# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Aver2102
_audit_block_doi                 10.5517/ccdc.csd.cc2788qj
_database_code_depnum_ccdc_archive 'CCDC 2063537'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Chemistry Department of Moscow State University
Russia
;
_audit_update_record             
;
2021-02-17 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_chemical_name_systematic        
;
 4-(3-fluoro-4-nitroisoxazol-5-yl)morpholine
;
_chemical_name_common            ?
_chemical_melting_point_gt       384
_chemical_melting_point_lt       385
_chemical_formula_moiety         'C7 H8 F N3 O4'
_chemical_formula_sum            'C7 H8 F N3 O4'
_chemical_formula_weight         217.16
_chemical_absolute_configuration unk

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_preparation       'petroleum ether \ dichloromethane'

_cell_length_a                   5.3356(14)
_cell_length_b                   8.561(3)
_cell_length_c                   19.632(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     896.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1307

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1472(5) 0.7316(4) 0.09776(15) 0.0478(7) Uani 1 1 d . . . . .
O1 O -0.0253(4) 0.7371(3) 0.04708(11) 0.0610(6) Uani 1 1 d . . . . .
N1 N -0.0466(6) 0.5896(5) 0.01541(17) 0.0739(9) Uani 1 1 d . . . . .
C2 C 0.2436(5) 0.5814(4) 0.10015(15) 0.0504(7) Uani 1 1 d . . . . .
C3 C 0.1102(7) 0.5018(5) 0.04815(18) 0.0633(9) Uani 1 1 d . . . . .
F3 F 0.1371(6) 0.3553(3) 0.03088(14) 0.0915(8) Uani 1 1 d . . . . .
N2 N 0.4601(5) 0.5258(4) 0.13346(15) 0.0585(7) Uani 1 1 d . . . . .
O21 O 0.5975(4) 0.6202(4) 0.16232(13) 0.0664(7) Uani 1 1 d . . . . .
O22 O 0.5016(6) 0.3848(4) 0.13115(18) 0.0940(11) Uani 1 1 d . . . . .
N11 N 0.1866(4) 0.8635(4) 0.13245(13) 0.0512(6) Uani 1 1 d . . . . .
C12 C 0.2314(5) 0.8614(5) 0.20649(15) 0.0529(7) Uani 1 1 d . . . . .
H12A H 0.3524 0.9412 0.2188 0.064 Uiso 1 1 calc R U . . .
H12B H 0.2970 0.7606 0.2203 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0181(6) 0.8927(5) 0.24172(16) 0.0603(9) Uani 1 1 d . . . . .
H13A H -0.1316 0.8068 0.2325 0.072 Uiso 1 1 calc R U . . .
H13B H 0.0086 0.8975 0.2905 0.072 Uiso 1 1 calc R U . . .
O14 O -0.1299(5) 1.0338(4) 0.21972(15) 0.0733(8) Uani 1 1 d . . . . .
C15 C -0.1746(6) 1.0338(5) 0.1481(2) 0.0684(9) Uani 1 1 d . . . . .
H15A H -0.2485 1.1326 0.1347 0.082 Uiso 1 1 calc R U . . .
H15B H -0.2918 0.9512 0.1367 0.082 Uiso 1 1 calc R U . . .
C16 C 0.0693(6) 1.0089(5) 0.10981(18) 0.0592(8) Uani 1 1 d . . . . .
H16A H 0.0363 1.0039 0.0613 0.071 Uiso 1 1 calc R U . . .
H16B H 0.1816 1.0959 0.1182 0.071 Uiso 1 1 calc R U . . .


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
C1 N11 1.335(5) . ?
C1 O1 1.356(3) . ?
C1 C2 1.386(5) . ?
O1 N1 1.413(5) . ?
N1 C3 1.295(6) . ?
C2 N2 1.410(4) . ?
C2 C3 1.419(5) . ?
C3 F3 1.307(5) . ?
N2 O22 1.228(5) . ?
N2 O21 1.230(4) . ?
N11 C16 1.463(5) . ?
N11 C12 1.473(4) . ?
C12 C13 1.524(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O14 1.415(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O14 C15 1.425(5) . ?
C15 C16 1.518(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
N11 C1 O1 116.8(3) . . ?
N11 C1 C2 135.2(3) . . ?
O1 C1 C2 108.0(3) . . ?
C1 O1 N1 110.3(3) . . ?
C3 N1 O1 104.4(3) . . ?
C1 C2 N2 129.3(3) . . ?
C1 C2 C3 103.6(3) . . ?
N2 C2 C3 125.6(3) . . ?
N1 C3 F3 119.9(4) . . ?
N1 C3 C2 113.7(4) . . ?
F3 C3 C2 126.3(4) . . ?
O22 N2 O21 123.8(3) . . ?
O22 N2 C2 117.5(3) . . ?
O21 N2 C2 118.7(3) . . ?
C1 N11 C16 119.8(3) . . ?
C1 N11 C12 121.3(3) . . ?
C16 N11 C12 112.3(3) . . ?
N11 C12 C13 107.7(3) . . ?
N11 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
N11 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
O14 C13 C12 112.3(3) . . ?
O14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
O14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C13 O14 C15 111.8(3) . . ?
O14 C15 C16 110.2(3) . . ?
O14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
O14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N11 C16 C15 109.6(3) . . ?
N11 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N11 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C1 O1 N1 -179.8(3) . . . . ?
C2 C1 O1 N1 0.4(3) . . . . ?
C1 O1 N1 C3 0.5(4) . . . . ?
N11 C1 C2 N2 -14.4(6) . . . . ?
O1 C1 C2 N2 165.3(3) . . . . ?
N11 C1 C2 C3 179.2(3) . . . . ?
O1 C1 C2 C3 -1.0(3) . . . . ?
O1 N1 C3 F3 -179.7(3) . . . . ?
O1 N1 C3 C2 -1.2(4) . . . . ?
C1 C2 C3 N1 1.4(4) . . . . ?
N2 C2 C3 N1 -165.6(3) . . . . ?
C1 C2 C3 F3 179.8(4) . . . . ?
N2 C2 C3 F3 12.9(6) . . . . ?
C1 C2 N2 O22 176.4(3) . . . . ?
C3 C2 N2 O22 -20.0(5) . . . . ?
C1 C2 N2 O21 -4.4(5) . . . . ?
C3 C2 N2 O21 159.2(3) . . . . ?
O1 C1 N11 C16 -7.4(4) . . . . ?
C2 C1 N11 C16 172.4(3) . . . . ?
O1 C1 N11 C12 141.9(3) . . . . ?
C2 C1 N11 C12 -38.4(5) . . . . ?
C1 N11 C12 C13 -96.0(4) . . . . ?
C16 N11 C12 C13 55.4(4) . . . . ?
N11 C12 C13 O14 -55.8(4) . . . . ?
C12 C13 O14 C15 59.0(4) . . . . ?
C13 O14 C15 C16 -58.3(4) . . . . ?
C1 N11 C16 C15 94.9(4) . . . . ?
C12 N11 C16 C15 -57.0(4) . . . . ?
O14 C15 C16 N11 56.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B O21 0.97 2.30 2.972(4) 125.2 .
C12 H12B O14 0.97 2.44 3.203(5) 135.3 4_545
C13 H13A O21 0.97 2.56 3.475(5) 157.9 1_455
C15 H15A O22 0.97 2.54 3.482(5) 164.3 1_465

_refine_ls_abs_structure_details 
;
 Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)

########################################################################### 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;

_cell_measurement_reflns_used    8235
_cell_measurement_theta_min      4.505
_cell_measurement_theta_max      70.386

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.279
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.784
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.128
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.7659
_exptl_absorpt_correction_T_max  0.8799

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
'63 runs, 1654 frames, detector distance = 42 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8235
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.0671 # before absorption correction
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.505
_diffrn_reflns_theta_max         70.386
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1670
_reflns_number_gt                1434
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    0.963

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X--AREA        (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA        (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA        (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97       (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL--2014/7 (Sheldrick,  2014)'
_computing_molecular_graphics    'Ortep--3       (Farrugia,   1997)'
_computing_publication_material  'WinGX          (Farrugia,   1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1670
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_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.
;

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Aver1830
_audit_block_doi                 10.5517/ccdc.csd.cc21phz7
_database_code_depnum_ccdc_archive 'CCDC 1897509'
loop_
_audit_author_name
_audit_author_address
'Victor Rybakov'
;Chem. Dept. of Moscow State Univ.
Russia
;
_audit_update_record             
;
2019-02-15 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_chemical_name_systematic        4-(3-nitroisoxazol-5-yl)morpholine
_chemical_name_common            ?
_chemical_melting_point_gt       387
_chemical_melting_point_lt       389
_chemical_formula_moiety         'C7 H9 N3 O4'
_chemical_formula_sum            'C7 H9 N3 O4'
_chemical_formula_weight         199.17

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_preparation       CH₂Cl₂--i--PrOH

_cell_length_a                   6.5806(19)
_cell_length_b                   12.0214(16)
_cell_length_c                   10.9200(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.833(17)
_cell_angle_gamma                90
_cell_volume                     861.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+1/2, y+1/2, -z+1/2'
'-x+, -y+, -z+'
'x-1/2, -y-1/2, z-1/2'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0916

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.04676(19) 0.49977(10) 1.22051(11) 0.0604(3) Uani 1 1 d . . . . .
O1 O 0.13946(15) 0.40623(8) 1.16949(9) 0.0589(3) Uani 1 1 d . . . . .
C1 C 0.00696(18) 0.35762(10) 1.08619(10) 0.0427(3) Uani 1 1 d . . . . .
C2 C -0.17309(19) 0.41353(10) 1.08059(11) 0.0453(3) Uani 1 1 d . . . . .
H2 H -0.2920 0.3987 1.0325 0.054 Uiso 1 1 calc R U . . .
C3 C -0.13366(19) 0.49847(10) 1.16519(11) 0.0457(3) Uani 1 1 d . . . . .
N11 N 0.07868(15) 0.26996(9) 1.02468(9) 0.0454(3) Uani 1 1 d . . . . .
C12 C -0.07348(19) 0.19769(11) 0.96044(12) 0.0498(3) Uani 1 1 d . . . . .
H12A H -0.1740 0.2429 0.9144 0.060 Uiso 1 1 calc R U . . .
H12B H -0.1430 0.1543 1.0198 0.060 Uiso 1 1 calc R U . . .
C13 C 0.0278(2) 0.12098(12) 0.87447(12) 0.0537(3) Uani 1 1 d . . . . .
H13A H -0.0718 0.0683 0.8399 0.064 Uiso 1 1 calc R U . . .
H13B H 0.0771 0.1641 0.8075 0.064 Uiso 1 1 calc R U . . .
O14 O 0.19283(15) 0.06186(8) 0.93378(10) 0.0584(3) Uani 1 1 d . . . . .
C15 C 0.3426(2) 0.13699(12) 0.98293(15) 0.0589(4) Uani 1 1 d . . . . .
H15A H 0.3911 0.1821 0.9173 0.071 Uiso 1 1 calc R U . . .
H15B H 0.4574 0.0954 1.0197 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2588(2) 0.21148(12) 1.07806(13) 0.0564(3) Uani 1 1 d . . . . .
H16A H 0.2223 0.1674 1.1477 0.068 Uiso 1 1 calc R U . . .
H16B H 0.3615 0.2650 1.1067 0.068 Uiso 1 1 calc R U . . .
N3 N -0.27469(19) 0.58561(9) 1.19633(11) 0.0538(3) Uani 1 1 d . . . . .
O31 O -0.21655(18) 0.65599(8) 1.27037(10) 0.0677(3) Uani 1 1 d . . . . .
O32 O -0.44371(18) 0.58200(10) 1.14523(12) 0.0787(4) Uani 1 1 d . . . . .


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
N1 C3 1.2957(17) . ?
N1 O1 1.4115(14) . ?
O1 C1 1.3502(14) . ?
C1 N11 1.3516(15) . ?
C1 C2 1.3601(17) . ?
C2 C3 1.3897(17) . ?
C2 H2 0.9300 . ?
C3 N3 1.4548(16) . ?
N11 C16 1.4651(16) . ?
N11 C12 1.4682(15) . ?
C12 C13 1.5031(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O14 1.4178(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O14 C15 1.4157(17) . ?
C15 C16 1.504(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N3 O32 1.2113(16) . ?
N3 O31 1.2144(15) . ?

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
C3 N1 O1 102.30(10) . . ?
C1 O1 N1 109.51(10) . . ?
O1 C1 N11 116.17(10) . . ?
O1 C1 C2 109.74(11) . . ?
N11 C1 C2 134.03(11) . . ?
C1 C2 C3 102.11(11) . . ?
C1 C2 H2 128.9 . . ?
C3 C2 H2 128.9 . . ?
N1 C3 C2 116.32(12) . . ?
N1 C3 N3 117.47(12) . . ?
C2 C3 N3 126.21(12) . . ?
C1 N11 C16 118.45(10) . . ?
C1 N11 C12 116.69(10) . . ?
C16 N11 C12 114.45(10) . . ?
N11 C12 C13 110.17(10) . . ?
N11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O14 C13 C12 112.35(11) . . ?
O14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
O14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 O14 C13 110.24(10) . . ?
O14 C15 C16 111.33(12) . . ?
O14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
O14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N11 C16 C15 109.58(11) . . ?
N11 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N11 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
O32 N3 O31 124.77(13) . . ?
O32 N3 C3 116.55(12) . . ?
O31 N3 C3 118.67(12) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 O1 C1 0.92(14) . . . . ?
N1 O1 C1 N11 176.57(10) . . . . ?
N1 O1 C1 C2 -1.12(14) . . . . ?
O1 C1 C2 C3 0.80(13) . . . . ?
N11 C1 C2 C3 -176.31(13) . . . . ?
O1 N1 C3 C2 -0.43(15) . . . . ?
O1 N1 C3 N3 179.98(10) . . . . ?
C1 C2 C3 N1 -0.21(15) . . . . ?
C1 C2 C3 N3 179.34(11) . . . . ?
O1 C1 N11 C16 20.46(17) . . . . ?
C2 C1 N11 C16 -162.57(14) . . . . ?
O1 C1 N11 C12 163.53(11) . . . . ?
C2 C1 N11 C12 -19.5(2) . . . . ?
C1 N11 C12 C13 167.24(11) . . . . ?
C16 N11 C12 C13 -48.23(15) . . . . ?
N11 C12 C13 O14 52.38(15) . . . . ?
C12 C13 O14 C15 -60.05(15) . . . . ?
C13 O14 C15 C16 61.74(15) . . . . ?
C1 N11 C16 C15 -166.13(12) . . . . ?
C12 N11 C16 C15 50.00(16) . . . . ?
O14 C15 C16 N11 -56.01(16) . . . . ?
N1 C3 N3 O32 -178.81(13) . . . . ?
C2 C3 N3 O32 1.64(19) . . . . ?
N1 C3 N3 O31 1.24(17) . . . . ?
C2 C3 N3 O31 -178.31(12) . . . . ?

#############################################################################

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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.
;

_cell_measurement_reflns_used    25
_cell_measurement_theta_min      31.40
_cell_measurement_theta_max      34.88

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.100
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.110
_exptl_absorpt_process_details   
;
 Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.7840
_exptl_absorpt_correction_T_max  0.8958

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x--ray
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non--profiled ω--scans'
_diffrn_standards_number         1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 3 -1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_standards_decay_corr_max 1.005
_diffrn_standards_decay_corr_min 1.000
_diffrn_reflns_number            1770
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0230 # before absorption correction
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.480
_diffrn_reflns_theta_max         74.909
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1770
_reflns_number_gt                1545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CAD4 Express   (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express   (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4          (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS97       (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2015/1  (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.1264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1770
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000



_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.
;

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032

