# Electronic Supplementary Material (ESI) for RSC Chemical Biology.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2166141'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2022-05-15 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   6.3200(10)
_cell_length_b                   9.739(3)
_cell_length_c                   11.787(2)
_cell_angle_alpha                114.044(12)
_cell_angle_beta                 100.295(13)
_cell_angle_gamma                94.954(16)
_cell_volume                     641.6(3)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C11 H17 N3 O5 
# Dc =      1.40 Fooo =    298.00 Mu =      9.47 M =    542.55
# Found Formula = C11 H18 N3 O5.50 
# Dc =      1.45 FOOO =    298.00 Mu =      9.95 M =    560.56

_chemical_formula_sum            'C11 H18 N3 O5.50'
_chemical_formula_moiety         'C11 H18 N3 O5.50'
_chemical_compound_source        ?
_chemical_formula_weight         280.28


_cell_measurement_reflns_used    88
_cell_measurement_theta_min      12.4544
_cell_measurement_theta_max      55.3152
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.112
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_max          0.292

_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             298
_exptl_absorpt_coefficient_mu    0.995

# Sheldrick geometric approximatio 0.83 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            14217
_reflns_number_total             4416
_diffrn_reflns_av_R_equivalents  0.020
# Number of reflections without Friedels Law is 4416 
# Number of reflections with Friedels Law is 2295 
# Theoretical number of reflections is about 2299 


_diffrn_reflns_theta_min         4.225
_diffrn_reflns_theta_max         67.214
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        66.384
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              -14
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.54
_oxford_diffrn_Wilson_scale      2.72

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.15
_refine_diff_density_max         0.45


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     3
_refine_ls_number_parameters     354
_oxford_refine_ls_R_factor_ref   0.0333
_refine_ls_wR_factor_ref         0.0386
_refine_ls_goodness_of_fit_ref   1.1080
_refine_ls_shift/su_max          0.0002379
_refine_ls_shift/su_mean         0.0000460


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4416
_refine_ls_R_factor_all          0.0335
_refine_ls_wR_factor_all         0.0389

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4371
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_gt          0.0386

_refine_ls_abs_structure_Flack   0.13(13)
_refine_ls_abs_structure_details 'Flack (1983), 2121 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.212 0.136 0.315E-01 -0.497E-02 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.6492(3) 0.32061(19) 0.51337(17) 0.0291 1.0000 Uani . . . . . .
C2 C 0.7534(3) 0.26394(19) 0.60830(18) 0.0302 1.0000 Uani . . . . . .
C3 C 0.5567(3) 0.20750(18) 0.64640(16) 0.0260 1.0000 Uani . . . . . .
C4 C 0.4031(3) 0.3181(2) 0.63900(17) 0.0296 1.0000 Uani . . . . . .
C5 C 0.4124(4) 0.4497(2) 0.7670(2) 0.0471 1.0000 Uani . . . . . .
O6 O 0.4669(2) 0.37962(17) 0.55591(15) 0.0399 1.0000 Uani . . . . . .
O7 O 0.4584(2) 0.05312(14) 0.56537(13) 0.0360 1.0000 Uani . . . . . .
O8 O 0.2914(3) 0.40540(18) 0.84055(15) 0.0510 1.0000 Uani . . . . . .
N9 N 0.7920(2) 0.44424(16) 0.50638(14) 0.0292 1.0000 Uani . . . . . .
C10 C 0.9350(3) 0.4013(2) 0.42553(18) 0.0313 1.0000 Uani . . . . . .
O11 O 0.9428(3) 0.26440(15) 0.36930(16) 0.0479 1.0000 Uani . . . . . .
N12 N 1.0576(3) 0.51214(18) 0.41201(15) 0.0321 1.0000 Uani . . . . . .
C13 C 1.0424(3) 0.6576(2) 0.47496(16) 0.0273 1.0000 Uani . . . . . .
N14 N 1.1629(3) 0.75951(18) 0.45368(17) 0.0392 1.0000 Uani . . . . . .
C15 C 0.8971(3) 0.70624(19) 0.55880(16) 0.0268 1.0000 Uani . . . . . .
C16 C 0.7739(3) 0.5936(2) 0.56957(17) 0.0287 1.0000 Uani . . . . . .
C17 C 0.8717(3) 0.8717(2) 0.62366(17) 0.0303 1.0000 Uani . . . . . .
C18 C 1.0666(4) 0.9718(2) 0.7306(2) 0.0466 1.0000 Uani . . . . . .
C21 C 0.8549(3) 0.89881(19) 0.18845(16) 0.0259 1.0000 Uani . . . . . .
C22 C 1.0970(3) 0.9347(2) 0.24894(18) 0.0336 1.0000 Uani . . . . . .
C23 C 1.1960(3) 0.9904(2) 0.16350(19) 0.0356 1.0000 Uani . . . . . .
C24 C 1.0467(3) 0.8927(2) 0.03276(19) 0.0357 1.0000 Uani . . . . . .
C25 C 1.1168(4) 0.7500(3) -0.0521(2) 0.0535 1.0000 Uani . . . . . .
O26 O 0.8362(2) 0.85369(15) 0.05541(12) 0.0323 1.0000 Uani . . . . . .
O27 O 1.1938(3) 1.14613(16) 0.19585(17) 0.0606 1.0000 Uani . . . . . .
O28 O 1.1704(3) 0.6643(2) 0.01523(18) 0.0650 1.0000 Uani . . . . . .
N29 N 0.7365(2) 0.77248(16) 0.20278(14) 0.0251 1.0000 Uani . . . . . .
C30 C 0.6111(3) 0.80535(18) 0.29274(15) 0.0246 1.0000 Uani . . . . . .
O31 O 0.6048(2) 0.94148(14) 0.35864(12) 0.0366 1.0000 Uani . . . . . .
N32 N 0.5026(2) 0.68999(16) 0.30575(14) 0.0281 1.0000 Uani . . . . . .
C33 C 0.5231(3) 0.54514(19) 0.23666(15) 0.0270 1.0000 Uani . . . . . .
N34 N 0.4113(3) 0.43800(18) 0.25531(16) 0.0383 1.0000 Uani . . . . . .
C35 C 0.6644(3) 0.50823(19) 0.14955(16) 0.0264 1.0000 Uani . . . . . .
C36 C 0.7653(3) 0.6263(2) 0.13667(16) 0.0277 1.0000 Uani . . . . . .
C37 C 0.6970(3) 0.3458(2) 0.07844(17) 0.0307 1.0000 Uani . . . . . .
C38 C 0.8888(4) 0.3323(2) 0.0162(2) 0.0460 1.0000 Uani . . . . . .
O39 O 0.4967(2) 0.26400(15) -0.01498(13) 0.0398 1.0000 Uani . . . . . .
O19 O 0.6813(2) 0.88156(16) 0.67351(14) 0.0417 1.0000 Uani . . . . . .
O40 O 0.5541(3) -0.03830(17) -0.09313(15) 0.0477 1.0000 Uani . . . . . .
H21 H 0.8505 0.3475 0.6829 0.0361 1.0000 Uiso R . . . . .
H22 H 0.8317 0.1815 0.5704 0.0368 1.0000 Uiso R . . . . .
H211 H 0.7862 0.9899 0.2266 0.0304 1.0000 Uiso R . . . . .
H31 H 0.5980 0.2163 0.7324 0.0309 1.0000 Uiso R . . . . .
H361 H 0.8590 0.6108 0.0815 0.0328 1.0000 Uiso R . . . . .
H222 H 1.1287 1.0132 0.3369 0.0405 1.0000 Uiso R . . . . .
H221 H 1.1474 0.8432 0.2462 0.0385 1.0000 Uiso R . . . . .
H11 H 0.6031 0.2363 0.4272 0.0342 1.0000 Uiso R . . . . .
H171 H 0.8558 0.9106 0.5582 0.0357 1.0000 Uiso R . . . . .
H161 H 0.6692 0.6138 0.6185 0.0343 1.0000 Uiso R . . . . .
H231 H 1.3447 0.9702 0.1629 0.0421 1.0000 Uiso R . . . . .
H371 H 0.7248 0.3018 0.1404 0.0356 1.0000 Uiso R . . . . .
H41 H 0.2576 0.2608 0.6018 0.0363 1.0000 Uiso R . . . . .
H241 H 1.0277 0.9582 -0.0127 0.0435 1.0000 Uiso R . . . . .
H181 H 1.0466 1.0790 0.7690 0.0711 1.0000 Uiso R . . . . .
H182 H 1.2000 0.9703 0.7002 0.0702 1.0000 Uiso R . . . . .
H183 H 1.0832 0.9330 0.7956 0.0689 1.0000 Uiso R . . . . .
H381 H 0.9008 0.2281 -0.0263 0.0690 1.0000 Uiso R . . . . .
H382 H 1.0258 0.3879 0.0772 0.0687 1.0000 Uiso R . . . . .
H383 H 0.8636 0.3721 -0.0478 0.0689 1.0000 Uiso R . . . . .
H51 H 0.5644 0.4917 0.8152 0.0561 1.0000 Uiso R . . . . .
H52 H 0.3438 0.5264 0.7499 0.0569 1.0000 Uiso R . . . . .
H341 H 0.3958 0.3424 0.2051 0.0457 1.0000 Uiso R . . . . .
H142 H 1.1773 0.8583 0.4998 0.0457 1.0000 Uiso R . . . . .
H71 H 0.4916 0.0243 0.4962 0.0529 1.0000 Uiso R . . . . .
H141 H 1.2538 0.7303 0.4037 0.0464 1.0000 Uiso R . . . . .
H342 H 0.3279 0.4650 0.3095 0.0462 1.0000 Uiso R . . . . .
H402 H 0.6063 -0.0681 -0.1576 0.0709 1.0000 Uiso R . . . . .
H271 H 1.1187 1.1842 0.2446 0.0909 1.0000 Uiso R . . . . .
H81 H 0.3654 0.3616 0.8762 0.0768 1.0000 Uiso R . . . . .
H401 H 0.6229 -0.0675 -0.0417 0.0716 1.0000 Uiso R . . . . .
H391 H 0.5021 0.1734 -0.0419 0.0604 1.0000 Uiso R . . . . .
H281 H 1.1900 0.5871 -0.0472 0.0987 1.0000 Uiso R . . . . .
H191 H 0.5953 0.9138 0.6331 0.0618 1.0000 Uiso R . . . . .
H252 H 1.2405 0.7768 -0.0791 0.0646 1.0000 Uiso R . . . . .
H251 H 1.0005 0.6915 -0.1247 0.0646 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       53(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.6278(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.514(2) yes
C1 . O6 . 1.412(2) yes
C1 . N9 . 1.480(2) yes
C1 . H11 . 0.982 no
C2 . C3 . 1.527(2) yes
C2 . H21 . 0.975 no
C2 . H22 . 0.971 no
C3 . C4 . 1.529(2) yes
C3 . O7 . 1.420(2) yes
C3 . H31 . 0.967 no
C4 . C5 . 1.517(3) yes
C4 . O6 . 1.435(2) yes
C4 . H41 . 0.958 no
C5 . O8 . 1.417(3) yes
C5 . H51 . 0.980 no
C5 . H52 . 0.967 no
O7 . H71 . 0.820 no
O8 . H81 . 0.830 no
N9 . C10 . 1.395(2) yes
N9 . C16 . 1.363(2) yes
C10 . O11 . 1.234(2) yes
C10 . N12 . 1.353(2) yes
N12 . C13 . 1.327(2) yes
C13 . N14 . 1.329(2) yes
C13 . C15 . 1.436(2) yes
N14 . H142 . 0.878 no
N14 . H141 . 0.878 no
C15 . C16 . 1.352(2) yes
C15 . C17 . 1.514(2) yes
C16 . H161 . 0.936 no
C17 . C18 . 1.514(3) yes
C17 . O19 . 1.424(2) yes
C17 . H171 . 0.983 no
C18 . H181 . 0.985 no
C18 . H182 . 0.972 no
C18 . H183 . 0.977 no
C21 . C22 . 1.512(3) yes
C21 . O26 . 1.425(2) yes
C21 . N29 . 1.469(2) yes
C21 . H211 . 0.994 no
C22 . C23 . 1.520(2) yes
C22 . H222 . 0.977 no
C22 . H221 . 0.962 no
C23 . C24 . 1.517(3) yes
C23 . O27 . 1.407(2) yes
C23 . H231 . 0.978 no
C24 . C25 . 1.503(3) yes
C24 . O26 . 1.452(2) yes
C24 . H241 . 0.989 no
C25 . O28 . 1.390(3) yes
C25 . H252 . 0.950 no
C25 . H251 . 0.950 no
O27 . H271 . 0.804 no
O28 . H281 . 0.849 no
N29 . C30 . 1.386(2) yes
N29 . C36 . 1.363(2) yes
C30 . O31 . 1.243(2) yes
C30 . N32 . 1.342(2) yes
N32 . C33 . 1.343(2) yes
C33 . N34 . 1.324(2) yes
C33 . C35 . 1.437(2) yes
N34 . H341 . 0.861 no
N34 . H342 . 0.873 no
C35 . C36 . 1.343(2) yes
C35 . C37 . 1.512(2) yes
C36 . H361 . 0.933 no
C37 . C38 . 1.513(3) yes
C37 . O39 . 1.436(2) yes
C37 . H371 . 0.985 no
C38 . H381 . 0.949 no
C38 . H382 . 0.969 no
C38 . H383 . 0.975 no
O39 . H391 . 0.813 no
O19 . H191 . 0.824 no
O40 . H402 . 0.835 no
O40 . H401 . 0.839 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . O6 . 105.75(14) yes
C2 . C1 . N9 . 114.39(14) yes
O6 . C1 . N9 . 107.79(14) yes
C2 . C1 . H11 . 110.4 no
O6 . C1 . H11 . 110.7 no
N9 . C1 . H11 . 107.7 no
C1 . C2 . C3 . 102.65(13) yes
C1 . C2 . H21 . 110.8 no
C3 . C2 . H21 . 109.8 no
C1 . C2 . H22 . 112.3 no
C3 . C2 . H22 . 110.9 no
H21 . C2 . H22 . 110.2 no
C2 . C3 . C4 . 102.04(12) yes
C2 . C3 . O7 . 113.90(13) yes
C4 . C3 . O7 . 111.93(14) yes
C2 . C3 . H31 . 110.7 no
C4 . C3 . H31 . 110.9 no
O7 . C3 . H31 . 107.4 no
C3 . C4 . C5 . 113.90(16) yes
C3 . C4 . O6 . 106.95(13) yes
C5 . C4 . O6 . 108.44(15) yes
C3 . C4 . H41 . 107.9 no
C5 . C4 . H41 . 110.2 no
O6 . C4 . H41 . 109.3 no
C4 . C5 . O8 . 112.04(17) yes
C4 . C5 . H51 . 110.3 no
O8 . C5 . H51 . 109.9 no
C4 . C5 . H52 . 107.3 no
O8 . C5 . H52 . 106.6 no
H51 . C5 . H52 . 110.6 no
C4 . O6 . C1 . 110.28(13) yes
C3 . O7 . H71 . 111.1 no
C5 . O8 . H81 . 109.3 no
C1 . N9 . C10 . 117.37(14) yes
C1 . N9 . C16 . 121.23(14) yes
C10 . N9 . C16 . 121.25(14) yes
N9 . C10 . O11 . 118.62(15) yes
N9 . C10 . N12 . 118.26(15) yes
O11 . C10 . N12 . 123.12(16) yes
C10 . N12 . C13 . 120.51(15) yes
N12 . C13 . N14 . 117.03(15) yes
N12 . C13 . C15 . 122.85(15) yes
N14 . C13 . C15 . 120.07(16) yes
C13 . N14 . H142 . 122.4 no
C13 . N14 . H141 . 120.2 no
H142 . N14 . H141 . 116.1 no
C13 . C15 . C16 . 115.69(15) yes
C13 . C15 . C17 . 122.17(15) yes
C16 . C15 . C17 . 122.01(15) yes
N9 . C16 . C15 . 121.44(16) yes
N9 . C16 . H161 . 116.8 no
C15 . C16 . H161 . 121.7 no
C15 . C17 . C18 . 113.52(16) yes
C15 . C17 . O19 . 109.82(15) yes
C18 . C17 . O19 . 108.87(15) yes
C15 . C17 . H171 . 107.0 no
C18 . C17 . H171 . 107.8 no
O19 . C17 . H171 . 109.7 no
C17 . C18 . H181 . 111.4 no
C17 . C18 . H182 . 111.6 no
H181 . C18 . H182 . 107.1 no
C17 . C18 . H183 . 108.0 no
H181 . C18 . H183 . 109.6 no
H182 . C18 . H183 . 109.2 no
C22 . C21 . O26 . 106.05(13) yes
C22 . C21 . N29 . 113.53(13) yes
O26 . C21 . N29 . 107.78(13) yes
C22 . C21 . H211 . 110.5 no
O26 . C21 . H211 . 111.4 no
N29 . C21 . H211 . 107.6 no
C21 . C22 . C23 . 103.07(14) yes
C21 . C22 . H222 . 110.9 no
C23 . C22 . H222 . 111.8 no
C21 . C22 . H221 . 109.8 no
C23 . C22 . H221 . 110.6 no
H222 . C22 . H221 . 110.4 no
C22 . C23 . C24 . 102.38(15) yes
C22 . C23 . O27 . 113.18(15) yes
C24 . C23 . O27 . 110.13(17) yes
C22 . C23 . H231 . 111.6 no
C24 . C23 . H231 . 109.6 no
O27 . C23 . H231 . 109.8 no
C23 . C24 . C25 . 117.75(19) yes
C23 . C24 . O26 . 106.03(14) yes
C25 . C24 . O26 . 109.69(16) yes
C23 . C24 . H241 . 107.2 no
C25 . C24 . H241 . 108.2 no
O26 . C24 . H241 . 107.5 no
C24 . C25 . O28 . 109.46(18) yes
C24 . C25 . H252 . 109.5 no
O28 . C25 . H252 . 109.5 no
C24 . C25 . H251 . 109.5 no
O28 . C25 . H251 . 109.5 no
H252 . C25 . H251 . 109.5 no
C24 . O26 . C21 . 110.12(13) yes
C23 . O27 . H271 . 114.6 no
C25 . O28 . H281 . 96.6 no
C21 . N29 . C30 . 119.08(13) yes
C21 . N29 . C36 . 120.24(14) yes
C30 . N29 . C36 . 120.42(14) yes
N29 . C30 . O31 . 118.24(14) yes
N29 . C30 . N32 . 119.12(14) yes
O31 . C30 . N32 . 122.64(15) yes
C30 . N32 . C33 . 120.42(14) yes
N32 . C33 . N34 . 116.73(16) yes
N32 . C33 . C35 . 121.78(15) yes
N34 . C33 . C35 . 121.47(16) yes
C33 . N34 . H341 . 122.1 no
C33 . N34 . H342 . 118.8 no
H341 . N34 . H342 . 117.8 no
C33 . C35 . C36 . 115.92(15) yes
C33 . C35 . C37 . 121.32(15) yes
C36 . C35 . C37 . 122.75(15) yes
N29 . C36 . C35 . 122.07(15) yes
N29 . C36 . H361 . 117.3 no
C35 . C36 . H361 . 120.6 no
C35 . C37 . C38 . 114.01(16) yes
C35 . C37 . O39 . 106.94(14) yes
C38 . C37 . O39 . 110.96(16) yes
C35 . C37 . H371 . 107.9 no
C38 . C37 . H371 . 107.3 no
O39 . C37 . H371 . 109.6 no
C37 . C38 . H381 . 109.9 no
C37 . C38 . H382 . 112.5 no
H381 . C38 . H382 . 108.7 no
C37 . C38 . H383 . 109.2 no
H381 . C38 . H383 . 107.7 no
H382 . C38 . H383 . 108.7 no
C37 . O39 . H391 . 107.5 no
C17 . O19 . H191 . 106.8 no
H402 . O40 . H401 . 107.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C21 . H211 . O11 1_565 132.43(5) 0.994 2.498 3.253(3) yes
C36 . H361 . O28 . 156.29(6) 0.933 2.336 3.212(3) yes
N34 . H341 . O27 1_445 130.70(6) 0.861 2.157 2.796(3) yes
N14 . H142 . O7 1_665 132.49(5) 0.878 2.255 2.920(3) yes
O7 . H71 . O31 1_545 167.69(6) 0.820 1.800 2.607(3) yes
N14 . H141 . N32 1_655 171.39(6) 0.878 2.085 2.956(3) yes
N34 . H342 . N12 1_455 168.13(6) 0.873 2.238 3.098(3) yes
O40 . H402 . O19 1_544 167.44(5) 0.835 2.002 2.823(3) yes
O27 . H271 . O11 1_565 174.97(7) 0.804 1.951 2.753(3) yes
O8 . H81 . O39 1_556 167.71(6) 0.830 1.996 2.812(3) yes
O40 . H401 . O26 1_545 166.87(5) 0.839 2.015 2.839(3) yes
O39 . H391 . O40 . 172.54(6) 0.813 1.974 2.783(3) yes
O28 . H281 . O8 1_654 165.89(8) 0.849 1.971 2.801(3) yes
O19 . H191 . O7 1_565 161.64(6) 0.824 2.017 2.811(3) yes


####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2166142'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2022-05-15 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.6129(6)
_cell_length_b                   9.1399(7)
_cell_length_c                   11.2377(9)
_cell_angle_alpha                91.092(2)
_cell_angle_beta                 103.921(2)
_cell_angle_gamma                112.0703(19)
_cell_volume                     698.12(10)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C12 H19 N3 O5 
# Dc =      1.36 Fooo =    304.00 Mu =      8.97 M =    570.60
# Found Formula = C12 H19.00 N3 O5 
# Dc =      1.36 FOOO =    304.00 Mu =      8.97 M =    570.60

_chemical_formula_sum            'C12 H19.00 N3 O5'
_chemical_formula_moiety         'C12 H19.00 N3 O5'
_chemical_compound_source        ?
_chemical_formula_weight         285.30


_cell_measurement_reflns_used    9585
_cell_measurement_theta_min      4.0833
_cell_measurement_theta_max      68.4420
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.171
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_max          0.483

_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             303.998
_exptl_absorpt_coefficient_mu    0.897

# Sheldrick geometric approximatio 0.81 0.86 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.86
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            19653
_reflns_number_total             4807
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 4807 
# Number of reflections with Friedels Law is 2493 
# Theoretical number of reflections is about 2492 


_diffrn_reflns_theta_min         4.083
_diffrn_reflns_theta_max         67.055
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        67.055
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              -13
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.84
_oxford_diffrn_Wilson_scale      7.19

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.40


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4786
_refine_ls_number_restraints     3
_refine_ls_number_parameters     363
_oxford_refine_ls_R_factor_ref   0.0256
_refine_ls_wR_factor_ref         0.0306
_refine_ls_goodness_of_fit_ref   0.8803
_refine_ls_shift/su_max          0.0003414
_refine_ls_shift/su_mean         0.0000369


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4807
_refine_ls_R_factor_all          0.0257
_refine_ls_wR_factor_all         0.0315

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4786
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_gt          0.0306

_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_abs_structure_details 'Flack (1983), 2314 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.384 0.464 0.229 0.587E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C -0.78888(18) 0.16548(15) -0.49497(12) 0.0180 1.0000 Uani . . . . . .
C2 C -0.7549(2) 0.03650(15) -0.41940(12) 0.0209 1.0000 Uani . . . . . .
C3 C -0.61728(19) 0.13052(15) -0.29636(12) 0.0197 1.0000 Uani . . . . . .
C4 C -0.49571(19) 0.28606(16) -0.33654(12) 0.0201 1.0000 Uani . . . . . .
C5 C -0.3177(2) 0.2826(2) -0.37336(15) 0.0322 1.0000 Uani . . . . . .
O6 O -0.63169(13) 0.31132(11) -0.43965(9) 0.0196 1.0000 Uani . . . . . .
O7 O -0.72032(14) 0.16267(12) -0.21503(9) 0.0239 1.0000 Uani . . . . . .
O8 O -0.17202(17) 0.29296(15) -0.26736(12) 0.0437 1.0000 Uani . . . . . .
N9 N -0.79164(16) 0.13806(13) -0.62626(10) 0.0184 1.0000 Uani . . . . . .
C10 C -0.96449(19) 0.02842(16) -0.70467(12) 0.0189 1.0000 Uani . . . . . .
O11 O -1.10253(15) -0.04572(12) -0.65956(9) 0.0268 1.0000 Uani . . . . . .
N12 N -0.97676(17) 0.00659(14) -0.82611(11) 0.0225 1.0000 Uani . . . . . .
C13 C -0.82240(19) 0.08683(16) -0.86900(12) 0.0201 1.0000 Uani . . . . . .
N14 N -0.84784(18) 0.06449(16) -0.99003(11) 0.0294 1.0000 Uani . . . . . .
C15 C -0.63724(19) 0.19414(15) -0.78939(13) 0.0186 1.0000 Uani . . . . . .
C16 C -0.63276(18) 0.21573(15) -0.67000(12) 0.0182 1.0000 Uani . . . . . .
C17 C -0.46303(18) 0.28303(15) -0.84000(12) 0.0186 1.0000 Uani . . . . . .
C18 C -0.3661(2) 0.17578(18) -0.87481(14) 0.0271 1.0000 Uani . . . . . .
C19 C -0.2200(3) 0.2545(2) -0.94907(17) 0.0395 1.0000 Uani . . . . . .
O20 O -0.31652(13) 0.41083(12) -0.75064(9) 0.0244 1.0000 Uani . . . . . .
C21 C -0.40436(19) -0.19898(16) -0.49755(12) 0.0193 1.0000 Uani . . . . . .
C22 C -0.4278(2) -0.35755(17) -0.55784(13) 0.0235 1.0000 Uani . . . . . .
C23 C -0.5343(2) -0.36312(16) -0.69195(13) 0.0214 1.0000 Uani . . . . . .
C24 C -0.6432(2) -0.25222(16) -0.68548(12) 0.0215 1.0000 Uani . . . . . .
C25 C -0.8642(2) -0.33901(19) -0.71336(16) 0.0345 1.0000 Uani . . . . . .
O26 O -0.57058(15) -0.17088(12) -0.56231(9) 0.0254 1.0000 Uani . . . . . .
O27 O -0.40543(14) -0.31768(12) -0.77033(9) 0.0250 1.0000 Uani . . . . . .
O28 O -0.90610(16) -0.46647(16) -0.64015(13) 0.0451 1.0000 Uani . . . . . .
N29 N -0.40382(15) -0.19873(13) -0.36698(10) 0.0182 1.0000 Uani . . . . . .
C30 C -0.24695(18) -0.08773(15) -0.27810(12) 0.0174 1.0000 Uani . . . . . .
O31 O -0.11550(14) 0.01975(12) -0.31190(9) 0.0233 1.0000 Uani . . . . . .
N32 N -0.23976(16) -0.09884(14) -0.15859(11) 0.0198 1.0000 Uani . . . . . .
C33 C -0.38035(19) -0.21521(16) -0.12361(12) 0.0196 1.0000 Uani . . . . . .
N34 N -0.35311(18) -0.22310(15) -0.00383(11) 0.0285 1.0000 Uani . . . . . .
C35 C -0.55368(18) -0.32574(15) -0.21290(12) 0.0188 1.0000 Uani . . . . . .
C36 C -0.55579(19) -0.31196(16) -0.33181(13) 0.0190 1.0000 Uani . . . . . .
C37 C -0.7216(2) -0.45013(16) -0.17534(13) 0.0224 1.0000 Uani . . . . . .
C38 C -0.8364(2) -0.38177(19) -0.11415(16) 0.0328 1.0000 Uani . . . . . .
C39 C -0.9346(3) -0.2930(3) -0.1987(2) 0.0551 1.0000 Uani . . . . . .
O40 O -0.64847(16) -0.54302(12) -0.09082(10) 0.0310 1.0000 Uani . . . . . .
H141 H -0.7549 0.1202 -1.0207 0.0313 1.0000 Uiso R . . . . .
H142 H -0.9550 -0.0012 -1.0359 0.0367 1.0000 Uiso R . . . . .
H21 H -0.8763 -0.0393 -0.4120 0.0248 1.0000 Uiso R . . . . .
H22 H -0.6954 -0.0189 -0.4591 0.0248 1.0000 Uiso R . . . . .
H71 H -0.8380 0.1167 -0.2403 0.0348 1.0000 Uiso R . . . . .
H31 H -0.5357 0.0759 -0.2556 0.0235 1.0000 Uiso R . . . . .
H81 H -0.1332 0.2129 -0.2655 0.0660 1.0000 Uiso R . . . . .
H52 H -0.2649 0.3787 -0.4152 0.0376 1.0000 Uiso R . . . . .
H51 H -0.3292 0.1935 -0.4377 0.0193 1.0000 Uiso R . . . . .
H41 H -0.4496 0.3781 -0.2725 0.0227 1.0000 Uiso R . . . . .
H11 H -0.9136 0.1728 -0.4986 0.0187 1.0000 Uiso R . . . . .
H161 H -0.5196 0.2835 -0.6148 0.0204 1.0000 Uiso R . . . . .
H191 H -0.1757 0.1799 -0.9791 0.0586 1.0000 Uiso R . . . . .
H192 H -0.2806 0.2917 -1.0174 0.0588 1.0000 Uiso R . . . . .
H193 H -0.1052 0.3375 -0.8976 0.0598 1.0000 Uiso R . . . . .
H182 H -0.4661 0.0745 -0.9211 0.0317 1.0000 Uiso R . . . . .
H181 H -0.2979 0.1491 -0.7985 0.0331 1.0000 Uiso R . . . . .
H171 H -0.5095 0.3239 -0.9120 0.0214 1.0000 Uiso R . . . . .
H201 H -0.3447 0.4922 -0.7572 0.0375 1.0000 Uiso R . . . . .
H281 H -1.0149 -0.5321 -0.6608 0.0677 1.0000 Uiso R . . . . .
H252 H -0.9178 -0.3804 -0.8008 0.0409 1.0000 Uiso R . . . . .
H251 H -0.9239 -0.2660 -0.6970 0.0411 1.0000 Uiso R . . . . .
H241 H -0.6117 -0.1706 -0.7399 0.0238 1.0000 Uiso R . . . . .
H341 H -0.2403 -0.1598 0.0484 0.0351 1.0000 Uiso R . . . . .
H342 H -0.4275 -0.3066 0.0193 0.0319 1.0000 Uiso R . . . . .
H361 H -0.6610 -0.3785 -0.3954 0.0209 1.0000 Uiso R . . . . .
H401 H -0.6626 -0.6189 -0.1389 0.0467 1.0000 Uiso R . . . . .
H392 H -1.0107 -0.2544 -0.1588 0.0815 1.0000 Uiso R . . . . .
H393 H -1.0203 -0.3588 -0.2743 0.0818 1.0000 Uiso R . . . . .
H391 H -0.8385 -0.2002 -0.2213 0.0812 1.0000 Uiso R . . . . .
H382 H -0.9366 -0.4679 -0.0897 0.0379 1.0000 Uiso R . . . . .
H381 H -0.7466 -0.3109 -0.0417 0.0403 1.0000 Uiso R . . . . .
H371 H -0.8128 -0.5180 -0.2471 0.0245 1.0000 Uiso R . . . . .
H211 H -0.2840 -0.1124 -0.5038 0.0220 1.0000 Uiso R . . . . .
H221 H -0.5066 -0.4432 -0.5231 0.0267 1.0000 Uiso R . . . . .
H222 H -0.3006 -0.3599 -0.5493 0.0270 1.0000 Uiso R . . . . .
H231 H -0.6272 -0.4724 -0.7246 0.0241 1.0000 Uiso R . . . . .
H271 H -0.3056 -0.2318 -0.7365 0.0396 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       98(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.3843(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.5296(19) yes
C1 . O6 . 1.4167(15) yes
C1 . N9 . 1.4857(16) yes
C1 . H11 . 0.968 no
C2 . C3 . 1.5261(18) yes
C2 . H21 . 0.948 no
C2 . H22 . 0.960 no
C3 . C4 . 1.5226(18) yes
C3 . O7 . 1.4300(16) yes
C3 . H31 . 0.974 no
C4 . C5 . 1.520(2) yes
C4 . O6 . 1.4424(16) yes
C4 . H41 . 0.991 no
C5 . O8 . 1.393(2) yes
C5 . H52 . 0.998 no
C5 . H51 . 1.043 no
O7 . H71 . 0.807 no
O8 . H81 . 0.885 no
N9 . C10 . 1.3891(16) yes
N9 . C16 . 1.3647(17) yes
C10 . O11 . 1.2469(17) yes
C10 . N12 . 1.3510(17) yes
N12 . C13 . 1.3377(18) yes
C13 . N14 . 1.3274(18) yes
C13 . C15 . 1.4388(18) yes
N14 . H141 . 0.856 no
N14 . H142 . 0.842 no
C15 . C16 . 1.3428(19) yes
C15 . C17 . 1.5209(17) yes
C16 . H161 . 0.915 no
C17 . C18 . 1.5251(19) yes
C17 . O20 . 1.4333(15) yes
C17 . H171 . 0.945 no
C18 . C19 . 1.523(2) yes
C18 . H182 . 0.984 no
C18 . H181 . 0.976 no
C19 . H191 . 0.955 no
C19 . H192 . 0.936 no
C19 . H193 . 0.957 no
O20 . H201 . 0.848 no
C21 . C22 . 1.5172(19) yes
C21 . O26 . 1.4160(16) yes
C21 . N29 . 1.4663(16) yes
C21 . H211 . 0.980 no
C22 . C23 . 1.5198(19) yes
C22 . H221 . 0.946 no
C22 . H222 . 0.958 no
C23 . C24 . 1.5419(19) yes
C23 . O27 . 1.4264(16) yes
C23 . H231 . 0.981 no
C24 . C25 . 1.514(2) yes
C24 . O26 . 1.4346(16) yes
C24 . H241 . 0.970 no
C25 . O28 . 1.421(2) yes
C25 . H252 . 0.976 no
C25 . H251 . 0.975 no
O27 . H271 . 0.860 no
O28 . H281 . 0.793 no
N29 . C30 . 1.3892(16) yes
N29 . C36 . 1.3790(17) yes
C30 . O31 . 1.2527(16) yes
C30 . N32 . 1.3384(17) yes
N32 . C33 . 1.3395(17) yes
C33 . N34 . 1.3193(18) yes
C33 . C35 . 1.4461(17) yes
N34 . H341 . 0.888 no
N34 . H342 . 0.851 no
C35 . C36 . 1.3414(19) yes
C35 . C37 . 1.5134(17) yes
C36 . H361 . 0.930 no
C37 . C38 . 1.520(2) yes
C37 . O40 . 1.4368(18) yes
C37 . H371 . 0.951 no
C38 . C39 . 1.504(3) yes
C38 . H382 . 0.967 no
C38 . H381 . 0.964 no
C39 . H392 . 0.967 no
C39 . H393 . 0.963 no
C39 . H391 . 0.975 no
O40 . H401 . 0.828 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . O6 . 106.74(10) yes
C2 . C1 . N9 . 112.81(10) yes
O6 . C1 . N9 . 108.99(10) yes
C2 . C1 . H11 . 113.6 no
O6 . C1 . H11 . 110.2 no
N9 . C1 . H11 . 104.5 no
C1 . C2 . C3 . 103.12(10) yes
C1 . C2 . H21 . 110.3 no
C3 . C2 . H21 . 113.4 no
C1 . C2 . H22 . 110.7 no
C3 . C2 . H22 . 111.7 no
H21 . C2 . H22 . 107.7 no
C2 . C3 . C4 . 102.03(10) yes
C2 . C3 . O7 . 112.64(11) yes
C4 . C3 . O7 . 109.17(11) yes
C2 . C3 . H31 . 111.1 no
C4 . C3 . H31 . 111.8 no
O7 . C3 . H31 . 110.0 no
C3 . C4 . C5 . 113.80(12) yes
C3 . C4 . O6 . 104.37(10) yes
C5 . C4 . O6 . 110.97(11) yes
C3 . C4 . H41 . 112.7 no
C5 . C4 . H41 . 108.0 no
O6 . C4 . H41 . 106.8 no
C4 . C5 . O8 . 109.18(13) yes
C4 . C5 . H52 . 108.0 no
O8 . C5 . H52 . 107.6 no
C4 . C5 . H51 . 122.0 no
O8 . C5 . H51 . 108.3 no
H52 . C5 . H51 . 100.7 no
C4 . O6 . C1 . 110.68(9) yes
C3 . O7 . H71 . 112.8 no
C5 . O8 . H81 . 114.1 no
C1 . N9 . C10 . 117.19(10) yes
C1 . N9 . C16 . 122.38(10) yes
C10 . N9 . C16 . 120.43(11) yes
N9 . C10 . O11 . 118.27(11) yes
N9 . C10 . N12 . 119.01(11) yes
O11 . C10 . N12 . 122.71(12) yes
C10 . N12 . C13 . 120.15(11) yes
N12 . C13 . N14 . 116.82(12) yes
N12 . C13 . C15 . 122.36(12) yes
N14 . C13 . C15 . 120.83(12) yes
C13 . N14 . H141 . 118.8 no
C13 . N14 . H142 . 120.5 no
H141 . N14 . H142 . 120.7 no
C13 . C15 . C16 . 115.58(11) yes
C13 . C15 . C17 . 121.48(11) yes
C16 . C15 . C17 . 122.86(11) yes
N9 . C16 . C15 . 122.31(11) yes
N9 . C16 . H161 . 117.9 no
C15 . C16 . H161 . 119.8 no
C15 . C17 . C18 . 112.53(11) yes
C15 . C17 . O20 . 110.52(10) yes
C18 . C17 . O20 . 107.96(10) yes
C15 . C17 . H171 . 107.9 no
C18 . C17 . H171 . 108.0 no
O20 . C17 . H171 . 109.8 no
C17 . C18 . C19 . 112.64(13) yes
C17 . C18 . H182 . 110.7 no
C19 . C18 . H182 . 109.8 no
C17 . C18 . H181 . 107.9 no
C19 . C18 . H181 . 109.3 no
H182 . C18 . H181 . 106.3 no
C18 . C19 . H191 . 110.5 no
C18 . C19 . H192 . 109.8 no
H191 . C19 . H192 . 107.8 no
C18 . C19 . H193 . 110.4 no
H191 . C19 . H193 . 106.1 no
H192 . C19 . H193 . 112.1 no
C17 . O20 . H201 . 109.1 no
C22 . C21 . O26 . 105.66(10) yes
C22 . C21 . N29 . 113.63(11) yes
O26 . C21 . N29 . 107.71(10) yes
C22 . C21 . H211 . 112.0 no
O26 . C21 . H211 . 109.7 no
N29 . C21 . H211 . 108.1 no
C21 . C22 . C23 . 103.93(11) yes
C21 . C22 . H221 . 111.1 no
C23 . C22 . H221 . 109.3 no
C21 . C22 . H222 . 109.4 no
C23 . C22 . H222 . 112.1 no
H221 . C22 . H222 . 110.8 no
C22 . C23 . C24 . 103.51(10) yes
C22 . C23 . O27 . 113.11(11) yes
C24 . C23 . O27 . 113.50(11) yes
C22 . C23 . H231 . 109.7 no
C24 . C23 . H231 . 111.2 no
O27 . C23 . H231 . 105.9 no
C23 . C24 . C25 . 113.62(12) yes
C23 . C24 . O26 . 107.24(10) yes
C25 . C24 . O26 . 108.57(12) yes
C23 . C24 . H241 . 111.1 no
C25 . C24 . H241 . 109.7 no
O26 . C24 . H241 . 106.3 no
C24 . C25 . O28 . 108.61(12) yes
C24 . C25 . H252 . 109.3 no
O28 . C25 . H252 . 109.9 no
C24 . C25 . H251 . 110.3 no
O28 . C25 . H251 . 111.3 no
H252 . C25 . H251 . 107.5 no
C24 . O26 . C21 . 109.98(10) yes
C23 . O27 . H271 . 109.5 no
C25 . O28 . H281 . 115.7 no
C21 . N29 . C30 . 120.02(10) yes
C21 . N29 . C36 . 120.04(10) yes
C30 . N29 . C36 . 119.90(10) yes
N29 . C30 . O31 . 119.14(11) yes
N29 . C30 . N32 . 119.14(11) yes
O31 . C30 . N32 . 121.72(11) yes
C30 . N32 . C33 . 121.14(11) yes
N32 . C33 . N34 . 116.65(12) yes
N32 . C33 . C35 . 121.51(11) yes
N34 . C33 . C35 . 121.84(12) yes
C33 . N34 . H341 . 119.9 no
C33 . N34 . H342 . 117.7 no
H341 . N34 . H342 . 119.7 no
C33 . C35 . C36 . 115.65(11) yes
C33 . C35 . C37 . 122.46(11) yes
C36 . C35 . C37 . 121.88(11) yes
N29 . C36 . C35 . 122.32(11) yes
N29 . C36 . H361 . 116.2 no
C35 . C36 . H361 . 121.5 no
C35 . C37 . C38 . 113.95(11) yes
C35 . C37 . O40 . 110.11(11) yes
C38 . C37 . O40 . 107.75(12) yes
C35 . C37 . H371 . 109.0 no
C38 . C37 . H371 . 106.5 no
O40 . C37 . H371 . 109.4 no
C37 . C38 . C39 . 112.44(15) yes
C37 . C38 . H382 . 108.8 no
C39 . C38 . H382 . 108.5 no
C37 . C38 . H381 . 108.3 no
C39 . C38 . H381 . 109.5 no
H382 . C38 . H381 . 109.2 no
C38 . C39 . H392 . 110.8 no
C38 . C39 . H393 . 111.8 no
H392 . C39 . H393 . 108.6 no
C38 . C39 . H391 . 111.5 no
H392 . C39 . H391 . 106.7 no
H393 . C39 . H391 . 107.2 no
C37 . O40 . H401 . 101.0 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N14 . H141 . O7 1_554 135.77(4) 0.856 2.285 2.959(2) yes
N14 . H142 . N32 1_454 161.67(5) 0.842 2.111 2.923(2) yes
C2 . H21 . O31 1_455 125.65(4) 0.948 2.564 3.210(2) yes
C2 . H22 . O26 . 175.91(4) 0.960 2.375 3.333(2) yes
O7 . H71 . O31 1_455 174.84(4) 0.807 1.908 2.713(2) yes
O8 . H81 . C30 . 144.52(4) 0.885 2.542 3.302(2) yes
O8 . H81 . O31 . 160.94(5) 0.885 1.893 2.745(2) yes
C17 . H171 . O40 1_564 172.69(4) 0.945 2.583 3.522(2) yes
O20 . H201 . C23 1_565 145.62(4) 0.848 2.505 3.241(2) yes
O20 . H201 . O27 1_565 179.04(4) 0.848 1.959 2.806(2) yes
O28 . H281 . O20 1_445 147.69(4) 0.793 2.128 2.830(2) yes
N34 . H341 . N12 1_656 175.69(5) 0.888 2.142 3.029(2) yes
N34 . H342 . O40 . 130.82(4) 0.851 2.279 2.908(2) yes
O40 . H401 . O7 1_545 163.32(4) 0.828 2.002 2.805(2) yes
C37 . H371 . O8 1_445 126.80(4) 0.951 2.579 3.239(2) yes
C21 . H211 . O11 1_655 135.11(4) 0.980 2.432 3.201(2) yes
C22 . H221 . O6 1_545 162.73(4) 0.946 2.393 3.309(2) yes
O27 . H271 . O11 1_655 176.51(4) 0.860 1.832 2.691(2) yes


