# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_Rd-1312-I
_database_code_depnum_ccdc_archive 'CCDC 2476564'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-06-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT094_Rd-1312-I           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.49 Report
RESPONSE: The crystal contains minor components, the orientation of 
which has not been established.
;
_vrf_PLAT097_Rd-1312-I           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.73 eA-3  
RESPONSE: The crystal contains minor components, the orientation of 
which has not been established.
;
_vrf_PLAT340_Rd-1312-I           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0064 Ang.  
RESPONSE: The crystal was small and of poor quality.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O7'
_chemical_formula_sum            'C16 H19 N O7'
_chemical_formula_weight         337.32
_chemical_absolute_configuration unknown
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 N1 O5'
_chemical_oxdiff_usercomment     Rd-1312-I
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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.4118(6)
_cell_length_b                   8.0417(2)
_cell_length_c                   26.1942(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3246.43(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4253
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      77.0990
_cell_measurement_theta_min      5.7220
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.91a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0138
-1 0 -1 0.0102
0 0 1 0.0196
0 0 -1 0.0042
0 1 0 0.1811
0 -1 0 0.1717
-1 0 1 0.0157
1 0 -1 0.0078

_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9986 -0.0017 0.9950 0.0304 -0.1081 -0.0280
-0.9986 0.0017 -0.9950 -0.0304 0.1081 0.0280
0.0006 -0.0011 1.0004 -0.0363 -0.0340 -0.0315
-0.0006 0.0011 -1.0004 0.0363 0.0340 0.0315
0.0044 0.9994 0.0081 -0.0797 -0.0644 0.1617
-0.0044 -0.9994 -0.0081 0.0797 0.0644 -0.1617
-0.9974 -0.0005 1.0058 -0.1030 0.0401 -0.0350
0.9974 0.0005 -1.0058 0.1030 -0.0401 0.0350

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23073
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.807
_diffrn_reflns_theta_min         5.742
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.40 -63.00   0.60   16.00    --  -48.70-140.00 -77.00   94
  2  ω     92.00 117.20   0.60   16.00    --   48.70  43.00 114.00   42
  3  ω     47.00  73.40   0.60   16.00    --   48.70  43.00 114.00   44
  4  ω    -48.00 -22.80   0.60   35.00    --  -86.25  43.00 114.00   42
  5  ω    -71.00 -44.60   0.60   35.00    --  -86.25  78.00 -74.00   44
  6  ω     67.00  98.20   0.60   35.00    --  107.75-140.00 -77.00   52
  7  ω    100.00 148.00   0.60   35.00    --  107.75  43.00 114.00   80
  8  ω     72.00  99.00   0.60   35.00    --  107.75-130.00  96.00   45
  9  ω   -118.00 -75.40   0.60   16.00    --  -48.70-125.00  30.00   71
 10  ω    -22.00   5.00   0.60   16.00    --  -48.70  19.00-150.00   45
 11  ω   -118.00 -73.60   0.60   16.00    --  -48.70-125.00 120.00   74
 12  ω     49.00 100.00   0.60   35.00    --  107.75-125.00-180.00   85
 13  ω     74.00 104.00   0.60   35.00    --  107.75 -77.00 -30.00   50
 14  ω     73.00 104.20   0.60   35.00    --  107.75 -97.00 143.07   52
 15  ω     40.00  66.40   0.60   35.00    --  107.75 -77.00 -30.00   44
 16  ω     54.00  80.40   0.60   35.00    --  107.75-120.00 -60.68   44
 17  ω     94.00 123.40   0.60   35.00    --  107.75 -87.00 179.99   49
 18  ω     96.00 150.60   0.60   35.00    --  107.75 125.00   0.00   91
 19  ω     50.00  83.60   0.60   35.00    --  107.75 -77.00  30.00   56
 20  ω     44.00  70.40   0.60   35.00    --  107.75-108.00-153.29   44
 21  ω     72.00 105.00   0.60   35.00    --  107.75-108.00-153.29   55
 22  ω     37.00  62.20   0.60   35.00    --  107.75 -61.00-150.00   42
 23  ω     98.00 170.60   0.60   35.00    --  107.75  15.00 -90.00  121
 24  ω     37.00  66.40   0.60   35.00    --  107.75 -61.00 -30.00   49
 25  ω     36.00  61.20   0.60   35.00    --  107.75 -61.00  60.00   42
 26  ω     37.00  63.40   0.60   35.00    --  107.75 -87.00 179.99   44
 27  ω     40.00  68.20   0.60   35.00    --  107.75 -61.00   0.00   47
 28  ω     36.00  65.40   0.60   35.00    --  107.75   0.00  60.00   49
 29  ω    107.00 140.00   0.60   35.00    --  107.75   0.00  60.00   55
 30  ω     45.00  83.40   0.60   35.00    --  107.75 -77.00-120.00   64
 31  ω     37.00  63.40   0.60   35.00    --  107.75 -95.00  90.00   44
 32  ω     59.00  95.00   0.60   35.00    --  107.75 -95.00 -30.00   60
 33  ω    101.00 140.60   0.60   35.00    --  107.75  45.00   0.00   66
 34  ω     89.00 114.20   0.60   35.00    --  107.75  77.00 -79.84   42
 35  ω    147.00 173.40   0.60   35.00    --  107.75  77.00 -79.84   44
 36  ω     42.00  68.40   0.60   35.00    --  107.75 -78.00 160.00   44
;
_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      0.0665545000
_diffrn_orient_matrix_UB_12      -0.0797913000
_diffrn_orient_matrix_UB_13      -0.0364179000
_diffrn_orient_matrix_UB_21      -0.0744812000
_diffrn_orient_matrix_UB_22      -0.0638093000
_diffrn_orient_matrix_UB_23      -0.0339975000
_diffrn_orient_matrix_UB_31      0.0034325000
_diffrn_orient_matrix_UB_32      0.1620387000
_diffrn_orient_matrix_UB_33      -0.0312774000
_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         0.775
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                5514
_reflns_number_total             6205
_reflns_odcompleteness_completeness 92.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_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 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.91a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 
;
 Flack x determined using 2115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1309P)²+1.1105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1812
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20A(H20A,H20B), C13A(H13A,H13B), C7B(H7C,H7D), C7A(H7A,H7B), C13B(H13C,H13D),
  C20B(H20C,H20D)
2.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C5B(H5B), C2A(H2A), C6B(H6B), C3A(H3A), C2B(H2B), C3B(H3B)
2.c Idealised Me refined as rotating group:
 C15B(H15D,H15E,H15F), C16A(H16A,H16B,H16C), C16B(H16D,H16E,H16F), C21B(H21D,
 H21E,H21F), C15A(H15A,H15B,H15C), C21A(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O19A O 0.5526(2) 0.3591(3) 0.58728(12) 0.0270(6) Uani 1 1 d . . . . .
O14B O 0.7093(2) 0.8663(4) 0.39276(12) 0.0250(6) Uani 1 1 d . . . . .
O11A O 0.4376(2) 0.7863(5) 0.52385(13) 0.0309(7) Uani 1 1 d . . . . .
O10B O 0.7753(2) 0.7336(4) 0.45712(14) 0.0288(8) Uani 1 1 d . . . . .
O19B O 0.8014(2) 0.3682(4) 0.41288(13) 0.0280(7) Uani 1 1 d . . . . .
O10A O 0.5212(2) 0.7143(4) 0.54101(15) 0.0327(8) Uani 1 1 d . . . . .
O14A O 0.4622(2) 0.8572(4) 0.60530(13) 0.0282(7) Uani 1 1 d . . . . .
O18B O 0.6756(2) 0.3586(4) 0.45521(15) 0.0381(8) Uani 1 1 d . . . . .
O18A O 0.4222(2) 0.3432(4) 0.54927(14) 0.0344(8) Uani 1 1 d . . . . .
O11B O 0.6923(2) 0.8062(4) 0.47583(14) 0.0323(7) Uani 1 1 d . . . . .
O2B O 0.4981(3) -0.1532(4) 0.29252(15) 0.0407(8) Uani 1 1 d . . . . .
O3A O 0.2519(3) -0.1581(4) 0.70802(16) 0.0423(9) Uani 1 1 d . . . . .
O3B O 0.4061(3) 0.0170(5) 0.2589(2) 0.0569(12) Uani 1 1 d . . . . .
C5A C 0.3686(3) 0.0908(6) 0.68963(19) 0.0295(10) Uani 1 1 d . . . . .
H5A H 0.389061 -0.019963 0.686002 0.035 Uiso 1 1 calc R U . . .
N1A N 0.2281(3) -0.0169(5) 0.71966(17) 0.0358(9) Uani 1 1 d . . . . .
C1A C 0.3919(3) 0.3862(6) 0.68248(16) 0.0255(9) Uani 1 1 d . . . . .
C6A C 0.4213(3) 0.2240(6) 0.67776(19) 0.0280(10) Uani 1 1 d . . . . .
H6A H 0.478821 0.204193 0.666165 0.034 Uiso 1 1 calc R U . . .
N1B N 0.4745(3) -0.0138(5) 0.28091(17) 0.0353(9) Uani 1 1 d . . . . .
O2A O 0.1603(3) 0.0120(6) 0.7411(2) 0.0589(12) Uani 1 1 d . . . . .
C9B C 0.7618(3) 0.7252(5) 0.40277(19) 0.0251(9) Uani 1 1 d . . . . .
C15B C 0.8486(3) 0.7333(6) 0.3766(2) 0.0315(11) Uani 1 1 d . . . . .
H15D H 0.840225 0.732479 0.339546 0.047 Uiso 1 1 calc R U . . .
H15E H 0.883650 0.637021 0.386672 0.047 Uiso 1 1 calc R U . . .
H15F H 0.878554 0.835786 0.386643 0.047 Uiso 1 1 calc R U . . .
C4A C 0.2855(3) 0.1216(6) 0.70688(17) 0.0268(9) Uani 1 1 d . . . . .
C5B C 0.4989(3) 0.2874(6) 0.28874(19) 0.0280(9) Uani 1 1 d . . . . .
H5B H 0.442135 0.306803 0.275880 0.034 Uiso 1 1 calc R U . . .
C2A C 0.3080(3) 0.4136(5) 0.70025(17) 0.0278(10) Uani 1 1 d . . . . .
H2A H 0.287547 0.524281 0.704136 0.033 Uiso 1 1 calc R U . . .
C20A C 0.5789(3) 0.2144(6) 0.5573(2) 0.0319(10) Uani 1 1 d . . . . .
H20A H 0.574775 0.239129 0.520379 0.038 Uiso 1 1 calc R U . . .
H20B H 0.540892 0.118389 0.565037 0.038 Uiso 1 1 calc R U . . .
C8B C 0.6987(3) 0.5768(5) 0.39206(17) 0.0232(8) Uani 1 1 d . . . . .
C17A C 0.4717(3) 0.4131(5) 0.57815(17) 0.0259(8) Uani 1 1 d . . . . .
C13A C 0.3625(3) 0.6460(5) 0.59139(19) 0.0277(9) Uani 1 1 d . . . . .
H13A H 0.334894 0.579118 0.564106 0.033 Uiso 1 1 calc R U . . .
H13B H 0.321453 0.658248 0.620241 0.033 Uiso 1 1 calc R U . . .
C4B C 0.5305(3) 0.1283(6) 0.29467(18) 0.0281(9) Uani 1 1 d . . . . .
C12B C 0.6432(3) 0.8238(5) 0.42912(18) 0.0247(8) Uani 1 1 d . . . . .
C8A C 0.4498(3) 0.5684(5) 0.60893(18) 0.0255(9) Uani 1 1 d . . . . .
C6B C 0.5533(3) 0.4191(5) 0.30234(18) 0.0274(10) Uani 1 1 d . . . . .
H6B H 0.533018 0.530168 0.299161 0.033 Uiso 1 1 calc R U . . .
C3A C 0.2540(3) 0.2823(6) 0.7123(2) 0.0300(10) Uani 1 1 d . . . . .
H3A H 0.196619 0.301647 0.724083 0.036 Uiso 1 1 calc R U . . .
C7B C 0.6969(3) 0.5326(5) 0.33465(17) 0.0271(9) Uani 1 1 d . . . . .
H7C H 0.679507 0.632836 0.315239 0.032 Uiso 1 1 calc R U . . .
H7D H 0.756454 0.502819 0.323834 0.032 Uiso 1 1 calc R U . . .
C1B C 0.6361(3) 0.3903(5) 0.32030(17) 0.0234(9) Uani 1 1 d . . . . .
C2B C 0.6659(3) 0.2282(6) 0.3251(2) 0.0277(10) Uani 1 1 d . . . . .
H2B H 0.723104 0.208909 0.337285 0.033 Uiso 1 1 calc R U . . .
C7A C 0.4516(3) 0.5278(5) 0.66688(17) 0.0264(9) Uani 1 1 d . . . . .
H7A H 0.511793 0.498842 0.676710 0.032 Uiso 1 1 calc R U . . .
H7B H 0.435033 0.628874 0.686142 0.032 Uiso 1 1 calc R U . . .
C17B C 0.7219(3) 0.4232(5) 0.42453(17) 0.0261(9) Uani 1 1 d . . . . .
C13B C 0.6123(3) 0.6539(5) 0.41145(18) 0.0269(9) Uani 1 1 d . . . . .
H13C H 0.568970 0.663111 0.383693 0.032 Uiso 1 1 calc R U . . .
H13D H 0.587378 0.588739 0.439962 0.032 Uiso 1 1 calc R U . . .
C12A C 0.3926(3) 0.8137(6) 0.57161(18) 0.0269(9) Uani 1 1 d . . . . .
C9A C 0.5125(3) 0.7142(6) 0.59573(19) 0.0270(9) Uani 1 1 d . . . . .
C16A C 0.3286(3) 0.9508(6) 0.5645(2) 0.0325(10) Uani 1 1 d . . . . .
H16A H 0.359127 1.052121 0.553976 0.049 Uiso 1 1 calc R U . . .
H16B H 0.298067 0.971092 0.596674 0.049 Uiso 1 1 calc R U . . .
H16C H 0.286704 0.919256 0.538069 0.049 Uiso 1 1 calc R U . . .
C3B C 0.6137(3) 0.0942(5) 0.31255(18) 0.0279(10) Uani 1 1 d . . . . .
H3B H 0.633885 -0.016879 0.315987 0.033 Uiso 1 1 calc R U . . .
C16B C 0.5784(3) 0.9589(6) 0.43653(19) 0.0301(9) Uani 1 1 d . . . . .
H16D H 0.608589 1.063536 0.443785 0.045 Uiso 1 1 calc R U . . .
H16E H 0.540327 0.930851 0.465237 0.045 Uiso 1 1 calc R U . . .
H16F H 0.543584 0.971383 0.405453 0.045 Uiso 1 1 calc R U . . .
C21B C 0.9185(3) 0.1764(7) 0.4251(3) 0.0425(12) Uani 1 1 d . . . . .
H21D H 0.919242 0.162377 0.387973 0.064 Uiso 1 1 calc R U . . .
H21E H 0.935728 0.071865 0.441512 0.064 Uiso 1 1 calc R U . . .
H21F H 0.959206 0.264495 0.434844 0.064 Uiso 1 1 calc R U . . .
C20B C 0.8292(3) 0.2225(6) 0.4420(2) 0.0299(10) Uani 1 1 d . . . . .
H20C H 0.788876 0.128772 0.435966 0.036 Uiso 1 1 calc R U . . .
H20D H 0.829178 0.248284 0.478969 0.036 Uiso 1 1 calc R U . . .
C15A C 0.6013(3) 0.7243(7) 0.6188(3) 0.0358(12) Uani 1 1 d . . . . .
H15A H 0.632344 0.619886 0.612590 0.054 Uiso 1 1 calc R U . . .
H15B H 0.596268 0.743051 0.655628 0.054 Uiso 1 1 calc R U . . .
H15C H 0.633301 0.816516 0.603195 0.054 Uiso 1 1 calc R U . . .
C21A C 0.6714(3) 0.1755(6) 0.5717(2) 0.0371(11) Uani 1 1 d . . . . .
H21A H 0.693855 0.088057 0.549266 0.056 Uiso 1 1 calc R U . . .
H21B H 0.673462 0.137433 0.607221 0.056 Uiso 1 1 calc R U . . .
H21C H 0.706929 0.275828 0.567983 0.056 Uiso 1 1 calc R U . . .


_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
O19A C20A 1.461(6) . ?
O19A C17A 1.341(5) . ?
O14B C9B 1.418(5) . ?
O14B C12B 1.436(5) . ?
O11A O10A 1.482(5) . ?
O11A C12A 1.447(6) . ?
O10B O11B 1.489(5) . ?
O10B C9B 1.440(6) . ?
O19B C17B 1.337(5) . ?
O19B C20B 1.462(5) . ?
O10A C9A 1.440(6) . ?
O14A C12A 1.432(5) . ?
O14A C9A 1.409(6) . ?
O18B C17B 1.194(6) . ?
O18A C17A 1.212(6) . ?
O11B C12B 1.446(6) . ?
O2B N1B 1.217(6) . ?
O3A N1A 1.231(6) . ?
O3B N1B 1.226(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.380(7) . ?
C5A C4A 1.380(7) . ?
N1A O2A 1.210(6) . ?
N1A C4A 1.460(6) . ?
C1A C6A 1.387(7) . ?
C1A C2A 1.391(6) . ?
C1A C7A 1.521(6) . ?
C6A H6A 0.9500 . ?
N1B C4B 1.477(6) . ?
C9B C15B 1.504(7) . ?
C9B C8B 1.565(6) . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C4A C3A 1.388(7) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.378(7) . ?
C5B C6B 1.398(7) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.380(7) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C20A C21A 1.507(7) . ?
C8B C7B 1.545(6) . ?
C8B C17B 1.542(6) . ?
C8B C13B 1.554(6) . ?
C17A C8A 1.525(6) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13A C8A 1.553(6) . ?
C13A C12A 1.518(6) . ?
C4B C3B 1.392(7) . ?
C12B C13B 1.519(6) . ?
C12B C16B 1.488(6) . ?
C8A C7A 1.553(6) . ?
C8A C9A 1.558(6) . ?
C6B H6B 0.9500 . ?
C6B C1B 1.379(7) . ?
C3A H3A 0.9500 . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C7B C1B 1.526(6) . ?
C1B C2B 1.388(6) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.385(7) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C12A C16A 1.491(6) . ?
C9A C15A 1.498(7) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C3B H3B 0.9500 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C21B C20B 1.492(7) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?

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
C17A O19A C20A 114.8(4) . . ?
C9B O14B C12B 95.3(3) . . ?
C12A O11A O10A 102.3(3) . . ?
C9B O10B O11B 102.7(3) . . ?
C17B O19B C20B 114.5(4) . . ?
C9A O10A O11A 102.8(3) . . ?
C9A O14A C12A 95.9(3) . . ?
C12B O11B O10B 102.1(3) . . ?
C6A C5A H5A 120.6 . . ?
C6A C5A C4A 118.8(4) . . ?
C4A C5A H5A 120.6 . . ?
O3A N1A C4A 117.8(4) . . ?
O2A N1A O3A 123.3(4) . . ?
O2A N1A C4A 118.9(4) . . ?
C6A C1A C2A 118.9(4) . . ?
C6A C1A C7A 118.8(4) . . ?
C2A C1A C7A 122.3(4) . . ?
C5A C6A C1A 121.1(5) . . ?
C5A C6A H6A 119.4 . . ?
C1A C6A H6A 119.4 . . ?
O2B N1B O3B 124.1(4) . . ?
O2B N1B C4B 118.5(4) . . ?
O3B N1B C4B 117.4(4) . . ?
O14B C9B O10B 103.2(4) . . ?
O14B C9B C15B 112.9(4) . . ?
O14B C9B C8B 102.8(3) . . ?
O10B C9B C15B 108.6(4) . . ?
O10B C9B C8B 107.6(4) . . ?
C15B C9B C8B 120.3(4) . . ?
C9B C15B H15D 109.5 . . ?
C9B C15B H15E 109.5 . . ?
C9B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C5A C4A N1A 120.0(4) . . ?
C5A C4A C3A 121.6(4) . . ?
C3A C4A N1A 118.4(4) . . ?
C4B C5B H5B 121.2 . . ?
C4B C5B C6B 117.6(4) . . ?
C6B C5B H5B 121.2 . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A C1A 121.0(4) . . ?
C3A C2A H2A 119.5 . . ?
O19A C20A H20A 110.3 . . ?
O19A C20A H20B 110.3 . . ?
O19A C20A C21A 107.1(4) . . ?
H20A C20A H20B 108.6 . . ?
C21A C20A H20A 110.3 . . ?
C21A C20A H20B 110.3 . . ?
C7B C8B C9B 111.2(4) . . ?
C7B C8B C13B 113.2(4) . . ?
C17B C8B C9B 111.6(3) . . ?
C17B C8B C7B 110.9(3) . . ?
C17B C8B C13B 109.8(4) . . ?
C13B C8B C9B 99.8(3) . . ?
O19A C17A C8A 112.1(4) . . ?
O18A C17A O19A 123.1(4) . . ?
O18A C17A C8A 124.8(4) . . ?
H13A C13A H13B 109.4 . . ?
C8A C13A H13A 111.6 . . ?
C8A C13A H13B 111.6 . . ?
C12A C13A H13A 111.6 . . ?
C12A C13A H13B 111.6 . . ?
C12A C13A C8A 101.1(3) . . ?
C5B C4B N1B 118.9(4) . . ?
C5B C4B C3B 123.1(4) . . ?
C3B C4B N1B 117.9(4) . . ?
O14B C12B O11B 102.3(3) . . ?
O14B C12B C13B 103.5(3) . . ?
O14B C12B C16B 112.9(4) . . ?
O11B C12B C13B 109.5(4) . . ?
O11B C12B C16B 108.2(4) . . ?
C16B C12B C13B 119.1(4) . . ?
C17A C8A C13A 111.4(4) . . ?
C17A C8A C7A 109.9(4) . . ?
C17A C8A C9A 111.2(4) . . ?
C13A C8A C9A 99.8(3) . . ?
C7A C8A C13A 112.9(4) . . ?
C7A C8A C9A 111.3(4) . . ?
C5B C6B H6B 119.5 . . ?
C1B C6B C5B 121.0(4) . . ?
C1B C6B H6B 119.5 . . ?
C4A C3A H3A 120.7 . . ?
C2A C3A C4A 118.6(4) . . ?
C2A C3A H3A 120.7 . . ?
C8B C7B H7C 108.5 . . ?
C8B C7B H7D 108.5 . . ?
H7C C7B H7D 107.5 . . ?
C1B C7B C8B 115.0(4) . . ?
C1B C7B H7C 108.5 . . ?
C1B C7B H7D 108.5 . . ?
C6B C1B C7B 121.7(4) . . ?
C6B C1B C2B 119.7(4) . . ?
C2B C1B C7B 118.6(4) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B C1B 121.1(4) . . ?
C3B C2B H2B 119.4 . . ?
C1A C7A C8A 114.1(4) . . ?
C1A C7A H7A 108.7 . . ?
C1A C7A H7B 108.7 . . ?
C8A C7A H7A 108.7 . . ?
C8A C7A H7B 108.7 . . ?
H7A C7A H7B 107.6 . . ?
O19B C17B C8B 110.6(4) . . ?
O18B C17B O19B 123.9(4) . . ?
O18B C17B C8B 125.5(4) . . ?
C8B C13B H13C 111.6 . . ?
C8B C13B H13D 111.6 . . ?
C12B C13B C8B 101.0(3) . . ?
C12B C13B H13C 111.6 . . ?
C12B C13B H13D 111.6 . . ?
H13C C13B H13D 109.4 . . ?
O11A C12A C13A 107.9(4) . . ?
O11A C12A C16A 108.7(4) . . ?
O14A C12A O11A 102.2(3) . . ?
O14A C12A C13A 103.7(4) . . ?
O14A C12A C16A 113.1(4) . . ?
C16A C12A C13A 119.8(4) . . ?
O10A C9A C8A 106.2(4) . . ?
O10A C9A C15A 108.4(4) . . ?
O14A C9A O10A 103.2(4) . . ?
O14A C9A C8A 103.5(4) . . ?
O14A C9A C15A 112.7(4) . . ?
C15A C9A C8A 121.2(4) . . ?
C12A C16A H16A 109.5 . . ?
C12A C16A H16B 109.5 . . ?
C12A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C4B C3B H3B 121.2 . . ?
C2B C3B C4B 117.5(4) . . ?
C2B C3B H3B 121.2 . . ?
C12B C16B H16D 109.5 . . ?
C12B C16B H16E 109.5 . . ?
C12B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
O19B C20B C21B 108.4(4) . . ?
O19B C20B H20C 110.0 . . ?
O19B C20B H20D 110.0 . . ?
C21B C20B H20C 110.0 . . ?
C21B C20B H20D 110.0 . . ?
H20C C20B H20D 108.4 . . ?
C9A C15A H15A 109.5 . . ?
C9A C15A H15B 109.5 . . ?
C9A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?

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
O19A C17A C8A C13A 170.5(4) . . . . ?
O19A C17A C8A C7A -63.6(5) . . . . ?
O19A C17A C8A C9A 60.2(5) . . . . ?
O14B C9B C8B C7B 84.5(4) . . . . ?
O14B C9B C8B C17B -151.1(3) . . . . ?
O14B C9B C8B C13B -35.2(4) . . . . ?
O14B C12B C13B C8B 35.8(4) . . . . ?
O11A O10A C9A O14A -33.3(4) . . . . ?
O11A O10A C9A C8A 75.2(4) . . . . ?
O11A O10A C9A C15A -153.1(3) . . . . ?
O10B O11B C12B O14B -35.3(4) . . . . ?
O10B O11B C12B C13B 74.0(4) . . . . ?
O10B O11B C12B C16B -154.7(3) . . . . ?
O10B C9B C8B C7B -166.9(4) . . . . ?
O10B C9B C8B C17B -42.6(5) . . . . ?
O10B C9B C8B C13B 73.3(4) . . . . ?
O10A O11A C12A O14A 34.5(4) . . . . ?
O10A O11A C12A C13A -74.4(4) . . . . ?
O10A O11A C12A C16A 154.2(3) . . . . ?
O18A C17A C8A C13A -10.7(6) . . . . ?
O18A C17A C8A C7A 115.3(5) . . . . ?
O18A C17A C8A C9A -121.0(5) . . . . ?
O11B O10B C9B O14B 33.4(4) . . . . ?
O11B O10B C9B C15B 153.4(3) . . . . ?
O11B O10B C9B C8B -74.9(4) . . . . ?
O11B C12B C13B C8B -72.7(4) . . . . ?
O2B N1B C4B C5B -170.3(4) . . . . ?
O2B N1B C4B C3B 10.4(7) . . . . ?
O3A N1A C4A C5A -9.7(7) . . . . ?
O3A N1A C4A C3A 170.0(4) . . . . ?
O3B N1B C4B C5B 8.8(7) . . . . ?
O3B N1B C4B C3B -170.5(5) . . . . ?
C5A C4A C3A C2A -0.3(7) . . . . ?
N1A C4A C3A C2A -180.0(4) . . . . ?
C1A C2A C3A C4A 0.7(7) . . . . ?
C6A C5A C4A N1A 179.9(5) . . . . ?
C6A C5A C4A C3A 0.2(7) . . . . ?
C6A C1A C2A C3A -1.0(7) . . . . ?
C6A C1A C7A C8A 84.2(5) . . . . ?
N1B C4B C3B C2B 179.7(4) . . . . ?
O2A N1A C4A C5A 170.1(5) . . . . ?
O2A N1A C4A C3A -10.2(7) . . . . ?
C9B O14B C12B O11B 55.3(4) . . . . ?
C9B O14B C12B C13B -58.5(4) . . . . ?
C9B O14B C12B C16B 171.4(4) . . . . ?
C9B O10B O11B C12B 1.5(4) . . . . ?
C9B C8B C7B C1B -179.2(4) . . . . ?
C9B C8B C17B O19B -62.2(5) . . . . ?
C9B C8B C17B O18B 119.2(5) . . . . ?
C9B C8B C13B C12B -0.6(4) . . . . ?
C15B C9B C8B C7B -42.0(5) . . . . ?
C15B C9B C8B C17B 82.4(5) . . . . ?
C15B C9B C8B C13B -161.7(4) . . . . ?
C4A C5A C6A C1A -0.6(8) . . . . ?
C5B C4B C3B C2B 0.5(7) . . . . ?
C5B C6B C1B C7B 179.2(5) . . . . ?
C5B C6B C1B C2B -0.2(7) . . . . ?
C2A C1A C6A C5A 1.0(7) . . . . ?
C2A C1A C7A C8A -94.3(5) . . . . ?
C20A O19A C17A O18A 3.6(6) . . . . ?
C20A O19A C17A C8A -177.6(4) . . . . ?
C8B C7B C1B C6B 96.5(5) . . . . ?
C8B C7B C1B C2B -84.1(5) . . . . ?
C17A O19A C20A C21A 178.5(4) . . . . ?
C17A C8A C7A C1A -56.3(5) . . . . ?
C17A C8A C9A O10A 43.6(5) . . . . ?
C17A C8A C9A O14A 151.9(4) . . . . ?
C17A C8A C9A C15A -80.5(6) . . . . ?
C13A C8A C7A C1A 68.8(5) . . . . ?
C13A C8A C9A O10A -74.0(4) . . . . ?
C13A C8A C9A O14A 34.3(4) . . . . ?
C13A C8A C9A C15A 161.9(5) . . . . ?
C4B C5B C6B C1B 0.9(7) . . . . ?
C12B O14B C9B O10B -54.5(4) . . . . ?
C12B O14B C9B C15B -171.6(4) . . . . ?
C12B O14B C9B C8B 57.3(4) . . . . ?
C8A C13A C12A O11A 72.6(4) . . . . ?
C8A C13A C12A O14A -35.3(4) . . . . ?
C8A C13A C12A C16A -162.4(4) . . . . ?
C6B C5B C4B N1B 179.7(4) . . . . ?
C6B C5B C4B C3B -1.1(7) . . . . ?
C6B C1B C2B C3B -0.5(8) . . . . ?
C7B C8B C17B O19B 62.3(5) . . . . ?
C7B C8B C17B O18B -116.3(5) . . . . ?
C7B C8B C13B C12B -118.8(4) . . . . ?
C7B C1B C2B C3B -179.8(4) . . . . ?
C1B C2B C3B C4B 0.3(8) . . . . ?
C7A C1A C6A C5A -177.6(4) . . . . ?
C7A C1A C2A C3A 177.5(4) . . . . ?
C7A C8A C9A O10A 166.6(3) . . . . ?
C7A C8A C9A O14A -85.1(4) . . . . ?
C7A C8A C9A C15A 42.5(6) . . . . ?
C17B O19B C20B C21B -179.8(4) . . . . ?
C17B C8B C7B C1B 56.0(5) . . . . ?
C17B C8B C13B C12B 116.7(4) . . . . ?
C13B C8B C7B C1B -67.9(5) . . . . ?
C13B C8B C17B O19B -171.9(3) . . . . ?
C13B C8B C17B O18B 9.6(6) . . . . ?
C12A O11A O10A C9A -1.1(4) . . . . ?
C12A O14A C9A O10A 54.2(4) . . . . ?
C12A O14A C9A C8A -56.4(4) . . . . ?
C12A O14A C9A C15A 170.9(4) . . . . ?
C12A C13A C8A C17A -116.6(4) . . . . ?
C12A C13A C8A C7A 119.1(4) . . . . ?
C12A C13A C8A C9A 0.9(4) . . . . ?
C9A O14A C12A O11A -54.6(4) . . . . ?
C9A O14A C12A C13A 57.4(4) . . . . ?
C9A O14A C12A C16A -171.3(4) . . . . ?
C9A C8A C7A C1A -179.9(4) . . . . ?
C16B C12B C13B C8B 162.1(4) . . . . ?
C20B O19B C17B O18B -1.6(6) . . . . ?
C20B O19B C17B C8B 179.8(4) . . . . ?

_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.712
####################################################################### 
# 
# 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_Rd-1326-rhombic
_database_code_depnum_ccdc_archive 'CCDC 2476566'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N O10'
_chemical_formula_sum            'C16 H21 N O10'
_chemical_formula_weight         387.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19NO8
_chemical_oxdiff_usercomment     Rd-1326
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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_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'

_cell_length_a                   6.27451(5)
_cell_length_b                   8.24052(7)
_cell_length_c                   33.9220(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3352(7)
_cell_angle_gamma                90
_cell_volume                     1752.49(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16568
_cell_measurement_temperature    99.96(13)
_cell_measurement_theta_max      77.5650
_cell_measurement_theta_min      2.5910
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0229
0 1 0 0.0210
0 0 1 0.0554
0 0 -1 0.0420
1 -1 -21 0.0401
1 0 -1 0.1245
-1 0 1 0.0572
2 0 18 0.0460

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0004 -0.9993 -0.0008 -0.1740 0.0653 0.0189
0.0004 0.9993 0.0008 0.1740 -0.0653 -0.0189
0.0000 0.0000 0.9999 0.0163 0.0422 0.0046
-0.0000 -0.0000 -0.9999 -0.0163 -0.0422 -0.0046
0.6755 -1.0448 -21.4147 -0.5195 -0.8502 0.0858
0.9997 -0.0001 -0.9995 0.0016 -0.0650 0.2393
-0.9997 0.0001 0.9995 -0.0016 0.0650 -0.2393
2.1680 0.0169 18.1458 0.3382 0.7145 0.6124

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            21207
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.807
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -26.00   0.50    0.40    --  -48.70 151.00-178.00  156
  2  ω    -85.00 -11.00   0.50    0.40    --  -48.70 122.00  20.00  148
  3  ω   -119.00 -56.00   0.50    0.40    --  -48.70-151.00 137.00  126
  4  ω     74.00 100.00   0.50    0.40    --   48.70-151.00 137.00   52
  5  ω     59.00  91.00   0.50    0.40    --   48.70-122.00 -61.00   64
  6  ω   -120.00 -76.00   0.50    1.60    --  -86.25-122.00 -61.00   88
  7  ω   -126.00-101.00   0.50    1.60    --  -86.25-151.00 137.00   50
  8  ω    -89.00 -64.00   0.50    1.60    --  -86.25 151.00-178.00   50
  9  ω    113.00 138.00   0.50    1.60    --  107.75 122.00  20.00   50
 10  ω     85.00 110.00   0.50    1.60    --  107.75-122.00 -61.00   50
 11  ω     42.00  81.00   0.50    1.60    --  107.75-122.00 -61.00   78
 12  ω    102.00 130.00   0.50    1.60    --  107.75-151.00 137.00   56
 13  ω    104.00 130.00   0.50    1.60    --  107.75 151.00-178.00   52
 14  ω    -25.00  26.00   0.50    0.40    --  -48.70  19.00  30.00  102
 15  ω    -23.00  26.00   0.50    0.40    --  -48.70  19.00-150.00   98
 16  ω   -115.00 -39.00   0.50    0.40    --  -48.70 -77.00 120.00  152
 17  ω    -13.00  43.00   0.50    0.40    --   48.70 -38.00  60.00  112
 18  ω     -2.00  26.00   0.50    0.40    --   48.70 -19.00-150.00   56
 19  ω    -75.00 -50.00   0.50    1.60    --  -86.25 122.00  20.00   50
 20  ω    112.00 170.00   0.50    1.60    --  107.75 114.00 -66.89  116
 21  ω     93.00 159.00   0.50    1.60    --  107.75  77.00   0.00  132
 22  ω     77.00 106.00   0.50    1.60    --  107.75-125.00-120.00   58
 23  ω     96.00 122.00   0.50    1.60    --  107.75 -86.00 -75.12   52
 24  ω     70.00 105.00   0.50    1.60    --  107.75 -95.00  90.00   70
 25  ω    102.00 153.00   0.50    1.60    --  107.75  15.00-120.00  102
 26  ω     36.00  62.00   0.50    1.60    --  107.75 -61.00   0.00   52
 27  ω     40.00  77.00   0.50    1.60    --  107.75 -74.00-152.87   74
 28  ω     47.00  72.00   0.50    1.60    --  107.75 -86.00 -75.12   50
 29  ω    146.00 177.00   0.50    1.60    --  107.75 125.00 120.00   62
 30  ω    130.00 174.00   0.50    1.60    --  107.75  59.00 -31.39   88
 31  ω     94.00 120.00   0.50    1.60    --  107.75  59.00 -31.39   52
 32  ω    120.00 146.00   0.50    1.60    --  107.75 125.00   0.00   52
 33  ω     83.00 109.00   0.50    1.60    --  107.75-125.00-150.00   52
 34  ω     36.00  71.00   0.50    1.60    --  107.75 -61.00 -30.00   70
 35  ω     45.00  70.00   0.50    1.60    --  107.75 -61.00  30.00   50
 36  ω     87.00 168.00   0.50    1.60    --  107.75  77.00 -90.00  162
 37  ω     48.00 101.00   0.50    1.60    --  107.75 -77.00 -60.00  106
 38  ω     98.00 161.00   0.50    1.60    --  107.75 125.00  30.00  126
 39  ω     38.00  68.00   0.50    1.60    --  107.75 -77.00  30.00   60
 40  ω     63.00  89.00   0.50    1.60    --  107.75-125.00  60.00   52
 41  ω     98.00 134.00   0.50    1.60    --  107.75  45.00-150.00   72
 42  ω    153.00 178.00   0.50    1.60    --  107.75  45.00-150.00   50
 43  ω    119.00 145.00   0.50    1.60    --  107.75  61.00 150.00   52
 44  ω    105.00 178.00   0.50    1.60    --  107.75  45.00 120.00  146
;
_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      0.0179822000
_diffrn_orient_matrix_UB_12      0.1741340000
_diffrn_orient_matrix_UB_13      0.0163291000
_diffrn_orient_matrix_UB_21      -0.0228517000
_diffrn_orient_matrix_UB_22      -0.0653531000
_diffrn_orient_matrix_UB_23      0.0421681000
_diffrn_orient_matrix_UB_31      0.2439809000
_diffrn_orient_matrix_UB_32      -0.0189908000
_diffrn_orient_matrix_UB_33      0.0046170000
_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                3496
_reflns_number_total             3681
_reflns_odcompleteness_completeness 97.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.6763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C10(H10A,H10B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1 O 0.44512(12) 0.33104(9) 0.28087(2) 0.01817(16) Uani 1 1 d . . . . .
O2 O 0.24691(11) 0.24498(9) 0.28896(2) 0.01723(15) Uani 1 1 d . . . . .
O3 O 0.46815(11) 0.02864(9) 0.30979(2) 0.01675(16) Uani 1 1 d . . . . .
O4 O 0.44082(12) -0.04261(9) 0.27054(2) 0.01965(16) Uani 1 1 d . . . . .
H4 H 0.403(3) -0.146(2) 0.2769(5) 0.042(4) Uiso 1 1 d . . . . .
O5 O 0.34086(12) 0.54197(8) 0.32194(2) 0.01790(16) Uani 1 1 d . . . . .
O6 O 0.30233(14) 0.64534(9) 0.28755(2) 0.02356(18) Uani 1 1 d . . . . .
H6 H 0.224(3) 0.587(2) 0.2725(5) 0.042(4) Uiso 1 1 d . . . . .
O9 O 0.30212(12) -0.02667(9) 0.40073(2) 0.02033(16) Uani 1 1 d . . . . .
O10 O 0.63664(11) 0.06215(8) 0.39352(2) 0.01736(16) Uani 1 1 d . . . . .
O19 O 0.28204(13) 0.79716(10) 0.51729(2) 0.02606(18) Uani 1 1 d . . . . .
O20 O 0.28306(12) 0.57426(10) 0.55119(2) 0.02125(17) Uani 1 1 d . . . . .
N19 N 0.27370(13) 0.64873(11) 0.51981(2) 0.01780(18) Uani 1 1 d . . . . .
C3 C 0.28610(16) 0.12285(12) 0.31809(3) 0.01515(19) Uani 1 1 d . . . . .
C4 C 0.35355(15) 0.20437(11) 0.35852(3) 0.01378(19) Uani 1 1 d . . . . .
C5 C 0.53453(15) 0.32662(12) 0.35141(3) 0.01466(19) Uani 1 1 d . . . . .
H5A H 0.547604 0.400609 0.374376 0.018 Uiso 1 1 calc R U . . .
H5B H 0.670296 0.265980 0.350165 0.018 Uiso 1 1 calc R U . . .
C6 C 0.50546(16) 0.42893(12) 0.31401(3) 0.0165(2) Uani 1 1 d . . . . .
C7 C 0.08076(16) 0.02540(13) 0.31664(3) 0.0193(2) Uani 1 1 d . . . . .
H7A H -0.040630 0.098601 0.319609 0.029 Uiso 1 1 calc R U . . .
H7B H 0.084942 -0.054262 0.338108 0.029 Uiso 1 1 calc R U . . .
H7C H 0.065328 -0.031096 0.291261 0.029 Uiso 1 1 calc R U . . .
C8 C 0.71123(18) 0.50867(14) 0.30196(3) 0.0227(2) Uani 1 1 d . . . . .
H8A H 0.814027 0.424763 0.295107 0.034 Uiso 1 1 calc R U . . .
H8B H 0.770645 0.573821 0.323939 0.034 Uiso 1 1 calc R U . . .
H8C H 0.681732 0.578867 0.279063 0.034 Uiso 1 1 calc R U . . .
C9 C 0.42672(16) 0.06709(12) 0.38666(3) 0.01501(19) Uani 1 1 d . . . . .
C10 C 0.71615(17) -0.07316(13) 0.41772(3) 0.0214(2) Uani 1 1 d . . . . .
H10A H 0.619771 -0.091862 0.439663 0.026 Uiso 1 1 calc R U . . .
H10B H 0.859496 -0.046574 0.429204 0.026 Uiso 1 1 calc R U . . .
C11 C 0.72834(18) -0.22443(13) 0.39299(3) 0.0232(2) Uani 1 1 d . . . . .
H11A H 0.824480 -0.205767 0.371392 0.035 Uiso 1 1 calc R U . . .
H11B H 0.585789 -0.251596 0.382071 0.035 Uiso 1 1 calc R U . . .
H11C H 0.782687 -0.314339 0.409422 0.035 Uiso 1 1 calc R U . . .
C12 C 0.15328(15) 0.28469(12) 0.37588(3) 0.01496(19) Uani 1 1 d . . . . .
H12A H 0.088655 0.359169 0.355855 0.018 Uiso 1 1 calc R U . . .
H12B H 0.047393 0.198803 0.380865 0.018 Uiso 1 1 calc R U . . .
C13 C 0.19620(14) 0.37878(12) 0.41376(3) 0.01456(19) Uani 1 1 d . . . . .
C14 C 0.21503(15) 0.54751(12) 0.41299(3) 0.0164(2) Uani 1 1 d . . . . .
H14 H 0.209283 0.602224 0.388323 0.020 Uiso 1 1 calc R U . . .
C15 C 0.24194(15) 0.63706(12) 0.44746(3) 0.0166(2) Uani 1 1 d . . . . .
H15 H 0.254219 0.751912 0.446681 0.020 Uiso 1 1 calc R U . . .
C16 C 0.25043(15) 0.55443(12) 0.48307(3) 0.0157(2) Uani 1 1 d . . . . .
C17 C 0.23468(15) 0.38667(13) 0.48519(3) 0.0159(2) Uani 1 1 d . . . . .
H17 H 0.242522 0.332689 0.509949 0.019 Uiso 1 1 calc R U . . .
C18 C 0.20726(15) 0.29953(12) 0.45036(3) 0.0159(2) Uani 1 1 d . . . . .
H18 H 0.195820 0.184656 0.451318 0.019 Uiso 1 1 calc R U . . .


_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 O2 1.4672(10) . ?
O1 C6 1.4222(12) . ?
O2 C3 1.4248(11) . ?
O3 O4 1.4590(9) . ?
O3 C3 1.4188(12) . ?
O4 H4 0.910(18) . ?
O5 O6 1.4567(9) . ?
O5 C6 1.4246(12) . ?
O6 H6 0.843(19) . ?
O9 C9 1.2109(13) . ?
O10 C9 1.3288(12) . ?
O10 C10 1.4603(12) . ?
O19 N19 1.2273(12) . ?
O20 N19 1.2281(11) . ?
N19 C16 1.4710(12) . ?
C3 C4 1.5695(13) . ?
C3 C7 1.5173(14) . ?
C4 C5 1.5443(13) . ?
C4 C9 1.5382(13) . ?
C4 C12 1.5571(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5280(13) . ?
C6 C8 1.5195(14) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5062(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5154(13) . ?
C13 C14 1.3957(14) . ?
C13 C18 1.4020(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.3872(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.3856(14) . ?
C16 C17 1.3881(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3872(14) . ?
C18 H18 0.9500 . ?

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
C6 O1 O2 109.07(6) . . ?
C3 O2 O1 110.33(7) . . ?
C3 O3 O4 109.62(7) . . ?
O3 O4 H4 100.4(10) . . ?
C6 O5 O6 109.21(7) . . ?
O5 O6 H6 103.0(12) . . ?
C9 O10 C10 115.81(8) . . ?
O19 N19 O20 123.90(9) . . ?
O19 N19 C16 118.06(8) . . ?
O20 N19 C16 118.04(9) . . ?
O2 C3 C4 109.65(8) . . ?
O2 C3 C7 103.24(8) . . ?
O3 C3 O2 111.50(7) . . ?
O3 C3 C4 102.53(7) . . ?
O3 C3 C7 113.17(8) . . ?
C7 C3 C4 116.96(8) . . ?
C5 C4 C3 108.47(7) . . ?
C5 C4 C12 113.05(8) . . ?
C9 C4 C3 106.88(7) . . ?
C9 C4 C5 111.95(8) . . ?
C9 C4 C12 107.63(8) . . ?
C12 C4 C3 108.63(8) . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 115.20(8) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
O1 C6 O5 110.39(8) . . ?
O1 C6 C5 111.24(8) . . ?
O1 C6 C8 103.56(8) . . ?
O5 C6 C5 105.48(7) . . ?
O5 C6 C8 113.48(8) . . ?
C8 C6 C5 112.83(8) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O9 C9 O10 124.24(9) . . ?
O9 C9 C4 122.19(9) . . ?
O10 C9 C4 113.58(8) . . ?
O10 C10 H10A 109.7 . . ?
O10 C10 H10B 109.7 . . ?
O10 C10 C11 110.05(8) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 108.6 . . ?
C4 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C4 114.83(8) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C14 C13 C12 120.41(9) . . ?
C14 C13 C18 118.64(9) . . ?
C18 C13 C12 120.88(9) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.45(9) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.9 . . ?
C16 C15 C14 118.19(9) . . ?
C16 C15 H15 120.9 . . ?
C15 C16 N19 118.55(9) . . ?
C15 C16 C17 122.29(9) . . ?
C17 C16 N19 119.15(9) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.56(9) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.86(9) . . ?
C17 C18 H18 119.6 . . ?

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
O4 H4 O6 0.910(18) 1.875(18) 2.7824(11) 174.7(16) 1_545 yes
O6 H6 O4 0.843(19) 2.055(19) 2.8921(11) 171.7(16) 2 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
O1 O2 C3 O3 -46.96(9) . . . . ?
O1 O2 C3 C4 65.88(9) . . . . ?
O1 O2 C3 C7 -168.77(7) . . . . ?
O2 O1 C6 O5 -58.74(9) . . . . ?
O2 O1 C6 C5 58.00(9) . . . . ?
O2 O1 C6 C8 179.45(7) . . . . ?
O2 C3 C4 C5 -50.48(10) . . . . ?
O2 C3 C4 C9 -171.37(7) . . . . ?
O2 C3 C4 C12 72.76(9) . . . . ?
O3 C3 C4 C5 68.07(9) . . . . ?
O3 C3 C4 C9 -52.81(9) . . . . ?
O3 C3 C4 C12 -168.69(7) . . . . ?
O4 O3 C3 O2 -56.62(9) . . . . ?
O4 O3 C3 C4 -173.86(7) . . . . ?
O4 O3 C3 C7 59.25(9) . . . . ?
O6 O5 C6 O1 -59.74(9) . . . . ?
O6 O5 C6 C5 180.00(7) . . . . ?
O6 O5 C6 C8 56.00(10) . . . . ?
O19 N19 C16 C15 0.86(13) . . . . ?
O19 N19 C16 C17 -178.23(9) . . . . ?
O20 N19 C16 C15 -179.34(9) . . . . ?
O20 N19 C16 C17 1.57(13) . . . . ?
N19 C16 C17 C18 178.36(8) . . . . ?
C3 C4 C5 C6 41.48(10) . . . . ?
C3 C4 C9 O9 -72.84(11) . . . . ?
C3 C4 C9 O10 106.84(9) . . . . ?
C3 C4 C12 C13 -176.00(8) . . . . ?
C4 C5 C6 O1 -47.04(11) . . . . ?
C4 C5 C6 O5 72.66(10) . . . . ?
C4 C5 C6 C8 -162.92(8) . . . . ?
C4 C12 C13 C14 99.83(10) . . . . ?
C4 C12 C13 C18 -83.36(11) . . . . ?
C5 C4 C9 O9 168.52(9) . . . . ?
C5 C4 C9 O10 -11.80(11) . . . . ?
C5 C4 C12 C13 -55.55(11) . . . . ?
C6 O1 O2 C3 -70.63(9) . . . . ?
C7 C3 C4 C5 -167.52(8) . . . . ?
C7 C3 C4 C9 71.60(10) . . . . ?
C7 C3 C4 C12 -44.27(11) . . . . ?
C9 O10 C10 C11 79.85(11) . . . . ?
C9 C4 C5 C6 159.17(8) . . . . ?
C9 C4 C12 C13 68.62(10) . . . . ?
C10 O10 C9 O9 4.02(14) . . . . ?
C10 O10 C9 C4 -175.65(8) . . . . ?
C12 C4 C5 C6 -79.06(10) . . . . ?
C12 C4 C9 O9 43.69(12) . . . . ?
C12 C4 C9 O10 -136.63(8) . . . . ?
C12 C13 C14 C15 176.21(9) . . . . ?
C12 C13 C18 C17 -176.38(8) . . . . ?
C13 C14 C15 C16 0.18(14) . . . . ?
C14 C13 C18 C17 0.49(14) . . . . ?
C14 C15 C16 N19 -178.54(8) . . . . ?
C14 C15 C16 C17 0.52(14) . . . . ?
C15 C16 C17 C18 -0.70(15) . . . . ?
C16 C17 C18 C13 0.17(14) . . . . ?
C18 C13 C14 C15 -0.67(14) . . . . ?

_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 1.194
_oxdiff_exptl_absorpt_empirical_full_min 0.895
####################################################################### 
# 
# 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_23bl_1542
_database_code_depnum_ccdc_archive 'CCDC 2476570'
loop_
_audit_author_name
_audit_author_address
'Anna Dmitrievna Maksimova'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N O9'
_chemical_formula_sum            'C16 H21 N O9'
_chemical_formula_weight         371.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2471(9)
_cell_length_b                   7.9047(10)
_cell_length_c                   30.181(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.709(5)
_cell_angle_gamma                90
_cell_volume                     1728.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9804
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      67.71

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.009
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13715
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         67.726
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3117
_reflns_number_gt                2967
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0358P)²+0.7627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.44046(14) 0.23008(13) 0.34811(3) 0.0312(2) Uani 1 1 d . . . . .
H1 H 0.378(3) 0.128(3) 0.3444(7) 0.061(6) Uiso 1 1 d . . . . .
O2 O 0.45232(13) 0.27165(12) 0.30103(3) 0.0286(2) Uani 1 1 d . . . . .
O3 O 0.15614(12) 0.37734(11) 0.29825(3) 0.0213(2) Uani 1 1 d . . . . .
O4 O 0.04389(13) 0.64623(12) 0.28088(3) 0.0269(2) Uani 1 1 d . . . . .
O5 O -0.07085(16) 0.57319(14) 0.24462(4) 0.0380(3) Uani 1 1 d . . . . .
H5 H -0.100(3) 0.676(3) 0.2310(7) 0.063(6) Uiso 1 1 d . . . . .
O6 O 0.28374(13) 0.90543(12) 0.34068(3) 0.0273(2) Uani 1 1 d . . . . .
O7 O 0.01359(12) 0.82624(11) 0.36884(3) 0.0247(2) Uani 1 1 d . . . . .
O8 O 0.72389(19) 0.85827(15) 0.54522(4) 0.0537(4) Uani 1 1 d . . . . .
O9 O 0.92534(16) 0.69543(17) 0.51513(4) 0.0476(3) Uani 1 1 d . . . . .
N1 N 0.76981(19) 0.75520(16) 0.51705(4) 0.0367(3) Uani 1 1 d . . . . .
C1 C 0.34734(18) 0.41783(16) 0.29141(5) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.38844(18) 0.57147(16) 0.32127(5) 0.0221(3) Uani 1 1 d . . . . .
H2A H 0.417(2) 0.666(2) 0.3024(5) 0.027 Uiso 1 1 d . U . . .
H2B H 0.493(2) 0.548(2) 0.3419(5) 0.027 Uiso 1 1 d . U . . .
C3 C 0.21102(17) 0.60695(16) 0.34617(4) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.06378(17) 0.52120(16) 0.31450(4) 0.0213(3) Uani 1 1 d . . . . .
C5 C 0.3803(2) 0.44444(19) 0.24243(5) 0.0319(3) Uani 1 1 d . . . . .
H5A H 0.334(3) 0.344(3) 0.2252(6) 0.048 Uiso 1 1 d . U . . .
H5B H 0.308(3) 0.546(3) 0.2328(6) 0.048 Uiso 1 1 d . U . . .
H5C H 0.514(3) 0.461(2) 0.2388(6) 0.048 Uiso 1 1 d . U . . .
C6 C -0.11719(18) 0.46528(19) 0.33252(5) 0.0271(3) Uani 1 1 d . . . . .
H6A H -0.098(2) 0.380(2) 0.3559(6) 0.041 Uiso 1 1 d . U . . .
H6B H -0.181(2) 0.563(2) 0.3451(6) 0.041 Uiso 1 1 d . U . . .
H6C H -0.191(2) 0.417(2) 0.3084(6) 0.041 Uiso 1 1 d . U . . .
C7 C 0.17615(17) 0.79675(16) 0.35071(4) 0.0210(3) Uani 1 1 d . . . . .
C8 C -0.0426(2) 1.00253(17) 0.37288(5) 0.0274(3) Uani 1 1 d . . . . .
H8A H 0.065(2) 1.068(2) 0.3857(6) 0.033 Uiso 1 1 d . U . . .
H8B H -0.071(2) 1.043(2) 0.3422(6) 0.033 Uiso 1 1 d . U . . .
C9 C -0.2070(3) 1.0051(2) 0.40167(7) 0.0456(4) Uani 1 1 d . . . . .
H9A H -0.167(3) 0.966(3) 0.4328(8) 0.068 Uiso 1 1 d . U . . .
H9B H -0.250(3) 1.120(3) 0.4045(7) 0.068 Uiso 1 1 d . U . . .
H9C H -0.301(3) 0.937(3) 0.3890(8) 0.068 Uiso 1 1 d . U . . .
C10 C 0.20833(18) 0.52366(17) 0.39272(4) 0.0219(3) Uani 1 1 d . . . . .
H10A H 0.090(2) 0.545(2) 0.4060(5) 0.026 Uiso 1 1 d . U . . .
H10B H 0.220(2) 0.402(2) 0.3887(5) 0.026 Uiso 1 1 d . U . . .
C11 C 0.35850(18) 0.58729(16) 0.42445(4) 0.0233(3) Uani 1 1 d . . . . .
C12 C 0.53181(19) 0.50999(18) 0.42681(5) 0.0266(3) Uani 1 1 d . . . . .
H12 H 0.556(2) 0.413(2) 0.4071(6) 0.032 Uiso 1 1 d . U . . .
C13 C 0.6688(2) 0.56603(19) 0.45650(5) 0.0290(3) Uani 1 1 d . . . . .
H13 H 0.788(2) 0.512(2) 0.4579(6) 0.035 Uiso 1 1 d . U . . .
C14 C 0.6280(2) 0.69839(18) 0.48438(5) 0.0289(3) Uani 1 1 d . . . . .
C15 C 0.4571(2) 0.77679(19) 0.48343(5) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.429(2) 0.862(2) 0.5039(6) 0.036 Uiso 1 1 d . U . . .
C16 C 0.3238(2) 0.72153(18) 0.45300(5) 0.0268(3) Uani 1 1 d . . . . .
H16 H 0.208(2) 0.770(2) 0.4518(6) 0.032 Uiso 1 1 d . U . . .


_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 O2 1.4637(15) . ?
O1 H1 0.93(2) . ?
O2 C1 1.4090(16) . ?
O3 C4 1.4147(15) . ?
O3 C1 1.4430(15) . ?
O4 C4 1.4208(16) . ?
O4 O5 1.4723(13) . ?
O5 H5 0.93(2) . ?
O6 C7 1.2048(16) . ?
O7 C7 1.3342(16) . ?
O7 C8 1.4581(16) . ?
O8 N1 1.2306(19) . ?
O9 N1 1.2251(18) . ?
N1 C14 1.4730(18) . ?
C1 C5 1.519(2) . ?
C1 C2 1.5361(18) . ?
C2 C3 1.5344(18) . ?
C2 H2A 0.965(17) . ?
C2 H2B 0.985(16) . ?
C3 C7 1.5283(17) . ?
C3 C10 1.5522(17) . ?
C3 C4 1.5656(17) . ?
C4 C6 1.5012(19) . ?
C5 H5A 1.00(2) . ?
C5 H5B 1.00(2) . ?
C5 H5C 0.98(2) . ?
C6 H6A 0.983(19) . ?
C6 H6B 0.982(19) . ?
C6 H6C 0.969(19) . ?
C8 C9 1.495(2) . ?
C8 H8A 1.000(18) . ?
C8 H8B 0.995(18) . ?
C9 H9A 1.02(2) . ?
C9 H9B 0.97(2) . ?
C9 H9C 0.94(2) . ?
C10 C11 1.5140(18) . ?
C10 H10A 0.971(16) . ?
C10 H10B 0.976(17) . ?
C11 C16 1.394(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.988(17) . ?
C13 C14 1.380(2) . ?
C13 H13 0.966(17) . ?
C14 C15 1.385(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.938(19) . ?
C16 H16 0.923(17) . ?

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
O2 O1 H1 97.0(13) . . ?
C1 O2 O1 109.70(9) . . ?
C4 O3 C1 109.73(9) . . ?
C4 O4 O5 107.52(9) . . ?
O4 O5 H5 95.7(14) . . ?
C7 O7 C8 116.98(10) . . ?
O9 N1 O8 123.79(13) . . ?
O9 N1 C14 118.39(14) . . ?
O8 N1 C14 117.81(14) . . ?
O2 C1 O3 107.67(10) . . ?
O2 C1 C5 102.38(11) . . ?
O3 C1 C5 110.45(11) . . ?
O2 C1 C2 115.69(11) . . ?
O3 C1 C2 105.17(10) . . ?
C5 C1 C2 115.35(11) . . ?
C3 C2 C1 106.33(10) . . ?
C3 C2 H2A 110.3(9) . . ?
C1 C2 H2A 107.9(10) . . ?
C3 C2 H2B 111.6(9) . . ?
C1 C2 H2B 110.6(9) . . ?
H2A C2 H2B 110.0(13) . . ?
C7 C3 C2 111.50(10) . . ?
C7 C3 C10 109.19(10) . . ?
C2 C3 C10 113.53(10) . . ?
C7 C3 C4 111.60(10) . . ?
C2 C3 C4 100.81(10) . . ?
C10 C3 C4 110.01(10) . . ?
O3 C4 O4 110.51(10) . . ?
O3 C4 C6 108.45(11) . . ?
O4 C4 C6 113.11(11) . . ?
O3 C4 C3 103.81(10) . . ?
O4 C4 C3 100.82(10) . . ?
C6 C4 C3 119.56(11) . . ?
C1 C5 H5A 109.6(11) . . ?
C1 C5 H5B 107.4(11) . . ?
H5A C5 H5B 109.2(15) . . ?
C1 C5 H5C 108.0(11) . . ?
H5A C5 H5C 111.2(16) . . ?
H5B C5 H5C 111.5(16) . . ?
C4 C6 H6A 110.8(10) . . ?
C4 C6 H6B 109.6(11) . . ?
H6A C6 H6B 108.6(15) . . ?
C4 C6 H6C 108.4(11) . . ?
H6A C6 H6C 109.6(15) . . ?
H6B C6 H6C 109.9(14) . . ?
O6 C7 O7 124.37(12) . . ?
O6 C7 C3 124.57(12) . . ?
O7 C7 C3 111.02(11) . . ?
O7 C8 C9 106.92(12) . . ?
O7 C8 H8A 108.0(10) . . ?
C9 C8 H8A 113.1(10) . . ?
O7 C8 H8B 106.3(10) . . ?
C9 C8 H8B 112.9(10) . . ?
H8A C8 H8B 109.3(14) . . ?
C8 C9 H9A 108.8(13) . . ?
C8 C9 H9B 109.1(14) . . ?
H9A C9 H9B 106.9(19) . . ?
C8 C9 H9C 109.8(14) . . ?
H9A C9 H9C 112.3(19) . . ?
H9B C9 H9C 110(2) . . ?
C11 C10 C3 113.79(10) . . ?
C11 C10 H10A 107.8(9) . . ?
C3 C10 H10A 109.4(9) . . ?
C11 C10 H10B 110.0(9) . . ?
C3 C10 H10B 107.5(9) . . ?
H10A C10 H10B 108.2(13) . . ?
C16 C11 C12 118.68(13) . . ?
C16 C11 C10 120.27(12) . . ?
C12 C11 C10 121.01(12) . . ?
C13 C12 C11 121.16(14) . . ?
C13 C12 H12 119.8(10) . . ?
C11 C12 H12 119.1(10) . . ?
C14 C13 C12 118.19(13) . . ?
C14 C13 H13 121.2(10) . . ?
C12 C13 H13 120.5(10) . . ?
C13 C14 C15 122.32(13) . . ?
C13 C14 N1 118.75(13) . . ?
C15 C14 N1 118.91(14) . . ?
C16 C15 C14 118.60(14) . . ?
C16 C15 H15 120.2(11) . . ?
C14 C15 H15 121.2(11) . . ?
C15 C16 C11 121.02(14) . . ?
C15 C16 H16 120.5(11) . . ?
C11 C16 H16 118.4(11) . . ?

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
O1 O2 C1 O3 -65.25(12) . . . . ?
O1 O2 C1 C5 178.30(10) . . . . ?
O1 O2 C1 C2 52.01(14) . . . . ?
C4 O3 C1 O2 145.99(10) . . . . ?
C4 O3 C1 C5 -102.97(12) . . . . ?
C4 O3 C1 C2 22.09(13) . . . . ?
O2 C1 C2 C3 -116.24(12) . . . . ?
O3 C1 C2 C3 2.41(13) . . . . ?
C5 C1 C2 C3 124.35(12) . . . . ?
C1 C2 C3 C7 -141.21(11) . . . . ?
C1 C2 C3 C10 94.95(12) . . . . ?
C1 C2 C3 C4 -22.64(12) . . . . ?
C1 O3 C4 O4 70.28(12) . . . . ?
C1 O3 C4 C6 -165.21(10) . . . . ?
C1 O3 C4 C3 -37.07(12) . . . . ?
O5 O4 C4 O3 62.26(12) . . . . ?
O5 O4 C4 C6 -59.54(13) . . . . ?
O5 O4 C4 C3 171.59(9) . . . . ?
C7 C3 C4 O3 154.29(10) . . . . ?
C2 C3 C4 O3 35.80(12) . . . . ?
C10 C3 C4 O3 -84.34(12) . . . . ?
C7 C3 C4 O4 39.81(13) . . . . ?
C2 C3 C4 O4 -78.68(11) . . . . ?
C10 C3 C4 O4 161.18(10) . . . . ?
C7 C3 C4 C6 -84.78(14) . . . . ?
C2 C3 C4 C6 156.73(12) . . . . ?
C10 C3 C4 C6 36.59(15) . . . . ?
C8 O7 C7 O6 5.74(18) . . . . ?
C8 O7 C7 C3 -176.63(10) . . . . ?
C2 C3 C7 O6 -7.93(18) . . . . ?
C10 C3 C7 O6 118.33(14) . . . . ?
C4 C3 C7 O6 -119.83(14) . . . . ?
C2 C3 C7 O7 174.45(10) . . . . ?
C10 C3 C7 O7 -59.30(13) . . . . ?
C4 C3 C7 O7 62.55(14) . . . . ?
C7 O7 C8 C9 -169.06(13) . . . . ?
C7 C3 C10 C11 -62.60(14) . . . . ?
C2 C3 C10 C11 62.49(15) . . . . ?
C4 C3 C10 C11 174.60(11) . . . . ?
C3 C10 C11 C16 92.94(15) . . . . ?
C3 C10 C11 C12 -89.15(15) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C10 C11 C12 C13 -178.75(12) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C12 C13 C14 N1 177.94(13) . . . . ?
O9 N1 C14 C13 7.8(2) . . . . ?
O8 N1 C14 C13 -171.03(14) . . . . ?
O9 N1 C14 C15 -173.77(14) . . . . ?
O8 N1 C14 C15 7.4(2) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
N1 C14 C15 C16 -179.29(13) . . . . ?
C14 C15 C16 C11 1.4(2) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
C10 C11 C16 C15 177.36(12) . . . . ?

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
O1 H1 O6 0.93(2) 1.89(2) 2.8126(14) 172(2) 1_545 yes
O5 H5 O3 0.93(2) 1.86(2) 2.7909(14) 178(2) 2 yes

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_RM-3-I
_database_code_depnum_ccdc_archive 'CCDC 2476565'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-03-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O8'
_chemical_formula_sum            'C16 H19 N O8'
_chemical_formula_weight         353.32
_chemical_absolute_configuration uknown
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19NO8
_chemical_oxdiff_usercomment     RM-3-I
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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   6.83692(6)
_cell_length_b                   21.3655(2)
_cell_length_c                   11.21195(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.5169(8)
_cell_angle_gamma                90
_cell_volume                     1637.20(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18008
_cell_measurement_temperature    99.97(18)
_cell_measurement_theta_max      77.6120
_cell_measurement_theta_min      4.1020
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.1451
0 1 -1 0.1800
-1 1 0 0.1394
1 -1 0 0.3369
0 4 7 0.1807
0 -4 -7 0.0365
3 3 -6 0.1634
-3 -8 3 0.2129
-2 12 2 0.1700
1 -11 -4 0.1404
3 11 1 0.3237

_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.23
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 -1.0001 0.9997 0.0489 0.0977 0.1101
-0.0002 1.0001 -0.9997 -0.0489 -0.0977 -0.1101
-1.0000 0.9988 -0.0005 0.2032 -0.1127 -0.0449
1.0000 -0.9988 0.0005 -0.2032 0.1127 0.0449
0.1887 4.2873 6.9037 0.1991 -0.0919 0.9757
-0.4260 -4.0972 -6.8968 -0.1502 0.0686 -0.9863
2.5855 2.7078 -5.8521 -0.8071 -0.2414 -0.5389
-3.3254 -7.9468 2.5559 0.8780 0.4779 -0.0259
-1.8922 12.1543 1.7144 0.3626 -0.8747 0.3215
1.4279 -10.6413 -4.0974 -0.3731 0.6820 -0.6291
2.5553 11.2185 0.7429 -0.6113 -0.6439 0.4601

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20824
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.754
_diffrn_reflns_theta_min         4.138
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(18)
_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 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    101.00 129.00   0.50    0.10    --  107.75-150.00 123.70   56
  2  ω     57.00  83.00   0.50    0.10    --  107.75-150.00 123.70   52
  3  ω     39.00 111.00   0.50    0.10    --  107.75-125.00 -90.00  144
  4  ω     73.00 100.00   0.50    0.10    --  107.75-125.00-150.00   54
  5  ω     39.00 111.00   0.50    0.10    --  107.75-125.00-120.00  144
  6  ω     57.00 143.00   0.50    0.10    --  107.75-169.00-119.45  172
  7  ω     78.00 108.00   0.50    0.10    --  107.75-125.00 -60.00   60
  8  ω     39.00 111.00   0.50    0.10    --  107.75-125.00   0.00  144
  9  ω     39.00 111.00   0.50    0.10    --  107.75-125.00  30.00  144
 10  ω     81.00 107.00   0.50    0.10    --  107.75-106.00  -5.54   52
 11  ω     39.00 107.00   0.50    0.10    --  107.75-106.00  33.00  136
 12  ω     36.00 105.00   0.50    0.10    --  107.75 -95.00   0.00  138
 13  ω     39.00 111.00   0.50    0.10    --  107.75-125.00 150.00  144
 14  ω     69.00 102.00   0.50    0.10    --  107.75 -95.00  60.00   66
 15  ω     19.00  83.00   0.50    0.05    --   48.70-106.00  33.00  128
 16  ω     36.00 105.00   0.50    0.10    --  107.75 -95.00 -90.00  138
 17  ω     73.00 104.00   0.50    0.10    --  107.75 -95.00-150.00   62
 18  ω     76.00 102.00   0.50    0.10    --  107.75 -95.00-180.00   52
 19  ω     95.00 121.00   0.50    0.10    --  107.75 -87.00  19.96   52
 20  ω     40.00 100.00   0.50    0.10    --  107.75 -77.00  30.00  120
 21  ω     36.00  92.00   0.50    0.10    --  107.75 -77.00  90.00  112
 22  ω     39.00  68.00   0.50    0.10    --  107.75 -71.00  62.40   58
 23  ω     36.00  68.00   0.50    0.10    --  107.75 -61.00 -30.00   64
 24  ω     47.00  72.00   0.50    0.10    --  107.75 -64.00-102.33   50
 25  ω     40.00  66.00   0.50    0.10    --  107.75 -61.00-120.00   52
 26  ω     36.00  64.00   0.50    0.10    --  107.75 -77.00-120.00   56
 27  ω     37.00  63.00   0.50    0.10    --  107.75 -61.00-150.00   52
 28  ω     72.00 105.00   0.50    0.10    --  107.75 -77.00-120.00   66
 29  ω     36.00  71.00   0.50    0.10    --  107.75 -61.00  90.00   70
 30  ω     36.00  71.00   0.50    0.10    --  107.75 -61.00 120.00   70
 31  ω     42.00  68.00   0.50    0.10    --  107.75 -61.00 150.00   52
 32  ω    -25.00  26.00   0.50    0.05    --   48.70 -19.00  90.00  102
 33  ω    -25.00  26.00   0.50    0.05    --   48.70 -19.00   0.00  102
 34  ω     36.00  62.00   0.50    0.10    --  107.75 -55.00 134.54   52
 35  ω    143.00 175.00   0.50    0.10    --  107.75  15.00 -30.00   64
 36  ω    100.00 126.00   0.50    0.10    --  107.75  61.00  60.00   52
 37  ω    133.00 175.00   0.50    0.10    --  107.75  77.00   0.00   84
 38  ω    152.00 177.00   0.50    0.10    --  107.75  61.00  60.00   50
 39  ω     94.00 142.00   0.50    0.10    --  107.75  61.00   0.00   96
 40  ω     93.00 178.00   0.50    0.10    --  107.75  61.00  30.00  170
 41  ω    127.00 153.00   0.50    0.10    --  107.75  61.00 -90.00   52
 42  ω     93.00 178.00   0.50    0.10    --  107.75  61.00-150.00  170
 43  ω     90.00 115.00   0.50    0.10    --  107.75  77.00-180.00   50
 44  ω    140.00 174.00   0.50    0.10    --  107.75  77.00-180.00   68
 45  ω    141.00 167.00   0.50    0.10    --  107.75  45.00-150.00   52
 46  ω    112.00 138.00   0.50    0.10    --  107.75  45.00-150.00   52
 47  ω    111.00 177.00   0.50    0.10    --  107.75  45.00-120.00  132
 48  ω    112.00 138.00   0.50    0.10    --  107.75  45.00 -60.00   52
 49  ω    115.00 178.00   0.50    0.10    --  107.75  45.00 -30.00  126
 50  ω     97.00 178.00   0.50    0.10    --  107.75  15.00 -60.00  162
 51  ω     98.00 129.00   0.50    0.10    --  107.75  45.00   0.00   62
 52  ω     95.00 177.00   0.50    0.10    --  107.75 125.00  90.00  164
 53  ω    105.00 177.00   0.50    0.10    --  107.75 106.00 132.00  144
 54  ω    152.00 177.00   0.50    0.10    --  107.75 125.00 150.00   50
 55  ω    122.00 148.00   0.50    0.10    --  107.75 124.00  56.74   52
 56  ω    103.00 129.00   0.50    0.10    --  107.75 125.00  30.00   52
 57  ω    117.00 153.00   0.50    0.10    --  107.75 125.00-150.00   72
 58  ω    -70.00  24.00   0.50    0.05    --  -48.70  77.00-120.00  188
 59  ω    -51.00 -14.00   0.50    0.10    --  -86.25  45.00 -30.00   74
 60  ω    -51.00 -14.00   0.50    0.10    --  -86.25  45.00  60.00   74
 61  ω    -43.00  24.00   0.50    0.05    --  -48.70  38.00 120.00  134
 62  ω    -81.00 -17.00   0.50    0.10    --  -86.25 106.00 132.00  128
 63  ω    -82.00   2.00   0.50    0.05    --  -48.70 106.00 132.00  168
 64  ω   -155.00 -83.00   0.50    0.10    --  -86.25-106.00  33.00  144
 65  ω   -118.00 -73.00   0.50    0.05    --  -48.70-125.00-150.00   90
 66  ω   -118.00 -73.00   0.50    0.05    --  -48.70-125.00-180.00   90
 67  ω    -64.00 -39.00   0.50    0.05    --  -48.70 106.00 132.00   50
 68  ω    -91.00 -65.00   0.50    0.10    --  -86.25 -75.00  78.97   52
 69  ω     36.00  61.00   0.50    0.10    --  107.75 -61.00  30.00   50
 70  ω    -64.00 -39.00   0.50    0.05    --  -48.70 106.00 132.00   50
 71  ω     94.00 120.00   0.50    0.10    --  107.75  71.00 -10.69   52
 72  ω     27.00  52.00   0.50    0.05    --   48.69-106.00  33.00   50
 73  ω     81.00 107.00   0.50    0.10    --  107.75-105.00 144.95   52
 74  ω   -121.00 -27.00   0.50    0.05    --  -48.69 -77.00 150.00  188
 75  ω   -121.00 -35.00   0.50    0.05    --  -48.69 -57.00-150.00  172
 76  ω     27.00 121.00   0.50    0.05    --   48.69  77.00  30.00  188
 77  ω     27.00 121.00   0.50    0.05    --   48.69  77.00  90.00  188
 78  ω     27.00 121.00   0.50    0.05    --   48.69  77.00 -60.00  188
;
_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      -0.2120654000
_diffrn_orient_matrix_UB_12      -0.0088434000
_diffrn_orient_matrix_UB_13      0.0401265000
_diffrn_orient_matrix_UB_21      0.0435578000
_diffrn_orient_matrix_UB_22      -0.0692048000
_diffrn_orient_matrix_UB_23      0.0284741000
_diffrn_orient_matrix_UB_31      0.0630158000
_diffrn_orient_matrix_UB_32      0.0181607000
_diffrn_orient_matrix_UB_33      0.1283242000
_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         0.758
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                3069
_reflns_number_total             3079
_reflns_odcompleteness_completeness 93.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.5813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0661
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3A-C4 \\sim C4-O3
 with sigma of 0.02
 O3A-O2 \\sim O2-O3
 with sigma of 0.02
 O5-O6 \\sim O6-O5A
 with sigma of 0.02
 O5-C4 \\sim C4-O5A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O3A) = Uanis(O3)
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(O3A)=Sof(O5A)=1-FVAR(1)
 Sof(O3)=Sof(O5)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C22(H22A,H22B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.50918(19) 0.76106(6) 0.31587(12) 0.0219(3) Uani 1 1 d D . . . .
O3 O 0.6931(9) 0.7715(4) 0.3863(5) 0.0258(11) Uani 0.640(18) 1 d D . P A 1
O3A O 0.6688(17) 0.7878(5) 0.3945(10) 0.0258(11) Uani 0.360(18) 1 d D . P A 2
O5 O 0.4907(9) 0.8079(4) 0.5357(7) 0.0230(11) Uani 0.640(18) 1 d D . P A 1
O5A O 0.4718(16) 0.7952(5) 0.5569(11) 0.0230(11) Uani 0.360(18) 1 d D . P A 2
O6 O 0.30833(18) 0.78166(6) 0.47596(12) 0.0203(3) Uani 1 1 d D . . . .
O17 O 0.4441(2) 0.42286(7) 0.89206(14) 0.0347(4) Uani 1 1 d . . . . .
O18 O 0.4290(2) 0.37015(6) 0.72734(13) 0.0263(3) Uani 1 1 d . . . . .
O20 O 0.6754(2) 0.60834(7) 0.36005(13) 0.0308(3) Uani 1 1 d . . . . .
O21 O 0.3676(2) 0.61109(6) 0.28632(12) 0.0250(3) Uani 1 1 d . . . . .
N16 N 0.4252(2) 0.41925(7) 0.78352(14) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.3597(3) 0.73646(8) 0.38823(16) 0.0181(4) Uani 1 1 d . . . . .
C4 C 0.6471(3) 0.76712(8) 0.51159(16) 0.0188(3) Uani 1 1 d D . . . .
C7 C 0.4375(2) 0.67656(8) 0.45243(15) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.6082(3) 0.69888(8) 0.53417(18) 0.0249(4) Uani 1 1 d . . . . .
H8A H 0.574958 0.692620 0.618735 0.030 Uiso 1 1 calc R U . . .
H8B H 0.726999 0.674093 0.518066 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2711(3) 0.64659(8) 0.52450(16) 0.0202(4) Uani 1 1 d . . . . .
H9A H 0.224523 0.677816 0.582484 0.024 Uiso 1 1 calc R U . . .
H9B H 0.160358 0.636922 0.468845 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3266(2) 0.58750(8) 0.59156(15) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.3866(2) 0.58927(8) 0.71155(15) 0.0188(4) Uani 1 1 d . . . . .
H11 H 0.403895 0.628515 0.750221 0.023 Uiso 1 1 calc R U . . .
C12 C 0.4213(2) 0.53440(8) 0.77509(16) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.460915 0.535636 0.856908 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3966(2) 0.47786(8) 0.71622(16) 0.0176(4) Uani 1 1 d . . . . .
C14 C 0.3429(2) 0.47416(7) 0.59687(16) 0.0178(3) Uani 1 1 d . . . . .
H14 H 0.330743 0.434785 0.558013 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3073(2) 0.52944(8) 0.53515(17) 0.0181(3) Uani 1 1 d . . . . .
H15 H 0.269065 0.527784 0.453131 0.022 Uiso 1 1 calc R U . . .
C19 C 0.5113(3) 0.62878(8) 0.36161(16) 0.0197(3) Uani 1 1 d . . . . .
C22 C 0.4163(4) 0.56351(10) 0.19889(18) 0.0376(5) Uani 1 1 d . . . . .
H22A H 0.432761 0.522291 0.238234 0.045 Uiso 1 1 calc R U . . .
H22B H 0.539951 0.574408 0.159868 0.045 Uiso 1 1 calc R U . . .
C23 C 0.2512(4) 0.56115(11) 0.10856(19) 0.0410(6) Uani 1 1 d . . . . .
H23A H 0.250794 0.599535 0.060713 0.062 Uiso 1 1 calc R U . . .
H23B H 0.126872 0.557493 0.149533 0.062 Uiso 1 1 calc R U . . .
H23C H 0.267901 0.524873 0.056317 0.062 Uiso 1 1 calc R U . . .
C24 C 0.1802(3) 0.73252(8) 0.30703(19) 0.0248(4) Uani 1 1 d . . . . .
H24A H 0.078025 0.708697 0.346628 0.037 Uiso 1 1 calc R U . . .
H24B H 0.213794 0.711483 0.232649 0.037 Uiso 1 1 calc R U . . .
H24C H 0.132327 0.774812 0.289155 0.037 Uiso 1 1 calc R U . . .
C25 C 0.8196(3) 0.79408(10) 0.5807(2) 0.0302(4) Uani 1 1 d . . . . .
H25A H 0.833063 0.838574 0.561406 0.045 Uiso 1 1 calc R U . . .
H25B H 0.938963 0.771799 0.559337 0.045 Uiso 1 1 calc R U . . .
H25C H 0.798865 0.789370 0.666432 0.045 Uiso 1 1 calc R U . . .


_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
O2 O3 1.484(6) . ?
O2 O3A 1.498(12) . ?
O2 C1 1.422(2) . ?
O3 C4 1.450(6) . ?
O3A C4 1.397(12) . ?
O5 O6 1.508(6) . ?
O5 C4 1.412(6) . ?
O5A O6 1.450(12) . ?
O5A C4 1.445(12) . ?
O6 C1 1.429(2) . ?
O17 N16 1.223(2) . ?
O18 N16 1.224(2) . ?
O20 C19 1.205(2) . ?
O21 C19 1.333(2) . ?
O21 C22 1.457(2) . ?
N16 C13 1.472(2) . ?
C1 C7 1.555(2) . ?
C1 C24 1.511(3) . ?
C4 C8 1.505(2) . ?
C4 C25 1.508(3) . ?
C7 C8 1.541(3) . ?
C7 C9 1.551(2) . ?
C7 C19 1.536(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(2) . ?
C10 C11 1.396(2) . ?
C10 C15 1.397(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 C14 1.380(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.497(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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 O2 O3 111.3(3) . . ?
C1 O2 O3A 109.2(5) . . ?
C4 O3 O2 107.7(4) . . ?
C4 O3A O2 109.8(8) . . ?
C4 O5 O6 107.9(4) . . ?
C4 O5A O6 109.3(8) . . ?
C1 O6 O5 110.0(3) . . ?
C1 O6 O5A 111.5(5) . . ?
C19 O21 C22 116.50(16) . . ?
O17 N16 O18 124.25(15) . . ?
O17 N16 C13 117.76(15) . . ?
O18 N16 C13 117.99(14) . . ?
O2 C1 O6 109.66(13) . . ?
O2 C1 C7 109.03(13) . . ?
O2 C1 C24 105.15(14) . . ?
O6 C1 C7 108.95(13) . . ?
O6 C1 C24 104.00(14) . . ?
C24 C1 C7 119.69(14) . . ?
O3 C4 C8 105.6(4) . . ?
O3 C4 C25 106.7(3) . . ?
O3A C4 O5A 108.0(6) . . ?
O3A C4 C8 119.3(5) . . ?
O3A C4 C25 105.1(5) . . ?
O5 C4 O3 109.2(3) . . ?
O5 C4 C8 115.4(4) . . ?
O5 C4 C25 104.6(3) . . ?
O5A C4 C8 101.0(4) . . ?
O5A C4 C25 107.8(5) . . ?
C8 C4 C25 115.01(16) . . ?
C8 C7 C1 105.37(14) . . ?
C8 C7 C9 111.88(15) . . ?
C9 C7 C1 109.53(13) . . ?
C19 C7 C1 110.75(13) . . ?
C19 C7 C8 110.06(15) . . ?
C19 C7 C9 109.22(14) . . ?
C4 C8 C7 109.54(15) . . ?
C4 C8 H8A 109.8 . . ?
C4 C8 H8B 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C7 C9 H9A 108.5 . . ?
C7 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C7 115.18(14) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C11 C10 C9 121.31(16) . . ?
C11 C10 C15 118.81(16) . . ?
C15 C10 C9 119.77(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.87(16) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.35(16) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 N16 119.00(15) . . ?
C14 C13 N16 118.46(16) . . ?
C14 C13 C12 122.54(16) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.27(16) . . ?
C15 C14 H14 120.9 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.13(17) . . ?
C14 C15 H15 119.4 . . ?
O20 C19 O21 124.00(17) . . ?
O20 C19 C7 124.94(18) . . ?
O21 C19 C7 111.02(14) . . ?
O21 C22 H22A 110.3 . . ?
O21 C22 H22B 110.3 . . ?
O21 C22 C23 107.28(19) . . ?
H22A C22 H22B 108.5 . . ?
C23 C22 H22A 110.3 . . ?
C23 C22 H22B 110.3 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 C24 H24A 109.5 . . ?
C1 C24 H24B 109.5 . . ?
C1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C25 H25A 109.5 . . ?
C4 C25 H25B 109.5 . . ?
C4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
O2 O3 C4 O5 -53.1(5) . . . . ?
O2 O3 C4 C8 71.6(5) . . . . ?
O2 O3 C4 C25 -165.6(4) . . . . ?
O2 O3A C4 O5A -67.9(8) . . . . ?
O2 O3A C4 C8 46.4(8) . . . . ?
O2 O3A C4 C25 177.3(5) . . . . ?
O2 C1 C7 C8 63.54(17) . . . . ?
O2 C1 C7 C9 -175.96(14) . . . . ?
O2 C1 C7 C19 -55.44(18) . . . . ?
O3 O2 C1 O6 65.0(4) . . . . ?
O3 O2 C1 C7 -54.2(4) . . . . ?
O3 O2 C1 C24 176.3(4) . . . . ?
O3 C4 C8 C7 -59.1(3) . . . . ?
O3A O2 C1 O6 48.8(5) . . . . ?
O3A O2 C1 C7 -70.4(5) . . . . ?
O3A O2 C1 C24 160.1(4) . . . . ?
O3A C4 C8 C7 -50.1(6) . . . . ?
O5 O6 C1 O2 -47.5(4) . . . . ?
O5 O6 C1 C7 71.7(4) . . . . ?
O5 O6 C1 C24 -159.6(4) . . . . ?
O5 C4 C8 C7 61.7(4) . . . . ?
O5A O6 C1 O2 -63.3(5) . . . . ?
O5A O6 C1 C7 55.9(5) . . . . ?
O5A O6 C1 C24 -175.4(5) . . . . ?
O5A C4 C8 C7 67.9(5) . . . . ?
O6 O5 C4 O3 69.9(5) . . . . ?
O6 O5 C4 C8 -48.9(6) . . . . ?
O6 O5 C4 C25 -176.3(4) . . . . ?
O6 O5A C4 O3A 54.0(8) . . . . ?
O6 O5A C4 C8 -71.9(6) . . . . ?
O6 O5A C4 C25 167.1(5) . . . . ?
O6 C1 C7 C8 -56.10(17) . . . . ?
O6 C1 C7 C9 64.39(17) . . . . ?
O6 C1 C7 C19 -175.08(14) . . . . ?
O17 N16 C13 C12 9.5(2) . . . . ?
O17 N16 C13 C14 -169.45(16) . . . . ?
O18 N16 C13 C12 -170.28(15) . . . . ?
O18 N16 C13 C14 10.7(2) . . . . ?
N16 C13 C14 C15 177.05(14) . . . . ?
C1 O2 O3 C4 -13.2(7) . . . . ?
C1 O2 O3A C4 14.6(8) . . . . ?
C1 C7 C8 C4 -5.80(19) . . . . ?
C1 C7 C9 C10 179.85(14) . . . . ?
C1 C7 C19 O20 121.10(19) . . . . ?
C1 C7 C19 O21 -60.92(18) . . . . ?
C4 O5 O6 C1 -17.0(6) . . . . ?
C4 O5A O6 C1 10.0(8) . . . . ?
C7 C9 C10 C11 95.12(19) . . . . ?
C7 C9 C10 C15 -88.6(2) . . . . ?
C8 C7 C9 C10 -63.70(19) . . . . ?
C8 C7 C19 O20 5.0(2) . . . . ?
C8 C7 C19 O21 -177.03(14) . . . . ?
C9 C7 C8 C4 -124.74(16) . . . . ?
C9 C7 C19 O20 -118.20(19) . . . . ?
C9 C7 C19 O21 59.78(18) . . . . ?
C9 C10 C11 C12 174.47(15) . . . . ?
C9 C10 C15 C14 -175.10(15) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C10 C15 C14 1.2(2) . . . . ?
C11 C12 C13 N16 -177.60(14) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C12 C13 C14 C15 -1.9(2) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C15 C10 C11 C12 -1.8(2) . . . . ?
C19 O21 C22 C23 -167.79(16) . . . . ?
C19 C7 C8 C4 113.64(17) . . . . ?
C19 C7 C9 C10 58.4(2) . . . . ?
C22 O21 C19 O20 0.8(3) . . . . ?
C22 O21 C19 C7 -177.21(15) . . . . ?
C24 C1 C7 C8 -175.46(15) . . . . ?
C24 C1 C7 C9 -55.0(2) . . . . ?
C24 C1 C7 C19 65.6(2) . . . . ?
C25 C4 C8 C7 -176.43(15) . . . . ?

_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 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.615
####################################################################### 
# 
# 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_bl-1578
_database_code_depnum_ccdc_archive 'CCDC 2476575'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2024-02-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 Br O7'
_chemical_formula_sum            'C16 H21 Br O7'
_chemical_formula_weight         405.24
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     BL-1578
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'
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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   36.0080(3)
_cell_length_b                   36.0080(3)
_cell_length_c                   7.27389(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8167.62(14)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    17417
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.2190
_cell_measurement_theta_min      4.2480
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    3.390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            24685
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.594
_diffrn_reflns_theta_min         6.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  35.00   0.50    0.50    --  -44.25  19.00-114.00  124
  2  ω     47.00 110.00   0.50    0.50    --   44.25-149.00  69.00  126
  3  ω   -166.00 -79.00   0.50    2.00    --  -96.00-116.00 -10.00  174
  4  ω     48.00 109.00   0.50    2.00    --  117.50-116.00-113.00  122
  5  ω     68.00 152.00   0.50    2.00    --  117.50 168.00 120.00  168
  6  ω    -51.00 -21.00   0.50    2.00    --  -96.00  45.00-180.00   60
  7  ω     97.00 178.00   0.50    2.00    --  117.50  61.00 -90.00  162
  8  ω     45.00 105.00   0.50    2.00    --  117.50 -95.00  30.00  120
  9  ω     45.00 105.00   0.50    2.00    --  117.50 -95.00 -30.00  120
 10  ω     45.00 105.00   0.50    2.00    --  117.50 -77.00 120.00  120
 11  ω     45.00  71.00   0.50    2.00    --  117.50 -61.00  60.00   52
 12  ω     45.00 105.00   0.50    2.00    --  117.50 -95.00-120.00  120
 13  ω     97.00 178.00   0.50    2.00    --  117.50  61.00-180.00  162
 14  ω     97.00 178.00   0.50    2.00    --  117.50  61.00-180.00  162
 15  ω     45.00  71.00   0.50    2.00    --  117.50 -61.00-180.00   52
 16  ω     45.00  71.00   0.50    2.00    --  117.50 -61.00-150.00   52
 17  ω     95.00 178.00   0.50    2.00    --  117.50 125.00 -60.00  166
 18  ω     47.00 111.00   0.50    2.00    --  117.50-125.00 150.00  128
 19  ω     86.00 178.00   0.50    2.00    --  117.50  15.00-180.00  184
 20  ω    101.00 178.00   0.50    2.00    --  117.50 116.00 -24.00  154
 21  ω     45.00 105.00   0.50    2.00    --  117.50 -77.00  60.00  120
 22  ω     45.00 105.00   0.50    2.00    --  117.50 -77.00 150.00  120
 23  ω     45.00  96.00   0.50    2.00    --  117.50 -95.00-150.00  102
 24  ω    141.00 167.00   0.50    2.00    --  117.50  45.00 -90.00   52
 25  ω    105.00 156.00   0.50    2.00    --  117.50  30.00  90.00  102
;
_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      0.0425672000
_diffrn_orient_matrix_UB_12      0.0405854000
_diffrn_orient_matrix_UB_13      0.0491149000
_diffrn_orient_matrix_UB_21      -0.0220354000
_diffrn_orient_matrix_UB_22      0.0271373000
_diffrn_orient_matrix_UB_23      -0.0163917000
_diffrn_orient_matrix_UB_31      -0.0119420000
_diffrn_orient_matrix_UB_32      -0.0075534000
_diffrn_orient_matrix_UB_33      0.2053612000
_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                3713
_reflns_number_total             3941
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.000049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.063
_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)+(0.0292P)²+10.3091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0703
_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    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.31697(2) 0.55196(2) 0.34748(2) 0.04369(9) Uani 1 1 d . . . . .
O1 O 0.40707(3) 0.41049(3) 1.00521(11) 0.01895(18) Uani 1 1 d . . . . .
O2 O 0.37342(3) 0.39838(3) 0.72181(12) 0.01794(18) Uani 1 1 d . . . . .
O3 O 0.35886(3) 0.35258(3) 0.73583(12) 0.01995(18) Uani 1 1 d . . . . .
H3 H 0.3432(7) 0.3460(7) 0.839(3) 0.037(5) Uiso 1 1 d . . . . .
O4 O 0.45895(3) 0.47163(3) 1.15753(12) 0.02063(19) Uani 1 1 d . . . . .
O5 O 0.47167(3) 0.44589(3) 1.26882(13) 0.0244(2) Uani 1 1 d . . . . .
H5 H 0.4883(8) 0.4432(7) 1.191(3) 0.040(6) Uiso 1 1 d . . . . .
O6 O 0.46356(3) 0.55102(3) 0.96844(13) 0.02181(19) Uani 1 1 d . . . . .
O7 O 0.41629(3) 0.52782(3) 1.20268(13) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.40710(4) 0.47604(4) 0.98262(16) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.42437(4) 0.46846(4) 0.80224(16) 0.0177(2) Uani 1 1 d . . . . .
H2A H 0.410048 0.472780 0.694908 0.021 Uiso 1 1 calc R U . . .
H2B H 0.455694 0.488079 0.791823 0.021 Uiso 1 1 calc R U . . .
C3 C 0.41385(4) 0.42188(4) 0.81468(16) 0.0172(2) Uani 1 1 d . . . . .
C4 C 0.44761(4) 0.41326(4) 0.73756(18) 0.0218(2) Uani 1 1 d . . . . .
H4A H 0.475227 0.432358 0.796316 0.033 Uiso 1 1 calc R U . . .
H4B H 0.450065 0.418441 0.604679 0.033 Uiso 1 1 calc R U . . .
H4C H 0.439531 0.383363 0.761483 0.033 Uiso 1 1 calc R U . . .
C5 C 0.41422(4) 0.44579(4) 1.11476(16) 0.0180(2) Uani 1 1 d . . . . .
C6 C 0.38724(4) 0.42949(4) 1.28692(17) 0.0219(3) Uani 1 1 d . . . . .
H6A H 0.392094 0.453849 1.363904 0.033 Uiso 1 1 calc R U . . .
H6B H 0.395281 0.411118 1.355332 0.033 Uiso 1 1 calc R U . . .
H6C H 0.356861 0.412924 1.253104 0.033 Uiso 1 1 calc R U . . .
C7 C 0.43283(4) 0.52264(4) 1.04668(16) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.43868(4) 0.56892(4) 1.29830(18) 0.0231(3) Uani 1 1 d . . . . .
H8A H 0.420855 0.582760 1.299017 0.028 Uiso 1 1 calc R U . . .
H8B H 0.466077 0.588273 1.235523 0.028 Uiso 1 1 calc R U . . .
C9 C 0.44706(5) 0.56039(4) 1.49191(18) 0.0266(3) Uani 1 1 d . . . . .
H9A H 0.465668 0.547774 1.489770 0.040 Uiso 1 1 calc R U . . .
H9B H 0.419816 0.540457 1.551367 0.040 Uiso 1 1 calc R U . . .
H9C H 0.461148 0.587398 1.560768 0.040 Uiso 1 1 calc R U . . .
C10 C 0.35862(4) 0.46121(4) 0.97072(17) 0.0196(2) Uani 1 1 d . . . . .
H10A H 0.342398 0.429880 0.948999 0.024 Uiso 1 1 calc R U . . .
H10B H 0.349179 0.466755 1.090330 0.024 Uiso 1 1 calc R U . . .
C11 C 0.34765(4) 0.48322(4) 0.82082(17) 0.0206(2) Uani 1 1 d . . . . .
C12 C 0.33128(4) 0.46261(5) 0.65252(18) 0.0235(3) Uani 1 1 d . . . . .
H12 H 0.326617 0.434473 0.633970 0.028 Uiso 1 1 calc R U . . .
C13 C 0.32175(4) 0.48273(5) 0.51195(19) 0.0273(3) Uani 1 1 d . . . . .
H13 H 0.310652 0.468568 0.398036 0.033 Uiso 1 1 calc R U . . .
C14 C 0.32867(5) 0.52357(5) 0.5408(2) 0.0297(3) Uani 1 1 d . . . . .
C15 C 0.34408(5) 0.54472(5) 0.7067(2) 0.0314(3) Uani 1 1 d . . . . .
H15 H 0.348202 0.572665 0.724727 0.038 Uiso 1 1 calc R U . . .
C16 C 0.35340(5) 0.52421(5) 0.84657(19) 0.0260(3) Uani 1 1 d . . . . .
H16 H 0.363817 0.538308 0.961134 0.031 Uiso 1 1 calc R U . . .


_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 C14 1.9052(15) . ?
O1 C3 1.4312(14) . ?
O1 C5 1.4104(15) . ?
O2 O3 1.4634(12) . ?
O2 C3 1.4353(14) . ?
O3 H3 0.89(2) . ?
O4 O5 1.4655(13) . ?
O4 C5 1.4348(15) . ?
O5 H5 0.86(3) . ?
O6 C7 1.2092(16) . ?
O7 C7 1.3372(15) . ?
O7 C8 1.4598(15) . ?
C1 C2 1.5339(16) . ?
C1 C5 1.5670(17) . ?
C1 C7 1.5283(17) . ?
C1 C10 1.5518(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5262(17) . ?
C3 C4 1.5054(17) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.5120(16) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5037(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5118(18) . ?
C11 C12 1.3997(18) . ?
C11 C16 1.397(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(2) . ?
C16 H16 0.9500 . ?

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
C5 O1 C3 111.15(9) . . ?
C3 O2 O3 108.52(8) . . ?
O2 O3 H3 100.3(14) . . ?
C5 O4 O5 108.30(9) . . ?
O4 O5 H5 99.3(15) . . ?
C7 O7 C8 119.16(10) . . ?
C2 C1 C5 100.31(10) . . ?
C2 C1 C10 112.18(10) . . ?
C7 C1 C2 112.28(10) . . ?
C7 C1 C5 110.86(10) . . ?
C7 C1 C10 110.79(10) . . ?
C10 C1 C5 109.99(10) . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.19(9) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
O1 C3 O2 108.02(9) . . ?
O1 C3 C2 106.57(9) . . ?
O1 C3 C4 109.97(10) . . ?
O2 C3 C2 103.95(10) . . ?
O2 C3 C4 112.88(10) . . ?
C4 C3 C2 114.97(10) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 O4 110.29(10) . . ?
O1 C5 C1 105.09(9) . . ?
O1 C5 C6 109.01(10) . . ?
O4 C5 C1 101.71(9) . . ?
O4 C5 C6 111.54(10) . . ?
C6 C5 C1 118.77(11) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O6 C7 O7 124.37(11) . . ?
O6 C7 C1 125.50(11) . . ?
O7 C7 C1 110.13(10) . . ?
O7 C8 H8A 110.2 . . ?
O7 C8 H8B 110.2 . . ?
O7 C8 C9 107.74(11) . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 108.8 . . ?
C1 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C1 113.80(10) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 120.27(12) . . ?
C16 C11 C10 121.17(11) . . ?
C16 C11 C12 118.56(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.97(13) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.90(13) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 Br1 119.29(11) . . ?
C13 C14 C15 121.82(14) . . ?
C15 C14 Br1 118.88(12) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.75(14) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.97(13) . . ?
C15 C16 H16 119.5 . . ?

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
O3 H3 O3 0.89(2) 1.93(2) 2.8184(8) 173(2) 5 yes
O5 H5 O6 0.86(3) 2.01(3) 2.8585(14) 168(2) 10_667 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 C14 C15 C16 -178.76(11) . . . . ?
O3 O2 C3 O1 -63.51(11) . . . . ?
O3 O2 C3 C2 -176.45(8) . . . . ?
O3 O2 C3 C4 58.31(12) . . . . ?
O5 O4 C5 O1 -63.84(11) . . . . ?
O5 O4 C5 C1 -174.94(9) . . . . ?
O5 O4 C5 C6 57.45(12) . . . . ?
C1 C2 C3 O1 -19.94(12) . . . . ?
C1 C2 C3 O2 94.04(10) . . . . ?
C1 C2 C3 C4 -142.06(10) . . . . ?
C1 C10 C11 C12 99.53(14) . . . . ?
C1 C10 C11 C16 -80.68(15) . . . . ?
C2 C1 C5 O1 -34.51(11) . . . . ?
C2 C1 C5 O4 80.50(10) . . . . ?
C2 C1 C5 C6 -156.71(10) . . . . ?
C2 C1 C7 O6 -0.44(18) . . . . ?
C2 C1 C7 O7 179.19(10) . . . . ?
C2 C1 C10 C11 -58.66(14) . . . . ?
C3 O1 C5 O4 -84.98(11) . . . . ?
C3 O1 C5 C1 23.91(12) . . . . ?
C3 O1 C5 C6 152.23(10) . . . . ?
C5 O1 C3 O2 -113.93(10) . . . . ?
C5 O1 C3 C2 -2.75(13) . . . . ?
C5 O1 C3 C4 122.48(11) . . . . ?
C5 C1 C2 C3 32.19(11) . . . . ?
C5 C1 C7 O6 110.86(14) . . . . ?
C5 C1 C7 O7 -69.52(13) . . . . ?
C5 C1 C10 C11 -169.40(10) . . . . ?
C7 O7 C8 C9 -124.32(12) . . . . ?
C7 C1 C2 C3 149.94(10) . . . . ?
C7 C1 C5 O1 -153.31(10) . . . . ?
C7 C1 C5 O4 -38.30(12) . . . . ?
C7 C1 C5 C6 84.49(13) . . . . ?
C7 C1 C10 C11 67.69(13) . . . . ?
C8 O7 C7 O6 -6.73(19) . . . . ?
C8 O7 C7 C1 173.64(11) . . . . ?
C10 C1 C2 C3 -84.52(12) . . . . ?
C10 C1 C5 O1 83.82(11) . . . . ?
C10 C1 C5 O4 -161.17(9) . . . . ?
C10 C1 C5 C6 -38.38(14) . . . . ?
C10 C1 C7 O6 -126.73(13) . . . . ?
C10 C1 C7 O7 52.89(13) . . . . ?
C10 C11 C12 C13 -178.85(12) . . . . ?
C10 C11 C16 C15 178.67(13) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C11 C16 C15 -1.5(2) . . . . ?
C12 C13 C14 Br1 178.58(10) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C16 C11 C12 C13 1.36(19) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.484 182.7 44.5 ?
2 0.333 0.667 -0.104 182.7 44.5 ?
3 0.667 0.333 -0.437 182.7 44.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.431
####################################################################### 
# 
# 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_BL-1529-1
_database_code_depnum_ccdc_archive 'CCDC 2476599'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2024-02-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O7'
_chemical_formula_sum            'C16 H19 N O7'
_chemical_formula_weight         337.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19NO7
_chemical_oxdiff_usercomment     BL-1529.1
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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.81567(11)
_cell_length_b                   8.70518(17)
_cell_length_c                   12.2530(3)
_cell_angle_alpha                77.6093(19)
_cell_angle_beta                 89.4484(15)
_cell_angle_gamma                78.8430(14)
_cell_volume                     798.41(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14634
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.0600
_cell_measurement_theta_min      3.6910
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.1225
0 1 1 0.0655
0 0 1 0.0532
0 0 -1 0.0722
-1 0 0 0.1084
1 0 0 0.0831
0 1 -1 0.0747
0 -1 1 0.0728

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.9999 -1.0007 -0.1333 -0.1244 -0.0848
0.0000 0.9999 1.0007 0.1333 0.1244 0.0848
-0.0001 -0.0002 1.0000 0.1190 -0.0465 0.0160
0.0001 0.0002 -1.0000 -0.1190 0.0465 -0.0160
-0.9999 0.0002 -0.0001 -0.0454 -0.0314 0.1933
0.9999 -0.0002 0.0001 0.0454 0.0314 -0.1933
0.0002 1.0003 -0.9993 -0.1048 0.2174 0.0529
-0.0002 -1.0003 0.9993 0.1048 -0.2174 -0.0529

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21228
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.712
_diffrn_reflns_theta_min         3.695
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  26.00   0.50    0.05    --  -48.13  19.00 120.00  106
  2  ω   -107.00 -29.00   0.50    0.05    --  -48.13 156.00  -3.00  156
  3  ω    -84.00  -9.00   0.50    0.05    --  -48.13 120.00-159.00  150
  4  ω    -84.00 -21.00   0.50    0.14    --  -90.00 120.00-159.00  126
  5  ω    -43.00  24.00   0.50    0.05    --  -48.13  38.00 -30.00  134
  6  ω     50.00 113.00   0.50    0.05    --   48.13-156.00 -39.00  126
  7  ω     42.00 111.00   0.50    0.14    --  111.50-125.00-120.00  138
  8  ω     50.00 133.00   0.50    0.14    --  111.50-156.00 -39.00  166
  9  ω     42.00 111.00   0.50    0.14    --  111.50-125.00  30.00  138
 10  ω     42.00 111.00   0.50    0.14    --  111.50-125.00  90.00  138
 11  ω     42.00 111.00   0.50    0.14    --  111.50-125.00  60.00  138
 12  ω     85.00 111.00   0.50    0.14    --  111.50-125.00   0.00   52
 13  ω     60.00 111.00   0.50    0.14    --  111.50-125.00 -30.00  102
 14  ω     76.00 111.00   0.50    0.14    --  111.50-125.00-180.00   70
 15  ω     70.00 106.00   0.50    0.14    --  111.50-125.00-150.00   72
 16  ω     41.00  93.00   0.50    0.14    --  111.50 -95.00   0.00  104
 17  ω     47.00  83.00   0.50    0.14    --  111.50 -95.00 -30.00   72
 18  ω     75.00 101.00   0.50    0.14    --  111.50 -95.00 -90.00   52
 19  ω     75.00 101.00   0.50    0.14    --  111.50 -95.00  60.00   52
 20  ω     42.00 110.00   0.50    0.14    --  111.50-120.00 116.00  136
 21  ω     79.00 105.00   0.50    0.14    --  111.50 -95.00 150.00   52
 22  ω     79.00 111.00   0.50    0.14    --  111.50-125.00 150.00   64
 23  ω     31.00  90.00   0.50    0.05    --   48.13-120.00 116.00  118
 24  ω     40.00 137.00   0.50    0.14    --  111.50 -85.00  78.25  194
 25  ω     40.00 137.00   0.50    0.14    --  111.50 -85.00  78.25  194
 26  ω     40.00 135.00   0.50    0.14    --  111.50 -81.00  46.31  190
 27  ω     92.00 129.00   0.50    0.14    --  111.50 -81.00  46.31   74
 28  ω     40.00 105.00   0.50    0.14    --  111.50 -95.00 -60.00  130
 29  ω     40.00 104.00   0.50    0.14    --  111.50 -95.00-120.00  128
 30  ω     40.00 105.00   0.50    0.14    --  111.50 -77.00-120.00  130
 31  ω     40.00  71.00   0.50    0.14    --  111.50 -61.00-120.00   62
 32  ω     40.00 105.00   0.50    0.14    --  111.50 -77.00-180.00  130
 33  ω     43.00  68.00   0.50    0.14    --  111.50 -61.00 -60.00   50
 34  ω     40.00  71.00   0.50    0.14    --  111.50 -61.00   0.00   62
 35  ω     40.00 105.00   0.50    0.14    --  111.50 -77.00  30.00  130
 36  ω     40.00 105.00   0.50    0.14    --  111.50 -77.00  90.00  130
 37  ω     40.00  71.00   0.50    0.14    --  111.50 -61.00 120.00   62
 38  ω     67.00 103.00   0.50    0.14    --  111.50 -77.00 150.00   72
 39  ω     40.00  70.00   0.50    0.14    --  111.50 -61.00  90.00   60
 40  ω     44.00  69.00   0.50    0.14    --  111.50 -61.00 -30.00   50
 41  ω     98.00 178.00   0.50    0.14    --  111.50 120.00-159.00  160
 42  ω     74.00 120.00   0.50    0.05    --   48.13 156.00  -3.00   92
 43  ω     74.00 161.00   0.50    0.14    --  111.50 156.00  -3.00  174
 44  ω    120.00 171.00   0.50    0.14    --  111.50 125.00 -30.00  102
 45  ω    120.00 148.00   0.50    0.14    --  111.50 125.00   0.00   56
 46  ω    128.00 164.00   0.50    0.14    --  111.50  77.00  30.00   72
 47  ω     96.00 178.00   0.50    0.14    --  111.50  61.00  60.00  164
 48  ω    101.00 178.00   0.50    0.14    --  111.50  45.00  90.00  154
 49  ω    101.00 178.00   0.50    0.14    --  111.50  30.00 120.00  154
 50  ω    101.00 126.00   0.50    0.14    --  111.50  61.00   0.00   50
 51  ω    108.00 134.00   0.50    0.14    --  111.50  45.00-150.00   52
 52  ω    101.00 178.00   0.50    0.14    --  111.50  30.00-180.00  154
 53  ω    112.00 138.00   0.50    0.14    --  111.50  30.00-180.00   52
 54  ω    101.00 178.00   0.50    0.14    --  111.50  45.00-120.00  154
 55  ω    101.00 178.00   0.50    0.14    --  111.50  30.00 -60.00  154
 56  ω    101.00 178.00   0.50    0.14    --  111.50  30.00 -30.00  154
 57  ω    101.00 178.00   0.50    0.14    --  111.50  30.00 -30.00  154
 58  ω    101.00 178.00   0.50    0.14    --  111.50  15.00  30.00  154
 59  ω    142.00 168.00   0.50    0.14    --  111.50  15.00 150.00   52
 60  ω    101.00 141.00   0.50    0.14    --  111.50  30.00 150.00   80
 61  ω    101.00 143.00   0.50    0.14    --  111.50  30.00  60.00   84
 62  ω    133.00 163.00   0.50    0.14    --  111.50   0.00 -60.00   60
 63  ω     76.00 102.00   0.50    0.14    --  111.50   0.00 -60.00   52
 64  ω   -119.00 -38.00   0.50    0.05    --  -48.13 -43.00 177.74  162
 65  ω   -159.00 -77.00   0.50    0.14    --  -90.00-120.00 116.00  164
 66  ω   -119.00 -52.00   0.50    0.05    --  -48.13-156.00 -39.00  134
 67  ω   -144.00 -52.00   0.50    0.14    --  -90.00-156.00 -39.00  184
 68  ω   -119.00 -26.00   0.50    0.05    --  -48.13 -77.00   0.00  186
;
_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      0.0454282000
_diffrn_orient_matrix_UB_12      0.0141441000
_diffrn_orient_matrix_UB_13      0.1190572000
_diffrn_orient_matrix_UB_21      0.0314726000
_diffrn_orient_matrix_UB_22      0.1708961000
_diffrn_orient_matrix_UB_23      -0.0464742000
_diffrn_orient_matrix_UB_31      -0.1932742000
_diffrn_orient_matrix_UB_32      0.0688216000
_diffrn_orient_matrix_UB_33      0.0159575000
_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                3335
_reflns_number_total             3442
_reflns_odcompleteness_completeness 98.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.4424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.93124(12) -0.04737(11) 0.22552(8) 0.0248(2) Uani 1 1 d . . . . .
O2 O 0.95145(12) 0.11082(11) 0.24520(8) 0.0242(2) Uani 1 1 d . . . . .
O4 O 0.81305(12) 0.14668(11) 0.08066(7) 0.0223(2) Uani 1 1 d . . . . .
O16 O -0.00353(14) 0.39817(12) 0.65125(9) 0.0324(2) Uani 1 1 d . . . . .
O17 O -0.11890(13) 0.25881(16) 0.55705(9) 0.0399(3) Uani 1 1 d . . . . .
O18 O 0.40182(14) 0.32322(12) 0.09047(8) 0.0305(2) Uani 1 1 d . . . . .
O19 O 0.47883(11) 0.47076(10) 0.20400(7) 0.01970(19) Uani 1 1 d . . . . .
N15 N 0.00438(14) 0.31366(14) 0.58265(9) 0.0261(2) Uani 1 1 d . . . . .
C23 C 0.86944(19) 0.38072(16) 0.14290(12) 0.0267(3) Uani 1 1 d . . . . .
H23A H 0.985769 0.367993 0.111413 0.040 Uiso 1 1 calc R U . . .
H23B H 0.871913 0.424130 0.210213 0.040 Uiso 1 1 calc R U . . .
H23C H 0.785484 0.454554 0.087658 0.040 Uiso 1 1 calc R U . . .
C3 C 0.81594(16) 0.22033(15) 0.17268(10) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.78782(17) -0.00443(15) 0.14398(11) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.61997(16) 0.03912(14) 0.20466(10) 0.0209(3) Uani 1 1 d . . . . .
H6A H 0.614428 -0.041202 0.274660 0.025 Uiso 1 1 calc R U . . .
H6B H 0.515585 0.049115 0.156579 0.025 Uiso 1 1 calc R U . . .
C7 C 0.63678(16) 0.20330(14) 0.22898(10) 0.0180(2) Uani 1 1 d . . . . .
C8 C 0.64750(16) 0.20590(15) 0.35372(10) 0.0204(2) Uani 1 1 d . . . . .
H8A H 0.722799 0.104400 0.392952 0.025 Uiso 1 1 calc R U . . .
H8B H 0.706134 0.294350 0.361397 0.025 Uiso 1 1 calc R U . . .
C9 C 0.47608(16) 0.22622(14) 0.41304(10) 0.0197(2) Uani 1 1 d . . . . .
C10 C 0.46400(16) 0.30605(15) 0.50088(11) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.563044 0.342472 0.522219 0.026 Uiso 1 1 calc R U . . .
C11 C 0.31141(17) 0.33342(15) 0.55758(11) 0.0223(3) Uani 1 1 d . . . . .
H11 H 0.304223 0.389108 0.616710 0.027 Uiso 1 1 calc R U . . .
C12 C 0.16925(16) 0.27773(15) 0.52617(10) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.17581(17) 0.19422(16) 0.44183(11) 0.0239(3) Uani 1 1 d . . . . .
H13 H 0.077255 0.155011 0.422944 0.029 Uiso 1 1 calc R U . . .
C14 C 0.33068(17) 0.16886(16) 0.38507(11) 0.0240(3) Uani 1 1 d . . . . .
H14 H 0.337602 0.111903 0.326645 0.029 Uiso 1 1 calc R U . . .
C18 C 0.49219(16) 0.33638(14) 0.16594(10) 0.0195(2) Uani 1 1 d . . . . .
C20 C 0.33963(18) 0.60302(16) 0.15171(11) 0.0264(3) Uani 1 1 d . . . . .
H20A H 0.224347 0.574861 0.169983 0.032 Uiso 1 1 calc R U . . .
H20B H 0.349547 0.625577 0.069442 0.032 Uiso 1 1 calc R U . . .
C21 C 0.35735(18) 0.74644(16) 0.19537(13) 0.0284(3) Uani 1 1 d . . . . .
H21A H 0.266271 0.837631 0.160591 0.043 Uiso 1 1 calc R U . . .
H21B H 0.472334 0.772506 0.177611 0.043 Uiso 1 1 calc R U . . .
H21C H 0.345097 0.723548 0.276615 0.043 Uiso 1 1 calc R U . . .
C22 C 0.80477(19) -0.13245(17) 0.07781(12) 0.0289(3) Uani 1 1 d . . . . .
H22A H 0.706563 -0.107269 0.023611 0.043 Uiso 1 1 calc R U . . .
H22B H 0.804340 -0.236132 0.128442 0.043 Uiso 1 1 calc R U . . .
H22C H 0.914475 -0.137661 0.038100 0.043 Uiso 1 1 calc R U . . .


_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 O2 1.4855(12) . ?
O1 C5 1.4469(15) . ?
O2 C3 1.4436(15) . ?
O4 C3 1.4139(14) . ?
O4 C5 1.4250(15) . ?
O16 N15 1.2241(16) . ?
O17 N15 1.2259(16) . ?
O18 C18 1.2068(16) . ?
O19 C18 1.3352(15) . ?
O19 C20 1.4601(15) . ?
N15 C12 1.4686(16) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C3 1.5039(17) . ?
C3 C7 1.5736(17) . ?
C5 C6 1.5255(18) . ?
C5 C22 1.4985(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5508(16) . ?
C7 C8 1.5368(16) . ?
C7 C18 1.5303(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5164(17) . ?
C9 C10 1.3943(18) . ?
C9 C14 1.3995(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3809(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3836(18) . ?
C12 C13 1.3806(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3942(19) . ?
C14 H14 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.4897(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C5 O1 O2 102.64(8) . . ?
C3 O2 O1 102.42(8) . . ?
C3 O4 C5 96.17(9) . . ?
C18 O19 C20 115.59(9) . . ?
O16 N15 O17 123.58(12) . . ?
O16 N15 C12 118.54(11) . . ?
O17 N15 C12 117.86(11) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
O2 C3 C23 107.78(10) . . ?
O2 C3 C7 107.29(9) . . ?
O4 C3 O2 102.59(9) . . ?
O4 C3 C23 113.36(10) . . ?
O4 C3 C7 103.54(9) . . ?
C23 C3 C7 120.71(11) . . ?
O1 C5 C6 107.81(10) . . ?
O1 C5 C22 108.22(10) . . ?
O4 C5 O1 102.24(9) . . ?
O4 C5 C6 103.25(10) . . ?
O4 C5 C22 113.91(11) . . ?
C22 C5 C6 119.89(11) . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
C5 C6 C7 101.89(10) . . ?
H6A C6 H6B 109.3 . . ?
C7 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
C6 C7 C3 99.01(9) . . ?
C8 C7 C3 110.82(10) . . ?
C8 C7 C6 114.67(10) . . ?
C18 C7 C3 109.28(10) . . ?
C18 C7 C6 110.40(10) . . ?
C18 C7 C8 111.88(10) . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 C7 116.56(10) . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C10 C9 C8 117.71(11) . . ?
C10 C9 C14 118.47(11) . . ?
C14 C9 C8 123.82(11) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.53(12) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.37(12) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 N15 118.42(12) . . ?
C13 C12 N15 119.17(11) . . ?
C13 C12 C11 122.38(12) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.35(12) . . ?
C14 C13 H13 120.8 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.86(12) . . ?
C13 C14 H14 119.6 . . ?
O18 C18 O19 123.74(11) . . ?
O18 C18 C7 124.68(11) . . ?
O19 C18 C7 111.58(10) . . ?
O19 C20 H20A 110.1 . . ?
O19 C20 H20B 110.1 . . ?
O19 C20 C21 107.83(11) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C22 H22A 109.5 . . ?
C5 C22 H22B 109.5 . . ?
C5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
O1 O2 C3 O4 -34.47(10) . . . . ?
O1 O2 C3 C23 -154.35(9) . . . . ?
O1 O2 C3 C7 74.24(10) . . . . ?
O1 C5 C6 C7 72.19(11) . . . . ?
O2 O1 C5 O4 33.43(11) . . . . ?
O2 O1 C5 C6 -74.99(11) . . . . ?
O2 O1 C5 C22 153.96(10) . . . . ?
O2 C3 C7 C6 -74.10(10) . . . . ?
O2 C3 C7 C8 46.74(12) . . . . ?
O2 C3 C7 C18 170.48(9) . . . . ?
O4 C3 C7 C6 33.96(11) . . . . ?
O4 C3 C7 C8 154.79(10) . . . . ?
O4 C3 C7 C18 -81.47(11) . . . . ?
O4 C5 C6 C7 -35.54(11) . . . . ?
O16 N15 C12 C11 3.62(17) . . . . ?
O16 N15 C12 C13 -174.50(12) . . . . ?
O17 N15 C12 C11 -177.40(12) . . . . ?
O17 N15 C12 C13 4.49(18) . . . . ?
N15 C12 C13 C14 176.55(11) . . . . ?
C23 C3 C7 C6 162.07(11) . . . . ?
C23 C3 C7 C8 -77.09(14) . . . . ?
C23 C3 C7 C18 46.65(15) . . . . ?
C3 O4 C5 O1 -54.45(10) . . . . ?
C3 O4 C5 C6 57.43(11) . . . . ?
C3 O4 C5 C22 -170.94(11) . . . . ?
C3 C7 C8 C9 167.39(10) . . . . ?
C3 C7 C18 O18 93.22(15) . . . . ?
C3 C7 C18 O19 -86.17(12) . . . . ?
C5 O1 O2 C3 0.40(11) . . . . ?
C5 O4 C3 O2 54.95(10) . . . . ?
C5 O4 C3 C23 170.88(11) . . . . ?
C5 O4 C3 C7 -56.59(10) . . . . ?
C5 C6 C7 C3 1.07(11) . . . . ?
C5 C6 C7 C8 -116.90(11) . . . . ?
C5 C6 C7 C18 115.64(10) . . . . ?
C6 C7 C8 C9 -81.56(13) . . . . ?
C6 C7 C18 O18 -14.67(17) . . . . ?
C6 C7 C18 O19 165.94(10) . . . . ?
C7 C8 C9 C10 -148.77(11) . . . . ?
C7 C8 C9 C14 31.60(17) . . . . ?
C8 C7 C18 O18 -143.66(13) . . . . ?
C8 C7 C18 O19 36.95(14) . . . . ?
C8 C9 C10 C11 178.32(11) . . . . ?
C8 C9 C14 C13 -178.84(12) . . . . ?
C9 C10 C11 C12 0.78(19) . . . . ?
C10 C9 C14 C13 1.53(19) . . . . ?
C10 C11 C12 N15 -177.03(11) . . . . ?
C10 C11 C12 C13 1.03(19) . . . . ?
C11 C12 C13 C14 -1.49(19) . . . . ?
C12 C13 C14 C9 0.17(19) . . . . ?
C14 C9 C10 C11 -2.02(19) . . . . ?
C18 O19 C20 C21 -173.85(11) . . . . ?
C18 C7 C8 C9 45.15(14) . . . . ?
C20 O19 C18 O18 2.83(18) . . . . ?
C20 O19 C18 C7 -177.77(10) . . . . ?
C22 C5 C6 C7 -163.53(11) . . . . ?

_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 1.164
_oxdiff_exptl_absorpt_empirical_full_min 0.903
####################################################################### 
# 
# 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_23as31
_database_code_depnum_ccdc_archive 'CCDC 2476572'
loop_
_audit_author_name
_audit_author_address
'Anna Dmitrievna Maksimova'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-07-28 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O8, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C16 H19 N O9'
_chemical_formula_weight         369.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   37.699(5)
_cell_length_b                   7.8969(12)
_cell_length_c                   11.6321(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.505(8)
_cell_angle_gamma                90
_cell_volume                     3461.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3214
_cell_measurement_theta_min      4.70
_cell_measurement_theta_max      64.99

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    1.008
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3977
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker d8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2939
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         66.570
_diffrn_reflns_theta_full        66.570
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2939
_reflns_number_gt                2175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+18.4574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     287
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_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 0.4781(4) 0.378(3) 0.4858(18) 0.035(3) Uani 0.5 1 d D . P A 1
H1 H 0.476(5) 0.34(2) 0.552(7) 0.053 Uiso 0.5 1 d D U P B 1
O1' O 0.4745(4) 0.341(2) 0.5150(16) 0.031(3) Uani 0.5 1 d D . P A 2
H1' H 0.490(3) 0.407(15) 0.491(12) 0.046 Uiso 0.5 1 d D U P C 2
O2 O 0.44173(7) 0.4405(4) 0.5042(2) 0.0277(7) Uani 1 1 d D . . . .
O3 O 0.41873(8) 0.2821(4) 0.3478(3) 0.0352(8) Uani 1 1 d . . . . .
O4 O 0.37985(9) 0.0987(4) 0.4406(3) 0.0369(8) Uani 1 1 d . . . . .
O5 O 0.37965(9) 0.1666(4) 0.5587(2) 0.0365(8) Uani 1 1 d . . . . .
O6 O 0.36507(8) 0.4103(4) 0.6376(2) 0.0310(8) Uani 1 1 d . . . . .
O7 O 0.2783(10) 1.155(3) 0.568(2) 0.049(5) Uani 0.65(7) 1 d . . P D 1
O7' O 0.2897(11) 1.163(5) 0.585(4) 0.049(5) Uani 0.35(7) 1 d . . P D 2
O8 O 0.26313(9) 1.0050(4) 0.7117(3) 0.0431(9) Uani 1 1 d . . . . .
N1 N 0.27724(10) 1.0207(5) 0.6196(3) 0.0312(9) Uani 1 1 d . . . . .
C1 C 0.42717(11) 0.4490(6) 0.3902(3) 0.0266(10) Uani 1 1 d . . . . .
C2 C 0.39158(10) 0.5355(5) 0.4053(3) 0.0225(9) Uani 1 1 d . . . . .
H2A H 0.384299 0.598828 0.335087 0.027 Uiso 1 1 calc R U . . .
H2B H 0.392545 0.614573 0.471351 0.027 Uiso 1 1 calc R U . . .
C3 C 0.36616(10) 0.3887(5) 0.4272(3) 0.0187(9) Uani 1 1 d . . . . .
C4 C 0.38295(11) 0.2401(5) 0.3629(3) 0.0255(10) Uani 1 1 d . . . . .
C5 C 0.36941(11) 0.3328(5) 0.5507(3) 0.0228(9) Uani 1 1 d . . . . .
C6 C 0.36695(12) 0.1773(6) 0.2508(4) 0.0320(11) Uani 1 1 d . . . . .
H6A H 0.367216 0.268576 0.193728 0.048 Uiso 1 1 calc R U . . .
H6B H 0.342429 0.141306 0.262425 0.048 Uiso 1 1 calc R U . . .
H6C H 0.380806 0.081178 0.223236 0.048 Uiso 1 1 calc R U . . .
C7 C 0.45164(12) 0.5296(8) 0.3071(4) 0.0426(14) Uani 1 1 d . . . . .
H7A H 0.457517 0.644570 0.333035 0.064 Uiso 1 1 calc R U . . .
H7B H 0.439997 0.534715 0.230827 0.064 Uiso 1 1 calc R U . . .
H7C H 0.473426 0.462489 0.302906 0.064 Uiso 1 1 calc R U . . .
C8 C 0.32692(10) 0.4266(5) 0.3918(3) 0.0203(9) Uani 1 1 d . . . . .
H8A H 0.325191 0.442473 0.307413 0.024 Uiso 1 1 calc R U . . .
H8B H 0.312142 0.327558 0.411334 0.024 Uiso 1 1 calc R U . . .
C9 C 0.31244(10) 0.5805(5) 0.4493(3) 0.0188(9) Uani 1 1 d . . . . .
C10 C 0.31674(11) 0.7413(5) 0.4008(3) 0.0252(10) Uani 1 1 d . . . . .
H10 H 0.327849 0.750992 0.328712 0.030 Uiso 1 1 calc R U . . .
C11 C 0.30532(11) 0.8856(5) 0.4547(3) 0.0254(10) Uani 1 1 d . . . . .
H11 H 0.308449 0.993977 0.421015 0.030 Uiso 1 1 calc R U . . .
C12 C 0.28921(10) 0.8685(5) 0.5591(3) 0.0200(9) Uani 1 1 d . . . . .
C13 C 0.28313(10) 0.7142(5) 0.6089(3) 0.0195(9) Uani 1 1 d . . . . .
H13 H 0.271116 0.706342 0.679531 0.023 Uiso 1 1 calc R U . . .
C14 C 0.29494(10) 0.5699(5) 0.5538(3) 0.0194(9) Uani 1 1 d . . . . .
H14 H 0.291100 0.462074 0.587467 0.023 Uiso 1 1 calc R U . . .
O1S O 0.49215(18) 0.1257(8) 0.6324(6) 0.0421(17) Uani 0.5 1 d . . P E -1
O2S O 0.499(2) -0.0989(6) 0.755(6) 0.030(3) Uani 0.5 1 d . U P E -1
C1S C 0.4843(3) -0.0179(16) 0.6595(10) 0.030(2) Uani 0.5 1 d . U P E -1
C2S C 0.4557(9) -0.124(4) 0.606(3) 0.024(4) Uani 0.5 1 d . U P E -1
H2SA H 0.465789 -0.230336 0.578981 0.035 Uiso 0.5 1 calc R U P E -1
H2SB H 0.444586 -0.062815 0.541473 0.035 Uiso 0.5 1 calc R U P E -1
H2SC H 0.437768 -0.148271 0.663670 0.035 Uiso 0.5 1 calc R U P E -1
C3S C 0.5298(3) -0.0065(15) 0.8063(10) 0.033(3) Uani 0.5 1 d . U P E -1
H3SA H 0.523068 0.110292 0.827514 0.040 Uiso 0.5 1 calc R U P E -1
H3SB H 0.549351 -0.001009 0.751173 0.040 Uiso 0.5 1 calc R U P E -1
C4S C 0.5410(10) -0.105(5) 0.911(3) 0.040(6) Uani 0.5 1 d . U P E -1
H4SA H 0.547784 -0.219833 0.888216 0.060 Uiso 0.5 1 calc R U P E -1
H4SB H 0.521269 -0.110746 0.963831 0.060 Uiso 0.5 1 calc R U P E -1
H4SC H 0.561313 -0.048933 0.948914 0.060 Uiso 0.5 1 calc R U P E -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.477(12) . ?
O1 H1 0.84(2) . ?
O1' O2 1.468(11) . ?
O1' H1' 0.84(2) . ?
O2 C1 1.423(5) . ?
O3 C4 1.405(5) . ?
O3 C1 1.440(5) . ?
O4 C4 1.443(5) . ?
O4 O5 1.475(4) . ?
O5 C5 1.370(5) . ?
O6 C5 1.197(5) . ?
O7 N1 1.22(2) . ?
O7' N1 1.29(4) . ?
O8 N1 1.215(5) . ?
N1 C12 1.470(5) . ?
C1 C7 1.496(6) . ?
C1 C2 1.520(6) . ?
C2 C3 1.530(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C5 1.505(5) . ?
C3 C4 1.537(5) . ?
C3 C8 1.554(5) . ?
C4 C6 1.507(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.498(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.401(5) . ?
C9 C10 1.401(6) . ?
C10 C11 1.375(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(6) . ?
C13 C14 1.387(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O1S C1S 1.216(13) . ?
O2S C1S 1.38(8) . ?
O2S C3S 1.49(8) . ?
C1S C2S 1.49(4) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C3S C4S 1.49(4) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?

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
O2 O1 H1 84(10) . . ?
O2 O1' H1' 103(10) . . ?
C1 O2 O1' 114.1(8) . . ?
C1 O2 O1 102.6(9) . . ?
C4 O3 C1 112.2(3) . . ?
C4 O4 O5 107.7(3) . . ?
C5 O5 O4 107.1(3) . . ?
O8 N1 O7 122.9(11) . . ?
O8 N1 O7' 122(2) . . ?
O8 N1 C12 119.0(4) . . ?
O7 N1 C12 117.5(11) . . ?
O7' N1 C12 117(2) . . ?
O2 C1 O3 110.6(3) . . ?
O2 C1 C7 113.1(3) . . ?
O3 C1 C7 107.6(4) . . ?
O2 C1 C2 103.5(3) . . ?
O3 C1 C2 105.3(3) . . ?
C7 C1 C2 116.4(4) . . ?
C1 C2 C3 103.7(3) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C5 C3 C2 110.2(3) . . ?
C5 C3 C4 102.5(3) . . ?
C2 C3 C4 103.3(3) . . ?
C5 C3 C8 111.3(3) . . ?
C2 C3 C8 114.0(3) . . ?
C4 C3 C8 114.8(3) . . ?
O3 C4 O4 110.8(3) . . ?
O3 C4 C6 109.4(3) . . ?
O4 C4 C6 104.5(4) . . ?
O3 C4 C3 106.9(3) . . ?
O4 C4 C3 104.2(3) . . ?
C6 C4 C3 120.8(3) . . ?
O6 C5 O5 118.5(4) . . ?
O6 C5 C3 130.3(4) . . ?
O5 C5 C3 111.2(3) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C3 113.2(3) . . ?
C9 C8 H8A 108.9 . . ?
C3 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C3 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 117.8(4) . . ?
C14 C9 C8 121.6(4) . . ?
C10 C9 C8 120.6(3) . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 118.1(4) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 122.8(4) . . ?
C13 C12 N1 117.8(4) . . ?
C11 C12 N1 119.3(4) . . ?
C12 C13 C14 118.4(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C1S O2S C3S 113(2) . . ?
O1S C1S O2S 123(3) . . ?
O1S C1S C2S 126.6(17) . . ?
O2S C1S C2S 110(3) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O2S C3S C4S 106(3) . . ?
O2S C3S H3SA 110.6 . . ?
C4S C3S H3SA 110.6 . . ?
O2S C3S H3SB 110.6 . . ?
C4S C3S H3SB 110.6 . . ?
H3SA C3S H3SB 108.7 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?

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
C4 O4 O5 C5 21.8(4) . . . . ?
O1' O2 C1 O3 60.0(9) . . . . ?
O1 O2 C1 O3 75.3(10) . . . . ?
O1' O2 C1 C7 -60.9(9) . . . . ?
O1 O2 C1 C7 -45.6(10) . . . . ?
O1' O2 C1 C2 172.3(8) . . . . ?
O1 O2 C1 C2 -172.4(9) . . . . ?
C4 O3 C1 O2 95.8(4) . . . . ?
C4 O3 C1 C7 -140.2(4) . . . . ?
C4 O3 C1 C2 -15.4(4) . . . . ?
O2 C1 C2 C3 -88.9(4) . . . . ?
O3 C1 C2 C3 27.3(4) . . . . ?
C7 C1 C2 C3 146.4(4) . . . . ?
C1 C2 C3 C5 80.3(4) . . . . ?
C1 C2 C3 C4 -28.6(4) . . . . ?
C1 C2 C3 C8 -153.8(3) . . . . ?
C1 O3 C4 O4 -116.1(4) . . . . ?
C1 O3 C4 C6 129.2(4) . . . . ?
C1 O3 C4 C3 -3.2(4) . . . . ?
O5 O4 C4 O3 86.9(4) . . . . ?
O5 O4 C4 C6 -155.4(3) . . . . ?
O5 O4 C4 C3 -27.7(4) . . . . ?
C5 C3 C4 O3 -94.4(4) . . . . ?
C2 C3 C4 O3 20.2(4) . . . . ?
C8 C3 C4 O3 144.8(3) . . . . ?
C5 C3 C4 O4 22.9(4) . . . . ?
C2 C3 C4 O4 137.5(3) . . . . ?
C8 C3 C4 O4 -97.8(4) . . . . ?
C5 C3 C4 C6 139.8(4) . . . . ?
C2 C3 C4 C6 -105.7(4) . . . . ?
C8 C3 C4 C6 19.0(6) . . . . ?
O4 O5 C5 O6 175.0(4) . . . . ?
O4 O5 C5 C3 -6.2(4) . . . . ?
C2 C3 C5 O6 58.8(6) . . . . ?
C4 C3 C5 O6 168.2(4) . . . . ?
C8 C3 C5 O6 -68.6(6) . . . . ?
C2 C3 C5 O5 -119.8(4) . . . . ?
C4 C3 C5 O5 -10.4(4) . . . . ?
C8 C3 C5 O5 112.7(4) . . . . ?
C5 C3 C8 C9 68.8(4) . . . . ?
C2 C3 C8 C9 -56.5(4) . . . . ?
C4 C3 C8 C9 -175.4(3) . . . . ?
C3 C8 C9 C14 -91.4(4) . . . . ?
C3 C8 C9 C10 87.2(4) . . . . ?
C14 C9 C10 C11 2.0(6) . . . . ?
C8 C9 C10 C11 -176.6(4) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C10 C11 C12 C13 -2.2(6) . . . . ?
C10 C11 C12 N1 179.0(4) . . . . ?
O8 N1 C12 C13 1.3(6) . . . . ?
O7 N1 C12 C13 -170(2) . . . . ?
O7' N1 C12 C13 165(2) . . . . ?
O8 N1 C12 C11 -179.8(4) . . . . ?
O7 N1 C12 C11 8(2) . . . . ?
O7' N1 C12 C11 -16(2) . . . . ?
C11 C12 C13 C14 2.5(6) . . . . ?
N1 C12 C13 C14 -178.7(3) . . . . ?
C12 C13 C14 C9 -0.5(6) . . . . ?
C10 C9 C14 C13 -1.7(6) . . . . ?
C8 C9 C14 C13 176.9(4) . . . . ?
C3S O2S C1S O1S -12(5) . . . . ?
C3S O2S C1S C2S 175(3) . . . . ?
C1S O2S C3S C4S 177(3) . . . . ?

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
O1^a H1^a O1S^a 0.84(2) 1.99(12) 2.668(15) 136(16) . yes
O1'^b H1'^b O1'^b 0.84(2) 2.40(7) 3.19(4) 157(14) 5_666 yes

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.070



