 0.7325(5) 0.3881(3) 0.1758(2) 0.0653(10) Uani d . 1 . .
H H9 0.8227 0.3319 0.1640 0.078 Uiso calc R 1 . .
C C10 0.8171(5) 0.5007(4) 0.2052(2) 0.0798(12) Uani d . 1 . .
H H10 0.7293 0.5586 0.2172 0.096 Uiso calc R 1 . .
C C11 0.9123(5) 0.4740(5) 0.2759(3) 0.0973(16) Uani d . 1 . .
H H11A 0.9621 0.5470 0.2945 0.117 Uiso calc R 1 . .
H H11B 1.0020 0.4184 0.2650 0.117 Uiso calc R 1 . .
C C12 0.7998(5) 0.4211(4) 0.3354(2) 0.0840(13) Uani d . 1 . .
H H12A 0.7159 0.4795 0.3493 0.101 Uiso calc R 1 . .
H H12B 0.8661 0.4032 0.3791 0.101 Uiso calc R 1 . .
C C13 0.6724(7) 0.2282(5) 0.4424(2) 0.1150(19) Uani d . 1 . .
H H13A 0.6936 0.3037 0.4659 0.173 Uiso calc R 1 . .
H H13B 0.7756 0.1851 0.4374 0.173 Uiso calc R 1 . .
H H13C 0.5960 0.1828 0.4724 0.173 Uiso calc R 1 . .
C C14 0.2153(6) 0.2572(5) 0.1011(3) 0.1060(17) Uani d . 1 . .
H H14A 0.2293 0.1929 0.0665 0.159 Uiso calc R 1 . .
H H14B 0.1704 0.3255 0.0758 0.159 Uiso calc R 1 . .
H H14C 0.1398 0.2332 0.1398 0.159 Uiso calc R 1 . .
C C15 0.9352(6) 0.5587(5) 0.1476(3) 0.124(2) Uani d . 1 . .
H H15A 0.9829 0.6300 0.1683 0.186 Uiso calc R 1 . .
H H15B 0.8730 0.5785 0.1036 0.186 Uiso calc R 1 . .
H H15C 1.0229 0.5038 0.1351 0.186 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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'
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
N2 N1 C1 . . 112.6(3) ?
N3 N2 N1 . . 174.3(4) ?
C1 O1 C5 . . 115.3(3) ?
C5 O2 C6 . . 113.2(3) ?
C6 O3 O4 . . 108.9(3) ?
O3 O4 C4 . . 111.4(2) ?
O1 C1 N1 . . 111.3(3) ?
O1 C1 C2 . . 113.4(3) ?
N1 C1 C2 . . 110.0(3) ?
O1 C1 H1 . . 107.3 ?
N1 C1 H1 . . 107.3 ?
C2 C1 H1 . . 107.3 ?
C1 C2 C3 . . 112.7(3) ?
C1 C2 C13 . . 111.4(3) ?
C3 C2 C13 . . 114.9(4) ?
C1 C2 H2 . . 105.7 ?
C3 C2 H2 . . 105.7 ?
C13 C2 H2 . . 105.7 ?
C12 C3 C2 . . 115.3(3) ?
C12 C3 C4 . . 112.2(3) ?
C2 C3 C4 . . 109.9(3) ?
C12 C3 H3 . . 106.3 ?
C2 C3 H3 . . 106.3 ?
C4 C3 H3 . . 106.3 ?
O4 C4 C5 . . 109.7(3) ?
O4 C4 C3 . . 103.9(3) ?
C5 C4 C3 . . 111.2(3) ?
O4 C4 C9 . . 106.0(3) ?
C5 C4 C9 . . 113.1(3) ?
C3 C4 C9 . . 112.4(3) ?
O2 C5 O1 . . 105.4(3) ?
O2 C5 C4 . . 112.8(3) ?
O1 C5 C4 . . 112.7(3) ?
O2 C5 H5 . . 108.6 ?
O1 C5 H5 . . 108.6 ?
C4 C5 H5 . . 108.6 ?
O3 C6 O2 . . 108.7(3) ?
O3 C6 C14 . . 104.4(4) ?
O2 C6 C14 . . 107.5(3) ?
O3 C6 C7 . . 112.4(3) ?
O2 C6 C7 . . 109.5(3) ?
C14 C6 C7 . . 114.1(3) ?
C8 C7 C6 . . 114.0(3) ?
C8 C7 H7A . . 108.7 ?
C6 C7 H7A . . 108.7 ?
C8 C7 H7B . . 108.7 ?
C6 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C7 C8 C9 . . 116.5(3) ?
C7 C8 H8A . . 108.2 ?
C9 C8 H8A . . 108.2 ?
C7 C8 H8B . . 108.2 ?
C9 C8 H8B . . 108.2 ?
H8A C8 H8B . . 107.3 ?
C10 C9 C8 . . 111.6(3) ?
C10 C9 C4 . . 112.8(3) ?
C8 C9 C4 . . 113.0(3) ?
C10 C9 H9 . . 106.3 ?
C8 C9 H9 . . 106.3 ?
C4 C9 H9 . . 106.3 ?
C11 C10 C9 . . 110.6(4) ?
C11 C10 C15 . . 109.9(4) ?
C9 C10 C15 . . 112.7(4) ?
C11 C10 H10 . . 107.9 ?
C9 C10 H10 . . 107.9 ?
C15 C10 H10 . . 107.9 ?
C10 C11 C12 . . 111.8(3) ?
C10 C11 H11A . . 109.3 ?
C12 C11 H11A . . 109.3 ?
C10 C11 H11B . . 109.3 ?
C12 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C11 C12 C3 . . 111.9(4) ?
C11 C12 H12A . . 109.2 ?
C3 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C3 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C6 C14 H14A . . 109.5 ?
C6 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C6 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10 C15 H15A . . 109.5 ?
C10 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C10 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
N1 N2 . 1.229(5) ?
N1 C1 . 1.499(5) ?
N2 N3 . 1.133(5) ?
O1 C1 . 1.403(4) ?
O1 C5 . 1.437(4) ?
O2 C5 . 1.394(4) ?
O2 C6 . 1.442(4) ?
O3 C6 . 1.412(4) ?
O3 O4 . 1.459(3) ?
O4 C4 . 1.464(4) ?
C1 C2 . 1.503(6) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.530(5) ?
C2 C13 . 1.536(5) ?
C2 H2 . 0.9800 ?
C3 C12 . 1.527(5) ?
C3 C4 . 1.531(4) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.517(5) ?
C4 C9 . 1.550(5) ?
C5 H5 . 0.9800 ?
C6 C14 . 1.507(5) ?
C6 C7 . 1.518(5) ?
C7 C8 . 1.518(6) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.528(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.526(5) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.511(6) ?
C10 C15 . 1.545(6) ?
C10 H10 . 0.9800 ?
C11 C12 . 1.518(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
C7 H7B N3 2_564 0.97 2.68 3.628(6) 166.8
C10 H10 O3 3_655 0.98 2.67 3.535(5) 147.8
C12 H12A O3 3_655 0.97 2.65 3.508(5) 146.9
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
C1 N1 N2 N3 . . . . -159(4) ?
C6 O3 O4 C4 . . . . 44.7(3) ?
C5 O1 C1 N1 . . . . 72.1(4) ?
C5 O1 C1 C2 . . . . -52.6(4) ?
N2 N1 C1 O1 . . . . 53.7(4) ?
N2 N1 C1 C2 . . . . -179.8(3) ?
O1 C1 C2 C3 . . . . 50.7(4) ?
N1 C1 C2 C3 . . . . -74.6(4) ?
O1 C1 C2 C13 . . . . -178.5(4) ?
N1 C1 C2 C13 . . . . 56.2(5) ?
C1 C2 C3 C12 . . . . 78.1(4) ?
C13 C2 C3 C12 . . . . -50.9(5) ?
C1 C2 C3 C4 . . . . -49.8(4) ?
C13 C2 C3 C4 . . . . -178.8(3) ?
O3 O4 C4 C5 . . . . 16.4(3) ?
O3 O4 C4 C3 . . . . 135.4(3) ?
O3 O4 C4 C9 . . . . -106.0(3) ?
C12 C3 C4 O4 . . . . 162.9(3) ?
C2 C3 C4 O4 . . . . -67.5(4) ?
C12 C3 C4 C5 . . . . -79.1(4) ?
C2 C3 C4 C5 . . . . 50.5(4) ?
C12 C3 C4 C9 . . . . 48.8(4) ?
C2 C3 C4 C9 . . . . 178.4(3) ?
C6 O2 C5 O1 . . . . -91.5(3) ?
C6 O2 C5 C4 . . . . 31.9(4) ?
C1 O1 C5 O2 . . . . 177.1(3) ?
C1 O1 C5 C4 . . . . 53.7(4) ?
O4 C4 C5 O2 . . . . -57.1(4) ?
C3 C4 C5 O2 . . . . -171.5(3) ?
C9 C4 C5 O2 . . . . 61.0(4) ?
O4 C4 C5 O1 . . . . 62.1(3) ?
C3 C4 C5 O1 . . . . -52.3(4) ?
C9 C4 C5 O1 . . . . -179.9(3) ?
O4 O3 C6 O2 . . . . -72.3(3) ?
O4 O3 C6 C14 . . . . 173.2(3) ?
O4 O3 C6 C7 . . . . 49.0(4) ?
C5 O2 C6 O3 . . . . 30.7(4) ?
C5 O2 C6 C14 . . . . 143.2(3) ?
C5 O2 C6 C7 . . . . -92.4(3) ?
O3 C6 C7 C8 . . . . -95.2(4) ?
O2 C6 C7 C8 . . . . 25.7(4) ?
C14 C6 C7 C8 . . . . 146.2(4) ?
C6 C7 C8 C9 . . . . 56.2(5) ?
C7 C8 C9 C10 . . . . -165.3(3) ?
C7 C8 C9 C4 . . . . -36.8(5) ?
O4 C4 C9 C10 . . . . -162.7(3) ?
C5 C4 C9 C10 . . . . 77.1(4) ?
C3 C4 C9 C10 . . . . -49.8(4) ?
O4 C4 C9 C8 . . . . 69.6(4) ?
C5 C4 C9 C8 . . . . -50.7(4) ?
C3 C4 C9 C8 . . . . -177.6(3) ?
C8 C9 C10 C11 . . . . -177.9(3) ?
C4 C9 C10 C11 . . . . 53.5(4) ?
C8 C9 C10 C15 . . . . -54.6(5) ?
C4 C9 C10 C15 . . . . 176.9(3) ?
C9 C10 C11 C12 . . . . -57.2(5) ?
C15 C10 C11 C12 . . . . 177.8(4) ?
C10 C11 C12 C3 . . . . 57.2(5) ?
C2 C3 C12 C11 . . . . -179.4(3) ?
C4 C3 C12 C11 . . . . -52.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24690652
