##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method
                       'from SHELXL97 CIF aIt is very nd IUCr SHELXL97-template'
_journal_date_recd_electronic     2016-08-12
_journal_date_accepted     2016-09-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue     10
_journal_page_first     1429
_journal_page_last     1433
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016014420
_journal_coeditor_code     ZS2368
_publ_contact_author_name     'Victo N. Khrustalev'
_publ_contact_author_address
;
Inorganic Chemistry Department,
Peoples' Friendship University of Russia (RUDN University),
6 Miklukho-Maklay St., Moscow 117198, Russian Federation
;
_publ_contact_author_email     'vnkhrustalev@gmail.com'
_publ_contact_author_fax     '+7-495-4339588'
_publ_contact_author_phone     '+7-495-9550976'
_publ_section_title
;\
Crystal structures of the two epimers from the unusual thermal C6-epimerization
of
5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-\
6-carboxylic acid,
5a(RS),6(SR),7(RS),9a(SR),9b(SR) and
5a(RS),6(RS),7(RS),9a(SR),9b(SR)
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Dmitry S. Poplevin' .
;
Organic Chemistry Department,
Peoples' Friendship University of Russia (RUDN University),
6 Miklukho-Maklay St., Moscow 117198, Russian Federation
;
    'Fedor I. Zubkov' .
;
Organic Chemistry Department,
Peoples' Friendship University of Russia (RUDN University),
6 Miklukho-Maklay St., Moscow 117198, Russian Federation
;
    'Pavel V. Dorovatovskii' .
;
National Research Centre "Kurchatov Institute",
1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation
;
    'Yan V. Zubavichus' .
;
National Research Centre "Kurchatov Institute",
1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation
;
    'Victor N. Khrustalev' .
;
Inorganic Chemistry Department,
Peoples' Friendship University of Russia (RUDN University),
6 Miklukho-Maklay St., Moscow 117198, Russian Federation
X-Ray Structural Centre,
A.N. Nesmeyanov Institute of Organoelement Compounds,
Russian Academy of Sciences,
28 Vavilov St., B--334, Moscow 119991, Russian Federation
;
_publ_section_synopsis
;\
The two epimers from the unusual thermal C6-epimerization of
5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-\
carboxylic acid,
5a(RS),6(SR),7(RS),9a(SR),9b(SR) and
5a(RS),6(RS),7(RS),9a(SR),9b(SR) have
similar geometries but differ in their hydrogen-bonded crystal-packing modes
;
data_Ia
_database_code_depnum_ccdc_archive 'CCDC 1503859'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;\
5a(RS),6(SR),7(RS),9a(SR),\
9b(SR)-5-Oxo-1,2,3,5,5a,6,7,9b-octahydro-\
7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H13 N O4'
_chemical_formula_sum     'C12 H13 N O4'
_chemical_formula_iupac     'C12 H13 N O4'
_chemical_formula_weight     235.23
_chemical_melting_point_gt     413
_chemical_melting_point_lt     414
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.045(2)
_cell_length_b     9.2023(18)
_cell_length_c     11.062(2)
_cell_angle_alpha     90
_cell_angle_beta     100.91(3)
_cell_angle_gamma     90
_cell_volume     1104.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     600
_cell_measurement_theta_min     4.5
_cell_measurement_theta_max     38.0
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.415
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     0.229
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SCALA; Evans, 2006)
;
_shelx_estimated_absorpt_T_min     0.952
_shelx_estimated_absorpt_T_max     0.963
_exptl_absorpt_correction_T_min     0.950
_exptl_absorpt_correction_T_max     0.960
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_measurement_device_type     'MAR CCD'
_diffrn_measurement_method     'φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12183
_diffrn_reflns_av_R_equivalents     0.0854
_diffrn_reflns_theta_min     4.448
_diffrn_reflns_theta_max     38.472
_diffrn_reflns_theta_full     35.587
_diffrn_measured_fraction_theta_max     0.954
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details     ?
_reflns_number_total     2329
_reflns_number_gt     1864
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0838
_refine_ls_R_factor_gt     0.0718
_refine_ls_wR_factor_gt     0.1757
_refine_ls_wR_factor_ref     0.1890
_refine_ls_goodness_of_fit_ref     1.016
_refine_ls_restrained_S_all     1.016
_refine_ls_number_reflns     2329
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                   'w=1/[σ²(Fo²)+(0.08P)²+1.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.425
_refine_diff_density_min     -0.433
_refine_ls_extinction_method
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.104(9)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0070 0.0030
                         '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' 0.0130 0.0070
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0210 0.0120
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
Automar (MarXperts, 2015)
;
_computing_cell_refinement
;
iMosflm (Battye et al., 2011)
;
_computing_data_reduction
;
iMosflm (Battye et al., 2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.8345(2) 0.9330(3) 0.5467(2) 0.0330(6) Uani d 1 . .
    H H1A 0.8888 0.8929 0.4933 0.040 Uiso calc 1 . .
    H H1B 0.8859 0.9780 0.6202 0.040 Uiso calc 1 . .
    C C2 0.7415(2) 1.0430(3) 0.4762(2) 0.0349(6) Uani d 1 . .
    H H2A 0.7799 1.1002 0.4177 0.042 Uiso calc 1 . .
    H H2B 0.7123 1.1106 0.5341 0.042 Uiso calc 1 . .
    C C3 0.6333(2) 0.9507(3) 0.4064(2) 0.0312(6) Uani d 1 . .
    H H3A 0.5531 0.9989 0.4059 0.037 Uiso calc 1 . .
    H H3B 0.6426 0.9320 0.3205 0.037 Uiso calc 1 . .
    N N4 0.64418(17) 0.8166(2) 0.47832(17) 0.0272(5) Uani d 1 . .
    C C5 0.60154(19) 0.6839(2) 0.4418(2) 0.0253(5) Uani d 1 . .
    O O5 0.52224(14) 0.65677(18) 0.34888(14) 0.0280(5) Uani d 1 . .
    C C5A 0.66529(19) 0.5736(2) 0.53586(19) 0.0236(5) Uani d 1 . .
    H H5A 0.6166 0.5553 0.6019 0.028 Uiso calc 1 . .
    C C6 0.7153(2) 0.4306(2) 0.4908(2) 0.0254(5) Uani d 1 . .
    H H6 0.7007 0.3500 0.5470 0.030 Uiso calc 1 . .
    C C7 0.8561(2) 0.4655(3) 0.5143(2) 0.0296(6) Uani d 1 . .
    H H7 0.9050 0.4068 0.4645 0.035 Uiso calc 1 . .
    C C8 0.9021(2) 0.4591(3) 0.6528(2) 0.0330(6) Uani d 1 . .
    H H8 0.9504 0.3847 0.6980 0.040 Uiso calc 1 . .
    C C9 0.8604(2) 0.5799(3) 0.6976(2) 0.0302(6) Uani d 1 . .
    H H9 0.8737 0.6103 0.7812 0.036 Uiso calc 1 . .
    C C9A 0.7874(2) 0.6583(2) 0.5868(2) 0.0251(5) Uani d 1 . .
    C C9B 0.7500(2) 0.8164(3) 0.5827(2) 0.0291(6) Uani d 1 . .
    H H9B 0.7224 0.8442 0.6606 0.035 Uiso calc 1 . .
    O O10 0.85603(14) 0.62038(18) 0.49215(14) 0.0276(4) Uani d 1 . .
    C C11 0.6649(2) 0.3852(2) 0.3585(2) 0.0251(5) Uani d 1 . .
    O O11 0.71540(16) 0.4123(2) 0.27256(16) 0.0374(5) Uani d 1 . .
    O O12 0.56401(14) 0.30469(18) 0.35042(15) 0.0265(4) Uani d 1 . .
    H H12 0.539(3) 0.275(3) 0.272(3) 0.040 Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 C9B . 1.524(4) ?
    C1 C2 . 1.544(3) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.548(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 N4 . 1.461(3) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    N4 C5 . 1.343(3) ?
    N4 C9B . 1.480(3) ?
    C5 O5 . 1.243(3) ?
    C5 C5A . 1.527(3) ?
    C5A C6 . 1.546(3) ?
    C5A C9A . 1.568(3) ?
    C5A H5A . 1.0000 ?
    C6 C11 . 1.522(3) ?
    C6 C7 . 1.561(3) ?
    C6 H6 . 1.0000 ?
    C7 O10 . 1.446(3) ?
    C7 C8 . 1.522(3) ?
    C7 H7 . 1.0000 ?
    C8 C9 . 1.334(4) ?
    C8 H8 . 0.9500 ?
    C9 C9A . 1.516(3) ?
    C9 H9 . 0.9500 ?
    C9A O10 . 1.447(3) ?
    C9A C9B . 1.511(3) ?
    C9B H9B . 1.0000 ?
    C11 O11 . 1.216(3) ?
    C11 O12 . 1.327(3) ?
    O12 H12 . 0.90(3) ?
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
    C9B C1 C2 . . 102.2(2) ?
    C9B C1 H1A . . 111.3 ?
    C2 C1 H1A . . 111.3 ?
    C9B C1 H1B . . 111.3 ?
    C2 C1 H1B . . 111.3 ?
    H1A C1 H1B . . 109.2 ?
    C1 C2 C3 . . 105.63(19) ?
    C1 C2 H2A . . 110.6 ?
    C3 C2 H2A . . 110.6 ?
    C1 C2 H2B . . 110.6 ?
    C3 C2 H2B . . 110.6 ?
    H2A C2 H2B . . 108.7 ?
    N4 C3 C2 . . 102.45(18) ?
    N4 C3 H3A . . 111.3 ?
    C2 C3 H3A . . 111.3 ?
    N4 C3 H3B . . 111.3 ?
    C2 C3 H3B . . 111.3 ?
    H3A C3 H3B . . 109.2 ?
    C5 N4 C3 . . 128.07(19) ?
    C5 N4 C9B . . 114.43(18) ?
    C3 N4 C9B . . 113.42(18) ?
    O5 C5 N4 . . 125.7(2) ?
    O5 C5 C5A . . 126.3(2) ?
    N4 C5 C5A . . 108.04(17) ?
    C5 C5A C6 . . 119.56(18) ?
    C5 C5A C9A . . 99.73(17) ?
    C6 C5A C9A . . 101.74(17) ?
    C5 C5A H5A . . 111.5 ?
    C6 C5A H5A . . 111.5 ?
    C9A C5A H5A . . 111.5 ?
    C11 C6 C5A . . 117.10(17) ?
    C11 C6 C7 . . 112.8(2) ?
    C5A C6 C7 . . 100.16(17) ?
    C11 C6 H6 . . 108.8 ?
    C5A C6 H6 . . 108.8 ?
    C7 C6 H6 . . 108.8 ?
    O10 C7 C8 . . 101.44(18) ?
    O10 C7 C6 . . 101.91(17) ?
    C8 C7 C6 . . 107.0(2) ?
    O10 C7 H7 . . 115.0 ?
    C8 C7 H7 . . 115.0 ?
    C6 C7 H7 . . 115.0 ?
    C9 C8 C7 . . 105.6(2) ?
    C9 C8 H8 . . 127.2 ?
    C7 C8 H8 . . 127.2 ?
    C8 C9 C9A . . 105.3(2) ?
    C8 C9 H9 . . 127.3 ?
    C9A C9 H9 . . 127.3 ?
    O10 C9A C9B . . 112.83(19) ?
    O10 C9A C9 . . 101.49(18) ?
    C9B C9A C9 . . 125.67(19) ?
    O10 C9A C5A . . 98.78(16) ?
    C9B C9A C5A . . 104.85(17) ?
    C9 C9A C5A . . 110.12(18) ?
    N4 C9B C9A . . 101.29(17) ?
    N4 C9B C1 . . 103.16(18) ?
    C9A C9B C1 . . 120.6(2) ?
    N4 C9B H9B . . 110.3 ?
    C9A C9B H9B . . 110.3 ?
    C1 C9B H9B . . 110.3 ?
    C7 O10 C9A . . 95.65(17) ?
    O11 C11 O12 . . 124.4(2) ?
    O11 C11 C6 . . 123.9(2) ?
    O12 C11 C6 . . 111.56(19) ?
    C11 O12 H12 . . 109.4(19) ?
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
    C9B C1 C2 C3 . . . . -35.5(3) ?
    C1 C2 C3 N4 . . . . 23.1(3) ?
    C2 C3 N4 C5 . . . . -157.3(2) ?
    C2 C3 N4 C9B . . . . -1.6(3) ?
    C3 N4 C5 O5 . . . . -16.7(4) ?
    C9B N4 C5 O5 . . . . -172.2(2) ?
    C3 N4 C5 C5A . . . . 164.6(2) ?
    C9B N4 C5 C5A . . . . 9.0(3) ?
    O5 C5 C5A C6 . . . . 45.6(3) ?
    N4 C5 C5A C6 . . . . -135.7(2) ?
    O5 C5 C5A C9A . . . . 155.1(2) ?
    N4 C5 C5A C9A . . . . -26.1(2) ?
    C5 C5A C6 C11 . . . . -18.4(3) ?
    C9A C5A C6 C11 . . . . -126.8(2) ?
    C5 C5A C6 C7 . . . . 103.9(2) ?
    C9A C5A C6 C7 . . . . -4.5(2) ?
    C11 C6 C7 O10 . . . . 92.5(2) ?
    C5A C6 C7 O10 . . . . -32.8(2) ?
    C11 C6 C7 C8 . . . . -161.48(19) ?
    C5A C6 C7 C8 . . . . 73.2(2) ?
    O10 C7 C8 C9 . . . . 32.0(3) ?
    C6 C7 C8 C9 . . . . -74.4(2) ?
    C7 C8 C9 C9A . . . . 0.9(3) ?
    C8 C9 C9A O10 . . . . -33.6(2) ?
    C8 C9 C9A C9B . . . . -162.9(2) ?
    C8 C9 C9A C5A . . . . 70.3(3) ?
    C5 C5A C9A O10 . . . . -82.84(18) ?
    C6 C5A C9A O10 . . . . 40.32(19) ?
    C5 C5A C9A C9B . . . . 33.7(2) ?
    C6 C5A C9A C9B . . . . 156.88(18) ?
    C5 C5A C9A C9 . . . . 171.42(19) ?
    C6 C5A C9A C9 . . . . -65.4(2) ?
    C5 N4 C9B C9A . . . . 13.2(3) ?
    C3 N4 C9B C9A . . . . -146.0(2) ?
    C5 N4 C9B C1 . . . . 138.6(2) ?
    C3 N4 C9B C1 . . . . -20.6(3) ?
    O10 C9A C9B N4 . . . . 77.5(2) ?
    C9 C9A C9B N4 . . . . -157.9(2) ?
    C5A C9A C9B N4 . . . . -29.0(2) ?
    O10 C9A C9B C1 . . . . -35.3(3) ?
    C9 C9A C9B C1 . . . . 89.3(3) ?
    C5A C9A C9B C1 . . . . -141.8(2) ?
    C2 C1 C9B N4 . . . . 33.3(2) ?
    C2 C1 C9B C9A . . . . 145.2(2) ?
    C8 C7 O10 C9A . . . . -50.66(19) ?
    C6 C7 O10 C9A . . . . 59.66(18) ?
    C9B C9A O10 C7 . . . . -171.63(16) ?
    C9 C9A O10 C7 . . . . 51.38(18) ?
    C5A C9A O10 C7 . . . . -61.36(16) ?
    C5A C6 C11 O11 . . . . 95.3(3) ?
    C7 C6 C11 O11 . . . . -20.2(3) ?
    C5A C6 C11 O12 . . . . -88.8(2) ?
    C7 C6 C11 O12 . . . . 155.70(19) ?
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
    O12 H12 O5 2_645 0.90(3) 1.75(3) 2.613(2) 157(3)
    C5A H5A O12 3_666 1.00 2.51 3.234(3) 129
_shelxl_version_number     2014/6
data_IIa
_database_code_depnum_ccdc_archive 'CCDC 1503860'
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;\
5a(RS),6(RS),7(RS),9a(SR),\
9b(SR)-5-Oxo-1,2,3,5,5a,6,7,9b-octahydro-\
7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H13 N O4'
_chemical_formula_sum     'C12 H13 N O4'
_chemical_formula_weight     235.23
_chemical_melting_point_gt     414
_chemical_melting_point_lt     416
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.4700(17)
_cell_length_b     8.5100(17)
_cell_length_c     8.5900(17)
_cell_angle_alpha     94.04(3)
_cell_angle_beta     111.12(3)
_cell_angle_gamma     105.17(3)
_cell_volume     548.0(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     500
_cell_measurement_theta_min     3.6
_cell_measurement_theta_max     36.0
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.426
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     248
_exptl_absorpt_coefficient_mu     0.230
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SCALA; Evans, 2006)
;
_shelx_estimated_absorpt_T_min     0.963
_shelx_estimated_absorpt_T_max     0.975
_exptl_absorpt_correction_T_min     0.960
_exptl_absorpt_correction_T_max     0.969
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_measurement_device_type     'MAR CCD'
_diffrn_measurement_method     'φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7090
_diffrn_reflns_av_R_equivalents     0.0612
_diffrn_reflns_theta_min     3.443
_diffrn_reflns_theta_max     38.131
_diffrn_reflns_theta_full     35.587
_diffrn_measured_fraction_theta_max     0.890
_diffrn_measured_fraction_theta_full     0.941
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_refine_special_details     ?
_reflns_number_total     2104
_reflns_number_gt     1402
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1278
_refine_ls_R_factor_gt     0.0988
_refine_ls_wR_factor_gt     0.2098
_refine_ls_wR_factor_ref     0.2404
_refine_ls_goodness_of_fit_ref     0.928
_refine_ls_restrained_S_all     0.928
_refine_ls_number_reflns     2104
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                        'w=1/[σ²(Fo²)+(0.06P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.454
_refine_diff_density_min     -0.359
_refine_ls_extinction_method
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.138(11)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0070 0.0030
                         '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' 0.0130 0.0070
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0210 0.0120
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
Automar (MarXperts, 2015)
;
_computing_cell_refinement
;
iMosflm (Battye et al., 2011)
;
_computing_data_reduction
;
iMosflm (Battye et al., 2011)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.1779(3) 0.0068(2) 0.2264(2) 0.0322(5) Uani d 1 . .
    H H1A 0.0733 -0.0331 0.1171 0.039 Uiso calc 1 . .
    H H1B 0.2531 -0.0668 0.2374 0.039 Uiso calc 1 . .
    C C2 0.1215(3) 0.0169(2) 0.3765(2) 0.0324(5) Uani d 1 . .
    H H2A 0.0900 -0.0932 0.4081 0.039 Uiso calc 1 . .
    H H2B 0.0181 0.0592 0.3486 0.039 Uiso calc 1 . .
    C C3 0.2874(2) 0.1392(2) 0.5222(2) 0.0288(5) Uani d 1 . .
    H H3A 0.2529 0.2089 0.5934 0.035 Uiso calc 1 . .
    H H3B 0.3628 0.0797 0.5949 0.035 Uiso calc 1 . .
    N N4 0.37879(19) 0.23864(17) 0.42848(16) 0.0261(4) Uani d 1 . .
    C C5 0.5531(2) 0.3199(2) 0.4832(2) 0.0250(4) Uani d 1 . .
    O O5 0.65982(17) 0.35299(15) 0.63512(13) 0.0299(3) Uani d 1 . .
    C C5A 0.5950(2) 0.3619(2) 0.3297(2) 0.0233(4) Uani d 1 . .
    H H5A 0.5949 0.4769 0.3127 0.028 Uiso calc 1 . .
    C C6 0.7574(2) 0.32415(19) 0.3142(2) 0.0245(4) Uani d 1 . .
    H H6 0.8150 0.2754 0.4140 0.029 Uiso calc 1 . .
    C C7 0.6593(3) 0.1818(2) 0.1503(2) 0.0276(5) Uani d 1 . .
    H H7 0.7338 0.1138 0.1333 0.033 Uiso calc 1 . .
    C C8 0.5722(2) 0.2548(2) -0.0027(2) 0.0264(5) Uani d 1 . .
    H H8 0.6108 0.2775 -0.0921 0.032 Uiso calc 1 . .
    C C9 0.4292(3) 0.2805(2) 0.0152(2) 0.0284(5) Uani d 1 . .
    H H9 0.3431 0.3223 -0.0598 0.034 Uiso calc 1 . .
    C C9A 0.4358(2) 0.2276(2) 0.1826(2) 0.0256(5) Uani d 1 . .
    C C9B 0.2840(2) 0.1875(2) 0.24142(19) 0.0267(5) Uani d 1 . .
    H H9B 0.2022 0.2541 0.1950 0.032 Uiso calc 1 . .
    O O10 0.51146(16) 0.09341(13) 0.18544(14) 0.0258(3) Uani d 1 . .
    C C11 0.8967(2) 0.4657(2) 0.2990(2) 0.0259(5) Uani d 1 . .
    O O11 0.88416(17) 0.60281(15) 0.27854(15) 0.0338(4) Uani d 1 . .
    O O12 1.04071(16) 0.42233(14) 0.31124(15) 0.0312(4) Uani d 1 . .
    H H12 1.1355 0.5093 0.3163 0.047 Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 C2 . 1.532(3) ?
    C1 C9B . 1.534(3) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.552(2) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 N4 . 1.472(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    N4 C5 . 1.341(2) ?
    N4 C9B . 1.485(2) ?
    C5 O5 . 1.250(2) ?
    C5 C5A . 1.526(3) ?
    C5A C6 . 1.540(3) ?
    C5A C9A . 1.576(2) ?
    C5A H5A . 1.0000 ?
    C6 C11 . 1.500(3) ?
    C6 C7 . 1.590(2) ?
    C6 H6 . 1.0000 ?
    C7 O10 . 1.427(2) ?
    C7 C8 . 1.521(3) ?
    C7 H7 . 1.0000 ?
    C8 C9 . 1.344(3) ?
    C8 H8 . 0.9500 ?
    C9 C9A . 1.522(2) ?
    C9 H9 . 0.9500 ?
    C9A O10 . 1.446(2) ?
    C9A C9B . 1.513(3) ?
    C9B H9B . 1.0000 ?
    C11 O11 . 1.218(2) ?
    C11 O12 . 1.336(2) ?
    O12 H12 . 0.9239 ?
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
    C2 C1 C9B . . 102.15(14) ?
    C2 C1 H1A . . 111.3 ?
    C9B C1 H1A . . 111.3 ?
    C2 C1 H1B . . 111.3 ?
    C9B C1 H1B . . 111.3 ?
    H1A C1 H1B . . 109.2 ?
    C1 C2 C3 . . 104.39(16) ?
    C1 C2 H2A . . 110.9 ?
    C3 C2 H2A . . 110.9 ?
    C1 C2 H2B . . 110.9 ?
    C3 C2 H2B . . 110.9 ?
    H2A C2 H2B . . 108.9 ?
    N4 C3 C2 . . 102.16(13) ?
    N4 C3 H3A . . 111.3 ?
    C2 C3 H3A . . 111.3 ?
    N4 C3 H3B . . 111.3 ?
    C2 C3 H3B . . 111.3 ?
    H3A C3 H3B . . 109.2 ?
    C5 N4 C3 . . 127.10(15) ?
    C5 N4 C9B . . 115.10(15) ?
    C3 N4 C9B . . 113.07(13) ?
    O5 C5 N4 . . 124.50(18) ?
    O5 C5 C5A . . 127.21(17) ?
    N4 C5 C5A . . 108.28(14) ?
    C5 C5A C6 . . 117.75(15) ?
    C5 C5A C9A . . 101.00(14) ?
    C6 C5A C9A . . 101.86(13) ?
    C5 C5A H5A . . 111.7 ?
    C6 C5A H5A . . 111.7 ?
    C9A C5A H5A . . 111.7 ?
    C11 C6 C5A . . 117.00(15) ?
    C11 C6 C7 . . 113.55(15) ?
    C5A C6 C7 . . 99.72(13) ?
    C11 C6 H6 . . 108.7 ?
    C5A C6 H6 . . 108.7 ?
    C7 C6 H6 . . 108.7 ?
    O10 C7 C8 . . 102.71(15) ?
    O10 C7 C6 . . 99.48(13) ?
    C8 C7 C6 . . 109.15(14) ?
    O10 C7 H7 . . 114.6 ?
    C8 C7 H7 . . 114.6 ?
    C6 C7 H7 . . 114.6 ?
    C9 C8 C7 . . 105.52(17) ?
    C9 C8 H8 . . 127.2 ?
    C7 C8 H8 . . 127.2 ?
    C8 C9 C9A . . 104.59(17) ?
    C8 C9 H9 . . 127.7 ?
    C9A C9 H9 . . 127.7 ?
    O10 C9A C9B . . 111.77(14) ?
    O10 C9A C9 . . 102.12(14) ?
    C9B C9A C9 . . 126.44(16) ?
    O10 C9A C5A . . 100.18(14) ?
    C9B C9A C5A . . 105.83(13) ?
    C9 C9A C5A . . 107.50(14) ?
    N4 C9B C9A . . 102.11(13) ?
    N4 C9B C1 . . 101.06(14) ?
    C9A C9B C1 . . 120.38(16) ?
    N4 C9B H9B . . 110.7 ?
    C9A C9B H9B . . 110.7 ?
    C1 C9B H9B . . 110.7 ?
    C7 O10 C9A . . 96.02(13) ?
    O11 C11 O12 . . 123.30(17) ?
    O11 C11 C6 . . 125.93(18) ?
    O12 C11 C6 . . 110.77(15) ?
    C11 O12 H12 . . 113.8 ?
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
    C9B C1 C2 C3 . . . . -40.2(2) ?
    C1 C2 C3 N4 . . . . 24.99(19) ?
    C2 C3 N4 C5 . . . . -154.32(18) ?
    C2 C3 N4 C9B . . . . -0.1(2) ?
    C3 N4 C5 O5 . . . . -16.0(3) ?
    C9B N4 C5 O5 . . . . -169.80(16) ?
    C3 N4 C5 C5A . . . . 163.66(15) ?
    C9B N4 C5 C5A . . . . 9.9(2) ?
    O5 C5 C5A C6 . . . . 47.1(2) ?
    N4 C5 C5A C6 . . . . -132.62(15) ?
    O5 C5 C5A C9A . . . . 156.89(18) ?
    N4 C5 C5A C9A . . . . -22.81(19) ?
    C5 C5A C6 C11 . . . . -123.93(16) ?
    C9A C5A C6 C11 . . . . 126.75(15) ?
    C5 C5A C6 C7 . . . . 113.23(14) ?
    C9A C5A C6 C7 . . . . 3.91(16) ?
    C11 C6 C7 O10 . . . . -165.65(15) ?
    C5A C6 C7 O10 . . . . -40.40(16) ?
    C11 C6 C7 C8 . . . . -58.5(2) ?
    C5A C6 C7 C8 . . . . 66.71(18) ?
    O10 C7 C8 C9 . . . . 30.75(16) ?
    C6 C7 C8 C9 . . . . -74.15(18) ?
    C7 C8 C9 C9A . . . . 1.83(16) ?
    C8 C9 C9A O10 . . . . -33.38(16) ?
    C8 C9 C9A C9B . . . . -162.43(15) ?
    C8 C9 C9A C5A . . . . 71.53(17) ?
    C5 C5A C9A O10 . . . . -88.71(15) ?
    C6 C5A C9A O10 . . . . 32.99(16) ?
    C5 C5A C9A C9B . . . . 27.56(18) ?
    C6 C5A C9A C9B . . . . 149.26(14) ?
    C5 C5A C9A C9 . . . . 165.01(15) ?
    C6 C5A C9A C9 . . . . -73.29(18) ?
    C5 N4 C9B C9A . . . . 8.4(2) ?
    C3 N4 C9B C9A . . . . -149.09(15) ?
    C5 N4 C9B C1 . . . . 133.04(17) ?
    C3 N4 C9B C1 . . . . -24.4(2) ?
    O10 C9A C9B N4 . . . . 85.85(15) ?
    C9 C9A C9B N4 . . . . -148.99(15) ?
    C5A C9A C9B N4 . . . . -22.27(18) ?
    O10 C9A C9B C1 . . . . -24.8(2) ?
    C9 C9A C9B C1 . . . . 100.3(2) ?
    C5A C9A C9B C1 . . . . -132.96(15) ?
    C2 C1 C9B N4 . . . . 38.51(18) ?
    C2 C1 C9B C9A . . . . 149.76(16) ?
    C8 C7 O10 C9A . . . . -49.46(13) ?
    C6 C7 O10 C9A . . . . 62.79(14) ?
    C9B C9A O10 C7 . . . . -171.68(12) ?
    C9 C9A O10 C7 . . . . 50.59(14) ?
    C5A C9A O10 C7 . . . . -59.96(14) ?
    C5A C6 C11 O11 . . . . -8.9(2) ?
    C7 C6 C11 O11 . . . . 106.5(2) ?
    C5A C6 C11 O12 . . . . 171.02(12) ?
    C7 C6 C11 O12 . . . . -73.58(19) ?
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
    O12 H12 O5 2_766 0.92 1.70 2.607(2) 165
    C9 H9 O11 2_665 0.95 2.42 3.362(3) 172
_shelxl_version_number     2014/6
