# 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_9c
_database_code_depnum_ccdc_archive 'CCDC 2110941'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-07-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 Br N O4'
_chemical_formula_sum            'C15 H14 Br N O4'
_chemical_formula_weight         352.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H13 Br N O4'
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'
Br Br -0.6763 1.2805 '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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   6.70863(6)
_cell_length_b                   31.0104(3)
_cell_length_c                   6.93722(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.1997(10)
_cell_angle_gamma                90
_cell_volume                     1354.43(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13015
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7000
_cell_measurement_theta_min      2.8420
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.725
_exptl_absorpt_coefficient_mu    4.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.301
_diffrn_reflns_theta_min         2.850
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    103.00 175.90   0.30    0.50    --  111.50  45.00  90.00  243
  2  ω    101.00 170.90   0.30    0.50    --  111.50  45.00 -30.00  233
  3  ω    146.00 176.00   0.30    0.50    --  111.50  45.00 -60.00  100
  4  ω    112.00 142.00   0.30    0.50    --  111.50  45.00 -60.00  100
  5  ω    107.00 140.00   0.30    0.50    --  111.50  45.00 -90.00  110
  6  ω    -26.00  25.00   0.30    0.50    --  -48.76  19.00  90.00  170
  7  ω    -26.00  25.00   0.30    0.50    --  -48.76  19.00 -30.00  170
  8  ω    -51.00 -18.00   0.30    0.50    --  -90.00  45.00 -60.00  110
  9  ω    -51.00 -18.00   0.30    0.50    --  -90.00  45.00 -90.00  110
 10  ω    -26.00  25.00   0.30    0.50    --  -48.76  19.00-180.00  170
 11  ω     45.00 106.20   0.30    0.50    --   48.76-144.00-107.00  204
 12  ω     45.00 124.20   0.30    0.50    --  111.50-144.00-107.00  264
 13  ω     43.00  92.20   0.30    0.50    --  111.50-138.00 -50.92  164
 14  ω     40.00 112.00   0.30    0.50    --  111.50-127.00  60.00  240
 15  ω     41.00  66.20   0.30    0.50    --  111.50-110.00  92.30   84
 16  ω     82.00 107.20   0.30    0.50    --  111.50-110.00  92.30   84
 17  ω     78.00 105.00   0.30    0.50    --  111.50-125.00  90.00   90
 18  ω     79.00 104.80   0.30    0.50    --  111.50-104.00 125.59   86
 19  ω     61.00 107.20   0.30    0.50    --  111.50-110.00 106.58  154
 20  ω     41.00 103.10   0.30    0.50    --  111.50 -95.00 120.00  207
 21  ω     55.00 106.00   0.30    0.50    --  111.50-106.00 167.12  170
 22  ω     36.00  96.00   0.30    0.50    --   48.76-127.00  60.00  200
 23  ω     76.00 104.20   0.30    0.50    --  111.50 -95.00  60.00   94
 24  ω     40.00  68.80   0.30    0.50    --  111.50 -95.00  60.00   96
 25  ω     40.00  65.20   0.30    0.50    --  111.50 -77.00  30.00   84
 26  ω     41.00  66.20   0.30    0.50    --  111.50 -61.00 120.00   84
 27  ω     42.00  69.00   0.30    0.50    --  111.50 -61.00 150.00   90
 28  ω     46.00  71.80   0.30    0.50    --  111.50 -77.00-180.00   86
 29  ω     41.00  69.20   0.30    0.50    --  111.50 -61.00-150.00   94
 30  ω     96.00 151.20   0.30    0.50    --  111.50 125.00 -30.00  184
 31  ω     82.00 169.00   0.30    0.50    --  111.50 144.00 -54.00  290
 32  ω     94.00 178.00   0.30    0.50    --  111.50 127.00 136.00  280
 33  ω    -88.00 -19.00   0.30    0.50    --  -90.00 127.00 136.00  230
 34  ω   -121.00 -73.00   0.30    0.50    --  -48.76-127.00  60.00  160
 35  ω   -141.00-115.80   0.30    0.50    --  -90.00-127.00  60.00   84
 36  ω   -121.00 -73.00   0.30    0.50    --  -48.76-125.00 -90.00  160
 37  ω   -121.00 -61.00   0.30    0.50    --  -48.76-144.00-107.00  200
 38  ω   -153.00 -60.00   0.30    0.50    --  -90.00-144.00-107.00  310
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1123936000
_diffrn_orient_matrix_UB_12      -0.0073935000
_diffrn_orient_matrix_UB_13      0.2319603000
_diffrn_orient_matrix_UB_21      0.0026654000
_diffrn_orient_matrix_UB_22      0.0490082000
_diffrn_orient_matrix_UB_23      0.0368014000
_diffrn_orient_matrix_UB_31      -0.2174472000
_diffrn_orient_matrix_UB_32      -0.0032375000
_diffrn_orient_matrix_UB_33      0.0284012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2758
_reflns_number_total             2906
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+0.8365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0681
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br1 Br -0.00515(3) 0.22932(2) 0.21597(3) 0.01767(8) Uani 1 1 d . . . . .
N1 N 0.8364(2) 0.46085(5) 0.5834(2) 0.0125(3) Uani 1 1 d . . . . .
H1 H 0.900(4) 0.4847(9) 0.614(4) 0.028(6) Uiso 1 1 d . . . . .
C1 C 0.8283(2) 0.44316(5) 0.4051(2) 0.0124(3) Uani 1 1 d . . . . .
O1 O 0.91346(19) 0.46097(4) 0.29221(18) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.7148(3) 0.40070(5) 0.3468(3) 0.0136(3) Uani 1 1 d . . . . .
H2A H 0.824(4) 0.3779(7) 0.407(4) 0.019(5) Uiso 1 1 d . . . . .
H2B H 0.662(3) 0.3997(7) 0.196(3) 0.012(5) Uiso 1 1 d . . . . .
C3 C 0.5344(2) 0.39581(5) 0.4327(2) 0.0111(3) Uani 1 1 d . . . . .
H3 H 0.439(3) 0.4201(7) 0.384(3) 0.008(5) Uiso 1 1 d . . . . .
C4 C 0.6324(2) 0.39925(5) 0.6696(2) 0.0112(3) Uani 1 1 d . . . . .
O2 O 0.7670(2) 0.36332(4) 0.74602(19) 0.0159(2) Uani 1 1 d . . . . .
H2 H 0.863(4) 0.3733(9) 0.842(5) 0.034(7) Uiso 1 1 d . . . . .
C5 C 0.7549(2) 0.44255(5) 0.7324(2) 0.0110(3) Uani 1 1 d . . . . .
O3 O 0.93032(18) 0.43592(4) 0.91713(18) 0.0143(2) Uani 1 1 d . . . . .
H3A H 0.908(4) 0.4449(9) 1.016(4) 0.031(7) Uiso 1 1 d . . . . .
C6 C 0.5907(3) 0.47257(6) 0.7749(2) 0.0138(3) Uani 1 1 d . . . . .
O4 O 0.6054(2) 0.51164(4) 0.78027(19) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.4321(3) 0.44475(6) 0.8116(3) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.332(4) 0.4547(8) 0.862(4) 0.027(6) Uiso 1 1 d . . . . .
C8 C 0.4607(3) 0.40363(6) 0.7675(2) 0.0146(3) Uani 1 1 d . . . . .
C9 C 0.3474(3) 0.36526(7) 0.8065(3) 0.0218(4) Uani 1 1 d . . . . .
H9A H 0.265(5) 0.3511(11) 0.690(5) 0.054(9) Uiso 1 1 d . . . . .
H9B H 0.254(5) 0.3725(9) 0.876(5) 0.044(8) Uiso 1 1 d . . . . .
H9C H 0.446(5) 0.3461(10) 0.890(5) 0.052(9) Uiso 1 1 d . . . . .
C10 C 0.4063(3) 0.35493(5) 0.3608(2) 0.0117(3) Uani 1 1 d . . . . .
C11 C 0.5018(3) 0.31447(6) 0.3783(3) 0.0158(3) Uani 1 1 d . . . . .
H11 H 0.653(4) 0.3119(8) 0.426(4) 0.021(6) Uiso 1 1 d . . . . .
C12 C 0.3817(3) 0.27691(6) 0.3311(3) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.447(3) 0.2492(8) 0.348(3) 0.018(5) Uiso 1 1 d . . . . .
C13 C 0.1619(3) 0.28019(6) 0.2627(3) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.0616(3) 0.32001(6) 0.2316(3) 0.0136(3) Uani 1 1 d . . . . .
H14 H -0.079(3) 0.3222(7) 0.186(3) 0.009(5) Uiso 1 1 d . . . . .
C15 C 0.1849(3) 0.35714(5) 0.2815(2) 0.0132(3) Uani 1 1 d . . . . .
H15 H 0.122(3) 0.3848(8) 0.265(3) 0.019(5) Uiso 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.8971(17) . ?
N1 H1 0.84(3) . ?
N1 C1 1.337(2) . ?
N1 C5 1.442(2) . ?
C1 O1 1.246(2) . ?
C1 C2 1.505(2) . ?
C2 H2A 1.00(2) . ?
C2 H2B 0.98(2) . ?
C2 C3 1.530(2) . ?
C3 H3 0.97(2) . ?
C3 C4 1.549(2) . ?
C3 C10 1.516(2) . ?
C4 O2 1.4168(19) . ?
C4 C5 1.556(2) . ?
C4 C8 1.531(2) . ?
O2 H2 0.81(3) . ?
C5 O3 1.4240(19) . ?
C5 C6 1.546(2) . ?
O3 H3A 0.80(3) . ?
C6 O4 1.215(2) . ?
C6 C7 1.459(2) . ?
C7 H7 0.92(3) . ?
C7 C8 1.341(3) . ?
C8 C9 1.486(2) . ?
C9 H9A 0.92(4) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.93(3) . ?
C10 C11 1.395(2) . ?
C10 C15 1.396(2) . ?
C11 H11 0.96(2) . ?
C11 C12 1.389(2) . ?
C12 H12 0.96(2) . ?
C12 C13 1.388(2) . ?
C13 C14 1.387(2) . ?
C14 H14 0.89(2) . ?
C14 C15 1.390(2) . ?
C15 H15 0.94(2) . ?

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
C1 N1 H1 116.7(18) . . ?
C1 N1 C5 126.67(14) . . ?
C5 N1 H1 116.6(18) . . ?
N1 C1 C2 117.58(14) . . ?
O1 C1 N1 121.21(15) . . ?
O1 C1 C2 121.20(15) . . ?
C1 C2 H2A 106.1(13) . . ?
C1 C2 H2B 106.2(12) . . ?
C1 C2 C3 112.13(14) . . ?
H2A C2 H2B 111.6(18) . . ?
C3 C2 H2A 109.2(13) . . ?
C3 C2 H2B 111.5(12) . . ?
C2 C3 H3 107.6(12) . . ?
C2 C3 C4 107.70(13) . . ?
C4 C3 H3 107.5(12) . . ?
C10 C3 C2 112.93(13) . . ?
C10 C3 H3 107.8(12) . . ?
C10 C3 C4 113.02(13) . . ?
C3 C4 C5 110.25(13) . . ?
O2 C4 C3 108.95(13) . . ?
O2 C4 C5 111.53(13) . . ?
O2 C4 C8 112.54(13) . . ?
C8 C4 C3 111.62(13) . . ?
C8 C4 C5 101.81(13) . . ?
C4 O2 H2 103.4(19) . . ?
N1 C5 C4 115.67(13) . . ?
N1 C5 C6 111.79(13) . . ?
O3 C5 N1 107.53(13) . . ?
O3 C5 C4 108.68(13) . . ?
O3 C5 C6 109.72(13) . . ?
C6 C5 C4 103.34(12) . . ?
C5 O3 H3A 112.3(19) . . ?
O4 C6 C5 123.39(15) . . ?
O4 C6 C7 129.85(16) . . ?
C7 C6 C5 106.72(14) . . ?
C6 C7 H7 123.2(16) . . ?
C8 C7 C6 110.61(15) . . ?
C8 C7 H7 126.2(16) . . ?
C7 C8 C4 111.98(15) . . ?
C7 C8 C9 126.69(16) . . ?
C9 C8 C4 121.33(16) . . ?
C8 C9 H9A 114(2) . . ?
C8 C9 H9B 112.0(18) . . ?
C8 C9 H9C 109.1(19) . . ?
H9A C9 H9B 105(3) . . ?
H9A C9 H9C 109(3) . . ?
H9B C9 H9C 107(3) . . ?
C11 C10 C3 122.17(14) . . ?
C11 C10 C15 118.19(15) . . ?
C15 C10 C3 119.59(15) . . ?
C10 C11 H11 120.4(14) . . ?
C12 C11 C10 121.48(16) . . ?
C12 C11 H11 118.1(14) . . ?
C11 C12 H12 121.4(14) . . ?
C13 C12 C11 118.69(16) . . ?
C13 C12 H12 119.9(13) . . ?
C12 C13 Br1 119.52(14) . . ?
C14 C13 Br1 119.17(13) . . ?
C14 C13 C12 121.30(16) . . ?
C13 C14 H14 121.5(14) . . ?
C13 C14 C15 118.93(15) . . ?
C15 C14 H14 119.5(14) . . ?
C10 C15 H15 117.5(14) . . ?
C14 C15 C10 121.21(16) . . ?
C14 C15 H15 121.3(14) . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.84(3) 2.06(3) 2.9047(19) 174(2) 3_766 yes
O2 H2 O3 0.81(3) 2.02(3) 2.6039(18) 128(3) . yes
O3 H3A O1 0.80(3) 1.97(3) 2.7550(17) 167(3) 1_556 yes

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
Br1 C13 C14 C15 174.96(12) . . . . ?
N1 C1 C2 C3 30.3(2) . . . . ?
N1 C5 C6 O4 -36.7(2) . . . . ?
N1 C5 C6 C7 145.29(14) . . . . ?
C1 N1 C5 C4 -4.3(2) . . . . ?
C1 N1 C5 O3 117.28(17) . . . . ?
C1 N1 C5 C6 -122.24(17) . . . . ?
C1 C2 C3 C4 -59.35(17) . . . . ?
C1 C2 C3 C10 175.15(13) . . . . ?
O1 C1 C2 C3 -150.45(15) . . . . ?
C2 C3 C4 O2 -66.26(16) . . . . ?
C2 C3 C4 C5 56.45(16) . . . . ?
C2 C3 C4 C8 168.84(13) . . . . ?
C2 C3 C10 C11 51.4(2) . . . . ?
C2 C3 C10 C15 -131.05(16) . . . . ?
C3 C4 C5 N1 -26.53(18) . . . . ?
C3 C4 C5 O3 -147.55(13) . . . . ?
C3 C4 C5 C6 95.96(14) . . . . ?
C3 C4 C8 C7 -98.54(17) . . . . ?
C3 C4 C8 C9 82.06(19) . . . . ?
C3 C10 C11 C12 173.41(16) . . . . ?
C3 C10 C15 C14 -174.07(15) . . . . ?
C4 C3 C10 C11 -71.1(2) . . . . ?
C4 C3 C10 C15 106.38(17) . . . . ?
C4 C5 C6 O4 -161.76(15) . . . . ?
C4 C5 C6 C7 20.24(16) . . . . ?
O2 C4 C5 N1 94.65(16) . . . . ?
O2 C4 C5 O3 -26.36(17) . . . . ?
O2 C4 C5 C6 -142.86(13) . . . . ?
O2 C4 C8 C7 138.58(15) . . . . ?
O2 C4 C8 C9 -40.8(2) . . . . ?
C5 N1 C1 O1 -176.44(15) . . . . ?
C5 N1 C1 C2 2.8(2) . . . . ?
C5 C4 C8 C7 19.06(18) . . . . ?
C5 C4 C8 C9 -160.33(15) . . . . ?
C5 C6 C7 C8 -9.11(19) . . . . ?
O3 C5 C6 O4 82.48(19) . . . . ?
O3 C5 C6 C7 -95.52(15) . . . . ?
C6 C7 C8 C4 -6.6(2) . . . . ?
C6 C7 C8 C9 172.75(16) . . . . ?
O4 C6 C7 C8 173.06(17) . . . . ?
C8 C4 C5 N1 -145.11(14) . . . . ?
C8 C4 C5 O3 93.87(14) . . . . ?
C8 C4 C5 C6 -22.62(15) . . . . ?
C10 C3 C4 O2 59.19(17) . . . . ?
C10 C3 C4 C5 -178.10(13) . . . . ?
C10 C3 C4 C8 -65.71(18) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C10 C15 C14 3.5(2) . . . . ?
C11 C12 C13 Br1 -175.53(13) . . . . ?
C11 C12 C13 C14 3.1(3) . . . . ?
C12 C13 C14 C15 -3.7(3) . . . . ?
C13 C14 C15 C10 0.3(2) . . . . ?
C15 C10 C11 C12 -4.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.853
####################################################################### 
# 
# 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_9n
_database_code_depnum_ccdc_archive 'CCDC 2110942'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N3 O5, H2 O'
_chemical_formula_sum            'C19 H27 N3 O6'
_chemical_formula_weight         393.43

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'

_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'

_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.
;

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'

_cell_length_a                   9.2023(3)
_cell_length_b                   10.5800(3)
_cell_length_c                   20.2538(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.5857(8)
_cell_angle_gamma                90
_cell_volume                     1931.74(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9358
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      34.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_T_max  0.8625
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            79433
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         34.497
_diffrn_reflns_theta_full        25.242
_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             8190
_reflns_number_gt                6789
_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       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.6832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8190
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.70626(10) 0.30097(9) 0.71057(5) 0.0345(2) Uani 1 1 d . . . . .
O2 O 0.15229(8) 0.50848(7) 0.58970(4) 0.02077(14) Uani 1 1 d . . . . .
H2 H 0.1483(18) 0.4931(16) 0.5460(9) 0.034(4) Uiso 1 1 d . . . . .
O3 O 0.31920(9) 0.53801(8) 0.73144(4) 0.02603(16) Uani 1 1 d . . . . .
O4 O 0.06082(8) 0.72642(7) 0.52856(3) 0.01831(13) Uani 1 1 d . . . . .
H4 H -0.010(2) 0.6697(19) 0.5351(10) 0.047(5) Uiso 1 1 d . . . . .
O5 O 0.55889(8) 0.65275(8) 0.53748(4) 0.02427(15) Uani 1 1 d . . . . .
N1 N 0.82669(13) 0.22067(10) 0.70318(6) 0.0343(2) Uani 1 1 d . . . . .
N2 N 0.83552(10) 0.40322(8) 0.64792(5) 0.02308(17) Uani 1 1 d . . . . .
N3 N 0.38819(9) 0.59890(7) 0.59870(4) 0.01680(14) Uani 1 1 d . . . . .
C1 C 0.89815(11) 0.28651(9) 0.66614(5) 0.02120(17) Uani 1 1 d . . . . .
C2 C 1.03449(14) 0.24110(11) 0.64537(6) 0.0287(2) Uani 1 1 d . . . . .
H2A H 1.111(2) 0.302(2) 0.6574(10) 0.052(5) Uiso 1 1 d . . . . .
H2B H 1.017(2) 0.2309(17) 0.5959(10) 0.045(5) Uiso 1 1 d . . . . .
H2C H 1.0714(19) 0.1626(17) 0.6684(9) 0.036(4) Uiso 1 1 d . . . . .
C3 C 0.72171(11) 0.40646(9) 0.67646(5) 0.02015(17) Uani 1 1 d . . . . .
C4 C 0.61052(12) 0.50883(10) 0.67328(5) 0.02217(18) Uani 1 1 d . . . . .
H4A H 0.6581(16) 0.5874(14) 0.6625(7) 0.023(3) Uiso 1 1 d . . . . .
H4B H 0.5822(17) 0.5201(15) 0.7174(8) 0.030(4) Uiso 1 1 d . . . . .
C5 C 0.47178(11) 0.48180(9) 0.61887(5) 0.01956(16) Uani 1 1 d . . . . .
H5A H 0.5015(17) 0.4475(15) 0.5780(8) 0.026(4) Uiso 1 1 d . . . . .
H5B H 0.4052(16) 0.4246(14) 0.6333(7) 0.023(3) Uiso 1 1 d . . . . .
C6 C 0.24124(10) 0.61266(9) 0.61477(4) 0.01643(15) Uani 1 1 d . . . . .
C7 C 0.24124(11) 0.60718(10) 0.69117(5) 0.01992(17) Uani 1 1 d . . . . .
C8 C 0.12528(12) 0.69305(10) 0.70268(5) 0.02275(18) Uani 1 1 d . . . . .
H8 H 0.0863(18) 0.6961(16) 0.7448(9) 0.035(4) Uiso 1 1 d . . . . .
C9 C 0.07438(10) 0.76402(9) 0.64794(5) 0.01894(16) Uani 1 1 d . . . . .
C10 C 0.15898(10) 0.74067(9) 0.59137(4) 0.01570(15) Uani 1 1 d . . . . .
C11 C -0.05327(12) 0.85384(11) 0.64091(6) 0.0251(2) Uani 1 1 d . . . . .
H11A H -0.103(2) 0.8637(17) 0.5957(10) 0.041(5) Uiso 1 1 d . . . . .
H11B H -0.022(2) 0.9365(18) 0.6594(9) 0.046(5) Uiso 1 1 d . . . . .
H11C H -0.1261(19) 0.8188(18) 0.6649(9) 0.042(5) Uiso 1 1 d . . . . .
C12 C 0.26948(10) 0.84769(8) 0.58221(4) 0.01521(14) Uani 1 1 d . . . . .
C13 C 0.35508(10) 0.79307(9) 0.53124(4) 0.01696(15) Uani 1 1 d . . . . .
H13A H 0.2866(16) 0.7710(14) 0.4907(8) 0.024(3) Uiso 1 1 d . . . . .
H13B H 0.4238(17) 0.8534(14) 0.5184(8) 0.026(4) Uiso 1 1 d . . . . .
C14 C 0.44151(10) 0.67645(9) 0.55568(4) 0.01727(15) Uani 1 1 d . . . . .
C15 C 0.37413(11) 0.88285(9) 0.64936(5) 0.01870(16) Uani 1 1 d . . . . .
H15A H 0.3117(18) 0.9153(15) 0.6816(8) 0.030(4) Uiso 1 1 d . . . . .
H15B H 0.4317(16) 0.8082(14) 0.6702(7) 0.023(3) Uiso 1 1 d . . . . .
C16 C 0.48324(11) 0.98832(10) 0.64070(5) 0.02286(18) Uani 1 1 d . . . . .
H16A H 0.5448(19) 1.0093(16) 0.6844(9) 0.036(4) Uiso 1 1 d . . . . .
H16B H 0.5481(17) 0.9588(15) 0.6139(8) 0.027(4) Uiso 1 1 d . . . . .
C17 C 0.40200(13) 1.10636(10) 0.60894(6) 0.02453(19) Uani 1 1 d . . . . .
H17A H 0.3474(19) 1.1407(17) 0.6408(9) 0.036(4) Uiso 1 1 d . . . . .
H17B H 0.4728(18) 1.1698(16) 0.6007(8) 0.034(4) Uiso 1 1 d . . . . .
C18 C 0.29413(11) 1.07585(9) 0.54337(5) 0.02146(17) Uani 1 1 d . . . . .
H18A H 0.3478(17) 1.0534(14) 0.5062(8) 0.026(4) Uiso 1 1 d . . . . .
H18B H 0.2382(17) 1.1499(15) 0.5270(8) 0.029(4) Uiso 1 1 d . . . . .
C19 C 0.18808(10) 0.96818(9) 0.55205(5) 0.01850(16) Uani 1 1 d . . . . .
H19A H 0.1209(16) 0.9473(14) 0.5070(7) 0.024(3) Uiso 1 1 d . . . . .
H19B H 0.1262(17) 0.9966(15) 0.5823(8) 0.026(4) Uiso 1 1 d . . . . .
O6 O 0.83355(8) 0.56466(7) 0.53619(4) 0.02104(14) Uani 1 1 d . . . . .
H6A H 0.852(2) 0.508(2) 0.5729(10) 0.052(5) Uiso 1 1 d . . . . .
H6B H 0.742(2) 0.5970(19) 0.5384(10) 0.049(5) Uiso 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3352(13) . ?
O1 N1 1.4279(13) . ?
O2 C6 1.4056(11) . ?
O2 H2 0.894(17) . ?
O3 C7 1.2167(12) . ?
O4 C10 1.4128(11) . ?
O4 H4 0.91(2) . ?
O5 C14 1.2350(11) . ?
N1 C1 1.2955(14) . ?
N2 C3 1.2944(13) . ?
N2 C1 1.3811(13) . ?
N3 C14 1.3583(12) . ?
N3 C6 1.4604(12) . ?
N3 C5 1.4721(12) . ?
C1 C2 1.4813(15) . ?
C2 H2A 0.95(2) . ?
C2 H2B 0.99(2) . ?
C2 H2C 0.980(18) . ?
C3 C4 1.4824(14) . ?
C4 C5 1.5366(14) . ?
C4 H4A 0.984(15) . ?
C4 H4B 0.987(16) . ?
C5 H5A 0.992(15) . ?
C5 H5B 0.948(15) . ?
C6 C7 1.5486(13) . ?
C6 C10 1.5772(13) . ?
C7 C8 1.4554(14) . ?
C8 C9 1.3430(14) . ?
C8 H8 0.991(17) . ?
C9 C11 1.4954(14) . ?
C9 C10 1.5290(12) . ?
C10 C12 1.5576(12) . ?
C11 H11A 0.943(19) . ?
C11 H11B 0.973(19) . ?
C11 H11C 0.977(18) . ?
C12 C13 1.5320(12) . ?
C12 C19 1.5413(13) . ?
C12 C15 1.5457(13) . ?
C13 C14 1.4973(13) . ?
C13 H13A 0.958(15) . ?
C13 H13B 0.970(16) . ?
C15 C16 1.5346(14) . ?
C15 H15A 1.013(16) . ?
C15 H15B 0.996(15) . ?
C16 C17 1.5295(15) . ?
C16 H16A 0.976(17) . ?
C16 H16B 0.937(16) . ?
C17 C18 1.5243(15) . ?
C17 H17A 0.965(17) . ?
C17 H17B 0.973(17) . ?
C18 C19 1.5329(14) . ?
C18 H18A 1.008(16) . ?
C18 H18B 0.960(16) . ?
C19 H19A 1.019(15) . ?
C19 H19B 0.965(15) . ?
O6 H6A 0.94(2) . ?
O6 H6B 0.92(2) . ?

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 O1 N1 106.12(8) . . ?
C6 O2 H2 114.0(11) . . ?
C10 O4 H4 106.4(12) . . ?
C1 N1 O1 103.63(9) . . ?
C3 N2 C1 103.65(8) . . ?
C14 N3 C6 123.56(8) . . ?
C14 N3 C5 116.77(8) . . ?
C6 N3 C5 118.53(8) . . ?
N1 C1 N2 113.72(9) . . ?
N1 C1 C2 123.20(9) . . ?
N2 C1 C2 123.08(9) . . ?
C1 C2 H2A 109.6(12) . . ?
C1 C2 H2B 110.3(11) . . ?
H2A C2 H2B 107.3(16) . . ?
C1 C2 H2C 111.8(10) . . ?
H2A C2 H2C 106.5(15) . . ?
H2B C2 H2C 111.2(15) . . ?
N2 C3 O1 112.87(9) . . ?
N2 C3 C4 127.83(9) . . ?
O1 C3 C4 119.27(9) . . ?
C3 C4 C5 111.23(8) . . ?
C3 C4 H4A 107.0(9) . . ?
C5 C4 H4A 110.0(8) . . ?
C3 C4 H4B 110.8(9) . . ?
C5 C4 H4B 109.8(9) . . ?
H4A C4 H4B 107.9(13) . . ?
N3 C5 C4 110.79(8) . . ?
N3 C5 H5A 107.0(9) . . ?
C4 C5 H5A 109.8(9) . . ?
N3 C5 H5B 106.8(9) . . ?
C4 C5 H5B 113.2(9) . . ?
H5A C5 H5B 109.1(13) . . ?
O2 C6 N3 109.84(7) . . ?
O2 C6 C7 102.41(7) . . ?
N3 C6 C7 113.88(8) . . ?
O2 C6 C10 110.81(7) . . ?
N3 C6 C10 115.39(7) . . ?
C7 C6 C10 103.65(7) . . ?
O3 C7 C8 128.37(9) . . ?
O3 C7 C6 125.03(9) . . ?
C8 C7 C6 106.49(8) . . ?
C9 C8 C7 111.23(8) . . ?
C9 C8 H8 124.5(10) . . ?
C7 C8 H8 124.2(10) . . ?
C8 C9 C11 124.82(9) . . ?
C8 C9 C10 112.49(8) . . ?
C11 C9 C10 122.66(8) . . ?
O4 C10 C9 111.25(7) . . ?
O4 C10 C12 106.55(7) . . ?
C9 C10 C12 114.49(7) . . ?
O4 C10 C6 111.13(7) . . ?
C9 C10 C6 101.51(7) . . ?
C12 C10 C6 112.00(7) . . ?
C9 C11 H11A 112.3(11) . . ?
C9 C11 H11B 111.5(11) . . ?
H11A C11 H11B 108.9(16) . . ?
C9 C11 H11C 108.4(11) . . ?
H11A C11 H11C 106.2(15) . . ?
H11B C11 H11C 109.4(15) . . ?
C13 C12 C19 108.64(7) . . ?
C13 C12 C15 111.71(7) . . ?
C19 C12 C15 108.48(7) . . ?
C13 C12 C10 104.03(7) . . ?
C19 C12 C10 111.81(7) . . ?
C15 C12 C10 112.11(7) . . ?
C14 C13 C12 113.51(7) . . ?
C14 C13 H13A 107.3(9) . . ?
C12 C13 H13A 109.3(9) . . ?
C14 C13 H13B 107.4(9) . . ?
C12 C13 H13B 112.6(9) . . ?
H13A C13 H13B 106.4(13) . . ?
O5 C14 N3 121.27(9) . . ?
O5 C14 C13 120.47(8) . . ?
N3 C14 C13 118.26(8) . . ?
C16 C15 C12 112.39(8) . . ?
C16 C15 H15A 107.3(9) . . ?
C12 C15 H15A 108.4(9) . . ?
C16 C15 H15B 108.7(9) . . ?
C12 C15 H15B 111.5(9) . . ?
H15A C15 H15B 108.5(12) . . ?
C17 C16 C15 111.47(8) . . ?
C17 C16 H16A 110.0(10) . . ?
C15 C16 H16A 109.6(10) . . ?
C17 C16 H16B 110.1(10) . . ?
C15 C16 H16B 109.3(10) . . ?
H16A C16 H16B 106.3(14) . . ?
C18 C17 C16 111.80(8) . . ?
C18 C17 H17A 109.0(10) . . ?
C16 C17 H17A 107.6(10) . . ?
C18 C17 H17B 109.8(10) . . ?
C16 C17 H17B 110.3(10) . . ?
H17A C17 H17B 108.2(14) . . ?
C17 C18 C19 112.07(8) . . ?
C17 C18 H18A 111.7(9) . . ?
C19 C18 H18A 109.3(9) . . ?
C17 C18 H18B 109.8(9) . . ?
C19 C18 H18B 109.7(9) . . ?
H18A C18 H18B 104.1(12) . . ?
C18 C19 C12 112.96(8) . . ?
C18 C19 H19A 110.1(8) . . ?
C12 C19 H19A 109.6(8) . . ?
C18 C19 H19B 108.1(9) . . ?
C12 C19 H19B 107.9(9) . . ?
H19A C19 H19B 107.9(12) . . ?
H6A O6 H6B 102.9(17) . . ?

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 O1 N1 C1 -0.10(13) . . . . ?
O1 N1 C1 N2 -0.33(14) . . . . ?
O1 N1 C1 C2 179.54(11) . . . . ?
C3 N2 C1 N1 0.65(13) . . . . ?
C3 N2 C1 C2 -179.22(10) . . . . ?
C1 N2 C3 O1 -0.70(12) . . . . ?
C1 N2 C3 C4 -178.73(10) . . . . ?
N1 O1 C3 N2 0.53(13) . . . . ?
N1 O1 C3 C4 178.75(9) . . . . ?
N2 C3 C4 C5 96.48(13) . . . . ?
O1 C3 C4 C5 -81.44(12) . . . . ?
C14 N3 C5 C4 78.43(10) . . . . ?
C6 N3 C5 C4 -113.33(9) . . . . ?
C3 C4 C5 N3 -159.45(8) . . . . ?
C14 N3 C6 O2 113.57(9) . . . . ?
C5 N3 C6 O2 -53.82(10) . . . . ?
C14 N3 C6 C7 -132.25(9) . . . . ?
C5 N3 C6 C7 60.36(11) . . . . ?
C14 N3 C6 C10 -12.53(12) . . . . ?
C5 N3 C6 C10 -179.92(7) . . . . ?
O2 C6 C7 O3 80.59(12) . . . . ?
N3 C6 C7 O3 -37.92(13) . . . . ?
C10 C6 C7 O3 -164.08(10) . . . . ?
O2 C6 C7 C8 -95.75(9) . . . . ?
N3 C6 C7 C8 145.73(8) . . . . ?
C10 C6 C7 C8 19.57(10) . . . . ?
O3 C7 C8 C9 173.25(11) . . . . ?
C6 C7 C8 C9 -10.57(12) . . . . ?
C7 C8 C9 C11 174.62(10) . . . . ?
C7 C8 C9 C10 -3.72(13) . . . . ?
C8 C9 C10 O4 134.08(9) . . . . ?
C11 C9 C10 O4 -44.30(12) . . . . ?
C8 C9 C10 C12 -105.05(10) . . . . ?
C11 C9 C10 C12 76.57(12) . . . . ?
C8 C9 C10 C6 15.80(11) . . . . ?
C11 C9 C10 C6 -162.58(9) . . . . ?
O2 C6 C10 O4 -29.66(9) . . . . ?
N3 C6 C10 O4 95.95(9) . . . . ?
C7 C6 C10 O4 -138.86(7) . . . . ?
O2 C6 C10 C9 88.71(8) . . . . ?
N3 C6 C10 C9 -145.68(8) . . . . ?
C7 C6 C10 C9 -20.49(9) . . . . ?
O2 C6 C10 C12 -148.71(7) . . . . ?
N3 C6 C10 C12 -23.10(10) . . . . ?
C7 C6 C10 C12 102.10(8) . . . . ?
O4 C10 C12 C13 -64.94(8) . . . . ?
C9 C10 C12 C13 171.63(7) . . . . ?
C6 C10 C12 C13 56.77(9) . . . . ?
O4 C10 C12 C19 52.11(9) . . . . ?
C9 C10 C12 C19 -71.31(9) . . . . ?
C6 C10 C12 C19 173.82(7) . . . . ?
O4 C10 C12 C15 174.20(7) . . . . ?
C9 C10 C12 C15 50.77(10) . . . . ?
C6 C10 C12 C15 -64.09(9) . . . . ?
C19 C12 C13 C14 178.86(8) . . . . ?
C15 C12 C13 C14 59.23(10) . . . . ?
C10 C12 C13 C14 -61.90(9) . . . . ?
C6 N3 C14 O5 -171.44(9) . . . . ?
C5 N3 C14 O5 -3.85(13) . . . . ?
C6 N3 C14 C13 9.28(13) . . . . ?
C5 N3 C14 C13 176.88(8) . . . . ?
C12 C13 C14 O5 -148.55(9) . . . . ?
C12 C13 C14 N3 30.73(12) . . . . ?
C13 C12 C15 C16 63.72(10) . . . . ?
C19 C12 C15 C16 -56.00(10) . . . . ?
C10 C12 C15 C16 -179.96(8) . . . . ?
C12 C15 C16 C17 56.21(11) . . . . ?
C15 C16 C17 C18 -53.26(12) . . . . ?
C16 C17 C18 C19 52.34(12) . . . . ?
C17 C18 C19 C12 -54.43(11) . . . . ?
C13 C12 C19 C18 -66.56(10) . . . . ?
C15 C12 C19 C18 55.06(10) . . . . ?
C10 C12 C19 C18 179.20(7) . . . . ?

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
_geom_hbond_publ_flag
O2 H2 O6 0.894(17) 1.812(18) 2.6926(10) 168.1(16) 3_666 yes
O4 H4 O6 0.91(2) 1.82(2) 2.7307(10) 171.4(18) 1_455 yes
O6 H6A N2 0.94(2) 1.91(2) 2.8324(11) 164.3(18) . yes
O6 H6B O5 0.92(2) 1.78(2) 2.6990(10) 175.8(19) . yes

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.054

